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

262 homes

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ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Opportunity and flexibility come together at 95 Williams Street in Winsted. Offering approximately 2,887 square feet of living space, this spacious multi-family property is currently configured as two generously sized units with plenty of room both inside and out. Set on a uniquely large . 49-acre corner lot, the property offers an impressive amount of outdoor space and privacy-something rarely found with a multi-family home. The left-side unit features four bedrooms and two full baths, while the right-side unit offers three bedrooms and one full bath-providing a total of seven bedrooms and three full baths. Each unit also benefits from additional attic and basement storage, a feature that

$374,900

6 beds3 baths2,887 sq ft

95 Williams Ave, Winsted, CT 06098

Large corner lot • Outdoor space • 0.49 acre lot

FOR SALE BY OWNER

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Offered at $749,900, 344 Kent Road brings together a distinctive former-church residence, prominent Route 7 visibility, and a flexible three-level rear building on 1.49 acres. Zoned B-1 Restricted Business, with potential for additional business uses through applicable permits or rezoning, subject to Town of New Milford review and approval. The 1,948-square-foot main house has three bedrooms, two full baths, and a basement half bath. The primary suite is on the main floor; two additional bedrooms and the second full bath are upstairs. Features include central air, oil heat, a rear deck with sunken hot tub, and storage below the deck. The owner reports 1901 construction and a newer boiler an

$749,900

3 beds3 baths— sq ft

344 Kent Rd, New Milford, CT 06776

Route 7 visibility • 1.49 acres • Built 1901

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
New Price!!! Motivated Seller! Country Farmhouse, Turn the key condition. Affordable Living in Thomaston! Why rent or pay condo fees when you can own this charming, move-in ready home? Offering affordability, thoughtful updates, and a convenient location, this property is the perfect choice for first-time buyers, downsizers, or anyone looking for a low-maintenance lifestyle. Step inside to find a freshly repainted interior with a bright, new kitchen, welcoming feel, complemented by beautiful refinished oak and laminate flooring throughout. Recent updates include upgraded electrical service and economical natural gas heat, providing both comfort and efficiency. Outside, enjoy a large, usable

$279,900

2 beds1 bath1,062 sq ft

162 Bristol St, Thomaston, CT 06787

New kitchen • Natural gas heat • 0.37 acre lot

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Welcome to a truly special riverfront property where natural beauty, exceptional privacy, and country living come together. Nestled among mature trees and picturesque open pastures, this beautifully renovated home offers the perfect blend of rustic charm, peaceful privacy, and modern comfort. Originally custom-built in the 1940's, the home has been completely renovated and thoughtfully updated, with no expense spared. The property is an idyllic retreat for horse lovers, or anyone seeking a private country lifestyle surrounded by beauty. With its riverfront setting, wooded landscape, open pastures, and inviting country character, this is a rare opportunity to own a property that feels like a

$1,100,000

3 beds2 baths1,796 sq ft

159 Merryall Rd, New Milford, CT 06776

Riverfront property • Two barns • Tack room

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Set on prestigious Salmon Kill Road, this exceptional four-bedroom property blends refined luxury with the beauty and tranquility of its natural setting. With a seamless flow of indoor and outdoor living, this exceptional home pairs high-end finishes with an inviting sense of warmth throughout. The main level is designed for both everyday living and effortless entertaining, featuring a gracious living room with a fireplace, a comfortable family room with a woodstove, and a charming three-season porch that wraps around the eat-in kitchen. Abundant gathering spaces and a natural flow to the outdoors create an atmosphere that is both elevated and welcoming. The stunning primary suite is a priv

