Seller's Agent in 2026
Jayson Kemp
Five Stars Realty
(860) 306-0010
2 in this area
115 Total Sales
Welcome to 41 Chestnut Drive, a charming and well-maintained Cape Cod style home nestled in a quiet Windsor neighborhood, perfect for those seeking comfort, convenience, and classic New England character. This bright and inviting residence has 2 spacious bedrooms with an extra room for either a den or an office, 2 full baths with one being totally renovated, with a flexible floor plan that blends functionality and warmth. A spacious kitchen with ample cabinetry flows easily into the dining area, making meal preparation and gatherings seamless. Hardwood floors add timeless appeal, while thoughtful updates ensure modern comfort. Upstairs bedrooms provide privacy and flexibility for family, guests, or a home office. The home sits on a generous, level 0.55-acre lot with a beautifully landscaped yard-ideal for outdoor activities, gardening, or relaxing on warm afternoons. A private driveway and garage offer plenty of parking and storage. Located just minutes from Windsor Center, schools, shopping, dining, and major highways, this property combines suburban tranquility with easy access to Hartford, Bradley International Airport, and all that the Connecticut River Valley has to offer. Whether you are a first-time owner, downsizing, or simply seeking a welcoming place , 41 Chestnut Drive is a wonderful opportunity to make your next move in Windsor.
Last Agent to Sell the Property
Five Stars Realty Brokerage Phone: (860) 573-0277 License #RES.0821174 Listed on: 11/26/2025
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $255,000 | -- | |
| Quit Claim Deed | -- | None Available | |
| Quit Claim Deed | -- | -- |
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $204,000 | New Conventional | |
| Previous Owner | $20,000 | No Value Available | |
| Previous Owner | $150,000 | No Value Available |
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 02/13/2026 02/13/26 | Sold | $250,000 | -9.1% | $172 / Sq Ft |
| 01/04/2026 01/04/26 | Pending | -- | -- | -- |
| 12/30/2025 12/30/25 | Price Changed | $274,925 | -8.3% | $189 / Sq Ft |
| 12/30/2025 12/30/25 | For Sale | $299,925 | 0.0% | $207 / Sq Ft |
| 12/23/2025 12/23/25 | Pending | -- | -- | -- |
| 12/15/2025 12/15/25 | Price Changed | $299,925 | -4.8% | $207 / Sq Ft |
| 11/26/2025 11/26/25 | For Sale | $314,925 | 0.0% | $217 / Sq Ft |
| 10/07/2016 10/07/16 | Rented | $1,300 | 0.0% | -- |
| 10/07/2016 10/07/16 | Under Contract | -- | -- | -- |
| 10/07/2016 10/07/16 | For Rent | $1,300 | -- | -- |
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $6,190 | $217,560 | $57,960 | $159,600 |
| 2024 | $6,596 | $217,560 | $57,960 | $159,600 |
| 2023 | $4,356 | $129,640 | $40,600 | $89,040 |
| 2022 | $4,313 | $129,640 | $40,600 | $89,040 |
| 2021 | $4,313 | $129,640 | $40,600 | $89,040 |
| 2020 | $4,292 | $129,640 | $40,600 | $89,040 |
| 2019 | $4,198 | $129,640 | $40,600 | $89,040 |
| 2018 | $4,194 | $127,260 | $40,600 | $86,660 |
| 2017 | $4,130 | $127,260 | $40,600 | $86,660 |
| 2016 | $4,011 | $127,260 | $40,600 | $86,660 |
| 2015 | $3,935 | $127,260 | $40,600 | $86,660 |
| 2014 | $3,807 | $124,950 | $40,600 | $84,350 |
Seller's Agent in 2026
Jayson Kemp
Five Stars Realty
(860) 306-0010
2 in this area
115 Total Sales
Seller Co-Listing Agent in 2026
Maria Pirulli
Five Stars Realty
(860) 306-0010
2 in this area
80 Total Sales
Buyer's Agent in 2026
Elvis Methoxha
Country Manor Realty
(860) 302-8187
1 in this area
13 Total Sales
Seller's Agent in 2016
Catherine Thompson
William Raveis/First Town RE
(860) 796-1861
7 in this area
76 Total Sales
Source: SmartMLS
MLS Number: 24142259
APN: WIND-000007-000406-000062
Ask me questions while you tour the home.