Winchester, MA - single-family homes for sale

48 of 48 results displayed

Open Sat, 11:30am to 1pmNew
$2,650,000Active
4 beds 5 baths5,233 sq. ft.
18 Middlesex St, Winchester, MA 01890
MLS# 73593868Listed by: Coldwell Banker Realty - Boston
New
$3,799,000Active
8 beds 6 baths7,081 sq. ft.
15 Foxcroft Rd, Winchester, MA 01890
MLS# 73593484Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
New

$2,950,000Active
6 beds 4 baths4,752 sq. ft.
18 Surrey Road, Winchester, MA 01890
MLS# 73592433Listed by: Century 21 Property Central Inc.
New
$1,125,000Active
3 beds 2 baths1,684 sq. ft.
8 Stone Ave, Winchester, MA 01890
MLS# 73591400Listed by: Barrett Sotheby's International Realty
Open Sun, 11:30am to 1pmNew
$890,000Active
2 beds 1 baths1,489 sq. ft.
80 Nelson St, Winchester, MA 01890
MLS# 73591108Listed by: Compass
Open Sat, 12 to 1:30pmNew
$1,399,000Active
3 beds 3 baths1,975 sq. ft.
6 Aricia Ln, Winchester, MA 01890
MLS# 73590311Listed by: Gibson Sotheby's International Realty
Open Sun, 1 to 2:30pm
$1,985,000Active
4 beds 4 baths4,241 sq. ft.
30 Surrey Rd, Winchester, MA 01890
MLS# 73589478Listed by: Barrett Sotheby's International Realty
$1,399,000Active
5 beds 2 baths2,071 sq. ft.
15 Lloyd Street, Winchester, MA 01890
MLS# 73588977Listed by: Compass
$1,299,000Active
3 beds 2 baths2,350 sq. ft.
39 Forest St, Winchester, MA 01890
MLS# 73588863Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate
Open Sat, 11:30am to 1pm
$2,049,000Active
5 beds 4 baths4,063 sq. ft.
21 Amberwood Dr, Winchester, MA 01890
MLS# 73588059Listed by: Compass
$2,399,000Active
4 beds 4 baths3,550 sq. ft.
63 Wedgemere Avenue, Winchester, MA 01890
MLS# 73587441Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
Open Sat, 1:30 to 2:30pm
$850,000Active
3 beds 1 baths1,313 sq. ft.
39 Henry Street, Winchester, MA 01890
MLS# 73585414Listed by: Coldwell Banker Realty - Belmont
$18,000,000Active
6 beds 7 baths10,000 sq. ft.
15 Vinson Circle, Winchester, MA 01890
MLS# 73585235Listed by: The Marino Group Collection
$3,299,000Active
7 beds 8 baths7,226 sq. ft.
1 Plymouth Rd., Winchester, MA 01890
MLS# 73585058Listed by: Gibson Sotheby's International Realty
$1,529,000Active
4 beds 4 baths2,709 sq. ft.
25 Arlington St, Winchester, MA 01890
MLS# 73584817Listed by: Coldwell Banker Realty - Lexington
$1,750,000Active
4 beds 3 baths3,604 sq. ft.
1 Overlook Way, Winchester, MA 01890
MLS# 73581571Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$1,325,000Active
4 beds 2 baths1,922 sq. ft.
9 Priscilla Ln, Winchester, MA 01890
MLS# 73579538Listed by: Compass
Open Sat, 1:30 to 2:30pm
$2,400,000Active
6 beds 4 baths3,534 sq. ft.
7 Lakeview Terrace, Winchester, MA 01890
MLS# 73578443Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate
Open Sat, 2:30 to 4pm
$3,200,000Active
8 beds 7 baths5,750 sq. ft.
30 Willowdale Rd, Winchester, MA 01890
MLS# 73577116Listed by: Gibson Sotheby's International Realty
Open Sat, 3 to 4:30pm
$974,900Active
3 beds 3 baths1,719 sq. ft.
258 Cross St, Winchester, MA 01890
MLS# 73575764Listed by: Fiv Realty Co
$4,299,000Active
5 beds 6 baths6,526 sq. ft.
4 Dartmouth, Winchester, MA 01890
MLS# 73574948Listed by: Gibson Sotheby's International Realty
