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A NEW BENCHMARK FOR LUXURY LIVING IN WINCHESTER. Introducing a truly one-of-a kind estate—an extraordinary new residence created without compromise on approximately one private acre at the end of a cul-de-sac. Encompassing nearly 10,000 SF, 21 rooms, 6 bedrooms and 7 baths, this remarkable property brings together architectural presence, exceptional craftsmanship, advanced technology and resort-caliber amenities rarely found in a single Greater Boston residence.Beyond its gated entrance and heated driveway, sophisticated interiors unfold through grand entertaining spaces, a statement chef’s kitchen, library/office with wet bar, glass-enclosed fitness studio, acoustically designed cinema, wine lounge and underground wine cellar. The exceptional primary suite features a luxurious dressing room and dramatic two-tier panoramic veranda overlooking the grounds.Outside, the estate transforms into a private resort: spectacular pool with waterfall, integrated spa, flame features and automatic cover; covered outdoor kitchen; sunken conversation lounge with central fire feature; covered dining terrace with fireplace; and beautifully designed grounds offering extraordinary privacy.Behind the elegance is equally impressive infrastructure: 18 heating zones, 9 cooling zones, 600-amp electrical service, approximately 2.5M BTU gas capacity, integrated AV/security, automated gated entry and a 3-car climate-conscious auto lounge with porcelain flooring and dual EV charging.Minutes from Winchester Center and convenient to Boston, this is far more than exceptional new construction. It is a meticulously conceived private estate where architecture, technology, wellness, entertainment and resort living converge—created for the buyer seeking something that simply cannot be replicated.

6 Beds ⋅ 7 Baths ⋅ 73585235 MLS

A NEW BENCHMARK FOR LUXURY LIVING IN WINCHESTER. Introducing a truly one-of-a kind estate—an extraordinary new residence created without compromise on approximately one private acre at the end of a cul-de-sac. Encompassing nearly 10,000 SF, 21 rooms, 6 bedrooms and 7 baths, this remarkable property brings together architectural presence, exceptional craftsmanship, advanced technology and resort-caliber amenities rarely found in a single Greater Boston residence.Beyond its gated entrance and heated driveway, sophisticated interiors unfold through grand entertaining spaces, a statement chef’s kitchen, library/office with wet bar, glass-enclosed fitness studio, acoustically designed cinema, wine lounge and underground wine cellar. The exceptional primary suite features a luxurious dressing room and dramatic two-tier panoramic veranda overlooking the grounds.Outside, the estate transforms into a private resort: spectacular pool with waterfall, integrated spa, flame features and automatic cover; covered outdoor kitchen; sunken conversation lounge with central fire feature; covered dining terrace with fireplace; and beautifully designed grounds offering extraordinary privacy.Behind the elegance is equally impressive infrastructure: 18 heating zones, 9 cooling zones, 600-amp electrical service, approximately 2.5M BTU gas capacity, integrated AV/security, automated gated entry and a 3-car climate-conscious auto lounge with porcelain flooring and dual EV charging.Minutes from Winchester Center and convenient to Boston, this is far more than exceptional new construction. It is a meticulously conceived private estate where architecture, technology, wellness, entertainment and resort living converge—created for the buyer seeking something that simply cannot be replicated.

15 Vinson Circle, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.

$3,299,000

Ideally situated in one of Winchester’s most serene neighborhoods, this exceptional residence offers impressive scale, thoughtful design, and remarkable versatility in a quiet, peaceful setting. It also represents one of Winchester's best values, with tremendous square footage and an au-pair/in-law apartment. Surrounded by beautiful homes and a sense of established elegance, this is a property designed to feel both private and welcoming. Thoughtfully expanded and beautifully built, the home offers 7 bedrooms and 7.5 baths, with generous living spaces designed for both everyday comfort and effortless entertaining. At the heart of the home, a stunning chef’s kitchen opens seamlessly to a dramatic fireplaced living room with soaring cathedral ceilings, creating a warm and inviting gathering space filled with natural light. There is also a family room, also with a fireplace and large picture windows, allowing for an abundance of sunlight. Explore further and you'll find a huge butler's pantry, a must-have feature in today's homes. There is also a wet bar with a beverage fridge. This is a home that has been very thoughtfully designed for how today's buyers actually live, but what truly distinguishes it is the flexibility of design. A private two-bedroom suite offers its own living area, office, wet bar, and full bath, providing an exceptional option for an au pair, extended stays, guests, returning college students or a more private living arrangement. The finished lower level adds even more space for recreation, fitness, entertaining, or simply spreading out. Beautifully proportioned rooms, exceptional functionality, and a serene neighborhood setting come together to create a home that feels substantial yet comfortable, sophisticated yet wonderfully livable. The natural light is exceptional, and outside, an oversized lot offers plenty of play space and a deck to hang out on. Just moments from Mullen Field, close to the town center and trains and an easy trip to Lexington or Cambridge, 1 Plymouth offers a rare opportunity to enjoy exceptional space and privacy in one of Winchester’s most sought-after neighborhoods.

7 Beds ⋅ 8 Baths ⋅ 73585058 MLS

Ideally situated in one of Winchester’s most serene neighborhoods, this exceptional residence offers impressive scale, thoughtful design, and remarkable versatility in a quiet, peaceful setting. It also represents one of Winchester's best values, with tremendous square footage and an au-pair/in-law apartment. Surrounded by beautiful homes and a sense of established elegance, this is a property designed to feel both private and welcoming. Thoughtfully expanded and beautifully built, the home offers 7 bedrooms and 7.5 baths, with generous living spaces designed for both everyday comfort and effortless entertaining. At the heart of the home, a stunning chef’s kitchen opens seamlessly to a dramatic fireplaced living room with soaring cathedral ceilings, creating a warm and inviting gathering space filled with natural light. There is also a family room, also with a fireplace and large picture windows, allowing for an abundance of sunlight. Explore further and you'll find a huge butler's pantry, a must-have feature in today's homes. There is also a wet bar with a beverage fridge. This is a home that has been very thoughtfully designed for how today's buyers actually live, but what truly distinguishes it is the flexibility of design. A private two-bedroom suite offers its own living area, office, wet bar, and full bath, providing an exceptional option for an au pair, extended stays, guests, returning college students or a more private living arrangement. The finished lower level adds even more space for recreation, fitness, entertaining, or simply spreading out. Beautifully proportioned rooms, exceptional functionality, and a serene neighborhood setting come together to create a home that feels substantial yet comfortable, sophisticated yet wonderfully livable. The natural light is exceptional, and outside, an oversized lot offers plenty of play space and a deck to hang out on. Just moments from Mullen Field, close to the town center and trains and an easy trip to Lexington or Cambridge, 1 Plymouth offers a rare opportunity to enjoy exceptional space and privacy in one of Winchester’s most sought-after neighborhoods.

1 Plymouth Rd., Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$1,529,000

An exceptional opportunity in one of Winchester’s most desirable neighborhoods, directly across from the Winchester Country Club. Set on a beautiful .39-acre lot, this distinctive 4-bedroom, 3.5-bath Colonial offers approximately 2,709 sq. ft. of living space, a 2-cargarage, generous room proportions, and a flexible floor plan ready for its next chapter. Offering wonderful possibilities with its generous proportions, flexible floor plan, and impressive setting, the property presents an ideal canvas for buyers looking to renovate and personalize a home to their exact vision. Reimagine the existing spaces with sophisticated modern finishes, create a timeless renovation that complements the home’s character, or explore the possibilities for a more extensive transformation. The spacious lot also provides plenty of room to enhance the outdoor experience with thoughtfully designed landscaping, gardens, patios, entertaining areas, or other outdoor amenities. Beyond the property itself, the location stands out, with the Winchester Country Club just across the street and downtown Winchester conveniently nearby, offering restaurants, cafés, shops, services, and commuter rail access to Boston. Convenient access to Winchester public schools, major routes, and nearby public transportation makes commuting and exploring the Greater Boston area easy. Bring your architect, contractor, and creativity and transform this property into something truly special. With its substantial lot, desirable neighborhood setting, proximity to downtown, and access to everything Winchester has to offer, 25 Arlington Street presents a rare chance to create a home that reflects your own style in an exceptional location.

