Winchester Town Center, MA homes for sale & real estate

18 homes

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OPEN SUN, 11AM TO 1PM

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
Charming townhouse located at The Village, one of Winchester’s most sought-after and impeccably maintained communities, offers 1,843sf of living space. Featuring 3 generously sized bedrooms with full-height ceilings, and 2.5 updated bathrooms, it is one of the largest homes in the community. The home is flooded with natural light thanks to its end-unit position, windows on three sides, and a skylight in the dining area. The freshly painted interior is complemented by refinished hardwood parquet floors, new carpeting in two of the bedrooms, and wood flooring in the third bedroom. The expansive living room is anchored by a wood-burning fireplace, while the open-concept kitchen and dinin

$875,000

3 beds2.5 baths1,843 sq ft

171 Swanton St #5, Winchester, MA 01890

Tennis court • Picturesque grounds • Swimming pool

OPEN SUN, 10AM TO 1PM

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
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 to gather. The living room, graced with crown molding, offers a welcoming space for relaxation and entertainment. Imagine the ambiance created by this classic architectural detail, providing a touch of elegance to your everyday living. The home features three bedrooms and two full bathrooms, alongsi

$1,050,000

4 beds2 baths1,938 sq ft

380 Cross St, Winchester, MA 01890

Built in bookcases • Balcony • Dining area

OPEN SUN, 12PM TO 1PM3D & VIDEO TOUR

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
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 elegant entertaining. The soaring family room stuns with cathedral ceilings, exposed beams, and a floor-to-ceiling stone fireplace—perfect for cozy evenings or lively gatherings. The serene primary suite offers a wood-accented ceiling, sitting area, and spa bath with dual vanities and a

$3,899,000

6 beds4.5 baths6,367 sq ft

40 Foxcroft Rd, Winchester, MA 01890

Cathedral ceilings • Large island • Built-in bar

OPEN SUN, 1PM TO 2:30PMVIDEO TOUR

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
Exceptional value, prime living in this stunning home w/ spectacular resort style back yard surrounded by mature plants and trees encompassing the gorgeous yard/setting. Completely updated throughout w/ custom high end finishes, open floor plan, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive backyard featuring gorgeous patio & maintenance free heated POOL w/ in- floor cleaning system & auto cover! Inviting covered rear porch /gazebo for outdoor living complete with movie night projector! Impressive family rm w/ views of yard, gas fireplace & built in bookshelves . Stylish formal dining rm w/ bay

$2,975,000

6 beds3.5 baths5,238 sq ft

54 Wedgemere Ave, Winchester, MA 01890

Impressive family rm • Gas fireplace • Built in bookshelves

OPEN SUN, 1PM TO 2:30PM

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
This isn’t just a house — it’s a front-row seat to the good life, where you can walk to shops, schools, cafés, restaurants, and everything the town has to offer! This 5-bedroom, 3.5-bath Victorian sits proudly in the heart of Winchester Center, in the highly coveted Lincoln School district. Original hardwood floors, soaring ceilings, and stunning architectural details give this home its timeless character, while the updated kitchen and spacious rooms bring modern comfort to everyday living. With its gorgeous design and generous layout, it’s perfect for hosting friends or enjoying quiet evenings at home. And the best part? The backyard offers a quiet space with

