Winchester Town Center, MA homes for sale & real estate

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OPEN TODAY, 5PM TO 6:30PM

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
With 6 bedrooms & 5 full baths, this beautifully crafted new construction located at the end of a cul-de-sac delivers refined style, a modern layout & effortless living. The open layout showcases a chef’s kitchen with an oversized island, quartz counters & Thermador appliances, seamlessly connecting to the dining & living rooms, both with their own gas fireplace. Detailed millwork, coffered ceilings & built-ins elevate every space. A 1st floor bedroom provides flexibility for guests or a home office. The 2nd floor features 5 bright, airy bedrooms including a serene primary suite with tray ceiling, spa-like bath, soaking tub, walk-in shower & custom

$2,399,000

6 beds5 baths4,594 sq ft

29 Shepard Ct, Winchester, MA 01890

Quartz counters • Gas fireplace • Cul-de-sac

HOT HOME

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
One of Winchester’s most beloved neighborhoods sets the tone for 30 Prospect Street, a beautifully reimagined home transformed by an extensive remodel less than five years ago. A spectacular, fully renovated Chef's kitchen anchors the main level with high-end finishes and a seamless flow for living and entertaining. The living room is sunny and inviting, featuring an impressive fireplace, timeless details, and a beautiful view of the gorgeous backyard. The adjoining dining room offers a refined space for gatherings with its classic architectural charm. The new primary suite includes a spa-inspired bath and custom walk-in closet, while additional bathrooms have been fully renewed with

$2,099,000

4 beds3 baths2,519 sq ft

30 Prospect St, Winchester, MA 01890

Spa-inspired bath • Impressive fireplace • Chef's kitchen

OPEN SAT, 12PM TO 1:30PM

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
Welcome to 89 Wildwood — Winchester’s best new value, where modern design meets classic New England charm! This new construction home offers a flexible layout with spaces for hosting, relaxing & everyday living. The chef’s kitchen impresses with an oversized island, stylish finishes, ample cabinetry & opens to a designated dining area. Fireplaced family room, bedroom/office with ensuite & half bath complete the first level. Upstairs, find five bedrooms, three full bathrooms & a laundry room outfitted with custom cabinetry & sink. The front to back primary suite has double walk in closets & an ensuite with dual vanities. Finished lower le

$2,299,000

7 beds5.5 baths4,929 sq ft

89 Wildwood St, Winchester, MA 01890

Oversized island • Chef's kitchen • 0.23 acre lot

OPEN SAT, 11AM TO 12PM

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

$1,399,000

4 beds4.5 baths2,500 sq ft

4 Wyman Ct #4, Winchester, MA 01890

Private deck • Wet bar • Full gut renovation

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
Sunny studio unit overlooking the pond and courtyard at Parkview Condos in Winchester. Unit features include large private balcony with large sliding door that lets in lots of natural sun light. New LVP flooring in the living room/bedroom area and hallway. Freshly painted all throughout. Kitchen has granite countertops and a new refrigerator and electric range. The condominium amenities include an in-ground swimming pool, barbecue area, large parking area with additional overnight guest parking, on-site laundry, on-site management, and private storage units. Ideally located near downtown Winchester, the commuter rail, and major highways.

