Windham County, CT homes for sale & real estate

295 homes

Sort:

Recommended

384 Prospect St, Windham, CT 06226
384 Prospect St, Windham, CT 06226
384 Prospect St, Windham, CT 06226
ABOUT THIS HOME
Windham County, CT Homes for Sale
Charming Victorian Home in the Heart of the Hill Section - Just Steps from ECSU This beautifully crafted Victorian residence offers over 3,000 sq ft of living space and is conveniently located near the entrance of Eastern Connecticut State University. Featuring a spacious chef's kitchen, an inviting front porch, and a covered back porch perfect for relaxing or entertaining. Inside, you'll find a stunning formal dining room, a generous living room with a cozy gas fireplace, and a grand entryway highlighted by a regal staircase. The home includes 6 bedrooms and 3.5 bathrooms, providing ample space. While the property requires some TLC-including yard maintenance and repairs to one bedroom aff

$335,000

6 beds3 baths3,274 sq ft

384 Prospect St, Windham, CT 06226

0.35 acre lot • Very walkable

126 Pine Hill Rd, Sterling, CT 06377
126 Pine Hill Rd, Sterling, CT 06377
126 Pine Hill Rd, Sterling, CT 06377
ABOUT THIS HOME
Windham County, CT Homes for Sale
26 x 34 two story OVERSIZED 2 car HEATED garage built in 2017 w/ 12 ft ceilings and wired for a lift, cable and wifi w/ LARGE 544 sq ft loft above! DOUBLE DECKS for entertaining overlooking 2.54 ACRES. COUNTRY home with 2023 ROOF! APPLIANCE kitchen w/ TILED floor open to dining and LARGE living room. LARGE bathroom w/ stand up shower, double vanity and jetted tub. 2 Spacious bedrooms on main floor. Lower level has a family room with wood stove (only use 100 gallons of oil a year with wood stove)and another room finished (currently used as a bedroom) with WALKOUT and 1 car garage. Close to RI line and 395 for easy commute. Some updating needed. Location, Location!

$349,900

2 beds1 bath1,664 sq ft

126 Pine Hill Rd, Sterling, CT 06377

2.54 acre lot • 3 garage spots • Car-dependent

188 Oxbow Dr, Windham, CT 06226
188 Oxbow Dr, Windham, CT 06226
188 Oxbow Dr, Windham, CT 06226
ABOUT THIS HOME
Windham County, CT Homes for Sale
This spacious Raised Ranch features a large kitchen with a center island and ample cabinetry, seamlessly connected to an open-concept living area-perfect for entertaining. The main level offers two comfortable bedrooms and a full bathroom. Downstairs, the finished lower level includes a second full bath and flexible space ideal for a home office, playroom, game room, or potential third bedroom. Direct access to the one-car garage adds convenience. Outside, enjoy a generous garden area and a large 10' x 16' storage shed, perfect for use as a workshop or for extra storage. Current street card shows 1 full bath. Building inspector completed a Certificate of Approval for the 2nd bath on 12/29/2

$283,900

2 beds1 bath1,178 sq ft

188 Oxbow Dr, Windham, CT 06226

9,147 sq ft lot • Garage • Car-dependent

NEW 7 HRS AGO

90-94 & 93 Upton Rd, Ashford, CT 06278
90-94 & 93 Upton Rd, Ashford, CT 06278
90-94 & 93 Upton Rd, Ashford, CT 06278
ABOUT THIS HOME
Windham County, CT Homes for Sale
Welcome to one of the most extraordinary and locally adored estates in Eastern Connecticut-nearly 300 acres of rolling fields, woodlands, and historic charm offered as a single, unmatched property. Privately set along a quiet, town-maintained dirt road, this expansive estate combines 93 and 90-94 Upton Road into a rare opportunity for legacy ownership. The centerpiece is a breathtaking 18th-century Cape, beautifully preserved and thoughtfully updated with modern systems and appliances, five fireplaces, a high-functioning, well-kept basement, and a detached two-car garage. From the stone walls, and the historic foundations to the vibrant gardens, the mature trees to the beautiful Knowlton an

