Winchester
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Winchester

Average List Price

$2,268,022

Average Price per Sqft

$552

Number of Active Listings

69

New Listings (last 30 days)

69

Average Days on the Market

39

Average Year Build

1951

Recent Transactions

Homes Sold (last 30 days)
12
Average Sale Price (last 30 days)
$2,076,125

Rental Market

Average Rent per month

$5,590

Known for its top-ranked schools and picturesque New England charm, Winchester is one of the most sought-after suburbs in Greater Boston. The town features stunning Victorian and Colonial homes, as well as newly built luxury properties. With tranquil lakes, vibrant downtown shops, and easy access to Boston via the commuter rail, Winchester is perfect for families and professionals looking for a peaceful yet convenient lifestyle.

Map of the area

Creating your map with the top listings, almost there...

$4,799,000
Winchester
19 Rangeley Rd, Winchester, MA, 01890
5 Beds
7 Baths
7,779 Sq ft
$4,799,000
MLS# 73341968
PENDING
$4,200,000
Winchester
3 Foxcroft Road, Winchester, MA, 01890
6 Beds
6 Baths
5,208 Sq ft
$4,200,000
MLS# 73334088
PENDING
3D Tour
$3,989,000
Winchester
Virtual Tour
OPEN 04/19/25 11:00AM - 12:00PM
26 Swan Road, Winchester, MA, 01890
6 Beds
7 Baths
8,463 Sq ft
$3,989,000
MLS# 73344473
ACTIVE
$3,599,000
Winchester
2 Chestnut St, Winchester, MA, 01890
6 Beds
5 Baths
5,500 Sq ft
$3,599,000
MLS# 73333668
CONTRACT
$3,599,000
Winchester
27 Everett Ave, Winchester, MA, 01890
6 Beds
6 Baths
7,431 Sq ft
$3,599,000
MLS# 73356139
ACTIVE
$3,499,000
Winchester
4 Norwood St, Winchester, MA, 01890
5 Beds
5 Baths
5,250 Sq ft
$3,499,000
MLS# 73333712
ACTIVE
$3,450,000
Winchester
58 Wedgemere Ave, Winchester, MA, 01890
5 Beds
5 Baths
4,800 Sq ft
$3,450,000
MLS# 73334029
PENDING
3D Tour
$3,350,000
Winchester
Virtual Tour
21 Sheffield West, Winchester, MA, 01890
6 Beds
5 Baths
5,198 Sq ft
$3,350,000
MLS# 73350559
ACTIVE
$3,199,000
Winchester
12 Prospect St, Winchester, MA, 01890
7 Beds
5 Baths
6,694 Sq ft
$3,199,000
MLS# 73340671
PENDING
3D Tour
$3,199,000
Winchester
Virtual Tour
51 Wedgemere Avenue, Winchester, MA, 01890
5 Beds
5 Baths
4,279 Sq ft
$3,199,000
MLS# 73346386
PENDING
3D Tour
$3,149,000
Winchester
Virtual Tour
10 Sheffield Road, Winchester, MA, 01890
7 Beds
6 Baths
6,200 Sq ft
$3,149,000
MLS# 73349102
ACTIVE
3D Tour
$2,999,000
Winchester
Virtual Tour
OPEN 04/19/25 1:00 - 2:30PM
8 Chestnut St, Winchester, MA, 01890
5 Beds
6 Baths
5,354 Sq ft
$2,999,000
MLS# 73342518
ACTIVE
3D Tour
$2,900,000
Winchester
Virtual Tour
45 Brooks Street, Winchester, MA, 01890
4 Beds
4 Baths
4,325 Sq ft
$2,900,000
MLS# 73352827
PENDING
$2,899,000
Winchester
5 Clearwater Rd, Winchester, MA, 01890
6 Beds
8 Baths
5,658 Sq ft