$1,599,000

5 beds3.5 baths2,718 sq ft

77 Washington St, Winchester, MA 01890

Walk to shops • Dining patio • Garden

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

$409,900

1 bed1 bath634 sq ft

200 Swanton St Unit T11, Winchester, MA 01890

Property at 20 Arthur St #20, Winchester, MA 01890, 2 beds, 1 bath

$399,900

2 beds1 bath1,084 sq ft

20 Arthur St #20, Winchester, MA 01890

Property at 4 Wyman Ct #4, Winchester, MA 01890, 4 beds, 4.5 baths

$1,399,000

4 beds4.5 baths2,500 sq ft

4 Wyman Ct #4, Winchester, MA 01890

Property at 2 George Rd #2, Winchester, MA 01890, 3 beds, 2 baths

$662,500

3 beds2 baths1,232 sq ft

2 George Rd #2, Winchester, MA 01890

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

$2,750,000

5 beds3.5 baths4,779 sq ft

48 Salisbury St, Winchester, MA 01890

Property at 19 Glengarry Rd, Winchester, MA 01890, 6 beds, 3.5 baths

$2,099,000

6 beds3.5 baths3,521 sq ft

19 Glengarry Rd, Winchester, MA 01890

Property at 89 Wildwood St, Winchester, MA 01890, 7 beds, 5.5 baths

$2,399,000

7 beds5.5 baths4,829 sq ft

89 Wildwood St, Winchester, MA 01890

Property at 6 Ledgewood Rd, Winchester, MA 01890, 6 beds, 7.5 baths

$3,989,000

6 beds7.5 baths7,330 sq ft

6 Ledgewood Rd, Winchester, MA 01890

Property at 162 Swanton St #162, Winchester, MA 01890, 3 beds, 3.5 baths

$1,275,000

3 beds3.5 baths2,459 sq ft

162 Swanton St #162, Winchester, MA 01890

Property at 7 Sherman Pl #7, Winchester, MA 01890, 4 beds, 2.5 baths

$1,500,000

4 beds2.5 baths2,765 sq ft

7 Sherman Pl #7, Winchester, MA 01890

Property at 382 S Border Rd, Winchester, MA 01890, 6 beds, 5.5 baths

$2,689,000

6 beds5.5 baths4,563 sq ft

382 S Border Rd, Winchester, MA 01890

Property at 4 Chestnut St, Winchester, MA 01890, 4 beds, 4.5 baths

$1,990,000

4 beds4.5 baths4,474 sq ft

4 Chestnut St, Winchester, MA 01890

Property at 44 Cabot St, Winchester, MA 01890, 6 beds, 6.5 baths

$3,099,000

6 beds6.5 baths6,028 sq ft

44 Cabot St, Winchester, MA 01890

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OPEN SUN, 1:30PM TO 3PMHOT HOME

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
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 fo

$1,649,000

5 beds4 baths3,508 sq ft

166 Forest St, Winchester, MA 01890

0.3 acre lot • Garage • Car-dependent

OPEN SUN, 11AM TO 1PM

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
Breathtaking luxury condo just moments from Winchester Center and the commuter rail. This recently updated home offers bright, spacious, one-level living with hardwood floors and custom shutters throughout. The kitchen features quartz countertops, stainless steel appliances–including GE Café range and microwave, an oversized sink, and large peninsula with ample seating flows seamlessly to the adjoining living room with gas fireplace. The nearby pantry offers plenty of storage with stacked laundry adding exceptional convenience. A versatile dining room with large windows provides additional space for flexible use. The primary suite, which includes a walk-in closet and private ba

$999,999

3 beds2 baths1,535 sq ft

16 Park Ave #1, Winchester, MA 01890

2,823 sq ft lot • $300 HOA • Somewhat walkable

OPEN SUN, 11AM TO 12:30PM

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
Step into this charming 3-bedroom home that radiates warmth and character from the moment you arrive. Designed with light-filled living spaces and three generously sized bedrooms, it’s a perfect fit for today’s lifestyle just moments from Winchester Center, award-winning schools, and the commuter rail. The fenced backyard and expansive patio extend your living space outdoors, creating a private oasis for barbecues, gardening, or simply unwinding. Build immediate equity and convenience by adding a first floor bathroom - Plans and renderings in hand (see attached and ask agent for details)! This home isn’t just move-in ready—it’s brimming with potential to make i

$959,000

3 beds1 bath1,425 sq ft

571 Washington St, Winchester, MA 01890

7,418 sq ft lot • 2 garage spots • Car-dependent

OPEN SUN, 12PM TO 1:30PM

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
Extensively renovated and move-in ready, this stunning F-unit townhouse offers 4 bedrooms and 4.5 baths with impeccable detail and modern appeal throughout. The many windows, high ceilings, gleaming hardwood floors, and open design create a warm sun-filled home. You will enjoy the large kitchen and the ability to retreat to the dazzling first-floor primary suite, which provides single floor living in a separate bedroom wing. The living areas feature a dramatic two-sided gas fireplace with floor-to-ceiling stone tile. Enjoy outdoor living on the two expansive decks. The finished walkout lower level includes a sitting room, additional bedroom, and full bath—

