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

270 homes

Sort:

Recommended

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Remarkable Pond-side Period Compound. A Meticulous c1777 Main House, re-built in 2023 with 3 Bed/2.5 Baths + Heated Pool + Finished Space Above 2-Car Barn + Shop. All Overlooking Bucolic Pond & Flowing Stream. This Jewel Commands 4+ Acres in 3 Separate Parcels on Both Sides of a Secondary Road Minutes to the Center of Bantam, Litchfield, Morris & Washington. An Open Kitchen with Fireplace Speaks to Breakfast Area. Separate Dining Room with Fireplace. Main Level Primary Bedroom with Full Bath & Views. Large Living Room with 2 Exposures Gleams in Natural Light. 2 Upper Bedrooms Share Full Bath. Separate 400+ Square Foot Shop or Office. Wonderful! Main House 1,575 Square Feet

$895,000

3 beds2.5 baths1,575 sq ft

38 Old Turnpike Rd, Bantam, CT 06750

Guest quarters • Separate dining room • Natural light

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Renegade Farm is a breathtaking 85+ acre luxury countryside estate where the romance of farm-to-table living meets the indulgence of a private resort. The sprawling grounds feature a beautifully appointed 4-bedroom main house(4,504 sq ft) & a completely separate, spacious 4-bedroom guest house(4,074 sq. ft) making it an unmatched haven for multi-generational gatherings and high-end entertaining. The Main house features a dreamy chef's kitchen with mountain views, wood-burning fireplaces in the living room and family room are among many of the home's special attributes. The guest house is almost identical in size to the main house and also boasts two wood-burning fireplaces-one in the

$5,375,000

4 beds3 baths4,504 sq ft

55-57 Brinton Hill Rd, Salisbury, CT 06031

Custom gunite pool • 85 acre estate • Chef's kitchen

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Set on 1.62 acres in Bantam, 1231 Bantam Road is a Cape Cod style home offering a flexible layout with 2,501 sq ft, 4 bedrooms and 2.5 baths. The home opens into a generous front room, offering flexible use as a sitting area or welcoming foyer, with an elegant dining room to the right and an inviting kitchen featuring an island, abundant cabinetry, farmhouse sink and granite counters. A stone patio sits just outside the back kitchen door, adding an easy outdoor connection. The foyer/sitting area also connects to a convenient half bathroom. The family room has a large bay window, and the formal living room offers a wet bar, working fireplace and large doors to a spacious wraparound deck that

$649,000

4 beds2.5 baths2,501 sq ft

1231 Bantam Rd, Bantam, CT 06750

Inviting kitchen • Cape cod style home • Generous front room

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Escape to the quiet elegance of Cobble Hill Farm, a 12.96-acre Greek Revival estate that perfectly balances 19th-century soul with modern luxury. Available for the first time in over 48 years, this mint condition historic gem features sun-drenched rooms, original wide-board floors, and four stately fireplaces. While the period character is meticulously preserved, the home is designed for today's comfort with a recently renovated kitchen, family room, and primary suite, plus central air in the east wing. This is the ultimate sanctuary for the modern homesteader, offering endless potential for an organic farm, vineyard, or equestrian facility. The property boasts a 1,950 sq. ft. vintage barn

