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

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ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Welcome to this move-in ready 3-bedroom, 2-bathroom home offering comfort, functionality, and value. Built in 1925, this charming conventional-style property spans 1,412 square feet and sits on a generous 17,424 sq ft lot. With 6 total rooms, the layout provides spacious living areas complemented by a full basement-perfect for storage or future expansion. The home is heated by efficient oil-fired baseboard heat. Constructed with a durable frame and finished with low-maintenance aluminum/vinyl siding, the exterior is completed by a classic gable roof with asphalt shingles. This property blends character with practicality in a well-maintained home.

$274,999

3 beds2 baths1,412 sq ft

148 Hillside Ave, Torrington, CT 06790

0.4 acre lot • Built 1925 • Listed 130 days

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Discreet Gates Lead to Totally Private 30+ Acre Waterfront Compound. Totally Renovated 3 Bedroom, 2.5 Bath House with Heated Pool & Lake Views. A Large Modern Kitchen with Vaulted Ceiling; Great Room with Fireplace. Impressive Main Level Primary Suite with Full Bath, Office & Sitting Room. 2 Separate Fully Equipped Guest Cottages are Set Arm's Distance from the Main House. New Sports Court. Separate 4-Car Garage. A Private Path Leads to Wonderful Lake Area with New Dock & Total Serenity.

$2,995,000

3 beds2.5 baths4,020 sq ft

409 Northrop St, Bridgewater, CT 06752

Large modern kitchen • Lake views • Vaulted ceiling

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Motivated Seller !!! A Wonderful Opportunity To Own This Large Multi-Use Commercial And Residential Property! Located In The Hamlet of Gaylordsville In New Milford CT. Beautiful Location That Has Access To The Housatonic River. Located On Kent Road That Has Direct Access To N. Y. & Neighboring CT Towns. This Property Also Has A Beautiful Scenic View & Is Very Private. A Wonderful Combination Of Residential & Retail! Charming 1 Bedroom With Full Kitchen & Bathroom That Has Rental Income Opportunities. This Apartment Has A Back Deck With A Beautiful View. This Beautiful Property Gives Any Business Owner Many Opportunities For Any Opportunities They Have. There Are Two E

$399,000

1 bed1.5 baths3,660 sq ft

696 Kent Rd, Gaylordsville, CT 06755

Two electric meters • Back deck • 0.33 acre lot

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Step into timeless elegance with this impeccably restored and beautifully partially furnished Queen Anne Shingle-style home, available for immediate occupancy. Located in one of Washington's most coveted neighborhoods, this historic gem is just a short walk to the Frederick Gunn School, the Mayflower Inn, and the charming shops and cafes of Washington Depot. Originally built in the 1880s and masterfully renovated from the studs up in 2021-2022, the home seamlessly blends period charm with modern luxury. Every detail has been thoughtfully considered, resulting in a warm and sophisticated living space designed for today's discerning buyer. The grounds offer both privacy and potential-there's

$1,299,000

4 beds3.5 baths3,901 sq ft

75 Green Hill Rd, Washington, CT 06793

Exceptional address • 0.65 acre lot • Garage

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Church for sale! Available to be used as a new denomination, or converted to a residence. Beautiful sanctuary complete with pews with more in balcony. It has several large meeting/class rooms and an office, with two restrooms. Could be converted into a very cool house! There is also a 2931 sf 3BR antique rectory house on the property, part of which has been rented as a residence and part of which has been used as office space. The residence part could use updates, or convert the entire building back to residential use. May be suitable for a home based business in R-40 zone. This is a listing where you need to see it to understand the property. Schedule your private showing right away! The

$750,000

— beds4 baths5,952 sq ft

685 Kent Rd, Gaylordsville, CT 06755

Two restrooms • Zoned residential • Large meeting rooms

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

$6,200,000

4 beds4 baths6,236 sq ft

57 Indian Trail Rd, New Milford, CT 06776

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 393 S Main St, Torrington, CT 06790, 6 beds, 3 baths

$298,900

6 beds3 baths2,600 sq ft

393 S Main St, Torrington, CT 06790

Property at 79 Hilltop Rd, Sharon, CT 06069, 6 beds, 5.5 baths

$3,995,000

6 beds5.5 baths6,121 sq ft

79 Hilltop Rd, Sharon, CT 06069

Property at 1 Old Middle Rd, New Milford, CT 06776, 2 beds, 1 bath

$650,000

2 beds1 bath1,056 sq ft

1 Old Middle Rd, New Milford, CT 06776

Property at 12 Popple Swamp Rd, Cornwall Bridge, CT 06754, 6 beds, 3 baths

$2,495,000

6 beds3 baths4,380 sq ft

12 Popple Swamp Rd, Cornwall Bridge, CT 06754

Property at 48 Preston Ln, Salisbury, CT 06068, 2 beds, 2.5 baths

$799,000

2 beds2.5 baths1,508 sq ft

48 Preston Ln, Salisbury, CT 06068

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 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 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 56 Sharon Rd, Lakeville, CT 06039, 5 beds, 2.5 baths

