West Side, MA homes for sale & real estate

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NEW 12 HRS AGO

7 Wainwright Rd #72, Winchester, MA 01890
7 Wainwright Rd #72, Winchester, MA 01890
7 Wainwright Rd #72, Winchester, MA 01890
ABOUT THIS HOME
West Side, MA Homes for Sale
Extensively renovated and move-in ready, this stunning F-unit townhouse offers 4 bedrooms and 4.5 baths with impeccable detail and modern appeal throughout. The many windows, high ceilings, gleaming hardwood floors, and open design create a warm sun-filled home. You will enjoy the large kitchen and the ability to retreat to the dazzling first-floor primary suite, which provides single floor living in a separate bedroom wing. The living areas feature a dramatic two-sided gas fireplace with floor-to-ceiling stone tile. Enjoy outdoor living on the two expansive decks. The finished walkout lower level includes a sitting room, additional bedroom, and full bath—

$1,950,000

4 beds4.5 baths3,512 sq ft

7 Wainwright Rd #72, Winchester, MA 01890

Move-in ready • Two expansive decks • Large kitchen

257 High St, Winchester, MA 01890
257 High St, Winchester, MA 01890
257 High St, Winchester, MA 01890
ABOUT THIS HOME
West Side, MA Homes for Sale
Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck, mudroom, pantry & oversized 2 car garage. The 2nd floor offers a stunning master w sitting area, marble bath & walk in closet. 3 add'l BR's, all generously sized. The expansive lower level features an inviting screened "Florida room" family space that opens to a bluestone patio w

$3,499,000

5 beds6 baths7,101 sq ft

257 High St, Winchester, MA 01890

Oversized lot • Glorious deck • 1.68 acre lot

20 Amberwood Dr, Winchester, MA 01890
20 Amberwood Dr, Winchester, MA 01890
20 Amberwood Dr, Winchester, MA 01890
ABOUT THIS HOME
West Side, MA Homes for Sale
Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador appliances, custom cabinetry, and a large island that flows seamlessly to an oversized deck—perfect for entertaining or relaxing. Upstairs, the 2nd floor offers spacious ensuite bedrooms, the luxurious primary suite with a walk-in closet and direct access to a private deck. Additional highlights

$3,600,000

6 beds7 baths8,866 sq ft

20 Amberwood Dr, Winchester, MA 01890

Elegant layout • Soaring ceilings • Chef's kitchen

5 Azalea Rd, Winchester, MA 01890
5 Azalea Rd, Winchester, MA 01890
5 Azalea Rd, Winchester, MA 01890
ABOUT THIS HOME
West Side, MA Homes for Sale
NEW PRICE! RENOVATIONS & UPDATES JUST COMPLETED THROUGHOUT! Pristine Home nestled in Winchester's Sought After West Side Neighborhood and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/ Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to New Composite Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials and Mature Trees to Relax and Enjoy! Elegant Dining Room open to Grand Entry Foyer and Gorgeous Sunken Living Room w/ Beautiful Fireplace. Primary Suite w/ Sitting Area & Luxurious Spa-Like Ensuite Bath. Oversized Great Room w/ Stone Fireplace, 5th Bedroom/Office w/ Separate Entrance,

$2,199,000

5 beds3.5 baths6,232 sq ft

5 Azalea Rd, Winchester, MA 01890

Cul de sac • New composite deck • Stone patio

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7 Thornberry Rd, Winchester, MA 01890
7 Thornberry Rd, Winchester, MA 01890
7 Thornberry Rd, Winchester, MA 01890
ABOUT THIS HOME
West Side, MA Homes for Sale
Priced to SELL this newly renovated contemporary home, nestled in a highly sought-after West-side neighborhood with surprising space! This 3+ level home boasts 4-5 spacious bedrooms and 2 full stylish baths, this home offers versatile space for multiple home offices, in law/ au-pair space plus comfortable family spaces all great for entertaining. The main level features a beautiful open-concept kitchen w/ high end appliances & quartz counters w/ island seating, adjacent dining w/ soaring ceilings, step down the living room w/ fplc & walls of glass overlooking large lot w/ patio & fire pit. 4 spacious BR's plus finished LL perfect family/playroom, plus BR #5 or office. Enjo

