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

211 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Discover a low maintenance and hassle-free alternative to condo living with this easy-to-maintain, single-family home , perfect for investors, first-time buyers, or anyone seeking simplified living without the burden of HOA fees. Step inside to an efficient layout featuring brand-new WREN kitchen cabinets, granite countertops, a new gas stove, and a new refrigerator, offering a fresh and modern cooking space. The carpet (installed in 2024) has been well maintained, and the home includes a hot water heater installed in 2022 for added peace of mind. Recent major updates include a new roof installed in 2023 with a 15-year transferable warranty, providing long-term value and security. Outside,

$190,000

2 beds1.5 baths832 sq ft

8 Oak St, Winsted, CT 06098

Hot water heater • New refrigerator • New gas stove

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Newly finished kitchen, bath, bedrooms, floors, walls, and finishing touches. Two sheds in back are great for art, pottery, woodworking, your ideas will fill them. A lovely backyard and babbling stream behind inspires creatives in all mediums. Come see this finished home to live or rent out. The possibilities are endless.

$279,900

3 beds1 bath984 sq ft

81 Riverside St, Watertown, CT 06779

Finished kitchen • Lovely backyard • Babbling stream

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Enjoy true one-level living in this expansive ranch style home featuring a versatile walkout finished lower level perfect for a potential in-law setup. The main floor offers three generous bedrooms, a large living area with a fireplace, Kitchen, and plenty of natural light throughout. The lower level adds exceptional flexibility with two additional bedrooms, a full kitchen, a family room, and a second fireplace-ideal for extended family, guests, or multi-generational living. Step outside to a spacious backyard, .58 acres perfect for entertaining, gardening, or play. This home offers endless opportunities-bring your ideas and make it your own with updating and personal touches. Close proximi

$329,000

5 beds2.5 baths1,428 sq ft

136 Morro St, Oakville, CT 06779

0.54 acre lot • 2 garage spots • Built 1955

FOR SALE BY OWNER

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Country Living in this Charming Cape with Heated Garage and a private 1.66 acre lot. * New Roof * 2 Large Sheds * Outdoor Fire Place

$339,000

2 beds2 baths1,075 sq ft

17 Cottage Rd, Harwinton, CT 06791

Heated garage • Outdoor fire place • New roof

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Two-Family investment opportunity! Beautiful deck overlooking the Naugatuck River, semi-private backyard, one-car garage, and off-street parking. Both units feature 2-bedrooms. The first floor unit features efficient gas heat and hot water, and a gas range for cooking. The second floor unit features a gas range for cooking, gas hot water, and efficient heating and cooling with a ductless mini-split system. This unit also boasts an additional room that can be used as an office or craft area complete with sliding glass doors that provide access to a rear deck and scenic views of the Naugatuck River. Furthermore, the bedrooms for this unit are located on the third floor, away from living areas

