Winchester Highlands, MA homes for sale & real estate

14 homes

Sort:

Recommended

166 Forest St, Winchester, MA 01890
166 Forest St, Winchester, MA 01890
166 Forest St, Winchester, MA 01890
ABOUT THIS HOME
Winchester Highlands, 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

$1,890,000

5 beds4 baths3,301 sq ft

166 Forest St, Winchester, MA 01890

0.3 acre lot • Garage • Car-dependent

6 Highland Ave, Winchester, MA 01890
6 Highland Ave, Winchester, MA 01890
6 Highland Ave, Winchester, MA 01890
ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
4 BD, 2.5 BA home tucked away from the road for added privacy. Kitchen has spacious dining area for enjoying family meals & entertaining guests. Inviting family room, w/ FP brings warm ambiance & convenient access to the deck, enhancing your indoor-outdoor living experience. Large living/dining area w/ backyard views is a versatile space w/ an open layout make it a welcoming spot. Convenience is key, w/ 1st-floor laundry area & spacious 2-car garage w/ storage. This 0.65-acre lot features a large fenced backyard with a deck, patio, & screened-in gazebo—perfect for relaxing, entertaining, or enjoying outdoor activities. Heated & A/C bonus room on 2nd floor

$1,500,000

4 beds2.5 baths2,506 sq ft

6 Highland Ave, Winchester, MA 01890

0.65 acre lot • 2 garage spots • Car-dependent

NEW CONSTRUCTION3D & VIDEO TOUR

20 Grayson Rd, Winchester, MA 01890
20 Grayson Rd, Winchester, MA 01890
20 Grayson Rd, Winchester, MA 01890
ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Another Tree Top Group masterpiece—where natural light, luxury finishes, & thoughtful design come together in perfect harmony. This 5-bed, 4.5-bath new construction home boasts 9+ ft ceilings, exceptional light fixtures, and a stunning waterfall center island that anchors the designer kitchen w/ custom cabinetry that extends to the ceiling. Custom built-ins & storage throughout. A sleek linear fireplace adds warmth to the open-concept family room. With two primary suites to choose from, flexibility meets luxury. The third-floor primary feels like a private hotel retreat w/ a sitting area, dual walk-in closets, & a spa-inspired bath. The second-floor primary offers a sp

$1,899,000

5 beds4.5 baths3,825 sq ft

20 Grayson Rd, Winchester, MA 01890

6,700 sq ft lot • Car-dependent

HOT HOME

162 Forest St, Winchester, MA 01890
162 Forest St, Winchester, MA 01890
162 Forest St, Winchester, MA 01890
ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Located in the popular Winchester Highlands neighborhood with Elegance and Stature is this 4 bed, 1.5 bath Center Entrance Colonial with 2 car garage, minutes to I-93 and Winchester Center with boutique shops, cafes, restaurants, and newly renovated MBTA Station. Welcoming front vestibule opens to sprawling front-to-back living room with wood burning fireplace and attached sunroom. Formal dining room with chair rail and crown molding leads to 2019 updated kitchen with new gas range, exhaust hood, countertops and hardware. A rear vestibule and mudroom with half bath complete this level. Natural woodwork and crown molding throughout the main level. Mini splits provide comfortable A/C througho

$1,250,000

4 beds1.5 baths1,900 sq ft

162 Forest St, Winchester, MA 01890

0.23 acre lot • 2 garage spots • Car-dependent

60 Harvard, Winchester, MA 01890
60 Harvard, Winchester, MA 01890
60 Harvard, Winchester, MA 01890
ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Exceptional investment opportunity. Located in the heart of desirable Winchester, this multi family property offers a rare opportunity to own a ready to renovate vacant building with incredible potential. Two 1 bedroom, 1 bathroom units and 1 two bedroom unit. This property is primed for a full renovation. Perfect for investors, end users or travellers looking for their own pied-a'-terre, while collecting rents. Property also has a detached 2 car garage with 2nd level. Plenty of off street parking with 3 separate driveways. Bring your vision and unlock the full value of this well located multi-family just minutes from its gorgeous downtown, the commuter rail, schools and local area amenitie

$1,225,000

4 beds3 baths1,860 sq ft

60 Harvard, Winchester, MA 01890

5,397 sq ft lot • 2 garage spots • Somewhat walkable

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

$2,499,000

6 beds4.5 baths4,200 sq ft

14 Grant Rd, Winchester, MA 01890

Property at 15 Mason Way #73, Woburn, MA 01801, 3 beds, 3.5 baths

$1,199,999

3 beds3.5 baths1,921 sq ft

15 Mason Way #73, Woburn, MA 01801

Property at 10 Mason Way #61, Woburn, MA 01801, 3 beds, 2.5 baths

$1,274,995

3 beds2.5 baths2,300 sq ft

10 Mason Way #61, Woburn, MA 01801

Property at 13 Mason Way #72, Woburn, MA 01801, 3 beds, 2.5 baths

$1,299,995

3 beds2.5 baths2,143 sq ft

13 Mason Way #72, Woburn, MA 01801

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

Property at 0 Rockville Park, Stoneham, MA 02180

$4,900,000

0 beds— baths53,000 sq ft

0 Rockville Park, Stoneham, MA 02180

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 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

