Windham County, CT homes for sale & real estate

292 homes

Sort:

Recommended

OPEN TODAY, 10AM TO 12PM

68 Bailey Hill Rd, Killingly, CT 06239
68 Bailey Hill Rd, Killingly, CT 06239
68 Bailey Hill Rd, Killingly, CT 06239
ABOUT THIS HOME
Windham County, CT Homes for Sale
A WONDERFUL 4 bedroom colonial home located on the very desirable South Killingly road, Bailey Hill. Just inside the front door, you have your open dining room and living room. Both have newly refinished hardwood floors. The dining room features a wood burning fireplace. Then eat-in kitchen offers a large island breakfast bar, great for gatherings or casual dining. Beyond the kitchen is one of the best features, the sunroom! So many windows giving an amazing panoramic view of the far reaching backyard which includes a playscape. Also included with the home is a Cub Cadet ride-on tractor with snowblower attachment. Back into the house, there's no shortage of room, with an office to make life

$439,999

4 beds2 baths2,304 sq ft

68 Bailey Hill Rd, Killingly, CT 06239

1.1 acre lot • Car-dependent

OPEN TODAY, 10AM TO 12PM

114 Breakneck Hill Rd, Killingly, CT 06241
ABOUT THIS HOME
Windham County, CT Homes for Sale
Country Cape, Must be seen!!!!

$459,000

3 beds1 bath1,560 sq ft

114 Breakneck Hill Rd, Killingly, CT 06241

0.7 acre lot • Car-dependent

COMING SOON

534 Margaret Henry Rd, Sterling, CT 06377
534 Margaret Henry Rd, Sterling, CT 06377
534 Margaret Henry Rd, Sterling, CT 06377
ABOUT THIS HOME
Windham County, CT Homes for Sale
RUSTIC COUNTRY RANCH ON 1.15 ACRES right on the RI LINE. 10 x 16 and 16 x 26 HUGE DECK off the back of the home for entertaining overlooking FENCED area for your animals. 20 x 20 GARAGE for your vehicle and STORAGE. LARGE FIREPLACE living room, STAINLESS APPLIANCE kitchen w/ BEAUTIFUL GRANITE COUNTERS, NEW flooring leads to SPACIOUS dining area w/ SLIDER to DECK. 1 full bathroom and 3 bedrooms w/ NEW FLOORING and hallway too. FRESHLY PAINTED and ready for new owners who enjoy COUNTRY living w/ no sidewalks or street lights. CLOSE to 395 and RTE 6 for convenience. OUT in the COUNTRY but close to all shopping.

$299,900

3 beds1 bath1,290 sq ft

534 Margaret Henry Rd, Sterling, CT 06377

1.15 acre lot • Garage • Car-dependent

NEW 14 HRS AGO

6 Nahaco Hill Ln, Eastford, CT 06242
6 Nahaco Hill Ln, Eastford, CT 06242
6 Nahaco Hill Ln, Eastford, CT 06242
ABOUT THIS HOME
Windham County, CT Homes for Sale
WELCOME to Eastford where there are BEAUTIFUL 2025 STAND-ALONE Condos on a dead end cul de sac where you Can VIEW 2 MODELS. ONE YEAR WARRANTY and ONE LEVEL LIVING w/ NO Maintenance! STAINLESS appliances, WHITE shaker cabinets, ISLAND w/ GRANITE counters and VAULTED ceiling with OPEN FLOOR PLAN to BRIGHT living room w/ SLIDER to patio. LARGE Primary bedroom w/ HUGE closet and Primary bathroom with shower and GRANITE VANITY. OFFICE/ DEN and another 1/2-bathroom w/ laundry hook ups. FORCED hot AIR/CENTRAL air propane heat, PAVED DRIVEWAY and a deck in back to enjoy your evenings and a CONCRETE porch in front for your rocking chairs. EACH unit has its OWN septic. * * * FINISHED photos are of

$328,900

1 bed2 baths1,167 sq ft

6 Nahaco Hill Ln, Eastford, CT 06242

$200 HOA • 2 garage spots • Car-dependent

3D WALKTHROUGH

12 Charlton Ave, Killingly, CT 06241
12 Charlton Ave, Killingly, CT 06241
12 Charlton Ave, Killingly, CT 06241
ABOUT THIS HOME
Windham County, CT Homes for Sale
CAPTIVATINGLY SWEET! This open flow, ranch-styled home offers easy and incredibly spacious living. Loaded with deep closets and massive storage areas, there is also extra depth in the two-car, attached garage. A private, low-key entry ramp into the first floor is also available from the garage for further simplified accessibility. This well-loved, single-owner home was so well-sited on its lot with patio and outdoorsy spaces that entertaining is uncomplicated, and there are peaceful, quiet spaces in abundance. Rooms are sun-drenched and light even on the darkest days. They are also exceptionally large and smartly designed in a relatively open floor plan. 12 Charlton checks so many of the bo

