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

255 homes

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ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Welcome to this charming country cottage, surrounded by beautiful grounds filled with perennial gardens, flowering trees and delicious raspberry bushes. With Bethlehem Land Trust property bordering the rear and across the road, the setting offers a wonderful sense of peace, privacy and connection to nature. Inside, the home is warm and inviting, with a flexible first-floor bedroom currently enjoyed as a cozy TV room. The walkout lower level features a handsome fieldstone fireplace, laundry area, and highly efficient propane furnace and water heater. Outside, a two-story garage/barn has stood the test of time and, with a little TLC, offers plenty of possibilities. Sip your morning coffee or

$345,000

3 beds1 bath982 sq ft

25 Munger Ln, Bethlehem, CT 06751

Fieldstone fireplace • Country cottage • Perennial gardens

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Bring your design ideas to this classic shingle-sided home. With a fully functional interior, the main floor features an open kitchen-dining area with living room, fireplace and hardwood flooring. The side entrance has a dedicated area perfect for a mudroom to keep the main living space organized. The second level hosts two bedrooms with hardwood floors and a full bath with shower. The top level was previously used as the third bedroom and contains an extra large closet perfect for storage. There are dual entrances on the main level as well as a lower level walk out basement to the quaint and private back yard. A storage shed exists for your outdoor equipment or gardening supplies along wit

$235,000

3 beds1 bath1,155 sq ft

218 Oak St, Winsted, CT 06098

Dual entrances • Extra large closet • Private back yard

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Discover the possibilities! Nestled on two beautifully wooded acres, this three-bedroom two full bath home offers a peaceful, private setting with endless potential to make it your own. Inside, you'll find hardwood floors, a spacious kitchen, generously sized bedrooms, freshly painted and renovated bathrooms. A convenient first floor bedroom with a bathroom suite offers a variety of living needs. Step outside and enjoy the natural beauty that surrounds you. Take a peaceful stroll through your backyard to a picturesque rolling hill and create a path the brook through the woods. The property also features a greenhouse and out buildings with electricity for any potential animal needs or woodwo

$348,000

3 beds2 baths1,487 sq ft

2380 Newfield Rd, Torrington, CT 06790

Renovated bathrooms • Spacious kitchen • Wooded acres

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
A truly special find within close proximity to Bantam Lake! This charming 3-bedroom Ranch offers a unique opportunity to enjoy the best of country and lake living, situated on 3 acres of leased, preserved grounds from the White Memorial Foundation. Enjoy easy access to Bantam Lake for boating, swimming, and recreation. Inside, the home features gleaming hardwood floors, a large living room/dining room combo with a cozy fireplace and bay/bow window, and a screened porch overlooking the peaceful surroundings. Step outside to the expansive deck, perfect for entertaining, relaxing, or enjoying the natural beauty. Located directly across from approximately 600 acres of land trust with scenic tra

$449,900

3 beds1.5 baths1,320 sq ft

326 West St, Morris, CT 06763

Scenic trails • Screened porch • 3 acres

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Quintessential Lake House in the Desirable Candlewood Lake Club! This 4-bedroom, 3-full-bath ranch is perfectly sited on a corner lot and offers the opportunity to make this much-loved, multi-generational home your own. Step inside to a welcoming living room with fireplace and built-ins, eat-in kitchen, and dining room that opens to an expansive enclosed 3-season patio with a wall of sliders-perfect for gathering family and friends. The primary suite features a full en-suite bath, while a second bedroom also has its own full bath, plus two additional bedrooms. Enjoy peek-a-boo seasonal views of Candlewood Lake in the winter. Candlewood Lake Club offers an exceptional private lake lifestyle

