Winchester, MA homes for sale & real estate

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ABOUT THIS HOME
Winchester, MA Homes for Sale
Beautifully updated & impeccably maintained 3 BR, 3.5 bath home on a sought-after cul-de-sac w/ lovely front & side yards, abutting conservation land for exceptional privacy. The main level features a spacious living room, updated sunroom, granite kitchen w/ newer SS appliances, abundant cabinetry, peninsula seating, & dining room w/ access to an inviting deck. Two 1st floor bedrooms & two full baths, including an en-suite, offer exceptional flexibility. The 2nd floor primary suite is a private retreat w/ a vaulted ceiling, oversized walk-in closet, spacious bath w/ double vanity. This level offers an additional storage closet & unfinished room w/ expansion pote

$1,699,000

3 beds3.5 baths2,513 sq ft

2 Olde Lyme Rd, Winchester, MA 01890

Updated sunroom • Inviting deck • Abundant cabinetry

EARLY ACCESSCOMPASS COMING SOON

Unknown

4 beds2.5 baths5,925 sq ft

187 High St, Winchester, MA 01890

Built 1988

OPEN TODAY, 5PM TO 6PM

ABOUT THIS HOME
Winchester, MA Homes for Sale
Completely renovated in 2021, this stunning 3-bedroom, 2.5-bath townhouse offers the comfort and feel of a single-family home with three levels of beautifully finished living space. The open and inviting floor plan features hardwood floors throughout, modern finishes, and abundant natural light. The spacious third-floor primary suite provides a private retreat with spacious walk in closet and its own full bath. Second floor features 2 ample sized bedrooms, full bath and laundry. Step outside through the sliding glass doors to a newly installed stone patio and backyard—perfect for relaxing, entertaining, or outdoor dining. Additional highlights include two off-street parking spaces and

$1,150,000

3 beds2.5 baths2,004 sq ft

52 Salem St #52, Winchester, MA 01890

Thoughtful updates • 2 parking spots • Built 1880

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Winchester, MA Homes for Sale
Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds convenience and additional storage, and a half bath is located in the unfinished basement. Just 1 mile from Winchester Center, enjoy easy access to restaurants, coffee shops, boutiques, the public library, and commuter options with close proximity to Boston. The recently built elementary school and renov

$950,000

3 beds1 bath1,356 sq ft

47 Water St, Winchester, MA 01890

Waterfront views • Unfinished basement • Detached garage

OPEN FRI, 5PM TO 6PM

ABOUT THIS HOME
Winchester, MA Homes for Sale
Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for everyday living and entertaining. The second floor includes a full bath, a bedroom, and a versatile bonus room ideal for a home office, playroom, or guest space. The private third-floor primary suite features skylights, a custom-designed bath with a built-in makeup vanity, and generous storage. The f

