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

89 homes

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OPEN SAT, 10:30AM TO 12PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Welcome to this inviting 4-bedroom, 2-bathroom home offering plenty of flexibility for a growing household. Situated on a 0.18-acre lot in the heart of Putnam, this property combines convenience with the charm of small-town living. Enjoy easy access to local schools, shopping, dining, and major routes for commuting. Inside, you'll find generous living spaces filled with natural light and plenty of potential to make the home your own. This property is ready for renovations and offers an excellent opportunity for a buyer/investor looking to add value and personalize a home to their liking. Seller is motivated-bring all offers! Property is being sold AS IS, WHERE IS. Cash, hard money, or conve

$225,000

3 beds1 bath1,367 sq ft

24 Tatem St, Putnam, CT 06260

7,840 sq ft lot • Garage • Built 1890

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
1940's Cape Cod style home that has been completely remodeled from the studs in over the past 25 years of ownership. Home features a flexible floor plan with 3 bedrooms and 1.5 bathrooms, a large & open eating space kitchen, first floor bedroom potential, along with over 1/2 AC of yard and a large Barn Yard detached Garage/Shed with power perfect for toys & vehicles. Newer septic updated 200-amp circuit breakers with generator ready connections & fully insulated. First floor features a tiled floor kitchen, wood floors in the living room along with the 1st floor bedroom currently utilized as an offer. The full bathroom was recently renovated & updated. Upstairs, 2 add

$359,900

3 beds1.5 baths1,215 sq ft

133 Church St, Thompson, CT 06277

0.57 acre lot • Garage • Built 1940

OPEN SAT, 2PM TO 3:30PM3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Whether you're looking for abundant living space, room for extended household members, or an investment opportunity, this spacious 5-bedroom, 2-bath home offers exceptional flexibility in a prime Windham location. The home features generously sized bedrooms, updated bathrooms, and a versatile floor plan that can easily adapt to a variety of needs. A possible sixth bedroom on the first floor provides even more options for a home office, guest room, or additional living space. Previously utilized as a 6-bedroom rental, the home offers an abundance of space and functionality. A detached 2-car garage and expansive driveway provide ample parking, while the generous . 41-acre lot offers a surpris

$362,500

6 beds2 baths2,181 sq ft

371 Prospect St, Willimantic, CT 06226

Spacious yard • Expansive driveway • Generous lot

NEW 21 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
INVESTOR OPPORTUNITY IN WILLIMANTIC! Bring your vision to 86 Chestnut Street, an approximately 1,560 SF multifamily property. Originally built in 1887, the property offers timeless architectural character and charm rarely found in newer construction. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shops, restaurants, services, and major area routes. Offered AS-IS, providing an opportunity to renovate and customize to your investment strategy. The property's character, layout, location, and value-add potential make this an excellent opportunity for an investor or owner-occupant. Cash or conventional financing only. No government financing. Buyer to condu

$290,000

4 beds2 baths1,560 sq ft

86 Chestnut St, Willimantic, CT 06226

6,969 sq ft lot • Garage • Built 1887

NEW 22 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Cape style home with stone and vinyl exterior, and a private back yard with pretty gardens. The great room is large and bright and offers multiple uses and conveys with a pool table. It is heated with a propane fireplace and cooled with a mini-split. Town card states 3 bedrooms and 2 full baths. The main floor bedroom was modified to include laundry, and has direct access to a full bath. The two other bedrooms are on the second level, and are pass through style. The living room and dining room offer flexibility for other uses. The roof is 6 years old, and most of the windows have been replaced. There is a shed in the back yard for storage, and a nice circular paved drive. Subject to probate

$285,000

3 beds2 baths1,409 sq ft

506 Church St, Putnam, CT 06260

Propane fireplace • Private back yard • Mini-split

Property at 137 Hawkins St, Killingly, CT 06239, 3 beds, 1.5 baths

$285,000

3 beds1.5 baths1,260 sq ft

137 Hawkins St, Killingly, CT 06239

Property at 81 Hawkins St, Killingly, CT 06239, 3 beds, 2 baths

$350,000

3 beds2 baths1,854 sq ft

81 Hawkins St, Killingly, CT 06239

Property at 369 Thompson Rd, Thompson, CT 06277, 4 beds, 3.5 baths

$584,900

4 beds3.5 baths2,944 sq ft

369 Thompson Rd, Thompson, CT 06277

Property at 29 Vandall St, North Grosvenordale, CT 06255, 3 beds, 2 baths

$499,000

3 beds2 baths4,907 sq ft

29 Vandall St, North Grosvenordale, CT 06255

Property at 11 Bellevue St, Willimantic, CT 06226, 6 beds, 2 baths

$175,000

6 beds2 baths1,948 sq ft

11 Bellevue St, Willimantic, CT 06226

Property at 51 Gallup St, Plainfield, CT 06374, 3 beds, 1 bath

$285,000

3 beds1 bath1,251 sq ft

51 Gallup St, Plainfield, CT 06374

Property at 15 Bellevue St, Willimantic, CT 06226, 4 beds, 1.5 baths

$199,000

4 beds1.5 baths1,807 sq ft

15 Bellevue St, Willimantic, CT 06226

Property at 127 Valley Rd, Killingly, CT 06239, 4 beds, 2 baths

$599,900

4 beds2 baths1,889 sq ft

127 Valley Rd, Killingly, CT 06239

Property at 86 Thompson Hill Rd, North Grosvenordale, CT 06255, 3 beds, 1.5 baths

