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281 Deerfield Road

Windsor, Connecticut 06095

ACTIVE - NEW$250,000
Beds
3
Baths
1 | 1
SqFt
1,075
Acres
0.22
Year Built
1952
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,840

per 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

Similar Properties

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Listed By

Maxwell Castrogiovanni

(860) 302-8394

eXp Realty

(866) 828-3951

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.