Winchester, MA Homes

/42
Est $2,020,403 Not Listed For Sale
- 4 Beds
- 3 Baths
- 4,256 Sq Ft
15 Pilgrim Dr, Winchester, MA 01890

15 Pilgrim Dr, Winchester, MA 01890

/42
$1,285,000
- 4 Beds
- 1.5 Baths
- 2,696 Sq Ft
104 Church St, Winchester, MA 01890

This charming colonial in prime flats location is full of surprises! Showcasing a stunning rear 3 story addition duplex with walls of windows & 4 rooms! Use as the primary, home office, art studio or let your children enjoy this unique space~ The first floor offers a classic layout with an expanded updated kitchen & family area open to gorgeous deck overlooking the beacon hill style yard

Kim Covino Compass

104 Church St, Winchester, MA 01890
/42
$1,725,000 Sold Sep 19, 2025
- 2,541 Sq Ft
- $679/SF
- 6 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1960
9 Pilgrim Dr, Winchester, MA 01890

Welcome to this beautiful split-level home nestled on a desirable corner lot in Winchester’s sought after west side. Featuring gleaming hardwood floors throughout, this home offers a perfect blend of comfort and style. The main level boasts an open floor plan connecting the dining room, kitchen, and living room, and seamlessly flows into a stunning vaulted family room, perfect for both everyday

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

9 Pilgrim Dr, Winchester, MA 01890

/40
Est $1,449,018 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,142 Sq Ft
16 Johnson Rd, Winchester, MA 01890

16 Johnson Rd, Winchester, MA 01890

/30
$2,850,000
- 6 Beds
- 7 Baths
- 6,968 Sq Ft
14 Nassau Dr, Winchester, MA 01890

Amazing custom-built 6-bedroom / 5+ bathroom house on a quiet neighborhood in Winchester. 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

Weidong Li WINN Real Estate & Consulting

14 Nassau Dr, Winchester, MA 01890
/31
$1,465,000 Sold Sep 18, 2025
- 2,506 Sq Ft
- $585/SF
- 5 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1974
6 Highland Ave, Winchester, MA 01890

4 BD, 2.5 BA home tucked away from the road for added privacy. Kitchen has spacious dining area for enjoying family meals & entertaining guests. Inviting family room, w/ FP brings warm ambiance & convenient access to the deck, enhancing your indoor-outdoor living experience. Large living/dining area w/ backyard views is a versatile space w/ an open layout make it a welcoming spot. Convenience is

Peter Rooney Compass

6 Highland Ave, Winchester, MA 01890

/33
Est $2,057,891 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 4,603 Sq Ft
8 Olde Lyme Rd, Winchester, MA 01890

8 Olde Lyme Rd, Winchester, MA 01890

/23
$949,000
- 4 Beds
- 2 Baths
- 1,938 Sq Ft
380 Cross St, Winchester, MA 01890

This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The inviting 3 season porch with flagstone floor is a favorite place for family to congregate and get

Pavan Patel Realty ONE Group Nest

380 Cross St, Winchester, MA 01890
/36
$1,945,000 Sold Sep 16, 2025
- 3,825 Sq Ft
- $508/SF
- 7 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2025
20 Grayson Rd, Winchester, MA 01890

Another Tree Top Group masterpiece—where natural light, luxury finishes, & thoughtful design come together in perfect harmony. This 5-bed, 4.5-bath new construction home boasts 9+ ft ceilings, exceptional light fixtures, and a stunning waterfall center island that anchors the designer kitchen w/ custom cabinetry that extends to the ceiling. Custom built-ins & storage throughout. A sleek linear

Monte Marrocco Coldwell Banker Realty - Lexington

20 Grayson Rd, Winchester, MA 01890

/42
Est $1,794,196 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 3,315 Sq Ft
8 Hawthorne Rd, Winchester, MA 01890

8 Hawthorne Rd, Winchester, MA 01890

/35
$898,000 Open Sun 11AM - 12:30PM
- 3 Beds
- 1 Bath
- 1,425 Sq Ft
571 Washington St, Winchester, MA 01890