$333,000

3 beds2.5 baths1,736 sq ft

12 Charlton Ave, Killingly, CT 06241

0.75 acre lot • 2 garage spots • Car-dependent

Property at 17 Jacqueline Ln, Windham, CT 06256, 3 beds, 2 baths

$110,000

3 beds2 baths1,248 sq ft

17 Jacqueline Ln, Windham, CT 06256

Property at 188 Oxbow Dr, Windham, CT 06226, 2 beds, 1 bath

$283,900

2 beds1 bath1,178 sq ft

188 Oxbow Dr, Windham, CT 06226

Property at 222 Southridge Dr, Windham, CT 06226, 3 beds, 1 bath

$249,000

3 beds1 bath1,076 sq ft

222 Southridge Dr, Windham, CT 06226

Property at 297 Sabin St #12, Putnam, CT 06260, 2 beds, 1.5 baths

$365,000

2 beds1.5 baths1,886 sq ft

297 Sabin St #12, Putnam, CT 06260

Property at 52 Park Dr, Chaplin, CT 06235, 2 beds, 1 bath

$149,900

2 beds1 bath733 sq ft

52 Park Dr, Chaplin, CT 06235

Property at 131 Windham Rd, Brooklyn, CT 06234, 3 beds, 2 baths

$399,900

3 beds2 baths1,682 sq ft

131 Windham Rd, Brooklyn, CT 06234

Property at 68 Allen Hill Rd, Brooklyn, CT 06234, 3 beds, 1.5 baths

$425,000

3 beds1.5 baths1,528 sq ft

68 Allen Hill Rd, Brooklyn, CT 06234

Property at 4 Bluebird Ln #4, Dayville, CT 06241, 2 beds, 2.5 baths

$443,000

2 beds2.5 baths1,430 sq ft

4 Bluebird Ln #4, Dayville, CT 06241

Property at 21 Union St, Plainfield, CT 06354, 9 beds, 4 baths

$319,000

9 beds4 baths2,640 sq ft

21 Union St, Plainfield, CT 06354

Property at 41 Jennings Ln, Windham, CT 06280, 3 beds, 1.5 baths

$385,000

3 beds1.5 baths1,712 sq ft

41 Jennings Ln, Windham, CT 06280

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 52 Singleton Rd, Chaplin, CT 06235, 3 beds, 2.5 baths

