$329,925
- 2 Beds
- 2 Baths
- 1,452 Sq Ft
41 Chestnut Dr, Windsor, CT 06095

Jason Kemp
Five Stars Realty
(860) 981-0837
$329,925
41 Chestnut Dr, Windsor, CT 06095
Jason Kemp
Five Stars Realty
(860) 981-0837
$259,900
99 Pepperbush Way, Windsor, CT 06095
Amy Rio
Executive Real Estate Inc.
(860) 300-2726
$449,900
680 Kennedy Rd, Windsor, CT 06095
Timothy Faucher eXp Realty
$424,900
16 Crabapple Rd, Windsor, CT 06095
John Waters Berkshire Hathaway NE Prop.
$469,900
29 Quail Hollow Dr, Windsor, CT 06095
Michael Zizzamia William Raveis Real Estate
$489,999
9 Meadowlark Dr, Windsor, CT 06095
Maritza Zavala Naples Realty Group, LLC
$390,000
145 Park Ave, Windsor, CT 06095
Dadrie Broderick Coldwell Banker Realty
$420,000
190 Prospect Hill Rd, Windsor, CT 06095
Shannon King Cozy Homes Real Estate
$499,900
10 Cleary Ln, Windsor, CT 06095
Tammy Ferrauola Eagle Eye Realty PLLC
$399,900
28 Sunnyfield Dr, Windsor, CT 06095
Christian Rivas Plata Complete Real Estate
$405,000
119 Joshua Hill, Windsor, CT 06095
Nicole Crenshaw Barile Realty Group
$399,900
1476 Poquonock Ave, Windsor, CT 06095
Kervin Figaro Five Stars Realty
$421,000
957 Palisado Ave, Windsor, CT 06095
Steven Koleno Beycome of Connecticut
$409,000 Open Sat 12PM - 2PM
1492 Poquonock Ave, Windsor, CT 06095
Brielle Browne William Pitt Sotheby's Int'l
$400,000 Open Sun 1PM - 3PM
21 Long Hill Rd, Windsor, CT 06095
Paul Striefler LPT Realty
$334,900
25 Maude Cir, Windsor, CT 06095
Sharon Fox Carl Guild & Associates
$319,900
580 W Wolcott Ave, Windsor, CT 06095
Ola Aly Berkshire Hathaway NE Prop.
$374,900
94 Clubhouse Rd, Windsor, CT 06095
Eden Wimpfheimer Berkshire Hathaway NE Prop.
$309,900
3 Saville St, Windsor, CT 06095
Fabian Weir PrefeQ Realty
$329,900
107 Sunnyfield Dr, Windsor, CT 06095
Ben Castonguay Sentry Real Estate
$359,000
25 Patriot Rd, Windsor, CT 06095
Reza Abbassi New Door Realty
$279,900
20 Sage Park Rd, Windsor, CT 06095
Joe Aloisa Coldwell Banker Realty
$334,900
8 Aramamet St, Windsor, CT 06095
Gregory Wright Great Estates, CT
$370,000
41 Hale Dr, Windsor, CT 06095
Jeffrey Hiser Berkshire Key Realty
$250,000
39 Warham St, Windsor, CT 06095
Mark Mermelstein eXp Realty
$489,000
27 Valley View Dr, Windsor, CT 06095
Andre Holloman KW Legacy Partners
$335,000
175 E Pershing St, Bloomfield, CT 06002
Christian Flores mygoodagent
$574,900
30 Parkwood Dr, Windsor, CT 06095
Kervin Figaro Five Stars Realty
$425,000
16 Hilltop Rd, Windsor, CT 06095
Joe Coelho Coldwell Banker Realty
$344,900
39 Loren Cir, Windsor, CT 06095
Lavasha Bester CENTURY 21 AllPoints Realty
$436,000
58 Amanda Cir, Windsor, CT 06095
Steven Koleno Beycome of Connecticut
$579,900 New Construction
318 Capen St, Windsor, CT 06095
Lori Gabriel Coldwell Banker Realty
$569,900 New Construction
342 Capen St, Windsor, CT 06095
Lori Gabriel Coldwell Banker Realty
$579,900 New Construction
26 Cook Hill Rd, Windsor, CT 06095
Lori Gabriel Coldwell Banker Realty
$499,990 Pre-Foreclosure
1 Deanne Lynn Cir, Windsor, CT 06095
Kostas Travisano Sailpoint Property Group
$325,000 Coming Soon
351 Rainbow Rd, Windsor, CT 06095
Diane Q McHugh Berkshire Hathaway NE Prop.
$300,000 Open Sat 1:30PM - 2:30PM
2 Sandra Dr, Bloomfield, CT 06002
Austin Miglin Realty Negotiations LLC
$990,000
49 Seymour Rd, East Granby, CT 06026
George Agnelli Agnelli Real Estate
Windsor, Connecticut, known for its historical significance as one of the first towns in the state, offers a mix of established and new homes, including Cape Cod, Colonial Revival, and ranch-style designs. The community is conveniently located near major highways like I-91 and I-291, providing easy access to New York and Hartford. Windsor's downtown features diverse dining options such as Dom’s for breakfast, Windsor Asian Bistro for Asian cuisine, and Union Street Tavern, a converted firehouse pub that hosts charity events. Residents enjoy various things to do, including summer concerts at the Town Green and Halloween festivities like Nightmare on Broad Street. Windsor Public Schools are highly rated, with John F. Kennedy School, Sage Park Middle School, Windsor High School, and Oliver Ellsworth School all earning commendable grades. Recreational opportunities abound with the Keney Park Golf Course and Windsor Meadows State Park offering outdoor activities. The city is well-connected with CT Transit bus lines, a local train station, and proximity to Bradley International Airport. Homes in Windsor range from historical properties to contemporary builds, often situated on spacious lots without sidewalks.
On average, homes in Windsor, CT sell after 38 days on the market compared to the national average of 52 days. The median sale price for homes in Windsor, CT over the last 12 months is $355,000, up 4% from the median home sale price over the previous 12 months.
In Windsor, there are currently 38 houses for sale, offering an array of options for potential buyers. With houses priced between $250,000 to $990,000, there's a range to accomodate every budget. As of October, 2025 the median home price in Windsor is $349,950, while the average sale price is $360,274, offering insights into the local housing market. On average, houses spend 38 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 Windsor, CT and find the perfect place to call home.