$729,000

3 beds2.5 baths1,494 sq ft

247 Washington St #11, Winchester, MA 01890

Renovated kitchen • Granite countertops • Skylights

Property at 10 Dartmouth St, Winchester, MA 01890, 5 beds, 3 baths

$2,999,000

5 beds3 baths4,028 sq ft

10 Dartmouth St, Winchester, MA 01890

Property at 200 Swanton Unit L8, Winchester, MA 01890, 1 bath

$288,750

0 beds1 bath388 sq ft

200 Swanton Unit L8, Winchester, MA 01890

Property at 79 Grove St, Winchester, MA 01890, 5 beds, 3.5 baths

$1,899,000

5 beds3.5 baths3,210 sq ft

79 Grove St, Winchester, MA 01890

Property at 241 Ridge St, Winchester, MA 01890, 4 beds, 3 baths

$1,599,000

4 beds3 baths2,480 sq ft

241 Ridge St, Winchester, MA 01890

Property at 258 Cross St, Winchester, MA 01890, 4 beds, 2 baths

$999,900

4 beds2 baths1,719 sq ft

258 Cross St, Winchester, MA 01890

Property at 46 Clark St, Winchester, MA 01890, 4 beds, 1.5 baths

$1,099,000

4 beds1.5 baths1,777 sq ft

46 Clark St, Winchester, MA 01890

Property at 84 Oak St, Winchester, MA 01890, 4 beds, 2 baths

$900,000

4 beds2 baths2,083 sq ft

84 Oak St, Winchester, MA 01890

Property at 14 Hillside Ave, Winchester, MA 01890, 4 beds, 4.5 baths

$2,380,000

4 beds4.5 baths3,881 sq ft

14 Hillside Ave, Winchester, MA 01890

Property at 423 Washington St, Winchester, MA 01890, 4 beds, 3 baths

$1,350,000

4 beds3 baths2,690 sq ft

423 Washington St, Winchester, MA 01890

Property at 9 Plymouth Rd, Winchester, MA 01890, 5 beds, 3 baths

$2,500,000

5 beds3 baths4,071 sq ft

9 Plymouth Rd, Winchester, MA 01890

Property at 26 N Gateway, Winchester, MA 01890, 4 beds, 3.5 baths

$2,149,000

4 beds3.5 baths3,210 sq ft

26 N Gateway, Winchester, MA 01890

Property at 38 Robinhood Rd, Winchester, MA 01890, 3 beds, 2 baths

$1,175,000

3 beds2 baths1,736 sq ft

38 Robinhood Rd, Winchester, MA 01890

Property at 15 Fieldstone Dr, Winchester, MA 01890, 4 beds, 3.5 baths

$1,975,000

4 beds3.5 baths3,286 sq ft

15 Fieldstone Dr, Winchester, MA 01890

Property at 150 Cambridge St, Winchester, MA 01890, 3 beds, 1.5 baths

$1,099,000

3 beds1.5 baths1,711 sq ft

150 Cambridge St, Winchester, MA 01890

Property at 50 Middlesex St #50, Winchester, MA 01890, 2 beds, 2 baths

$799,000

2 beds2 baths1,036 sq ft

50 Middlesex St #50, Winchester, MA 01890

Property at 53 Winford Way, Winchester, MA 01890, 5 beds, 4 baths

$2,399,000

5 beds4 baths5,083 sq ft

53 Winford Way, Winchester, MA 01890

Property at 117 Highland Ave, Winchester, MA 01890, 5 beds, 3.5 baths

$1,725,000

5 beds3.5 baths3,722 sq ft

117 Highland Ave, Winchester, MA 01890

Property at 666 Main St #315, Winchester, MA 01890, 2 beds, 2 baths

$649,900

2 beds2 baths1,025 sq ft

666 Main St #315, Winchester, MA 01890

Property at 53 Lake St, Winchester, MA 01890, 3 beds, 2.5 baths

$1,199,000

3 beds2.5 baths2,235 sq ft

53 Lake St, Winchester, MA 01890

Property at 23 Shepard Ct Unit U23, Winchester, MA 01890, 3 beds, 3 baths

$699,000

3 beds3 baths1,380 sq ft

23 Shepard Ct Unit U23, Winchester, MA 01890

Property at 8 Hawthorne Rd, Winchester, MA 01890, 5 beds, 3 baths

$1,825,000

5 beds3 baths3,315 sq ft

8 Hawthorne Rd, Winchester, MA 01890

Property at 10 Rangeley Rd, Winchester, MA 01890, 5 beds, 4.5 baths

$3,199,000

5 beds4.5 baths5,406 sq ft

10 Rangeley Rd, Winchester, MA 01890

Property at 78 Bacon St, Winchester, MA 01890, 5 beds, 3.5 baths

$2,499,000

5 beds3.5 baths5,230 sq ft

78 Bacon St, Winchester, MA 01890

Property at 9 Brookside Pl, Winchester, MA 01890, 4 beds, 2.5 baths

$1,899,000

4 beds2.5 baths3,091 sq ft

9 Brookside Pl, Winchester, MA 01890

Property at 7 Wainwright Rd #47, Winchester, MA 01890, 3 beds, 3 baths

$1,299,000

3 beds3 baths2,145 sq ft

7 Wainwright Rd #47, Winchester, MA 01890

Property at 129 Washington St #129, Winchester, MA 01890, 3 beds, 3.5 baths

$1,099,000

3 beds3.5 baths2,420 sq ft

129 Washington St #129, Winchester, MA 01890

Property at 18 Middlesex St, Winchester, MA 01890, 4 beds, 4.5 baths

$2,795,000

4 beds4.5 baths5,233 sq ft

18 Middlesex St, Winchester, MA 01890

Property at 200 Swanton St #303, Winchester, MA 01890, 2 beds, 1 bath

$499,999

2 beds1 bath822 sq ft

200 Swanton St #303, Winchester, MA 01890

Property at 8 Priscilla Ln, Winchester, MA 01890, 5 beds, 5.5 baths

$3,149,000

5 beds5.5 baths6,500 sq ft

8 Priscilla Ln, Winchester, MA 01890

Property at 63-65 Harvard St, Winchester, MA 01890, 5 beds, 3 baths

$1,150,000

5 beds3 baths2,186 sq ft

63-65 Harvard St, Winchester, MA 01890

Property at 2 Atherton Rd, Winchester, MA 01890, 6 beds, 6.5 baths

$3,350,000

6 beds6.5 baths7,400 sq ft

2 Atherton Rd, Winchester, MA 01890

Property at 16 & 16A Glenwood Ave, Winchester, MA 01890, 6 beds, 4.5 baths

$1,899,000

6 beds4.5 baths6,900 sq ft

16 & 16A Glenwood Ave, Winchester, MA 01890

Property at 83 Church St #15, Winchester, MA 01890, 2 beds, 1.5 baths

$999,000

2 beds1.5 baths1,365 sq ft

83 Church St #15, Winchester, MA 01890

Property at 16 Glenwood Ave, Winchester, MA 01890, 6 beds, 4.5 baths

$1,899,000

6 beds4.5 baths6,900 sq ft

16 Glenwood Ave, Winchester, MA 01890

Property at 18 Ridge St, Winchester, MA 01890, 5 beds, 5.5 baths

$3,450,000

5 beds5.5 baths5,295 sq ft

18 Ridge St, Winchester, MA 01890

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

$929,900

4 beds2 baths1,938 sq ft

380 Cross St, Winchester, MA 01890

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Average home prices near Winchester, MA

Cities

Neighborhoods
Zip Codes

North Main homes for sale
$1,247,500
Winchester Town Center homes for sale
$1,049,450
Arlington Heights homes for sale
$1,250,000
West Medford homes for sale
$1,047,000
Arlington Center homes for sale
$1,398,000
Shakerhill homes for sale
$749,900
Winchester Highlands homes for sale
$1,537,500
Woburn Highlands homes for sale
$774,950
Downtown Woburn homes for sale
$724,900
The Flats homes for sale
$2,764,000

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)

$1,386,670

-26.3% YoY | May 2026

1 year
3 year
5 year

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

Location

Data

May 2026

Growth

% YoY

Winchester, MA

$1,386,670

-26.3%

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12 Redfin agents serving Winchester

276

Deals*

4.8

Satisfaction

2950

Homes closed*

* Data from the last year

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