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

NEW 21 HRS AGO

35 Grape St, Woburn, MA 01801
ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Well maintained 3 bedroom Colonial in a commuters dream location. Easy access to Rte 93, Rte 95, public transportation. Home features 3 spacious bedrooms with hardwood floors throughout, Eat in kitchen with granite counter tops, Spacious lower level family room with 2 additional rooms that could be used as an office or an exercise room.

$780,000

3 beds1.5 baths1,440 sq ft

35 Grape St, Woburn, MA 01801

5,663 sq ft lot • Somewhat walkable

HOT HOME

178 Mystic Valley Pkwy, Winchester, MA 01890
178 Mystic Valley Pkwy, Winchester, MA 01890
178 Mystic Valley Pkwy, Winchester, MA 01890
ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
This carefully crafted Colonial, custom-built by Andrew Pywell, combines solid construction with a bounty of special touches and timeless charm. Delight in sun-splashed living spaces, gleaming hardwood floors, crown moldings, and a layout that balances an open flow, defined spaces and beautifully proportioned rooms across 2,850 square feet. The gracious formal living room, dining room, and inviting family room offer endless entertaining possibilities. The expansive primary suite upstairs includes an ensuite bathroom, walk-in closet/dressing room, walk-in cedar room, and plenty of additional storage. The unfinished attic (with electric!) awaits your design plans! An unfinished basement is p

$1,525,000

3 beds2.5 baths2,850 sq ft

178 Mystic Valley Pkwy, Winchester, MA 01890

6,739 sq ft lot • 2 garage spots • Very walkable

HOT HOME

5 Cutting St, Winchester, MA 01890
5 Cutting St, Winchester, MA 01890
5 Cutting St, Winchester, MA 01890
ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
OFFER DEADLINE TUE JULY 29th 5:00PM | Exceedingly charming + in-town location to be envied. Shops, schools + both MBTA stations at your fingertips. Step up onto your porch, pass the bench swing you’re yet to install; entering into the inviting foyer w/ original stairs preserved & tall ceilings. The main level is sophisticated & functional. A front facing dining room w/ plantation shutters + oversized windows flows into a well laid-out kitchen for the chef in the family! Direct patio access, ½ bath & custom pantry closet + laundry. Beyond your bar/coffee station a sophisticated living room awaits anchored by a gas FP w/ built-ins feat. grass cloth backed glass

$1,075,000

3 beds1.5 baths1,414 sq ft

5 Cutting St, Winchester, MA 01890

5,096 sq ft lot • Very walkable

8 Gigante Dr, Stoneham, MA 02180
8 Gigante Dr, Stoneham, MA 02180
8 Gigante Dr, Stoneham, MA 02180
ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Spacious oversized split-level home in the desirable Nobility Hill neighborhood of Stoneham, MA, located on a quiet cul-de-sac. This 11-room property offers incredible potential with 6 bedrooms, 4 full baths, and flexible living space perfect for extended family or guests. Features include two cozy fireplaces, dual garages, and generous room sizes throughout. A rare opportunity to customize and create your dream home in a sought-after location!

$929,000

6 beds4 baths3,562 sq ft

8 Gigante Dr, Stoneham, MA 02180

0.43 acre lot • 2 garage spots • Somewhat walkable

OPEN THU, 5PM TO 6:30PM

224 Park St Unit C10, Stoneham, MA 02180
224 Park St Unit C10, Stoneham, MA 02180
224 Park St Unit C10, Stoneham, MA 02180
ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Looking for a home that blends CONVENIENCE and a SCENIC SETTING? This UPDATED townhome in Mosley Park offers the best of both! Tucked at the back of the complex, it offers COURTYARD VIEWS in front and a GRASSY AREA framed by trees just off the kitchen—perfect for outdoor dining or relaxing. Inside, enjoy an OPEN-CONCEPT layout with a FIREPLACED LIVING ROOM and a FUNCTIONAL KITCHEN with STAINLESS STEEL appliances & UPGRADED COUNTERTOPS. Upstairs you’ll find TWO SPACIOUS BEDROOMS on 2nd floor and a VERSATILE 3-FL LOFT - ideal as a alternate PRIMARY BEDROOM, OFFICE, STUDIO OR PLAYROOM. The FINISHED LOWER LEVEL adds even more living space and STORAGE. Live the SINGLE-FAMILY LI

$700,000

3 beds1.5 baths2,224 sq ft

224 Park St Unit C10, Stoneham, MA 02180

$567 HOA • Garage • Community pool

NEW CONSTRUCTION

6 Stratton Dr #3208, Woburn, MA 01801
6 Stratton Dr #3208, Woburn, MA 01801
6 Stratton Dr #3208, Woburn, MA 01801
ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Move-in ready condo 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!