4 Beds ⋅ 4 Baths ⋅ 73584817 MLS

An exceptional opportunity in one of Winchester’s most desirable neighborhoods, directly across from the Winchester Country Club. Set on a beautiful .39-acre lot, this distinctive 4-bedroom, 3.5-bath Colonial offers approximately 2,709 sq. ft. of living space, a 2-cargarage, generous room proportions, and a flexible floor plan ready for its next chapter. Offering wonderful possibilities with its generous proportions, flexible floor plan, and impressive setting, the property presents an ideal canvas for buyers looking to renovate and personalize a home to their exact vision. Reimagine the existing spaces with sophisticated modern finishes, create a timeless renovation that complements the home’s character, or explore the possibilities for a more extensive transformation. The spacious lot also provides plenty of room to enhance the outdoor experience with thoughtfully designed landscaping, gardens, patios, entertaining areas, or other outdoor amenities. Beyond the property itself, the location stands out, with the Winchester Country Club just across the street and downtown Winchester conveniently nearby, offering restaurants, cafés, shops, services, and commuter rail access to Boston. Convenient access to Winchester public schools, major routes, and nearby public transportation makes commuting and exploring the Greater Boston area easy. Bring your architect, contractor, and creativity and transform this property into something truly special. With its substantial lot, desirable neighborhood setting, proximity to downtown, and access to everything Winchester has to offer, 25 Arlington Street presents a rare chance to create a home that reflects your own style in an exceptional location.

25 Arlington St, Winchester

Listing courtesy of Listing Agent: Domingo Medina from Listing Office: Coldwell Banker Realty - Lexington.

$1,950,000

Welcome to 26 Mayflower Road, located in one of Winchester’s sought-after neighborhoods alongside Winchester Country Club. From the beautifully landscaped grounds to the updated front door, garage doors, and recently redone front steps, this home offers wonderful curb appeal from the moment you arrive. Inside, the main level is warm, inviting, and filled with natural light, featuring a comfortable living room with wood-burning fireplace, an open kitchen and dining area, and a sun-filled family room that opens directly to a private brick patio. Whether you're enjoying your morning coffee, grilling, gathering with friends, or simply relaxing at the end of the day, the indoor-outdoor flow makes this home especially easy to enjoy. The spacious primary suite offers double closets and a beautiful bath with double vanity sinks, soaking tub, and tiled walk-in shower. An attached guest/in-law suite with its own private entrance, full bath, and kitchenette provides exceptional flexibility for guests, extended family, an au pair, or a private work-from-home space. The finished lower level adds even more room to spread out, with two additional living spaces and a full bathroom—perfect for a teen suite, home office, gym, playroom, or media space. Outside, beautiful landscaping, irrigation, and the expansive brick patio create a private setting for entertaining or simply enjoying the outdoors. Ideally located near commuter routes, the MBTA Commuter Rail, shopping, restaurants, schools, and downtown Winchester, this is a home that offers the space and flexibility to fit the way you live, all in a location that makes getting where you need to go easy.

5 Beds ⋅ 4 Baths ⋅ 73584117 MLS

Welcome to 26 Mayflower Road, located in one of Winchester’s sought-after neighborhoods alongside Winchester Country Club. From the beautifully landscaped grounds to the updated front door, garage doors, and recently redone front steps, this home offers wonderful curb appeal from the moment you arrive. Inside, the main level is warm, inviting, and filled with natural light, featuring a comfortable living room with wood-burning fireplace, an open kitchen and dining area, and a sun-filled family room that opens directly to a private brick patio. Whether you're enjoying your morning coffee, grilling, gathering with friends, or simply relaxing at the end of the day, the indoor-outdoor flow makes this home especially easy to enjoy. The spacious primary suite offers double closets and a beautiful bath with double vanity sinks, soaking tub, and tiled walk-in shower. An attached guest/in-law suite with its own private entrance, full bath, and kitchenette provides exceptional flexibility for guests, extended family, an au pair, or a private work-from-home space. The finished lower level adds even more room to spread out, with two additional living spaces and a full bathroom—perfect for a teen suite, home office, gym, playroom, or media space. Outside, beautiful landscaping, irrigation, and the expansive brick patio create a private setting for entertaining or simply enjoying the outdoors. Ideally located near commuter routes, the MBTA Commuter Rail, shopping, restaurants, schools, and downtown Winchester, this is a home that offers the space and flexibility to fit the way you live, all in a location that makes getting where you need to go easy.

26 Mayflower Road, Winchester

Listing courtesy of Listing Agent: Nicole M. Condon from Listing Office: The Simply Sold Realty Co..

$1,195,000

Introducing 4 Stone Ave, a charming 3 bed, 1.5 bath Colonial Style home, one block from Muraco School, and minutes from the Middlesex Fells Reservation, offering over 2,575 acres of pristine woodlands, reservoirs, and scenic trails perfect for outdoor recreation. Beautiful updates complement the home’s original oak woodwork, including stained oak Harvey windows with tilt in sashes. The spacious front foyer opens into the living room with a wood burning fireplace. The formal dining room leads out to a serene private rear deck, overlooking a fully fenced yard with native plantings. The sizable kitchen highlights electric cooking, a built in microwave, and peninsula providing additional seating. A side addition added a large front to back family room with abundant natural light, providing even more livable space on the first floor. A private home office with classic French door completes this level. Upstairs, you’ll find a 2021 renovated full bathroom, three sizable bedrooms, and extensive storage space including 25FT attic closet. The walk out basement offers W/D, an above grade, finished room perfect for a home gym or office, and unfinished storage space. A one car garage, off street parking for 3 additional cars and cost efficient solar panels add everyday practicality. Just minutes from vibrant Winchester Center, this home offers access to local shops, cafés, highly rated restaurants, two MBTA commuter rail stations and Winchester’s acclaimed public school system, along with easy access to I-93, Route 128 and Route 3.

3 Beds ⋅ 2 Baths ⋅ 73582171 MLS

Introducing 4 Stone Ave, a charming 3 bed, 1.5 bath Colonial Style home, one block from Muraco School, and minutes from the Middlesex Fells Reservation, offering over 2,575 acres of pristine woodlands, reservoirs, and scenic trails perfect for outdoor recreation. Beautiful updates complement the home’s original oak woodwork, including stained oak Harvey windows with tilt in sashes. The spacious front foyer opens into the living room with a wood burning fireplace. The formal dining room leads out to a serene private rear deck, overlooking a fully fenced yard with native plantings. The sizable kitchen highlights electric cooking, a built in microwave, and peninsula providing additional seating. A side addition added a large front to back family room with abundant natural light, providing even more livable space on the first floor. A private home office with classic French door completes this level. Upstairs, you’ll find a 2021 renovated full bathroom, three sizable bedrooms, and extensive storage space including 25FT attic closet. The walk out basement offers W/D, an above grade, finished room perfect for a home gym or office, and unfinished storage space. A one car garage, off street parking for 3 additional cars and cost efficient solar panels add everyday practicality. Just minutes from vibrant Winchester Center, this home offers access to local shops, cafés, highly rated restaurants, two MBTA commuter rail stations and Winchester’s acclaimed public school system, along with easy access to I-93, Route 128 and Route 3.

