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15 Vinson Circle, Winchester
$18,000,000
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.
4 Dartmouth, Winchester
$4,299,000
5 Beds ⋅ 6 Baths ⋅ 73574948 MLS
Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully renovated, maintained and updated, blending classic architecture with modern comfort. This 5-bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and relaxed daily living. Water views serve as a serene backdrop to the large modern kitchen, where the natural light dapples and shines all day. It's what everyone craves: the bright, sunny, warm inviting hub of the home. There is an attached mudroom with custom lockers/cabinets, and radiant heat floors. A large family room is attached and is highlighted by a gas-burning fireplace. The expansive living and dining rooms offer plenty of space for more formal entertaining and big groups. One of our favorite features is the study, tucked off the living room and connected to a divine screened-in porch. The natural woodwork and handsome architecture harken to yesteryear while providing the perfect home office and a place to unwind when done working. A generous primary suite is a private retreat with a spacious bath and ample walk-in closets. There are 4 other ample bedrooms, 3 of which are connected to baths, and a second-floor laundry complete this floor. The basement has a huge media and game room, sauna, gym, wine cellar and direct access through a mudroom to a covered patio. Several curated outdoor dining and gathering areas invite entertaining, sunset dinners or quiet reading, overlooking the pond. There is also a full walk-up attic with great ceiling height, unfinished and waiting for your inspiration. An oversized two-car garage with soaring ceilings complete the must-haves. Kayak, skate, go fishing and enjoy life on the water in one of Winchester's most prized, quiet neighborhoods!

4 Dartmouth, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
724 Main St, Winchester
$4,000,000
73582018 MLS
Exceptional opportunity to own or lease a beautifully renovated, meticulously maintained mixed-use property with exciting development potential just outside Winchester Center! Offering approximately 7,010 sq. ft. across four levels, this versatile building offers expansion potential & features a flexible layout with numerous private offices, conference and meeting spaces, open work areas & multiple restrooms ideal for a variety of professional, office or mixed-use possibilities. Additional highlights include 19 parking spaces, a direct-access garage and beautiful Wedge pond views. The generous floor plan can accommodate a single occupant, multiple businesses or teams, while the property’s mixed-use zoning offers potential for residential redevelopment. Conveniently located close to Winchester Center with access to the bus line right outside the door & easy access to the commuter rail, schools, restaurants, coffee shops, shopping, banks and downtown amenities. A rare opportunity to purchase, lease or explore the property’s development potential in a highly desirable Winchester location! Call for additional info/ brochure!

724 Main St, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
11 Viking Road, Winchester
$3,600,000
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.
7 Hutchinson Road, Winchester
$3,450,000
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.
1 Plymouth Rd., Winchester
$3,299,000
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.
30 Willowdale Rd, Winchester
$3,200,000
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.
18 Ridge St, Winchester
$3,200,000
5 Beds ⋅ 6 Baths ⋅ 73561372 MLS
Introducing 18 Ridge Street — a masterfully restored and reimagined Greek Revival residence where timeless architectural beauty meets elevated modern luxury. Set on a beautifully landscaped 20,654 sq ft lot, this exceptional 5-bedroom, 5 full and 1 half bath home offers over 5,295 square feet of exquisitely curated living space designed for both sophisticated entertaining and everyday comfort. From the moment you arrive, the home’s striking historical columns, wraparound porch, circular driveway, and natural stone detailing create an unforgettable first impression. Inside, every space has been thoughtfully crafted with premium finishes and custom design elements throughout. The showstopping chef’s kitchen features paneled Thermador appliances, a stunning La Cornue induction range, and a custom white oak island that seamlessly anchors the heart of the home. Formal and informal living spaces flow beautifully together, highlighted by exposed chimneys, restored 1800s double doors, multiple fireplaces, floor-to-ceiling windows, and rich hardwood flooring. The luxurious primary suite serves as a private retreat, complete with a tray ceiling, fireplace, spa-inspired bath with radiant heated floors, soaking tub, oversized custom shower, and an impressive walk-in closet with built-in island storage. Additional bedrooms offer ensuite and Jack-and-Jill bath configurations, while the finished third floor provides flexible living with cathedral ceilings, sitting area, and office space.Designed with entertainment and lifestyle in mind, the finished lower level features a custom movie theater, wet bar, wine room, and additional pantry storage. Above the detached two-car garage, finished bonus rooms with a full bath create the ideal space for a home office, gym, studio, or guest accommodations.Blending historic character with cutting-edge efficiency, the home has undergone an extensive structural rebuild and offers fully electric, energy-efficient living with multi-zone heat pumps, EV-ready garage spaces, radiant heated bathroom floors, Pella windows, and premium construction materials throughout. A rare opportunity to own a truly distinctive luxury residence in one of Winchester’s most sought-after neighborhoods.

