Winchester, MA homes for sale & real estate

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OPEN TODAY, 12PM TO 1:30PM

ABOUT THIS HOME
Winchester, MA Homes for Sale
Rare Opportunity: Spacious Side-by-Side Two-Family Home Less Than 1 Mile from Town Center. This charming two-family home offers classic period details, including fireplaced living rooms, formal dining rooms with built-in china cabinets located directly off the kitchen. Each unit features two large bedrooms with hardwood floors and a full bath on the second floor, plus two additional bedrooms and storage on the third floor. Both units have separate, spacious basements with tall ceilings and separate utilities. Great yard space, two-car garage and driveway located off Glen Rd. Located less than 3/4 mile from the town center, this property is ideal for both investors and owner-occupants. Don&r

$1,650,000

8 beds2.5 baths3,591 sq ft

112 Church St, Winchester, MA 01890

Two family home • Formal dining rooms • Hardwood floors

OPEN SUN, 11AM TO 12:30PM

ABOUT THIS HOME
Winchester, MA Homes for Sale
NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. Formal dining room & dramatic oversized family room will impress, featuring vaulted ceilings, gas fireplace and plenty of windows. The first floor also includes a bedroom suite w/ full bath! Upstairs you'll find 3 spacious bedrooms, including the primary suite w/ walk-in closet & beautiful en-suite bath w/ large shower, tub & double vanity sinks. Additional BR5

$2,399,000

5 beds4 baths4,334 sq ft

237 Swanton St, Winchester, MA 01890

Custom cabinetry • Eat in kitchen • Stainless appliances

ABOUT THIS HOME
Winchester, MA Homes for Sale
The buyer got cold feet. 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

$1,649,000

5 beds4 baths3,508 sq ft

166 Forest St, Winchester, MA 01890

Private deck • Hot tub • Gourmet kitchen

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ABOUT THIS HOME
Winchester, MA Homes for Sale
Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end eat-in kitchen with large island & granite countertops as well as a formal dining room with gas fireplace. A living room with custom built-ins & window seat, a family room overlooking the yard, and a bar complete this level. This distinguished residence offers 7 bedrooms and 6 bathrooms

$4,174,000

7 beds4.5 baths7,043 sq ft

2 Everett Ave, Winchester, MA 01890

Formal dining room • Primary suite • Custom built-ins

ABOUT THIS HOME
Winchester, 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

Tennis court • Picturesque grounds • Swimming pool

Property at 571 Washington St, Winchester, MA 01890, 3 beds, 1 bath

$959,000

3 beds1 bath1,425 sq ft

571 Washington St, Winchester, MA 01890

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

$3,899,000

6 beds4.5 baths6,367 sq ft

40 Foxcroft Rd, Winchester, MA 01890

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

$2,199,000

5 beds3.5 baths6,232 sq ft

5 Azalea Rd, Winchester, MA 01890

Property at 257 High St, Winchester, MA 01890, 5 beds, 6 baths

$3,499,000

5 beds6 baths7,101 sq ft

257 High St, Winchester, MA 01890

Property at 4 Wyman Ct #4, Winchester, MA 01890, 4 beds, 4.5 baths

$1,399,000

4 beds4.5 baths2,500 sq ft

4 Wyman Ct #4, Winchester, MA 01890

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

$2,399,000

6 beds4.5 baths4,200 sq ft

14 Grant Rd, Winchester, MA 01890

Property at 16 Park Ave #1, Winchester, MA 01890, 3 beds, 2 baths

$999,999

3 beds2 baths1,535 sq ft

16 Park Ave #1, Winchester, MA 01890

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

$399,900

2 beds1 bath1,084 sq ft

20 Arthur St #20, Winchester, MA 01890

Property at 380 Cross St, Winchester, MA 01890, 4 beds, 2 baths

$1,050,000

4 beds2 baths1,938 sq ft

380 Cross St, Winchester, MA 01890

Property at 2 George Rd #2, Winchester, MA 01890, 3 beds, 2 baths

$662,500

3 beds2 baths1,232 sq ft

2 George Rd #2, Winchester, MA 01890

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

$3,600,000

6 beds7 baths8,866 sq ft

20 Amberwood Dr, Winchester, MA 01890

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 48 Salisbury St, Winchester, MA 01890, 5 beds, 3.5 baths

$2,695,000

5 beds3.5 baths4,779 sq ft

48 Salisbury St, Winchester, MA 01890

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

$1,879,000

5 beds3.5 baths3,294 sq ft

20 Grove Pl, Winchester, MA 01890

Property at 6 Abby Rd, Winchester, MA 01890, 5 beds, 4.5 baths

$2,999,999

5 beds4.5 baths5,716 sq ft

6 Abby Rd, Winchester, MA 01890

Property at 200 Swanton St Unit T11, Winchester, MA 01890, 1 bed, 1 bath

$409,900

1 bed1 bath634 sq ft

200 Swanton St Unit T11, Winchester, MA 01890

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

$1,379,000

5 beds2 baths3,033 sq ft

7 Thornberry Rd, Winchester, MA 01890

Property at 19 Glengarry Rd, Winchester, MA 01890, 6 beds, 3.5 baths

$2,099,000

6 beds3.5 baths3,521 sq ft

19 Glengarry Rd, Winchester, MA 01890

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 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 382 S Border Rd, Winchester, MA 01890, 6 beds, 5.5 baths

$2,689,000

6 beds5.5 baths4,563 sq ft

382 S Border Rd, Winchester, MA 01890

Property at 7 Sherman Pl #7, Winchester, MA 01890, 4 beds, 2.5 baths

$1,450,000

4 beds2.5 baths2,765 sq ft

7 Sherman Pl #7, Winchester, MA 01890

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

$1,729,000

4 beds4 baths5,361 sq ft

4 Aricia Ln, 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 5 Bacon St, Winchester, MA 01890, 6 beds, 4 baths

$2,245,000

6 beds4 baths4,385 sq ft

5 Bacon St, Winchester, MA 01890

Property at 60 Harvard, Winchester, MA 01890, 4 beds, 3 baths

$995,000

4 beds3 baths1,860 sq ft

60 Harvard, Winchester, MA 01890

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 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 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 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

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

$2,799,000

7 beds5.5 baths5,864 sq ft

10 Sheffield Rd, 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 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

Winchester Town Center homes for sale
$1,990,000
West Side homes for sale
$2,039,500
Arlington Heights homes for sale
$1,460,000
West Medford homes for sale
$1,090,000
Arlington Center homes for sale
$1,285,000
Morningside homes for sale
$1,422,950
Wedgemere homes for sale
$2,242,000
Woburn Highlands homes for sale
$662,500
Winchester Highlands homes for sale
$1,499,450
Downtown Woburn homes for sale
$649,999

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)

$1,220,000

-7.3% 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, MA

$1,220,000

-7.3%

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