viewhomesingreaterboston.com Search Results

The buyer got cold feet. Tucked away on a picturesque street, this beautifully maintained Colonial offers 4 levels of thoughtfully designed living space. The open-concept main floor features a sun-filled living room with vaulted ceilings, skylights, gas fireplace, and an adjacent dining area. The gourmet kitchen boasts stainless steel appliances, breakfast bar, built-in desk, and sliders leading to a private deck. A formal dining room, family/playroom, and half bath complete the first level.The second floor includes a spacious primary suite with ensuite bath, two additional bedrooms, full bath, laundry, generous closet space, and sunset views. The third floor offers two additional bedrooms and a full bath-ideal for guests, offices, or extended family.The finished lower level includes a yoga room, large recreation room, and direct exterior access to a fenced backyard with patio and hot tub.New heating and water heater. Close to downtown Winchester, schools and transportation.

5 Beds ⋅ 5 Baths ⋅ 73429273 MLS

The buyer got cold feet. Tucked away on a picturesque street, this beautifully maintained Colonial offers 4 levels of thoughtfully designed living space. The open-concept main floor features a sun-filled living room with vaulted ceilings, skylights, gas fireplace, and an adjacent dining area. The gourmet kitchen boasts stainless steel appliances, breakfast bar, built-in desk, and sliders leading to a private deck. A formal dining room, family/playroom, and half bath complete the first level.The second floor includes a spacious primary suite with ensuite bath, two additional bedrooms, full bath, laundry, generous closet space, and sunset views. The third floor offers two additional bedrooms and a full bath-ideal for guests, offices, or extended family.The finished lower level includes a yoga room, large recreation room, and direct exterior access to a fenced backyard with patio and hot tub.New heating and water heater. Close to downtown Winchester, schools and transportation.

166 Forest St, Winchester

Listing courtesy of Listing Agent: Ning Sun from Listing Office: United Real Estate, LLC.

$1,607,000

Location, location, location! Enjoy one-level living in this charming Ranch-style home, beautifully situated on a cul-de-sac, within walking distance to the vibrant Town Center. This exceptional property, lovingly maintained by the same owners for 50+ years, offers a large fireplaced living room with ample natural light, gracious dining room with built-in cabinets, tasteful new kitchen with quartz countertops and stainless appliances (2025), spacious primary bedroom with en-suite bath and cedar closet, 3 additional good-sized bedrooms, beautiful hardwood floors, central airconditioning, sunroom overlooking private backyard, mudroom, abundant storage space, and more. Bring your creative ideas for the large space in the lower level to personalize for your needs. The 2-car garage, motion-sensor lights, and the landscaped yard complete the picture. Welcome to Winchester with its highly rated schools, two commuter rail stations, Mystic Lakes, and the much-treasured Fells Reservation.

4 Beds ⋅ 3 Baths ⋅ 73505351 MLS

Location, location, location! Enjoy one-level living in this charming Ranch-style home, beautifully situated on a cul-de-sac, within walking distance to the vibrant Town Center. This exceptional property, lovingly maintained by the same owners for 50+ years, offers a large fireplaced living room with ample natural light, gracious dining room with built-in cabinets, tasteful new kitchen with quartz countertops and stainless appliances (2025), spacious primary bedroom with en-suite bath and cedar closet, 3 additional good-sized bedrooms, beautiful hardwood floors, central airconditioning, sunroom overlooking private backyard, mudroom, abundant storage space, and more. Bring your creative ideas for the large space in the lower level to personalize for your needs. The 2-car garage, motion-sensor lights, and the landscaped yard complete the picture. Welcome to Winchester with its highly rated schools, two commuter rail stations, Mystic Lakes, and the much-treasured Fells Reservation.

6 Oakland Circle, Winchester

Listing courtesy of Listing Agent: Seeme Moreira from Listing Office: Coldwell Banker Realty - Lexington.

$1,600,000

Rare Opportunity: Spacious Side-by-Side Two-Family Home Less Than 1 Mile from Town Center. This charming two-family home offers classic period details, including fireplaced living rooms, formal dining rooms with built-in china cabinets located directly off the kitchen. Each unit features two large bedrooms with hardwood floors and a full bath on the second floor, plus two additional bedrooms and storage on the third floor. Both units have separate, spacious basements with tall ceilings and separate utilities. Great yard space, two-car garage and driveway located off Glen Rd. Located less than 3/4 mile from the town center, this property is ideal for both investors and owner-occupants. Don’t miss this exceptional opportunity! Open House Saturday 9/20, 12-1:30pm & Sunday 9/21, 1:30-3pm

8 Beds ⋅ 3 Baths ⋅ 73433062 MLS

Rare Opportunity: Spacious Side-by-Side Two-Family Home Less Than 1 Mile from Town Center. This charming two-family home offers classic period details, including fireplaced living rooms, formal dining rooms with built-in china cabinets located directly off the kitchen. Each unit features two large bedrooms with hardwood floors and a full bath on the second floor, plus two additional bedrooms and storage on the third floor. Both units have separate, spacious basements with tall ceilings and separate utilities. Great yard space, two-car garage and driveway located off Glen Rd. Located less than 3/4 mile from the town center, this property is ideal for both investors and owner-occupants. Don’t miss this exceptional opportunity! Open House Saturday 9/20, 12-1:30pm & Sunday 9/21, 1:30-3pm

112 Church St, Winchester

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

$1,600,000

Come see this spacious 5-bedroom home offered at a NEW PRICE of $1,769,000! Located near the end of a quiet cul-de-sac in a wonderful neighborhood, this home offers privacy, space and natural beauty, just a short distance to Winchester Center and surrounding towns. Walking distance to the Vinson-Owen school, which has consistently been rated as one of the best elementary schools in the state. Set on an 18,000 sq ft lot that backs up to a wooded conservation area with walking trails. All 5 bedrooms and 3 full baths are situated on the second floor, including a cathedral-ceiling primary bedroom/bath with skylights and a steam shower. The main level features an office/den/potential guest room, a large living room/dining room combination leading to a screened-in porch overlooking serene woodlands, a half bath, a bright kitchen with lots of storage and water filtration system. The spacious walk-out lower level provides plenty of room for a playroom/family room/gym and has great storage.

5 Beds ⋅ 4 Baths ⋅ 73362881 MLS

Come see this spacious 5-bedroom home offered at a NEW PRICE of $1,769,000! Located near the end of a quiet cul-de-sac in a wonderful neighborhood, this home offers privacy, space and natural beauty, just a short distance to Winchester Center and surrounding towns. Walking distance to the Vinson-Owen school, which has consistently been rated as one of the best elementary schools in the state. Set on an 18,000 sq ft lot that backs up to a wooded conservation area with walking trails. All 5 bedrooms and 3 full baths are situated on the second floor, including a cathedral-ceiling primary bedroom/bath with skylights and a steam shower. The main level features an office/den/potential guest room, a large living room/dining room combination leading to a screened-in porch overlooking serene woodlands, a half bath, a bright kitchen with lots of storage and water filtration system. The spacious walk-out lower level provides plenty of room for a playroom/family room/gym and has great storage.

