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21 Jack Henry Drive

Windham, Connecticut 06280

ACTIVE - NEW$464,997
Beds
3
Baths
2 | 1
SqFt
1,472
Acres
2.40
Year Built
2011
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage

About This Home

Welcome to this beautiful Colonial home, offering the perfect blend of classic charm, comfort, and space. Step inside to find gleaming hardwood floors and generously sized living areas filled with warmth and character. Spacious bedrooms provide plenty of room to relax and unwind, while the expansive living spaces offer a versatile layout ideal for both everyday living and entertaining. At the heart of the home is a beautiful, inviting kitchen featuring ample cabinetry, generous counter space, and plenty of room for gathering and entertaining. Whether preparing everyday meals or hosting family and friends, this welcoming space flows seamlessly with the rest of the home. Situated on an impressive lot of over two acres, the property offers exceptional privacy and an abundance of outdoor space to enjoy. Whether hosting summer gatherings, creating your own backyard retreat, or simply enjoying the peaceful surroundings, this expansive property provides endless possibilities. With its spacious interior, beautiful hardwood floors, inviting kitchen, and private setting, this Colonial is a wonderful place to call home.

Key Facts

City/Town
Windham
Neighborhood
South Windham
Property / Style
Single Family · Colonial
Year Built
2011
Days on Market
0 days
Beds
3
Baths
2 full · 1 half
Living Area
1,472 sq ft
Lot Size
2.40 acres
Garage / Parking
2 garage
Property Taxes
$6,509 / Annually

Market Snapshot

The Windham Market

Single Family · trailing 12 months

Median Days on Market

25

20 active listings

Median $ / Sq Ft

$182

20 active listings

Sale-to-List Ratio

101.4%

166 sales

How this home compares

List Price

$464,997

vs $309,950 median

50.0% above median

Price / Sq Ft

$316

vs $182 median

73.6% above median

Days on Market

0 days

vs 25 days median

25 days fresher than median

Based on 20 active and 166 closed sales (trailing 12 mo) of single family in Windham. Source: SmartMLS · As of September 18, 2026.

Location

21 Jack Henry Drive, Windham, Connecticut

Property + 6 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,159

per month

  • Principal & Interest$2,462
  • Property Taxes$542
  • Insurance$155
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Windham
Neighborhood
South Windham
County
Windham

Residence

Property Type
Single Family
Style
Colonial
Year Built
2011
New Construction
No/Resale
Living Area
1,472 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
None
Appliances
Electric RangeMicrowaveRefrigeratorDishwasher
Basement
FullUnfinished
Interior Features
Open Floor Plan

Exterior & Lot

Lot Size
2.40 acres
Zoning
R1
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Underground UtilitiesSidewalkDeckGutters
Lot Description
Lightly WoodedLevel Lot

Listing & Financials

Property Taxes
$6,509 / Annually
Days on Market
0
MLS #
24207870
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Terence Dominick

(860) 303-2918

Exceptional Real Estate LLC

Co-Listed By

Samuel Sylvia

Exceptional Real Estate LLC

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/18/2026. 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 9/18/2026 at 5:25 AM UTC.