Best valued single family in Winchester with incredible fenced backyard and expansive patio extending your living space outdoors, and 2 car garage!! Build immediate equity and convenience by adding an additional bathroom - Plans and renderings in hand (see attached and ask agent for details)! Designed with light-filled living spaces and three generously sized bedrooms, it’s a perfect fit for

Ryan Wilson Keller Williams Realty

571 Washington St, Winchester, MA 01890
/32
$505,000 Sold Sep 15, 2025
- 822 Sq Ft
- $614/SF
- 18 Days On Market
- 2 Beds
- 1 Bath
- Built 1966
200 Swanton St Unit 239, Winchester, MA 01890

Sunny second-floor 2-bedroom unit overlooking a serene duck pond. This home features an open layout with hardwood floors, an updated granite and stainless-steel kitchen, and a modern bath with a sleek barn door. Each bedroom offers two closets, plus three additional hallway closets for exceptional storage. Enjoy a private enclosed balcony with serene views. The HOA fee includes heat, hot water,

Joan Powell RE/MAX Andrew Realty Services

200 Swanton St Unit 239, Winchester, MA 01890

/42
Est $2,537,083 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,473 Sq Ft
239 Ridge St, Winchester, MA 01890

239 Ridge St, Winchester, MA 01890

/41
$4,174,000
- 7 Beds
- 6 Baths
- 7,043 Sq Ft
2 Everett Ave, Winchester, MA 01890

Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end

Joan Francis Sullivan Better Homes and Gardens Real Estate - The Shanahan Group

2 Everett Ave, Winchester, MA 01890
/39
$1,770,000 Sold Sep 12, 2025
- 2,850 Sq Ft
- $621/SF
- 4 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2012
178 Mystic Valley Pkwy, Winchester, MA 01890

This carefully crafted Colonial, custom-built by Andrew Pywell, combines solid construction with a bounty of special touches and timeless charm. Delight in sun-splashed living spaces, gleaming hardwood floors, crown moldings, and a layout that balances an open flow, defined spaces and beautifully proportioned rooms across 2,850 square feet. The gracious formal living room, dining room, and

Katherine Waters-Clark Compass

178 Mystic Valley Pkwy, Winchester, MA 01890

/26
Est $1,152,913 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,826 Sq Ft
75 Dunster Ln, Winchester, MA 01890

75 Dunster Ln, Winchester, MA 01890

/42
$3,299,000
- 5 Beds
- 7 Baths
- 7,101 Sq Ft
257 High St, Winchester, MA 01890

Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck,

Kim Covino Compass

257 High St, Winchester, MA 01890
/40
$1,100,000 Sold Sep 12, 2025
- 1,414 Sq Ft
- $778/SF
- 8 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1900
5 Cutting St, Winchester, MA 01890

OFFER DEADLINE TUE JULY 29th 5:00PM | Exceedingly charming + in-town location to be envied. Shops, schools + both MBTA stations at your fingertips. Step up onto your porch, pass the bench swing you’re yet to install; entering into the inviting foyer w/ original stairs preserved & tall ceilings. The main level is sophisticated & functional. A front facing dining room w/ plantation shutters +

Oliver Koester Compass

5 Cutting St, Winchester, MA 01890

/42
Est $3,292,108 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 5,676 Sq Ft
222 High St, Winchester, MA 01890

222 High St, Winchester, MA 01890

/36
$3,600,000 Open Sun 12PM - 2PM
- 6 Beds
- 7 Baths
- 8,866 Sq Ft
20 Amberwood Dr, Winchester, MA 01890

Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador

Wei Wang WW Real Estate LLC

20 Amberwood Dr, Winchester, MA 01890
/38
$1,525,000 Sold Sep 12, 2025
- 2,755 Sq Ft
- $554/SF
- 30 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1929
5 Thornton Rd, Winchester, MA 01890

This stately home near the Flats blends original character with modern-day living, 8' ceilings and awaits your personal touches. The living room features stunning woodwork, a fireplace, and French doors leading to a window-lined sunroom-ideal for a home office or playroom. The large circular floor plan connects the living room with a formal dining room, family room, half bath and newer kitchen.

Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

5 Thornton Rd, Winchester, MA 01890

/27
Est $1,094,077 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,859 Sq Ft
46 Edward Dr, Winchester, MA 01890

46 Edward Dr, Winchester, MA 01890

/25
$662,500
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
2 George Rd Unit 2, Winchester, MA 01890

Presenting a charming 3- Bedrooms ,2 - Baths home at The Residences at Winchester featuring gleaming hardwood floors, freshly painted interior and updated lower level with brand new flooring. This move-in-ready has comfort , and functionality across all levels. The first floor includes bright Living room ,a dedicated dining room and an updated kitchen with granite countertops and stainless steel

Rajive Dogra Coldwell Banker Realty - Lexington

2 George Rd Unit 2, Winchester, MA 01890
/28
$710,000 Sold Sep 10, 2025
- 1,170 Sq Ft
- $607/SF
- 50 Days On Market
- 2 Beds
- 2 Baths
- Built 1982
666 Main St Unit 206, Winchester, MA 01890

Back on Market - buyer got cold feet. Welcome to Wedgewood Place at 666 Main Street in Winchester Center - a perfect blend of small-town charm and urban convenience. This desirable and well-maintained 2 bed/2 bath home comes with 1 covered parking. Enjoy a spacious open-concept layout with a wood-burning fireplace, screened-in balcony overlooking courtyard & pool, and updated kitchen and guest

Sveta Vakhitova Berkshire Hathaway HomeServices Warren Residential

666 Main St Unit 206, Winchester, MA 01890

/36
Est $1,033,168 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,568 Sq Ft
55 Edward Dr, Winchester, MA 01890

55 Edward Dr, Winchester, MA 01890

/38
$2,299,000
- 5 Beds
- 3.5 Baths
- 5,006 Sq Ft
276 High St, Winchester, MA 01890

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

Kim Covino Compass

276 High St, Winchester, MA 01890
/32
$740,000 Sold Sep 09, 2025
- 1,358 Sq Ft
- $545/SF
- 8 Days On Market
- 3 Beds
- 1 Bath
- Built 1903
15 Governors Ave Unit 1, Winchester, MA 01890

Turn-key 3-bed condo offers effortless living just moments from downtown Winchester, Muraco School, & Middlesex Fells—nothing to do but unpack your bags & settle in. The main level offers a spacious entry area that functions well as a mudroom or sitting room, along with a sunny living room, dining room, & renovated kitchen featuring granite counters, center island, ss appliances, Sub-Zero fridge,

Pirani & Wile Group Gibson Sotheby's International Realty

15 Governors Ave Unit 1, Winchester, MA 01890

/42
Est $1,050,725 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,738 Sq Ft
41 Edward Dr, Winchester, MA 01890

41 Edward Dr, Winchester, MA 01890

/27
$2,239,000
- 5 Beds
- 4.5 Baths
- 4,798 Sq Ft
61 Grove St, Winchester, MA 01890

- 2017 - STUNNING CUSTOM- BUILT HOME, COMPLETELY rebuilt and doubled in size with bright and sunny rooms and a flexible floor plan. Welcome to this easy living, maintenance free sophisticated residence. FIRST FLOOR LUXURIOUS SUITE with a LARGE BEDROOM, marble bath w/double sink vanity, walk in shower & soaking tub. An exquisite kitchen with granite island, counters and back splash, All Bosch

Dorothea Feffer Coldwell Banker Realty - Lexington

61 Grove St, Winchester, MA 01890
/34
$635,000 Sold Sep 09, 2025
- 980 Sq Ft
- $648/SF
- 4 Days On Market
- 2 Beds
- 1 Bath
- Built 1988
115 Washington St Unit 2A, Winchester, MA 01890

2 Bedroom at Church Place in Winchester Center! Move-in ready and filled with natural light, this beautifully maintained 2BR 1 BA condo is ideally located in the heart of the center. Perfect for down-sizers or anyone seeking easy living w/ access to top-rated schools & all the conveniences right outside your door. This bright and airy unit offers an open floor plan with high ceilings & beautiful