$1,100,000

5 beds4.5 baths3,640 sq ft

127 Steele Rd, New Hartford, CT 06057

Greek revival estate • Spring-fed pond • Creative studio

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

Property at 10 Perkins Rd, New Preston Marble Dale, CT 06777, 3 beds, 2.5 baths

$2,295,000

3 beds2.5 baths2,174 sq ft

10 Perkins Rd, New Preston Marble Dale, CT 06777

Property at 11 Cottage Rd, Harwinton, CT 06791, 2 beds, 1.5 baths

$250,000

2 beds1.5 baths1,212 sq ft

11 Cottage Rd, Harwinton, CT 06791

Property at 65 Main St S, Bethlehem, CT 06751, 5 beds, 3 baths

$575,000

5 beds3 baths2,272 sq ft

65 Main St S, Bethlehem, CT 06751

Property at 101 Culvert St, Torrington, CT 06790, 7 beds, 2 baths

$349,900

7 beds2 baths2,200 sq ft

101 Culvert St, Torrington, CT 06790

Property at 537 Prospect St, Torrington, CT 06790, 5 beds, 2.5 baths

$339,000

5 beds2.5 baths3,440 sq ft

537 Prospect St, Torrington, CT 06790

Property at 59 Painter Ridge Rd, Washington, CT 06793, 5 beds, 3.5 baths

$2,895,000

5 beds3.5 baths3,844 sq ft

59 Painter Ridge Rd, Washington, CT 06793

Property at 125 S Canaan Rd, Canaan, CT 06018, 3 beds, 2.5 baths

$469,000

3 beds2.5 baths1,720 sq ft

125 S Canaan Rd, Canaan, CT 06018

Property at 70 Bee Brook Rd, Washington Depot, CT 06794, 3 beds, 3 baths

$349,900

3 beds3 baths1,379 sq ft

70 Bee Brook Rd, Washington Depot, CT 06794

Property at 47 Academy Hl, Watertown, CT 06795, 6 beds, 6.5 baths

$849,900

6 beds6.5 baths3,740 sq ft

47 Academy Hl, Watertown, CT 06795

Property at 1318 Litchfield Tpke, New Hartford, CT 06057, 4 beds, 2 baths

$449,000

4 beds2 baths3,300 sq ft

1318 Litchfield Tpke, New Hartford, CT 06057

Property at 72 Bee Brook Rd, Washington Depot, CT 06794, 3 beds, 2 baths

$284,900

3 beds2 baths1,372 sq ft

72 Bee Brook Rd, Washington Depot, CT 06794

Property at 95 Williams Ave, Winsted, CT 06098, 6 beds, 3 baths

$374,900

6 beds3 baths2,887 sq ft

95 Williams Ave, Winsted, CT 06098

Property at 82 Nova Scotia Hill Rd, Watertown, CT 06795, 5 beds, 3.5 baths

$665,000

5 beds3.5 baths2,890 sq ft

82 Nova Scotia Hill Rd, Watertown, CT 06795

Property at 11 Route 7 N, Falls Village, CT 06031, 3 beds, 2.5 baths

$595,000

3 beds2.5 baths2,069 sq ft

11 Route 7 N, Falls Village, CT 06031

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 1217 Main St N, Woodbury, CT 06798, 3 beds, 1.5 baths

$699,900

3 beds1.5 baths1,960 sq ft

1217 Main St N, Woodbury, CT 06798

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 68 Frances St, Oakville, CT 06779, 3 beds, 2 baths

$298,000

3 beds2 baths1,354 sq ft

68 Frances St, Oakville, CT 06779

Property at 126 Main St N, Woodbury, CT 06798, 4 beds, 1.5 baths

$649,900

4 beds1.5 baths1,872 sq ft

126 Main St N, Woodbury, CT 06798

Property at 114 Oliver St, Torrington, CT 06790, 3 beds, 2 baths

$359,900

3 beds2 baths1,837 sq ft

114 Oliver St, Torrington, CT 06790

Property at 71 Wildwood Rd, Torrington, CT 06790, 3 beds, 1 bath

$329,000

3 beds1 bath1,436 sq ft

71 Wildwood Rd, Torrington, CT 06790

Property at 344 Kent Rd, New Milford, CT 06776, 3 beds, 3 baths

$749,900

3 beds3 baths— sq ft

344 Kent Rd, New Milford, CT 06776

Property at 162 Hutchinson & Mike Road Pkwy, Litchfield, CT 06759, 5 beds, 4.5 baths

$2,500,000

5 beds4.5 baths4,145 sq ft

162 Hutchinson & Mike Road Pkwy, Litchfield, CT 06759

Property at 1917 Main St N, Woodbury, CT 06798, 4 beds, 2 baths

$780,000

4 beds2 baths4,819 sq ft

1917 Main St N, Woodbury, CT 06798

Property at 54 Lime Rock STTN, Falls Village, CT 06031, 3 beds, 2.5 baths

$985,000

3 beds2.5 baths2,461 sq ft

54 Lime Rock STTN, Falls Village, CT 06031

Property at 221 Segar Mountain Rd, Kent, CT 06757, 4 beds, 3 baths

$915,000

4 beds3 baths2,380 sq ft

221 Segar Mountain Rd, Kent, CT 06757

Property at 17 Hawthorne Ter, Torrington, CT 06790, 4 beds, 2 baths

$220,000

4 beds2 baths1,894 sq ft

17 Hawthorne Ter, Torrington, CT 06790

Property at 10 North St, Norfolk, CT 06058, 5 beds, 2.5 baths

$399,000

5 beds2.5 baths3,523 sq ft

10 North St, Norfolk, CT 06058

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 6 Culvert City Rd, New Milford, CT 06776, 3 beds, 1 bath

$399,000

3 beds1 bath1,050 sq ft

6 Culvert City Rd, New Milford, CT 06776

Property at 509 Weekeepeemee Rd, Woodbury, CT 06798, 3 beds, 2.5 baths

$1,278,000

3 beds2.5 baths2,346 sq ft

509 Weekeepeemee Rd, Woodbury, CT 06798

Property at 108 Squire Hill Rd, New Milford, CT 06776, 3 beds, 3 baths

$1,399,000

3 beds3 baths4,099 sq ft

108 Squire Hill Rd, New Milford, CT 06776

Property at 67 N Main St, Kent, CT 06757, 4 beds, 2.5 baths

$1,195,000

4 beds2.5 baths4,869 sq ft

67 N Main St, Kent, CT 06757

Property at 16 Rhynus Rd, Sharon, CT 06069, 3 beds, 3 baths

$749,000

3 beds3 baths2,595 sq ft

16 Rhynus Rd, Sharon, CT 06069

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 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

Viewing page 4 of 7

Based on information submitted to the MLS GRID as of Mon Nov 02 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 270 vintage homes for sale in Litchfield County at a median listing price of $500K. 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 56 days and receive 1 offers. This map is refreshed with the newest listings in Litchfield County every 15 minutes.

In the past month, 209 homes have been sold in Litchfield County. In addition to houses in Litchfield County, there were also 147 condos, 0 townhouses, and 57 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

5 Redfin agents serving Litchfield County

131

Deals*

4.5

Satisfaction

448

Homes closed*

* Data from the last year

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

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.