Winchester, MA - single-family homes for sale

30 of 30 results displayed

Open Sat, 1 to 2:30pmNew
$1,199,000Active
3 beds 2 baths1,973 sq. ft.
15 East Street, Winchester, MA 01890
MLS# 73493684Listed by: Compass
New
$1,750,000Active
6 beds 5 baths3,833 sq. ft.
12 Wincrest Drive, Winchester, MA 01890
MLS# 73492714Listed by: Compass
New
$999,000Active
4 beds 2 baths1,552 sq. ft.
76 Woodside Road, Winchester, MA 01890
MLS# 73492483Listed by: Mystic Properties Real Estate
Open Sat, 1 to 2:30pmNew
$2,649,000Active
4 beds 5 baths5,614 sq. ft.
2 Abby Rd, Winchester, MA 01890
MLS# 73492061Listed by: Gibson Sotheby's International Realty
Open Sat, 12 to 1:30pmNew
$1,749,000Active
5 beds 3 baths3,271 sq. ft.
29 Pilgrim Dr, Winchester, MA 01890
MLS# 73491480Listed by: Barrett Sotheby's International Realty
New
$2,795,000Active
5 beds 4 baths4,792 sq. ft.
56 Yale Street, Winchester, MA 01890
MLS# 73491616Listed by: Brad Hutchinson Real Estate
Open Sat, 12 to 1:30pmNew
$2,250,000Active
7 beds 4 baths3,926 sq. ft.
10 Edgehill Road, Winchester, MA 01890
MLS# 73490604Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$3,747,000Active
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
$1,799,000Active
4 beds 3 baths2,910 sq. ft.
58 Jefferson Road, Winchester, MA 01890
MLS# 73488901Listed by: Wilson Wolfe Real Estate
Open Sat, 12:30 to 1:30pm
$3,299,000Active
5 beds 4 baths4,028 sq. ft.
10 Dartmouth Street, Winchester, MA 01890
MLS# 73488384Listed by: Compass
Open Sat, 1 to 2pm
$1,524,000Active
4 beds 3 baths3,380 sq. ft.
34 Robinhood Road, Winchester, MA 01890
MLS# 73486878Listed by: RE/MAX Real Estate Center
Open Sat, 11:30am to 1pm
$3,650,000Active
6 beds 5 baths6,460 sq. ft.
40 Foxcroft Rd, Winchester, MA 01890
MLS# 73485774Listed by: Serhant
$1,499,999Active
6 beds 3 baths2,658 sq. ft.
65 High Street, Winchester, MA 01890
MLS# 73485189Listed by: K Stadium Realty INC
$4,699,000Active
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
$2,965,000Active
7 beds 8 baths7,043 sq. ft.
45 Bacon Street, Winchester, MA 01890
MLS# 73479961Listed by: Compass
$1,095,000Active
5 beds 2 baths2,331 sq. ft.
149 Horn Pond Brook Road, Winchester, MA 01890
MLS# 73478668Listed by: Redfin Corp.
$3,537,000Active
7 beds 8 baths8,540 sq. ft.
37 Mayflower Road, Winchester, MA 01890
MLS# 73475646Listed by: Compass
Open Sat, 12 to 1:30pm
$3,425,000Active
7 beds 8 baths7,226 sq. ft.
15 Mayflower Rd, Winchester, MA 01890
MLS# 73474189Listed by: Douglas Elliman Real Estate - The Sarkis Team
$3,390,000Active
4 beds 4 baths4,847 sq. ft.
25 Myopia Road, Winchester, MA 01890
MLS# 73471735Listed by: Engel & Volkers Boston
$2,499,000Active
4 beds 4 baths5,674 sq. ft.
10 Viking Rd, Winchester, MA 01890
MLS# 73467030Listed by: Barrett Sotheby's International Realty
$1,899,000Active
3 beds 4 baths3,010 sq. ft.
1 Town Way, Winchester, MA 01890
MLS# 73466233Listed by: Compass
Open Sat, 11:30am to 12:30pm
$1,945,000Active
5 beds 4 baths4,334 sq. ft.
237 Swanton Street, Winchester, MA 01890
MLS# 73459838Listed by: Compass
Open Sat, 12 to 1pm
$2,799,000Active
5 beds 4 baths5,083 sq. ft.
53 Winford Way, Winchester, MA 01890
MLS# 73481323Listed by: Keller Williams Realty Boston Northwest
Open Sat, 1:30 to 2:30pm
$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
Open Sat, 11am to 12pm
$3,499,000Active
5 beds 8 baths6,899 sq. ft.
54 Johnson Rd, Winchester, MA 01890
MLS# 73474290Listed 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.