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

179 homes

Sort:

Recommended

NEW 13 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Unbeatable Value in Prime Torrington! Don't miss this golden opportunity to own a beautifully maintained 4-bed, 2-bath Colonial in one of Torrington's most sought-after neighborhoods. Boasting an updated kitchen with elegant granite counters, timeless hardwood floors, a spacious 2-car garage, and a massive fenced yard perfect for entertaining, pets, or gardening - this home checks every box. Whether you're a growing family or someone looking for move-in-ready quality, this property offers unmatched space, charm, and convenience just minutes from downtown. This strategic price drop makes this home one of the best values on the market! Act Now! Schedule your private showing today before it's

$329,900

4 beds1.5 baths2,136 sq ft

37 Linden St, Torrington, CT 06790

Fenced yard • Move-in-ready • Updated kitchen

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Classic 1925 Colonial in Litchfield's Historic District Discover timeless elegance at 137 Old South Road, a well maintained 4-bedroom, 2.5-bath Colonial set on nearly three-quarters of an acre in Litchfield's coveted Historic District. Built in 1925, this 9-room, 2,702-square-foot home showcases the craftsmanship and charming period details that define classic New England architecture. Step inside to find well-proportioned living spaces that balance historic character with comfortable, everyday living with fireplace. Four generous bedrooms provide flexibility for family, guests, or a home office, while two and a half baths offer modern convenience. A finished 3rd floor completes this inter

$785,000

4 beds2.5 baths2,702 sq ft

137 Old South Rd, Litchfield, CT 06759

0.71 acre lot • 2 garage spots • Built 1925

NEW 20 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
2-story home at 349 Lake Plymouth Blvd, Plymouth, CT offering 2 bedrooms, 1 full bath, a spacious layout, and a basement for storage or future potential. Enjoy a nice backyard for relaxing and entertaining, plus peace of mind with a roof approx. 2 years old. Low HOA of about $300/year includes lake access, making it easy to enjoy Lake Plymouth living. Conveniently located near Lake Plymouth, Route 6, and I-84 with quick access to Bristol, Waterbury, and Hartford-area commuting, along with nearby shopping, dining, and outdoor recreation.

$199,900

2 beds1 bath950 sq ft

349 Lake Plymouth Blvd, Plymouth, CT 06782

2 story home • Nice backyard • Lake access

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Welcome to 368 Candlewood Lake Road North, a beautifully updated home in the heart of New Milford. This property features a newly renovated kitchen with modern finishes, new cabinetry, and sleek surfaces designed for both everyday living and entertaining. The bathrooms have also been tastefully renovated, offering fresh, contemporary style and comfort. Set in a desirable location near Candlewood Lake, this home combines recent updates with classic charm. Conveniently located close to local amenities, shopping, dining, and recreational opportunities, this is an excellent opportunity to own a move-in-ready property in one of New Milford's most sought-after areas. A must-see home offering styl

$469,900

3 beds2 baths1,152 sq ft

368 Candlewood Lake Rd N, New Milford, CT 06776

New cabinetry • 0.35 acre lot • Built 1960

OPEN SAT, 11AM TO 1PMVIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Welcome to 8 Gregory Drive, set in the peaceful Merryall area of New Milford-an enclave known for quiet roads, wooded surroundings, and nearby natural treasures like the Aspetuck River and Lander Pond, local nature habitats where wildlife and scenery are part of everyday life. It is the kind of setting that makes you truly love where you live. This Cape Cod home sits on a level, private 0.78-acre lot and offers comfort, flexibility, and room to grow, with 2,080 sq. ft. above grade plus 300 sq. ft. of finished lower-level space. Inside, the layout supports a variety of lifestyles. Two bedrooms on the main level-including the primary-offer everyday convenience, while two large, identical bedr