$2,899,000
MLS# 73334317
PENDING
$2,899,000
Winchester
11 Taft Dr, Winchester, MA, 01890
5 Beds
6 Baths
4,627 Sq ft
$2,899,000
MLS# 73359733
ACTIVE
$2,850,000
Winchester
22 Standish Lane, Winchester, MA, 01890
5 Beds
5 Baths
5,044 Sq ft
$2,850,000
MLS# 73353789
PENDING
3D Tour
$2,749,000
Winchester
Virtual Tour
35 Lawson Road, Winchester, MA, 01890
6 Beds
6 Baths
5,263 Sq ft
$2,749,000
MLS# 73352596
PENDING
$2,695,000
Winchester
18 Middlesex St, Winchester, MA, 01890
4 Beds
5 Baths
5,233 Sq ft
$2,695,000
MLS# 73347754
ACTIVE
$2,649,000
Winchester
3 Lagrange St, Winchester, MA, 01890
4 Beds
4 Baths
4,060 Sq ft
$2,649,000
MLS# 73324754
CONTRACT
$2,599,000
Winchester
89 Wildwood St, Winchester, MA, 01890
7 Beds
6 Baths
4,829 Sq ft
$2,599,000
MLS# 73350878
ACTIVE
$2,499,000
Winchester
9 Prospect St, Winchester, MA, 01890
6 Beds
4 Baths
4,667 Sq ft
$2,499,000
MLS# 73354228
ACTIVE
3D Tour
$2,499,000
Winchester
Virtual Tour
31 Lawson Rd, Winchester, MA, 01890
4 Beds
4 Baths
5,218 Sq ft
$2,499,000
MLS# 73351001
CONTRACT
3D Tour
$2,499,000
Winchester
Virtual Tour
50 Winford Way, Winchester, MA, 01890
5 Beds
5 Baths
4,270 Sq ft
$2,499,000
MLS# 73345594
PENDING
$2,499,000
Winchester
OPEN 04/19/25 1:00 - 3:00PM
19 Yale St, Winchester, MA, 01890
6 Beds
4 Baths
4,212 Sq ft
$2,499,000
MLS# 73360850
ACTIVE
3D Tour
$2,398,000
Winchester
Virtual Tour
74 Hillcrest Parkway, Winchester, MA, 01890
5 Beds
4 Baths
4,468 Sq ft
$2,398,000
MLS# 73344253
CONTRACT
3D Tour
$2,249,000
Winchester
Virtual Tour
48 Wedgemere Avenue, Winchester, MA, 01890
5 Beds
5 Baths
4,173 Sq ft
$2,249,000
MLS# 73334077
PENDING
3D Tour
$2,199,900
Winchester
Virtual Tour
OPEN 04/19/25 11:00AM - 12:30PM
11 Chesterford Rd E, Winchester, MA, 01890
4 Beds
4 Baths
3,039 Sq ft
$2,199,900
MLS# 73360401
ACTIVE
3D Tour
$2,050,000
Winchester
Virtual Tour
57 Jefferson Rd, Winchester, MA, 01890
4 Beds
4 Baths
3,274 Sq ft
$2,050,000
MLS# 73355738
PENDING
$1,949,000
Winchester
14 Grove Street, Winchester, MA, 01890
5 Beds
4 Baths
4,744 Sq ft
$1,949,000
MLS# 73358449
CONTRACT
$1,600,000
Winchester
149 Horn Pond Brook Rd, Winchester, MA, 01890
5 Beds
2 Baths
2,331 Sq ft
$1,600,000
MLS# 73251461
PENDING
3D Tour
$1,599,000
Winchester
Virtual Tour
OPEN 04/19/25 12:00 - 1:00PM
189 Mystic Valley Pkwy, Winchester, MA, 01890
6 Beds
3 Baths
3,543 Sq ft
$1,599,000
MLS# 73332625
ACTIVE
3D Tour
$1,549,000
Winchester
Virtual Tour
OPEN 04/19/25 1:30 - 2:30PM
34 Fells Road, Winchester, MA, 01890
3 Beds
4 Baths
3,351 Sq ft
$1,549,000
MLS# 73352886
ACTIVE
3D Tour
$1,529,000
Winchester
Virtual Tour
24 Water St, Winchester, MA, 01890
3 Beds
4 Baths
2,809 Sq ft
$1,529,000
MLS# 73346965
PENDING
$1,299,000
Winchester
261 Cambridge St UNIT 261, Winchester, MA, 01890
3 Beds
3 Baths
2,705 Sq ft