$725,000

4 beds3 baths1,898 sq ft

9 Chimney Point Rd, New Milford, CT 06776

0.28 acre lot • Garage • Built 1953

Property at 34 Gaylord Rd, Gaylordsville, CT 06755, 3 beds, 2 baths

$319,000

3 beds2 baths1,896 sq ft

34 Gaylord Rd, Gaylordsville, CT 06755

Property at 16 Oak St, Terryville, CT 06786, 4 beds, 2 baths

$300,000

4 beds2 baths1,473 sq ft

16 Oak St, Terryville, CT 06786

Property at 75 Meadow St, Litchfield, CT 06759, 3 beds, 2.5 baths

$599,000

3 beds2.5 baths2,576 sq ft

75 Meadow St, Litchfield, CT 06759

Property at 28 Curtiss Hill Rd, Morris, CT 06763, 4 beds, 1.5 baths

$799,000

4 beds1.5 baths1,608 sq ft

28 Curtiss Hill Rd, Morris, CT 06763

Property at 399 Cornwall Bridge Rd, Sharon, CT 06069, 3 beds, 2 baths

$795,000

3 beds2 baths1,773 sq ft

399 Cornwall Bridge Rd, Sharon, CT 06069

Property at 48 Preston Ln, Salisbury, CT 06068, 2 beds, 2.5 baths

$699,000

2 beds2.5 baths1,508 sq ft

48 Preston Ln, Salisbury, CT 06068

Property at 36 Falls Ter, Watertown, CT 06779, 2 beds, 1 bath

$339,000

2 beds1 bath1,117 sq ft

36 Falls Ter, Watertown, CT 06779

Property at 196 Lake Plymouth Blvd, Plymouth, CT 06782, 1 bed, 2.5 baths

$525,000

1 bed2.5 baths1,536 sq ft

196 Lake Plymouth Blvd, Plymouth, CT 06782

Property at 10 Weekeepeemee Rd, Woodbury, CT 06798, 3 beds, 1.5 baths

$599,900

3 beds1.5 baths2,012 sq ft

10 Weekeepeemee Rd, Woodbury, CT 06798

Property at 35 Prospect St, Winsted, CT 06098, 3 beds, 1 bath

$239,900

3 beds1 bath1,201 sq ft

35 Prospect St, Winsted, CT 06098

Property at 59 Dalton St, Oakville, CT 06779, 3 beds, 2 baths

$325,000

3 beds2 baths1,201 sq ft

59 Dalton St, Oakville, CT 06779

Property at 50 Southbury Rd, Roxbury, CT 06783, 5 beds, 3 baths

$950,000

5 beds3 baths1,959 sq ft

50 Southbury Rd, Roxbury, CT 06783

Property at 22 Woodlawn Dr, Torrington, CT 06790, 3 beds, 1.5 baths

$379,900

3 beds1.5 baths1,859 sq ft

22 Woodlawn Dr, Torrington, CT 06790

Property at 28 Rock Cut Rd, Bridgewater, CT 06752, 4 beds, 2 baths

$649,000

4 beds2 baths1,976 sq ft

28 Rock Cut Rd, Bridgewater, CT 06752

Property at 259 Main St, Oakville, CT 06779, 3 beds, 2 baths

$359,900

3 beds2 baths1,380 sq ft

259 Main St, Oakville, CT 06779

Property at 86-90 West St, Litchfield, CT 06759, 7 beds, 6 baths

$1,245,000

7 beds6 baths3,289 sq ft

86-90 West St, Litchfield, CT 06759

Property at 804 Walnut Hill Rd, Thomaston, CT 06787, 6 beds, 1.5 baths

$299,900

6 beds1.5 baths1,728 sq ft

804 Walnut Hill Rd, Thomaston, CT 06787

Property at 63 Main St N, Woodbury, CT 06798, 4 beds, 2 baths

$849,900

4 beds2 baths2,662 sq ft

63 Main St N, Woodbury, CT 06798

Property at 36 Beach Dr, Harwinton, CT 06791, 2 beds, 1 bath

$450,000

2 beds1 bath1,000 sq ft

36 Beach Dr, Harwinton, CT 06791

Property at 26 Fern Dr, Torrington, CT 06790, 4 beds, 1.5 baths

$365,000

4 beds1.5 baths1,770 sq ft

26 Fern Dr, Torrington, CT 06790

Property at 83 Thomson Rd, Bethlehem, CT 06751, 5 beds, 2.5 baths

$1,995,000

5 beds2.5 baths3,971 sq ft

83 Thomson Rd, Bethlehem, CT 06751

Property at 66 Carroll Dr, Torrington, CT 06790, 3 beds, 2 baths

$369,900

3 beds2 baths1,506 sq ft

