Winchester, MA homes for sale & real estate

40 homes

Sort:

Recommended

VIDEO TOUR

21 Fernway, Winchester, MA 01890
21 Fernway, Winchester, MA 01890
21 Fernway, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
Exceptional colonial on Myopia Hill showcasing an expansive rear family room addition, perfectly situated on an idyllic lot surrounded by lush gardens & mature landscape. This stately residence offers a true private oasis just minutes from all conveniences. Rich in finish, elegant in design w/ stunning living areas, large scale rooms & 4 fireplaces creating warm inviting spaces for every day living & entertaining. The custom kitchen leads to dramatic family room w/ vaulted ceiling & walls of windows w/ fireplace & access to expansive patio w/ breathtaking views; seamlessly blending indoor & outdoor living. A formal dining room just off the kitchen provide

$2,899,000

5 beds4.5 baths5,386 sq ft

21 Fernway, Winchester, MA 01890

0.46 acre lot • 2 garage spots • Car-dependent

3D & VIDEO TOUR

14 Grant Rd, Winchester, MA 01890
14 Grant Rd, Winchester, MA 01890
14 Grant Rd, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester’s most desirable neighborhoods. Designed for modern lifestyles, this home features a chef’s kitchen that flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. A sun-drenched 3-season porch expands your living space and offers a peaceful retreat. Enjoy the flexibility of dual primary suites on both the first & second floors, providing exceptional layout options for multi-generational living or guest accommodations. The mudroom w/ dual closets adds everyday functionality and style, while th

$2,499,000

6 beds4.5 baths4,200 sq ft

14 Grant Rd, Winchester, MA 01890

0.23 acre lot • 2 garage spots • Car-dependent

29 Vine St #8, Winchester, MA 01890
29 Vine St #8, Winchester, MA 01890
29 Vine St #8, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
Ideally located for commuters, this stylish 2-bed, 1.5-bath condo sits in the heart of vibrant downtown Winchester—just steps from the Commuter Rail for a quick ride into Boston. Enjoy easy access to major routes and nearby Sheepfold Park for weekend recreation. The main level boasts a sunlit living room with vaulted ceilings and a dedicated dining area, and a sleek kitchen with stainless steel appliances. A convenient half bath completes the main floor. Unwind on your private rooftop balcony—the perfect place to relax after a long day. Upstairs offers two generously sized bedrooms with ample closet space, a full bath, and in-unit laundry. Basement storage adds to the appeal. A

$625,000

2 beds1.5 baths1,157 sq ft

29 Vine St #8, Winchester, MA 01890

$544 HOA • Walker's paradise

3D & VIDEO TOUR

4 Aricia Ln, Winchester, MA 01890
4 Aricia Ln, Winchester, MA 01890
4 Aricia Ln, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
Tucked into the tree-lined enclave of Aricia Lane, this striking contemporary residence delivers bold architectural design, abundant light, and the seamless indoor-outdoor living today’s buyers crave. Set on nearly half an acre in one of Winchester’s most peaceful pockets, this home is a rare fusion of modern comfort, space, and convenience offering the rarest of features: a five-car garage. From the moment you arrive, the home’s curb appeal, rolling lawn, and mature plantings make a lasting impression. Inside, the home showcases soaring vaulted ceilings, skylights, and oversized windows that flood the space with natural light. The open-concept living, dining, and family r

$1,900,000

4 beds4 baths5,361 sq ft

4 Aricia Ln, Winchester, MA 01890

0.46 acre lot • 5 garage spots • Community pool

4 Norwood St, Winchester, MA 01890
4 Norwood St, Winchester, MA 01890
4 Norwood St, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town center with easy access to Boston, this home features exquisite millwork, custom built-ins, and premium finishes throughout. The main home offers 4 bedrooms, 3.5 bathrooms, a living room, dining room, sitting room, pantry, and a bar alcove, along with an expansive second-floor office/flex space. A separate but attached ADU—perfect for extended family or guests—boasts soaring 13’6” ceilings, a grand entertaining area with chandeliers, a full kitchen, and a private guest primary suite. With every imaginable bell and whistle, this home is truly one of

$3,399,000

5 beds4.5 baths5,250 sq ft

4 Norwood St, Winchester, MA 01890

0.26 acre lot • 2 garage spots • Very walkable

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 85 Loring Ave, Winchester, MA 01890, 3 beds, 2.5 baths

