147 Properties Available
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$3,200
Condo
17 Irving Street #3, Winchester, MA 01890
Great opportunity to live close to Winchester Center.Available June 1st this 2nd floor unit features a large deck before...
Listed by Robin Griffiths of J. Mulkerin Realty
$499,000
Single Family Home
27 Elm St, Winchester, MA 01890
Attention investors, contractors, and handy owner occupants looking to build sweat equity! This single family home is in...
Listed by Paul Shao of RE/MAX Executive Realty
$3,999,000
Single Family Home
40 Foxcroft Rd, Winchester, MA 01890
An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern lux...
Listed by The Marrocco Group of Coldwell Banker Realty - Lexington
$1,999,000
Single Family Home
1 Saint Augustine Ct, Winchester, MA 01890
Tucked away on a private cul-de-sac shared with just two lucky neighbors, this classic New England Colonial is the total...
Listed by The Pallotta Group of Advisors Living - Winchester
$7,500
Multi-Family, Townhouse
72 Holland #72, Winchester, MA 01890
Welcome to your dream home in the heart of Winchester! This beautifully built 2021 townhouse offers the perfect blend of...
Listed by Team ZNZ of Phoenix Real Estate Partners, LLC
$3,675,000
Single Family Home
80 Arlington Street, Winchester, MA 01890
This stunning Royal Barry Wills colonial estate, with 11 rooms, 5 bedrooms and 3.5 baths, is nestled alongside the 4th g...
Listed by Carolyn Vernaglia of Better Homes and Gardens Real Estate - The Shanahan Group
$1,249,900
Condo
63 Church Street #63, Winchester, MA 01890
Back Bay meets Winchester in this victorian style attached residence in a premier Flats/ downtown location. This lovingl...
Listed by Nancy Ciampa McLaughlin of Redfin Corp.
$4,300
Condo
83 Church #9, Winchester, MA 01890
Much sought after location! Sun filled, 2 bed, 2.5 bath condo in the former Wyman School. This lovely slate roofed, bric...
Listed by Diane Plunkett of Plunkett Properties
$2,600,000
Single Family Home
34 Swan Road, Winchester, MA 01890
Situated in the prestigious Myopia Hill neighborhood, this exceptional sprawling ranch offers a rare combination of time...
Listed by Laurie Cappuccio of Classified Realty Group
$299,000
Condo
200 Swanton St #T4, Winchester, MA 01890
Immaculate, recently renovated Jumbo Studio Condominium with a private/direct-entry terrace level. This unit is spacious...
Listed by Michael Masci of North Atlantic Realty Group
$3,600
Multi-Family, Townhouse
171 Swaton St #16, Winchester, MA 01890
Sunny and Bright Townhouse in a Desirable Location! This well-maintained townhouse offers comfortable living across two ...
Listed by Wei Wang of WW Real Estate LLC
$2,800
Condo
13 Oak Street #1, Winchester, MA 01890
1ST FLOOR! REMODELED 2 Bedroom apartment in 2 family boasts beautifully restored hardwood floors, high celings and great...
Listed by Chuha & Scouten Team of Leading Edge Real Estate
$3,000
Multi-Family, Townhouse
11 Bradford #11, Winchester, MA 01890
Bright & Sunny 3 bedroom, 1.5 bathroom, hardwood floor throughout townhome with 3 level living. it features living room,...
Listed by Wei Wang of WW Real Estate LLC
$4,300
Multi-Family, Townhouse
67 Church #67, Winchester, MA 01890
Enjoy this beautiful renovated home right outside Winchester center! Direct entry unit completely updated all new with g...
Listed by Kim Covino & Co. Team of Compass
$1,849,000
Single Family Home
15 Kendall Street, Winchester, MA 01890
Explore this pristine newer construction, freshly updated home just outside the center!! Situated on a gorgeous level lo...
Listed by Kim Covino & Co. Team of Compass
$1,399,000
Single Family Home
117 Mount Vernon Street, Winchester, MA 01890
Available for the first time in over four decades and nestled just footsteps from Winchester Center, welcome to 117 Moun...
Listed by Vita Realty Group of Compass
$1,379,000
Single Family Home
26 Ridge St, Winchester, MA 01890
Set on a generous, beautifully landscaped lot, this meticulously maintained home showcases numerous recent upgrades, and...
Listed by Dream Team of Dreamega International Realty LLC
$2,250,000
Single Family Home
17 Harrison Street, Winchester, MA 01890
Classic architecture meets modern luxury in this Royal Barry Wills Colonial on an oversized lot in Winchester's beautifu...
Listed by Paula R. Sughrue of Better Homes and Gardens Real Estate - The Shanahan Group
$2,999,999
Single Family Home
Lot 3 Abby Road, Winchester, MA 01890
Welcome to your dream home! This brand-new, meticulously crafted residence offers the perfect blend of luxury & comfort ...
Listed by Vita Realty Group of Compass
$749,900
Single Family Home
235 Cross Street, Winchester, MA 01890
Lovingly cared for by its original owners for nearly 70 years, this charming ranch-style home rests proudly on a desirab...
Listed by Melanie Lentini of Leading Edge Real Estate
$1,650
Condo
200 Swanton #502, Winchester, MA 01890
This rental is SHORT TERM and comes fully furnished. Sparkling, recently renovated studio with amazing views of a beauti...
Listed by Susan Murie of Aikenhead Real Estate, Inc.
$3,600
Multi-Family, Townhouse
38 Florence Street #38, Winchester, MA 01890
3-Bed / 2 Full-bath apartment in a desirable Winchester neighborhood for rent. Situated at a quiet street, this three-be...
Listed by WINN Rental Team of WINN Real Estate & Consulting
$4,950
Single Family Home
137 Ridge St, Winchester, MA 01890
Available 5/1/25! Set in one of Greater Boston's most sought-after communities, this oversized 5-bed, 2-bath Cape offers...
Listed by The Elle Group of Berkshire Hathaway HomeServices Commonwealth Real Estate
$1,199,000
Single Family Home
44 Forest Street, Winchester, MA 01890
This charming home is move-in ready with many updates throughout, situated on a large fenced in level lot close to parks...
Listed by Kim Covino & Co. Team of Compass