Winchester, MA homes for sale & real estate

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NEW 32 MINS AGOVIDEO TOUR

ABOUT THIS HOME
Winchester, MA Homes for Sale
Sophisticated updates and a bright, open layout define this beautifully appointed Winchester Fells home. Generous living spaces and thoughtful design enhance both everyday comfort and entertaining. The gourmet kitchen flows seamlessly into inviting gathering areas, while French doors and multiple outdoor access points create an effortless indoor–outdoor connection. Two dedicated home offices offer outstanding flexibility, and four full baths provide ease and convenience throughout. The front-to-back primary suite serves as a serene retreat with spacious closets and a private ensuite bath. Surrounded by mature landscaping that ensures beauty and privacy, this home combines timeless cha

$1,985,000

4 beds4.5 baths3,263 sq ft

7 Appalachian Rd, Winchester, MA 01890

0.43 acre lot • 2 garage spots • Built 1927

$345,000

1 bed1 bath613 sq ft

200 Swanton St #630, Winchester, MA 01890

$432 HOA • Parking • Community pool

3D WALKTHROUGH

ABOUT THIS HOME
Winchester, MA Homes for Sale
Welcome to 7 Trinity Road, a warm & inviting split level home tucked away on a quiet side street in sought after Winchester. From the moment you step inside, the home feels welcoming & comfortable, offering 3 bed & 2.5 baths with a layout that easily supports both everyday living & entertaining. Your foyer provides a convenient place to arrive home, with direct access to the attached garage. The main level features a bright living room with a wood burning fireplace, perfect for cozy evenings as the holidays approach, along with a dining area & a kitchen that opens to an enclosed sunroom overlooking the backyard, an ideal space to relax or gather with friends. F

$1,188,888

3 beds2.5 baths2,130 sq ft

7 Trinity Rd, Winchester, MA 01890

Generous lot • Private office • Enclosed sunroom

VIDEO TOUR

ABOUT THIS HOME
Winchester, MA Homes for Sale
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. Bring your design id

$1,699,000

4 beds3 baths3,343 sq ft

263 Highland Ave, Winchester, MA 01890

Covered porch • Central ac • Primary suite

ABOUT THIS HOME
Winchester, MA Homes for Sale
This is a great opportunity for a moderate-income eligible family to purchase a home in this beautiful town of Winchester. The duplex has 3 levels of finished living space. Third level is newly finished with a main bedroom suite. Amazing stained-glass windows on the first level, also includes fireplaces in 4 rooms. Loaded with character and charm. See attached application with details regarding deed restrictions.

