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

$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

$2,695,000
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

$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

$3,989,000
Single Family Home
26 Swan Road, Winchester, MA 01890
Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offe...
Listed by Kim Covino & Co. Team of Compass

$3,250
Condo
115 Washington Street #2B, Winchester, MA 01890
Stunning unit in the heart of Winchester with easy access to Boston and the surroundings. Conveniently located near com...
Listed by Vijoy Abraham of Abraham Realty

$2,999,000
Single Family Home
8 Chestnut St, Winchester, MA 01890
Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and ...
Listed by The McLaren Team of Compass

$4,500
Single Family Home
17 Russell Rd, Winchester, MA 01890
Single-family home with 3 bedrooms and 1.5 baths. Move in date: 6/1/2025. Tenant pays all utilities (gas, heat, electric...
Listed by Tsz Mui Kwan of Kwan Realty Inc.

$3,699,000
Single Family Home
54 Johnson Road, Winchester, MA 01890
This newly constructed home faces Old Village Dr. & redefines modern luxury! Designed w/ both elegance & everyday comfor...
Listed by Kim Covino & Co. Team of Compass

$3,499,000
Single Family Home
4 Norwood St, Winchester, MA 01890
Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town ...
Listed by Mark Donnellan of Advisors Living - Winchester

$2,200
Condo
200 Swanton St #428, Winchester, MA 01890
Bright and sunny 1 bedroom and 1 bathroom condo in Winchester Park View. close to shopping, restaurants, town Center and...
Listed by Wei Wang of WW Real Estate LLC

$11,000
Single Family Home
52 North Border Rd., Winchester, MA 01890
Grand and masterfully crafted home on this private road abutting 2200 acre Fells conservation land. This spacious home h...
Listed by Julia Marino of Archambault Real Estate

$5,000
Single Family Home
27 Ledyard Road #SF, Winchester, MA 01890
SHORT TERM RENTAL - Oversized cape with hardwood floors throughout. Large front to back living room with working fire...
Listed by Diane Plunkett of Plunkett Properties

$2,500
Condo
253 Swanton Street #Rear, Winchester, MA 01890
Enjoy this beautifully renovated 1 bedroom, 1.5 bathroom comfortable living area only minutes away from downtown Winches...
Listed by Rachel Ventresca of Greater Metropolitan R. E.

$15,000
Single Family Home
186 Ridge Street, Winchester, MA 01890
Fully furnished beautiful new construction home located on the West Side of Town and proudly situated on over an acre lo...
Listed by Anzor Sidamonidze of Skylight Real Estate, LLC

$1
Commercial
7 Mckay Ave, Winchester, MA 01890
Call List Agent
Listed by Danny Cruz of The Stubblebine Company

$900
Commercial
72 Swanton Street #Rear, Winchester, MA 01890
Available April 1st------OPEN FLOOR PLAN OFFICE/RETAIL/Commercial/Flex space available for lease in Winchester, locate...
Listed by John E. Magazzu of RE/MAX Renaissance Inc.

$2,800
Commercial
143 Swanton Street, Winchester, MA 01890
Rare opportunity to rent this Prime, Highly visible office/retail space available for April 1st! Beautiful, Sunny and sp...
Listed by Rachel Ventresca of Greater Metropolitan R. E.