66 Carroll Dr, Torrington, CT 06790

Property at 130 Riverton Rd, Winsted, CT 06098, 3 beds, 2 baths

$415,000

3 beds2 baths1,430 sq ft

130 Riverton Rd, Winsted, CT 06098

Property at 325 Brick School Rd, Warren, CT 06754, 3 beds, 1 bath

$625,000

3 beds1 bath1,160 sq ft

325 Brick School Rd, Warren, CT 06754

Property at 175 Pleasant View Rd, Thomaston, CT 06787, 4 beds, 1.5 baths

$399,900

4 beds1.5 baths1,790 sq ft

175 Pleasant View Rd, Thomaston, CT 06787

Property at 391 Kent Cornwall Rd, Kent, CT 06757, 4 beds, 4 baths

$1,200,000

4 beds4 baths4,200 sq ft

391 Kent Cornwall Rd, Kent, CT 06757

Property at 2581 Litchfield Rd, Watertown, CT 06795, 2 beds, 1 bath

$549,000

2 beds1 bath962 sq ft

2581 Litchfield Rd, Watertown, CT 06795

Property at 115 River Rd, Washington Depot, CT 06794, 4 beds, 3.5 baths

$1,585,000

4 beds3.5 baths1,598 sq ft

115 River Rd, Washington Depot, CT 06794

Property at 656 Kent Rd, Gaylordsville, CT 06755, 3 beds, 2 baths

$599,900

3 beds2 baths2,792 sq ft

656 Kent Rd, Gaylordsville, CT 06755

Property at 53 Merrimac St, Watertown, CT 06779, 1 bed, 1 bath

$220,000

1 bed1 bath559 sq ft

53 Merrimac St, Watertown, CT 06779

Property at 24 Scuppo Rd, Woodbury, CT 06798, 6 beds, 3.5 baths

$749,900

6 beds3.5 baths5,815 sq ft

24 Scuppo Rd, Woodbury, CT 06798

Property at 63 W Mountain Rd, Washington Depot, CT 06793, 4 beds, 4.5 baths

$2,395,000

4 beds4.5 baths3,699 sq ft

63 W Mountain Rd, Washington Depot, CT 06793

Property at 47 Maple Ave, Norfolk, CT 06058, 3 beds, 2 baths

$545,000

3 beds2 baths1,744 sq ft

47 Maple Ave, Norfolk, CT 06058

Property at 64-64 Big Bear Hill Rd, New Milford, CT 06776, 6 beds, 8 baths

$8,250,000

6 beds8 baths8,457 sq ft

64-64 Big Bear Hill Rd, New Milford, CT 06776

Property at 118 Meadow St, Winsted, CT 06098, 3 beds, 2 baths

$260,000

3 beds2 baths1,652 sq ft

118 Meadow St, Winsted, CT 06098

Property at 33 Chestnut Grove Rd, Watertown, CT 06795, 4 beds, 2 baths

$389,900

4 beds2 baths1,499 sq ft

33 Chestnut Grove Rd, Watertown, CT 06795

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Based on information submitted to the MLS GRID as of Sat Oct 24 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Litchfield County

There are currently 255 vintage homes for sale in Litchfield County at a median listing price of $500K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Litchfield County stay on the market for 56 days and receive 1 offers. This map is refreshed with the newest listings in Litchfield County every 15 minutes.

In the past month, 209 homes have been sold in Litchfield County. In addition to houses in Litchfield County, there were also 148 condos, 0 townhouses, and 57 multi-family units for sale in Litchfield County last month. Find your dream home in Litchfield 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 Litchfield County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Litchfield County. If you're looking to sell your home in the Litchfield County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Litchfield 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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