18 Ridge St, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.
9 Albamont Road, Winchester
$3,200,000
6 Beds ⋅ 6 Baths ⋅ 73482275 MLS
Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer kitchen w/vaulted ceilings, skylights, oversized island, sliders to large deck & a fire-placed family room, along with formal living and dining rooms & a FIRST FLOOR bedroom suite! The 2nd floor offers 4 generous BR's including a luxurious primary suite, 2 additional full baths & convenient second floor laundry. The above grade/ walk-out lower level adds exceptional flexibility w/ *Au- pair or In-law suite* media room, home office, exercise room, bedroom & full bath Enjoy all the area has to offer including restaurants, shops, schools, train to Boston, Bike-paths & more! 7 miles from Boston

9 Albamont Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
37 Mayflower Road, Winchester
$3,149,000
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.
8 Priscilla Lane, Winchester
$2,995,000
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.
14 Nassau Drive, Winchester
$2,799,000
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.
18 Middlesex St, Winchester
$2,695,000
4 Beds ⋅ 5 Baths ⋅ 73518621 MLS
Seller to offer a buyer credit paying up to 2% of loan size for buyer at closing that can go to a permanent or temporary rate buydown. European inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the home is a designer chef’s kitchen w/ bespoke cabinetry, lux appliances, and an adjoining mudroom. Outside, the property transforms into a private resort-like retreat with granite-columned loggia, heated saltwater pool, landscaped grounds w/ irrigation, and multiple entertaining areas. The spa-like primary suite, ensuite guest bedrooms, finished lower level with flexible bonus spaces, and heated driveway/walkways complete this estate.

18 Middlesex St, Winchester

Listing courtesy of Listing Agent: Tina Natale from Listing Office: Luxury Living Real Estate.
7 Lakeview Terrace, Winchester
$2,600,000
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.
63 Wedgemere Avenue, Winchester
$2,399,000
4 Beds ⋅ 4 Baths ⋅ 73587441 MLS
Stately and beautifully built brick Colonial in a premier Flats location, set on a gorgeous, level corner lot just under half an acre. Gracious proportions, soaring ceilings, hardwood floors, beautiful moldings, and exceptional architectural detail are showcased throughout all three levels. The welcoming first floor features a front-to-back living room with fireplace, generously sized dining room, spacious kitchen with center island and eat-in area, study, half bath, sun porch, and convenient first-floor laundry. Upstairs are four large bedrooms, including a spacious primary suite with private ensuite bath, plus a full family bathroom. The finished lower level offers even more living space with hardwood floors, a family room with fireplace, half bath, and bonus room, perfect for a playroom, gym, or home office. Two-car garage, central air, newer heating system, newer roof, and ample storage add to the home's comfort and convenience. A wonderful opportunity to own a substantial and elegant home in one of Winchester's most coveted neighborhoods.