$339,900

3 beds2.5 baths2,440 sq ft

52 Singleton Rd, Chaplin, CT 06235

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

$299,000

2 beds1 bath1,040 sq ft

242 Herrick Rd, Brooklyn, CT 06234

Property at 81 Lovers Ln, Plainfield, CT 06374, 4 beds, 3 baths

$500,000

4 beds3 baths2,464 sq ft

81 Lovers Ln, Plainfield, CT 06374

Property at 62 Crooked Trl, Woodstock, CT 06281, 2 beds, 1.5 baths

$475,000

2 beds1.5 baths1,734 sq ft

62 Crooked Trl, Woodstock, CT 06281

Property at 157 Scotland Rd, Windham, CT 06280, 3 beds, 2.5 baths

$339,900

3 beds2.5 baths1,590 sq ft

157 Scotland Rd, Windham, CT 06280

Property at 8 Huntington Dr, Plainfield, CT 06374, 3 beds, 2.5 baths

$480,000

3 beds2.5 baths2,144 sq ft

8 Huntington Dr, Plainfield, CT 06374

Property at 1897 Upper Maple St, Killingly, CT 06241, 4 beds, 2 baths

$360,000

4 beds2 baths1,485 sq ft

1897 Upper Maple St, Killingly, CT 06241

Property at 384 Prospect St, Windham, CT 06226, 6 beds, 3.5 baths

$335,000

6 beds3.5 baths3,274 sq ft

384 Prospect St, Windham, CT 06226

Property at 3 Terrace Dr, Plainfield, CT 06374

$39,900

— beds— baths770 sq ft

3 Terrace Dr, Plainfield, CT 06374

Property at 211 Old Colony Rd, Eastford, CT 06242, 2 beds, 2 baths

$199,999

2 beds2 baths2,713 sq ft

211 Old Colony Rd, Eastford, CT 06242

Property at 184 Phoenixville Rd, Chaplin, CT 06235, 3 beds, 2 baths

$384,900

3 beds2 baths1,848 sq ft

184 Phoenixville Rd, Chaplin, CT 06235

Property at 19 Florence St, Putnam, CT 06260, 4 beds, 2 baths

$300,000

4 beds2 baths1,496 sq ft

19 Florence St, Putnam, CT 06260

Property at 156 Quaddick Rd, Thompson, CT 06277, 3 beds, 2 baths

$464,900

3 beds2 baths1,836 sq ft

156 Quaddick Rd, Thompson, CT 06277

Property at 1 Laurel Hill Dr, Woodstock, CT 06282, 3 beds, 1 bath

$579,900

3 beds1 bath1,323 sq ft

1 Laurel Hill Dr, Woodstock, CT 06282

Property at 94 Mansfield Rd, Ashford, CT 06278, 4 beds, 2 baths

$428,000

4 beds2 baths2,054 sq ft

94 Mansfield Rd, Ashford, CT 06278

Property at 256 Pine Hill Rd, Sterling, CT 06377, 1 bed, 1 bath

$130,000

1 bed1 bath720 sq ft

256 Pine Hill Rd, Sterling, CT 06377

Property at 686 Cook Hill Rd, Killingly, CT 06239, 4 beds, 2 baths

$409,900

4 beds2 baths1,068 sq ft

686 Cook Hill Rd, Killingly, CT 06239

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 433 Norwich Rd, Plainfield, CT 06374, 2 beds, 2 baths

$335,000

2 beds2 baths1,904 sq ft

433 Norwich Rd, Plainfield, CT 06374

Property at 316 Westminster Rd, Canterbury, CT 06331, 3 beds, 1 bath

$399,900

3 beds1 bath1,392 sq ft

316 Westminster Rd, Canterbury, CT 06331

Property at 245 Snake Meadow Hill Rd, Sterling, CT 06377, 3 beds, 3 baths

$630,000

3 beds3 baths1,833 sq ft

245 Snake Meadow Hill Rd, Sterling, CT 06377

Property at 164 Day St, Brooklyn, CT 06234, 3 beds, 2.5 baths

$409,000

3 beds2.5 baths1,300 sq ft

164 Day St, Brooklyn, CT 06234

Property at Undisclosed address, Killingly, CT 06239, 3 beds, 1 bath

$214,900

3 beds1 bath912 sq ft

Undisclosed address, Killingly, CT 06239

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 36 Dunleavy Dr, Woodstock, CT 06281, 3 beds, 2 baths

$549,000

3 beds2 baths2,036 sq ft

36 Dunleavy Dr, Woodstock, CT 06281

Viewing page 1 of 8

Average home prices near Windham County, CT

Cities

Plainfield Village homes for sale
$269,900
East Brooklyn homes for sale
$419,900
North Grosvenor Dale homes for sale
$399,500
Danielson homes for sale
$370,950
South Woodstock homes for sale
$559,000
Lake Bungee homes for sale
$539,450
Willimantic homes for sale
$279,000
Putnam homes for sale
$380,000
Moosup homes for sale
$329,500
Mansfield Center homes for sale
$240,000
Brooklyn homes for sale
$442,400

Counties

Hartford County homes for sale
$400,000
New Haven County homes for sale
$425,000
New London County homes for sale
$449,000

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)

$399,742

+12.6% YoY | Jun 2025

1 year
3 year
5 year

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

Location

Data

Jun 2025

Growth

% YoY

Windham County, CT

$399,742

+12.6%

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

Countries

United States

Canada

Updated January 2023: 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, TITLE FORWARD, 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

Rocket Mortgage is an affiliated business of Redfin. 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. For additional information on Rocket Mortgage or to receive lending services in the State of New York, please visit RocketMortgage.com.

Rocket Mortgage, LLC, Rocket Homes Real Estate LLC, Rocket Card, LLC, RockLoans Marketplace LLC (doing business as Rocket Loans), and Rocket Money, Inc., are separate operating subsidiaries of Rocket Limited Partnership. Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company is a separate legal entity operated and managed through its own management and governance structure. Rocket Limited Partnership is an indirect, wholly owned subsidiary of Rocket Companies, Inc. (NYSE: RKT).

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.