4 Stone Ave, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.

$1,000,000

Storybook charm meets relaxed, easy living in this inviting Winchester Colonial, ideally located near the natural beauty of the Fells Reservation, Muraco Elementary, and convenient commuter routes. Set on a lovely lot with mature plantings, the property offers a private-feeling outdoor setting, a detached two-car garage, and pretty, original architectural details throughout. Inside, natural light fills the freshly painted interior. The fireplaced living room with wood stove flows seamlessly into the updated kitchen and dining room, creating an easy connection for everyday living and entertaining. The dining room opens to a bright, welcoming sunroom - an ideal spot for morning coffee, reading, or enjoying views of the surrounding yard. Upstairs, two generously sized bedrooms are joined by a third bedroom with a walk-up to additional attic storage, and a charming full bath. The lower level provides even more versatility with a finished bonus room, laundry, plentiful storage and exterior access. Thoughtfully maintained and move-in ready, this home combines timeless architectural character with smart updates and practical spaces designed for today’s lifestyle.

3 Beds ⋅ 1 Baths ⋅ 73581744 MLS

Storybook charm meets relaxed, easy living in this inviting Winchester Colonial, ideally located near the natural beauty of the Fells Reservation, Muraco Elementary, and convenient commuter routes. Set on a lovely lot with mature plantings, the property offers a private-feeling outdoor setting, a detached two-car garage, and pretty, original architectural details throughout. Inside, natural light fills the freshly painted interior. The fireplaced living room with wood stove flows seamlessly into the updated kitchen and dining room, creating an easy connection for everyday living and entertaining. The dining room opens to a bright, welcoming sunroom - an ideal spot for morning coffee, reading, or enjoying views of the surrounding yard. Upstairs, two generously sized bedrooms are joined by a third bedroom with a walk-up to additional attic storage, and a charming full bath. The lower level provides even more versatility with a finished bonus room, laundry, plentiful storage and exterior access. Thoughtfully maintained and move-in ready, this home combines timeless architectural character with smart updates and practical spaces designed for today’s lifestyle.

23 Stone Ave., Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,850,000

Welcome to One Overlook Way in Winchester. This spacious 4+ bedroom center-entrance Colonial is tucked away on a short cul-de-sac off High Street, in a premier location close to Ambrose Elementary School and the Winchester Country Club. The foyer opens to a thoughtfully designed floor plan with wonderful flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen also opens naturally into the cozy family room - with gas fireplace, custom built-ins and access to the back and side yard, the family room will be well utilized! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a home office or storage. The finished lower level adds even more usable space, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.

4 Beds ⋅ 3 Baths ⋅ 73581571 MLS

Welcome to One Overlook Way in Winchester. This spacious 4+ bedroom center-entrance Colonial is tucked away on a short cul-de-sac off High Street, in a premier location close to Ambrose Elementary School and the Winchester Country Club. The foyer opens to a thoughtfully designed floor plan with wonderful flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen also opens naturally into the cozy family room - with gas fireplace, custom built-ins and access to the back and side yard, the family room will be well utilized! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a home office or storage. The finished lower level adds even more usable space, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.

1 Overlook Way, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,080,000

Opportunities and possibilities for builders or handyman!! At 6 Reservoir Street, Winchester, a distinguished single-family residence on an expansive 10818 square foot lot. This property represents a unique opportunity for refined living within a desirable community. The residence encompasses three well-proportioned bedrooms plus walk-up to a generously sized attic and one full bathroom. Traditional wrap-around porch in front, and large deck at the rear accessed from the driveway which enters from the street behind. Great location close by to the reservoir and Fells Reservation with easy highway access as well. Sell by owner and AS IS conditions.

3 Beds ⋅ 1 Baths ⋅ 73578621 MLS

Opportunities and possibilities for builders or handyman!! At 6 Reservoir Street, Winchester, a distinguished single-family residence on an expansive 10818 square foot lot. This property represents a unique opportunity for refined living within a desirable community. The residence encompasses three well-proportioned bedrooms plus walk-up to a generously sized attic and one full bathroom. Traditional wrap-around porch in front, and large deck at the rear accessed from the driveway which enters from the street behind. Great location close by to the reservoir and Fells Reservation with easy highway access as well. Sell by owner and AS IS conditions.

6 Reservoir Street, Winchester

Listing courtesy of Listing Agent: Dongjun Lou from Listing Office: HMW Real Estate, LLC.

$2,600,000

RARE WATERFRONT OPPORTUNITY on Upper Mystic Lake with spectacular sunset views! Tucked away on Lakeview Terrace, this special 1910 home offers a combination rarely found in Winchester: waterfront living, privacy, beautiful southwest light and exceptional convenience. Gracious rooms, period details and quality craftsmanship give the home wonderful character, while its generous layout offers an exciting opportunity to update and create something truly special. The home features 5-6 bedrooms, a home office and expansive living spaces designed to take advantage of the lake views. The kitchen, renovated some years ago, was thoughtfully positioned so the view can be enjoyed while preparing meals. An unfinished lower level with high ceilings offers additional possibilities. Just steps from Wedgemere Commuter Rail Station, 1/2 mile to Shannon Beach and less than a mile to Winchester Center via the Tri-Community Bikeway. A remarkable setting, beautiful sunsets and an opportunity that may not come again for years. Don't delay your visit!

6 Beds ⋅ 4 Baths ⋅ 73578443 MLS

RARE WATERFRONT OPPORTUNITY on Upper Mystic Lake with spectacular sunset views! Tucked away on Lakeview Terrace, this special 1910 home offers a combination rarely found in Winchester: waterfront living, privacy, beautiful southwest light and exceptional convenience. Gracious rooms, period details and quality craftsmanship give the home wonderful character, while its generous layout offers an exciting opportunity to update and create something truly special. The home features 5-6 bedrooms, a home office and expansive living spaces designed to take advantage of the lake views. The kitchen, renovated some years ago, was thoughtfully positioned so the view can be enjoyed while preparing meals. An unfinished lower level with high ceilings offers additional possibilities. Just steps from Wedgemere Commuter Rail Station, 1/2 mile to Shannon Beach and less than a mile to Winchester Center via the Tri-Community Bikeway. A remarkable setting, beautiful sunsets and an opportunity that may not come again for years. Don't delay your visit!

7 Lakeview Terrace, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$3,200,000

A rare expression of quality, craftsmanship, and enduring style, 30 Willowdale Road presents an exceptional opportunity to own a newly constructed residence in one of Winchester’s most coveted neighborhoods. Set on a beautifully proportioned, large and level lot, this remarkable home has been thoughtfully conceived to offer the space, sophistication, and effortless lifestyle expected of a truly exceptional property.From the moment you enter, the quality is unmistakable. Gracious proportions, refined architectural details, exceptional craftsmanship, and carefully curated finishes create a home designed not simply for today, but with a sense of lasting beauty that will transcend trends for years to come. Every space feels considered, polished, and substantial, with an elevated yet welcoming character throughout.At the heart of the home, a spectacular chef’s kitchen pairs custom finishes with premium Viking appliances, creating a beautiful gathering place for everyday living and entertaining. Expansive living spaces flow naturally from one to the next, equally suited to intimate evenings, holiday celebrations, and a house full of family and friends. 8 bedrooms and 6.5 baths provide extraordinary flexibility, privacy, and comfort, with abundant space for guests, home offices, fitness, recreation, and the evolving needs of modern life. Outside, the expansive level grounds are a luxury unto themselves, offering wonderful possibilities for outdoor entertaining, recreation, gardens, and the simple pleasure of having room to breathe. A two-car garage and the ease and efficiency of brand-new construction further enhance the lifestyle.Sophisticated without being showy and luxurious without sacrificing warmth, 30 Willowdale Road is the kind of home that feels exceptional today and will remain so for generations. A rare combination of location, land, craftsmanship, and enduring quality in a premier Winchester neighborhood.