63 Wedgemere Avenue, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
54 Squire Road, Winchester
$2,399,000
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.
9 Plymouth Rd, Winchester
$2,250,000
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.
42 Everett Ave, Winchester
$2,199,000
6 Beds ⋅ 5 Baths ⋅ 73588192 MLS
This distinguished residence on one of Winchester's most notable streets is a celebration of grand proportions, exquisite period craftsmanship, and timeless architectural beauty. High ceilings, four fireplaces, original hardwood floors, and beautifully scaled rooms create a sense of elegance that is increasingly difficult to find. The grand dining room is full of original details, anchored by a large fireplace and a big picture window that fills the room with natural light. A gracious living room offers another fireplace, beautiful hardwood floors, and impressive ceiling height, providing an elegant setting equally suited to intimate evenings and large-scale entertaining. A handsome first-floor study and south-facing sunroom offer quieter retreats, while the original butler’s pantry, complete with its own marble sink and original cabinets, speaks to the home’s history and the gracious way in which it was designed to be lived in. Six bedrooms + three full baths provide exceptional flexibility across the upper levels, with generous proportions and architectural details continuing throughout the home. Bonus space on the top floor and in the partially-finished basement provides room for a second home office, media room, gym or in-law space. The large patio offers privacy and entertaining space, while the grassy backyard has ample room to play. A rare three-story garage, originally designed with both chauffeur's quarters and a greenhouse, presents intriguing possibilities for the next owner. Set along prestigious Everett Avenue, in the Ambrose School District, it's a quick stroll to the town center, bus to Alewife, or Wedgemere Train Station. This residence offers an opportunity to become the next steward of a home whose craftsmanship, scale, and character simply cannot be replicated today.

42 Everett Ave, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
19 Hancock Street, Winchester
$2,199,000
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.
276 High Street, Winchester
$2,195,000
5 Beds ⋅ 4 Baths ⋅ 73496396 MLS
Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!

276 High Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
6 Ivy Circle, Winchester
$2,100,000
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.
21 Amberwood Dr, Winchester
$2,049,000
5 Beds ⋅ 4 Baths ⋅ 73588059 MLS
Welcome to this beautifully appointed and exceptionally spacious home, ideally situated in a quiet, desirable West Side Winchester neighborhood within the sought-after Vinson-Owen School district. Offering an impressive combination of elegant living spaces, flexible accommodations, and thoughtful upgrades, this home provides room for everyone while easily adapting to a variety of lifestyles. At the heart of the home is the expansive granite kitchen, designed for both everyday living and entertaining. Custom cabinetry, Thermador double ovens, a Dacor warming drawer, Sub-Zero refrigerator, wine refrigerator, recessed lighting, and an impressive 50-square-foot center island create a wonderful gathering space with plenty of room for cooking, dining, and entertaining. The kitchen flows into a comfortable family room featuring a custom-built entertainment center and electric fireplace. A gracious formal dining room showcases handcrafted molding and classic wainscoting, while additional first-floor living spaces provide tremendous flexibility for a formal living room, playroom, home office, den, or whatever best suits your needs.One of the home's most appealing features is the first-floor bedroom suite with a full bath, offering exceptional versatility for extended family, guests, an au pair, or anyone seeking the convenience of first-floor living. A dedicated laundry room on this level adds even more functionality. With multiple living areas and flexible rooms throughout the first floor, there are countless ways to create private spaces for additional family members while still enjoying plenty of room to gather together.Upstairs, the generously sized primary suite provides a relaxing retreat with vaulted ceilings, recessed lighting, double closets, and a beautifully tiled private bath with double sinks. Three additional spacious bedrooms, another full bath, and additional office space provide abundant room for family, guests, work-from-home needs, hobbies, or study areas.With its generous proportions, flexible floor plan, multiple bedroom and living configurations, and outstanding West Side location, this is a home designed to grow and change with its owners. Enjoy the peace and privacy of a quiet neighborhood while being part of the wonderful Winchester community. This is more than simply a beautiful house—it is a home offering the space, versatility, and comfort today's buyers are looking for.

