Winchester, MA - single-family homes for sale

37 of 37 results displayed

New
$1,925,000Active
5 beds 4 baths3,315 sq. ft.
8 Hawthorne, Winchester, MA 01890
MLS# 73522773Listed by: Coldwell Banker Realty - Lexington
Open Sat, 11am to 1pmNew
$1,250,000Active
3 beds 2 baths2,192 sq. ft.
2 Eaton Ct, Winchester, MA 01890
MLS# 73522338Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
Open Sat, 1 to 2:30pmNew
$1,300,000Active
3 beds 2 baths1,511 sq. ft.
6 Alden Lane, Winchester, MA 01890
MLS# 73520993Listed by: Gibson Sotheby's International Realty
Open Sat, 11am to 12:30pmNew
$1,689,000Active
3 beds 2 baths3,090 sq. ft.
41 Sunset Road, Winchester, MA 01890
MLS# 73520906Listed by: Compass
Open Sat, 11am to 12pmNew
$999,000Active
4 beds 2 baths2,085 sq. ft.
41 Cross St, Winchester, MA 01890
MLS# 73520534Listed by: Keller Williams Realty Boston Northwest
Open Sat, 2 to 3:30pmNew
$799,000Active
3 beds 1 baths1,245 sq. ft.
55 Brookside Ave., Winchester, MA 01890
MLS# 73517006Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
New
$3,600,000Active
6 beds 7 baths7,400 sq. ft.
2 Atherton Rd, Winchester, MA 01890
MLS# 73519229Listed by: Regatta Realty
Open Sun, 11am to 12:30pmNew
$1,225,000Active
3 beds 3 baths2,235 sq. ft.
53 Lake Street, Winchester, MA 01890
MLS# 73519082Listed by: Compass
New
$2,795,000Active
4 beds 5 baths4,319 sq. ft.
18 Middlesex St, Winchester, MA 01890
MLS# 73518621Listed by: Luxury Living Real Estate
New
$2,750,000Active
6 beds 5 baths4,540 sq. ft.
47 Yale Street, Winchester, MA 01890
MLS# 73516849Listed by: Coldwell Banker Realty - Belmont
New
$1,300,000Active
4 beds 3 baths2,666 sq. ft.
465 Washington St, Winchester, MA 01890
MLS# 73516539Listed by: Gibson Sotheby's International Realty
$2,495,000Active
6 beds 4 baths5,121 sq. ft.
112 Highland Avenue, Winchester, MA 01890
MLS# 73515135Listed by: Compass
$3,250,000Active
5 beds 6 baths6,500 sq. ft.
8 Priscilla Ln, Winchester, MA 01890
MLS# 73513501Listed by: Rise Signature Homes
$2,975,000Active
7 beds 6 baths5,888 sq. ft.
115 Church St, Winchester, MA 01890
MLS# 73512327Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$1,699,000Active
4 beds 3 baths2,818 sq. ft.
12 Cox Rd, Winchester, MA 01890
MLS# 73511596Listed by: RE/MAX Bentley's
$3,099,000Active
5 beds 5 baths5,406 sq. ft.
10 Rangeley Road, Winchester, MA 01890
MLS# 73511033Listed by: Compass
Open Sat, 11am to 12:30pm
$2,595,000Active
4 beds 4 baths4,403 sq. ft.
50 Brooks Street, Winchester, MA 01890
MLS# 73510897Listed by: Compass
Open Sun, 1 to 2pm
$2,000,000Active
6 beds 5 baths3,403 sq. ft.
6 Ivy Circle, Winchester, MA 01890
MLS# 73510713Listed by: Engel & Volkers Boston
Open Sat, 11:30am to 1pm
$1,250,000Active
5 beds 2 baths2,688 sq. ft.
6 Hancock St, Winchester, MA 01890
MLS# 73510153Listed by: Gibson Sotheby's International Realty
$3,379,000Active
7 beds 8 baths8,540 sq. ft.
37 Mayflower Road, Winchester, MA 01890
MLS# 73502853Listed by: Compass
$2,799,000Active
6 beds 7 baths6,968 sq. ft.
14 Nassau Drive, Winchester, MA 01890
MLS# 73500890Listed by: WINN Real Estate & Consulting
Open Sat, 12:30 to 1:30pm
$2,950,000Active
5 beds 5 baths5,202 sq. ft.
74 Wedgemere Avenue, Winchester, MA 01890
MLS# 73499151Listed by: Compass
$2,700,000Active
4 beds 5 baths3,945 sq. ft.
2 Edgewater Place, Winchester, MA 01890
MLS# 73498843Listed by: Gibson Sotheby's International Realty
Open Sat, 10:30am to 12pm
$929,900Active
4 beds 2 baths1,938 sq. ft.
380 Cross Street, Winchester, MA 01890
MLS# 73498603Listed by: Coldwell Banker Realty - Lexington
$3,399,000Active
7 beds 8 baths7,226 sq. ft.
1 Plymouth Rd, Winchester, MA 01890
MLS# 73498293Listed by: Douglas Elliman Real Estate - The Sarkis Team
Open Sun, 1 to 2pm
$2,195,000Active
5 beds 4 baths5,006 sq. ft.
276 High Street, Winchester, MA 01890
MLS# 73496396Listed by: Compass
$3,475,000Active
7 beds 6 baths7,043 sq. ft.
2 Everett Ave, Winchester, MA 01890
MLS# 73488991Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$3,549,000Active
6 beds 5 baths6,460 sq. ft.
40 Foxcroft Rd, Winchester, MA 01890
MLS# 73485774Listed by: Serhant
$4,449,000Active
5 beds 6 baths6,526 sq. ft.
4 Dartmouth St, Winchester, MA 01890
MLS# 73482952Listed by: Gibson Sotheby's International Realty
$3,400,000Active
6 beds 6 baths6,100 sq. ft.
9 Albamont Road, Winchester, MA 01890
MLS# 73482275Listed by: Compass
$1,799,000Active
3 beds 4 baths3,010 sq. ft.
1 Town Way, Winchester, MA 01890
MLS# 73466233Listed by: Compass
Open Sat, 12:30 to 1:30pm
$2,799,000Active
5 beds 4 baths5,083 sq. ft.
53 Winford Way, Winchester, MA 01890
MLS# 73481323Listed by: Keller Williams Realty Boston Northwest
$3,600,000Active
6 beds 7 baths8,866 sq. ft.
20 Amberwood Dr, Winchester, MA 01890
MLS# 73423693Listed by: WW Real Estate LLC
$3,290,000Active
6 beds 6 baths7,431 sq. ft.
27 Everett Ave, Winchester, MA 01890
MLS# 73468691Listed by: Gibson Sotheby's International Realty
$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.