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.
- MLS# 24139222
- Date Listed11/10/2025
- Days on Realty 2 Days
- Bedrooms 2
- Bathrooms 2 Full baths, 1 Half baths
- Lot Size 0.55 acres (23,958 sq. ft)
- Sewer Septic Tank
- Property Type Single Family
- County Hartford
- Year Built 1955
- Water Well
- Square Feet 1,452 sq. ft
- Price Per Sq. Ft $216.89
Interior Features
- Appliances Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Electric Water Heater
- Cooling Central Air
- Heating Oil, Hot Water
Exterior / Lot Features
- Roof Asphalt
- Lot Size Acres 0.55
- Lot Size SQFT 23,958.00
- Lot Features Level
Directions
GPS friendly
Financial Considerations
- Tax Amount $6,190
- Terms Cash, Conventional, FHA, VA Loan
Nearby Schools
Source: School Digger
Public • PK - 2 • Serves this home
2.62 mi
Distance
Public • 6 - 8 • Serves this home
2.07 mi
Distance
Public • 9 - 12 • Serves this home
2.07 mi
Distance
Public • PK - 2 • Serves this home
2.62 mi
Distance
Public • PK - 2
2.87 mi
Distance
Greater Hartford Academy Of The Arts Elementary Magnet
Public • PK - 5
4.19 mi
Distance
Public • PK - 2
4.41 mi
Distance
Public • PK - 2
6.39 mi
Distance
Public • PK - 2
6.87 mi
Distance
Public • 6 - 8 • Serves this home
2.07 mi
Distance
Public • 3 - 5
4.79 mi
Distance
Public • 3 - 5
4.96 mi
Distance
Academy Of Aerospace And Engineering Middle And High School
Public • 6 - 12
5.18 mi
Distance
Public • 6 - 12
5.58 mi
Distance
Global Experience Magnet School
Public • 6 - 12 • Serves this home
5.58 mi
Distance
Public • 6 - 8
5.59 mi
Distance
Public • 6 - 8
6.66 mi
Distance
Public • 3 - 5
6.66 mi
Distance
Public • 6 - 8
7.43 mi
Distance
Public • 9 - 12 • Serves this home
2.07 mi
Distance
Public • 9 - 12
4.05 mi
Distance
Public • 9 - 12
5.59 mi
Distance
Public • 9 - 12
5.88 mi
Distance
Public • 9 - 12
7.37 mi
Distance
Public • 9 - 12
8.08 mi
Distance
Praise Power & Prayer Christian School
Private • KG - 12
7.1 mi
Distance
Private • PK - 12
7.62 mi
Distance
Private • 09 - 12
7.84 mi
Distance
Private • 09 - 12
7.9 mi
Distance
Private • 09 - 12
8.68 mi
Distance
Sales & Tax History
Source: Public Records
| Street Address | Beds | Baths | Sold Date | List Price | Valuation Date | Valuation Price |
|---|---|---|---|---|---|---|
| 37 West River Road | 3 | 2 | Nov 02, 2025 | $399,900 | Nov 12, 2025 | - |
| 281 Mountain Road | Listing | 3 | 2 | Sep 23, 2025 | $230,000 | Jan 24, 2024 | $290,750 |
| 18 Marshall Phelps Road | 5 | 3 | Oct 07, 2025 | $350,000 | Nov 12, 2025 | - |
| 4 Hazel Street | 4 | 2 | Nov 10, 2025 | $349,900 | Nov 12, 2025 | - |
| 608 Kennedy Road | 4 | 2 | Nov 04, 2025 | $305,000 | Nov 12, 2025 | - |
| 210 Reed Avenue | 3 | 2 | Oct 15, 2025 | $264,900 | Nov 12, 2025 | - |
| 16 Basile Road | 3 | 3 | Oct 15, 2025 | $329,900 | Nov 12, 2025 | - |
| 485 Halfway House Road | 3 | 1 | Oct 15, 2025 | $239,900 | Nov 12, 2025 | - |
| 69 Spring Street | 3 | 2 | Oct 15, 2025 | $247,000 | Nov 12, 2025 | - |
| 59 Poole Road | 3 | 3 | Oct 15, 2025 | $579,900 | Nov 12, 2025 | - |
Population & Environment
Source: Sperling's Best Places
| Zip | City | County | National | |
|---|---|---|---|---|
| Population | 30,213 | 30,218 | 913,900 | 335,858,263 |
| Population Density | 1,046 | 1,024 | 1,243 | 95 |
| People per Household | 2.5 | 2.5 | 2.5 | 2.6 |
| Median Age | 45.8 | 45.8 | 42 | 39.1 |
| Median Income | $91,276 | $91,279 | $77,593 | $66,222 |
| Average Income | $42,546 | $42,559 | $41,527 | $35,475 |
| Cost of Living Index | 107 | 107 | 103 | 100 |
| Zip | City | County | National | |
|---|---|---|---|---|
| January Avg. High Temp | 16.65°F | 16.65°F | 16.3°F | 22.6°F |
| July Avg. High Temp | 84.22°F | 84.22°F | 83.8°F | 86.2°F |
| Annual Precipitation | 45.01" | 45.01" | 56.93" | 38" |
7/100
Car-Dependent
Walk Score ®
23/100
Bikable
Bike Score ®
Overview
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.Walkability averages in the surrounding area
The average walkability score in the surrounding area is Walk Score: 9/100, Transit Score: 0/100, Bike Score: 22/100.
Property Change History
Points of Interest near 41 Chestnut Drive, Windsor, CT 06095
0.2 mi
Distance
0.51 mi
Distance
0.55 mi
Distance
0.55 mi
Distance
0.38 mi
Distance
0.39 mi
Distance
0.55 mi
Distance
0.54 mi
Distance
0.66 mi
Distance
0.26 mi
Distance
0.39 mi
Distance
0.43 mi
Distance
0.48 mi
Distance
0.53 mi
Distance
0.54 mi
Distance
0.57 mi
Distance
0.64 mi
Distance
0.66 mi
Distance
0.67 mi
Distance
0.74 mi
Distance
0.78 mi
Distance
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Frequently Asked Questions for 41 Chestnut Drive
Source: Realty.com
41 Chestnut Drive, Windsor, CT 06095 is a Single Family 1,452 sq. ft. home listed for sale. Realty.com has 27 photos available of this 2 bed, 3 bath house, listed at $314,925. View sales and tax history, use our mortgage calculator and more on Realty.com
Realty.com has 27 photos of 41 Chestnut Drive.
Our records indicate that 41 Chestnut Drive was built in 1955.
The full address for this home is 41 Chestnut Drive, Windsor, CT 06095.
41 Chestnut Drive has been listed on Realty.com since Mon November 10, 2025
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.
The average walkability score in the surrounding area is Walk Score: 9/100, Transit Score: 0/100, Bike Score: 22/100.
There are 3 schools assigned to this home. Check out the schools near 41 Chestnut Drive. Allgrove School (Grades: PK - 2), East Granby Middle School (Grades: 6 - 8), East Granby High School (Grades: 9 - 12)
Listing provided courtesy of:
Five Stars Realty
(tel: 860-560-1500)
Listing agent:
Jayson Kemp
(tel: 860-560-1500)
(#845663)
This content last refreshed on 2025-11-12 11:16:16. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Export listing data of 41 Chestnut Drive, Windsor, CT 06095 : MLS# 24139222