$1,379,000

5 beds2 baths3,033 sq ft

7 Thornberry Rd, Winchester, MA 01890

Quartz counters • Island seating • Open-concept kitchen

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

$1,900,000

4 beds4 baths5,361 sq ft

4 Aricia Ln, 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 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 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

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Nearby homes that match your criteria

NEW 3 HRS AGO

281 Forest St, Arlington, MA 02474
281 Forest St, Arlington, MA 02474
281 Forest St, Arlington, MA 02474
ABOUT THIS HOME
West Side, MA Homes for Sale
Welcome to this stunning, fully renovated single-family home in the highly sought-after Turkey Hill neighborhood. This home was meticulously gut-renovated in 2025 and seamlessly blends modern luxury with classic charm. The main floor features an open-concept layout with gourmet kitchen and wine cellar, perfect for entertaining, along with a convenient in-law or guest suite. Upstairs, the primary bedroom suite offers a private retreat, accompanied by two additional, generously sized bedrooms. Exquisite millwork and hardwood floors extend throughout the home, highlighting the high-quality craftsmanship. The residence is equipped with central air conditioning and an EV charger in the garage fo

$1,815,000

4 beds4 baths3,088 sq ft

281 Forest St, Arlington, MA 02474

4,870 sq ft lot • Garage • Car-dependent

7 Anna Rd, Woburn, MA 01801
7 Anna Rd, Woburn, MA 01801
7 Anna Rd, Woburn, MA 01801
ABOUT THIS HOME
West Side, MA Homes for Sale
Set on the desirable West Side near the Lexington line, this 3 bedroom, 3 full bath home offers over 1,700 sq. ft. of living space with multiple living areas, central A/C, and a fully fenced quarter-acre yard. Thoughtfully upgraded for today’s lifestyle, this home has too many updates to name. Highlights include updated kitchen counters, cabinets, and tile (2021), a newly finished lower level adding flexible living space (2025), and a brand-new patio (2025). A deck off the kitchen makes grilling and hosting easy — perfect for football Sundays. Two walk-out basements provide excellent potential for an ADU conversion or in-law setup. A rare mix of space, upgrades, and location tha

$759,000

3 beds3 baths1,764 sq ft

7 Anna Rd, Woburn, MA 01801

0.24 acre lot • Car-dependent

8 Winning Farm Rd #8, Woburn, MA 01801
8 Winning Farm Rd #8, Woburn, MA 01801
8 Winning Farm Rd #8, Woburn, MA 01801
ABOUT THIS HOME
West Side, MA Homes for Sale
Welcome to The Villages at Winning Farm - Here is your chance to win an Option "C" in a perfect location with so many "At Build Upgrades". Open Concept first floor allows for great entertaining! Gourmet Kitchen with island, private dining area, and oversized living room with gas fireplace. Move right into outdoor enjoyment via a slider to private deck and picturesque scenery. Tucked away at the other end of the first floor is an home office with a french door, half bath, two huge closets, and both garage and basement access. Second Level invites you to a Primary Suite with fabulous walk in shower, double vanities, linen storage. Wait till you see the oversized walk in c

$1,075,000

3 beds2.5 baths2,079 sq ft

8 Winning Farm Rd #8, Woburn, MA 01801

$527 HOA • Garage • Community pool

269 Cambridge Rd #203, Woburn, MA 01801
269 Cambridge Rd #203, Woburn, MA 01801
269 Cambridge Rd #203, Woburn, MA 01801
ABOUT THIS HOME
West Side, MA Homes for Sale
Welcome to Crescent Park! This bright and inviting 1-bedroom, 1.5-bath condo offers comfort and convenience. The open living room features recessed lighting and direct access to a private balcony, perfect for relaxing outdoors. The modern kitchen is appointed with white shaker-style cabinetry, quartz countertops, and stainless steel appliances. A half bath is conveniently located off the hallway that includes a washer & dryer. The spacious bedroom provides ample closet space, while the recently renovated full bath boasts a sleek walk-in shower. This unit also includes one assigned parking spot. Enjoy resort-style amenities such as a swimming pool, fitness room, and clubroom. Ideally s

