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

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ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases its original door with full exterior shutters, a hallmark of Greek Revival style. The living room centers on a classic fireplace, and along the upstairs landing a wall of built-in bookshelves creates a welcoming library space. Three bedrooms are located on the second floor, with an additional first-fl

$549,000

4 beds3 baths2,150 sq ft

101 Child Hill Rd, Woodstock, CT 06281

0.9 acre lot • Garage • Built 1830

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Fantastic 2 family with one side newly renovated. 3 bedrooms in each unit. Parking next to each unit and full basement.

$299,900

6 beds2 baths2,040 sq ft

983 Riverside Dr, North Grosvenordale, CT 06255

Full basement • 7,405 sq ft lot • Built 1889

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
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
Vintage Home for sale in Windham County, CT:
You may be eligible for $25,000 in down payment/closing cost assistance, forgivable over 10 years. Take advantage of a program that has limited funding left! Rather than paying someone else's mortgage pay yourself! Looking for low-maintenance living without sacrificing space or style? Look no further than The Junction House, a beautifully updated 8-unit condo community offering a peaceful lifestyle in a convenient Plainfield location. Unit 7 is located in the tan colored duplex on the front side of the building. This unit incorporates 3 beds, 1.5 baths in a townhome style format across three floors. The first floor exhibits an open concept dining and living space with both laundry and a hal

$249,900

3 beds1.5 baths1,259 sq ft

34 Pleasant St #7, Plainfield, CT 06374

Cabana • In ground pool • $410 HOA

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Welcome to 132 Grove Street in Putnam! This beautifully remodeled 3-bedroom home combines modern updates with classic charm. The property boasts a bright and inviting floor plan with stylish finishes throughout, featuring a fully updated kitchen equipped with new cabinetry, countertops, and appliances. The full bathroom has been tastefully renovated with sleek fixtures and contemporary design. Fresh paint, hardwood flooring, and thoughtful details make this home truly move-in ready. Outside, you'll find a spacious yard and a convenient 2-car garage. Perfectly located near downtown Putnam's shops, dining, and amenities, this property offers both comfort and convenience. Don't miss the chance

$340,900

3 beds1 bath1,344 sq ft

132 Grove St, Putnam, CT 06260

6,534 sq ft lot • 2 garage spots • Built 1929

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 48 Wrights Crossing Rd, Pomfret Center, CT 06259, 3 beds, 3 baths

$647,000

3 beds3 baths2,546 sq ft

48 Wrights Crossing Rd, Pomfret Center, CT 06259

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 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 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 414 Canterbury Rd, Brooklyn, CT 06234, 3 beds, 2 baths

$545,000

3 beds2 baths1,930 sq ft

414 Canterbury Rd, Brooklyn, CT 06234

Property at 34 Pleasant St #3, Plainfield, CT 06374, 2 beds, 1 bath

$219,500

2 beds1 bath1,188 sq ft

34 Pleasant St #3, Plainfield, CT 06374

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 60 Chaplin St, Chaplin, CT 06235, 3 beds, 2 baths

$425,000

3 beds2 baths2,438 sq ft

60 Chaplin St, Chaplin, CT 06235

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 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 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 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 38-82 Ballouville Rd, Dayville, CT 06241

$750,000

— beds— baths— sq ft

38-82 Ballouville Rd, Dayville, CT 06241

Property at 36 Plainfield Pike, Plainfield, CT 06374

$1,100,000

— beds— baths1,545 sq ft

36 Plainfield Pike, Plainfield, CT 06374

Property at 405 Providence Rd, Brooklyn, CT 06234

$799,500

— beds— baths1,764 sq ft

405 Providence Rd, Brooklyn, CT 06234

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Vintage Homes for Sale in Windham County

There are currently 62 vintage 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.

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