Winchester, MA homes for sale & real estate

44 homes

Sort:

Recommended

NEW 1 DAY AGOVIDEO TOUR

ABOUT THIS HOME
Winchester, MA Homes for Sale
A rare opportunity to own one of The Flats’ most celebrated homes! This 1930s Colonial Revival w/ classic curb appeal & elegant proportions sits on over ½ acre of estate-like grounds featuring heated pool, patios, pergola & multiple areas for effortless entertaining. Inside, a grand foyer & sweeping staircase introduce gracious rooms w/ exquisite millwork & superb flow, equally suited for relaxed family living or refined gatherings. Highlights include eat-in chef’s kitchen w/ island & timeless finishes, butler’s pantry, stately dining rm, large living & family rms & private study. Upstairs offers a luxurious primary suite w/

$4,399,000

5 beds5.5 baths7,679 sq ft

20 Foxcroft Rd, Winchester, MA 01890

Studio gym • Wine cellar • Butler's pantry

ABOUT THIS HOME
Winchester, MA Homes for Sale
NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. Formal dining room & dramatic oversized family room will impress, featuring vaulted ceilings, gas fireplace and plenty of windows. The first floor also includes a bedroom suite w/ full bath! Upstairs you'll find 3 spacious bedrooms, including the primary suite w/ walk-in closet & beautiful en-suite bath w/ large shower, tub & double vanity sinks. Additional BR5

$2,399,000

5 beds4 baths4,334 sq ft

237 Swanton St, Winchester, MA 01890

Custom cabinetry • Eat in kitchen • Stainless appliances

ABOUT THIS HOME
Winchester, 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

ABOUT THIS HOME
Winchester, 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 SAT, 1:30PM TO 2:30PM3D & VIDEO TOUR

ABOUT THIS HOME
Winchester, 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

Property at 16 Park Ave #1, Winchester, MA 01890, 3 beds, 2 baths

$999,999

3 beds2 baths1,535 sq ft

16 Park Ave #1, Winchester, MA 01890

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

$959,000

3 beds1 bath1,425 sq ft

571 Washington St, Winchester, MA 01890

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 89 Main St, Winchester, MA 01890, 3 beds, 2.5 baths

$1,125,000

3 beds2.5 baths2,648 sq ft

89 Main 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 257 High St, Winchester, MA 01890, 5 beds, 6 baths

$3,499,000

5 beds6 baths7,101 sq ft

257 High St, 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 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 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 5 Azalea Rd, Winchester, MA 01890, 5 beds, 3.5 baths

$2,199,000

5 beds3.5 baths6,232 sq ft

5 Azalea Rd, 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 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 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 7 Thornberry Rd, Winchester, MA 01890, 5 beds, 2 baths

$1,379,000

5 beds2 baths3,033 sq ft

7 Thornberry 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 59 Johnson Rd, Winchester, MA 01890, 3 beds, 2.5 baths

$1,249,900

3 beds2.5 baths2,458 sq ft

59 Johnson Rd, Winchester, MA 01890

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

$1,249,000

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 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 26 Swan Rd, Winchester, MA 01890, 6 beds, 6.5 baths

$3,199,000

6 beds6.5 baths8,463 sq ft

26 Swan Rd, Winchester, MA 01890

Property at 276 High St, Winchester, MA 01890, 5 beds, 3.5 baths

$2,350,000

5 beds3.5 baths5,006 sq ft

276 High St, Winchester, MA 01890

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

$995,000

4 beds3 baths1,860 sq ft

60 Harvard, Winchester, MA 01890

Property at 20 Grove Pl, Winchester, MA 01890, 5 beds, 3.5 baths

$1,879,000

5 beds3.5 baths3,294 sq ft

20 Grove Pl, Winchester, MA 01890

Property at 61 Grove St, Winchester, MA 01890, 5 beds, 4.5 baths

$2,239,000

5 beds4.5 baths4,798 sq ft

61 Grove St, Winchester, MA 01890

Property at 4 Aricia Ln, Winchester, MA 01890, 4 beds, 4 baths

$1,729,000

4 beds4 baths5,361 sq ft

4 Aricia Ln, 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 58 Bacon St, Winchester, MA 01890, 6 beds, 5.5 baths

$2,195,000

6 beds5.5 baths5,791 sq ft

58 Bacon St, Winchester, MA 01890

Property at 5 Squire Rd, Winchester, MA 01890, 6 beds, 3.5 baths

$2,000,000

6 beds3.5 baths4,696 sq ft

5 Squire Rd, Winchester, MA 01890

Property at 10 Sheffield Rd, Winchester, MA 01890, 7 beds, 5.5 baths

$2,799,000

7 beds5.5 baths5,864 sq ft

10 Sheffield Rd, Winchester, MA 01890

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

$1,349,900

5 beds2 baths1,706 sq ft

35 Harvard St, Winchester, MA 01890

Property at 19 Laurel Hill Ln, Winchester, MA 01890, 5 beds, 4.5 baths

$2,550,000

5 beds4.5 baths3,800 sq ft

19 Laurel Hill Ln, Winchester, MA 01890

Viewing page 1 of 2

Average home prices near Winchester, MA

Cities

Neighborhoods
Zip Codes

Winchester Town Center homes for sale
$1,500,000
West Side homes for sale
$2,049,000
Arlington Heights homes for sale
$1,549,450
West Medford homes for sale
$1,120,000
Morningside homes for sale
$1,375,000
Wedgemere homes for sale
$2,239,000
Montvale homes for sale
$1,187,450
Woburn Highlands homes for sale
$768,750
Winchester Highlands homes for sale
$1,499,450
Downtown Woburn homes for sale
$664,500

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)

$1,220,000

-7.3% YoY | Aug 2025

1 year
3 year
5 year

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

Location

Data

Aug 2025

Growth

% YoY

Winchester, MA

$1,220,000

-7.3%

See more Winchester, MA market insights

More to explore in Winchester, MA

How to buy a house in Winchester, MA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Massachusetts

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Countries

United States

Canada

Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.