$1,950,000

4 beds4.5 baths3,512 sq ft

7 Wainwright Rd #72, Winchester, MA 01890

$1,180 HOA • 2 garage spots • Community pool

OPEN SUN, 12PM TO 1PM3D & VIDEO TOUR

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
Welcome to this charming Cape on a spacious corner lot in Winchester. The main level offers hardwood floors, a front-to-back living room with fireplace and built-ins, a dining room with corner hutch, and a half bath. The kitchen features granite counters, stainless steel appliances, abundant cabinetry, and a breakfast island that opens to the cathedral-ceiling family room. A side entry with mudroom keeps things organized, and a sun-filled three-season porch adds flexible living space. Upstairs you’ll find three bedrooms with hardwood floors, including a primary with walk-in closet, plus a full bath. The finished lower level provides extra living area with a full bath and direct walk-o

$1,125,000

3 beds2.5 baths2,648 sq ft

89 Main St, Winchester, MA 01890

0.24 acre lot • Car-dependent

VIDEO TOUR

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
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 eat-in kitchen with large island & granite countertops as well as a formal dining room with gas fireplace. A living room with custom built-ins & window seat, a family room overlooking the yard, and a bar complete this level. This distinguished residence offers 7 bedrooms and 6 bathrooms

$4,174,000

7 beds4.5 baths7,043 sq ft

2 Everett Ave, Winchester, MA 01890

0.68 acre lot • 3 garage spots • Pool

Property at 27 Blueberry Hill Rd, Woburn, MA 01801, 4 beds, 2.5 baths

$950,000

4 beds2.5 baths2,204 sq ft

27 Blueberry Hill Rd, Woburn, MA 01801

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

$2,999,999

5 beds4.5 baths5,716 sq ft

6 Abby Rd, Winchester, MA 01890

Property at 14 Grant Rd, Winchester, MA 01890, 6 beds, 4.5 baths

$2,399,000

6 beds4.5 baths4,200 sq ft

14 Grant Rd, Winchester, MA 01890

Property at 9 Washington Ave, Woburn, MA 01801, 5 beds, 4 baths

$1,575,000

5 beds4 baths4,578 sq ft

9 Washington Ave, Woburn, MA 01801

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

$3,599,000

6 beds4.5 baths5,876 sq ft

5 Stratford Rd, Winchester, MA 01890

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

$2,849,000

5 beds5.5 baths4,627 sq ft

11 Taft Ln, Winchester, MA 01890

Property at 3 Richmond Park #1, Woburn, MA 01801, 2 beds, 2 baths

$519,900

2 beds2 baths1,528 sq ft

3 Richmond Park #1, Woburn, MA 01801

Property at 92 Arlington Rd, Woburn, MA 01801, 3 beds, 2 baths

$1,195,000

3 beds2 baths2,485 sq ft

92 Arlington Rd, Woburn, MA 01801

Property at 6 Mason Way #63, Woburn, MA 01801, 3 beds, 2.5 baths

$1,304,855

3 beds2.5 baths2,143 sq ft

6 Mason Way #63, Woburn, MA 01801

Property at 2 Mason Way #65, Woburn, MA 01801, 3 beds, 3.5 baths

$1,405,475

3 beds3.5 baths2,909 sq ft

2 Mason Way #65, Woburn, MA 01801

Property at 6 Stratton Dr #310, Woburn, MA 01801, 2 beds, 2 baths

$829,999

2 beds2 baths1,425 sq ft

6 Stratton Dr #310, Woburn, MA 01801

Property at 5 Bacon St, Winchester, MA 01890, 6 beds, 4 baths

$2,245,000

6 beds4 baths4,385 sq ft

5 Bacon St, Winchester, MA 01890

Property at 146 Marble St #213, Stoneham, MA 02180, 2 beds, 1.5 baths

$555,000

2 beds1.5 baths1,345 sq ft

146 Marble St #213, Stoneham, MA 02180

Property at 14 Cross St, Woburn, MA 01801

$795,000

— beds— baths— sq ft

14 Cross St, Woburn, MA 01801

Average home prices near Winchester Town Center, MA

Cities

Neighborhoods

Arlington Heights homes for sale
$1,499,000
Wyoming homes for sale
$695,000
West Medford homes for sale
$1,150,000
West Somerville homes for sale
$1,242,500
East Arlington homes for sale
$1,100,000
Montvale homes for sale
$1,187,450
Woburn Highlands homes for sale
$768,750
Winchester Highlands homes for sale
$1,499,450
Brattle homes for sale
$1,098,500
Malden Highlands homes for sale

Winchester Town Center, MA real estate trends

All Home Types trends in Winchester Town Center, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,350,000

+3.8% YoY | Jul 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jul 2025

Growth

% YoY

Winchester Town Center, MA

$1,350,000

+3.8%

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