8 Beds ⋅ 7 Baths ⋅ 73577116 MLS

A rare expression of quality, craftsmanship, and enduring style, 30 Willowdale Road presents an exceptional opportunity to own a newly constructed residence in one of Winchester’s most coveted neighborhoods. Set on a beautifully proportioned, large and level lot, this remarkable home has been thoughtfully conceived to offer the space, sophistication, and effortless lifestyle expected of a truly exceptional property.From the moment you enter, the quality is unmistakable. Gracious proportions, refined architectural details, exceptional craftsmanship, and carefully curated finishes create a home designed not simply for today, but with a sense of lasting beauty that will transcend trends for years to come. Every space feels considered, polished, and substantial, with an elevated yet welcoming character throughout.At the heart of the home, a spectacular chef’s kitchen pairs custom finishes with premium Viking appliances, creating a beautiful gathering place for everyday living and entertaining. Expansive living spaces flow naturally from one to the next, equally suited to intimate evenings, holiday celebrations, and a house full of family and friends. 8 bedrooms and 6.5 baths provide extraordinary flexibility, privacy, and comfort, with abundant space for guests, home offices, fitness, recreation, and the evolving needs of modern life. Outside, the expansive level grounds are a luxury unto themselves, offering wonderful possibilities for outdoor entertaining, recreation, gardens, and the simple pleasure of having room to breathe. A two-car garage and the ease and efficiency of brand-new construction further enhance the lifestyle.Sophisticated without being showy and luxurious without sacrificing warmth, 30 Willowdale Road is the kind of home that feels exceptional today and will remain so for generations. A rare combination of location, land, craftsmanship, and enduring quality in a premier Winchester neighborhood.

30 Willowdale Rd, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$974,900

A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! The property is set on a level, fenced corner lot with a side-street driveway, ACCESSIBLE FROM RIVER STREET, parking for 4 cars, and offering 3 bedrooms, a versatile bonus room (4 beds on public record), 2.5 baths and a layout that can adapt as your needs change. The main level blends classic character with everyday function, featuring hardwood floors, crown molding, arched openings, bay windows and an updated eat-in kitchen with stone counters, upgraded cabinetry, stainless appliances and gas cooking. A brand-new first-floor powder room adds convenience for everyday living and entertaining. Upstairs, two generously sized bedrooms are joined by two updated full baths, including a larger bath with double vanity, tiled shower and soaking tub. The finished third floor provides a third bedroom plus an additional flex space ideal for a home office, fitness room, playroom, hobby space or guests. Major recent improvements, besides the unused, first floor half bath, include brand-new central AC and a newly sodded yard. Current owners have also invested considerably into improvements from the kitchen (countertops/appliances/backsplash/flooring), to the main bathroom remodel on the 2nd floor, and even a rebuilding of the lower two staircases to increase functionality. Outside, enjoy a fenced backyard, patio, storage shed and rare off-street parking for four vehicles. The full basement provides additional laundry and storage space. Convenient to Winchester Center, local shops and dining, the commuter rail, the Middlesex Fells and major routes connecting Boston, Cambridge, Burlington and the surrounding metro area. Previously prepared conceptual expansion plans are available for buyers interested in exploring future possibilities.

3 Beds ⋅ 3 Baths ⋅ 73575764 MLS

A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! The property is set on a level, fenced corner lot with a side-street driveway, ACCESSIBLE FROM RIVER STREET, parking for 4 cars, and offering 3 bedrooms, a versatile bonus room (4 beds on public record), 2.5 baths and a layout that can adapt as your needs change. The main level blends classic character with everyday function, featuring hardwood floors, crown molding, arched openings, bay windows and an updated eat-in kitchen with stone counters, upgraded cabinetry, stainless appliances and gas cooking. A brand-new first-floor powder room adds convenience for everyday living and entertaining. Upstairs, two generously sized bedrooms are joined by two updated full baths, including a larger bath with double vanity, tiled shower and soaking tub. The finished third floor provides a third bedroom plus an additional flex space ideal for a home office, fitness room, playroom, hobby space or guests. Major recent improvements, besides the unused, first floor half bath, include brand-new central AC and a newly sodded yard. Current owners have also invested considerably into improvements from the kitchen (countertops/appliances/backsplash/flooring), to the main bathroom remodel on the 2nd floor, and even a rebuilding of the lower two staircases to increase functionality. Outside, enjoy a fenced backyard, patio, storage shed and rare off-street parking for four vehicles. The full basement provides additional laundry and storage space. Convenient to Winchester Center, local shops and dining, the commuter rail, the Middlesex Fells and major routes connecting Boston, Cambridge, Burlington and the surrounding metro area. Previously prepared conceptual expansion plans are available for buyers interested in exploring future possibilities.

258 Cross St, Winchester

Listing courtesy of Listing Agent: Justin Blankenship from Listing Office: Fiv Realty Co.

$1,599,000

**JOIN US FOR AN OPEN HOUSE Saturday 10/3 11-12:30 ***Set on a generous lot in one of Winchester’s most highly sought-after locations, this stately brick colonial presents a rare opportunity to create your dream home. Offering 2,944 square feet of living space, with high ceilings & oak hardwood flooring. This classic residence has been lovingly enjoyed & maintained by one family and proudly showcases timeless architectural character, generously proportioned rooms, and an abundance of natural light. The inviting front to back living room features a fireplace and serves as a wonderful gathering space, along with formal dining room, eat in kitchen, 1/2 bath plus a sunroom/den and a home office! The upper floors offer 5 spacious bedrooms & provide exceptional flexibility for family, guests, office space, or future customization. Enjoy the rear deck and the vast lot with lush grass, gorgeous perennial gardens and flowering trees offering plenty of space for outdoor entertaining, gardening or expansion. With this home's beautiful brick exterior, classic charm, substantial lot, and premier location, it offers an exceptional opportunity to renovate, reimagine, and create your dream home!

5 Beds ⋅ 3 Baths ⋅ 73575069 MLS

**JOIN US FOR AN OPEN HOUSE Saturday 10/3 11-12:30 ***Set on a generous lot in one of Winchester’s most highly sought-after locations, this stately brick colonial presents a rare opportunity to create your dream home. Offering 2,944 square feet of living space, with high ceilings & oak hardwood flooring. This classic residence has been lovingly enjoyed & maintained by one family and proudly showcases timeless architectural character, generously proportioned rooms, and an abundance of natural light. The inviting front to back living room features a fireplace and serves as a wonderful gathering space, along with formal dining room, eat in kitchen, 1/2 bath plus a sunroom/den and a home office! The upper floors offer 5 spacious bedrooms & provide exceptional flexibility for family, guests, office space, or future customization. Enjoy the rear deck and the vast lot with lush grass, gorgeous perennial gardens and flowering trees offering plenty of space for outdoor entertaining, gardening or expansion. With this home's beautiful brick exterior, classic charm, substantial lot, and premier location, it offers an exceptional opportunity to renovate, reimagine, and create your dream home!

