281 Deerfield Road
Windsor, Connecticut 06095
- Beds
- 3
- Baths
- 1 | 1
- SqFt
- 1,075
- Acres
- 0.22
- Year Built
- 1952
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to 281 Deerfield Road, a charming Cape Cod-style home in Windsor that's full of character and just waiting for its next owner's personal touch! With its classic exterior, inviting layout, and plenty of opportunity to make it your own, this home offers a wonderful canvas for bringing your ideas to life. Step inside to find hardwood flooring throughout much of the home, adding warmth and character to the living spaces. The living room features a cozy fireplace that serves as a natural focal point, while the separate dining room provides a welcoming space for gathering around the table. The generously sized kitchen offers plenty of room to work with and the opportunity to create something truly special. With 3 bedrooms and 1.5 bathrooms, the home offers a flexible layout that includes two bedrooms on the main level, making everyday living convenient while leaving additional space upstairs. The unfinished basement is another area full of untapped potential, whether you envision additional storage, a workshop, or the possibility of creating more usable space down the road. New mechanicals add an important update to the home, allowing the next owner to focus on making the cosmetic improvements that reflect their own style. Outside, the cleared, level, and fenced-in backyard offers a great setting for relaxing, gardening, entertaining, or simply enjoying the outdoors.
Key Facts
- City/Town
- Windsor
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1952
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 1 full · 1 half
- Living Area
- 1,075 sq ft
- Lot Size
- 0.22 acres
- Garage / Parking
- 3 total
- Property Taxes
- $4,460 / Annually
Market Snapshot
The Windsor Market
Single Family · trailing 12 months
Active Listings
37
31 under contract
Median List Price
$398,000
37 active listings
Median Closed Price
$389,900
242 sales
Median Days on Market
47
37 active listings
Median $ / Sq Ft
$224
37 active listings
Sale-to-List Ratio
102.9%
242 sales
How this home compares
List Price
$250,000
vs $398,000 median
37.2% below median
Price / Sq Ft
$233
vs $224 median
In line with median
Days on Market
0 days
vs 47 days median
47 days fresher than median
Based on 37 active and 242 closed sales (trailing 12 mo) of single family in Windsor. Source: SmartMLS · As of October 19, 2026.
Location
281 Deerfield Road, Windsor, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per month
- Principal & Interest$1,385
- Property Taxes$372
- Insurance$83
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Windsor
- Neighborhood
- N/A
- County
- Hartford
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1952
- New Construction
- No/Resale
- Living Area
- 1,075 sq ft
Schools
- Elementary
- John F. Kennedy
- High
- Windsor
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Window Unit
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Electric CooktopElectric RangeRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinishedStorageInterior AccessConcrete FloorFull With Hatchway
- In-Law Apartment
- No
- Interior Features
- Cable - Available
Exterior & Lot
- Lot Size
- 0.22 acres
- Zoning
- R11
- Garage / Parking
- 3 total parking spacesPavedOff Street ParkingDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Aluminum
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- SidewalkGutters
- Lot Description
- Fence - FullLevel LotCleared
Listing & Financials
- Property Taxes
- $4,460 / Annually
- Days on Market
- 0
- MLS #
- 24214034
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/19/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 10/19/2026 at 5:20 PM UTC.