$1,299,000
MLS# 73342253
ACTIVE
$1,299,000
Winchester
261 Cambridge St UNIT 261, Winchester, MA, 01890
3 Beds
3 Baths
2,705 Sq ft
$1,299,000
MLS# 73342258
ACTIVE
3D Tour
$1,299,000
Winchester
Virtual Tour
OPEN 04/19/25 11:30AM - 1:00PM
10 Allen Rd, Winchester, MA, 01890
3 Beds
2 Baths
1,520 Sq ft
$1,299,000
MLS# 73356684
ACTIVE
$1,295,000
Winchester
OPEN 04/20/25 11:00AM - 12:00PM
71 Woodside Rd, Winchester, MA, 01890
4 Beds
2 Baths
2,202 Sq ft
$1,295,000
MLS# 73354724
ACTIVE
$1,250,000
Winchester
61 Westland Avenue, Winchester, MA, 01890
4 Beds
2 Baths
2,621 Sq ft
$1,250,000
MLS# 73353927
ACTIVE
$1,199,900
Winchester
36 Lebanon Street, Winchester, MA, 01890
3 Beds
2 Baths
2,060 Sq ft
$1,199,900
MLS# 73346408
PENDING
3D Tour
$1,199,000
Winchester
Virtual Tour
80 Harvard Street, Winchester, MA, 01890
4 Beds
2 Baths
2,759 Sq ft
$1,199,000
MLS# 73357438
CONTRACT
$1,149,000
Winchester
7 Indian Hill Road, Winchester, MA, 01890
3 Beds
2 Baths
1,646 Sq ft
$1,149,000
MLS# 73356058
CONTRACT
3D Tour
$1,149,000
Winchester
Virtual Tour
OPEN 04/19/25 11:00AM - 1:00PM
83 Canal, Winchester, MA, 01890
4 Beds
3 Baths
2,300 Sq ft
$1,149,000
MLS# 73360866
ACTIVE
3D Tour
$1,099,000
Winchester
Virtual Tour
160 Swanton Street UNIT 160, Winchester, MA, 01890
3 Beds
4 Baths
2,290 Sq ft
$1,099,000
MLS# 73350237
ACTIVE
$1,060,000
Winchester
62 Richardson St, Winchester, MA, 01890
5 Beds
3 Baths
2,849 Sq ft
$1,060,000
MLS# 73117876
PENDING
$999,999
Winchester
26 N Gateway, Winchester, MA, 01890
2 Beds
1 Baths
1,666 Sq ft
$999,999
MLS# 73340651
PENDING
$998,000
Winchester
OPEN 04/19/25 12:00 - 1:30PM
48 Tremont Street, Winchester, MA, 01890
4 Beds
3 Baths
2,333 Sq ft
$998,000
MLS# 73357199
ACTIVE
$975,000
Winchester
18 Pine Grove Park, Winchester, MA, 01890
3 Beds
2 Baths
2,873 Sq ft
$975,000
MLS# 73342281
PENDING
3D Tour
$869,900
Winchester
Virtual Tour
79 Sylvester Ave, Winchester, MA, 01890
3 Beds
2 Baths
1,469 Sq ft
$869,900
MLS# 73341343
PENDING
$699,900
Winchester
7 Conant Rd UNIT 20, Winchester, MA, 01890
2 Beds
2 Baths
1,168 Sq ft
$699,900
MLS# 73339113
ACTIVE
3D Tour
$695,000
Winchester
Virtual Tour
21 Shepard Court UNIT 21, Winchester, MA, 01890
2 Beds
1 Baths
1,393 Sq ft
$695,000
MLS# 73342978
PENDING
$655,000
Winchester
15 Charles Rd UNIT 15, Winchester, MA, 01890
2 Beds
2 Baths
968 Sq ft
$655,000
MLS# 73351345
PENDING
$11,000
Winchester
34 Glen Road, Winchester, MA, 01890
7 Beds
4 Baths
3,300 Sq ft
$11,000
MLS# 73355474
ACTIVE
$9,500
Winchester
23 Jefferson Road, Winchester, MA, 01890
6 Beds
5 Baths
3,118 Sq ft
$9,500
MLS# 73359523
ACTIVE
$8,500
Winchester
54 Spruce UNIT 1, Winchester, MA, 01890
5 Beds
4 Baths
3,500 Sq ft
$8,500
MLS# 73347270
ACTIVE
$8,000
Winchester
271 Washington UNIT 1, Winchester, MA, 01890
5 Beds
4 Baths