$1,379,000

3 beds2.5 baths2,340 sq ft

85 Loring Ave, Winchester, MA 01890

Property at 4 Fieldstone Dr, Winchester, MA 01890, 5 beds, 3.5 baths

$2,190,000

5 beds3.5 baths4,378 sq ft

4 Fieldstone Dr, Winchester, MA 01890

Property at 58 Bacon St, Winchester, MA 01890, 6 beds, 5.5 baths

$2,295,000

6 beds5.5 baths5,791 sq ft

58 Bacon St, Winchester, MA 01890

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

$2,399,000

6 beds4 baths3,728 sq ft

6 Ivy Cir, Winchester, MA 01890

Property at 9 Lakeview Ter, Winchester, MA 01890, 5 beds, 3.5 baths

$4,250,000

5 beds3.5 baths4,484 sq ft

9 Lakeview Ter, Winchester, MA 01890

Property at 1 Fox Hunt Ln, Winchester, MA 01890, 5 beds, 5 baths

$2,250,000

5 beds5 baths5,000 sq ft

1 Fox Hunt Ln, Winchester, MA 01890

Property at 107 Cambridge St, Winchester, MA 01890, 6 beds, 4.5 baths

$2,599,000

6 beds4.5 baths5,824 sq ft

107 Cambridge St, Winchester, MA 01890

Property at 17 Wagon Wheel Rd, Winchester, MA 01890, 5 beds, 5 baths

$2,349,900

5 beds5 baths3,940 sq ft

17 Wagon Wheel Rd, Winchester, MA 01890

Property at 8 Garfield Ave, Winchester, MA 01890, 3 beds, 2 baths

$1,099,000

3 beds2 baths1,536 sq ft

8 Garfield Ave, 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 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 162 Swanton St #162, Winchester, MA 01890, 3 beds, 3.5 baths

$1,299,000

3 beds3.5 baths2,136 sq ft

162 Swanton St #162, Winchester, MA 01890

Property at 10 Girard Rd, Winchester, MA 01890, 3 beds, 1.5 baths

$1,349,000

3 beds1.5 baths3,335 sq ft

10 Girard Rd, Winchester, MA 01890

Property at 44 Amberwood Dr, Winchester, MA 01890, 3 beds, 2.5 baths

$1,765,300

3 beds2.5 baths3,002 sq ft

44 Amberwood Dr, 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

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

$724,999

2 beds2 baths1,170 sq ft

666 Main St #206, Winchester, MA 01890

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

$2,899,000

7 beds5.5 baths5,864 sq ft

10 Sheffield Rd, Winchester, MA 01890

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

$3,249,000

6 beds6.5 baths6,028 sq ft

44 Cabot St, Winchester, MA 01890

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

$3,999,000

6 beds4.5 baths6,367 sq ft

40 Foxcroft Rd, Winchester, MA 01890

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

$3,475,000

5 beds3.5 baths5,632 sq ft

80 Arlington St, Winchester, MA 01890

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

$3,099,000

6 beds3.5 baths5,238 sq ft

54 Wedgemere Ave, Winchester, MA 01890

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

$2,499,000

7 beds5.5 baths4,829 sq ft

89 Wildwood St, Winchester, MA 01890

Property at 11 Fieldstone Dr, Winchester, MA 01890, 5 beds, 4.5 baths

$2,899,000

5 beds4.5 baths6,904 sq ft

11 Fieldstone Dr, Winchester, MA 01890

Property at 147 Highland Ave, Winchester, MA 01890, 3 beds, 2 baths

$1,299,000

3 beds2 baths1,884 sq ft

147 Highland Ave, Winchester, MA 01890

Property at Lot 3 Abby Rd, Winchester, MA 01890, 5 beds, 4.5 baths

$2,999,999

5 beds4.5 baths5,716 sq ft

Lot 3 Abby Rd, Winchester, MA 01890

Property at 7 Thornberry Rd, Winchester, MA 01890, 5 beds, 2 baths

$1,449,900

5 beds2 baths3,033 sq ft

7 Thornberry Rd, Winchester, MA 01890

Property at 14 Hillside Ave, Winchester, MA 01890, 3 beds, 2.5 baths

$1,499,000

3 beds2.5 baths2,605 sq ft

14 Hillside Ave, Winchester, MA 01890

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

$2,899,000

5 beds5.5 baths4,627 sq ft

11 Taft Dr, Winchester, MA 01890

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

$2,349,000

4 beds3.5 baths4,959 sq ft

5 Azalea Rd, Winchester, MA 01890

Property at 11 Viking Rd, Winchester, MA 01890, 7 beds, 7.5 baths

$3,799,900

7 beds7.5 baths7,429 sq ft

11 Viking Rd, Winchester, MA 01890

Property at 71 Woodside Rd, Winchester, MA 01890, 4 beds, 1.5 baths

$1,295,000

4 beds1.5 baths2,202 sq ft

71 Woodside Rd, Winchester, MA 01890

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

$3,698,000

6 beds7 baths8,866 sq ft

20 Amberwood Dr, Winchester, MA 01890

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

$3,989,000

6 beds6.5 baths8,463 sq ft

26 Swan Rd, Winchester, MA 01890

Property at 54 Johnson Rd, Winchester, MA 01890, 7 beds, 7.5 baths

$3,699,000

7 beds7.5 baths7,982 sq ft

54 Johnson Rd, Winchester, MA 01890

Viewing page 1 of 1

Average home prices near Winchester, MA

Cities

Neighborhoods
Zip Codes

Arlington Heights homes for sale
$1,289,000
West Medford homes for sale
$999,000
Lawrence Estates homes for sale
$1,094,450
Wedgemere homes for sale
$3,187,000
Morningside homes for sale
$1,632,500
Montvale homes for sale
$1,100,000
Countryside homes for sale
$4,250,000
Winchester Highlands homes for sale
$1,299,995
Woburn Highlands homes for sale
$754,000
Downtown Woburn homes for sale
$754,000

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)

$1,785,000

+15.4% YoY | May 2025

1 year
3 year
5 year

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

Location

Data

May 2025

Growth

% YoY

Winchester, MA

$1,785,000

+15.4%

See more Winchester, MA market insights

More to explore in Winchester, MA

Featured
Price
Bedroom

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. For additional information on Rocket Mortgage or to receive lending services in the State of New York, please visit RocketMortgage.com.

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.