143 Arlington Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,300,000

Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

4 Beds ⋅ 3 Baths ⋅ 73574928 MLS

Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$2,995,000

A distinctive new construction home where exceptional scale, thoughtful design, and refined finishes come together. Offering approximately 6,500 sq ft of beautifully finished living space, 8 Priscilla Ln was designed to feel impressive yet inviting. Soaring ceilings, graceful archways, and a dramatic two-story living room establish the home's architectural character, while an open, flowing layout is equally suited for everyday living and entertaining. At the heart of the home, the chef's kitchen features custom cabinetry, Thermador appliances, an oversized island, and a spacious walk-in pantry. The primary suite is a true retreat with a spa-inspired bath and generous walk-in closet, while multiple additional bedrooms offer the privacy of en suite baths. Downstairs, ceilings exceeding 10 feet elevate an expansive finished lower level with tremendous flexibility for a media room, gym, au pair or guest accommodations, or additional living space. Designed by Salt and Stone Co. and complete with a two-car garage, this is a home defined by craftsmanship, presence, and details rarely found in new construction.

5 Beds ⋅ 6 Baths ⋅ 73574330 MLS

A distinctive new construction home where exceptional scale, thoughtful design, and refined finishes come together. Offering approximately 6,500 sq ft of beautifully finished living space, 8 Priscilla Ln was designed to feel impressive yet inviting. Soaring ceilings, graceful archways, and a dramatic two-story living room establish the home's architectural character, while an open, flowing layout is equally suited for everyday living and entertaining. At the heart of the home, the chef's kitchen features custom cabinetry, Thermador appliances, an oversized island, and a spacious walk-in pantry. The primary suite is a true retreat with a spa-inspired bath and generous walk-in closet, while multiple additional bedrooms offer the privacy of en suite baths. Downstairs, ceilings exceeding 10 feet elevate an expansive finished lower level with tremendous flexibility for a media room, gym, au pair or guest accommodations, or additional living space. Designed by Salt and Stone Co. and complete with a two-car garage, this is a home defined by craftsmanship, presence, and details rarely found in new construction.

8 Priscilla Lane, Winchester

Listing courtesy of Listing Agent: The Pezzano Group from Listing Office: Rise Signature Homes.

$3,149,000

Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by custom built-ins, fine cabinetry and beautiful millwork throughout. The newly renovated chef’s kitchen showcases quartz countertops, an oversized center island, two dishwashers and a butler’s pantry with wine fridge and ice maker, flowing seamlessly into the elegant dining room, living room and fireplaced family room overlooking the meticulously maintained grounds. A dedicated first-floor wing offers incredible flexibility for extended family, au pair or guests, while a private office with custom wet bar and additional spaces can easily accommodate two executive home offices. Upstairs, the grand primary suite is joined by four additional bedroom suites, each offering a private bath, sitting area and generous closet space. The third floor provides a completely private guest or teen suite with a full bath and two closets.The finished lower-level offers media, game and gym areas with a full bath and direct access to the inviting heated pool and lush landscaped grounds. Unmatched in scale and versatility with resort-like amenities, exceptional craftsmanship and a coveted West Side location, this remarkable home offers luxury living at its finest.

7 Beds ⋅ 8 Baths ⋅ 73573670 MLS

Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by custom built-ins, fine cabinetry and beautiful millwork throughout. The newly renovated chef’s kitchen showcases quartz countertops, an oversized center island, two dishwashers and a butler’s pantry with wine fridge and ice maker, flowing seamlessly into the elegant dining room, living room and fireplaced family room overlooking the meticulously maintained grounds. A dedicated first-floor wing offers incredible flexibility for extended family, au pair or guests, while a private office with custom wet bar and additional spaces can easily accommodate two executive home offices. Upstairs, the grand primary suite is joined by four additional bedroom suites, each offering a private bath, sitting area and generous closet space. The third floor provides a completely private guest or teen suite with a full bath and two closets.The finished lower-level offers media, game and gym areas with a full bath and direct access to the inviting heated pool and lush landscaped grounds. Unmatched in scale and versatility with resort-like amenities, exceptional craftsmanship and a coveted West Side location, this remarkable home offers luxury living at its finest.

37 Mayflower Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,650,000

Expansive living and unparalleled curb appeal define this exceptional five-bedroom garrison colonial, ideally positioned near the natural beauty and extensive trails of the Fells Reservation. Set in the highly regarded Muraco Elementary School district, this spacious home offers an inviting blend of timeless architecture, thoughtful updates, and remarkable flexibility for today’s lifestyle. The sun-filled first floor features an open, seamless flow designed for both everyday living and effortless entertaining. A thoughtfully appointed eat-in kitchen with premium Sub-Zero and Fisher & Paykel appliances opens to the dining space, creating an ideal setting for gathering. A wood-burning fireplace anchors the living room where you can watch the world go by from the gorgeous picture window. A home office, mudroom, and powder room add functionality to this level. Upstairs, the generous primary suite includes a full bath and convenient laundry, with tree-top views from the Juliet balcony, complemented by four additional bedrooms and a family bath. A finished walk-up attic provides valuable storage and flexible bonus space, while the finished lower level adds a generous family room and several bonus spaces ideal for a second home office, playroom, media space, or additional recreation area, with kitchenette and full bath allowing for ADU possibilities. Outside, enjoy a truly private retreat with a fully fenced yard and pristine in-ground pool, offering exceptional space for outdoor living, entertaining, and relaxation. A two-car attached garage adds everyday convenience. With generous proportions throughout, multiple flexible spaces, an inviting open floor plan, and close proximity to the Fells Reservation, this Winchester Highlands property offers a rare opportunity to enjoy space, privacy, and sophisticated everyday living in one of Winchester’s desirable neighborhoods.

5 Beds ⋅ 4 Baths ⋅ 73573887 MLS

Expansive living and unparalleled curb appeal define this exceptional five-bedroom garrison colonial, ideally positioned near the natural beauty and extensive trails of the Fells Reservation. Set in the highly regarded Muraco Elementary School district, this spacious home offers an inviting blend of timeless architecture, thoughtful updates, and remarkable flexibility for today’s lifestyle. The sun-filled first floor features an open, seamless flow designed for both everyday living and effortless entertaining. A thoughtfully appointed eat-in kitchen with premium Sub-Zero and Fisher & Paykel appliances opens to the dining space, creating an ideal setting for gathering. A wood-burning fireplace anchors the living room where you can watch the world go by from the gorgeous picture window. A home office, mudroom, and powder room add functionality to this level. Upstairs, the generous primary suite includes a full bath and convenient laundry, with tree-top views from the Juliet balcony, complemented by four additional bedrooms and a family bath. A finished walk-up attic provides valuable storage and flexible bonus space, while the finished lower level adds a generous family room and several bonus spaces ideal for a second home office, playroom, media space, or additional recreation area, with kitchenette and full bath allowing for ADU possibilities. Outside, enjoy a truly private retreat with a fully fenced yard and pristine in-ground pool, offering exceptional space for outdoor living, entertaining, and relaxation. A two-car attached garage adds everyday convenience. With generous proportions throughout, multiple flexible spaces, an inviting open floor plan, and close proximity to the Fells Reservation, this Winchester Highlands property offers a rare opportunity to enjoy space, privacy, and sophisticated everyday living in one of Winchester’s desirable neighborhoods.