$569,000

4 beds2 baths2,380 sq ft

8 Gregory Dr, New Milford, CT 06776

Aspetuck river • Modern appliances • Level private lot

Property at 46 Eddy St, Watertown, CT 06779, 2 beds, 1 bath

$319,000

2 beds1 bath1,134 sq ft

46 Eddy St, Watertown, CT 06779

Property at 552 Twin Lakes Rd, Salisbury, CT 06068, 4 beds, 4 baths

$1,995,000

4 beds4 baths4,442 sq ft

552 Twin Lakes Rd, Salisbury, CT 06068

Property at 238 Barton St, Torrington, CT 06790, 3 beds, 2 baths

$349,900

3 beds2 baths1,575 sq ft

238 Barton St, Torrington, CT 06790

Property at 65 Weekeepeemee Rd, Bethlehem, CT 06751, 3 beds, 1 bath

$349,900

3 beds1 bath1,126 sq ft

65 Weekeepeemee Rd, Bethlehem, CT 06751

Property at 10 Hazel Plain Rd, Woodbury, CT 06798, 2 beds, 2 baths

$350,000

2 beds2 baths1,267 sq ft

10 Hazel Plain Rd, Woodbury, CT 06798

Property at 67 E Litchfield Rd S, Litchfield, CT 06759, 2 beds, 1 bath

$399,999

2 beds1 bath1,104 sq ft

67 E Litchfield Rd S, Litchfield, CT 06759

Property at 179 Greenridge Rd, Torrington, CT 06790, 5 beds, 2 baths

$285,000

5 beds2 baths1,818 sq ft

179 Greenridge Rd, Torrington, CT 06790

Property at 77 New Milford Tpke, New Preston, CT 06777, 13 beds, 9.5 baths

$695,000

13 beds9.5 baths7,501 sq ft

77 New Milford Tpke, New Preston, CT 06777

Property at 27 High St, New Hartford, CT 06057, 3 beds, 1 bath

$337,000

3 beds1 bath1,498 sq ft

27 High St, New Hartford, CT 06057

Property at 63 Ridge Rd, Terryville, CT 06786, 2 beds, 1.5 baths

$305,000

2 beds1.5 baths1,287 sq ft

63 Ridge Rd, Terryville, CT 06786

Property at 126 Straits Tpke, Watertown, CT 06795, 3 beds, 1.5 baths

$475,000

3 beds1.5 baths1,754 sq ft

126 Straits Tpke, Watertown, CT 06795

Property at 415 South St, Litchfield, CT 06759, 4 beds, 4.5 baths

$1,695,000

4 beds4.5 baths4,152 sq ft

415 South St, Litchfield, CT 06759

Property at 93 Greenwoods Rd E, Norfolk, CT 06058, 6 beds, 1.5 baths

$524,900

6 beds1.5 baths2,952 sq ft

93 Greenwoods Rd E, Norfolk, CT 06058

Property at 560 Torringford East St, Torrington, CT 06790, 3 beds, 1 bath

$349,900

3 beds1 bath1,231 sq ft

560 Torringford East St, Torrington, CT 06790

Property at 534 Smith Rd, Thomaston, CT 06787, 2 beds, 1.5 baths

$399,900

2 beds1.5 baths1,176 sq ft

534 Smith Rd, Thomaston, CT 06787

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 15 Sharon Valley Rd, Sharon, CT 06069, 4 beds, 2 baths

$420,000

4 beds2 baths1,930 sq ft

15 Sharon Valley Rd, Sharon, CT 06069

DUTCHESS COUNTRY REALTY INC. M

Property at 265 Lake Plymouth Blvd, Plymouth, CT 06782, 3 beds, 1 bath

$299,000

3 beds1 bath1,232 sq ft

265 Lake Plymouth Blvd, Plymouth, CT 06782

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

$470,000

4 beds3 baths1,873 sq ft

31 Main St, Northfield, CT 06778

Property at 93 Sunnyside Ave, Oakville, CT 06779, 3 beds, 2 baths

$389,900

3 beds2 baths1,680 sq ft

93 Sunnyside Ave, Oakville, CT 06779

Property at 216 Baker Rd, Roxbury, CT 06783, 4 beds, 2 baths

$699,900

4 beds2 baths2,008 sq ft

216 Baker Rd, Roxbury, CT 06783

Property at 35 James St, Torrington, CT 06790, 5 beds, 2 baths

$289,900

5 beds2 baths1,776 sq ft

35 James St, Torrington, CT 06790

Property at 6 Thomas Ln, New Milford, CT 06776, 4 beds, 1 bath

$385,000

4 beds1 bath1,310 sq ft

6 Thomas Ln, New Milford, CT 06776

Property at 25 Edward Ave, Watertown, CT 06795, 2 beds, 1 bath

$319,900

2 beds1 bath832 sq ft

25 Edward Ave, Watertown, CT 06795

Property at 9 John St, Winsted, CT 06098, 2 beds, 1.5 baths

$230,000

2 beds1.5 baths1,172 sq ft

9 John St, Winsted, CT 06098

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 160 Laurel Hill Rd, Torrington, CT 06790, 4 beds, 3 baths

$524,900

4 beds3 baths2,164 sq ft

160 Laurel Hill Rd, Torrington, CT 06790

Property at 1657 Weed Rd, Torrington, CT 06790, 3 beds, 2 baths

$499,000

3 beds2 baths2,604 sq ft

1657 Weed Rd, Torrington, CT 06790

Property at 398 Funston Ave, Torrington, CT 06790, 3 beds, 1.5 baths

$329,900

3 beds1.5 baths1,152 sq ft

398 Funston Ave, Torrington, CT 06790

Property at 19 Henry St, Oakville, CT 06779, 3 beds, 1.5 baths

$380,000

3 beds1.5 baths956 sq ft

19 Henry St, Oakville, CT 06779

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

$359,900

3 beds1.5 baths1,456 sq ft

23 Prospect Ave, Oakville, CT 06779

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

$360,000

3 beds2.5 baths1,552 sq ft

117 Cherry Ave, Watertown, CT 06795

Property at 54 Buckingham St, Oakville, CT 06779, 2 beds, 2 baths

$284,990

2 beds2 baths977 sq ft

54 Buckingham St, Oakville, CT 06779

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

$419,000

4 beds1.5 baths2,365 sq ft

187 Torringford St, Winsted, CT 06098

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

$339,900

5 beds1.5 baths1,600 sq ft

16 Tracy St, Thomaston, CT 06787

Viewing page 1 of 5

Based on information submitted to the MLS GRID as of Wed Dec 24 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 179 vintage homes for sale in Litchfield County at a median listing price of $475K. 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 74 days and receive 5 offers. This map is refreshed with the newest listings in Litchfield County every 15 minutes.

In the past month, 164 homes have been sold in Litchfield County. In addition to houses in Litchfield County, there were also 114 condos, 0 townhouses, and 52 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.

More real estate resources for Litchfield County, CT

Nearby Counties

Cities

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Litchfield County, CT

How to buy a house in Litchfield County, CT

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Connecticut

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.