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:
Prime Opportunity in the Heart of Downtown Lakeville/Salisbury. A rare chance to own a distinguished Federal-era residence, seamlessly transformed into a versatile commercial space while maintaining the possibility of restoring it to a stately private home. Nestled in the vibrant center of Lakeville, this property blends historic charm with endless potential. Brimming with timeless character, the building showcases soaring ceilings, elegant wood moldings, and classic architectural details throughout. The main level features eight spacious rooms, allowing for customized configurations, while a half bath and laundry room add functional convenience. Upstairs, the owner's private residence offe

$995,000

2 beds2.5 baths4,773 sq ft

308 Main St, Lakeville, CT 06039

Historic charm • Soaring ceilings • Eight spacious rooms

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ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Lake Access, 3+ acres, Inground Pool, and room for expansion! Tucked away on a private road with shared lake access to the serene waters of Lake Washinee, this custom one-level home with room for expansion, offers the perfect blend of natural beauty, thoughtful design, and modern comfort. Set on just over three wooded acres with a tranquil stream, the property offers privacy and peaceful surroundings in every direction. The original home was built in 1950. There was a complete renovation and additions to the home in 2003, enlarging the home significantly. Step inside to discover vaulted ceilings, hardwood floors, and skylights that flood the home with natural light. The spacious primary sui

$799,000

2 beds2.5 baths1,508 sq ft

48 Preston Ln, Salisbury, CT 06068

Three wooded acres • Tranquil stream • Shared lake access

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
This Cape Cod house has been updated throughout including a new roof, new propane furnace, new A/C, updated electrical, new windows, and new driveway. The two car attached garage has a pull down stairway to access the storage above. Inside the house there is fresh paint and new flooring throughout. The eat-in kitchen has new shaker cabinetry, granite countertops, stainless steel appliances, new lighting fixtures, and laundry closet. There is a separate dining room, and another room on the first floor with lots of potential, and the living room has a large bay window. There are 3 bedrooms upstairs, all with brand new carpeting. The full bath is also on the 2nd floor and has been completely u

$349,900

3 beds1.5 baths1,512 sq ft

260 Hayden Hill Rd, Torrington, CT 06790

New propane furnace • Updated electrical • New driveway

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
A rare and storied offering, the Colonel Dwight Wellington Pierce Farmstead is a distinguished circa 1830 Greek Revival residence listed on the State Registry of Historic Places. Perched on a rise with views of mountains, conserved land, and state forest, it blends heritage, natural beauty, and modern comfort. Spanning over 4,300 square feet, the main house features original moldings, wide-plank floors, and five working fireplaces. There are six bedrooms-one on the main floor with a full bath, and five upstairs. The primary suite includes a fireplace, radiant-heated limestone bath, and a large walk-in closet. The kitchen boasts exposed beams, custom cabinetry, soapstone countertops, and pre

$2,495,000

6 beds3 baths4,380 sq ft

12 Popple Swamp Rd, Cornwall Bridge, CT 06754

State forest • Original moldings • Views of mountains

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Beautifully Crafted 3 Bedroom Colonial Situated in a wonderful area of Thomaston. This home features 1300+ square feet of living space with 7 Rooms, 3 Bedrooms, 1 Bathroom, 1 Car garage ( 174 square feet ) & the unfinished basement ( 502 square feet ). All the schools are close by with Black Rock Elementary School ( PreK - 3 ) 1.7 miles, Thomaston Center School ( 4 - 6 ) 0.3 miles & Thomaston High School ( 7 - 12 ) 1.8 miles. You are within a few minutes drive to everything including 1 miles to all major shopping, D & D & restaurants, 0.8 miles to Route 8, 6.5 miles to I 84. The home is conveniently Located to nearby Library and Nystroms pond ( Enjoy Kayaking, Tennis

$259,900

3 beds1 bath1,377 sq ft

104 Judson St, Thomaston, CT 06787

4,791 sq ft lot • Garage • Built 1890

Property at 45 Hill Top Rd, Morris, CT 06763, 3 beds, 2 baths

$675,000

3 beds2 baths2,706 sq ft

45 Hill Top Rd, Morris, CT 06763

Property at 62 Big Bear Hill Rd, New Milford, CT 06776, 6 beds, 8 baths

$8,200,000

6 beds8 baths8,457 sq ft

62 Big Bear Hill Rd, New Milford, CT 06776

Property at 17 Marsh Pt, Morris, CT 06763, 1 bed, 0.5 baths

$548,788

1 bed0.5 baths624 sq ft

17 Marsh Pt, Morris, CT 06763

Property at 28 White Hollow Rd, Lakeville, CT 06039, 3 beds, 3 baths

$875,000

3 beds3 baths2,784 sq ft

28 White Hollow Rd, Lakeville, CT 06039

Property at 180 Norway St, Oakville, CT 06779, 3 beds, 2 baths

$289,900

3 beds2 baths1,971 sq ft

180 Norway St, Oakville, CT 06779

Property at 22 Park St, Thomaston, CT 06787, 4 beds, 3 baths

$389,900

4 beds3 baths1,629 sq ft

22 Park St, Thomaston, CT 06787

Property at 406 Wells Hill Rd, Lakeville, CT 06039, 6 beds, 6.5 baths

$8,875,000

6 beds6.5 baths8,334 sq ft

406 Wells Hill Rd, Lakeville, CT 06039

Property at 84 Roxbury Rd, Washington, CT 06793, 5 beds, 5.5 baths

$5,995,000

5 beds5.5 baths6,884 sq ft

84 Roxbury Rd, Washington, CT 06793

Property at 127 Old Goshen Rd, Norfolk, CT 06058, 7 beds, 6.5 baths

$2,900,000

7 beds6.5 baths4,824 sq ft

127 Old Goshen Rd, Norfolk, CT 06058

Property at 267 Main St, Salisbury, CT 06068, 4 beds, 3.5 baths

$995,000

4 beds3.5 baths3,167 sq ft

267 Main St, Salisbury, CT 06068

Property at 426 Torrington Rd, Litchfield, CT 06759, 2 beds, 1 bath

$440,000

2 beds1 bath1,030 sq ft

426 Torrington Rd, Litchfield, CT 06759

Houlihan Lawrence Inc.