21 Amberwood Dr, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.
7 Wainwright Road Unit 113, Winchester
$1,999,000
4 Beds ⋅ 4 Baths ⋅ 73556476 MLS ⋅ ['The Ledges'] BLDG.
Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home offers an elegant first-floor primary suite w/ dual walk-in closets and a stunning spa-inspired bath. Meticulously reimagined from top to bottom, every element of this extraordinary renovation was thoughtfully curated using the finest imported designer finishes and bespoke craftsmanship, creating an unparalleled level of luxury. The dramatic open-concept main level is highlighted by soaring vaulted ceilings, a fireplaced living room w/ a custom-designed mantel, & walls of glass that open to a private deck overlooking breathtaking western sunsets & tranquil natural surroundings. The designer kitchen is a true showpiece, featuring premium finishes, a sun-filled breakfast area, & seamless flow into the elegant dining room, ideal for both intimate gatherings & entertaining.The second floor offers 3 rooms including a spacious bedroom, beautifully renovated full bath, loft ideal for a home office, & an additional sitting room/TV room or guest space. The walk-out lower level it’s another suite in itself offering a spacious family room, second kitchenette, dining area, game room, additional bedroom with double closets, a luxurious spa bath, oversized laundry room, and abundant storage. Step outside to a private patio surrounded by peaceful, picturesque grounds, creating the perfect retreat for relaxing or entertaining. Ideally located w/ easy access to Winchester Center, Whole Foods, major highways, restaurants, and shops, this exceptional home offers luxury living just 7 miles from downtown Boston.

7 Wainwright Road Unit 113, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
26 Mayflower Road, Winchester
$1,950,000
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..
85 High St, Winchester
$1,899,000
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.
79 Grove St, Winchester
$1,870,000
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.
1 Overlook Way, Winchester
$1,850,000
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.
17 Churchill Rd, Winchester
$1,749,000
5 Beds ⋅ 4 Baths ⋅ 73572890 MLS
A rare offering in one of Winchester's most desirable neighborhoods, this spacious mid-century contemporary spans approximately 3,500 square feet with 5 bedrooms and 3.5 baths on a private 0.24-acre lot. The open main level flows from a light-filled living room with a cathedral ceiling, stained-glass accents, and a fireplace into the dining room, family room, and a renovated kitchen with Silestone quartz countertops, upgraded cabinetry, and direct deck access. Upstairs, two ensuite bedrooms anchor the floor plan, including a generous primary suite with a large jetted soaking tub, vanity, and walk-in closet. Three additional bedrooms and a family bath complete the level. Hardwood floors run throughout, a second fireplace warms the lower-level bonus room, and ductless mini-splits deliver year-round comfort throughout the house. The walk-out lower level offers a versatile bonus room with its own exterior entrance, ideal for a home office, gym, media room, playroom, or guest suite. Three decks extend the living space outdoors for entertaining and dining above the private backyard, and an attached two-car garage adds everyday ease. Set on a quiet street with easy access to commuter rail, downtown Winchester, parks, and bike or jog trails, this is a rare chance to live in your dream home in a community that has it all.

17 Churchill Rd, Winchester

Listing courtesy of Listing Agent: Domingo Medina from Listing Office: Coldwell Banker Realty - Lexington.
1 Town Way, Winchester
$1,749,000
3 Beds ⋅ 4 Baths ⋅ 73555777 MLS
Welcome home to this beautifully renovated gem, perfectly positioned on a corner lot in the highly sought-after LINCOLN ELEMENTARY SCHOOL district! Warm, inviting, and truly move-in ready, this home offers the open-concept first floor today’s buyers are looking for—featuring a stunning kitchen that flows effortlessly into the dining and living areas, plus a sunken family room ideal for relaxing or entertaining. Step outside to enjoy the beautifully fenced-in yard, offering a private outdoor retreat for play, pets, gardening, or gatherings. Everyday convenience continues with a mudroom located directly off the driveway, multiple off-street parking spaces, and a two-car garage. The finished lower level includes a full bathroom and versatile flex space perfect for a recreation room, home gym, playroom, or media room. Upstairs, you’ll find three bedrooms, including a lovely primary suite with a spacious bedroom, walk-in closet, and full bath. Thoughtfully renovated from top to bottom, this home features all new systems for peace of mind and effortless modern living. Located just a short walk to Winchester’s vibrant town center and commuter rail.

1 Town Way, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
117 Highland, Winchester
$1,650,000
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.

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