Windham County, CT homes for sale & real estate

243 homes

Sort:

Recommended

ABOUT THIS HOME
Windham County, CT Homes for Sale
Situated in tranquil Woodstock, this spacious four bedroom Cape is the ultimate hidden treasure. It's calm, tree-lined 4.23 acres opens up to offer a large yard to allow space for all of your outdoor activities. Inside, you will be met with a smooth-flowing layout, 9ft ceilings, and plenty of natural lighting. The first level homes two sizeable bedrooms that transition into the main living space and a charming multi-use room currently being used as a play room! Up the stairs you will find the remaining two bedrooms, an open foyer area, and half bathroom. Don't forget to make your way down to the walk-out basement to be surprised with another half bath/ wet bar and a garage with workshop are

$423,000

4 beds1.5 baths1,904 sq ft

381 Bungay Hill Rd, Woodstock, CT 06281

Multi-use room • Wet bar • Large yard

ABOUT THIS HOME
Windham County, CT Homes for Sale
Welcome to the original parsonage of the Chaplin Congregational Church in the historic district in Chaplin! In 1837, the land was purchased from Luther Ridley. This spacious home was constructed in 1840. The parsonage has been home to many ministers and their families. The front parlor has seen many functions through the years, including weddings. The Ladies Aid Society has used the upstairs parlor for quilting bees before the home was sold by the church in 1985. Goodwin Forest hiking trails and the Airline Trial have access points in Chaplin. Seller to find suitable housing.

$425,000

3 beds2 baths2,438 sq ft

60 Chaplin St, Chaplin, CT 06235

Front parlor • Airline trail access • Historic district

ABOUT THIS HOME
Windham County, CT Homes for Sale
This beautiful sprawling custom colonial is set on 9 acres of land at the end of a winding long driveway and surrounded by open area. Grand living spaces with cathedral ceilings and a floor to ceiling fireplace, tons of natural light, 4 bedrooms & 3.5 bathrooms, a 1500 sqft in-law suite with additional bedroom, new appliances, spacious 2 car garage, and an out building with electricity and storage loft. Enjoy the "Quiet Corner of Connecticut" today with the most beautiful autumn foliage, nearby hiking, golf, and beautiful country roads.

$659,900

4 beds3.5 baths4,536 sq ft

101 Center Rd, Woodstock, CT 06281

Custom colonial • In-law suite • 9 acres of land

ABOUT THIS HOME
Windham County, CT Homes for Sale
SELLER SAYS SELL SELL SELL!! Book your private tour today! Welcome to this great 2 family with many many updates. Brand new roof. Great commuter location. This family style setting 2 units side by side with 3 bedrooms 1 bath each unit. First floor features many windows for natural sunlight, Livingroom, eat in kitchen and bedroom. 2nd floor offers an additional 2 bedrooms. The back yard is level for entertaining or spending time. Perfect for owner occupied or investment. This building is owner occupied on both sides and will be delivered empty being able to move right in or fill with market price rents.

$289,999

6 beds2 baths2,600 sq ft

144 Prospect Ave, Killingly, CT 06239

Commuter location • Natural sunlight • New roof

ABOUT THIS HOME
Windham County, CT Homes for Sale
If you are looking for everything this is the home for you. Home sits on 3.39 acres of beautiful land with a 36x48 Morton barn that has 2 stalls but could be 6, or if you want a kennel it is set up with 5 doggy doors into barn has water and electric and can be heated if you want. Nice areas for pasture and also a chicken coop with water and electric. The home has been completely renovated in the last 2 years and offers front porch with Mahogany entry, Brazilian Walnut floors (IPE) in entry, office, living room and kitchen. Livingroom with vaulted ceilings, fireplace, opens into dining area in kitchen with doors to back deck, kitchen is perfect for the person who loves to cook. Soap stone co