$1,700,000

7 beds5 baths4,283 sq ft

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

291.6 acre lot • 2 garage spots • Pool

NEW 12 HRS AGO

29 Meadowbrook Dr, Brooklyn, CT 06234
29 Meadowbrook Dr, Brooklyn, CT 06234
29 Meadowbrook Dr, Brooklyn, CT 06234
ABOUT THIS HOME
Windham County, CT Homes for Sale
Welcome to this charming two-story home that blends classic appeal with modern comforts. From the moment you arrive, the covered front porch and decorative window shutters invite you in with timeless curb appeal. Inside, the kitchen stands out with sleek quartz countertops and flows seamlessly into the main living spaces, all featuring rich hardwood flooring that adds warmth and character throughout. Step outside to a backyard designed for enjoyment and gatherings. A sparkling pool serves as the centerpiece, for entertaining guests or relaxing in style. The entire outdoor space is fully fenced, providing both privacy and peace of mind. Additional potential awaits in the unfinished basement,

$474,995

3 beds2.5 baths1,836 sq ft

29 Meadowbrook Dr, Brooklyn, CT 06234

1.29 acre lot • Car-dependent

Property at 277 Gorman Rd, Brooklyn, CT 06234, 3 beds, 2 baths

$499,900

3 beds2 baths2,117 sq ft

277 Gorman Rd, Brooklyn, CT 06234

Property at 6 James St E, Putnam, CT 06260, 3 beds, 1.5 baths

$279,000

3 beds1.5 baths1,056 sq ft

6 James St E, Putnam, CT 06260

Property at 160 Halls Hill Rd, Killingly, CT 06239, 3 beds, 1.5 baths

$549,900

3 beds1.5 baths2,997 sq ft

160 Halls Hill Rd, Killingly, CT 06239

Property at 179 Hill Rd, Thompson, CT 06277, 4 beds, 3.5 baths

$750,000

4 beds3.5 baths4,016 sq ft

179 Hill Rd, Thompson, CT 06277

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 209 Church St, Windham, CT 06226, 4 beds, 2 baths

$279,900

4 beds2 baths2,275 sq ft

209 Church St, Windham, CT 06226

Property at 6 Kitty Ln, Windham, CT 06256, 2 beds, 1 bath

$57,000

2 beds1 bath728 sq ft

6 Kitty Ln, Windham, CT 06256

Property at 278 Snake Meadow Rd, Plainfield, CT 06354, 3 beds, 1 bath

$365,000

3 beds1 bath1,918 sq ft

278 Snake Meadow Rd, Plainfield, CT 06354

Property at 68 Bailey Hill Rd, Killingly, CT 06239, 4 beds, 2 baths

$439,999

4 beds2 baths2,304 sq ft

68 Bailey Hill Rd, Killingly, CT 06239

Property at 114 Breakneck Hill Rd, Killingly, CT 06241, 3 beds, 1 bath

$459,000

3 beds1 bath1,560 sq ft

114 Breakneck Hill Rd, Killingly, CT 06241

Property at 534 Margaret Henry Rd, Sterling, CT 06377, 3 beds, 1 bath

$299,900

3 beds1 bath1,290 sq ft

534 Margaret Henry Rd, Sterling, CT 06377

Property at 6 Nahaco Hill Ln, Eastford, CT 06242, 1 bed, 2 baths

$328,900

1 bed2 baths1,167 sq ft

6 Nahaco Hill Ln, Eastford, CT 06242

Property at 12 Charlton Ave, Killingly, CT 06241, 3 beds, 2.5 baths

$333,000

3 beds2.5 baths1,736 sq ft

12 Charlton Ave, Killingly, CT 06241

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 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 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 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 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 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

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
$279,450
Putnam homes for sale
$380,000
Moosup homes for sale
$365,000
Mansfield Center homes for sale
$240,000
Brooklyn homes for sale
$442,400

Counties

Hartford County homes for sale
$399,950
New Haven County homes for sale
$425,000
New London County homes for sale
$440,000

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.