Property at 424 Bantam Lake Rd, Morris, CT 06763, 4 beds, 3.5 baths

$1,400,000

4 beds3.5 baths2,226 sq ft

424 Bantam Lake Rd, Morris, CT 06763

Property at 312 Colebrook River Rd, Colebrook, CT 06021, 3 beds, 1 bath

$259,000

3 beds1 bath1,488 sq ft

312 Colebrook River Rd, Colebrook, CT 06021

Property at 55 Walnut St, Winsted, CT 06098, 5 beds, 2.5 baths

$499,999

5 beds2.5 baths5,016 sq ft

55 Walnut St, Winsted, CT 06098

Property at 279 Main St, Torrington, CT 06790, 3 beds, 1 bath

$269,900

3 beds1 bath1,697 sq ft

279 Main St, Torrington, CT 06790

Property at 7 Church St N, New Hartford, CT 06057, 4 beds, 2 baths

$349,900

4 beds2 baths2,248 sq ft

7 Church St N, New Hartford, CT 06057

Property at 50 Main St, Salisbury, CT 06039, 4 beds, 3.5 baths

$2,345,000

4 beds3.5 baths3,058 sq ft

50 Main St, Salisbury, CT 06039

Property at 182 Church St, Canaan, CT 06018, 3 beds, 1.5 baths

$300,000

3 beds1.5 baths1,232 sq ft

182 Church St, Canaan, CT 06018

Property at 148 Hillside Ave, Torrington, CT 06790, 3 beds, 2 baths

$274,999

3 beds2 baths1,412 sq ft

148 Hillside Ave, Torrington, CT 06790

Property at 163 Dublin Rd, Falls Village, CT 06031, 2 beds, 2 baths

$925,000

2 beds2 baths1,784 sq ft

163 Dublin Rd, Falls Village, CT 06031

Property at 54 Mountain Rd, Woodbury, CT 06798, 2 beds, 1 bath

$339,000

2 beds1 bath1,080 sq ft

54 Mountain Rd, Woodbury, CT 06798

Property at 159 Merryall Rd, New Milford, CT 06776, 3 beds, 2 baths

$1,250,000

3 beds2 baths1,796 sq ft

159 Merryall Rd, New Milford, CT 06776

Property at 110 Sharon Rd, Lakeville, CT 06039, 4 beds, 4 baths

$2,295,000

4 beds4 baths3,114 sq ft

110 Sharon Rd, Lakeville, CT 06039

Property at 482 Main St, Torrington, CT 06790, 16 beds, 12 baths

$1,245,000

16 beds12 baths11,399 sq ft

482 Main St, Torrington, CT 06790

Property at 212 Spencer Hill Rd, Winsted, CT 06098, 2 beds, 1.5 baths

$394,900

2 beds1.5 baths1,440 sq ft

212 Spencer Hill Rd, Winsted, CT 06098

Property at 469 Platt Hill Rd, Winsted, CT 06098, 4 beds, 2 baths

$920,000

4 beds2 baths3,088 sq ft

469 Platt Hill Rd, Winsted, CT 06098

Property at 19 Seherr Thoss Dr, Litchfield, CT 06759, 7 beds, 7 baths

$8,950,000

7 beds7 baths13,056 sq ft

19 Seherr Thoss Dr, Litchfield, CT 06759

Property at 231 Beechwood Ave, Torrington, CT 06790, 6 beds, 2.5 baths

$270,000

6 beds2.5 baths2,072 sq ft

231 Beechwood Ave, Torrington, CT 06790

Property at 354 Route 7 N, Falls Village, CT 06031, 4 beds, 3 baths

$1,350,000

4 beds3 baths4,025 sq ft

354 Route 7 N, Falls Village, CT 06031

Property at 74 Park Lane Rd, New Milford, CT 06776, 2 beds, 0.5 baths

$350,000

2 beds0.5 baths1,297 sq ft

74 Park Lane Rd, New Milford, CT 06776

Property at 11 Old Creamery Rd, Colebrook, CT 06021, 3 beds, 2 baths

$499,000

3 beds2 baths2,186 sq ft

11 Old Creamery Rd, Colebrook, CT 06021

Property at 45 Sunny Ridge Rd, Washington, CT 06793, 11 beds, 7.5 baths

$995,000

11 beds7.5 baths6,365 sq ft

45 Sunny Ridge Rd, Washington, CT 06793

Property at 39 Baron Ln, Torrington, CT 06790, 3 beds, 2.5 baths

$325,000

3 beds2.5 baths1,443 sq ft

39 Baron Ln, Torrington, CT 06790

Property at 21 Perry St, Lakeville, CT 06039, 3 beds, 3 baths

$1,045,000

3 beds3 baths2,113 sq ft

21 Perry St, Lakeville, CT 06039

Property at 685 Kent Rd, Gaylordsville, CT 06755, 4 baths

$750,000

— beds4 baths5,952 sq ft

685 Kent Rd, Gaylordsville, CT 06755

Property at 98 Island Trl, Morris, CT 06763, 5 beds, 3.5 baths

$2,200,000

5 beds3.5 baths3,498 sq ft

98 Island Trl, Morris, CT 06763

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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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