$300,000

3 beds1.5 baths1,025 sq ft

86 Thompson Hill Rd, North Grosvenordale, CT 06255

Property at 245 School St, Putnam, CT 06260, 3 beds, 1 bath

$200,000

3 beds1 bath2,684 sq ft

245 School St, Putnam, CT 06260

Property at 362 Thompson Rd, Thompson, CT 06277, 7 beds, 3.5 baths

$749,900

7 beds3.5 baths4,231 sq ft

362 Thompson Rd, Thompson, CT 06277

Property at 143 Main St, Sterling, CT 06377, 3 beds, 1 bath

$295,000

3 beds1 bath1,056 sq ft

143 Main St, Sterling, CT 06377

Property at 33 Machine Shop Hill Rd, South Windham, CT 06266, 4 beds, 3.5 baths

$549,900

4 beds3.5 baths2,548 sq ft

33 Machine Shop Hill Rd, South Windham, CT 06266

Property at 130 Windham Rd, Willimantic, CT 06226, 4 beds, 2.5 baths

$335,000

4 beds2.5 baths2,379 sq ft

130 Windham Rd, Willimantic, CT 06226

Property at 64 Katherine Ave, Killingly, CT 06070, 3 beds, 1 bath

$299,900

3 beds1 bath1,178 sq ft

64 Katherine Ave, Killingly, CT 06070

Property at 31 Palmer St, Killingly, CT 06239, 3 beds, 2 baths

$320,000

3 beds2 baths1,351 sq ft

31 Palmer St, Killingly, CT 06239

Property at 111 Island Rd, Killingly, CT 06241, 3 beds, 1 bath

$335,000

3 beds1 bath1,282 sq ft

111 Island Rd, Killingly, CT 06241

Property at 31 Canterbury Rd, Brooklyn, CT 06234, 4 beds, 3.5 baths

$500,000

4 beds3.5 baths2,879 sq ft

31 Canterbury Rd, Brooklyn, CT 06234

Property at 23 Totem Pole Rd, Thompson, CT 06277, 4 beds, 3 baths

$650,000

4 beds3 baths2,574 sq ft

23 Totem Pole Rd, Thompson, CT 06277

Property at 273 Hartford Rd, Brooklyn, CT 06234, 3 beds, 2 baths

$399,900

3 beds2 baths1,643 sq ft

273 Hartford Rd, Brooklyn, CT 06234

Property at 21-23 George St, Putnam, CT 06260, 6 beds, 2 baths

$249,900

6 beds2 baths1,993 sq ft

21-23 George St, Putnam, CT 06260

Property at 136 Hartford Rd, Brooklyn, CT 06234, 5 beds, 2 baths

$479,900

5 beds2 baths1,551 sq ft

136 Hartford Rd, Brooklyn, CT 06234

Property at 11 N Canterbury Rd, Canterbury, CT 06331, 3 beds, 2 baths

$399,600

3 beds2 baths2,700 sq ft

11 N Canterbury Rd, Canterbury, CT 06331

Property at 128 Holmes Rd, Pomfret Center, CT 06259, 4 beds, 3 baths

$545,000

4 beds3 baths2,893 sq ft

128 Holmes Rd, Pomfret Center, CT 06259

Property at 207 Summit St, Willimantic, CT 06226, 3 beds, 2 baths

$365,000

3 beds2 baths2,318 sq ft

207 Summit St, Willimantic, CT 06226

Property at 1232 Riverside Dr, North Grosvenordale, CT 06255, 2 beds, 1 bath

$385,000

2 beds1 bath1,161 sq ft

1232 Riverside Dr, North Grosvenordale, CT 06255

Property at 85 Wauregan Rd, Killingly, CT 06387, 3 beds, 1.5 baths

$204,500

3 beds1.5 baths1,446 sq ft

85 Wauregan Rd, Killingly, CT 06387

Property at 39 Sterling Hill Rd, Moosup, CT 06354, 3 beds, 1 bath

$265,000

3 beds1 bath1,000 sq ft

39 Sterling Hill Rd, Moosup, CT 06354

Property at 236 Deerfield Rd, Pomfret Center, CT 06259, 3 beds, 2.5 baths

$989,000

3 beds2.5 baths3,827 sq ft

236 Deerfield Rd, Pomfret Center, CT 06259

Property at 1530 Hartford Pike, East Killingly, CT 06243, 5 beds, 4 baths

$699,900

5 beds4 baths3,018 sq ft

1530 Hartford Pike, East Killingly, CT 06243

Property at 19 Cady St, Killingly, CT 06239, 3 beds, 2 baths

$250,000

3 beds2 baths1,200 sq ft

19 Cady St, Killingly, CT 06239

Property at 25 Provost Ln, Dayville, CT 06241, 3 beds, 1.5 baths

$469,900

3 beds1.5 baths1,597 sq ft

25 Provost Ln, Dayville, CT 06241

Property at 543 Lisbon Rd, Canterbury, CT 06331, 2 beds, 1 bath

$310,000

2 beds1 bath804 sq ft

543 Lisbon Rd, Canterbury, CT 06331

Property at 57 Wilkinson St, Putnam, CT 06260, 6 beds, 2 baths

$299,000

6 beds2 baths2,469 sq ft

57 Wilkinson St, Putnam, CT 06260

Property at 233 Fire Tower Rd, Pomfret Center, CT 06259, 4 beds, 2.5 baths

$799,900

4 beds2.5 baths2,982 sq ft

233 Fire Tower Rd, Pomfret Center, CT 06259

Property at 85 Robertson Ave, Killingly, CT 06239, 4 beds, 2 baths

$399,000

4 beds2 baths1,904 sq ft

85 Robertson Ave, Killingly, CT 06239

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Vintage Homes for Sale in Windham County

There are currently 89 vintage homes for sale in Windham County at a median listing price of $399K. 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 36 days and receive 1 offers. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 142 homes have been sold in Windham County. In addition to houses in Windham County, there were also 30 condos, 1 townhouse, and 40 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.

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