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

269 homes

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ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Beautiful Brick Eastside Ranch, Fully Fenced Yard Home features hardwood floors, tiled kitchen, 2-car garage, large basement for storage and possible future finishing, man cave, craft room or exercise room, 3 BR, 1.5 baths, and a beautiful inground pool for summer entertaining. Make this a place you will be proud to call home!

$379,900

3 beds1.5 baths1,859 sq ft

22 Woodlawn Dr, Torrington, CT 06790

Tiled kitchen • Large basement • Inground pool

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Impressive and spacious 5,815 sq. ft. well maintained residence with BRAND NEW ROOF and all new skylight windows(installed 8/15/26) offering exceptional one-level living with 6 bedrooms, 4 full bathrooms, and an oversized heated 3-car garage. A welcoming 12' x 9' slate-floor foyer introduces the home and leads to generously proportioned living spaces designed for both everyday comfort and entertaining. The oversized formal dining room provides an impressive setting for large gatherings, while the well-appointed kitchen features granite countertops, a casual eat-in area, double Viking ovens, a Viking 6-burner cooktop, and Miele dishwasher. Two fireplaces add warmth and character throughout t

$749,900

6 beds3.5 baths5,815 sq ft

24 Scuppo Rd, Woodbury, CT 06798

Slate floor foyer • Miele dishwasher • Granite countertops

OPEN SUN, 10AM TO 12PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
A Kent Landmark, Reimagined - This historic converted dairy barn offers 3,600 sq ft of flexible living space on over 14 private acres, with direct Housatonic River frontage and protected land trust borders. Hand-hewn beams, cathedral ceilings, and skylights carry the property's history throughout; while a converted silo houses a home office, art studio and gym. The sunny modern kitchen, renovated for large gatherings and generous entertaining, features an oversized island with seating, a commercial range, premium appliances, double sinks and dishwashers, and a wine cellar. The spacious dining area and lounge open to a landscaped patio overlooking a heated in-ground pool and cabana. Grounds

$1,200,000

4 beds4 baths4,200 sq ft

391 Kent Cornwall Rd, Kent, CT 06757

Hand-hewn beams • Converted dairy barn • Cathedral ceilings

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Motivated Seller! Create your dream home on 3.12 private acres with access to Lake Washinee (Twin Lakes). This 2-bedroom home offers a spacious primary suite with laundry, an inground pool, and a large covered deck overlooking the yard and pool. The septic is sized for 3 bedrooms, and the lower level offers plenty of room for expansion. A private-road setting and room to grow make this a true blank canvas with endless possibilities! All room sizes are approximate.

$699,000

2 beds2.5 baths1,508 sq ft

48 Preston Ln, Salisbury, CT 06068

Private acres • Inground pool • Large covered deck

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Tucked away at the terminus of a quiet dirt road with frontage on a stream, this 13-plus-acre sanctuary delivers absolute privacy alongside uncompromising mid century modern luxury. Approached via a winding scenic driveway, the property opens to reveal sweeping, recently opened panoramic vistas of Nettleton Hollow, complete with a tranquil brook and quintessential Litchfield County countryside. At the heart of the estate is a masterfully updated 1950s residence. Inside, striking vaulted ceilings elevate the freshly painted public spaces, and renovated hardwood floors, all anchored by a dramatic central fireplace with venetian plaster finish. Oversized plate-glass windows pull double duty, b