$449,000

3 beds2.5 baths1,783 sq ft

13 Nelson St #13, Winchester, MA 01890

Fireplaces in rooms • Main bedroom suite • 2 parking spots

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

$1,995,000

5 beds4 baths4,334 sq ft

237 Swanton St, Winchester, MA 01890

Property at 95 Irving St #95, Winchester, MA 01890, 4 beds, 3.5 baths

$1,399,000

4 beds3.5 baths2,490 sq ft

95 Irving St #95, Winchester, MA 01890

Property at 35 Glen Grn, Winchester, MA 01890, 4 beds, 2 baths

$1,999,000

4 beds2 baths3,509 sq ft

35 Glen Grn, Winchester, MA 01890

Property at 139 High St, Winchester, MA 01890, 3 beds, 1.5 baths

$969,000

3 beds1.5 baths1,302 sq ft

139 High St, Winchester, MA 01890

Property at 200 Swanton St #228, Winchester, MA 01890, 1 bed, 1 bath

$399,000

1 bed1 bath606 sq ft

200 Swanton St #228, Winchester, MA 01890

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

$2,299,000

7 beds5.5 baths4,929 sq ft

89 Wildwood St, Winchester, MA 01890

Property at 6 Ivy Cir, Winchester, MA 01890, 6 beds, 4 baths

$2,250,000

6 beds4 baths3,728 sq ft

6 Ivy Cir, Winchester, MA 01890

Property at 16 Ridge St, Winchester, MA 01890, 3 beds, 2.5 baths

$1,149,000

3 beds2.5 baths1,844 sq ft

16 Ridge St, Winchester, MA 01890

Property at 666 Main St #315, Winchester, MA 01890, 2 beds, 2 baths

$699,000

2 beds2 baths1,025 sq ft

666 Main St #315, Winchester, MA 01890

Property at 19 Town Way, Winchester, MA 01890, 5 beds, 5.5 baths

$2,999,000

5 beds5.5 baths5,257 sq ft

19 Town Way, Winchester, MA 01890

Property at 200 Swanton St #234, Winchester, MA 01890, 1 bath

$269,000

0 beds1 bath388 sq ft

200 Swanton St #234, Winchester, MA 01890

Property at 20 Amberwood Dr, Winchester, MA 01890, 6 beds, 7 baths

$3,600,000

6 beds7 baths8,866 sq ft

20 Amberwood Dr, Winchester, MA 01890

Property at 257 High St, Winchester, MA 01890, 5 beds, 6 baths

$3,299,000

5 beds6 baths7,101 sq ft

257 High St, Winchester, MA 01890

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

$380,000

1 bed1 bath634 sq ft

200 Swanton St Unit T28, 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

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NEW CONSTRUCTION

ABOUT THIS HOME
Winchester, MA Homes for Sale
New construction at Highland at Vale in Woburn! The Jackson floor plan offers over 2,900 sq. ft. of well-designed living space, including a finished basement. The bright, open kitchen features abundant cabinetry, stainless steel appliances, and a large island that opens to a spacious gathering room and a distinctive octagon-shaped dining area with bay window. Enjoy wooded views from your private deck, ideal for entertaining or relaxing. The second level includes three bedrooms, highlighted by a luxurious owner’s suite with sitting area, seven windows, double walk-in closets, and a spa-like bath with soaking tub. A second entry with built-in bench and coat closet connects to the two-ca

$1,349,999

3 beds3.5 baths2,909 sq ft

17 Mason Way #74, Woburn, MA 01801

Private deck • Wooded views • Finished basement

NEW CONSTRUCTION

ABOUT THIS HOME
Winchester, MA Homes for Sale
Welcome to the Jameson at Highland at Vale in Woburn! This beautifully designed home is located on the third floor and flooded with natural light, creating a bright and inviting atmosphere. The chef-inspired kitchen boasts stainless steel appliances, a generous oversized island, and an abundance of cabinetry, perfect for culinary enthusiasts. The owner's suite is a serene retreat, featuring an extra-large walk-in closet and a spa-like bathroom for ultimate relaxation. Additionally, a versatile den with french doors offers a private space for work or leisure. With a perfect balance of comfort and style, this home is ideal for modern living! Price includes 1 car garage parking space.

$639,995

1 bed1 bath1,027 sq ft

6 Stratton Dr #303, Woburn, MA 01801

Spa like bathroom • Oversized island • $397 HOA

NEW CONSTRUCTION

ABOUT THIS HOME
Winchester, MA Homes for Sale
Last chance to own a move-in ready home at Highland at Vale in Woburn! The Ivywood home design offers a corner unit filled with natural light. The kitchen, perfect for your inner chef, features stainless steel appliances, an oversized island, and soft-closing cabinets. The open floor plan makes entertaining a breeze—host in the private dining area, then relax in the gathering room. The owner's suite offers a serene retreat with an extra-large walk-in closet and a spa-like bath. Plus, there's plenty of space for guests in the second bedroom. Ideal for modern living, this home combines comfort and style. This stunning home is fully finished, turnkey, and available now!

$889,999

2 beds2 baths1,582 sq ft

6 Stratton Dr #307, Woburn, MA 01801

Open floor plan • Natural light • Corner unit

NEW CONSTRUCTION

ABOUT THIS HOME
Winchester, MA Homes for Sale
Move-in ready condominium at Highland at Vale in Woburn. This is the last Claremont home available in the community! The Claremont is a single-level home design with open flowing rooms and a abundance of natural light. The kitchen, perfect for your inner chef, features stainless steel appliances, an oversized island, and soft-closing cabinets. Spend time watching your favorite shows in the gathering room or soaking up the sun on your private balcony. The customizable flex space comes complete with French doors ensuring privacy. The owner's suite offers a features a spacious walk-in closet. Ideally located just 10 miles from downtown Boston. Underground Garage Parking included!