117 Highland, Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$2,199,000

Welcome to 19 Hancock Street, a stunning transformation where timeless New England character meets sophisticated modern living. Completely reimagined through an extensive renovation, this exceptional Winchester residence preserves the charm and presence of a classic home while delivering the design, finishes and functionality expected for today’s lifestyle. The beautifully designed first floor features a bright, open layout with an effortless flow from room to room, creating an ideal setting for both elegant entertaining and comfortable everyday living. Thoughtful details throughout include a spacious pantry and dedicated mudroom, blending style with exceptional functionality. Upstairs, four bedrooms include a luxurious primary suite designed as a private retreat, complete with a beautifully appointed bath and oversized walk-in shower. Convenient second-floor laundry and well-designed secondary bedrooms make this level as practical as it is polished. The finished lower level offers another impressive dimension of living space, perfect for a media room, home gym, playroom, office or guest retreat. With 3.5 beautifully finished baths, a two-car garage, and a rear deck ideal for outdoor dining and entertaining, every level of the home has been thoughtfully considered. All of this is set in one of Winchester’s most convenient locations—just minutes from Winchester Center, the commuter rail, shops, dining and schools. Classic character, completely renewed. Modern luxury without sacrificing warmth. 19 Hancock Street is a rare opportunity to enjoy the best of Winchester living in a home that feels both established and entirely new.

4 Beds ⋅ 4 Baths ⋅ 73572955 MLS

Welcome to 19 Hancock Street, a stunning transformation where timeless New England character meets sophisticated modern living. Completely reimagined through an extensive renovation, this exceptional Winchester residence preserves the charm and presence of a classic home while delivering the design, finishes and functionality expected for today’s lifestyle. The beautifully designed first floor features a bright, open layout with an effortless flow from room to room, creating an ideal setting for both elegant entertaining and comfortable everyday living. Thoughtful details throughout include a spacious pantry and dedicated mudroom, blending style with exceptional functionality. Upstairs, four bedrooms include a luxurious primary suite designed as a private retreat, complete with a beautifully appointed bath and oversized walk-in shower. Convenient second-floor laundry and well-designed secondary bedrooms make this level as practical as it is polished. The finished lower level offers another impressive dimension of living space, perfect for a media room, home gym, playroom, office or guest retreat. With 3.5 beautifully finished baths, a two-car garage, and a rear deck ideal for outdoor dining and entertaining, every level of the home has been thoughtfully considered. All of this is set in one of Winchester’s most convenient locations—just minutes from Winchester Center, the commuter rail, shops, dining and schools. Classic character, completely renewed. Modern luxury without sacrificing warmth. 19 Hancock Street is a rare opportunity to enjoy the best of Winchester living in a home that feels both established and entirely new.

19 Hancock Street, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.

$1,098,000

Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a dining area with sliders to a private deck and fully-fenced, tree-lined yard. Upstairs features three bedrooms, including a impressive primary suite with a stunning walk-in closet, and a full bath. Major upgrades include deleading (2018), basement asbestos removal (2019), a newer furnace, and a brand-new water heater (2024). Ideally located just 1 mile from Winchester Center, top schools, dining, and the MBTA commuter rail to Boston! Conveniently located near local schools, with easy access for families.AI-generated virtual staging. Furniture and decor are digitally added for illustration purposes only.

3 Beds ⋅ 2 Baths ⋅ 73566405 MLS

Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a dining area with sliders to a private deck and fully-fenced, tree-lined yard. Upstairs features three bedrooms, including a impressive primary suite with a stunning walk-in closet, and a full bath. Major upgrades include deleading (2018), basement asbestos removal (2019), a newer furnace, and a brand-new water heater (2024). Ideally located just 1 mile from Winchester Center, top schools, dining, and the MBTA commuter rail to Boston! Conveniently located near local schools, with easy access for families.AI-generated virtual staging. Furniture and decor are digitally added for illustration purposes only.

17 Russell Rd, Winchester

Listing courtesy of Listing Agent: Tsz Mui Kwan from Listing Office: Kwan Realty Inc..

$1,899,000

Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

4 Beds ⋅ 3 Baths ⋅ 73565817 MLS

Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

85 High St, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$2,399,000

Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with custom built-ins and entertaining bar,formal dining with butler’s pantry, private office,and luxurious primary suite with vaulted ceilings, walk-in closets,and spa bath.Expanded outdoor living features a custom outdoor kitchen,fire pit,and multiple patios designed for exceptional entertaining.The finished lower level offers a bonus room, home gym, mudroom, and oversized 2-car garage.Professionally landscaped with exceptional privacy, yet just moments to the Vinson-Owen School,steps to the Swim & Tennis Club,and major commuter routes.A rare opportunity to own one of Winchester’s finest newer homes. See Video: https://player.vimeo.com/progressive_redirect/playback/1217669935/rendition/1080p/file.mp4%20%281080p%29.mp4?loc=external&log_user=0&signature=65fb6c1e2692e9ac8d5b781ceed13c02239d5128d88af87ce725ce6cd7907704

4 Beds ⋅ 5 Baths ⋅ 73555666 MLS

Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with custom built-ins and entertaining bar,formal dining with butler’s pantry, private office,and luxurious primary suite with vaulted ceilings, walk-in closets,and spa bath.Expanded outdoor living features a custom outdoor kitchen,fire pit,and multiple patios designed for exceptional entertaining.The finished lower level offers a bonus room, home gym, mudroom, and oversized 2-car garage.Professionally landscaped with exceptional privacy, yet just moments to the Vinson-Owen School,steps to the Swim & Tennis Club,and major commuter routes.A rare opportunity to own one of Winchester’s finest newer homes. See Video: https://player.vimeo.com/progressive_redirect/playback/1217669935/rendition/1080p/file.mp4%20%281080p%29.mp4?loc=external&log_user=0&signature=65fb6c1e2692e9ac8d5b781ceed13c02239d5128d88af87ce725ce6cd7907704

54 Squire Road, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.

$3,450,000

Situated on a generous18,000SF level lot! Must see this custom built spectacular masterpiece by some of winchester's finest builders, offering unique architectural design and dramatic finishes showcasing a fabulous dining room w/ a custom wine wall cabinet, gorgeous kitchen, with high end 48 inch gas range w/double ovens, 48"paneled fridge, 10' island w/ seating & a walk in pantry! Enter from the oversized three car garage into the stunning mudroom & into the most fabulous home that has hit the market in quite some time. Wide plank oak flooring, high ceilings & tasteful finishes throughout. The family room feature wall has custom arched inset bookshelves & cabinetry with led lighting, gas fireplace & plenty of windows to enjoy views of the gorgeous yard. Enjoy conversations & cocktails in the stylish lounge featuring elegant arched details, a custom wet bar & wine fridge. Oversized sliders to spacious deck draw you to the gorgeous 1/2 acre level lot with **room for pool ** pool shown is virtual image*. The first floor also offers a bedroom or home office option; The second floor features 5 large bedrooms & 3 full baths w/ soaring ceilings in every room; the primary being a dreamy retreat showcasing a spa like porcelain bath w 10' shower & 2 shower heads with soaking tub, bidet toilet & walk in closet! Second floor laundry w/sink & custom cabinetry make doing laundry a joy. The lower level offers plenty of space for media room, game room plus space for a home gym & full bath! This exceptional home is a must see ~the top quality finishes and stunning design will not disappoint!