$269,000

0 beds1 bath388 sq ft

200 Swanton St #234, Winchester, MA 01890

Barbecue area • Private balcony • Granite countertops

Property at 8 Felsdale Close, Winchester, MA 01890, 4 beds, 2.5 baths

$2,075,000

4 beds2.5 baths3,658 sq ft

8 Felsdale Close, Winchester, MA 01890

Property at 237 Swanton St, Winchester, MA 01890, 5 beds, 4 baths

$2,149,000

5 beds4 baths4,334 sq ft

237 Swanton St, Winchester, MA 01890

Property at 200 Swanton St Unit T28, Winchester, MA 01890, 1 bed, 1 bath

$385,000

1 bed1 bath634 sq ft

200 Swanton St Unit T28, Winchester, MA 01890

Property at 15 Wildwood St, Winchester, MA 01890, 6 beds, 2.5 baths

$2,275,000

6 beds2.5 baths4,104 sq ft

15 Wildwood St, Winchester, MA 01890

Property at 666 Main St #312, Winchester, MA 01890, 2 beds, 2 baths

$799,999

2 beds2 baths1,240 sq ft

666 Main St #312, Winchester, MA 01890

Property at 40 Foxcroft Rd, Winchester, MA 01890, 6 beds, 4.5 baths

$3,799,000

6 beds4.5 baths6,367 sq ft

40 Foxcroft Rd, 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

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

$389,900

2 beds1 bath1,084 sq ft

20 Arthur St #20, Winchester, MA 01890

Property at 380 Cross St, Winchester, MA 01890, 4 beds, 2 baths

$949,000

4 beds2 baths1,938 sq ft

380 Cross St, 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

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OPEN SAT, 11AM TO 12:30PM

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
This stately Victorian offers an exceptional blend of preserved character and modern functionality across its generous, well-appointed layout. Sunlit rooms highlight hardwood floors, detailed millwork, bay windows, and a graceful fireplace, creating a warm and elegant flow throughout the main level. The expansive kitchen features stone counters, a central island, French doors, and direct access to the porch and patio for effortless indoor-outdoor living. Upper levels provide inviting bedrooms, including a spacious primary suite with its own bath, walk-in closet and balcony. A versatile third-floor retreat/ legal apartment with treetop views—complete with additional kitchen, living are

$2,275,000

6 beds3.5 baths4,122 sq ft

7-7A Brooks St, Winchester, MA 01890

0.63 acre lot • 2 garage spots • Car-dependent

OPEN TODAY, 5PM TO 6:30PM3D WALKTHROUGH

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artful lighting to the seamless flow of the open yet intentionally defined floor plan. The impressive kitchen and dining area form the heart of the home—perfectly suited for lively entertaining, relaxed gatherings, and everyday living. Upstairs, the primary suite offers a luxurious retreat, while the spacious third-floor teen suite provides comfort, privacy, and versatility. The finished low

$2,999,000

5 beds5.5 baths5,257 sq ft

19 Town Way, Winchester, MA 01890

0.23 acre lot • 2 garage spots • Community pool

OPEN SAT, 1PM TO 2PM3D & VIDEO TOUR

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Café appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a sitting area complete this level. The third floor provides space for additional bedrooms or an office. The finished lower level includes a family room, wine cellar, sauna, gym, and full bath. Enjoy a tree-lined backyard with deck and hot tub, perfect for entertaining. The home office ope

$1,869,000

5 beds3.5 baths3,294 sq ft

20 Grove Pl, Winchester, MA 01890

0.29 acre lot • 2 garage spots • Car-dependent

OPEN SAT, 12PM TO 1:30PM

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to entertain. Enjoy morning coffee or evening relaxation on the unheated 3-season porch overlooking the yard, with seasonal views of the Boston skyline. The lower level features high ceilings with a heating and cooling unit already installed, offering great potential for 200+ sqft of future finished space.

$999,000

3 beds1.5 baths1,302 sq ft

139 High St, Winchester, MA 01890

0.51 acre lot • Garage • Car-dependent

VIDEO TOUR

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
Updated 3 bed, 2.5 bath home * Set on a generous 11K lot * in a fantastic Winchester location/ Lincoln Elementary close to town, schools, the train, and route to Boston. The first floor offers an ideal layout with an updated kitchen, stainless steel appliances & island w seating open to a lovely family room flooded with sunlight, plus a spacious living room w fplc and dining room. A 3 season sunroom in the rear provides bonus living space with direct access to the large back & side yards, perfect for entertaining, gardening, or outdoor play. The second floor features three bedrooms, including a primary suite with a private bath. The partially finished basement offers flexible

