20 Properties Available
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$999,000
Multi-Family
339-341 Washington Street, Winchester, MA 01890
Exceptional opportunity for investors, owner-occupants, or multigenerational living in this two-family home conveniently...
Listed by The Pallotta Group of Gibson Sotheby's International Realty
$2,399,000
Single Family Home
53 Winford Way, Winchester, MA 01890
Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with ev...
Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest
$1,199,000
Single Family Home
53 Lake Street, Winchester, MA 01890
Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Win...
Listed by Kim Covino & Co. Team of Compass
$1,199,000
Condo
129 Washington St #129, Winchester, MA 01890
Prime Winchester location just moments from Winchester Center, within walking distance to elementary, middle, high schoo...
Listed by The Mary Scimemi Team of Leading Edge Real Estate
$3,149,000
Single Family Home
8 Priscilla Ln, Winchester, MA 01890
Truly one of a kind new construction blending timeless design with modern luxury, 8 Priscilla Ln offers 6,500± sq ft of ...
Listed by The Pezzano Group of Rise Signature Homes
$699,000
Single Family Home
23 Shepard Ct #U23, Winchester, MA 01890
Huge Price Drop – Best Value in the Winchester School District! Beautifully maintained townhouse-style condex offering 3...
Listed by Nancy Zhang Zhenning of Fairview Partners International LLC
$699,900
Single Family Home
23 Shepard Ct #U23, Winchester, MA 01890
Huge Price Drop – Best Value in the Winchester School District! Beautifully maintained townhouse-style condex offering 3...
Listed by Nancy Zhang Zhenning of Fairview Partners International LLC
$1,499,000
Multi-Family
7-9 Ridge St, Winchester, MA 01890
Beautiful 2 family-duplex nestled in Winchester's desirable West Side. It tells the story of a home that has been treasu...
Listed by The Synergy Group of The Synergy Group
$5,200
Multi-Family, Townhouse
48 Spruce #1, Winchester, MA 01890
Spacious 4-bedroom, 3.5-bath townhouse ideally located within walking distance to the town center, schools, and commuter...
Listed by Dylan Archambault of Archambault Real Estate
$4,200
Multi-Family, Townhouse
67 Church #67, Winchester, MA 01890
DOWNTOWN WINCHESTER! Enjoy this beautiful recently renovated home right outside Winchester center! Direct entry 2 bedroo...
Listed by Kim Covino & Co. Team of Compass
$3,800
Multi-Family, Townhouse
63 Holland St #63, Winchester, MA 01890
Welcome to 63 Holland St in Winchester! This beautifully renovated 2-bedroom, 1-bath townhome offers the perfect blend o...
Listed by Issam Dib of Skyline Realty
$2,450,000
Single Family Home
50 Brooks Street, Winchester, MA 01890
Discover this picture perfect 4 BD 3.5 BA colonial in coveted Brooks neighborhood! This distinguished property offers a ...
Listed by Kim Covino & Co. Team of Compass
$5,000
Single Family Home
17 Russell Rd, Winchester, MA 01890
Move in date: 6/15/2025. Tenant pays all utilities (gas, heat, electricity, cold/hot water and trash disposal). Lead Pai...
Listed by Tsz Mui Kwan of Kwan Realty Inc.
$11,000
Single Family Home
34 Glen Road, Winchester, MA 01890
TOP location! Beautifully renovated single family colonial in Ambrose elementary district, situated on a gorgeous lot wi...
Listed by Kim Covino & Co. Team of Compass
$3,475,000
Single Family Home
2 Everett Ave, Winchester, MA 01890
Welcome to one of Winchester's most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits o...
Listed by Joan Francis Sullivan of Better Homes and Gardens Real Estate - The Shanahan Group
$3,200,000
Single Family Home
9 Albamont Road, Winchester, MA 01890
Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcra...
Listed by Kim Covino & Co. Team of Compass
$2,800
Condo
200 Swanton Street #T35, Winchester, MA 01890
SPRING TIME IS COMING! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering...
Listed by Nuri Tirana of Tirana Real Estate Group
$6,000
Single Family Home
31 Fells Road, Winchester, MA 01890
Available SHORT TERM rental through October 2025 with flexible lease options. Prime location on desirable Fells Road wit...
Listed by Kim Covino & Co. Team of Compass
$3,900
Condo
10-12 Webster St #1, Winchester, MA 01890
Amazing 4 bed 2 bath available 2/1/26 located within close proximity of Winchester Center! This spacious apartment takes...
Listed by Ryan Kelly of Real Broker MA, LLC
$1
Commercial
10-12 Park Street, Winchester, MA 01890
Winchester Center. 3,500+ s/f of amazing flex space. Two levels with an open floor plan, loft space offices, break room,...
Listed by Mike Brasco of Century 21 Shawmut Properties
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