$1,995,000

5 beds2.5 baths3,425 sq ft

56 Sharon Rd, Lakeville, CT 06039

Property at 308 Main St, Lakeville, CT 06039, 2 beds, 2.5 baths

$995,000

2 beds2.5 baths4,773 sq ft

308 Main St, Lakeville, CT 06039

Property at 47 E Main St, Salisbury, CT 06068, 2 beds, 1 bath

$399,999

2 beds1 bath994 sq ft

47 E Main St, Salisbury, CT 06068

Property at 400 Gay St, Sharon, CT 06069, 4 beds, 1.5 baths

$1,200,000

4 beds1.5 baths1,536 sq ft

400 Gay St, Sharon, CT 06069

Property at 353A Hayden Hill Rd, Torrington, CT 06790, 3 beds, 1 bath

$29,900

3 beds1 bath945 sq ft

353A Hayden Hill Rd, Torrington, CT 06790

Property at 16 River Pl, Norfolk, CT 06058, 2 beds, 1 bath

$85,000

2 beds1 bath858 sq ft

16 River Pl, Norfolk, CT 06058

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 1 Great Elm Dr, Sharon, CT 06069, 8 beds, 8 baths

$3,999,000

8 beds8 baths8,072 sq ft

1 Great Elm Dr, Sharon, CT 06069

Property at 72 Clapboard Rd, Bridgewater, CT 06752, 4 beds, 2 baths

$649,900

4 beds2 baths2,412 sq ft

72 Clapboard Rd, Bridgewater, CT 06752

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 89 Route 7 S, Falls Village, CT 06031, 3 beds, 2 baths

$455,000

3 beds2 baths1,848 sq ft

89 Route 7 S, Falls Village, CT 06031

Property at 10 Sunny Ridge Rd, Washington, CT 06793, 7 beds, 7.5 baths

$3,195,000

7 beds7.5 baths15,000 sq ft

10 Sunny Ridge Rd, Washington, CT 06793

Property at 337 Main St S, Woodbury, CT 06798, 4 beds, 2.5 baths

$899,900

4 beds2.5 baths3,700 sq ft

337 Main St S, Woodbury, CT 06798

Property at 8 Mudgetown Rd, Sharon, CT 06069, 4 beds, 4.5 baths

$1,750,000

4 beds4.5 baths3,838 sq ft

8 Mudgetown 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 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 595 Town Hill Rd, New Hartford, CT 06057, 4 beds, 3 baths

$1,300,000

4 beds3 baths6,673 sq ft

595 Town Hill Rd, New Hartford, CT 06057

Property at 51 Ferry Bridge Rd, Washington, CT 06793, 5 beds, 5.5 baths

$5,595,000

5 beds5.5 baths9,165 sq ft

51 Ferry Bridge Rd, Washington, CT 06793

Property at 62 Railroad St, Falls Village, CT 06031, 3 beds, 2.5 baths

$625,000

3 beds2.5 baths2,463 sq ft

62 Railroad St, Falls Village, CT 06031

Property at 210 Doolittle Dr, Norfolk, CT 06058, 6 beds, 7.5 baths

$4,490,000

6 beds7.5 baths5,671 sq ft

210 Doolittle Dr, Norfolk, CT 06058

Property at 544 Litchfield Rd, Harwinton, CT 06791, 3 beds, 1.5 baths

$975,000

3 beds1.5 baths1,596 sq ft

544 Litchfield Rd, Harwinton, CT 06791

Property at Candlewood Mountain Rd, New Milford, CT 06776

$1,700,000

— beds— baths— sq ft

Candlewood Mountain Rd, New Milford, CT 06776

Property at 7 South St, Plymouth, CT 06782

$62,500

— beds— baths— sq ft

7 South St, Plymouth, CT 06782

Property at 82 Riverton Rd, Colebrook, CT 06021

$850,000

— beds— baths2,538 sq ft

82 Riverton Rd, Colebrook, CT 06021

Property at 294 Lime Rock Rd, Lakeville, CT 06039

$89,000

— beds— baths— sq ft

294 Lime Rock Rd, Lakeville, CT 06039

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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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