10 Olde Lyme Road, Winchester

Listing courtesy of Listing Agent: Darryl E. Brian from Listing Office: RE/MAX Bentley's.

$1,580,000

Welcome to 10 Trinity Road, an inviting split-level home located on a low-traffic cul-de-sac in a desirable Winchester neighborhood. The main level features an open-concept kitchen that flows into the family and dining areas, ideal for everyday living and entertaining. Three bedrooms and two full baths complete this level, including a primary bedroom with an ensuite bath. The lower level provides flexible space with walk-out access to the backyard, perfect for a playroom, office, or guest area, plus a half bath and laundry. A heated attached two-car garage adds year-round convenience. With natural light throughout and a functional layout close to schools, town amenities, and commuter routes, this home offers a fantastic opportunity to enjoy Winchester living.

3 Beds ⋅ 3 Baths ⋅ 73471034 MLS

Welcome to 10 Trinity Road, an inviting split-level home located on a low-traffic cul-de-sac in a desirable Winchester neighborhood. The main level features an open-concept kitchen that flows into the family and dining areas, ideal for everyday living and entertaining. Three bedrooms and two full baths complete this level, including a primary bedroom with an ensuite bath. The lower level provides flexible space with walk-out access to the backyard, perfect for a playroom, office, or guest area, plus a half bath and laundry. A heated attached two-car garage adds year-round convenience. With natural light throughout and a functional layout close to schools, town amenities, and commuter routes, this home offers a fantastic opportunity to enjoy Winchester living.

10 Trinity Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.

$1,574,500

Great new price, below assessed value!!! Exceptional Victorian era gem, steps from Town Center, schools, commuter rail, and the Fells! This spacious period home seamlessly blends modern elegance with timeless charm. It’s special features include: an inviting farmer’s porch, generous living and dining rooms well-suited for entertaining, first floor family room, covered porch for al fresco dining, primary suite with ensuite bath, home office, sun room, central AC (8 mini-splits), Lochinvar heating sys (2025), hardwood floors, 3 fireplaces, and more. The stunning kitchen combines function, design, and quality showcasing custom cabinets, granite countertops, stainless appliances, and tasteful lighting. The lower level, with an outside entrance and a half bath, is well suited for an in-law suite, or au pair accommodations. The lovely backyard with its Zen Garden includes many thoughtfully organized plantings and flowering trees. COME SEE THE RECENTLY RENOVATED 3RD FLOOR!

4 Beds ⋅ 4 Baths ⋅ 73461480 MLS

Great new price, below assessed value!!! Exceptional Victorian era gem, steps from Town Center, schools, commuter rail, and the Fells! This spacious period home seamlessly blends modern elegance with timeless charm. It’s special features include: an inviting farmer’s porch, generous living and dining rooms well-suited for entertaining, first floor family room, covered porch for al fresco dining, primary suite with ensuite bath, home office, sun room, central AC (8 mini-splits), Lochinvar heating sys (2025), hardwood floors, 3 fireplaces, and more. The stunning kitchen combines function, design, and quality showcasing custom cabinets, granite countertops, stainless appliances, and tasteful lighting. The lower level, with an outside entrance and a half bath, is well suited for an in-law suite, or au pair accommodations. The lovely backyard with its Zen Garden includes many thoughtfully organized plantings and flowering trees. COME SEE THE RECENTLY RENOVATED 3RD FLOOR!

263 Highland Ave, Winchester

Listing courtesy of Listing Agent: Seeme Moreira from Listing Office: Coldwell Banker Realty - Lexington.

$1,560,000

Expanded Cape blends timeless charm with thoughtful updates, offering inviting living spaces designed for comfort and connection. A fireplaced living room with hardwood floors and French doors sets a warm tone, flowing into an elegant dining area accented by custom built-ins and refined detailing. The kitchen serves as the heart of the home, featuring stone countertops, stainless appliances, and a generous island that opens to a sunny dining area with direct access to outdoor living—ideal for everyday enjoyment and entertaining. The main-level primary suite, along with a versatile family room or optional 5th bedroom, provides flexibility for a variety of living needs. Upstairs, 3 additional bedrooms offer comfortable retreats with excellent closet space and natural light. A finished lower level extends the living area with adaptable space and walk-out access to the garage. Outdoor spaces include a welcoming porch, deck, & patio, creating a peaceful setting for gatherings & relaxation.

4 Beds ⋅ 3 Baths ⋅ 73480220 MLS

Expanded Cape blends timeless charm with thoughtful updates, offering inviting living spaces designed for comfort and connection. A fireplaced living room with hardwood floors and French doors sets a warm tone, flowing into an elegant dining area accented by custom built-ins and refined detailing. The kitchen serves as the heart of the home, featuring stone countertops, stainless appliances, and a generous island that opens to a sunny dining area with direct access to outdoor living—ideal for everyday enjoyment and entertaining. The main-level primary suite, along with a versatile family room or optional 5th bedroom, provides flexibility for a variety of living needs. Upstairs, 3 additional bedrooms offer comfortable retreats with excellent closet space and natural light. A finished lower level extends the living area with adaptable space and walk-out access to the garage. Outdoor spaces include a welcoming porch, deck, & patio, creating a peaceful setting for gatherings & relaxation.

17 Cranston Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.

$1,558,200

Nestled directly across from the breathtaking Middlesex Fells Reservation, this home offers the perfect blend of charm, space, and potential. This classic 3-bedroom, 2.5 bath Cape is beautifully situated on over half an acre in one of Winchester’s most desirable locations. The home features mostly hardwood floors throughout, a brand-new roof, and a newer heating and AC system. The second floor includes three bedrooms, including a primary suite with a walk-in closet. The first floor offers a spacious eat-in kitchen, a formal dining room, an office, and a front-to-back living room with fireplace with access to a sun porch. The lower level is ideal for a family room, complete with a fireplace. The generous lot provides exciting expansion potential without sacrificing yard space. Surrounded by nature and endless recreation opportunities just steps from your front door, this home is being sold as is and presents an incredible opportunity to make it your own.

