Cheap homes for sale & real estate in Windham County, CT

158 homes

Sort:

Recommended

NEW 21 HRS AGO

ABOUT THIS HOME
Cheap Home for sale in Windham County, CT:
Set on a peaceful 3.4-acre lot, this one-owner ranch offers privacy, space, and exciting potential. The main level features approximately 1,222 square feet with an open kitchen and living room layout, creating a welcoming central gathering space. A slider off the living area leads to a deck overlooking the wooded surroundings, perfect for enjoying the natural setting. The primary level includes a full bathroom, while the finished lower level adds approximately 375 square feet of living space complete with a second full bath, offering excellent in-law or guest suite potential. The rear boundary of the property extends down to Kitt Brook, providing a scenic and serene backdrop. Built in 1996,

$319,900

3 beds2 baths1,597 sq ft

21 Bennett Pond Rd, Canterbury, CT 06331

3.4 acre lot • Second full bath • Finished lower level

ABOUT THIS HOME
Cheap Home for sale in Windham County, CT:
This beautiful colonial is situated on a private lot in a wonderful cup-de-sac neighborhood setting. A unique aspect of this home is that it has 2 primary bedroom suites with one being on the first floor allowing for handicap accessibility if needed. Both bedroom suites feature full bathrooms, walk-in closets, hardwood floors and tile in the baths. You will love the spacious first floor open floor plan offering plenty of flexibility from the kitchen to the large living room with large windows bringing in plenty of natural light.

$364,900

3 beds3 baths2,128 sq ft

91 Insalaco Dr, Windham, CT 06280

Private lot • Full bathrooms • First floor

ABOUT THIS HOME
Cheap Home for sale in Windham County, CT:
Welcome to 123 Westfield Avenue in Danielson! This well-located property offers a fantastic opportunity for buyers seeking comfort, convenience, and value. Set on a quiet street yet close to local shops, dining, schools, and commuter routes, this home blends everyday practicality with small-town charm. Inside, you'll find a functional layout filled with natural light and flexible living spaces suited for today's lifestyle. Whether you're relaxing at home, entertaining guests, or working remotely, the floor plan provides versatility to meet your needs. The property also offers outdoor space ideal for enjoying warmer months, gardening, or simply unwinding. Perfect for owner-occupants or inves

$346,000

3 beds2 baths1,547 sq ft

123 Westfield Ave, Killingly, CT 06239

8,276 sq ft lot • 4 parking spots • Built 2003

ABOUT THIS HOME
Cheap Home for sale in Windham County, CT:
Cape-style home built in 1767, offering 6 rooms, 2 bedrooms, and 2 full bathrooms across 1,359 square feet. Features include a full basement and a one-car detached garage. The house and detached garage both have a new roof. Built in 1767, the property offers original architectural features alongside functional living space on a rural lot. This property is eligible under the Freddie Mac First Look Initiative through 01/16/2026. See agent remarks for offer submission instructions. Property to be sold in as-is condition.

$199,900

2 beds2 baths1,359 sq ft

261 Old Colony Rd, Eastford, CT 06242

Full basement • Rural lot • New roof

ABOUT THIS HOME
Cheap Home for sale in Windham County, CT:
Nestled back on 2 PRIVATE ACRES sits a sprawling COUNTRY ranch w/ APPLIANCE kitchen w/ NEW white shaker cabinets and countertops open to LARGE dining room. SPACIOUS living room and 3 bedrooms w/ 2 full bathrooms. ALMOST 1700 sq ft! Outbuilding for storage (there is NO basement). This is a COUNTRY home and setting perfect for animals! CAMERAS on property do NOT drive down driveway.