$1,350,000

3 beds2.5 baths2,153 sq ft

6 Marchant Rd, Winchester, MA 01890

0.26 acre lot • Garage • Community pool

NEW CONSTRUCTION

ABOUT THIS HOME
Winchester Town Center, MA Homes for Sale
New Construction at Highland at Vale in Woburn! Ideally located off Montvale Avenue, just 10 miles from downtown Boston, Highland at Vale offers new homes in a highly desired setting with easy access to everyday conveniences, shopping, and entertainment. Choose from a variety of innovative single-level and 2-story townhome designs featuring open-concept layouts. The Jameson is a Life Tested® design built with your everyday needs in mind, offering a versatile flex room with French doors, a beautiful kitchen, and an oversized gathering room perfect for entertaining. The luxurious Owner’s Suite provides a relaxing retreat with exceptional comfort and style. Includes 1 garage parking

$659,995

1 bed1 bath1,027 sq ft

6 Stratton Dr #404, Woburn, MA 01801

$397 HOA • Garage • Car-dependent

Property at 19 Mason Way #75, Woburn, MA 01801, 3 beds, 3.5 baths

$1,349,999

3 beds3.5 baths2,909 sq ft

19 Mason Way #75, Woburn, MA 01801

Property at 02 Mason Way #06524, Woburn, MA 01801, 3 beds, 3.5 baths

$1,299,999

3 beds3.5 baths2,909 sq ft

02 Mason Way #06524, Woburn, MA 01801

Property at 06 Mason Way #06324, Woburn, MA 01801, 3 beds, 2.5 baths

$1,149,999

3 beds2.5 baths2,143 sq ft

06 Mason Way #06324, Woburn, MA 01801

Property at 59 Katherine Rd, Stoneham, MA 02180, 3 beds, 1.5 baths

$674,000

3 beds1.5 baths1,301 sq ft

59 Katherine Rd, Stoneham, MA 02180

Property at 8 Priscilla Ln, Winchester, MA 01890, 5 beds, 5.5 baths

$3,250,000

5 beds5.5 baths6,500 sq ft

8 Priscilla Ln, Winchester, MA 01890

Property at 53 Winford Way, Winchester, MA 01890, 5 beds, 4 baths

$2,799,000

5 beds4 baths5,083 sq ft

53 Winford Way, Winchester, MA 01890

Property at 53 Bacon St, Winchester, MA 01890, 3 beds, 2.5 baths

$1,499,000

3 beds2.5 baths2,865 sq ft

53 Bacon St, Winchester, MA 01890

Property at 80 Arlington St, Winchester, MA 01890, 5 beds, 3.5 baths

$3,099,000

5 beds3.5 baths5,632 sq ft

80 Arlington St, Winchester, MA 01890

Property at 6 Stratton Dr #307, Woburn, MA 01801, 2 beds, 2 baths

$899,999

2 beds2 baths1,582 sq ft

6 Stratton Dr #307, Woburn, MA 01801

Property at 571 Washington St, Winchester, MA 01890, 3 beds, 1 bath

$898,000

3 beds1 bath1,425 sq ft

571 Washington St, Winchester, MA 01890

Property at 2 Everett Ave, Winchester, MA 01890, 7 beds, 4.5 baths

$4,174,000

7 beds4.5 baths7,043 sq ft

2 Everett Ave, Winchester, MA 01890

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

$1,499,000

5 beds4 baths4,578 sq ft

9 Washington Ave, Woburn, MA 01801

Property at 20 Goodwin Dr, Woburn, MA 01801, 3 beds, 2.5 baths

$1,099,999

3 beds2.5 baths2,300 sq ft

20 Goodwin Dr, Woburn, MA 01801

Listing provided by Zillow

Average home prices near Winchester Town Center, MA

Cities

Neighborhoods

North Woburn homes for sale
$1,249,900
Arlington Heights homes for sale
$1,359,900
West Medford homes for sale
$995,000
West Somerville homes for sale
$1,237,500
East Arlington homes for sale
$949,000
Burlington Town Center homes for sale
$859,000
Montvale homes for sale
$894,950
Winchester Highlands homes for sale
$1,149,999
Brattle homes for sale
$1,096,750
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)

$975,000

+8.3% YoY | Oct 2025

1 year
3 year
5 year

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

Location

Data

Oct 2025

Growth

% YoY

Winchester Town Center, MA

$975,000

+8.3%

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