3 Beds ⋅ 3 Baths ⋅ 73448388 MLS

Nestled directly across from the breathtaking Middlesex Fells Reservation, this home offers the perfect blend of charm, space, and potential. This classic 3-bedroom, 2.5 bath Cape is beautifully situated on over half an acre in one of Winchester’s most desirable locations. The home features mostly hardwood floors throughout, a brand-new roof, and a newer heating and AC system. The second floor includes three bedrooms, including a primary suite with a walk-in closet. The first floor offers a spacious eat-in kitchen, a formal dining room, an office, and a front-to-back living room with fireplace with access to a sun porch. The lower level is ideal for a family room, complete with a fireplace. The generous lot provides exciting expansion potential without sacrificing yard space. Surrounded by nature and endless recreation opportunities just steps from your front door, this home is being sold as is and presents an incredible opportunity to make it your own.

82 Hillcrest Parkway, Winchester

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

$1,550,000

Welcome to 205 Ridge Street, a stunning residence that blends timeless elegance with modern comfort, perfectly designed for today’s lifestyle. Nestled in one of Winchester’s most desirable neighborhoods, this five-bedroom, three-bath home offers the perfect balance of refined living and everyday convenience. From the moment you arrive, the property’s curb appeal and thoughtful details set the tone for what awaits inside. Oak floors run throughout, while tiled kitchens and baths add sophistication. Heated bathroom floors and five heating zones ensure year-round comfort, with flexible living spaces ideal for entertaining or everyday living. The chef’s kitchen opens seamlessly to dining and living areas, while upstairs, spacious bedrooms including a serene primary suite—offer peaceful retreats. Outdoors, a beautifully landscaped yard with an eight-zone irrigation system frames the in-ground pool, which can be propane-heated. Just minutes to top-rated schools, shops, and Boston.

5 Beds ⋅ 3 Baths ⋅ 73428890 MLS

Welcome to 205 Ridge Street, a stunning residence that blends timeless elegance with modern comfort, perfectly designed for today’s lifestyle. Nestled in one of Winchester’s most desirable neighborhoods, this five-bedroom, three-bath home offers the perfect balance of refined living and everyday convenience. From the moment you arrive, the property’s curb appeal and thoughtful details set the tone for what awaits inside. Oak floors run throughout, while tiled kitchens and baths add sophistication. Heated bathroom floors and five heating zones ensure year-round comfort, with flexible living spaces ideal for entertaining or everyday living. The chef’s kitchen opens seamlessly to dining and living areas, while upstairs, spacious bedrooms including a serene primary suite—offer peaceful retreats. Outdoors, a beautifully landscaped yard with an eight-zone irrigation system frames the in-ground pool, which can be propane-heated. Just minutes to top-rated schools, shops, and Boston.

205 Ridge St, Winchester

Listing courtesy of Listing Agent: Debby Valdes from Listing Office: eXp Realty.

$1,549,000

Must see! Nestled along Winchesters beloved Winter Pond, this beautiful home offers a rare opportunity to live the waterfront dream just 7 miles from Boston! Featuring an oversized lot with breathtaking panoramic water views & offering a lifestyle that could include kayaking, paddle boarding, ice skating, fishing etc..along with serenity and privacy so hard to find. This home offers ample living space that flows nicely between the formal living room, dining room, kitchen, office and family room, all of which have picturesque views. Many recent updates including kitchen, baths, roof, heating & de-leading; making this lovely home move in ready! 3 to 4 bedrooms, 2 1/2 baths w/ a finished walk out basement w/ mud room, laundry, rec. room, storage and gym area. The setting is simply gorgeous with expansive rolling green lawn offering plenty of room for future expansion.Enjoy your morning coffee from deck appreciating all that nature offers, plus spectacular sunsets in the western skies!

3 Beds ⋅ 3 Baths ⋅ 73449320 MLS

Must see! Nestled along Winchesters beloved Winter Pond, this beautiful home offers a rare opportunity to live the waterfront dream just 7 miles from Boston! Featuring an oversized lot with breathtaking panoramic water views & offering a lifestyle that could include kayaking, paddle boarding, ice skating, fishing etc..along with serenity and privacy so hard to find. This home offers ample living space that flows nicely between the formal living room, dining room, kitchen, office and family room, all of which have picturesque views. Many recent updates including kitchen, baths, roof, heating & de-leading; making this lovely home move in ready! 3 to 4 bedrooms, 2 1/2 baths w/ a finished walk out basement w/ mud room, laundry, rec. room, storage and gym area. The setting is simply gorgeous with expansive rolling green lawn offering plenty of room for future expansion.Enjoy your morning coffee from deck appreciating all that nature offers, plus spectacular sunsets in the western skies!

32 Woodside Road, Winchester

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

$1,530,000

Step into timeless charm in this STUNNING, impeccably maintained Dutch Colonial Revival home, where historic character meets modern living! Thoughtfully updated with 4 bedrooms and 4 baths, including TWO ENSUITE RETREATS—one private and perfect as a 4th bedroom, au pair suite, studio, or office. Endless flexibility! The updated kitchen shines with abundant cabinetry, center island, granite countertops, gas range, and stainless-steel appliances. First-floor laundry! Soaring ceilings and sun-filled rooms with ALL DAY NATURAL LIGHT deliver effortless comfort. Original balusters and custom built-ins preserve the home’s classic soul. Outside, enjoy a FENCED YARD, lush, curated landscaping, and raised garden beds with rich soil. An aluminum one-car garage and off-street parking add ease. Set in a coveted Winchester location just 0.4 miles to the vibrant town center, farmers market, and train—this is a rare blend of space, charm, walkability, and convenience. Get ready to fall in love!

4 Beds ⋅ 4 Baths ⋅ 73480199 MLS

Step into timeless charm in this STUNNING, impeccably maintained Dutch Colonial Revival home, where historic character meets modern living! Thoughtfully updated with 4 bedrooms and 4 baths, including TWO ENSUITE RETREATS—one private and perfect as a 4th bedroom, au pair suite, studio, or office. Endless flexibility! The updated kitchen shines with abundant cabinetry, center island, granite countertops, gas range, and stainless-steel appliances. First-floor laundry! Soaring ceilings and sun-filled rooms with ALL DAY NATURAL LIGHT deliver effortless comfort. Original balusters and custom built-ins preserve the home’s classic soul. Outside, enjoy a FENCED YARD, lush, curated landscaping, and raised garden beds with rich soil. An aluminum one-car garage and off-street parking add ease. Set in a coveted Winchester location just 0.4 miles to the vibrant town center, farmers market, and train—this is a rare blend of space, charm, walkability, and convenience. Get ready to fall in love!

259 Washington Street, Winchester

Listing courtesy of Listing Agent: Laurie Cappuccio from Listing Office: Classified Realty Group.