$699,995

1 bed1 bath1,129 sq ft

6 Stratton Dr #208, Woburn, MA 01801

Move-in ready • Oversized island • $393 HOA

ABOUT THIS HOME
Winchester, MA Homes for Sale
Have you been searching for a completely renovated home in Arlington with high end finishes and great attention to detail? You'll fall in love with 33 Dickson Avenue with its thoughtful layout and bright spaces. Set on a quiet side street close to Stratton elementary school this 10 room, 5 bedroom Colonial boasts a wonderful open floor plan with french doors to the private, landscaped yard. Spacious kitchen features stylish white and wood cabinetry, Thermador stainless steel appliances including a 36" induction range, island & quartz countertops. Gorgeous fireplaced family room & chic marble half bath nearby. Living room & first floor bedroom suite also on the first l

$2,200,000

5 beds5 baths3,706 sq ft

33 Dickson Ave, Arlington, MA 02474

Open floor plan • Thoughtful layout • Bright spaces

ABOUT THIS HOME
Winchester, MA Homes for Sale
Did someone say " Stylish Victorian Cape!" Welcome to 4 Laurel Street, owned and nurtured by same family for 44 years. The home has space for everyone both inside and out!. Enter into a lovely foyer which opens up to formal fireplaced living room, formal dining room with a sitting area included, kitchen with breakfast/bar, wet bar (with private filtering system), sun room for morning coffee, and finally a family room. Upstairs holds the main bedroom and two other bedrooms. There is a full bath on the first floor with laundry and a second full bath on the second floor. Lower Level has two rooms, one is being used as an at home office and the second a guest room. Hardwood flooring,

$899,000

3 beds2 baths2,005 sq ft

4 Laurel St, Woburn, MA 01801

Formal dining room • Sun room • 0.25 acre lot

Property at 218 Lowell St, Lexington, MA 02420, 5 beds, 5.5 baths

$1,575,000

5 beds5.5 baths4,290 sq ft

218 Lowell St, Lexington, MA 02420

Property at 588 Main St Unit 3C, Stoneham, MA 02180, 2 beds, 1 bath

$379,000

2 beds1 bath855 sq ft

588 Main St Unit 3C, Stoneham, MA 02180

Property at 30 Whipple Rd, Lexington, MA 02420, 6 beds, 6 baths

$4,195,000

6 beds6 baths7,827 sq ft

30 Whipple Rd, Lexington, MA 02420

Property at 5-9 Rockville Park, Stoneham, MA 02180

$3,450,000

0 beds— baths53,000 sq ft

5-9 Rockville Park, Stoneham, MA 02180

Property at 14 Chruch Ave Unit 2A, Woburn, MA 01801, 1 bed, 1 bath

$310,000

1 bed1 bath500 sq ft

14 Chruch Ave Unit 2A, Woburn, MA 01801

Property at 36 Cambridge Rd #40, Woburn, MA 01801, 2 beds, 2 baths

$690,000

2 beds2 baths1,338 sq ft

36 Cambridge Rd #40, Woburn, MA 01801

Property at 52 Pleasant St, Woburn, MA 01801, 5 beds, 2.5 baths

$1,279,000

5 beds2.5 baths3,932 sq ft

52 Pleasant St, Woburn, MA 01801

Property at 7 Prospect St, Woburn, MA 01801, 7 beds, 7 baths

$1,249,900

7 beds7 baths6,700 sq ft

7 Prospect St, Woburn, MA 01801

Property at 14 Liana St, Woburn, MA 01801, 6 beds, 7.5 baths

$2,749,000

6 beds7.5 baths7,213 sq ft

14 Liana St, 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 14 Church Ave, Woburn, MA 01801, 5 beds, 4 baths

$1,498,000

5 beds4 baths3,276 sq ft

14 Church Ave, Woburn, MA 01801

Property at 22 Tyler Rd, Lexington, MA 02420, 6 beds, 5.5 baths

$3,650,000

6 beds5.5 baths5,531 sq ft

22 Tyler Rd, Lexington, MA 02420

Property at 39 Garfield Ave, Woburn, MA 01801, 4 beds, 2 baths

$749,000

4 beds2 baths2,178 sq ft

39 Garfield Ave, Woburn, MA 01801

Average home prices near Winchester, MA

Cities

Neighborhoods
Zip Codes

Winchester Town Center homes for sale
$749,500
Arlington Heights homes for sale
$1,354,450
West Medford homes for sale
$847,450
Symmes Corner homes for sale
Wedgemere homes for sale
$2,499,000
Countryside homes for sale
$3,695,000
Winchester Highlands homes for sale
$1,349,999
Woburn Highlands homes for sale
$687,000
The Flats homes for sale
$2,124,500
Downtown Woburn homes for sale
$702,000

Winchester, MA real estate trends

All Home Types trends in Winchester, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,250,000

-24.2% YoY | Nov 2025

1 year
3 year
5 year

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

Location

Data

Nov 2025

Growth

% YoY

Winchester, MA

$1,250,000

-24.2%

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