$789,000

4 beds2.5 baths2,900 sq ft

287 S Bear Hill Rd, Chaplin, CT 06235

36x48 barn • 3.39 acres • Front porch

Property at 17 Green Is, Thompson, CT 06277, 2 beds, 1 bath

$369,900

2 beds1 bath440 sq ft

17 Green Is, Thompson, CT 06277

Property at 402 Whetstone Mls #402, Dayville, CT 06241, 2 beds, 1.5 baths

$269,000

2 beds1.5 baths1,318 sq ft

402 Whetstone Mls #402, Dayville, CT 06241

Property at 36 Olde Meadow Rd, Woodstock, CT 06281, 4 beds, 3.5 baths

$895,000

4 beds3.5 baths3,300 sq ft

36 Olde Meadow Rd, Woodstock, CT 06281

Property at 8 John's Cir Lot 33, Sterling, CT 06377, 3 beds, 2 baths

$449,900

3 beds2 baths1,400 sq ft

8 John's Cir Lot 33, Sterling, CT 06377

Property at 498 Bailey Hill Rd, Killingly, CT 06241, 5 beds, 3 baths

$1,100,000

5 beds3 baths2,771 sq ft

498 Bailey Hill Rd, Killingly, CT 06241

Property at 29 Prospect St Unit A, Putnam, CT 06260, 3 beds, 1.5 baths

$294,900

3 beds1.5 baths1,200 sq ft

29 Prospect St Unit A, Putnam, CT 06260

Property at 90-94 & 93 Upton Rd, Ashford, CT 06278, 7 beds, 5 baths

$1,700,000

7 beds5 baths4,283 sq ft

90-94 & 93 Upton Rd, Ashford, CT 06278

Property at 357 Wrights Crossing Rd, Pomfret Center, CT 06259, 5 beds, 5.5 baths

$2,500,000

5 beds5.5 baths7,772 sq ft

357 Wrights Crossing Rd, Pomfret Center, CT 06259

Property at 26 Perkins St, Plainfield, CT 06374, 3 beds, 1.5 baths

$323,000

3 beds1.5 baths1,760 sq ft

26 Perkins St, Plainfield, CT 06374

Property at 246 Heritage Rd, Putnam, CT 06260, 3 beds, 2 baths

$995,000

3 beds2 baths2,537 sq ft

246 Heritage Rd, Putnam, CT 06260

Property at 8 Juniper Ln, Moosup, CT 06354, 3 beds, 1.5 baths

$449,900

3 beds1.5 baths2,146 sq ft

8 Juniper Ln, Moosup, CT 06354

Property at 115 Grove St, Putnam, CT 06260, 9 beds, 3.5 baths

$539,900

9 beds3.5 baths5,046 sq ft

115 Grove St, Putnam, CT 06260

Property at 242 Herrick Rd, Brooklyn, CT 06234, 2 beds, 1 bath

$290,000

2 beds1 bath1,040 sq ft

242 Herrick Rd, Brooklyn, CT 06234

Property at 69 N Bedlam Rd, Chaplin, CT 06235, 3 beds, 2 baths

$599,000

3 beds2 baths1,979 sq ft

69 N Bedlam Rd, Chaplin, CT 06235

Property at 68 Roode Rd, Plainfield, CT 06374, 5 beds, 4.5 baths

$699,000

5 beds4.5 baths3,886 sq ft

68 Roode Rd, Plainfield, CT 06374

Property at 393 N Canterbury Rd, Canterbury, CT 06331, 5 beds, 2 baths

$595,000

5 beds2 baths2,443 sq ft

393 N Canterbury Rd, Canterbury, CT 06331

Property at 76 Mill Brook Ln, Woodstock, CT 06281, 5 beds, 4 baths

$1,100,000

5 beds4 baths5,079 sq ft

76 Mill Brook Ln, Woodstock, CT 06281

Property at 70 Laurel Hill Dr, Woodstock, CT 06281, 3 beds, 2.5 baths

$420,000

3 beds2.5 baths1,682 sq ft

70 Laurel Hill Dr, Woodstock, CT 06281

Property at 66 Bebbington Rd, Ashford, CT 06278, 5 beds, 4.5 baths

$2,995,000

5 beds4.5 baths5,977 sq ft

66 Bebbington Rd, Ashford, CT 06278

Property at 70 Laurel Hill Dr, Woodstock Valley, CT 06282, 3 beds, 2.5 baths

$420,000

3 beds2.5 baths1,682 sq ft

70 Laurel Hill Dr, Woodstock Valley, CT 06282

Property at 23 Little Bunggee Hill Rd, Woodstock Valley, CT 06282, 4 beds, 2 baths