$1,515,000

Move right into this spacious, light-filled townhouse at The Ledges! This upscale condominium community right outside Winchester center offers the ease of low maintenance living with the feel of a single family home & with the added bonus of a private club w/swimming pool and tennis court! This sought after layout offers a grand FIRST FLOOR PRIMARY bedroom & bath suite. Easy access main floor w/ direct entry from garage features a flowing, casual layout w/ beautiful family room w/ fireplace & vaulted ceilings leading to deck, a spacious dining area, great kitchen with sunny breakfast area, laundry & half bath. Second floor offers a spacious bedroom, loft/office, sitting/ tv room/ or guest room & full bath. The finished walk out lower level includes a generously sized family/ game room, space for additional bedroom, bath & storage! Conveniently located w/ easy access to Winchester center, Whole foods market, major highways & many great restaurants and shops. Only 7 miles from Boston!

3 Beds ⋅ 3 Baths ⋅ 73500873 MLS ⋅ ['The Ledges'] BLDG.

Move right into this spacious, light-filled townhouse at The Ledges! This upscale condominium community right outside Winchester center offers the ease of low maintenance living with the feel of a single family home & with the added bonus of a private club w/swimming pool and tennis court! This sought after layout offers a grand FIRST FLOOR PRIMARY bedroom & bath suite. Easy access main floor w/ direct entry from garage features a flowing, casual layout w/ beautiful family room w/ fireplace & vaulted ceilings leading to deck, a spacious dining area, great kitchen with sunny breakfast area, laundry & half bath. Second floor offers a spacious bedroom, loft/office, sitting/ tv room/ or guest room & full bath. The finished walk out lower level includes a generously sized family/ game room, space for additional bedroom, bath & storage! Conveniently located w/ easy access to Winchester center, Whole foods market, major highways & many great restaurants and shops. Only 7 miles from Boston!

7 Wainwright Road Unit 107, Winchester

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

$1,502,500

Exceptional 3 Bedroom 3 1/2 Bath Highly Desired End Unit Townhome at The Ledges! Main Level Features include: Inviting Sun-Filled Entry Foyer, Gleaming Hardwood Floors, Cathedral Ceilings, Granite/Stainless Chef's Kitchen w/Breakfast Room, Formal Dining Room, Living Room w/Gas Fireplace and Private Deck overlooking Tranquil Wooded Setting. Family Study w/ Custom Built-ins, Luxurious Primary Bedroom Suite w/Dual Walk in Closets and Spa-Like Bath. The Second Level offers a Spacious Bedroom, W-I-C, Full Bath and Office. Finished Lower Level Oversized 3rd Bedroom Retreat w/Relaxing Sitting Area and Full Bath. Professionally Landscaped Courtyard Patio with Mature Plantings. Amenities include Pool, Pickle Ball/Tennis Courts and Clubhouse to Enjoy! Convenient to Winchester Center and Major Routes!

3 Beds ⋅ 4 Baths ⋅ 73447418 MLS ⋅ ['The Ledges'] BLDG.

Exceptional 3 Bedroom 3 1/2 Bath Highly Desired End Unit Townhome at The Ledges! Main Level Features include: Inviting Sun-Filled Entry Foyer, Gleaming Hardwood Floors, Cathedral Ceilings, Granite/Stainless Chef's Kitchen w/Breakfast Room, Formal Dining Room, Living Room w/Gas Fireplace and Private Deck overlooking Tranquil Wooded Setting. Family Study w/ Custom Built-ins, Luxurious Primary Bedroom Suite w/Dual Walk in Closets and Spa-Like Bath. The Second Level offers a Spacious Bedroom, W-I-C, Full Bath and Office. Finished Lower Level Oversized 3rd Bedroom Retreat w/Relaxing Sitting Area and Full Bath. Professionally Landscaped Courtyard Patio with Mature Plantings. Amenities include Pool, Pickle Ball/Tennis Courts and Clubhouse to Enjoy! Convenient to Winchester Center and Major Routes!

7 Wainwright Rd Unit 118, Winchester

Listing courtesy of Listing Agent: Giordana Fioravanti Smith from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$1,500,000

Located in the highly desirable Rangeley Estates - a location that puts everyday conveniences close with comfortable living. The main level is designed for everyday living & entertaining with a spacious fireplaced living room with built-in bookcase, separate family room with large closets, dining room opens to deck for easy indoor/outdoor entertaining, kitchen with island seating & stainless steel appliances, bedroom/office, bathroom with shower, & mudroom with storage. Hardwood floors extend throughout most of the first floor. Upstairs offers two bedrooms & full bath, including primary bedroom with skylight, large walk-in closet. Lower level provides valuable bonus space ideal for home office, gym, or playroom, plus laundry area & storage. Conveniently located near schools, shopping, restaurants, local amenities, train, parks, trails & outdoor recreation - this home offers a neighborhood setting with easy access to everything the area has to offer. A must see!

3 Beds ⋅ 2 Baths ⋅ 73538612 MLS

Located in the highly desirable Rangeley Estates - a location that puts everyday conveniences close with comfortable living. The main level is designed for everyday living & entertaining with a spacious fireplaced living room with built-in bookcase, separate family room with large closets, dining room opens to deck for easy indoor/outdoor entertaining, kitchen with island seating & stainless steel appliances, bedroom/office, bathroom with shower, & mudroom with storage. Hardwood floors extend throughout most of the first floor. Upstairs offers two bedrooms & full bath, including primary bedroom with skylight, large walk-in closet. Lower level provides valuable bonus space ideal for home office, gym, or playroom, plus laundry area & storage. Conveniently located near schools, shopping, restaurants, local amenities, train, parks, trails & outdoor recreation - this home offers a neighborhood setting with easy access to everything the area has to offer. A must see!

14 Rangeley Rdg, Winchester

Listing courtesy of Listing Agent: Peter Rooney from Listing Office: Compass.

$1,500,000

Beautifully renovated multi-level home in top location abutting the town forest conservation/ walking trails & just minutes from downtown Winchester! This move-in ready property features many recent upgrades, 3+ bedrooms, hardwood floors w/an open concept spacious layout perfect for modern living. The large updated kitchen includes high-end appliances, gas stove, beverage fridge & an oversized island with plenty of prep and seating space. Enjoy meals in the dining area with a custom built-in banquette. The open living area features an oversized living room with fireplace, the adjacent sunroom/ home office or 4th bedroom overlooks the back yard and town forest-ideal for relaxing or entertaining. Additional highlights include large bedrooms, a primary with ensuite bath, a large LL family room w/ bar, fireplace & a 2-car garage plus 3 season bonus room. Many flexible living spaces for a home office or guests w/ thoughtful updates throughout. A must-see home in a peaceful perfect setting!