$399,900

1 bed1.5 baths660 sq ft

269 Cambridge Rd #203, Woburn, MA 01801

$447 HOA • Community pool • Somewhat walkable

273 Cambridge Rd #202, Woburn, MA 01801
273 Cambridge Rd #202, Woburn, MA 01801
273 Cambridge Rd #202, Woburn, MA 01801
ABOUT THIS HOME
West Side, MA Homes for Sale
Spacious 2-bedroom, 2-bath condo at Crescent Park offering 1,168 square feet of one-level living. This bright unit features an open-concept living and dining area with direct access to a private balcony. The kitchen includes ample cabinetry and a separate pantry. The primary bedroom offers a walk-in closet and en-suite bathroom. While the unit could benefit from some cosmetic updates, it presents a great opportunity to add value and personalize to your taste. Enjoy close by elevator access, nearby trash room, in-unit laundry, additional storage, a designated parking space, clubhouse, fitness room, and in-ground pool. Conveniently located on the Winchester/Woburn line, across from Sogno and

$549,900

2 beds2 baths1,168 sq ft

273 Cambridge Rd #202, Woburn, MA 01801

$567 HOA • Community pool • Somewhat walkable

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48 Salisbury St, Winchester, MA 01890
48 Salisbury St, Winchester, MA 01890
48 Salisbury St, Winchester, MA 01890
ABOUT THIS HOME
West Side, MA Homes for Sale
Thoughtfully renovated & meticulously maintained, this classic colonial home in the Flats invites with timeless charm & modern conveniences. Through the center entrance be welcomed into the fireplaced living room & dining room- both refreshed in 2025 with new lighting, paint & wallpaper. The open-plan custom kitchen with marble counters, stainless appliances, and a butler’s pantry with sink, granite counters, and second dishwasher make this a wonderful home for entertaining. The second floor features a primary suite with walk-in closet & marble bath w/ soaking tub, 3 generous bedrooms with a full hall bath, and a laundry-ready closet. The lower level offe

$2,750,000

5 beds3.5 baths4,779 sq ft

48 Salisbury St, Winchester, MA 01890

0.24 acre lot • 2 garage spots • Car-dependent

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 8 Blueberry Ln, Lexington, MA 02420, 6 beds, 7.5 baths

$4,249,000

6 beds7.5 baths7,653 sq ft

8 Blueberry Ln, Lexington, MA 02420

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 18 Blueberry Ln, Lexington, MA 02420, 6 beds, 6.5 baths

$4,200,000

6 beds6.5 baths7,705 sq ft

18 Blueberry Ln, Lexington, MA 02420

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 2 Pheasant Ln, Woburn, MA 01801, 3 beds, 2.5 baths

$1,298,000

3 beds2.5 baths1,850 sq ft

2 Pheasant Ln, Woburn, MA 01801

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 66 Windmill Ln, Arlington, MA 02474, 3 beds, 2 baths

$1,200,000

3 beds2 baths3,036 sq ft

66 Windmill Ln, Arlington, MA 02474

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

$3,099,000

6 beds6.5 baths6,028 sq ft

44 Cabot St, Winchester, MA 01890

Average home prices near West Side, MA

Cities

Neighborhoods

Arlington Heights homes for sale
$1,460,000
West Medford homes for sale
$1,120,000
East Arlington homes for sale
$1,189,500
Wedgemere homes for sale
$2,239,000
North Waltham homes for sale
$949,900
Belmont Hill homes for sale
$2,810,000
Montvale homes for sale
$1,187,450
North Lexington homes for sale
$1,998,000
Woburn Highlands homes for sale
$708,250
Brattle homes for sale
$1,199,000

West Side, MA real estate trends

All Home Types trends in West Side, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,545,500

-17.2% YoY | Jul 2025

1 year
3 year
5 year

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

Location

Data

Jul 2025

Growth

% YoY

West Side, MA

$1,545,500

-17.2%

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