20 Jack Henry Dr, Windham, CT 06280
Property image
Property image
OFF MARKET

20 Jack Henry Dr
Windham, CT 06280

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

$485,300

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $3,256/mo*
Refinance Your Home

$485,300

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $3,256/mo*
Refinance Your Home
4 Beds
2.5 Baths
1,869 sqft
(on 4 acres)

Home Value

Trulia Estimate
$485K
Since last month
Decreased$4K (-0.9%)
Since last year
Increased$7K (+1.4%)
Since last sale
Increased$233K (+93.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +106% in the last 10 years
MonthEstimated value
2026
August 2026$483K
July 2026$485K
June 2026$488K
May 2026$487K
April 2026$487K
March 2026$479K
February 2026$471K
January 2026$456K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
21 Jack Henry Dr, Windham, CT
0.17
Single-Family Home
$286,000
06/30/26
3
3
1,472
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
170 Windham Center Road, Windham, CT
0.54
Single-Family Home
$321,600
04/30/26
3
1
1,423

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
10 Henry Drive, Plainfield, CT 06354
0.11
$419,400
2
2
1,647
Off Market
17 Jack Henry Drive #13, Windham, CT 06280
0.21
-
-
-
-
Off Market
LOT7 (20) Jack Henry Drive, Windham, CT 06280
0.20
$501,200
3
2.5
1,750
Off Market
15 Jack Henry Drive, Windham, CT 06280
0.22
$461,100
-
-
-
Off Market
17 Jack Henry Drive, Windham, CT 06280
0.22
$515,000
3
2.5
1,814
Off Market
7 Autumn Ridge, Windham, CT 06280
0.28
$455,400
3
2.5
1,792
Off Market
5 Autumn Ridge, Windham, CT 06280
0.29
$527,000
4
3.5
2,368
Recently Sold
3 Autumn Ridge, Windham, CT 06280
0.33
$471,400
4
2.5
1,768
Off Market
125 Mullen Hill Road, Windham, CT 06280
0.37
$333,800
3
1.5
1,980
Off Market
24 Indian Hollow Road, Windham, CT 06280
0.36
$379,600
2
2
1,400
Off Market
4 Jerusalem Road, Windham, CT 06280
0.45
$379,000
3
2
1,938
Recently Sold
20 Cedar Hill Road, Willimantic, CT 06226
0.49
$471,100
3
3
1,821
Off Market

Local Information

  • Map ViewExplore the area around 20 Jack Henry Dr.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2009
Lot Size
4 acres
Living Area
1,869 sqft
Price/Sqft
$260
Parking
Garage

About this House

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.
20 Jack Henry Dr, Windham, CT 06280 is a 4 bedroom, 3 bathroom, 1,869 sqft single-family home built in 2009. It last sold for $250,000 on Sep 6, 2012. More recently, it was listed as a rental in May 2012 with an asking price of $2,000 per month. That rental listing was removed on May 31, 2012. It is currently off market. The Trulia Estimate is $485,300, with a rent estimate of $3,264/month.

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 and Tax history

DateEventPrice
Sep 21, 2019
Source: Agent Provided
ListingRemoved
$265,000
Sep 8, 2019
Source: Agent Provided
PriceChange
$265,000
Price decreased by 1%
Aug 17, 2019
Source: Agent Provided
PriceChange
$267,400
Price decreased by 1%
Aug 5, 2019
Source: Agent Provided
PriceChange
$269,900
Price decreased by 2%
Jul 22, 2019
Source: Agent Provided
PriceChange
$274,900
Price decreased by 2%

Market trends in Windham

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
13
3MoM
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Around this home

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!"
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  • 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. "
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  • 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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Off Market Homes Near 20 Jack Henry Dr

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Frequently asked questions about 20 Jack Henry Dr

  • What is 20 Jack Henry Dr estimated to be worth?
    Trulia's estimated value for 20 Jack Henry Dr in Windham, CT is $485,300.
  • What is the price history for 20 Jack Henry Dr?
    20 Jack Henry Dr in Windham, CT last sold for $250,000 in September 2012.
  • Is Windham a buyer's or seller's market?
    Windham is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Windham?
    Residents describe Windham, CT as easy to park in, quiet, and dog-friendly. Most residents say you need a car. See recently sold homes in Windham, CT.
  • Does 20 Jack Henry Dr have air conditioning?
    Yes, 20 Jack Henry Dr in Windham, CT has air conditioning.
  • How big is the lot at 20 Jack Henry Dr?
    The lot at 20 Jack Henry Dr in Windham, CT is about 4 acres.