142 Properties Available
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$2,899,000
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
$3,100
Condo
31 Irving St #1, Winchester, MA 01890
Bright and sunny 1st floor unit is ready to move in. Large sun drenched living with newer hardwood and large windows; mo...
Listed by Yuan Guo of Phoenix Real Estate
$1,050,000
Single Family Home
8 Ware Rd, Winchester, MA 01890
Tucked into the desirable Winchester Highlands and abutting the Middlesex Fells, 8 Ware Road offers space, comfort, and ...
Listed by Alex Navarro of Coldwell Banker Realty - Beverly
$1,199,000
Single Family Home
48 Winford Way, Winchester, MA 01890
Welcome to 48 Winford Way, a three bed, two bath Cape on a lovely level lot with a family room addition and a garage. A ...
Listed by Rebecca Brennan of Better Homes and Gardens Real Estate - The Shanahan Group
$2,299,000
Single Family Home
4 Fairfield Pl, Winchester, MA 01890
Meticulously maintained newer construction colonial located on a quaint 4 home street close to Winchester center! Enjoy ...
Listed by Kim Covino & Co. Team of Compass
$699,900
Condo
7 Conant Rd #23, Winchester, MA 01890
Fantastic opportunity to own a freshly updated 2 bed 2 bath condo in Winchester—one of Massachusetts' top-rated school d...
Listed by Xin Cui of Hooli Homes Boston
$1,525,000
Single Family Home
21 Johnson Rd, Winchester, MA 01890
This lovingly maintained Colonial home is ideally situated just a 1/2 mile from Vinson-Owen Elementary School. Featuring...
Listed by Stefanie Clifford of Keller Williams Realty Boston Northwest
$724,999
Condo
666 Main St #206, Winchester, MA 01890
Welcome to Wedgewood Place at 666 Main Street in Winchester Center - a perfect blend of small-town charm and urban conve...
Listed by Sveta Vakhitova of Berkshire Hathaway HomeServices Warren Residential
$1,199,000
Single Family Home
18 Brookside Avenue, Winchester, MA 01890
Charming, fully renovated colonial in a prime Winchester neighborhood! The sunny front porch welcomes you in, leading to...
Listed by Kim Covino & Co. Team of Compass
$3,295
Multi-Family, Townhouse
50 Lake Street #O, Winchester, MA 01890
LOCATION! LOCATION! LOCATION! Enjoy the tranquil beauty and gorgeous views! Sit on the patio and watch the swans float b...
Listed by Sheri O'Connor of Plunkett Properties
$6,900
Multi-Family, Townhouse
37 Rumford St #37, Winchester, MA 01890
This 4-bed,3.5-bath custom-designed and built in 2012 townhouse feels like a single family. Step onto the welcoming farm...
Listed by Alina Wang Team of Coldwell Banker Realty - Lexington
$2,349,900
Single Family Home
17 Wagon Wheel Road, Winchester, MA 01890
Experience breathtaking Boston skyline views from nearly every room in this exquisitely maintained dream home—your own p...
Listed by Dream Team of Dreamega International Realty LLC
$1,065,000
Single Family Home
25 Canterbury Road, Winchester, MA 01890
Don't miss your opportunity to own on Canterbury Road! This sun-drenched, 4-bedroom home with hardwood flooring offers a...
Listed by Lynne Russo of Better Homes and Gardens Real Estate - The Shanahan Group
$2,199,000
Single Family Home
4 Worthen Road, Winchester, MA 01890
Stunning 5 bed 3.5 bath customized colonial situated on a gorgeous street with 1/2 acre lot! This sun-drenched home is ...
Listed by Kim Covino & Co. Team of Compass
$3,200
Condo
7 Conant Rd #11, Winchester, MA 01890
Available 9/1/2025! Highly Desirable The Willows Condominiums.... Sunny 2 bedrooms and 2.5 bathrooms second floor unit.....
Listed by Yongcheng Wang of Phoenix Real Estate Partners, LLC
$5,200
Multi-Family, Townhouse
42 Spruce #42, Winchester, MA 01890
Walk to town location from this four bedroom, two and one half bath two level townhome. Walk to McCall and WHS. Large ...
Listed by Julia Marino of Archambault Real Estate
$1,499,000
Condo
23 Elmwood Avenue #C, Winchester, MA 01890
Welcome to Elmwood condos with over 2,100 SF of stunning single-level luxury living in vibrant downtown Winchester! This...
Listed by Kim Covino & Co. Team of Compass
$2,550
Multi-Family, Townhouse
279 Cross St #279, Winchester, MA 01890
Wonderful, bright two bedroom townhome in Winchester at an affordable price. Move right in, the previous owner updated t...
Listed by Heejeong Joo of Blue Ocean Realty, LLC
$2,700
Condo
200 Swanton St #205, Winchester, MA 01890
Sunny & Bright 2-Bedroom Condo in Winchester Park View – Available 09/01. Enjoy comfortable living in this updated and s...
Listed by Wei Wang of WW Real Estate LLC
$2,400,000
Single Family Home
12 Olde Lyme Rd, Winchester, MA 01890
*** OPEN HOUSE CANCELLED**** OFFER ACCEPTED Presenting 12 Olde Lyme Rd, where classic Colonial charm meets modern style ...
Listed by Mary Beth McGillicuddy of Engel & Volkers, South Shore
$14,000
Single Family Home
3 Wood Lane, Winchester, MA 01890
Tucked away on a private cul-de-sac near Winchester Country Club, this beautifully furnished 5-bd 5.5-bath Colonial blen...
Listed by Leigh Ventura of Compass
$674,900
Single Family Home
20 Arthur St #20, Winchester, MA 01890
Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See docu...
Listed by Dan O'Connell Sr of LAER Realty Partners
$15,000
Single Family Home
20 Amberwood Dr #0, 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
$2,000
Condo
200 Swanton #L22, Winchester, MA 01890
Enjoy this newly renovated one bedroom one bathroom 1st-floor unit in beautiful Winchester... This open floor plan featu...
Listed by Donna Addezio of Media Realty Group Inc.