Open Sat, 11:30am to 12:30pm
$3,149,000Active
7 beds 8 baths8,540 sq. ft.
37 Mayflower Road, Winchester, MA 01890
MLS# 73573670Listed by: Compass
$1,650,000Active
5 beds 4 baths3,722 sq. ft.
117 Highland, Winchester, MA 01890
MLS# 73573887Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$1,749,000Active
5 beds 4 baths3,508 sq. ft.
17 Churchill Rd, Winchester, MA 01890
MLS# 73572890Listed by: Coldwell Banker Realty - Lexington
Open Sun, 11:30am to 1pm
$2,199,000Active
4 beds 4 baths3,570 sq. ft.
19 Hancock Street, Winchester, MA 01890
MLS# 73572955Listed by: Compass
Open Sat, 11:30am to 1pm
$1,599,000Active
4 beds 2 baths2,421 sq. ft.
4 Churchill Road, Winchester, MA 01890
MLS# 73572661Listed by: Compass
Open Sat, 12:30 to 1:30pm
$1,069,000Active
4 beds 3 baths2,411 sq. ft.
24 Richardson St, Winchester, MA 01890
MLS# 73571480Listed by: Keller Williams Realty Boston Northwest
$1,050,000Active
5 beds 3 baths2,801 sq. ft.
257 Cross Street, Winchester, MA 01890
MLS# 73571418Listed by: Compass
$1,098,000Active
3 beds 2 baths1,657 sq. ft.
17 Russell Rd, Winchester, MA 01890
MLS# 73566405Listed by: Kwan Realty Inc.
Open Sat, 12 to 1pm
$1,899,000Active
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
$1,289,000Active
3 beds 3 baths2,459 sq. ft.
110 Thornberry Road, Winchester, MA 01890
MLS# 73562273Listed by: Kiklis Real Estate, LLC
Open Sat, 1 to 2:30pm
$2,399,000Active
4 beds 5 baths4,450 sq. ft.
54 Squire Road, Winchester, MA 01890
MLS# 73555666Listed by: The Marino Group Collection
$919,999Active
4 beds 2 baths2,326 sq. ft.
96 Loring Ave, Winchester, MA 01890
MLS# 73561829Listed by: StartPoint Realty
Open Sun, 1 to 2pm
$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
$1,549,000Active
3 beds 3 baths2,640 sq. ft.
50 Holland Street, Winchester, MA 01890
MLS# 73556633Listed by: Compass
Open Sat, 12:30 to 1:30pm
$3,600,000Active
7 beds 8 baths7,429 sq. ft.
11 Viking Road, Winchester, MA 01890
MLS# 73556474Listed by: Engel & Volkers Boston
Open Sun, 11:30am to 1pm
$1,749,000Active
3 beds 4 baths3,010 sq. ft.
1 Town Way, Winchester, MA 01890
MLS# 73555777Listed by: Compass
Open Sat, 11am to 12:30pm
$899,000Active
3 beds 2 baths1,356 sq. ft.
47 Water Street, Winchester, MA 01890
MLS# 73549935Listed by: Leading Edge Real Estate
$2,250,000Active
5 beds 3 baths4,071 sq. ft.
9 Plymouth Rd, Winchester, MA 01890
MLS# 73544924Listed by: Real Broker MA, LLC
Open Sat, 11am to 12:30pm
$1,025,000Active
3 beds 3 baths2,235 sq. ft.
53 Lake Street, Winchester, MA 01890
MLS# 73519082Listed by: Compass
Open Sat, 11am to 12pm
$2,100,000Active
6 beds 5 baths3,403 sq. ft.
6 Ivy Circle, Winchester, MA 01890
MLS# 73510713Listed by: Engel & Volkers Boston
$2,750,000Active
6 beds 7 baths6,968 sq. ft.
14 Nassau Drive, Winchester, MA 01890
MLS# 73500890Listed by: WINN Real Estate & Consulting
$2,195,000Active
5 beds 4 baths5,006 sq. ft.
276 High Street, Winchester, MA 01890
MLS# 73496396Listed by: Compass
Open Sun, 1 to 2pm
$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

Local realty services provided by:CENTURY 21 Tassinari & Associates, Inc

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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.