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

211 homes

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ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Potential awaits at this stunning antique stone home. The property was formerly used as a bed & breakfast and a retirement home. Currently used as a boarding house. The original 1800's stone bldg has additions to form over 7500 sq feet of living space Three separate entrances with two staircases. The main section hosts 9 bedrooms with 6 full baths and 4 half baths which share a communal kitchen and dining room. There is an additional one bedroom apartment at the rear with a private entrance. See floor plans provided. Walk across the street to hike for miles in Steeprock's Macricostas Preserve. Walking distance to New Preston Village, the town beach at Lake Waramaug, and Averill Orchar

$695,000

13 beds9.5 baths7,501 sq ft

77 New Milford Tpke, New Preston, CT 06777

Private entrance • Antique stone home • Two staircases

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Welcome to 18 Tarlton Street, a simple and comfortable ranch home with two bedrooms, one full bathroom, and a partially finished basement that gives you extra space to work with. The layout is easy to love. Walk into the carpeted living room, with the first bedroom immediately to your left. The second bedroom sits just past the living room, and the kitchen is tucked to the side with plenty of cabinet space and room for a small table. You'll also find two porches off the house in the back, perfect spots for morning coffee. The partially finished basement offers additional space for hobbies, storage, or a small hangout area. Outside, the yard is a manageable size and features a detached one-c

$225,000

2 beds1 bath826 sq ft

18 Tarlton St, Torrington, CT 06790

Small shed • Two porches • 4,791 sq ft lot

OPEN TODAY, 1PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Beautifully renovated 1870 Colonial offering 1,172 sq. ft. of updated and functional living space. The home features hardwood floors in the living room and both bedrooms, adding warmth and durability throughout. A convenient first-floor bedroom provides flexibility, while the spacious primary bedroom is located on the second level. The kitchen has been completely refreshed with new flooring, skylights that bring in excellent natural light, an eat-in area, and all-new stainless steel appliances. The first-floor laundry room adds everyday convenience and includes a remodeled half bath. The full bathroom has also been fully updated with modern finishes. Fresh interior paint and all-new lightin

$230,000

2 beds1.5 baths1,172 sq ft

9 John St, Winsted, CT 06098

Updated kitchen • Hardwood floors • First floor bedroom

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Completely renovated with upscale design, smart upgrades, and genuine TLC. This 4 bed / 3 bath home feels brand new the moment you step inside. The open-concept first floor features all-new flooring, fresh paint, modern LED lighting, and a fully updated kitchen with new cabinets and appliances that tie the space together beautifully. Each of the three full bathrooms has been thoughtfully tiled and finished for a clean, elevated feel. All four bedrooms are upstairs, including a true primary suite with dual closets and a private, newly tiled en-suite bath. A full bath on each level adds convenience for guests and everyday living. Major improvements include: * New HVAC with central heat &a

$524,900

4 beds3 baths2,164 sq ft

160 Laurel Hill Rd, Torrington, CT 06790

0.78 acre lot • 4 parking spots • Built 1915

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Discover this beautifully maintained 3-bedroom, 1.5-bath Colonial set on a level one-acre lot less than two miles from town. This home has been thoughtfully updated over the years and is truly move-in ready. Enjoy a spacious living room and family room, each featuring a cozy fireplace-perfect for New England seasons. The updated kitchen offers modern appliances and a bright, comfortable workspace. Gleaming hardwood floors run throughout the home, adding warmth and character to every room. Step outside to the attractive fieldstone patio complete with a built-in barbecue, an ideal setting for outdoor dining and entertaining. This property has an impressive list of improvements, including a ne