$349,900

3 beds2 baths1,680 sq ft

625 Pudding Hill Rd, Hampton, CT 06247

2 acre lot • Built 1965 • Listed 6 days

Property at 1741 Route 197 Rte, Woodstock, CT 06281, 3 beds, 2 baths

$399,900

3 beds2 baths1,596 sq ft

1741 Route 197 Rte, Woodstock, CT 06281

Property at 127 Windy Hill Rd, Hampton, CT 06247, 2 beds, 2 baths

$379,900

2 beds2 baths2,066 sq ft

127 Windy Hill Rd, Hampton, CT 06247

Property at 279 Gorman Rd, Brooklyn, CT 06234, 3 beds, 2 baths

$420,000

3 beds2 baths1,248 sq ft

279 Gorman Rd, Brooklyn, CT 06234

Property at 20 Jackson Rd, Plainfield, CT 06374, 3 beds, 2 baths

$425,000

3 beds2 baths1,752 sq ft

20 Jackson Rd, Plainfield, CT 06374

Property at 41 Carter St, Killingly, CT 06239, 4 beds, 2 baths

$325,000

4 beds2 baths1,694 sq ft

41 Carter St, Killingly, CT 06239

Property at 162 Scotland Rd, Windham, CT 06280, 3 beds, 2 baths

$299,000

3 beds2 baths1,401 sq ft

162 Scotland Rd, Windham, CT 06280

Property at 24 River Rd, Sterling, CT 06377, 4 beds, 2.5 baths

$399,900

4 beds2.5 baths2,272 sq ft

24 River Rd, Sterling, CT 06377

Property at 34 N Windham Rd, Windham, CT 06280, 4 beds, 2 baths

$330,000

4 beds2 baths1,294 sq ft

34 N Windham Rd, Windham, CT 06280

Property at 80 Sabin St, Putnam, CT 06260, 3 beds, 1.5 baths

$389,000

3 beds1.5 baths2,036 sq ft

80 Sabin St, Putnam, CT 06260

Property at 7 Jessie Ln, North Windham, CT 06256, 3 beds, 2 baths

$84,000

3 beds2 baths1,152 sq ft

7 Jessie Ln, North Windham, CT 06256

Property at 16 Wilkinson St, Putnam, CT 06260, 5 beds, 3.5 baths

$445,000

5 beds3.5 baths3,719 sq ft

16 Wilkinson St, Putnam, CT 06260

Property at 20 Toleration Rd, Baltic, CT 06330, 3 beds, 1 bath

$315,000

3 beds1 bath924 sq ft

20 Toleration Rd, Baltic, CT 06330

Property at 50 Brookside Dr, Dayville, CT 06241, 2 beds, 1 bath

$435,000

2 beds1 bath1,096 sq ft

50 Brookside Dr, Dayville, CT 06241

Property at 151 Brandy Hill Rd, Thompson, CT 06277, 3 beds, 1 bath

$349,000

3 beds1 bath1,423 sq ft

151 Brandy Hill Rd, Thompson, CT 06277

Property at 72 Perry St #143, Putnam, CT 06260, 2 beds, 2 baths

$235,000

2 beds2 baths1,000 sq ft

72 Perry St #143, Putnam, CT 06260

Property at 337 Hampton Rd, Chaplin, CT 06235, 3 beds, 2 baths

$295,000

3 beds2 baths1,652 sq ft

337 Hampton Rd, Chaplin, CT 06235

Property at 123 Ashford Rd #1, Eastford, CT 06242, 2 beds, 2 baths

$379,900

2 beds2 baths1,500 sq ft

123 Ashford Rd #1, Eastford, CT 06242

Property at 15 Cracow Ave, Windham, CT 06280, 3 beds, 2.5 baths

$325,000

3 beds2.5 baths1,228 sq ft

15 Cracow Ave, Windham, CT 06280

Property at 11 Stonehouse Dr, Moosup, CT 06354, 3 beds, 2 baths

$435,000

3 beds2 baths1,832 sq ft

11 Stonehouse Dr, Moosup, CT 06354

Property at 150 Gager Hill Rd, Windham, CT 06280, 6 beds, 1.5 baths

$179,900

6 beds1.5 baths2,634 sq ft

150 Gager Hill Rd, Windham, CT 06280

Property at 360 N Society Rd, Canterbury, CT 06331, 3 beds, 1.5 baths

$275,000

3 beds1.5 baths2,236 sq ft

360 N Society Rd, Canterbury, CT 06331

Property at 230 Cemetery Rd, Plainfield, CT 06374, 3 beds, 1.5 baths

