- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
104 Properties Available In Winchester
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$1,800
Condo
200 Swanton #502, Winchester, MA 01890
Sparkling, recently renovated studio with amazing views of a beautifully landscaped garden and pond. This rental unit is...
Listed by Susan Murie of Aikenhead Real Estate, Inc.

$3,800
Multi-Family, Townhouse
38 Florence Street #38, Winchester, MA 01890
3-Bed / 2 Full-bath apartment in a desirable Winchester neighborhood for rent. Situated at a quiet street, this three-be...
Listed by WINN Rental Team of WINN Real Estate & Consulting

$4,950
Single Family Home
137 Ridge St, Winchester, MA 01890
Available 5/1/25! Set in one of Greater Boston's most sought-after communities, this oversized 5-bed, 2-bath Cape offers...
Listed by The Elle Group of Berkshire Hathaway HomeServices Commonwealth Real Estate

$2,599,000
Single Family Home
15 Churchill Road, Winchester, MA 01890
Indulge in modern luxury with this stunning home, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamle...
Listed by Kim Covino & Co. Team of Compass

$699,900
Single Family Home
32 Clark St, Winchester, MA 01890
A true diamond in the rough, Whether you're a first-time homebuyer, a savvy investor, or someone looking to customize a ...
Listed by Rodrigo Serrano of Leading Edge Real Estate

$1,199,000
Single Family Home
44 Forest Street, Winchester, MA 01890
This charming home is move-in ready and situated on a beautiful fenced in level lot close to parks, the bike path, Murac...
Listed by Kim Covino & Co. Team of Compass

$1,499,000
Single Family Home
19 Cox Road, Winchester, MA 01890
Charming three-bedroom ranch on spectacular 20,000sf west side lot abutting conservation! The updated granite kitchen wi...
Listed by Kim Covino & Co. Team of Compass

$1,269,000
Condo
158 Swanton Street #158, Winchester, MA 01890
Welcome to 158 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craf...
Listed by The Marrocco Group of Coldwell Banker Realty - Lexington

$3,900
Condo
90 Sylvester Ave #90, Winchester, MA 01890
Available now! This 2016-built 3-bedroom, 2-bath condo plus den offers modern living with an open-concept layout and har...
Listed by The Elite Team of Phoenix Real Estate Partners, LLC

$1,375,000
Single Family Home
7 Hutchinson Rd, Winchester, MA 01890
A great opportunity to reimagine this custom built spacious cape in a sought-after Winchester neighborhood! Set on a gen...
Listed by Kim Covino & Co. Team of Compass

$1,995,000
Single Family Home
20 Seneca Road, Winchester, MA 01890
Welcome home to this picture-perfect Colonial, tucked away in a quiet, sought-after neighborhood just steps from Ambrose...
Listed by Stephanie Mcgowan of Better Homes and Gardens Real Estate - The Shanahan Group

$4,800
Condo
4 Dix Terrace #4, Winchester, MA 01890
Stunning 2-Bedroom 2-Bathroom beautifully constructed multi-family apartment walking distance to Winchester Center. Prid...
Listed by Rachel Ventresca of Greater Metropolitan R. E.

$1,499,900
Single Family Home
7 Thornberry Road, Winchester, MA 01890
Renovated Contemporary Split-entry 3 Level home in the highly sought-after Vinson- Owen Elementary and West-side neighbo...
Listed by Salim Chowdhury of TAJ Mahal Realty LLC

$749,900
Condo
7 Conant Rd #34, Winchester, MA 01890
Rarely available at The Willows, you enter this unit with ease through your private, attached one car garage or the step...
Listed by Melanie Lentini of Leading Edge Real Estate

$1,949,000
Single Family Home
10 Olde Lyme Road, Winchester, MA 01890
Beautifully updated 5 bed, 3.5 bath Colonial on Winchester's West Side with over 3400 sq ft of living space located on a...
Listed by Darryl E. Brian of RE/MAX Bentley's

$2,680
Condo
200 Swanton St #239, Winchester, MA 01890
Enjoy scenic water views from this beautifully updated second-floor condo, perfectly situated overlooking the pond. This...
Listed by Joan Powell of Advisors Living - Merrimac

$1,650,000
Single Family Home
14 Hillside Ave, Winchester, MA 01890
Location, location, location! Rare opportunity to own this stunning Italianate home, in a desirable neighborhood, steps ...
Listed by Seeme Moreira of Coldwell Banker Realty - Lexington

$11,000
Single Family Home
31 Coolidge St #0, Winchester, MA 01890
Available now! Welcome to this beautifully renovated and maintained colonial at a very quiet street in a desirable neigh...
Listed by Carlos Xu of Lexwin Realty

$6,000
Multi-Family, Townhouse
48 Spruce #48, Winchester, MA 01890
Walk to town from this completely renovated 4 bedroom, 3.5 bath, 4 level attached home. Excellent finishes and space. B...
Listed by Julia Marino of Archambault Real Estate

$1,149,000
Condo
83 Canal #83, Winchester, MA 01890
This beautifully renovated, light-filled condo blends classic charm with modern updates in an ideal Winchester location....
Listed by Mary O'Hagan of Barrett Sotheby's International Realty

$2,499,000
Single Family Home
19 Yale St, Winchester, MA 01890
Located in the TOP neighborhood that everyone wants! Welcome to the Flats, where elegance and charm abound. A gorgeous f...
Listed by The Pallotta Group of Advisors Living - Winchester

$2,199,900
Single Family Home
11 Chesterford Rd E, Winchester, MA 01890
Stunning waterfront home on Little Winter Pond offers the perfect blend of modern design and serene natural beauty! Thou...
Listed by Joseph Pollack of Redfin Corp.

$2,950,000
Single Family Home
14 Nassau Drive, Winchester, MA 01890
Stunning Absolutely! Custom-built 6-bedroom house on a large and tranquil lot. This beautiful home welcomes you with a m...
Listed by Weidong Li of WINN Real Estate & Consulting

$2,899,000
Single Family Home
11 Taft Dr, Winchester, MA 01890
Luxury and location converge in this stunning 5-bedroom, 5.5-bathroom home nestled in one of Winchester's most coveted W...
Listed by The Marrocco Group of Coldwell Banker Realty - Lexington