3 Beds ⋅ 3 Baths ⋅ 73410427 MLS

Beautifully renovated multi-level home in top location abutting the town forest conservation/ walking trails & just minutes from downtown Winchester! This move-in ready property features many recent upgrades, 3+ bedrooms, hardwood floors w/an open concept spacious layout perfect for modern living. The large updated kitchen includes high-end appliances, gas stove, beverage fridge & an oversized island with plenty of prep and seating space. Enjoy meals in the dining area with a custom built-in banquette. The open living area features an oversized living room with fireplace, the adjacent sunroom/ home office or 4th bedroom overlooks the back yard and town forest-ideal for relaxing or entertaining. Additional highlights include large bedrooms, a primary with ensuite bath, a large LL family room w/ bar, fireplace & a 2-car garage plus 3 season bonus room. Many flexible living spaces for a home office or guests w/ thoughtful updates throughout. A must-see home in a peaceful perfect setting!

17 Dennett Road, Winchester

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

$1,499,000

Charm and character meet modern living in this beautifully renovated & expanded Victorian townhome just steps from Winchester Center. Fully updated in 2013/14 with new kitchen, baths, wiring, all systems, roof, and windows—and enhanced in 2023 with a redesigned patio, landscaping, fencing, and flower beds—in the exclusive yard. This home offers four levels of sun-filled space. The main level features 9’ ceilings, an open floor plan, and a chef’s kitchen with Viking appliances, large center island, with direct slider access to the fabulous private yard & patio. Upstairs includes a serene primary suite with walk-in closet and spa-like bath, plus two add’l bedrooms, full bath, & laundry. The third floor provides two more bedrooms and a full bath, ideal for guests, au- pair/ nannies or offices. A spacious lower-level family room, garage access, and storage complete this exceptional home with easy access to the center, schools, and train making it easy to enjoy all Winchester has to offer!

5 Beds ⋅ 4 Baths ⋅ 73449686 MLS

Charm and character meet modern living in this beautifully renovated & expanded Victorian townhome just steps from Winchester Center. Fully updated in 2013/14 with new kitchen, baths, wiring, all systems, roof, and windows—and enhanced in 2023 with a redesigned patio, landscaping, fencing, and flower beds—in the exclusive yard. This home offers four levels of sun-filled space. The main level features 9’ ceilings, an open floor plan, and a chef’s kitchen with Viking appliances, large center island, with direct slider access to the fabulous private yard & patio. Upstairs includes a serene primary suite with walk-in closet and spa-like bath, plus two add’l bedrooms, full bath, & laundry. The third floor provides two more bedrooms and a full bath, ideal for guests, au- pair/ nannies or offices. A spacious lower-level family room, garage access, and storage complete this exceptional home with easy access to the center, schools, and train making it easy to enjoy all Winchester has to offer!

209 Washington St Unit 209, Winchester

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

$1,475,000

Set on a picturesque corner lot in Winchester’s coveted West Side near the Ambrose School, this beautifully preserved mid-century modern home is defined by clean lines, a thoughtful layout, and so many meaningful updates throughout. The main level features a sun-filled, fireplaced living room and a formal dining room with built-ins that flow to an inviting kitchen with stainless-steel appliances. The family room serves as the home’s architectural focal point, distinguished by a cathedral ceiling, expansive picture windows, and a sliding glass door. Two bedrooms and a full bath round out this floor. The lower level adds versatility with a bedroom currently styled as a den, highlighted by a bay window, fireplace, and closet. A spacious exercise room with laundry and storage is complemented by a tastefully renovated porcelain bathroom and direct garage access. Outdoors, landscaped grounds frame a wraparound patio, creating a private setting for enjoyment throughout the seasons.

3 Beds ⋅ 2 Baths ⋅ 73485803 MLS

Set on a picturesque corner lot in Winchester’s coveted West Side near the Ambrose School, this beautifully preserved mid-century modern home is defined by clean lines, a thoughtful layout, and so many meaningful updates throughout. The main level features a sun-filled, fireplaced living room and a formal dining room with built-ins that flow to an inviting kitchen with stainless-steel appliances. The family room serves as the home’s architectural focal point, distinguished by a cathedral ceiling, expansive picture windows, and a sliding glass door. Two bedrooms and a full bath round out this floor. The lower level adds versatility with a bedroom currently styled as a den, highlighted by a bay window, fireplace, and closet. A spacious exercise room with laundry and storage is complemented by a tastefully renovated porcelain bathroom and direct garage access. Outdoors, landscaped grounds frame a wraparound patio, creating a private setting for enjoyment throughout the seasons.

28 Emerson Road, Winchester

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

$1,470,000

Classic New England charm defines this pristine 3-bedroom, 2.5-bath Colonial set on a generous, level corner lot with a beautiful stone wall in a sought-after neighborhood. Lovingly maintained by the same owners for over 50 years, the home is neat as a pin and filled with warmth and character. Hardwood floors, a traditional Colonial layout, and a fireplaced living room create comfortable living spaces, while a lovely sunroom brings in abundant natural light. Spacious bedrooms offer comfort, and the partially finished basement provides bonus space for work or play. An attached two-car garage adds everyday convenience. Ideally located just about .5 mile to the MBTA Wedgemere commuter rail station for easy Boston access, with quick connections to I-93 and nearby outdoor recreation at the Middlesex Fells Reservation. Move right in and enjoy, with the option to make thoughtful updates over time in a home that truly reflects pride of ownership.

3 Beds ⋅ 3 Baths ⋅ 73475677 MLS

Classic New England charm defines this pristine 3-bedroom, 2.5-bath Colonial set on a generous, level corner lot with a beautiful stone wall in a sought-after neighborhood. Lovingly maintained by the same owners for over 50 years, the home is neat as a pin and filled with warmth and character. Hardwood floors, a traditional Colonial layout, and a fireplaced living room create comfortable living spaces, while a lovely sunroom brings in abundant natural light. Spacious bedrooms offer comfort, and the partially finished basement provides bonus space for work or play. An attached two-car garage adds everyday convenience. Ideally located just about .5 mile to the MBTA Wedgemere commuter rail station for easy Boston access, with quick connections to I-93 and nearby outdoor recreation at the Middlesex Fells Reservation. Move right in and enjoy, with the option to make thoughtful updates over time in a home that truly reflects pride of ownership.

2 Canterbury Rd, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,460,000

Beautiful 2 family-duplex nestled in Winchester's desirable West Side. It tells the story of a home that has been treasured and exceptionally maintained over the years. Rich in warmth offering the kind of enduring quality and care that is increasingly hard to find. It reflects years of thoughtful stewardship with inviting spaces, natural light & flow designed for everyday living. Unit 1 3 beds w/primary suite, office, 2.5 baths, living room, dining room, family room with built-in shelving, eat-in kitchen. Unit 2 2 beds, 1.5 baths, living room, dining room, kitchen, lower level family room. Each unit bodes hardwood floors, in-unit laundry, dedicated basements with high ceilings, driveways, yards with patios. This special home offers flexibility, strong roots & the opportunity to become part of a beloved community. Located in sought after Vinson Owen School within Winchester's top rated school system. Minutes to Winchester Center, 2 MBTA stations direct to Boston & dining!

