Winchester Highlands, MA homes for sale & real estate

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OPEN FRI, 12PM TO 1:30PM

ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Best valued single family in Winchester with incredible fenced backyard and expansive patio extending your living space outdoors, and 2 car garage!! Build immediate equity and convenience by adding an additional bathroom - Plans and renderings in hand (see attached and ask agent for details)! Designed with light-filled living spaces and three generously sized bedrooms, it’s a perfect fit for today’s lifestyle just moments from Winchester Center, award-winning schools, and the commuter rail. NEW roof, NEW walkway & patio, NEW hot water heater, NEW fence, NEW garage doors, NEW insulation, Updated kitchen, refinished hardwood floors, gas cooking, and immaculate throughout. ..

$959,000

3 beds1 bath1,425 sq ft

571 Washington St, Winchester, MA 01890

Commuter rail • Private oasis • Expansive patio

OPEN SUN, 11AM TO 12PM3D & VIDEO TOUR

ABOUT THIS HOME
Winchester Highlands, 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

$2,399,000

6 beds4.5 baths4,200 sq ft

14 Grant Rd, Winchester, MA 01890

Flex space • Chef's kitchen • 3-season porch

OPEN TODAY, 5PM TO 6:30PM

ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Breathtaking luxury condo just moments from Winchester Center and the commuter rail. This recently updated home offers bright, spacious, one-level living with hardwood floors and custom shutters throughout. The kitchen features quartz countertops, stainless steel appliances–including GE Café range and microwave, an oversized sink, and large peninsula with ample seating flows seamlessly to the adjoining living room with gas fireplace. The nearby pantry offers plenty of storage with stacked laundry adding exceptional convenience. A versatile dining room with large windows provides additional space for flexible use. The primary suite, which includes a walk-in closet and private ba

$999,999

3 beds2 baths1,535 sq ft

16 Park Ave #1, Winchester, MA 01890

Quartz countertops • Oversized sink • Custom shutters

OPEN SUN, 12PM TO 1:30PM3D WALKTHROUGH

ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Here's a rare opportunity to own a spectacular new construction home by a premier local builder on a BRAND-NEW road. This property stands prominently on its lot, overlooking a lush wooded area with close proximity to “The Fells”. The first floor is designed for both entertaining and everyday living, featuring formal dining, a designer kitchen with a butler's pantry, and a fireplaced family room that exudes warmth and comfort. Each of the bedrooms are found on the second floor, including a versatile space that could seamlessly integrate into the primary. The primary bath is a sanctuary of luxury, accompanied by an opulent dressing room. The lower level offers a walk-out rec room

$2,999,999

5 beds4.5 baths5,716 sq ft

6 Abby Rd, Winchester, MA 01890

Walk-out rec room • New construction • Dedicated home gym

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 ameniti

$995,000

4 beds3 baths1,860 sq ft

60 Harvard, Winchester, MA 01890

Off street parking • Multi-family • Local area amenities

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 10 Mason Way, Woburn, MA 01801, 3 beds, 2.5 baths

$1,274,999

3 beds2.5 baths2,300 sq ft

10 Mason Way, Woburn, MA 01801

Listing provided by Zillow

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 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

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OPEN FRI, 4PM TO 5:30PM

ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
NEW TO MARKET! Loads of curb appeal to this wonderful home on a gorgeous corner lot with wrap around farmers porch, fenced in yard, and oversized garage. A+ location in a desirable residential neighborhood, easily accessible to the highway & Stoneham Square. This home has so much to offer. A large and open first floor boasts an oversized living room w/ fireplace, formal dining room, and spacious kitchen with a separate dining area. There is also a half bath, laundry room, and grand entryway. Upstairs you will find four bedrooms and two full baths. The oversized primary bedroom w/ ensuite bath is separated from the other three bedrooms. The three secondary bedrooms are well proportione

$795,000

4 beds2.5 baths2,252 sq ft

7 Everett St, Stoneham, MA 02180

7,802 sq ft lot • Garage • Somewhat walkable

ABOUT THIS HOME
Winchester Highlands, 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

$555 HOA • Garage • Community pool

ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Welcome to your next chapter in this beautifully maintained multi-level home blending comfort, style, and convenience. Step into the sun-filled kitchen and dining area, where vaulted ceilings, skylights, cherry cabinetry, granite counters, and a large island create a warm gathering space. From here, open the slider to a sprawling two-tier deck, perfect for entertaining or relaxing outdoors. The dining room overlooks a spacious living room with a traditional brick fireplace, built-in speakers, and an additional seating nook for cozy evenings. The main level also features a private primary suite with a full bath, wet bar, and direct deck access, creating your own retreat. Upstairs, you’

