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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)

$7,000
Multi-Family, Townhouse
40 Church #A, Winchester, MA 01890
ONE OF A KIND 4 bed, 3.5 baths, luxury townhouse in the heart of Winchester Center! Don't miss out on this home with bot...
Listed by Sarkis James Kavlakian of Real Estate by Hughes & Assoc. Inc.

$2,850,000
Single Family Home
22 Standish Lane, Winchester, MA 01890
This distinguished residence, built by premier local developer, represents the pinnacle of elegant living! Soaring ~9' c...
Listed by Michaela Pixie Mahtani of Leading Edge Real Estate

$2,900,000
Single Family Home
45 Brooks Street, Winchester, MA 01890
Sprawling expanded cape set on stunning private 1/2 acre lot in coveted Brooks neighborhood! The curb appeal alone will ...
Listed by Kim Covino & Co. Team of Compass

$2,749,000
Single Family Home
35 Lawson Road, Winchester, MA 01890
Welcome 35 Lawson where elegance meets modern luxury in this exquisite 6-bedroom 4F, 2H bathroom residence. A stunning m...
Listed by Kim Covino & Co. Team of Compass

$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

$1,324,000
Single Family Home
24 Eugene Drive, Winchester, MA 01890
Welcome home to this architect designed 3 plus bedroom, four bath custom cape! Spacious rooms within a contemporary layo...
Listed by Andrea O'Reilly of Keller Williams Realty Evolution

$655,000
Condo
15 Charles Rd #15, Winchester, MA 01890
Rarely available 2 bedrooms 2 bathrooms townhouse at The Residences in Winchester! Here is your chance to move into a wo...
Listed by Beiping Zhao of Jack Gately Real Estate, LLC

$2,499,000
Single Family Home
31 Lawson Rd, Winchester, MA 01890
Welcome to this gracious Colonial, seamlessly blending traditional charm with modern amenities, perfect for today's life...
Listed by The Marrocco Group of Coldwell Banker Realty - Lexington

$3,350,000
Single Family Home
21 Sheffield West, Winchester, MA 01890
Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the t...
Listed by Kim Covino & Co. Team of Compass

$1,595,000
Condo
7 Wainwright Rd #8, Winchester, MA 01890
Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first lev...
Listed by Nannette Shanahan of Better Homes and Gardens Real Estate - The Shanahan Group

$1,099,000
Condo
160 Swanton Street #160, Winchester, MA 01890
Welcome to 160 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

$2,850,000
Single Family Home
8 Tanglewood Lane, Winchester, MA 01890
This expansive contemporary residence exudes elegance & sophistication and offers the perfect layout for gatherings & ev...
Listed by Kim Covino & Co. Team of Compass

$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

$2,695,000
Single Family Home
18 Middlesex St, Winchester, MA 01890
This European-inspired estate is a masterpiece of design and craftsmanship. Every detail has been meticulously curated, ...
Listed by Candice Macoul of Luxury Living Real Estate

$8,500
Single Family Home
54 Spruce #1, Winchester, MA 01890
Walk to town location. Bright and spacious 10 room, 5 bedroom, 3.5 bath home! Large family room with Brazilian cherry...
Listed by Julia Marino of Archambault Real Estate

$1,529,000
Single Family Home
24 Water St, Winchester, MA 01890
Discover the warmth and charm of this inviting New England Colonial, newly built in 2004. This sun-filled home features ...
Listed by Domingo Medina of Coldwell Banker Realty - Lexington

$695,000
Condo
21 Shepard Court #21, Winchester, MA 01890
Welcome to 21 Shepard Court, a beautifully renovated townhouse nestled in a quiet cul-de-sac. This 2+ bedroom, 1-bathro...
Listed by Abraham Guillen of Encore Realty

$1,199,900
Single Family Home
36 Lebanon Street, Winchester, MA 01890
Nicely updated home in desirable Muraco district! This home has been meticulously maintained & features many recent upda...
Listed by Kim Covino & Co. Team of Compass

$3,199,000
Single Family Home
51 Wedgemere Avenue, Winchester, MA 01890
Discover the perfect blend of charm & modern elegance in this beautiful home, nestled on one of the most highly desired ...
Listed by Kim Covino & Co. Team of Compass

$1,745,000
Single Family Home
85 Thornberry Rd, Winchester, MA 01890
Welcome to the highly-coveted Westside of Winchester, MA. This meticulously maintained Colonial-style home is set on 20,...
Listed by Diane Basemera of Coldwell Banker Realty - Newton

$8,000
Single Family Home
271 Washington #1, Winchester, MA 01890
Walk to town and schools from this spacious 11 room, 5 bedroom, 3.5 bath home! Open floor plan and high ceilings. Bonus ...
Listed by Julia Marino of Archambault Real Estate

$2,499,000
Single Family Home
50 Winford Way, Winchester, MA 01890
Just completed!! New construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime ...
Listed by Kim Covino & Co. Team of Compass