Recently Sold Homes in Winchester, MA

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SOLD OCT 3, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, MA:
Located in the popular Winchester Highlands neighborhood with Elegance and Stature is this 4 bed, 1.5 bath Center Entrance Colonial with 2 car garage, minutes to I-93 and Winchester Center with boutique shops, cafes, restaurants, and newly renovated MBTA Station. Welcoming front vestibule opens to sprawling front-to-back living room with wood burning fireplace and attached sunroom. Formal dining room with chair rail and crown molding leads to 2019 updated kitchen with new gas range, exhaust hood, countertops and hardware. A rear vestibule and mudroom with half bath complete this level. Natural woodwork and crown molding throughout the main level. Mini splits provide comfortable A/C througho

$1,280,000 Last sold price

4 beds1.5 baths1,900 sq ft

162 Forest St, Winchester, MA 01890

SOLD SEP 16, 20253D & VIDEO TOUR

ABOUT THIS HOME
Recently Sold Home in Winchester, MA:
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 fireplace adds warmth to the open-concept family room. With two primary suites to choose from, flexibility meets luxury. The third-floor primary feels like a private hotel retreat w/ a sitting area, dual walk-in closets, & a spa-inspired bath. The second-floor primary offers a sp

$1,945,000 Last sold price

5 beds4.5 baths3,825 sq ft

20 Grayson Rd, Winchester, MA 01890

SOLD SEP 18, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, MA:
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 key, w/ 1st-floor laundry area & spacious 2-car garage w/ storage. This 0.65-acre lot features a large fenced backyard with a deck, patio, & screened-in gazebo—perfect for relaxing, entertaining, or enjoying outdoor activities. Heated & A/C bonus room on 2nd floor

$1,465,000 Last sold price

4 beds2.5 baths2,506 sq ft

6 Highland Ave, Winchester, MA 01890

SOLD SEP 2, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, MA:
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 lifestyle perks—just a short stroll to the 2,600-acre Middlesex Fells Reservation. Enjoy easy access to Winchester Center’s shops, restaurants, top-rated schools, and public transportation, including the commuter rail to Boston. Quick access to Rt. 93 puts downtown Boston just minutes away.

$1,510,000 Last sold price

5 beds2.5 baths1,965 sq ft

155 Highland Ave, Winchester, MA 01890

SOLD SEP 25, 2025VIDEO TOUR

ABOUT THIS HOME
Recently Sold Home in Winchester, MA:
Call for a private showing anytime! Discover this charming renovated 3 bed 2 bath home with close proximity to the Fells trails & Winchester town center including schools, train to Boston, restaurants, shops & all the town has to offer!! Beautifully renovated & lovingly maintained, this great home welcomes you w/ a spacious living room w fplc that flows seamlessly into a sun-drenched updated kitchen featuring stainless steel appliances & stylish finishes w/ open concept dining, oversized windows & slider to deck. A family room just off the main living area offers a cozy, versatile space & potential for another BR w/ full 1st floor bath. The expansive bac