$724,995

1 bed1 bath1,129 sq ft

6 Stratton Dr #3208, Woburn, MA 01801

$393 HOA • Garage • Car-dependent

Property at 6 Stratton Dr #303, Woburn, MA 01801, 1 bed, 1 bath

$724,995

1 bed1 bath1,027 sq ft

6 Stratton Dr #303, Woburn, MA 01801

Property at 6 Stratton Dr #3307, Woburn, MA 01801, 2 beds, 2 baths

$924,995

2 beds2 baths1,582 sq ft

6 Stratton Dr #3307, Woburn, MA 01801

Property at Belmont Plan, Woburn, MA 01801, 2 beds, 2 baths

$1,099,995

2 beds2 baths1,796 sq ft

Belmont Plan, Woburn, MA 01801

Listing provided by Zillow

Property at 6 Stratton Dr #408, Woburn, MA 01801, 2 beds, 2 baths

$909,999

2 beds2 baths1,425 sq ft

6 Stratton Dr #408, Woburn, MA 01801

Property at 34 Warren St #3, Stoneham, MA 02180, 3 beds, 1 bath

$675,000

3 beds1 bath1,340 sq ft

34 Warren St #3, Stoneham, MA 02180

Property at 2 Stratton Dr #109, Woburn, MA 01801, 2 beds, 2 baths

$1,100,000

2 beds2 baths1,780 sq ft

2 Stratton Dr #109, Woburn, MA 01801

Property at 11 Skyview Ln, Woburn, MA 01801, 3 beds, 1.5 baths

$754,000

3 beds1.5 baths1,092 sq ft

11 Skyview Ln, Woburn, MA 01801

Property at 544 Main St, Stoneham, MA 02180, 4 beds, 4 baths

$1,379,000

4 beds4 baths2,935 sq ft

544 Main St, Stoneham, MA 02180

Property at 6 Stratton Dr #407, Woburn, MA 01801, 2 beds, 2 baths

$949,999

2 beds2 baths1,582 sq ft

6 Stratton Dr #407, Woburn, MA 01801

Listing provided by Zillow

Property at 6 Stratton Dr #208, Woburn, MA 01801, 1 bed, 1 bath

$699,999

1 bed1 bath1,129 sq ft

6 Stratton Dr #208, Woburn, MA 01801

Listing provided by Zillow

Property at Claremont Plan, Woburn, MA 01801, 1 bed, 1 bath

$749,995

1 bed1 bath1,129 sq ft

Claremont Plan, Woburn, MA 01801

Listing provided by Zillow

Property at Jackson Plan, Woburn, MA 01801, 3 beds, 2.5 baths

$1,049,995

3 beds2.5 baths2,143 sq ft

Jackson Plan, Woburn, MA 01801

Listing provided by Zillow

Property at Southbrook Plan, Woburn, MA 01801, 3 beds, 2.5 baths

$1,074,995

3 beds2.5 baths2,300 sq ft

Southbrook Plan, Woburn, MA 01801

Listing provided by Zillow

Property at 5 Graystone Rd, Stoneham, MA 02180

$449,900

— beds— baths— sq ft

5 Graystone Rd, Stoneham, MA 02180

Average home prices near Winchester Highlands, MA

Cities

Neighborhoods

North Woburn homes for sale
$799,000
West Side homes for sale
$2,139,500
Wyoming homes for sale
$999,500
West Medford homes for sale
$999,000
Wedgemere homes for sale
$2,699,000
Montvale homes for sale
$1,100,000
North Medford homes for sale
$787,000
Woburn Highlands homes for sale
$699,900
Downtown Melrose homes for sale
$794,900
Malden Highlands homes for sale

Winchester Highlands, MA real estate trends

All Home Types trends in Winchester Highlands, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,234,995

+4.6% YoY | Jun 2025

1 year
3 year
5 year

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

Location

Data

Jun 2025

Growth

% YoY

Winchester Highlands, MA

$1,234,995

+4.6%

See more Winchester Highlands, MA market insights

More to explore in Winchester Highlands, MA

How to buy a house in Winchester Highlands, 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

Rocket Mortgage is an affiliated business of Redfin. 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.

Rocket Mortgage, LLC, Rocket Homes Real Estate LLC, Rocket Card, LLC, RockLoans Marketplace LLC (doing business as Rocket Loans), and Rocket Money, Inc., are separate operating subsidiaries of Rocket Limited Partnership. Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company is a separate legal entity operated and managed through its own management and governance structure. Rocket Limited Partnership is an indirect, wholly owned subsidiary of Rocket Companies, Inc. (NYSE: RKT).

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.