3,700 Sq ft
$8,000
MLS# 73345673
ACTIVE
$8,000
Winchester
846 Main Street UNIT 4, Winchester, MA, 01890
3 Beds
3 Baths
2,900 Sq ft
$8,000
MLS# 73354401
ACTIVE
$7,000
Winchester
40 Church UNIT A, Winchester, MA, 01890
4 Beds
4 Baths
4,000 Sq ft
$7,000
MLS# 73353399
ACTIVE
$6,000
Winchester
48 Spruce UNIT 48, Winchester, MA, 01890
4 Beds
4 Baths
2,500 Sq ft
$6,000
MLS# 73361043
ACTIVE
$5,000
Winchester
27 Ledyard Road UNIT sf, Winchester, MA, 01890
3 Beds
2 Baths
2,364 Sq ft
$5,000
MLS# 73318120
ACTIVE
$4,500
Winchester
171 Swanton Street UNIT 63, Winchester, MA, 01890
3 Beds
3 Baths
1,823 Sq ft
$4,500
MLS# 73356680
ACTIVE
$4,500
Winchester
17 Russell Rd, Winchester, MA, 01890
3 Beds
2 Baths
1,657 Sq ft
$4,500
MLS# 73340350
ACTIVE
$4,200
Winchester
8 Richardson Street UNIT 2, Winchester, MA, 01890
2 Beds
2 Baths
1,811 Sq ft
$4,200
MLS# 73358995
ACTIVE
$3,250
Winchester
115 Washington Street UNIT 2B, Winchester, MA, 01890
2 Beds
1 Baths
1,057 Sq ft
$3,250
MLS# 73343052
ACTIVE
$3,100
Winchester
16 Water St UNIT 1, Winchester, MA, 01890
2 Beds
1 Baths
1,200 Sq ft
$3,100
MLS# 73350562
PENDING
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Price
BedsSqftLot SizeBathsPriceYear BuiltCreated AtTotal ImagesDays on the Market
Descending
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12
122448
Winchester
19 Rangeley Rd, Winchester, MA, 01890
5 Beds
7 Baths
7,779 Sq ft
$4,799,000
MLS# 73341968
PENDING
Winchester
3 Foxcroft Road, Winchester, MA, 01890
6 Beds
6 Baths
5,208 Sq ft
$4,200,000
MLS# 73334088
PENDING
Winchester
Virtual Tour
6 Vinson Cir, Winchester, MA, 01890
6 Beds
8 Baths
7,500 Sq ft
$4,199,000
MLS# 73328916
PENDING
Winchester
Virtual Tour
OPEN 04/19/25 11:00AM - 12:00PM
26 Swan Road, Winchester, MA, 01890
6 Beds
7 Baths
8,463 Sq ft
$3,989,000
MLS# 73344473
ACTIVE
Winchester
20 Amberwood Dr, Winchester, MA, 01890
6 Beds
7 Baths
8,866 Sq ft
$3,898,000
MLS# 73348642
ACTIVE
Winchester
11 Viking Rd, Winchester, MA, 01890
7 Beds
8 Baths
7,429 Sq ft
$3,799,900
MLS# 73355068
ACTIVE
Winchester
Virtual Tour
54 Johnson Road, Winchester, MA, 01890
7 Beds
8 Baths
7,982 Sq ft
$3,699,000
MLS# 73335471
ACTIVE
Winchester
2 Chestnut St, Winchester, MA, 01890
6 Beds
5 Baths
5,500 Sq ft
$3,599,000
MLS# 73333668
CONTRACT
Winchester
27 Everett Ave, Winchester, MA, 01890
6 Beds
6 Baths
7,431 Sq ft
$3,599,000
MLS# 73356139
ACTIVE
Winchester
4 Norwood St, Winchester, MA, 01890
5 Beds
5 Baths
5,250 Sq ft
$3,499,000
MLS# 73333712
ACTIVE
Winchester
58 Wedgemere Ave, Winchester, MA, 01890
5 Beds
5 Baths
4,800 Sq ft
$3,450,000
MLS# 73334029
PENDING
Winchester
Virtual Tour
21 Sheffield West, Winchester, MA, 01890
6 Beds
5 Baths
5,198 Sq ft
$3,350,000
MLS# 73350559
ACTIVE

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