$399,000

3 beds1.5 baths1,969 sq ft

208 Spencer Hill Rd, Winsted, CT 06098

New boiler • Fieldstone patio • Updated kitchen

Property at 157 Elm St, Winsted, CT 06098, 6 beds, 2.5 baths

$339,000

6 beds2.5 baths2,376 sq ft

157 Elm St, Winsted, CT 06098

Property at 50 Jewett Hill Rd, Sharon, CT 06069, 3 beds, 1.5 baths

$599,000

3 beds1.5 baths1,356 sq ft

50 Jewett Hill Rd, Sharon, CT 06069

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

$290,000

3 beds2 baths1,652 sq ft

118 Meadow St, Winsted, CT 06098

Property at 57 Osage Cir, Watertown, CT 06795, 3 beds, 1 bath

$375,000

3 beds1 bath1,104 sq ft

57 Osage Cir, Watertown, CT 06795

Property at 78 Kearney St, Terryville, CT 06786, 4 beds, 2 baths

$319,900

4 beds2 baths1,747 sq ft

78 Kearney St, Terryville, CT 06786

Property at 8 Bancroft St, Torrington, CT 06790, 4 beds, 2 baths

$329,900

4 beds2 baths1,430 sq ft

8 Bancroft St, Torrington, CT 06790

Property at 80 Baron Ln, Torrington, CT 06790, 4 beds, 1 bath

$350,000

4 beds1 bath1,315 sq ft

80 Baron Ln, Torrington, CT 06790

Property at 16 Tracy St, Thomaston, CT 06787, 5 beds, 1.5 baths

$349,900

5 beds1.5 baths1,600 sq ft

16 Tracy St, Thomaston, CT 06787

Property at 279 E Elm St, Torrington, CT 06790, 4 beds, 2 baths

$399,900

4 beds2 baths2,003 sq ft

279 E Elm St, Torrington, CT 06790

Property at 124 North St, Litchfield, CT 06759, 6 beds, 6 baths

$1,350,000

6 beds6 baths4,910 sq ft

124 North St, Litchfield, CT 06759

Property at 2 Chapel Hill Rd, New Milford, CT 06776, 3 beds, 1.5 baths

$380,000

3 beds1.5 baths1,036 sq ft

2 Chapel Hill Rd, New Milford, CT 06776

Property at 11 W Chestnut Hill Rd, Litchfield, CT 06759, 5 beds, 3.5 baths

$765,000

5 beds3.5 baths3,328 sq ft

11 W Chestnut Hill Rd, Litchfield, CT 06759

Property at 90 Spruce Dr, Torrington, CT 06790, 2 beds, 2.5 baths

$349,000

2 beds2.5 baths1,320 sq ft

90 Spruce Dr, Torrington, CT 06790

Property at 308 Skiff Mountain Rd, Kent, CT 06757, 3 beds, 3 baths

$1,250,000

3 beds3 baths3,296 sq ft

308 Skiff Mountain Rd, Kent, CT 06757

Property at 31 Main St, Northfield, CT 06778, 4 beds, 3 baths

$495,000

4 beds3 baths1,873 sq ft

31 Main St, Northfield, CT 06778

Property at 72 Jason Ave, Watertown, CT 06795, 3 beds, 2 baths

$269,900

3 beds2 baths1,560 sq ft

72 Jason Ave, Watertown, CT 06795

Property at 117 Cherry Ave, Watertown, CT 06795, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths1,552 sq ft

117 Cherry Ave, Watertown, CT 06795

Property at 187 Torringford St, Winsted, CT 06098, 4 beds, 1.5 baths

$429,000

4 beds1.5 baths2,365 sq ft

187 Torringford St, Winsted, CT 06098

Property at 21 Schroback Rd, Plymouth, CT 06782, 3 beds, 1.5 baths

$242,000

3 beds1.5 baths1,344 sq ft

21 Schroback Rd, Plymouth, CT 06782

Property at 43 Gaylord Rd, Gaylordsville, CT 06755, 4 beds, 4.5 baths

$810,000

4 beds4.5 baths3,808 sq ft

43 Gaylord Rd, Gaylordsville, CT 06755

Property at 471 Lime Rock Rd, Lakeville, CT 06039, 3 beds, 1.5 baths

$399,000

3 beds1.5 baths1,895 sq ft

471 Lime Rock Rd, Lakeville, CT 06039

Property at 37 E Cotton Hill Rd, New Hartford, CT 06057, 4 beds, 1 bath

$379,000

4 beds1 bath1,260 sq ft

37 E Cotton Hill Rd, New Hartford, CT 06057

Property at 99 Norway St, Oakville, CT 06779, 4 beds, 2 baths

$370,000

4 beds2 baths1,999 sq ft

99 Norway St, Oakville, CT 06779

Property at 85 Stedman Rd, New Hartford, CT 06057, 2 beds, 1 bath

$349,999

2 beds1 bath748 sq ft

85 Stedman Rd, New Hartford, CT 06057

Property at 114 Carmel Hill Rd N, Bethlehem, CT 06751, 3 beds, 2 baths

$799,900

3 beds2 baths2,430 sq ft

114 Carmel Hill Rd N, Bethlehem, CT 06751

Property at 23 Prospect Ave, Oakville, CT 06779, 3 beds, 1.5 baths

$379,900

3 beds1.5 baths1,456 sq ft

23 Prospect Ave, Oakville, CT 06779

Property at 72 Orchard Hill Rd, Harwinton, CT 06791, 4 beds

$460,000

4 beds— baths2,200 sq ft

72 Orchard Hill Rd, Harwinton, CT 06791

Property at 116 Albany St, Torrington, CT 06790, 3 beds, 1.5 baths

$295,000

3 beds1.5 baths1,165 sq ft

116 Albany St, Torrington, CT 06790

Property at 116 Bushnell Ave, Oakville, CT 06779, 3 beds, 1 bath

$255,000

3 beds1 bath1,080 sq ft

116 Bushnell Ave, Oakville, CT 06779

Property at 246 Ashley Falls Rd, Canaan, CT 06018, 4 beds, 2 baths

$369,000

4 beds2 baths2,214 sq ft

246 Ashley Falls Rd, Canaan, CT 06018

Property at 390 Main St, New Hartford, CT 06057, 5 beds, 1.5 baths

$479,999

5 beds1.5 baths2,782 sq ft

390 Main St, New Hartford, CT 06057

Property at 36 Flagg Hill Rd, Colebrook, CT 06021, 3 beds, 1 bath

$295,000

3 beds1 bath1,303 sq ft

36 Flagg Hill Rd, Colebrook, CT 06021

Property at 148 Danbury Quarter Rd, Winsted, CT 06098, 4 beds, 2 baths

$339,900

4 beds2 baths1,999 sq ft

148 Danbury Quarter Rd, Winsted, CT 06098

Property at 83 Jason Ave, Watertown, CT 06795, 3 beds, 1 bath

$379,900

3 beds1 bath1,422 sq ft

83 Jason Ave, Watertown, CT 06795

Property at 23 Echo Dr, New Milford, CT 06776, 4 beds, 2.5 baths

$3,900,000

4 beds2.5 baths2,073 sq ft

23 Echo Dr, New Milford, CT 06776

Property at 121 Culvert St, Torrington, CT 06790, 4 beds, 3 baths

$274,900

4 beds3 baths1,733 sq ft

121 Culvert St, Torrington, CT 06790

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Based on information submitted to the MLS GRID as of Sun Nov 30 2025. 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 211 vintage homes for sale in Litchfield County at a median listing price of $485K. 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 63 days and receive 3 offers. This map is refreshed with the newest listings in Litchfield County every 15 minutes.

In the past month, 215 homes have been sold in Litchfield County. In addition to houses in Litchfield County, there were also 130 condos, 0 townhouses, and 49 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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