$399,000

3 beds1.5 baths1,448 sq ft

230 Cemetery Rd, Plainfield, CT 06374

Property at 338 Main St, Hampton, CT 06247, 4 beds, 2 baths

$429,900

4 beds2 baths2,778 sq ft

338 Main St, Hampton, CT 06247

Property at 48 Athol St #48, Danielson, CT 06239, 2 beds, 1.5 baths

$193,000

2 beds1.5 baths1,076 sq ft

48 Athol St #48, Danielson, CT 06239

Property at 363 Windham Rd, Willimantic, CT 06226, 3 beds, 2 baths

$245,000

3 beds2 baths2,219 sq ft

363 Windham Rd, Willimantic, CT 06226

Property at 49 Canterbury Rd Apt K, Plainfield, CT 06374, 1 bed, 1 bath

$135,000

1 bed1 bath718 sq ft

49 Canterbury Rd Apt K, Plainfield, CT 06374

Property at 3 Ferland Dr, Dayville, CT 06241, 3 beds, 1 bath

$299,000

3 beds1 bath936 sq ft

3 Ferland Dr, Dayville, CT 06241

Property at 29 Church St, Killingly, CT 06241, 8 beds, 2 baths

$325,000

8 beds2 baths2,590 sq ft

29 Church St, Killingly, CT 06241

Property at 23 Mechanics St #101, Putnam, CT 06260, 1 bed, 1 bath

$129,000

1 bed1 bath448 sq ft

23 Mechanics St #101, Putnam, CT 06260

Property at 385 Putnam Pike, Dayville, CT 06241, 5 beds, 3 baths

$370,000

5 beds3 baths2,700 sq ft

385 Putnam Pike, Dayville, CT 06241

Property at 89 Spring St, Willimantic, CT 06226, 4 beds, 1.5 baths

$264,900

4 beds1.5 baths1,907 sq ft

89 Spring St, Willimantic, CT 06226

Property at Undisclosed address, Chaplin, CT 06235, 3 beds, 1 bath

$315,000

3 beds1 bath1,267 sq ft

Undisclosed address, Chaplin, CT 06235

Property at 11 Kenneth Dr, Dayville, CT 06241, 3 beds, 3 baths

$410,000

3 beds3 baths1,444 sq ft

11 Kenneth Dr, Dayville, CT 06241

Property at 63 Athol St #63, Danielson, CT 06239, 2 beds, 1.5 baths

$215,000

2 beds1.5 baths1,064 sq ft

63 Athol St #63, Danielson, CT 06239

Property at 30 Valley, North Grosvenordale, CT 06255, 3 beds, 1 bath

$340,000

3 beds1 bath1,069 sq ft

30 Valley, North Grosvenordale, CT 06255

Property at 106 Tripp Hollow Rd, Brooklyn, CT 06234, 4 beds, 2.5 baths

$365,000

4 beds2.5 baths2,220 sq ft

106 Tripp Hollow Rd, Brooklyn, CT 06234

Viewing page 1 of 4

Cheap Homes for Sale in Windham County

There are currently 158 cheap homes for sale in Windham County at a median listing price of $392K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windham County stay on the market for 51 days and receive 1 offers. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 93 homes have been sold in Windham County. In addition to houses in Windham County, there were also 27 condos, 1 townhouse, and 23 multi-family units for sale in Windham County last month. Find your dream home in Windham County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Windham County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windham County. If you're looking to sell your home in the Windham County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windham County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Windham County, CT

Cities

Nearby Counties

Nearby Counties with Cheap Homes

Nearby Cities with Cheap Homes

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.