$1,200,000 Last sold price

3 beds2 baths1,884 sq ft

147 Highland Ave, Winchester, MA 01890

Property at 77 Washington St, Winchester, MA 01890, 5 beds, 3.5 baths

$1,700,000 Last sold price

5 beds3.5 baths2,718 sq ft

77 Washington St, Winchester, MA 01890

Property at 178 Mystic Valley Pkwy, Winchester, MA 01890, 3 beds, 2.5 baths

$1,770,000 Last sold price

3 beds2.5 baths2,850 sq ft

178 Mystic Valley Pkwy, Winchester, MA 01890

Property at 115 Washington St Unit 2A, Winchester, MA 01890, 2 beds, 1 bath

$635,000 Last sold price

2 beds1 bath980 sq ft

115 Washington St Unit 2A, Winchester, MA 01890

Property at 115 Washington St Unit 3D, Winchester, MA 01890, 1 bed, 1.5 baths

$519,000 Last sold price

1 bed1.5 baths769 sq ft

115 Washington St Unit 3D, Winchester, MA 01890

Property at 12 Ledgewood Rd, Winchester, MA 01890, 5 beds, 4.5 baths

$3,900,000 Last sold price

5 beds4.5 baths5,069 sq ft

12 Ledgewood Rd, Winchester, MA 01890

Property at 4 Sargent Rd, Winchester, MA 01890, 4 beds, 2.5 baths

$1,355,000 Last sold price

4 beds2.5 baths2,865 sq ft

4 Sargent Rd, Winchester, MA 01890

Property at 17 Dennett Rd, Winchester, MA 01890, 3 beds, 2.5 baths

$1,500,000 Last sold price

3 beds2.5 baths2,283 sq ft

17 Dennett Rd, Winchester, MA 01890

Property at 4 Oakland Cir, Winchester, MA 01890, 3 beds, 2 baths

$1,651,000 Last sold price

3 beds2 baths2,368 sq ft

4 Oakland Cir, Winchester, MA 01890

Property at 18 Wickham Rd, Winchester, MA 01890, 6 beds, 5 baths

$3,174,500 Last sold price

6 beds5 baths7,005 sq ft

18 Wickham Rd, Winchester, MA 01890

Property at 5 Cutting St, Winchester, MA 01890, 3 beds, 1.5 baths

$1,100,000 Last sold price

3 beds1.5 baths1,414 sq ft

5 Cutting St, Winchester, MA 01890

Property at 666 Main St #206, Winchester, MA 01890, 2 beds, 2 baths

$710,000 Last sold price

2 beds2 baths1,170 sq ft

666 Main St #206, Winchester, MA 01890

Property at 200 Swanton St Unit T11, Winchester, MA 01890, 1 bed, 1 bath

$397,000 Last sold price

1 bed1 bath634 sq ft

200 Swanton St Unit T11, Winchester, MA 01890

Property at 200 Swanton St #239, Winchester, MA 01890, 2 beds, 1 bath

$505,000 Last sold price

2 beds1 bath822 sq ft

200 Swanton St #239, Winchester, MA 01890

Property at 200 Swanton St #402, Winchester, MA 01890, 1 bed, 1 bath

$287,000 Last sold price

1 bed1 bath388 sq ft

200 Swanton St #402, Winchester, MA 01890

Property at 200 Swanton St #432, Winchester, MA 01890, 1 bed, 1 bath

$382,000 Last sold price

1 bed1 bath606 sq ft

200 Swanton St #432, Winchester, MA 01890

Property at 60 Harvard, Winchester, MA 01890, 4 beds, 3 baths

$899,000 Last sold price

4 beds3 baths1,860 sq ft

60 Harvard, Winchester, MA 01890

Property at 5 Emerson Ct, Winchester, MA 01890, 3 beds, 3.5 baths

$1,185,000 Last sold price

3 beds3.5 baths2,000 sq ft

5 Emerson Ct, Winchester, MA 01890

Property at 35 Harvard St, Winchester, MA 01890, 5 beds, 2 baths

$1,250,000 Last sold price

5 beds2 baths1,706 sq ft

35 Harvard St, Winchester, MA 01890

Property at 17 Baldwin St, Winchester, MA 01890, 3 beds, 1.5 baths

$878,000 Last sold price

3 beds1.5 baths1,672 sq ft

17 Baldwin St, Winchester, MA 01890

Property at 235 Cross St, Winchester, MA 01890, 3 beds, 1.5 baths

$868,000 Last sold price

3 beds1.5 baths1,931 sq ft

235 Cross St, Winchester, MA 01890

Property at 171 Swanton St #5, Winchester, MA 01890, 3 beds, 2.5 baths

$900,000 Last sold price

3 beds2.5 baths1,843 sq ft

171 Swanton St #5, Winchester, MA 01890

Property at 171 Swanton St #60, Winchester, MA 01890, 3 beds, 2.5 baths

$738,000 Last sold price

3 beds2.5 baths1,824 sq ft

171 Swanton St #60, Winchester, MA 01890

Property at 50 Lake St Unit B, Winchester, MA 01890, 2 beds, 1.5 baths

$690,000 Last sold price

2 beds1.5 baths1,554 sq ft

50 Lake St Unit B, Winchester, MA 01890

Redfin Corp.