$3,175,000

4 beds3.5 baths3,072 sq ft

144 Salmon Kill Rd, Unknown City, CT 06068

Primary suite • Three-season porch • 3.31 acre lot

Property at 143 Holabird Ave, Winsted, CT 06098, 8 beds, 4.5 baths

$595,900

8 beds4.5 baths4,800 sq ft

143 Holabird Ave, Winsted, CT 06098

Property at 23 Cook St, Washington Depot, CT 06794, 3 beds, 3 baths

$925,000

3 beds3 baths1,602 sq ft

23 Cook St, Washington Depot, CT 06794

Property at 18 Hinckley Rd, New Preston Marble Dale, CT 06777, 3 beds, 2 baths

$469,900

3 beds2 baths1,800 sq ft

18 Hinckley Rd, New Preston Marble Dale, CT 06777

Property at 16-18 Laurel Way, Norfolk, CT 06098, 10 beds, 8 baths

$2,950,000

10 beds8 baths9,512 sq ft

16-18 Laurel Way, Norfolk, CT 06098

Property at 138 Amenia Rd, Sharon, CT 06069, 9 beds, 6.5 baths

$6,995,000

9 beds6.5 baths12,057 sq ft

138 Amenia Rd, Sharon, CT 06069

Property at 104 Cherniske Rd, New Milford, CT 06776, 2 beds, 1.5 baths

$675,000

2 beds1.5 baths1,236 sq ft

104 Cherniske Rd, New Milford, CT 06776

Property at 81 Green Hill Rd, Washington Depot, CT 06793, 4 beds, 4 baths

$2,300,000

4 beds4 baths4,269 sq ft

81 Green Hill Rd, Washington Depot, CT 06793

Property at 130 Sharon Mountain Rd, Sharon, CT 06069, 4 beds, 4 baths

$1,500,000

4 beds4 baths3,905 sq ft

130 Sharon Mountain Rd, Sharon, CT 06069

Property at 40 Ruffin Rd, Woodbury, CT 06798, 4 beds, 2.5 baths

$1,490,000

4 beds2.5 baths2,732 sq ft

40 Ruffin Rd, Woodbury, CT 06798

Property at 25 High St, Torrington, CT 06790, 4 beds, 2 baths

$339,000

4 beds2 baths2,395 sq ft

25 High St, Torrington, CT 06790

Property at 497 Cornwall Bridge Rd, Sharon, CT 06069, 3 beds, 2.5 baths

$694,999

3 beds2.5 baths1,861 sq ft

497 Cornwall Bridge Rd, Sharon, CT 06069

Property at 18 East St, Bethlehem, CT 06751, 4 beds, 2 baths

$995,000

4 beds2 baths3,418 sq ft

18 East St, Bethlehem, CT 06751

Property at 465 Lime Rock Rd, Lakeville, CT 06039, 2 beds, 2.5 baths

$485,000

2 beds2.5 baths1,996 sq ft

465 Lime Rock Rd, Lakeville, CT 06039

Property at 920 Main St S, Woodbury, CT 06798, 4 beds, 5 baths

$2,995,000

4 beds5 baths5,316 sq ft

920 Main St S, Woodbury, CT 06798

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

$895,000

4 beds2 baths3,088 sq ft

469 Platt Hill Rd, Winsted, CT 06098

Property at 108 New Litchfield St, Torrington, CT 06790, 3 beds, 2 baths

$349,900

3 beds2 baths1,610 sq ft

108 New Litchfield St, Torrington, CT 06790

Property at 547 Under Mountain Rd, Salisbury, CT 06068, 5 beds, 4.5 baths

$2,450,000

5 beds4.5 baths6,906 sq ft

547 Under Mountain Rd, Salisbury, CT 06068

Property at 30 Hollow Rd, Woodbury, CT 06798, 5 beds, 4.5 baths

$1,395,000

5 beds4.5 baths4,884 sq ft

30 Hollow Rd, Woodbury, CT 06798

Property at 287 W Main St, Canaan, CT 06018, 3 beds, 1 bath

$299,000

3 beds1 bath1,784 sq ft

287 W Main St, Canaan, CT 06018

Property at 48 Center St, Winsted, CT 06098, 4 beds, 2.5 baths

$325,000

4 beds2.5 baths2,257 sq ft

48 Center St, Winsted, CT 06098

Property at 70 Gay St, Sharon, CT 06069, 4 beds, 1.5 baths

$509,000

4 beds1.5 baths1,559 sq ft

70 Gay St, Sharon, CT 06069

Property at 8 Burnham St, Oakville, CT 06779, 10 beds, 7 baths

$1,149,000

10 beds7 baths3,360 sq ft

8 Burnham St, Oakville, CT 06779

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

$7,400,000

7 beds7 baths13,056 sq ft

19 Seherr Thoss Dr, Litchfield, CT 06759

Property at 99 King Hill Rd, Sharon, CT 06069, 2 beds, 1 bath

$585,000

2 beds1 bath1,150 sq ft

99 King Hill Rd, Sharon, CT 06069

Property at 119 W Wakefield Blvd, Winsted, CT 06098, 4 beds, 2 baths

$849,900

4 beds2 baths1,781 sq ft

119 W Wakefield Blvd, Winsted, CT 06098

Property at 71 Hospital Hill Rd, Sharon, CT 06069, 2 beds, 1 bath

$675,000

2 beds1 bath1,402 sq ft

71 Hospital Hill Rd, Sharon, CT 06069

Property at 310 Litchfield Rd, Norfolk, CT 06058, 6 beds, 5.5 baths

$6,650,000

6 beds5.5 baths6,766 sq ft

310 Litchfield Rd, Norfolk, CT 06058

Property at 8 Roosevelt Ave, Terryville, CT 06786, 4 beds, 2 baths

$295,000

4 beds2 baths1,936 sq ft

8 Roosevelt Ave, Terryville, CT 06786

Property at 35 Clinton St, Torrington, CT 06790, 6 beds, 2 baths

$419,000

6 beds2 baths2,215 sq ft

35 Clinton St, Torrington, CT 06790

Property at 99 High St, Winsted, CT 06098, 14 beds, 11 baths

$575,000

14 beds11 baths3,012 sq ft

99 High St, Winsted, CT 06098

Property at 321 Kent Cornwall Rd, Kent, CT 06757, 5 beds, 3.5 baths

$1,095,000

5 beds3.5 baths2,502 sq ft

321 Kent Cornwall Rd, Kent, CT 06757

Property at 57 Indian Trail Rd, New Milford, CT 06776, 4 beds, 4 baths

$4,850,000

4 beds4 baths6,236 sq ft

57 Indian Trail Rd, New Milford, CT 06776

Property at 335 Norfolk Rd, East Canaan, CT 06024, 3 beds, 2 baths

$279,000

3 beds2 baths2,004 sq ft

335 Norfolk Rd, East Canaan, CT 06024

Property at 1 Great Elm Dr, Sharon, CT 06069, 6 beds, 8 baths

$3,999,000

6 beds8 baths6,716 sq ft

1 Great Elm Dr, Sharon, CT 06069

Property at 31 Church Hill Rd, Washington Depot, CT 06794, 2 beds, 1.5 baths

$675,000

2 beds1.5 baths1,274 sq ft

31 Church Hill Rd, Washington Depot, CT 06794

Property at 35 Schoolhouse Rd, Roxbury, CT 06783, 4 beds, 4.5 baths

$3,250,000

4 beds4.5 baths4,456 sq ft

35 Schoolhouse Rd, Roxbury, CT 06783

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Based on information submitted to the MLS GRID as of Fri Nov 13 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 262 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 59 days and receive 2 offers. This map is refreshed with the newest listings in Litchfield County every 15 minutes.

In the past month, 188 homes have been sold in Litchfield County. In addition to houses in Litchfield County, there were also 142 condos, 0 townhouses, and 62 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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