PENDING
$40K PRICE DROP
41 Chestnut Dr Windsor, CT 06095
West Windsor NeighborhoodEstimated payment $1,953/month
Total Views
95,748
2
Beds
2
Baths
1,452
Sq Ft
$189
Price per Sq Ft
Highlights
- Cape Cod Architecture
- Attic
- Bonus Room
- Poquonock Elementary School Rated A
- 1 Fireplace
- Mud Room
About This Home
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.
Listing Agent
Five Stars Realty Brokerage Phone: (860) 573-0277 License #RES.0821174 Listed on: 11/26/2025
Co-Listing Agent
Five Stars Realty Brokerage Phone: (860) 573-0277 License #RES.0828984
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $6,190
Year Built
- Built in 1955
Lot Details
- 0.55 Acre Lot
- Level Lot
- Property is zoned Per town
Home Design
- Cape Cod Architecture
- Brick Exterior Construction
- Concrete Foundation
- Asphalt Shingled Roof
- Masonry Siding
Interior Spaces
- 1,452 Sq Ft Home
- 1 Fireplace
- Mud Room
- Bonus Room
- Partially Finished Basement
- Basement Fills Entire Space Under The House
- Pull Down Stairs to Attic
Kitchen
- Electric Range
- Dishwasher
Bedrooms and Bathrooms
- 2 Bedrooms
- 2 Full Bathrooms
Laundry
- Laundry on lower level
- Dryer
- Washer
Parking
- 2 Car Garage
- Private Driveway
Location
- Property is near shops and bus stop
Utilities
- Central Air
- Hot Water Heating System
- Heating System Uses Oil
- Private Company Owned Well
- Hot Water Circulator
- Electric Water Heater
- Fuel Tank Located in Basement
Listing and Financial Details
- Assessor Parcel Number 770616
Map
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Home Values in the Area
Average Home Value in this Area
Tax History
| 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 |
Source: Public Records
Property History
| Date | Event | Price | List to Sale | Price per 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 | -- | -- |
Source: SmartMLS
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Quit Claim Deed | -- | None Available | |
| Quit Claim Deed | -- | -- |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $20,000 | No Value Available | |
| Previous Owner | $150,000 | No Value Available |
Source: Public Records
About the Listing Agent
I'm an expert real estate agent with Five stars realty Hartford CT and the nearby area, providing home-buyers and sellers with professional, responsive and attentive real estate services. Want an agent who'll really listen to what you want in a home? Need an agent who knows how to effectively market your home so it sells? Give me a call! I'm eager to help and would love to talk to you.
Jason's Other Listings
Source: SmartMLS
MLS Number: 24142259
APN: WIND-000007-000406-000062
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