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$464,997

  • For Sale
  • Under Contract
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,472 Sq. Ft.
  • 2 Car Garage
  • Updated 1 day ago
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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.

Full Property Details for 21 Jack Henry Dr

General

  • Price: $464,997
  • Taxes: (July 2025-June 2026)
  • Status: Under Contract
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24207870
  • Updated: 10/7/2026
  • Added to Site: 21 day(s) ago

Interior

  • Number of Rooms: 6
  • Interior Features: Open Floor Plan
  • Appliances: Electric Range, Microwave, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Primary Bathroom: Primary Bath - Remod, Upper
  • Full Bath: Remodeled, Tub w/Shower, Tile Floor, Upper
  • Partial Bath: Remodeled, Tile Floor, Lower

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Remodeled, Hardwood Floor, Upper
  • Bedroom 1: Bedroom - Remodeled, Hardwood Floor, Upper
  • Bedroom 2: Bedroom - Remodeled, Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Remodeled, Hardwood Floor, Main
  • Kitchen: Kitchen - Remodeled, Quartz Counters, Hardwood Floor, Main
  • Dining Room: Dining Room - Remodeled, Hardwood Floor, Main

Exterior

  • Exterior Features: Underground Utilities, Sidewalk, Deck, Gutters

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Windham
  • Neighborhood: South Windham
  • Driving Directions: GPS FRIENDLY

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Community

  • Community Name: South Windham
  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Property Management

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Unfinished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 1,472
  • Above Ground: 1,472 Sq. Ft.
  • Year Built: 2011

Lot Features

  • Lot Size (Acres): 2.4
  • Zoning: R1
  • Lot Description: Lightly Wooded, Level Lot

Financial Considerations

  • Assessment Amount: $218,050
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 2541286

Listed by Exceptional Real Estate LLC, Terence Dominick and Exceptional Real Estate LLC, Samuel Sylvia

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Listing agents

— 21 Jack Henry Dr —

  • Terence Dominick

    Exceptional Real Estate LLC

  • Samuel Sylvia

    Exceptional Real Estate LLC

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 21 Jack Henry Dr

School District:Windham School District
NameGradesDistance
Windham Center School
45 North Road, Windham, CT 06280
K-51.3 mi
Charles High Barrows Stem Academy
141 Tuckie Road, Windham, CT 06256
K-62.7 mi
Windham Middle School
123 Quarry St., Windham, CT 06226
6-84.9 mi
Windham High School
355 High St., Windham, CT 06226
9-124.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 21 Jack Henry Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/17/2026
Listed
$464,997
62.59%
MLS
6/30/2026
Sold
$286,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 21 Jack Henry Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,509
—
$218,050
—
2023
$6,518
17%
$218,050
51%
2023
$5,586
3%
$143,930
—
2022
$5,442
-4%
$143,930
—
2021
$5,672
1%
$143,930
—
2020
$5,599
1%
$143,930
—
2019
$5,527
4%
$143,930
5%
2017
$5,304
6%
$137,660
—
2015
$4,985
6%
$137,660
—
2014
$4,718
6%
$137,660
-5%
2011
$4,457
—
$145,570
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 21 Jack Henry Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Exceptional Real Estate LLC, Terence Dominick and Exceptional Real Estate LLC, Samuel Sylvia

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21 Jack Henry Drive, Windham, CT 06280 (MLS# 24207870) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 21 Jack Henry Drive is currently listed for $464,997 and was received on September 17, 2026. Want to learn more about 21 Jack Henry Drive? Do you have questions about finding other Single Family real estate for sale in Windham? You can browse all Windham real estate or contact a Coldwell Banker agent to request more information.

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