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24 Properties Available In Winchester
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- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
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- Square Feet (Biggest)

$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

$1,375,000
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

$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

$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

$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

$2,950,000
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

$998,000
Single Family Home
48 Tremont Street, Winchester, MA 01890
Welcome to this well loved 4-bedroom expanded Cape, on quiet cul-de-sac, cared for by the original owners for nearly 65 ...
Listed by Michael Rauseo of Better Homes and Gardens Real Estate - The Shanahan Group

$1,299,000
Single Family Home
10 Allen Rd, Winchester, MA 01890
Located in a very desirable East Hill neighborhood, this one owner Circa 1929 Dutch Colonial offers a wonderful opportun...
Listed by Sally Baldwin of Coldwell Banker Realty - Lexington

$3,599,000
Single Family Home
27 Everett Ave, Winchester, MA 01890
Completely renovated in 2023/2024! This is one of the most distinguished homes on Everett Avenue, with preeminent sitin...
Listed by The Pallotta Group of Advisors Living - Winchester

$2,449,000
Single Family Home
5 Azalea Rd, Winchester, MA 01890
Exceptional Home nestled in one of Winchester's most desirable West Side Neighborhoods and on a Cul de Sac! Open Floor P...
Listed by Giordana Fioravanti Smith of Berkshire Hathaway HomeServices Commonwealth Real Estate

$1,295,000
Single Family Home
71 Woodside Rd, Winchester, MA 01890
Nestled in the heart of Winchester, this charming 4-bedroom, 1.5-bathroom single-family home offers 2,202 square feet of...
Listed by Jorge Rodriguez of Carlton's Wharf & Co.

$2,499,000
Single Family Home
9 Prospect St, Winchester, MA 01890
Step into a piece of history with this incredibly charming 1895 Colonial Revival, a home that exudes elegance, character...
Listed by The Pallotta Group of Advisors Living - Winchester

$1,199,000
Single Family Home
61 Westland Avenue, Winchester, MA 01890
Welcome to this oversized Cape in a lovely west side neighborhood of Winchester. Opportunity for a little TLC or a sign...
Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

$1,499,000
Single Family Home
34 Fells Road, Winchester, MA 01890
Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort a...
Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest

$2,599,000
Single Family Home
89 Wildwood St, Winchester, MA 01890
NEW CONSTRUCTION! This stunning 7-bed, 5.5-bath luxury home boasts high-end finishes and a thoughtfully designed open fl...
Listed by The Marrocco Group of Coldwell Banker Realty - Lexington

$2,399,000
Single Family Home
276 High Street, Winchester, MA 01890
This stunning, freshly painted, home is located in a picturesque and unique setting, elevated on a small hill with a pri...
Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest

$3,149,000
Single Family Home
10 Sheffield Road, Winchester, MA 01890
This stunning Colonial Revival home, situated on one of Winchester's most desirable streets, is just moments from the tr...
Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest

$3,698,000
Single Family Home
20 Amberwood Dr, Winchester, MA 01890
Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceili...
Listed by Sino-US Realty Team of Keller Williams Realty

$699,900
Condo
7 Conant Rd #20, Winchester, MA 01890
Beautifully renovated first-floor condo in the highly sought-after "Willows at Winchester" complex. This expansive, sing...
Listed by Brian Woods of Woods Properties Inc.

$1,599,000
Single Family Home
189 Mystic Valley Pkwy, Winchester, MA 01890
Great price improvement - Ready to go at this price! Nestled in the heart of downtown Winchester, the stunning Barstow H...
Listed by Anne Spry of Barrett Sotheby's International Realty