$2,395,000

4 beds4.5 baths3,699 sq ft

63 W Mountain Rd, Washington Depot, CT 06793

Panoramic vistas • Tranquil brook • Vaulted ceilings

Property at 115 River Rd, Washington Depot, CT 06794, 4 beds, 3.5 baths

$1,585,000

4 beds3.5 baths1,598 sq ft

115 River Rd, Washington Depot, CT 06794

Property at 2581 Litchfield Rd, Watertown, CT 06795, 2 beds, 1 bath

$549,000

2 beds1 bath962 sq ft

2581 Litchfield Rd, Watertown, CT 06795

Property at 42 Little Rd, Morris, CT 06763, 3 beds, 2 baths

$750,000

3 beds2 baths2,506 sq ft

42 Little Rd, Morris, CT 06763

Property at 59 Dalton St, Oakville, CT 06779, 3 beds, 2 baths

$325,000

3 beds2 baths1,201 sq ft

59 Dalton St, Oakville, CT 06779

Property at 53 Merrimac St, Watertown, CT 06779, 1 bed, 1 bath

$220,000

1 bed1 bath559 sq ft

53 Merrimac St, Watertown, CT 06779

Property at 63 Main St N, Woodbury, CT 06798, 4 beds, 2 baths

$849,900

4 beds2 baths2,662 sq ft

63 Main St N, Woodbury, CT 06798

Property at 64-64 Big Bear Hill Rd, New Milford, CT 06776, 6 beds, 8 baths

$8,250,000

6 beds8 baths8,457 sq ft

64-64 Big Bear Hill Rd, New Milford, CT 06776

Property at 368 Hamilton Ave, Watertown, CT 06795, 3 beds, 2 baths

$365,000

3 beds2 baths1,238 sq ft

368 Hamilton Ave, Watertown, CT 06795

Property at 118 Meadow St, Winsted, CT 06098, 3 beds, 2 baths

$260,000

3 beds2 baths1,652 sq ft

118 Meadow St, Winsted, CT 06098

Property at 34 Washington Ave, Torrington, CT 06790, 5 beds, 3 baths

$330,000

5 beds3 baths1,997 sq ft

34 Washington Ave, Torrington, CT 06790

Property at 36 Beach Dr, Harwinton, CT 06791, 2 beds, 1 bath

$450,000

2 beds1 bath1,000 sq ft

36 Beach Dr, Harwinton, CT 06791

Property at 303 Westside Ln, Torrington, CT 06790

$199,000

— beds— baths550 sq ft

303 Westside Ln, Torrington, CT 06790

Property at 50 Southbury Rd, Roxbury, CT 06783, 5 beds, 3 baths

$950,000

5 beds3 baths1,959 sq ft

50 Southbury Rd, Roxbury, CT 06783

Property at 33 Chestnut Grove Rd, Watertown, CT 06795, 4 beds, 2 baths

$389,900

4 beds2 baths1,499 sq ft

33 Chestnut Grove Rd, Watertown, CT 06795

Property at 130 Riverton Rd, Winsted, CT 06098, 3 beds, 2 baths

$415,000

3 beds2 baths1,430 sq ft

130 Riverton Rd, Winsted, CT 06098

Property at 16 River Rd, Sharon, CT 06069, 3 beds, 2 baths

$749,000

3 beds2 baths1,396 sq ft

16 River Rd, Sharon, CT 06069

Property at 67 E Litchfield Rd S, Litchfield, CT 06759, 3 beds, 1 bath

$300,000

3 beds1 bath1,104 sq ft

67 E Litchfield Rd S, Litchfield, CT 06759

Property at 94 North St, Plymouth, CT 06782, 4 beds, 2 baths

$575,000

4 beds2 baths1,848 sq ft

94 North St, Plymouth, CT 06782

Property at 325 Brick School Rd, Warren, CT 06754, 3 beds, 1 bath

$625,000

3 beds1 bath1,160 sq ft

325 Brick School Rd, Warren, CT 06754

Property at 205 Albert St, Torrington, CT 06790, 4 beds, 2.5 baths

$429,900

4 beds2.5 baths2,592 sq ft

205 Albert St, Torrington, CT 06790

Property at 155 Frederick St, Torrington, CT 06790, 2 beds, 1 bath

$279,900

2 beds1 bath1,257 sq ft

155 Frederick St, Torrington, CT 06790

Property at 656 Kent Rd, Gaylordsville, CT 06755, 3 beds, 2 baths

$599,900

3 beds2 baths2,792 sq ft

656 Kent Rd, Gaylordsville, CT 06755

Property at 360 West Side Rd, Goshen, CT 06756, 3 beds, 3.5 baths

$2,400,000

3 beds3.5 baths3,065 sq ft

360 West Side Rd, Goshen, CT 06756

Property at 90 Sage Rd, Woodbury, CT 06798, 4 beds, 4 baths

$1,100,000

4 beds4 baths3,968 sq ft

90 Sage Rd, Woodbury, CT 06798

Property at 136 Lower Rd, East Canaan, CT 06024, 3 beds, 2 baths

$575,000

3 beds2 baths1,496 sq ft

136 Lower Rd, East Canaan, CT 06024

Property at 47 Maple Ave, Norfolk, CT 06058, 3 beds, 2 baths

$545,000

3 beds2 baths1,744 sq ft

47 Maple Ave, Norfolk, CT 06058

Property at 50 Palmer Ave, Winsted, CT 06098, 3 beds, 2 baths

$429,000

3 beds2 baths1,680 sq ft

50 Palmer Ave, Winsted, CT 06098

Property at 519 Harwinton Ave, Torrington, CT 06790, 4 beds, 2 baths

$325,000

4 beds2 baths1,508 sq ft

519 Harwinton Ave, Torrington, CT 06790

Property at 22 Waller Rd, Gaylordsville, CT 06755, 4 beds, 2 baths

$399,000

4 beds2 baths2,358 sq ft

22 Waller Rd, Gaylordsville, CT 06755

Property at 17 Church Hill Rd, Washington Depot, CT 06794, 3 beds, 2 baths

$565,000

3 beds2 baths1,503 sq ft

17 Church Hill Rd, Washington Depot, CT 06794

Property at 573 Litchfield Rd, Harwinton, CT 06791, 5 beds, 2 baths

$375,000

5 beds2 baths1,504 sq ft

573 Litchfield Rd, Harwinton, CT 06791

Property at 32 Calkinstown Rd, Sharon, CT 06069, 3 beds, 2.5 baths

$650,000

3 beds2.5 baths1,248 sq ft

32 Calkinstown Rd, Sharon, CT 06069

Property at 110 Chestnut Land Rd, New Milford, CT 06776, 4 beds, 3.5 baths

$1,800,000

4 beds3.5 baths5,328 sq ft

110 Chestnut Land Rd, New Milford, CT 06776

Property at 4 Fall Mountain Ter, Terryville, CT 06786, 3 beds, 2 baths

$379,900

3 beds2 baths1,280 sq ft

4 Fall Mountain Ter, Terryville, CT 06786

Property at 171 South St, Litchfield, CT 06759, 4 beds, 3.5 baths

$2,395,000

4 beds3.5 baths4,346 sq ft

171 South St, Litchfield, CT 06759

Property at 144 Salmon Kill Rd, Unknown City, CT 06068, 4 beds, 3.5 baths

$3,175,000

4 beds3.5 baths3,072 sq ft

144 Salmon Kill Rd, Unknown City, CT 06068

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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 269 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.

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