Winchester, MA homes for sale & real estate

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20 Grayson Rd, Winchester, MA 01890
20 Grayson Rd, Winchester, MA 01890
20 Grayson Rd, Winchester, MA 01890
ABOUT THIS HOME
Winchester, 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

Custom cabinetry • Designer kitchen • Luxury finishes

OPEN SAT, 1PM TO 2:30PM

70 Woodside Rd, Winchester, MA 01890
70 Woodside Rd, Winchester, MA 01890
70 Woodside Rd, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
Have you ever dreamed of owning a house with a white picket fence? Here it is! Eight rooms, four bedrooms, 2.5 baths. Corner lot with backyard patio, shed and one car garage. The large living room with many windows and a fireplace opens to the dining room. French doors from the dining room lead to a room that can be used as a family room, play room for the kids, or another bedroom. The pine-paneled, eat-in kitchen is modest yet efficient. The kitchen flows to back entrance, where a half bath is located. Central air conditioning on the second floor and heated floors in the full baths offer comfort in all seasons. The white picket fence and a perennial garden of hosta and day lilies border th

$1,199,000

4 beds2.5 baths2,566 sq ft

70 Woodside Rd, Winchester, MA 01890

Perennial garden • Backyard patio • Heated floors

OPEN FRI, 5PM TO 7PM

5 Cutting St, Winchester, MA 01890
5 Cutting St, Winchester, MA 01890
5 Cutting St, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
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 shelves. The 2nd level offers 3 bedroo

$1,075,000

3 beds1.5 baths1,414 sq ft

5 Cutting St, Winchester, MA 01890

Tall ceilings • In-town location • Plantation shutters

OPEN SAT, 12PM TO 2PMHOT HOME

162 Forest St, Winchester, MA 01890
162 Forest St, Winchester, MA 01890
162 Forest St, Winchester, MA 01890
ABOUT THIS HOME
Winchester, 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

New gas range • Natural woodwork • 2019 updated kitchen

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26 Swan Rd, Winchester, MA 01890
26 Swan Rd, Winchester, MA 01890
26 Swan Rd, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with 2 primary suite options! This magnificent residence boasts expansive living spaces, elevator & indoor pool! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/ custom cherry cabinetry & high end appliances leading to adj. family room w/ fireplace. A handsome library w/ fireplace offers a warm and inviting space to relax. The highlight of this extraordinary home is the 16x32 indoor freshwater pool & jacuzzi set within a breathtaking atrium room w/ soaring vaulted ceilings,

$3,599,000

6 beds6.5 baths8,463 sq ft

26 Swan Rd, Winchester, MA 01890

Handsome library • Atrium room • Gourmet kitchen

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

$1,725,000

4 beds3.5 baths2,755 sq ft

5 Thornton 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

$1,225,000

4 beds3 baths1,860 sq ft

60 Harvard, Winchester, MA 01890

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

$1,899,000

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 20 Arthur St #20, Winchester, MA 01890, 2 beds, 1 bath

$625,900

2 beds1 bath1,084 sq ft

20 Arthur St #20, Winchester, MA 01890

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

$1,980,000

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

$2,195,000

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, 6 beds, 3.5 baths

$3,895,000

6 beds3.5 baths4,484 sq ft

9 Lakeview Ter, Winchester, MA 01890

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

$2,499,000

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 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 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

$2,975,000

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

$1,399,900

5 beds2 baths3,033 sq ft

7 Thornberry Rd, 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, 5 beds, 3.5 baths

$2,299,000

5 beds3.5 baths6,232 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 20 Amberwood Dr, Winchester, MA 01890, 6 beds, 7 baths

$3,598,000

6 beds7 baths8,866 sq ft

20 Amberwood Dr, 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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Average home prices near Winchester, MA

Cities

Neighborhoods
Zip Codes

West Side homes for sale
$2,349,900
Arlington Heights homes for sale
$1,499,900
West Medford homes for sale
$1,090,000
Wedgemere homes for sale
$2,419,000
Morningside homes for sale
$1,695,000
Montvale homes for sale
Countryside homes for sale
$3,925,000
Winchester Highlands homes for sale
$1,299,995
Woburn Highlands homes for sale
$699,900
Downtown Woburn homes for sale
$689,450

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)

$1,500,000

+1.4% 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, MA

$1,500,000

+1.4%

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