5 Beds ⋅ 5 Baths ⋅ 73527738 MLS

Beautiful 2 family-duplex nestled in Winchester's desirable West Side. It tells the story of a home that has been treasured and exceptionally maintained over the years. Rich in warmth offering the kind of enduring quality and care that is increasingly hard to find. It reflects years of thoughtful stewardship with inviting spaces, natural light & flow designed for everyday living. Unit 1 3 beds w/primary suite, office, 2.5 baths, living room, dining room, family room with built-in shelving, eat-in kitchen. Unit 2 2 beds, 1.5 baths, living room, dining room, kitchen, lower level family room. Each unit bodes hardwood floors, in-unit laundry, dedicated basements with high ceilings, driveways, yards with patios. This special home offers flexibility, strong roots & the opportunity to become part of a beloved community. Located in sought after Vinson Owen School within Winchester's top rated school system. Minutes to Winchester Center, 2 MBTA stations direct to Boston & dining!

7-9 Ridge St, Winchester

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

$1,450,000

This spacious four bedroom Colonial is located in the desirable westside neighborhood and Ambrose school. The first level has a fully applianced kitchen followed by a oversized dining room. There is a wood burning fireplace in the spacious living room. A family room is off the kitchen and also an office and half-bath completes this level. The second level has four very large bedrooms. The main bedroom has a walk-in closet and bath. A second bathroom on this level.. Pull down stairs to the attic in the hallway. the lower level has a finished room currently used as a bedroom but has multi uses. Direct access to the 2-car garage. The heated Gunite pool was installed by the current owners along with the enclosed fencing. Home sited on a large level lot. Great location near Whole Foods and Mahoney's. Short ride to the center of town. Desirable Vinson Owen School

4 Beds ⋅ 3 Baths ⋅ 73486878 MLS

This spacious four bedroom Colonial is located in the desirable westside neighborhood and Ambrose school. The first level has a fully applianced kitchen followed by a oversized dining room. There is a wood burning fireplace in the spacious living room. A family room is off the kitchen and also an office and half-bath completes this level. The second level has four very large bedrooms. The main bedroom has a walk-in closet and bath. A second bathroom on this level.. Pull down stairs to the attic in the hallway. the lower level has a finished room currently used as a bedroom but has multi uses. Direct access to the 2-car garage. The heated Gunite pool was installed by the current owners along with the enclosed fencing. Home sited on a large level lot. Great location near Whole Foods and Mahoney's. Short ride to the center of town. Desirable Vinson Owen School

34 Robinhood Road, Winchester

Listing courtesy of Listing Agent: Janet Halloran from Listing Office: RE/MAX Real Estate Center.

$1,440,150

Exceptional opportunity in a highly desirable Winchester neighborhood! This spacious 6-bedroom home offers incredible flexibility for today's lifestyle, perfect for multi-generational living, work-from-home setups, or growing households. The sun-filled main level 3-bedrooms feature hardwood floors and a seamless flow, ideal for both everyday living and entertaining. The updated second floor includes a full bath, private laundry, and generously sized 3 bedrooms with abundant natural light. A standout feature is the expansive 1,337 sq ft lower level - ideal for a playroom, gym, media room, or future customization. Enjoy a level, private backyard perfect for outdoor gatherings, gardening, and recreation. Conveniently located near top-rated schools, commuter rail, and Winchester center. Incredible value and space in one of Winchester's most sought-after communities!! The seller will gift the new buyer a pool and a ping-pong table for the playroom.

6 Beds ⋅ 3 Baths ⋅ 73498871 MLS

Exceptional opportunity in a highly desirable Winchester neighborhood! This spacious 6-bedroom home offers incredible flexibility for today's lifestyle, perfect for multi-generational living, work-from-home setups, or growing households. The sun-filled main level 3-bedrooms feature hardwood floors and a seamless flow, ideal for both everyday living and entertaining. The updated second floor includes a full bath, private laundry, and generously sized 3 bedrooms with abundant natural light. A standout feature is the expansive 1,337 sq ft lower level - ideal for a playroom, gym, media room, or future customization. Enjoy a level, private backyard perfect for outdoor gatherings, gardening, and recreation. Conveniently located near top-rated schools, commuter rail, and Winchester center. Incredible value and space in one of Winchester's most sought-after communities!! The seller will gift the new buyer a pool and a ping-pong table for the playroom.

65 High Street, Winchester

Listing courtesy of Listing Agent: Anna Jung from Listing Office: K Stadium Realty INC.

$1,427,000

CANCELED OPEN HOUSE - offer accepted. Ready to not worry about shoveling or taking care of a yard? Come have carefree living at the Ledges in Winchester. Delight in a small, manageable courtyard that you can view from your eat-in kitchen table. Enjoy a 2-car garage, laundry and a gorgeous primary suite on the main living level. Living room has gas fireplace, built-ins, access to nice deck and is open to the dining area. PLUS 2 bedrooms, 2 more full baths, office, loft and family room on other levels. Plenty of options for family and guests. Current owner replaced LR/DR/Primary carpet with lovely hardwood floors!! This unit is in the section of the Ledges that looks out over Sucker Brook Conservation Area where the seasonal beauty and birds never end! Think you'll feel cramped if you downsize? Not here! The soaring ceiling in the living room (with skylight) and primary bedroom bring grandeur and plenty of natural light. Fantastic community w/ pool, clubhouse and tennis court.

3 Beds ⋅ 4 Baths ⋅ 73473597 MLS ⋅ ['The Ledges'] BLDG.

CANCELED OPEN HOUSE - offer accepted. Ready to not worry about shoveling or taking care of a yard? Come have carefree living at the Ledges in Winchester. Delight in a small, manageable courtyard that you can view from your eat-in kitchen table. Enjoy a 2-car garage, laundry and a gorgeous primary suite on the main living level. Living room has gas fireplace, built-ins, access to nice deck and is open to the dining area. PLUS 2 bedrooms, 2 more full baths, office, loft and family room on other levels. Plenty of options for family and guests. Current owner replaced LR/DR/Primary carpet with lovely hardwood floors!! This unit is in the section of the Ledges that looks out over Sucker Brook Conservation Area where the seasonal beauty and birds never end! Think you'll feel cramped if you downsize? Not here! The soaring ceiling in the living room (with skylight) and primary bedroom bring grandeur and plenty of natural light. Fantastic community w/ pool, clubhouse and tennis court.