$569,000

4 beds2 baths2,160 sq ft

23 Little Bunggee Hill Rd, Woodstock Valley, CT 06282

Property at Undisclosed address, Windham, CT 06280, 3 beds, 2.5 baths

$295,000

3 beds2.5 baths2,248 sq ft

Undisclosed address, Windham, CT 06280

Property at 1669 Route 169, Woodstock, CT 06281, 2 beds, 2 baths

$1,250,000

2 beds2 baths2,340 sq ft

1669 Route 169, Woodstock, CT 06281

Property at 180 Jericho Rd, Pomfret Center, CT 06259, 3 beds, 3.5 baths

$975,000

3 beds3.5 baths3,460 sq ft

180 Jericho Rd, Pomfret Center, CT 06259

Property at 300 Valley Rd, Killingly, CT 06241, 4 beds, 2.5 baths

$694,900

4 beds2.5 baths2,610 sq ft

300 Valley Rd, Killingly, CT 06241

Property at 80 John Mack Rd, Hampton, CT 06247, 3 beds, 2 baths

$575,000

3 beds2 baths1,344 sq ft

80 John Mack Rd, Hampton, CT 06247

Property at 1 Johns Cir, Sterling, CT 06377, 3 beds, 2.5 baths

$419,900

3 beds2.5 baths1,776 sq ft

1 Johns Cir, Sterling, CT 06377

Property at 56 Laurel Hill Dr, Woodstock Valley, CT 06282, 3 beds, 1.5 baths

$475,000

3 beds1.5 baths1,008 sq ft

56 Laurel Hill Dr, Woodstock Valley, CT 06282

Property at 297 Main St, Hampton, CT 06247, 3 beds, 2 baths

$160,000

3 beds2 baths1,654 sq ft

297 Main St, Hampton, CT 06247

Property at 50 High St, Moosup, CT 06354, 4 beds, 4 baths

$465,000

4 beds4 baths5,176 sq ft

50 High St, Moosup, CT 06354

Property at 402 Perrin Rd, Woodstock, CT 06281, 3 beds, 2 baths

$679,000

3 beds2 baths2,669 sq ft

402 Perrin Rd, Woodstock, CT 06281

Property at Brook Rd Lot 4, Hampton, CT 06247

$85,000

— beds— baths— sq ft

Brook Rd Lot 4, Hampton, CT 06247

Property at 627 Bailey Rd, Sterling, CT 06377

$35,000

— beds— baths— sq ft

627 Bailey Rd, Sterling, CT 06377

Property at 131 Church St, Sterling, CT 06377

$400,000

— beds— baths— sq ft

131 Church St, Sterling, CT 06377

Property at 0 Wauregan Rd, Plainfield, CT 06374

$750,000

— beds— baths— sq ft

0 Wauregan Rd, Plainfield, CT 06374

Property at Lot 12-1 Tripp Hollow Rd, Brooklyn, CT 06234

$139,900

— beds— baths— sq ft

Lot 12-1 Tripp Hollow Rd, Brooklyn, CT 06234

Viewing page 4 of 6

Average home prices near Windham County, CT

Cities

Plainfield Village homes for sale
$329,000
East Brooklyn homes for sale
$389,450
North Grosvenor Dale homes for sale
$365,000
Danielson homes for sale
$287,500
South Woodstock homes for sale
$479,000
Willimantic homes for sale
$264,900
Putnam homes for sale
$379,450
Moosup homes for sale
$420,000
Quinebaug homes for sale
$347,500
Mansfield Center homes for sale
Brooklyn homes for sale
$365,000
Dayville homes for sale
$499,900

Counties

Hartford County homes for sale
$379,900
New Haven County homes for sale
$399,900
New London County homes for sale
$415,000

Windham County, CT real estate trends

All Home Types trends in Windham County, CT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$360,000

+5.9% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

Windham County, CT

$360,000

+5.9%

See more Windham County, CT market insights

More to explore in Windham County, CT

How to buy a house in Windham County, CT

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Connecticut

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.