Kim Covino Compass

115 Washington St Unit 2A, Winchester, MA 01890

/38
Est $1,078,186 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,754 Sq Ft
34 Edward Dr, Winchester, MA 01890

34 Edward Dr, Winchester, MA 01890

/42
$3,499,000
- 7 Beds
- 7.5 Baths
- 7,982 Sq Ft
54 Johnson Rd, Winchester, MA 01890

This STUNNING newly constructed home facing Old Village Drive redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the

Kim Covino Compass

54 Johnson Rd, Winchester, MA 01890
/32
$868,000 Sold Sep 04, 2025
- 1,931 Sq Ft
- $450/SF
- 8 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1956
235 Cross St, Winchester, MA 01890

Lovingly cared for by its original owners for nearly 70 years, this charming ranch-style home rests proudly on a desirable corner lot in a welcoming, established neighborhood. Offering 3 comfortable bedrooms, 1.5 bathrooms, and two fireplaces, the home is filled with warmth, character, and exciting potential for new owners to make it their own. The yard comes alive each spring with vibrant

Melanie Lentini Leading Edge Real Estate

235 Cross St, Winchester, MA 01890

/37
Est $881,400 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,920 Sq Ft
47 Edward Dr, Winchester, MA 01890

47 Edward Dr, Winchester, MA 01890

/42
$3,799,000 Open Sun 12:30PM - 1:30PM
- 6 Beds
- 4.5 Baths
- 6,367 Sq Ft
40 Foxcroft Rd, Winchester, MA 01890

An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern luxury with timeless warmth in one of Winchester’s most coveted neighborhoods. Designed for elevated living, it features a chef’s kitchen with quartz counters, custom cabinetry, a large island, and built-in bar, opening to a sunlit dining area ideal for both casual meals and

Monte Marrocco Coldwell Banker Realty - Lexington

40 Foxcroft Rd, Winchester, MA 01890
/27
$690,000 Sold Sep 03, 2025
- 1,554 Sq Ft
- $444/SF
- 49 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1976
50 Lake St Unit B, Winchester, MA 01890

Buyer's cold feet gives you a second chance to own a well-maintained 2-bed, 1.5-bath townhouse-style condo offering scenic views of Wedge Pond. The main level features hardwood floors, a spacious living area, half bath, and a kitchen with granite countertops and stainless steel appliances. Upstairs offers two bedrooms and a full bath. The finished lower level provides versatile space for a family

Andersen Group Realty Keller Williams Realty Boston Northwest

50 Lake St Unit B, Winchester, MA 01890

/31
Est $1,875,566 Not Listed For Sale
- 4 Beds
- 4 Baths
- 4,028 Sq Ft
56 Ridge St, Winchester, MA 01890

56 Ridge St, Winchester, MA 01890

/38
$1,650,000 Pending
- 3 Beds
- 2.5 Baths
- 1,882 Sq Ft
82 Hillcrest Pkwy, Winchester, MA 01890

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

Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

82 Hillcrest Pkwy, Winchester, MA 01890
/41
$1,510,000 Sold Sep 02, 2025
- 1,965 Sq Ft
- $768/SF
- 8 Days On Market
- 5 Beds
- 2.5 Baths
- Built 1900
155 Highland Ave, Winchester, MA 01890

Charming turn-of-the-century 5-bedroom Gambrel-style home in move-in condition, blending classic character with modern updates. This spacious residence features a beautifully updated interior with central air, a stunning primary suite with private bath, custom closet system, and generous living spaces throughout. The detached 2-car garage adds convenience, while the location offers unbeatable

Pirani & Wile Group Gibson Sotheby's International Realty

155 Highland Ave, Winchester, MA 01890

/23
Est $1,017,694 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,548 Sq Ft
12 James St, Winchester, MA 01890

12 James St, Winchester, MA 01890

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Massachusetts Middlesex County Winchester

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