20 Jack Henry Dr, Windham, CT 06280
OFF MARKET

20 Jack Henry Dr
Windham, CT 06280

  • 4 Beds
  • 2.5 Baths
  • 1,869 sqft (on 4 acres)

$484,200

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $3,208/mo*
Refinance Your Home

$484,200

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $3,208/mo*
Refinance Your Home
4 Beds
2.5 Baths
1,869 sqft
(on 4 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Must see! Privacy plus elegant Cape in move in condition on cul de sac. This home features privacy, hardwood floors in amazing condition, 2 central air conditioning units (one unit per floor),RV hookup, security system, large covered back porch, with ceiling fan, wonderful 2 car garage with room for workshop, generator hookup. Jacuzzi hookup near the patio. Owners downsizing.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 20 Jack Henry Dr

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: Baseboard, Electric, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
MicrowaveRefrigerator
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Vinyl
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2009
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 4.00 acres

Price History for 20 Jack Henry Dr

DatePriceEventSource
09/21/2019$265,000ListingRemovedAgent Provided
09/08/2019$265,000PriceChange
Agent Provided
08/17/2019$267,400PriceChange
Agent Provided
08/05/2019$269,900PriceChange
Agent Provided
07/22/2019$274,900PriceChange
Agent Provided
07/05/2019$279,900PriceChange
Agent Provided
07/03/2019$289,000Listed For SaleAgent Provided
09/06/2012$250,000Sold
Smart MLS #E258135
06/02/2012$249,900PriceChange
Agent Provided
05/31/2012$2,000ListingRemovedAgent Provided
05/23/2012$259,900Listed For SaleAgent Provided
05/22/2012$2,000Listed For RentAgent Provided
01/15/2010$236,000Sold
N/A
07/01/2009$60,000Sold
Smart MLS #G480535
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Property Tax and Assessment

Year2025
Tax$8,019
Assessment$268,630
Home facts updated by county records

Comparable Sales for 20 Jack Henry Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
7 Autumn Ridge, Windham, CT
0.28
Single-Family Home
$430,000
10/06/25
3
2.5
1,792
4 Jerusalem Road, Windham, CT
0.45
Single-Family Home
$379,000
12/17/25
3
2
1,938
5 Autumn Ridge, Windham, CT
0.29
Single-Family Home
$527,000
05/01/26
4
3.5
2,368
69 Mullen Hill Rd, Windham, CT
0.64
Single-Family Home
$449,000
09/09/25
4
3
2,031
91 Insalaco Drive, Windham, CT
0.67
Single-Family Home
$362,900
03/27/26
3
3
2,128
47 Insalaco Drive, Windham, CT
0.76
Single-Family Home
$379,900
12/09/25
3
2.5
2,112
121 Insalaco Drive, Windham, CT
0.58
Single-Family Home
$447,000
04/30/26
3
2.5
2,388
22 Indian Hollow Rd, Windham, CT
0.41
Single-Family Home
$55,000
10/30/25
2
2
1,697
28 Patriot Rd, Windham, CT
0.83
Single-Family Home
$365,000
07/17/25
4
2
1,980
39 Windham Center Road, Windham, CT
0.86
Single-Family Home
$325,000
07/30/25
4
1.5
2,383

Assigned Schools

These are the assigned schools for 20 Jack Henry Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windham

At least 25 Trulia users voted on each feature.

  • 76 % Say car is needed

  • 74 % Say parking is easy

  • 74 % Say it's quiet

  • 70 % Say there's wildlife

  • 68 % Say it's dog friendly

  • 67 % Say yards are well-kept

  • 57 % Say kids play outside

  • 53 % Say people would walk alone at night

  • 52 % Say neighbors are friendly

  • 47 % Say there's holiday spirit

  • 41 % Say streets are well-lit

  • 37 % Say it's walkable to restaurants

  • 36 % Say there are community events

  • 32 % Say there are sidewalks

  • 32 % Say they plan to stay for at least 5 years

  • 30 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Kissle26
    "Its fine. My office is only a 10 minutes drive (or less). It’s mostly back roads but they are usually cleaned off and whatnot!"
    0
    Flag
  • Lindsay F.
    "very quiet and friendly community, close enough to commute to and from hartford county but far enough away from the city to be able to enjoy rural settings"
    1
    Flag
  • Bobbyquiles
    "Living here for 3 years now and we love the area. Quite and peaceful. The wild turkeys, deer, and he hummingbirds"
    1
    Flag
  • Tiffany H.
    "Its 75% Puerto Rican. The taxes are very high. You pay for police, but they won't come. Only state police do, when they get around to it. "
    0
    Flag
  • D L.
    "I lived in this area for 26 years. It has always been a great neighborhood! You have plenty of privacy while still being close to others to feel comfortable and supported. It is a great neighborhood for children or retirees. Beacon Rd. is only five miles from downtown where there are several restaurants and a variety of shopping for food and other needs. The schools do not get the credit that they deserve, but they are very progressive and they offer a variety of educational support services, both for the students and the staff. The student population is diverse and there is a brand-new state-of-the-art science-based school for grades K thru 8. They offer a variety of sports and other extra-curricular activities; football, soccer, track, swimming, baseball, softball, wrestling and tennis. They also offer before and after-school child care programs for grades K thru 8. There is a State University in the town of Willimantic, Eastern CT State University and UCONN (the University of CT') is only 17 miles away. Manchester CT is only about 25 miles away and there is all the shopping and stores that you could think of available there. Beacon Rd. has always been a great neighborhood to live in and to raise our kids in. It is well known as one of the "better" areas of Windham/Willimantic. The people take pride in their properties and the area has maintained a good value, even through these difficult times. There is ample parking for family and friends and the road is well maintained. Check it out! "
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Apartments for Rent

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Homes for sale near 20 Jack Henry Dr

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Homes for rent near 20 Jack Henry Dr

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Off Market Homes Near 20 Jack Henry Dr

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20 Jack Henry Dr, Windham, CT 06280 is a 4 bedroom, 3 bathroom, 1,869 sqft single-family home built in 2009. This property is not currently available for sale. 20 Jack Henry Dr was last sold on Sep 6, 2012 for $250,000. The current Trulia Estimate for 20 Jack Henry Dr is $484,200.