$300,000

4 beds2 baths1,882 sq ft

23 Berry St, Torrington, CT 06790

Efficient gas heat • Sliding glass doors • 4,356 sq ft lot

Property at 28 Sunny Ridge Rd, Washington Depot, CT 06793, 6 beds, 4 baths

$1,845,000

6 beds4 baths4,219 sq ft

28 Sunny Ridge Rd, Washington Depot, CT 06793

Property at 277 Painter Hill Rd, Roxbury, CT 06783, 3 beds, 2.5 baths

$2,572,500

3 beds2.5 baths2,559 sq ft

277 Painter Hill Rd, Roxbury, CT 06783

Property at 48 Maud St, Torrington, CT 06790, 3 beds, 2 baths

$279,900

3 beds2 baths1,298 sq ft

48 Maud St, Torrington, CT 06790

Property at 67 Hillside Ave, Torrington, CT 06790, 2 beds, 1 bath

$189,900

2 beds1 bath928 sq ft

67 Hillside Ave, Torrington, CT 06790

Property at 116 Great Brook Rd, New Milford, CT 06776, 3 beds, 2 baths

$425,000

3 beds2 baths1,764 sq ft

116 Great Brook Rd, New Milford, CT 06776

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

$420,000

3 beds1.5 baths956 sq ft

19 Henry St, Oakville, CT 06779

Property at 38 Old Turnpike Rd, Bantam, CT 06750, 4 beds, 2.5 baths

$1,495,000

4 beds2.5 baths2,377 sq ft

38 Old Turnpike Rd, Bantam, CT 06750

Property at 49 South St, Washington Depot, CT 06793, 2 beds, 3.5 baths

$1,195,000

2 beds3.5 baths3,285 sq ft

49 South St, Washington Depot, CT 06793

Property at 27 Washington Ave, Torrington, CT 06790, 4 beds, 2 baths

$269,900

4 beds2 baths1,745 sq ft

27 Washington Ave, Torrington, CT 06790

Property at 8 Main St N, Bethlehem, CT 06751, 2 beds, 1.5 baths

$299,900

2 beds1.5 baths1,872 sq ft

8 Main St N, Bethlehem, CT 06751

Property at 16 Wood Ct, Terryville, CT 06786, 4 beds, 1 bath

$269,900

4 beds1 bath1,544 sq ft

16 Wood Ct, Terryville, CT 06786

Property at 211 Lyman Dr, Torrington, CT 06790, 3 beds, 2 baths

$345,000

3 beds2 baths2,000 sq ft

211 Lyman Dr, Torrington, CT 06790

Property at 130 N Elm St, Torrington, CT 06790, 9 beds, 3 baths

$349,900

9 beds3 baths2,482 sq ft

130 N Elm St, Torrington, CT 06790

Property at 41 Prospect St, Canaan, CT 06018, 3 beds, 2 baths

$235,000

3 beds2 baths1,332 sq ft

41 Prospect St, Canaan, CT 06018

Property at 56 Hillside Ave, Plymouth, CT 06782, 3 beds, 1 bath

$325,000

3 beds1 bath1,008 sq ft

56 Hillside Ave, Plymouth, CT 06782

Property at 30 Culvert St, Torrington, CT 06790, 6 beds, 4 baths

$530,000

6 beds4 baths5,650 sq ft

30 Culvert St, Torrington, CT 06790

Property at 2 Judd Hill Rd, Woodbury, CT 06798, 3 beds, 2 baths

$569,000

3 beds2 baths1,470 sq ft

2 Judd Hill Rd, Woodbury, CT 06798

Property at 15 Woodside Ln, Terryville, CT 06786, 5 beds, 3 baths

$380,000

5 beds3 baths1,896 sq ft

15 Woodside Ln, Terryville, CT 06786

Property at 684 Main St, Plymouth, CT 06782, 7 beds, 3 baths

$415,000

7 beds3 baths3,445 sq ft

684 Main St, Plymouth, CT 06782

Property at 287 Amenia Union Rd, Sharon, CT 06069, 3 beds, 1.5 baths

$765,000

3 beds1.5 baths1,596 sq ft

287 Amenia Union Rd, Sharon, CT 06069

Property at 7 Goldmine Rd, New Milford, CT 06776, 3 beds, 1 bath

$424,900

3 beds1 bath1,008 sq ft

7 Goldmine Rd, New Milford, CT 06776

Property at 612 Kent Rd, Gaylordsville, CT 06755, 3 beds, 1 bath

$269,000

3 beds1 bath1,180 sq ft

612 Kent Rd, Gaylordsville, CT 06755

Property at 227 Morro St, Oakville, CT 06779, 2 beds, 2 baths

$275,000

2 beds2 baths1,470 sq ft

227 Morro St, Oakville, CT 06779

Property at 11 Shantry Rd, Colebrook, CT 06021, 3 beds, 1.5 baths

$980,000

3 beds1.5 baths1,443 sq ft

11 Shantry Rd, Colebrook, CT 06021

Property at 49 Center St, Thomaston, CT 06787, 4 beds, 2.5 baths

$310,000

4 beds2.5 baths2,000 sq ft

49 Center St, Thomaston, CT 06787

Property at 118 Bannon St, Torrington, CT 06790, 3 beds, 1 bath

$255,000

3 beds1 bath928 sq ft

118 Bannon St, Torrington, CT 06790

Property at 24 Whittlesey Ave, New Milford, CT 06776, 5 beds, 1.5 baths

$525,000

5 beds1.5 baths2,192 sq ft

24 Whittlesey Ave, New Milford, CT 06776

Property at 58 Eggleston St, Torrington, CT 06790, 3 beds, 2 baths

$314,900

3 beds2 baths1,092 sq ft

58 Eggleston St, Torrington, CT 06790

Property at 528 Clearview Ave, Torrington, CT 06790, 1 bed, 1 bath

$170,000

1 bed1 bath735 sq ft

528 Clearview Ave, Torrington, CT 06790

Property at 143 Whitcomb Hill Rd, Cornwall Bridge, CT 06754, 3 beds, 2 baths

$795,000

3 beds2 baths1,951 sq ft

143 Whitcomb Hill Rd, Cornwall Bridge, CT 06754

Property at 9 Riverview Ct, New Milford, CT 06776, 2 beds, 1 bath

$295,000

2 beds1 bath1,269 sq ft

9 Riverview Ct, New Milford, CT 06776

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

$524,900

3 beds2 baths2,604 sq ft

1657 Weed Rd, Torrington, CT 06790

Property at 1 N Shore Rd, Warren, CT 06777, 4 beds, 2 baths

$699,000

4 beds2 baths2,261 sq ft

1 N Shore Rd, Warren, CT 06777

Property at 440 Platt Hill Rd, Winsted, CT 06098, 4 beds, 2.5 baths

$500,000

4 beds2.5 baths3,416 sq ft

440 Platt Hill Rd, Winsted, CT 06098

Property at 28 Trumbull St, Bantam, CT 06750, 1 bed, 1 bath

$175,000

1 bed1 bath697 sq ft

28 Trumbull St, Bantam, CT 06750

Property at 16 Gaylord Rd, Gaylordsville, CT 06755, 2 beds, 1 bath

$340,000

2 beds1 bath1,774 sq ft

16 Gaylord Rd, Gaylordsville, CT 06755

Viewing page 2 of 6

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.

More real estate resources for Litchfield County, CT

Cities

Nearby Counties

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.