$950,000

4 beds2.5 baths2,204 sq ft

27 Blueberry Hill Rd, Woburn, MA 01801

0.25 acre lot • 2 garage spots • Car-dependent

3D WALKTHROUGH

ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
This 2024 construction offers single-level living with 2 bedrooms + flex room. The open-concept layout creates an airy, contemporary atmosphere. The bonus flex room/den adapts effortlessly to your needs. The stylish white kitchen showcases shaker cabinets with ample storage & a center island and flows seamlessly into the dining/living areas for dinner conversations. Enjoy your private outdoor space in your enclosed patio accessible off of the living room. The primary suite impresses with a huge walk in custom closet & a luxurious en-suite bath with double vanity. The second bed is spacious and bright. The one-car garage also has additional storage space, while elevator access &

$799,900

2 beds2 baths1,424 sq ft

2 Stratton Dr #102, Woburn, MA 01801

$484 HOA • Garage • Car-dependent

ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
On the Winchester line! This custom-built 2014 home offers nine-foot ceilings and an open, spacious layout. A grand entryway leads to a formal dining room and an oversized chef’s kitchen with granite island, repurposed oak table extension, prep sink, high-end appliances, wine refrigerator, and pantry. The kitchen flows seamlessly into a fireplaced family room with built-in media storage and a sun-filled three-season room. The first-floor primary suite includes a walk-in closet or office and ensuite bath, while a second primary suite features a spa bath with sauna and direct access to a private deck. An additional ensuite bedroom plus two more generous bedrooms provide comfort for all.

$1,575,000

5 beds4 baths4,578 sq ft

9 Washington Ave, Woburn, MA 01801

0.36 acre lot • 2 garage spots • Car-dependent

OPEN SUN, 10:30AM TO 12PM

ABOUT THIS HOME
Winchester Highlands, MA Homes for Sale
Presenting a charming 3- Bedrooms , 2 - Baths home at The Residences at Winchester featuring gleaming hardwood floors, freshly painted interior and updated lower level with brand new flooring. This move-in-ready has comfort , and functionality across all levels. The first floor includes bright Living room , a dedicated dining room and an updated kitchen with granite countertops and stainless steel appliances. The second floor offers three comfortable bedrooms and a full bath. The lower level provides added flexibility with a generous family room and a second full bath-family room , play room or office. Extra storage space in attic. Close to everything, commuter rail to Boston and access to

$662,500

3 beds2 baths1,232 sq ft

2 George Rd #2, Winchester, MA 01890

$235 HOA • Somewhat walkable

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 6 Mason Way, Woburn, MA 01801, 3 beds, 2.5 baths

$1,249,995

3 beds2.5 baths2,143 sq ft

6 Mason Way, Woburn, MA 01801

Listing provided by Zillow

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 6 Mason Way #63, Woburn, MA 01801, 3 beds, 2.5 baths

$1,304,855

3 beds2.5 baths2,143 sq ft

6 Mason Way #63, Woburn, MA 01801

Property at 2 Mason Way #65, Woburn, MA 01801, 3 beds, 3.5 baths

$1,405,475

3 beds3.5 baths2,909 sq ft

2 Mason Way #65, Woburn, MA 01801

Property at 2 Mason Way, Woburn, MA 01801, 3 beds, 3.5 baths

$1,324,999

3 beds3.5 baths2,909 sq ft

2 Mason Way, Woburn, MA 01801

Listing provided by Zillow

Property at 6 Stratton Dr #3208, Woburn, MA 01801, 1 bed, 1 bath

$699,995

1 bed1 bath1,129 sq ft

6 Stratton Dr #3208, Woburn, MA 01801

Property at Belmont Plan, Vx9nc Woburn, MA 01801, 2 beds, 2 baths

$1,099,995

2 beds2 baths1,796 sq ft

Belmont Plan, Vx9nc Woburn, MA 01801

Listing provided by Zillow

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

$999,999

2 beds2 baths1,796 sq ft

2 Stratton Dr #109, Woburn, MA 01801

Listing provided by Zillow

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 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

$1,274,999

3 beds2.5 baths2,300 sq ft

Southbrook Plan, Woburn, MA 01801

Listing provided by Zillow

Average home prices near Winchester Highlands, MA

Cities

Neighborhoods

Winchester Town Center homes for sale
$1,745,000
Greenwood homes for sale
$995,000
Wyoming homes for sale
$499,900
West Medford homes for sale
$1,120,000
Morningside homes for sale
$1,349,999
Wedgemere homes for sale
$2,239,000
Montvale homes for sale
$1,187,450
Woburn Highlands homes for sale
$768,750
Downtown Melrose homes for sale
$749,900
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)

$1,197,250

+1.4% 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 Highlands, MA

$1,197,250

+1.4%

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