7 Wainwright Road Unit 15, Winchester

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

$1,425,000

Cleverly reimagined for modern living, this energy-efficient Craftsman bungalow is ideally located in Winchester with close proximity to the natural beauty of the Middlesex Fells and the shops, dining and commuter rail of the town center. Thoughtfully expanded and renovated, the home features newer systems, windows and roof, among too many other updates to list. A functional mudroom with custom storage welcomes you inside, where the living room flows seamlessly into an exquisite chef’s kitchen with premium appliances, dual sinks and a dining room overlooking the landscaped, fully fenced yard. A spacious bedroom and full bath complete this level. Upstairs offers three additional bedrooms, two full baths and laundry, highlighted by a generous primary suite with walk-in closet and spa-like bath, complete with soaking tub and extra large shower. Owned solar panels, EV charging, a one-car garage, and a versatile lower level with bonus room complete this exceptional offering.

4 Beds ⋅ 3 Baths ⋅ 73480343 MLS

Cleverly reimagined for modern living, this energy-efficient Craftsman bungalow is ideally located in Winchester with close proximity to the natural beauty of the Middlesex Fells and the shops, dining and commuter rail of the town center. Thoughtfully expanded and renovated, the home features newer systems, windows and roof, among too many other updates to list. A functional mudroom with custom storage welcomes you inside, where the living room flows seamlessly into an exquisite chef’s kitchen with premium appliances, dual sinks and a dining room overlooking the landscaped, fully fenced yard. A spacious bedroom and full bath complete this level. Upstairs offers three additional bedrooms, two full baths and laundry, highlighted by a generous primary suite with walk-in closet and spa-like bath, complete with soaking tub and extra large shower. Owned solar panels, EV charging, a one-car garage, and a versatile lower level with bonus room complete this exceptional offering.

15 Englewood Road, Winchester

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

$1,425,000

Attention renovators and investors! This Cape-style home in need of significant renovation offers 7 rooms, 4 bedrooms, and 2 full baths. Features include a fireplace living room, dining room, and hardwood flooring throughout. Enjoy a private yard for outdoor enjoyment. Prime location directly across from the Middlesex Fells Reservation and minutes to Winchester Center, schools, shops, and restaurants. Great potential to restore or redevelop in one of Winchester’s most desirable areas. All offers due Tuesday the 28th at 12 PM.

4 Beds ⋅ 2 Baths ⋅ 73447622 MLS

Attention renovators and investors! This Cape-style home in need of significant renovation offers 7 rooms, 4 bedrooms, and 2 full baths. Features include a fireplace living room, dining room, and hardwood flooring throughout. Enjoy a private yard for outdoor enjoyment. Prime location directly across from the Middlesex Fells Reservation and minutes to Winchester Center, schools, shops, and restaurants. Great potential to restore or redevelop in one of Winchester’s most desirable areas. All offers due Tuesday the 28th at 12 PM.

102 Hillcrest Pkwy, Winchester

Listing courtesy of Listing Agent: Curtis Howe from Listing Office: Howe Realty Group.

$1,400,000

This charming home abounds in style and character. It is Steps to downtown Winchester, where you can enjoy a variety of fine restaurants, easy commute to Boston & be able to walk to all the public schools & St. Mary's .Beautiful natural wood trim & hdwd floors throughout, grace this home. A spacious & sunny kitchen w/ center island, great for entertaining w/ a built-in desk. Large pantry for storage. Lots of cabinets, and stainless steel appliances. The dining room showcases a built-in display china cabinet. Formal living room with a gas f.p. and french doors leading to an informal family room. A wrap around screened- in porch which will expand your lifestyle in the summer, overlooking a front yard with beautiful perennials. Upstairs: 3 bedrooms plus a small office space w/built-ins. Spacious tile bathroom with soaking tub, shower and double sinks. Parking for 3-4 cars. 4th B/R on 3rd floor. EV charger, .Full basement w/sink.

3 Beds ⋅ 2 Baths ⋅ 73503540 MLS

This charming home abounds in style and character. It is Steps to downtown Winchester, where you can enjoy a variety of fine restaurants, easy commute to Boston & be able to walk to all the public schools & St. Mary's .Beautiful natural wood trim & hdwd floors throughout, grace this home. A spacious & sunny kitchen w/ center island, great for entertaining w/ a built-in desk. Large pantry for storage. Lots of cabinets, and stainless steel appliances. The dining room showcases a built-in display china cabinet. Formal living room with a gas f.p. and french doors leading to an informal family room. A wrap around screened- in porch which will expand your lifestyle in the summer, overlooking a front yard with beautiful perennials. Upstairs: 3 bedrooms plus a small office space w/built-ins. Spacious tile bathroom with soaking tub, shower and double sinks. Parking for 3-4 cars. 4th B/R on 3rd floor. EV charger, .Full basement w/sink.

205 Washington St., Winchester

Listing courtesy of Listing Agent: Jayne Zeamer from Listing Office: Coldwell Banker Realty - Boston.

$1,400,000

Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is designed for convenience with double sinks and new shower. The exterior of the home is just as impressive with fresh exterior paint and a deck for outdoor enjoyment. This home is a must-see!. Included 100-Day Home Warranty with buyer activation.

3 Beds ⋅ 3 Baths ⋅ 73451080 MLS

Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is designed for convenience with double sinks and new shower. The exterior of the home is just as impressive with fresh exterior paint and a deck for outdoor enjoyment. This home is a must-see!. Included 100-Day Home Warranty with buyer activation.

26 Berkshire Dr, Winchester

Listing courtesy of Listing Agent: Daniel Beirne from Listing Office: OpenDoor Brokerage LLC.

$1,399,000

This bright and airy home unfolds into nearly 3,000 sq ft of beautifully designed living space, ideally set in a quiet, established Winchester neighborhood. Cherry cabinet kitchen with stainless steel appliances and skylight and a spacious family room with wet bar, The lowest level great room features a stunning floor-to-ceiling stone-faced gas fireplace with expansive western views. Two home offices and an exercise area offer flexibility for today’s lifestyle. Multiple rooms lead to a fabulous 1133 sq ft decking system. Additional highlights include a 4-zone irrigation system, solar panels, newer heat pumps, and mini splits for heat and central air. Convenient to the Middlesex Fells Reservation with miles of trails for hiking, biking, and outdoor recreation. Enjoy easy access to the Wedgemere Station commuter train. A perfect blend of suburban tranquility, natural surroundings, and commuter convenience, a short distance to Winchester Center shops, dining, and community amenities.

