21 Jack Henry Drive
Windham, Connecticut 06280
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 1,472
- Acres
- 2.40
- Year Built
- 2011
- Neighborhood
- South Windham
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
20
24 under contract
Median List Price
$309,950
20 active listings
Median Closed Price
$277,500
166 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per 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
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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.