$1,990,000
- 4 Beds
- 4.5 Baths
- 4,474 Sq Ft
4 Chestnut St, Winchester, MA 01890

Tyson Lynch
The Proper Nest Real Estate
(781) 633-6582
$1,990,000
4 Chestnut St, Winchester, MA 01890
Tyson Lynch
The Proper Nest Real Estate
(781) 633-6582
$2,750,000 Open Sun 1PM - 3PM
382 S Border Rd, Winchester, MA 01890
Lucille Murray Advisors Living - Winchester
$2,299,900 Open Sun 11AM - 12:30PM
5 Bacon St, Winchester, MA 01890
Anne Spry Barrett Sotheby's International Realty
$3,599,000 Open Sun 1:30PM - 2:30PM
26 Swan Rd, Winchester, MA 01890
Kim Covino Compass
$2,350,000
276 High St, Winchester, MA 01890
Kim Covino Compass
$2,239,000 Open Sun 1PM - 3PM
61 Grove St, Winchester, MA 01890
Dorothea Feffer Coldwell Banker Realty - Lexington
$2,499,000
14 Grant Rd, Winchester, MA 01890
Monte Marrocco Coldwell Banker Realty - Lexington
$2,399,000 Open Sun 12PM - 1PM
6 Ivy Cir, Winchester, MA 01890
Monte Marrocco Coldwell Banker Realty - Lexington
$2,499,000 Open Sun 11:30AM - 12:30PM
107 Cambridge St, Winchester, MA 01890
Maija Sawyer Puleo William Raveis R.E. & Home Services
$3,599,000
5 Stratford Rd, Winchester, MA 01890
Kim Covino Compass
$2,899,000 Open Sun 2PM - 3PM
10 Sheffield Rd, Winchester, MA 01890
Andersen Group Realty Keller Williams Realty Boston Northwest
$2,349,900
17 Wagon Wheel Rd, Winchester, MA 01890
Yifei Wang Dreamega International Realty LLC
$3,249,000 Open Sun 1:30PM - 2:30PM
44 Cabot St, Winchester, MA 01890
Andersen Group Realty Keller Williams Realty Boston Northwest
$2,299,000
5 Azalea Rd, Winchester, MA 01890
Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate
$2,550,000
19 Laurel Hill Ln, Winchester, MA 01890
Mark Donnellan Advisors Living - Winchester
$2,499,000 Open Sun 12PM - 1:30PM
89 Wildwood St, Winchester, MA 01890
Monte Marrocco Coldwell Banker Realty - Lexington
$1,275,000 Open Sun 11:30AM - 1PM
162 Swanton St Unit 162, Winchester, MA 01890
Kim Covino Compass
$1,999,000 Open Sun 2PM - 4PM
2 Lagrange St, Winchester, MA 01890
Alison Lules-Cuccio Don Baker Real Estate
$1,599,000 Open Sun 11:30AM - 1PM
17 Dennett Rd, Winchester, MA 01890
Kim Covino Compass
$1,890,000
166 Forest St, Winchester, MA 01890
Ning Sun United Real Estate, LLC
$1,688,888
10 Blossom Hill Rd, Winchester, MA 01890
Stephen DeConto Cameron Real Estate Group
$1,250,000
162 Forest St, Winchester, MA 01890
Paul Cirignano The Synergy Group
$1,650,000 Open Sun 12:30PM - 2PM
5 Thornton Rd, Winchester, MA 01890
Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group
$1,899,000 Open Sun 1:30PM - 2:30PM
20 Grove Place, Winchester, MA 01890
Andersen Group Realty Keller Williams Realty Boston Northwest
$1,900,000
4 Aricia Ln, Winchester, MA 01890
The McLaren D'Agostino Team Compass
$2,195,000
58 Bacon St, Winchester, MA 01890
Real Estate Advisors Group Coldwell Banker Realty - Belmont
$3,750,000
9 Lakeview Terrace, Winchester, MA 01890
Kim Covino Compass
$1,349,900 Open Sun 11:30AM - 1PM
35 Harvard St, Winchester, MA 01890
Joanne Mulkerin J. Mulkerin Realty
$3,475,000 Open Sun 12:30PM - 2PM
80 Arlington St, Winchester, MA 01890
Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group
$2,975,000 Open Sun 11:30AM - 12:30PM
54 Wedgemere Ave, Winchester, MA 01890
Kim Covino Compass
$1,299,000 Open Sun 11AM - 12PM
147 Highland Ave, Winchester, MA 01890
Kim Covino Compass
$1,399,900 Open Sun 12PM - 1PM
7 Thornberry Rd, Winchester, MA 01890
salim chowdhury TAJ Mahal Realty LLC
$3,799,900
11 Viking Rd, Winchester, MA 01890
The McLaren D'Agostino Team Compass
$3,598,000
20 Amberwood Dr, Winchester, MA 01890
Dan Li Keller Williams Realty
$3,699,000
54 Johnson Rd, Winchester, MA 01890
Kim Covino Compass
$3,999,000 Open Sun 11AM - 12:30PM
40 Foxcroft Rd, Winchester, MA 01890
Monte Marrocco Coldwell Banker Realty - Lexington
$2,899,000 New Construction
11 Taft Dr, Winchester, MA 01890
Monte Marrocco Coldwell Banker Realty - Lexington
$1,439,900 Open Sun 12PM - 1:30PM
32 Henry St, Arlington, MA 02474
Acone & Company Team Darwin Associates
Winchester, MA, a peaceful Greater Boston suburb, has evolved from a rural farming community to a primarily residential town with a population of nearly 23,000. Located 8 miles north of Boston, Winchester is known for its grand New England homes, ranging from historic Colonial Revivals to modern Cape Cods and ranch styles. The town boasts one of the best school districts in the state, with Winchester Public Schools serving over 4,300 students and receiving high ratings. The private Acera School also offers quality education. Outdoor enthusiasts can enjoy Mystic Lakes State Park, Middlesex Fells Reservation, and the Tri-Community Greenway, which connects Winchester with Woburn and Stoneham. The town's downtown area, bordered by Wedge and Mill Ponds, features a variety of markets, restaurants, boutiques, and service shops. Community events such as Winchester Town Day, PRIDEFest, and summer concerts at Town Common foster a strong sense of community. Wright-Locke Farm, a 383-year-old sustainable conservancy, provides fresh organic produce and nature-based activities. Winchester is accessible via U.S. Route 3 and Interstates 93 and 95, with public transit options including the MBTA bus and commuter rail. Logan International Airport is about 11 miles away. The town has a lower crime risk compared to the national average, with recent data indicating a decrease in violent crimes.
On average, homes in Winchester, MA sell after 28 days on the market compared to the national average of 70 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,300,000, down 5% from the median home sale price over the previous 12 months.
In Winchester, there are currently 38 houses for sale, offering an array of options for potential buyers. With houses priced between $1,250,000 to $3,999,000, there's a range to accomodate every budget. As of August, 2025 the median home price in Winchester is $1,458,000, while the average sale price is $1,357,500, offering insights into the local housing market. On average, houses spend 28 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Winchester, MA and find the perfect place to call home.