Property at 2 Lagrange St, Winchester, MA 01890, 7 beds, 2.5 baths

$1,900,000 Last sold price

7 beds2.5 baths3,413 sq ft

2 Lagrange St, Winchester, MA 01890

Property at 4 Norwood St, Winchester, MA 01890, 5 beds, 4.5 baths

$3,242,250 Last sold price

5 beds4.5 baths5,250 sq ft

4 Norwood St, Winchester, MA 01890

Property at 5 Stratford Rd, Winchester, MA 01890, 6 beds, 4.5 baths

$3,599,000 Last sold price

6 beds4.5 baths5,876 sq ft

5 Stratford Rd, Winchester, MA 01890

Property at 112 Church St, Winchester, MA 01890, 8 beds, 2.5 baths

$1,600,000 Last sold price

8 beds2.5 baths3,591 sq ft

112 Church St, Winchester, MA 01890

Property at 20 Foxcroft Rd, Winchester, MA 01890, 5 beds, 5.5 baths

$4,450,000 Last sold price

5 beds5.5 baths7,679 sq ft

20 Foxcroft Rd, Winchester, MA 01890

Property at 54 Wedgemere Ave, Winchester, MA 01890, 6 beds, 3.5 baths

$2,862,500 Last sold price

6 beds3.5 baths5,238 sq ft

54 Wedgemere Ave, Winchester, MA 01890

Property at 48 Salisbury St, Winchester, MA 01890, 5 beds, 3.5 baths

$2,600,000 Last sold price

5 beds3.5 baths4,779 sq ft

48 Salisbury St, Winchester, MA 01890

Property at 58 Wedgemere Ave, Winchester, MA 01890, 5 beds, 4.5 baths

$3,450,000 Last sold price

5 beds4.5 baths4,800 sq ft

58 Wedgemere Ave, Winchester, MA 01890

Property at 11 Taft, Winchester, MA 01890, 5 beds, 5.5 baths

$2,750,000 Last sold price

5 beds5.5 baths4,627 sq ft

11 Taft, Winchester, MA 01890

Property at 15 Westland Ave, Winchester, MA 01890, 4 beds, 2.5 baths

$1,750,000 Last sold price

4 beds2.5 baths2,397 sq ft

15 Westland Ave, Winchester, MA 01890

Property at 10 Blossom Hill Rd, Winchester, MA 01890, 4 beds, 2 baths

$1,768,500 Last sold price

4 beds2 baths3,838 sq ft

10 Blossom Hill Rd, Winchester, MA 01890

Property at 5 Thornton Rd, Winchester, MA 01890, 4 beds, 3.5 baths

$1,525,000 Last sold price

4 beds3.5 baths2,755 sq ft

5 Thornton Rd, Winchester, MA 01890

Property at 64 Westland Ave, Winchester, MA 01890, 4 beds, 4 baths

$2,050,000 Last sold price

4 beds4 baths3,716 sq ft

64 Westland Ave, Winchester, MA 01890

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Recently Sold Homes in Winchester

There are currently 65 recently sold homes for sale in Winchester at a median listing price of $1.74M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winchester stay on the market for 41 days and receive 1 offers. Popular neighborhoods include Winchester Town Center, Arlington Heights, West Medford, Arlington Center, and Winchester Highlands. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 25 homes have been sold in Winchester. In addition to houses in Winchester, there were also 6 condos, 9 townhouses, and 4 multi-family units for sale in Winchester last month. Winchester is a minimally walkable city in Middlesex County with a Walk Score of 40. Winchester is home to approximately 21,231 people. Find your dream home in Winchester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winchester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winchester. Our Winchester real estate stats and trends will give you more information about home buying and selling trends in Winchester. If you're looking to sell your home in the Winchester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winchester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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