6 Beds ⋅ 5 Baths ⋅ 73561703 MLS

Situated on a generous18,000SF level lot! Must see this custom built spectacular masterpiece by some of winchester's finest builders, offering unique architectural design and dramatic finishes showcasing a fabulous dining room w/ a custom wine wall cabinet, gorgeous kitchen, with high end 48 inch gas range w/double ovens, 48"paneled fridge, 10' island w/ seating & a walk in pantry! Enter from the oversized three car garage into the stunning mudroom & into the most fabulous home that has hit the market in quite some time. Wide plank oak flooring, high ceilings & tasteful finishes throughout. The family room feature wall has custom arched inset bookshelves & cabinetry with led lighting, gas fireplace & plenty of windows to enjoy views of the gorgeous yard. Enjoy conversations & cocktails in the stylish lounge featuring elegant arched details, a custom wet bar & wine fridge. Oversized sliders to spacious deck draw you to the gorgeous 1/2 acre level lot with **room for pool ** pool shown is virtual image*. The first floor also offers a bedroom or home office option; The second floor features 5 large bedrooms & 3 full baths w/ soaring ceilings in every room; the primary being a dreamy retreat showcasing a spa like porcelain bath w 10' shower & 2 shower heads with soaking tub, bidet toilet & walk in closet! Second floor laundry w/sink & custom cabinetry make doing laundry a joy. The lower level offers plenty of space for media room, game room plus space for a home gym & full bath! This exceptional home is a must see ~the top quality finishes and stunning design will not disappoint!

7 Hutchinson Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$3,600,000

Spectacular ground-up NEW construction set on an expansive, level lot of 24,688 square foot lot at the end of a quiet Winchester cul-de-sac. Newly completed and ready for immediate occupancy, this exceptional residence offers more than 7,000 square feet of beautifully finished living space, combining impressive scale, refined design, privacy and convenience just moments from Winchester Country Club. Designed with entertaining in mind, the residence features seven spacious bedrooms and 7.5 designer baths, providing beautifully appointed private retreats for family and guests. At the heart of the home is a chef’s kitchen, thoughtfully designed with custom cabinetry, generous preparation and gathering spaces, and an impressive suite of appliances including a 48" Wolf gas stove, Sub-Zero fridge, double ovens, 2 Bosch dishwashers. steam oven, built in microwave and wine fridge. The kitchen flows seamlessly into expansive, light-filled lamily, living and dining spaces, creating an inviting setting for large gatherings, celebrations, and relaxed everyday living. The flexible floor plan is perfectly suited to today’s lifestyle, with dedicated spaces for a professional home office, private fitness studio, and expansive recreation area. Set on more than half an acre of private grounds, the property also features a three-car garage, and excellent potential for a future pool and exceptional outdoor entertaining spaces. A rare opportunity to own a substantial, newly built home in an ideal Winchester setting, conveniently located near the town center, dining, schools, recreational amenities, hiking trails, Winchester Country Club and Wright Locke Farm.

7 Beds ⋅ 8 Baths ⋅ 73556474 MLS

Spectacular ground-up NEW construction set on an expansive, level lot of 24,688 square foot lot at the end of a quiet Winchester cul-de-sac. Newly completed and ready for immediate occupancy, this exceptional residence offers more than 7,000 square feet of beautifully finished living space, combining impressive scale, refined design, privacy and convenience just moments from Winchester Country Club. Designed with entertaining in mind, the residence features seven spacious bedrooms and 7.5 designer baths, providing beautifully appointed private retreats for family and guests. At the heart of the home is a chef’s kitchen, thoughtfully designed with custom cabinetry, generous preparation and gathering spaces, and an impressive suite of appliances including a 48" Wolf gas stove, Sub-Zero fridge, double ovens, 2 Bosch dishwashers. steam oven, built in microwave and wine fridge. The kitchen flows seamlessly into expansive, light-filled lamily, living and dining spaces, creating an inviting setting for large gatherings, celebrations, and relaxed everyday living. The flexible floor plan is perfectly suited to today’s lifestyle, with dedicated spaces for a professional home office, private fitness studio, and expansive recreation area. Set on more than half an acre of private grounds, the property also features a three-car garage, and excellent potential for a future pool and exceptional outdoor entertaining spaces. A rare opportunity to own a substantial, newly built home in an ideal Winchester setting, conveniently located near the town center, dining, schools, recreational amenities, hiking trails, Winchester Country Club and Wright Locke Farm.

11 Viking Road, Winchester

Listing courtesy of Listing Agent: Post Advisory Group from Listing Office: Engel & Volkers Boston.

$799,000

Walkable to nearly everything, 15 Clark St presents and exceptional opportunity to enjoy refined living in one of Winchester's sought-after neighborhoods. This sun-drenched duplex offers 3 bedrooms, 1.5 bathrooms, and approx 1,336 sq ft of thoughtfully curated living space. Rich hardwood and pine floors, soaring natural light, and an effortless flow in layout create a warm and sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester commuter rail, and major routes, this home embodies the very best of Winchester living.

3 Beds ⋅ 2 Baths ⋅ 73555218 MLS

Walkable to nearly everything, 15 Clark St presents and exceptional opportunity to enjoy refined living in one of Winchester's sought-after neighborhoods. This sun-drenched duplex offers 3 bedrooms, 1.5 bathrooms, and approx 1,336 sq ft of thoughtfully curated living space. Rich hardwood and pine floors, soaring natural light, and an effortless flow in layout create a warm and sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester commuter rail, and major routes, this home embodies the very best of Winchester living.

15 Clark St, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.

$899,000

Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds convenience and additional storage, and a half bath is located in the unfinished basement. Just 1 mile from Winchester Center, enjoy easy access to restaurants, coffee shops, boutiques, the public library, and commuter options with close proximity to Boston. The recently built elementary school and renovated high school feature state-of-the-art facilities. Nearby Horn Pond offers scenic walking trails, kayaking, birdwatching, and waterfront views.

3 Beds ⋅ 2 Baths ⋅ 73549935 MLS

Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds convenience and additional storage, and a half bath is located in the unfinished basement. Just 1 mile from Winchester Center, enjoy easy access to restaurants, coffee shops, boutiques, the public library, and commuter options with close proximity to Boston. The recently built elementary school and renovated high school feature state-of-the-art facilities. Nearby Horn Pond offers scenic walking trails, kayaking, birdwatching, and waterfront views.

47 Water Street, Winchester

Listing courtesy of Listing Agent: The Mary Scimemi Team from Listing Office: Leading Edge Real Estate.

$1,870,000

Space where you need it, flexibility where you want it. This extensively renovated 5-bedroom Colonial offers a rare combination of a first-floor bedroom, two upstairs suites, finished lower level, attached 2-car garage, and nearly 1/3 acre, all just minutes from Winchester Center. Sophisticated and comfortable, the home features beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level offers hardwood floors and thoughtful architectural details, with a spacious eat-in kitchen featuring an island, abundant prep space, and seamless access to the patio and private backyard. A formal dining room, oversized fireplaced living room, mudroom, half bath, and first-floor bedroom provide exceptional flexibility. Upstairs are two impressive suites with cathedral ceilings, walk-in closets, and private baths, along with two additional bedrooms, a full bath, and laundry. The finished lower level offers a spacious family room with fireplace and ample storage. An attached 2-car garage completes this exceptional home, conveniently located near Winchester Center’s shops, restaurants, commuter rail, and major routes.

5 Beds ⋅ 4 Baths ⋅ 73545952 MLS

Space where you need it, flexibility where you want it. This extensively renovated 5-bedroom Colonial offers a rare combination of a first-floor bedroom, two upstairs suites, finished lower level, attached 2-car garage, and nearly 1/3 acre, all just minutes from Winchester Center. Sophisticated and comfortable, the home features beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level offers hardwood floors and thoughtful architectural details, with a spacious eat-in kitchen featuring an island, abundant prep space, and seamless access to the patio and private backyard. A formal dining room, oversized fireplaced living room, mudroom, half bath, and first-floor bedroom provide exceptional flexibility. Upstairs are two impressive suites with cathedral ceilings, walk-in closets, and private baths, along with two additional bedrooms, a full bath, and laundry. The finished lower level offers a spacious family room with fireplace and ample storage. An attached 2-car garage completes this exceptional home, conveniently located near Winchester Center’s shops, restaurants, commuter rail, and major routes.

