Winchester, MA - single-family homes for sale

36 of 36 results displayed

New
$1,099,000Active
4 beds 3 baths2,411 sq. ft.
24 Richardson St, Winchester, MA 01890
MLS# 73571480Listed by: Keller Williams Realty Boston Northwest
New
$1,050,000Active
5 beds 3 baths2,801 sq. ft.
257 Cross Street, Winchester, MA 01890
MLS# 73571418Listed by: Compass
New
$2,849,000Active
5 beds 5 baths5,058 sq. ft.
7 Viking Rd, Winchester, MA 01890
MLS# 73569252Listed by: Keller Williams Realty Boston Northwest
$1,699,000Active
5 beds 4 baths3,180 sq. ft.
30 Farrow St, Winchester, MA 01890
MLS# 73568493Listed by: Compass
$1,098,000Active
3 beds 2 baths1,657 sq. ft.
17 Russell Rd, Winchester, MA 01890
MLS# 73566405Listed by: Kwan Realty Inc.
$1,999,000Active
4 beds 3 baths3,757 sq. ft.
85 High St, Winchester, MA 01890
MLS# 73565817Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$3,199,000Active
5 beds 5 baths5,406 sq. ft.
10 Rangeley Road, Winchester, MA 01890
MLS# 73561672Listed by: Compass
$3,295,000Active
6 beds 7 baths6,100 sq. ft.
2 Atherton Rd, Winchester, MA 01890
MLS# 73563095Listed by: Serhant
$1,329,000Active
3 beds 3 baths2,459 sq. ft.
110 Thornberry Road, Winchester, MA 01890
MLS# 73562273Listed by: Kiklis Real Estate, LLC
$2,499,000Active
4 beds 5 baths4,450 sq. ft.
54 Squire Road, Winchester, MA 01890
MLS# 73555666Listed by: The Marino Group Collection
$949,999Active
4 beds 2 baths2,326 sq. ft.
96 Loring Ave, Winchester, MA 01890
MLS# 73561829Listed by: StartPoint Realty
$3,450,000Active
6 beds 5 baths5,735 sq. ft.
7 Hutchinson Road, Winchester, MA 01890
MLS# 73561703Listed by: Compass
$3,200,000Active
5 beds 6 baths5,295 sq. ft.
18 Ridge St, Winchester, MA 01890
MLS# 73561372Listed by: Compass
$2,999,000Active
5 beds 4 baths4,500 sq. ft.
5 Forest Cir, Winchester, MA 01890
MLS# 73560088Listed by: Gibson Sotheby's International Realty
$1,549,000Active
3 beds 3 baths2,640 sq. ft.
50 Holland Street, Winchester, MA 01890
MLS# 73556633Listed by: Compass
$3,600,000Active
7 beds 8 baths7,429 sq. ft.
11 Viking Road, Winchester, MA 01890
MLS# 73556474Listed by: Engel & Volkers Boston
$1,794,000Active
3 beds 4 baths3,010 sq. ft.
1 Town Way, Winchester, MA 01890
MLS# 73555777Listed by: Compass
$849,000Active
3 beds 2 baths1,340 sq. ft.
15 Clark St, Winchester, MA 01890
MLS# 73555218Listed by: Coldwell Banker Realty - Milton
$950,000Active
3 beds 2 baths1,356 sq. ft.
47 Water Street, Winchester, MA 01890
MLS# 73549935Listed by: Leading Edge Real Estate
$2,999,000Active
5 beds 4 baths4,028 sq. ft.
10 Dartmouth Street, Winchester, MA 01890
MLS# 73548103Listed by: Compass
$1,899,000Active
5 beds 4 baths3,210 sq. ft.
79 Grove St, Winchester, MA 01890
MLS# 73545952Listed by: Gibson Sotheby's International Realty
$2,500,000Active
5 beds 3 baths4,071 sq. ft.
9 Plymouth Rd, Winchester, MA 01890
MLS# 73544924Listed by: Real Broker MA, LLC
$849,000Active
4 beds 2 baths2,083 sq. ft.
84 Oak Street, Winchester, MA 01890
MLS# 73542597Listed by: Charlesgate Realty Group LLC
$1,350,000Active
4 beds 3 baths2,690 sq. ft.
423 Washington St, Winchester, MA 01890
MLS# 73541775Listed by: MA Properties
$999,900Active
4 beds 2 baths1,719 sq. ft.
258 Cross Street, Winchester, MA 01890
MLS# 73541288Listed by: Fiv Realty Co
$1,050,000Active
3 beds 2 baths1,711 sq. ft.
150 Cambridge Street, Winchester, MA 01890
MLS# 73530959Listed by: Plunkett Properties
$1,075,000Active
3 beds 3 baths2,235 sq. ft.
53 Lake Street, Winchester, MA 01890
MLS# 73519082Listed by: Compass
$2,695,000Active
4 beds 5 baths5,233 sq. ft.
18 Middlesex St, Winchester, MA 01890
MLS# 73518621Listed by: Luxury Living Real Estate
$2,100,000Active
6 beds 5 baths3,403 sq. ft.
6 Ivy Circle, Winchester, MA 01890
MLS# 73510713Listed by: Engel & Volkers Boston
$2,799,000Active
6 beds 7 baths6,968 sq. ft.
14 Nassau Drive, Winchester, MA 01890
MLS# 73500890Listed by: WINN Real Estate & Consulting
$3,299,000Active
7 beds 8 baths7,226 sq. ft.
1 Plymouth Rd, Winchester, MA 01890
MLS# 73498293Listed by: Douglas Elliman Real Estate - The Sarkis Team
$2,195,000Active
5 beds 4 baths5,006 sq. ft.
276 High Street, Winchester, MA 01890
MLS# 73496396Listed by: Compass
$3,200,000Active
6 beds 6 baths6,100 sq. ft.
9 Albamont Road, Winchester, MA 01890
MLS# 73482275Listed by: Compass
$949,900Active
4 beds 3 baths1,880 sq. ft.
116 Forest St, Winchester, MA 01890
MLS# 73179157Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate
$2,799,000Active
5 beds 6 baths6,067 sq. ft.
10 North Gateway, Winchester, MA 01890
MLS# 73158946Listed by: Compass
$2,799,000Active
5 beds 5 baths5,000 sq. ft.
1 Alice Lane, Winchester, MA 01890
MLS# 73107072Listed by: Compass

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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation Submit agent or broker complaint

Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.

©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.