3 Beds ⋅ 4 Baths ⋅ 73501230 MLS

This bright and airy home unfolds into nearly 3,000 sq ft of beautifully designed living space, ideally set in a quiet, established Winchester neighborhood. Cherry cabinet kitchen with stainless steel appliances and skylight and a spacious family room with wet bar, The lowest level great room features a stunning floor-to-ceiling stone-faced gas fireplace with expansive western views. Two home offices and an exercise area offer flexibility for today’s lifestyle. Multiple rooms lead to a fabulous 1133 sq ft decking system. Additional highlights include a 4-zone irrigation system, solar panels, newer heat pumps, and mini splits for heat and central air. Convenient to the Middlesex Fells Reservation with miles of trails for hiking, biking, and outdoor recreation. Enjoy easy access to the Wedgemere Station commuter train. A perfect blend of suburban tranquility, natural surroundings, and commuter convenience, a short distance to Winchester Center shops, dining, and community amenities.

71 Sargent Road, Winchester

Listing courtesy of Listing Agent: Bob Bittelari from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$1,399,000

Another Tree Top Group masterpiece –Welcome to 4 Wyman Court! New full gut renovation townhome with 2,500 sq. ft., 4 beds, 4.5 baths & 4 levels of sun-drenched living space. Located in a prime end of cul-de-sac & moments from the vibrant Winchester Center including shops, dining & commuter rail. Main level features a thoughtfully designed kitchen w/ stainless steel appliances, a large center island, opening to bright living & dining areas w/ custom cabinetry & hardwood floors. The 2nd level offers a serene en-suite primary w/ private deck, a spacious 2nd bedroom, full bathroom, 2nd floor laundry, & includes a versatile loft ideal for office or lounge. The 3rd floor hosts a 2nd en-suite primary w/ double closets. Finished lower level boasts a 4th bedroom, full bathroom, family room w/ built-ins, & wet bar! Additional highlights include a 1-car garage, an extra off-street parking space, & EV charger readiness. Luxury, location & design—your perfect Winchester townhome awaits!

4 Beds ⋅ 5 Baths ⋅ 73454901 MLS ⋅ ['4-6 Wyman Court'] BLDG.

Another Tree Top Group masterpiece –Welcome to 4 Wyman Court! New full gut renovation townhome with 2,500 sq. ft., 4 beds, 4.5 baths & 4 levels of sun-drenched living space. Located in a prime end of cul-de-sac & moments from the vibrant Winchester Center including shops, dining & commuter rail. Main level features a thoughtfully designed kitchen w/ stainless steel appliances, a large center island, opening to bright living & dining areas w/ custom cabinetry & hardwood floors. The 2nd level offers a serene en-suite primary w/ private deck, a spacious 2nd bedroom, full bathroom, 2nd floor laundry, & includes a versatile loft ideal for office or lounge. The 3rd floor hosts a 2nd en-suite primary w/ double closets. Finished lower level boasts a 4th bedroom, full bathroom, family room w/ built-ins, & wet bar! Additional highlights include a 1-car garage, an extra off-street parking space, & EV charger readiness. Luxury, location & design—your perfect Winchester townhome awaits!

4 Wyman Court Unit 4, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.

$1,392,500

Location, Location, Location! This beautifully maintained 3-bedroom, 2.5 bath multi-level home perfectly balances convenience and suburban charm. Enjoy an easy walk to the commuter rail, downtown shops and restaurants, schools, parks, and more. The main level features a spacious, sun-filled open floor plan with fireplaced living room, updated kitchen with skylight, and a bright sunroom offering seamless access to a large deck and level, fenced backyard--ideal for relaxing or entertaining. Upstairs you'll find 3 generous bedrooms with ample closets, including a main suite with bath and a second, full bath. Just below the main level is a versatile office or fitness room, laundry area with extra freezer and storage, and garage entry. The inviting lower-level family room boasts great natural light, a wood stove/fireplace, half bath, and a walk-in cedar closet. This warm, welcoming home offers exceptional light, layout, and location! Property is leased until 7/31/2026-well worth the wait!

3 Beds ⋅ 3 Baths ⋅ 73444073 MLS

Location, Location, Location! This beautifully maintained 3-bedroom, 2.5 bath multi-level home perfectly balances convenience and suburban charm. Enjoy an easy walk to the commuter rail, downtown shops and restaurants, schools, parks, and more. The main level features a spacious, sun-filled open floor plan with fireplaced living room, updated kitchen with skylight, and a bright sunroom offering seamless access to a large deck and level, fenced backyard--ideal for relaxing or entertaining. Upstairs you'll find 3 generous bedrooms with ample closets, including a main suite with bath and a second, full bath. Just below the main level is a versatile office or fitness room, laundry area with extra freezer and storage, and garage entry. The inviting lower-level family room boasts great natural light, a wood stove/fireplace, half bath, and a walk-in cedar closet. This warm, welcoming home offers exceptional light, layout, and location! Property is leased until 7/31/2026-well worth the wait!

53 Bacon Street, Winchester

Listing courtesy of Listing Agent: Taleen Chiofaro from Listing Office: Leading Edge Real Estate.

$1,380,000

Thoughtfully designed newer construction townhome offering the feel and privacy of a single family home. This 4 bed, 3.5 bath home features a sought-after 1st floor primary suite, sun-filled interiors, and dramatic ceiling height that enhances the home’s bright, airy feel. Hardwood floors and a gas fireplaced family room flow to sliders leading to a private deck, patio, and fenced yard. The kitchen is well-appointed with quartz countertops and high-end appliances, ideal for everyday living and entertaining. The second floor offers two spacious bedrooms, a full bath, laundry, & a versatile loft, perfect for a home office, lounge, or play space, creating an open yet highly functional layout. The finished lower level includes a private suite with full bath & walk-in closet, plus additional storage to keep everyday living organized. Ideally located close to downtown shops, Packer Tennis Courts, Lynch, McCall & WHS, commuter rail, Tri-Community Bike Path, and easy access to Routes 93 & 95.

4 Beds ⋅ 4 Baths ⋅ 73470827 MLS

Thoughtfully designed newer construction townhome offering the feel and privacy of a single family home. This 4 bed, 3.5 bath home features a sought-after 1st floor primary suite, sun-filled interiors, and dramatic ceiling height that enhances the home’s bright, airy feel. Hardwood floors and a gas fireplaced family room flow to sliders leading to a private deck, patio, and fenced yard. The kitchen is well-appointed with quartz countertops and high-end appliances, ideal for everyday living and entertaining. The second floor offers two spacious bedrooms, a full bath, laundry, & a versatile loft, perfect for a home office, lounge, or play space, creating an open yet highly functional layout. The finished lower level includes a private suite with full bath & walk-in closet, plus additional storage to keep everyday living organized. Ideally located close to downtown shops, Packer Tennis Courts, Lynch, McCall & WHS, commuter rail, Tri-Community Bike Path, and easy access to Routes 93 & 95.

36 Middlesex St Unit 36, Winchester

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