79 Grove St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.

$2,250,000

Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for year-round comfort, the home features central AC, central humidification, and an air exchanger. Outside, enjoy beautifully landscaped gardens, a spacious deck overlooking the private yard, lush irrigated grounds with an invisible dog fence, and a hot tub for unwinding after a long day. A wood-burning fireplace adds warmth and character to the living space. Located just minutes from top-rated schools, Winchester Center, and convenient commuter access to Boston, this is a rare opportunity to enjoy privacy, nature, and timeless New England living in an exceptional location.

5 Beds ⋅ 3 Baths ⋅ 73544924 MLS

Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for year-round comfort, the home features central AC, central humidification, and an air exchanger. Outside, enjoy beautifully landscaped gardens, a spacious deck overlooking the private yard, lush irrigated grounds with an invisible dog fence, and a hot tub for unwinding after a long day. A wood-burning fireplace adds warmth and character to the living space. Located just minutes from top-rated schools, Winchester Center, and convenient commuter access to Boston, this is a rare opportunity to enjoy privacy, nature, and timeless New England living in an exceptional location.

9 Plymouth Rd, Winchester

Listing courtesy of Listing Agent: Steph Crawford Group from Listing Office: Real Broker MA, LLC.

$1,350,000

Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The home offers exceptional curb appeal and privacy with mature evergreens, specialty trees, and an elevated setting. Inside, a central staircase creates a focal point while naturally defining the open concept living and dining rooms, perfect for everyday living and entertaining. The living room is full of natural light, with a large bay of windows and seamlessly connects with the dining room featuring classic wainscoting, and a decorative fireplace. The spacious, thoughtfully updated kitchen offers granite countertops, SS appliances, a breakfast bar island, and laundry. A convenient side entry provides direct access to the first of two driveways, the deck, and the large, private backyard beyond. The deck overlooks a fully fenced backyard that offers the perfect setting for relaxation, recreation, and entertaining. The flexible floor plan is designed to fit a variety of needs with a versatile main level bedroom, a sunny and cheerful space with hardwood floors and direct access to the first of three full bathrooms. The bathroom, also accessible from the hall, offers a dual sink vanity and tiled tub with a shower. A convenient laundry area adds the finishing touch to the main level. Designed with comfort and functionality in mind, the second level features a private primary suite, two additional bedrooms, a family room, and a full family bathroom, all connected by a wide central hallway. The primary bedroom offers a large walk-in closet and an updated bathroom featuring a dual sink vanity and a beautifully tiled shower. The family bedrooms are full of natural light with hardwood floors and ample closets, sharing the family bathroom with a tub and shower. One of the bedrooms also works well as an office if needed. Double French doors open to the inviting family room, where cozy carpeting and a large window overlooking the backyard create the perfect space to relax. Set on a large corner lot with two driveways and a detached two-car garage accessed from quiet Englewood Road, this special property offers a prime location just moments from the Middlesex Fells Reservation, the town center, the commuter rail and Muraco ES. Nothing left to do but move right in.

4 Beds ⋅ 3 Baths ⋅ 73541775 MLS

Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The home offers exceptional curb appeal and privacy with mature evergreens, specialty trees, and an elevated setting. Inside, a central staircase creates a focal point while naturally defining the open concept living and dining rooms, perfect for everyday living and entertaining. The living room is full of natural light, with a large bay of windows and seamlessly connects with the dining room featuring classic wainscoting, and a decorative fireplace. The spacious, thoughtfully updated kitchen offers granite countertops, SS appliances, a breakfast bar island, and laundry. A convenient side entry provides direct access to the first of two driveways, the deck, and the large, private backyard beyond. The deck overlooks a fully fenced backyard that offers the perfect setting for relaxation, recreation, and entertaining. The flexible floor plan is designed to fit a variety of needs with a versatile main level bedroom, a sunny and cheerful space with hardwood floors and direct access to the first of three full bathrooms. The bathroom, also accessible from the hall, offers a dual sink vanity and tiled tub with a shower. A convenient laundry area adds the finishing touch to the main level. Designed with comfort and functionality in mind, the second level features a private primary suite, two additional bedrooms, a family room, and a full family bathroom, all connected by a wide central hallway. The primary bedroom offers a large walk-in closet and an updated bathroom featuring a dual sink vanity and a beautifully tiled shower. The family bedrooms are full of natural light with hardwood floors and ample closets, sharing the family bathroom with a tub and shower. One of the bedrooms also works well as an office if needed. Double French doors open to the inviting family room, where cozy carpeting and a large window overlooking the backyard create the perfect space to relax. Set on a large corner lot with two driveways and a detached two-car garage accessed from quiet Englewood Road, this special property offers a prime location just moments from the Middlesex Fells Reservation, the town center, the commuter rail and Muraco ES. Nothing left to do but move right in.

423 Washington St, Winchester

Listing courtesy of Listing Agent: Danielle Fleming from Listing Office: MA Properties.

$1,025,000

GREAT PRICE!!! Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!

3 Beds ⋅ 3 Baths ⋅ 73519082 MLS

GREAT PRICE!!! Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!

53 Lake Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$2,100,000

Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves as the anchor for the expansive living and dining areas. The primary sanctuary is a true showstopper, featuring soaring ceilings and a boutique-style walk-in closet of legendary proportions. With six bedrooms and spa-inspired baths, there is plenty of space for multiple uses and configurations. From the lower-level recreation room with patio access to the proximity to Wedge Pond and the Middlesex Fells, this home is designed for indoor and outdoor leisure. Enjoy the convenience of nearby local shopping and easy access to the surrounding areas.

6 Beds ⋅ 5 Baths ⋅ 73510713 MLS

Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves as the anchor for the expansive living and dining areas. The primary sanctuary is a true showstopper, featuring soaring ceilings and a boutique-style walk-in closet of legendary proportions. With six bedrooms and spa-inspired baths, there is plenty of space for multiple uses and configurations. From the lower-level recreation room with patio access to the proximity to Wedge Pond and the Middlesex Fells, this home is designed for indoor and outdoor leisure. Enjoy the convenience of nearby local shopping and easy access to the surrounding areas.

6 Ivy Circle, Winchester

Listing courtesy of Listing Agent: Post Advisory Group from Listing Office: Engel & Volkers Boston.

$2,799,000

Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England Colonial style. Curved front stair case add one more layer of beauty. Second floor and third floor offer total 6 bedrooms, suites and walk-in closets. Master bedroom is with cathedral ceilings, a sprawling master closet and an office/sitting area. Smooth flow of the spacious and walk out lower level enables rich life style with billiard room, media room, art room and exercise room -- all designed for a modern lifestyle, with an open layout that is perfect for entertaining. State of the art systems with total 6 heating and cooling zones and central vacuum system.

6 Beds ⋅ 7 Baths ⋅ 73500890 MLS

Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England Colonial style. Curved front stair case add one more layer of beauty. Second floor and third floor offer total 6 bedrooms, suites and walk-in closets. Master bedroom is with cathedral ceilings, a sprawling master closet and an office/sitting area. Smooth flow of the spacious and walk out lower level enables rich life style with billiard room, media room, art room and exercise room -- all designed for a modern lifestyle, with an open layout that is perfect for entertaining. State of the art systems with total 6 heating and cooling zones and central vacuum system.

14 Nassau Drive, Winchester

Listing courtesy of Listing Agent: Weidong Li from Listing Office: WINN Real Estate & Consulting.