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

247 homes

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COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
So much to offer!!! Enjoy convenient one level living with tons of extras!! This ranch style home is located on a level corner lot. The attractive exterior has been completely redone with siding and stone veneer, while an oversized attached two-car garage and additional 20'X25' workshop provide fantastic space for hobbies or additional storage. A screened in porch for early morning coffee or a good book. Rear patio is great for a BBQ, entertaining and relaxing. Inside you will find 3 bedrooms, 2 bathrooms and a fully finished basement for unique flexible space. Cozy living room with a fireplace and the kitchen and dining room have an open flow combination for easy entertaining. Mini split c

$375,000

3 beds2 baths2,616 sq ft

2 Lynn Ave, Terryville, CT 06786

Screened in porch • Level corner lot • One level living

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Completely renovated from top to bottom-this home has been thoughtfully redone with virtually nothing left untouched. Updates include a brand-new septic system, oil tank, heating system, plumbing, electrical service and panel, kitchen, bathrooms, well pump and tank, water heater, and windows. The roof is less than 10 years old, and the lawn has been freshly seeded and hayed for new grass to grow. All there is left to do is move in. All of this is completely private and tucked away, offering a peaceful setting surrounded by open land that cannot be developed, providing a rare sense of privacy, tranquility, and beautiful views. Despite the secluded feel, you're just minutes from major ameniti

$424,999

3 beds1.5 baths1,810 sq ft

1774 Bunker Hill Rd, Watertown, CT 06795

New plumbing • New kitchen • New septic system

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Historic little town of Bethlehem. An in town charmer just steps from the town green. Front row seats for the annual Christmas Town Festival and the 4th of July parade. Much admired, sunflower lined walkway in front of the house opens to the fenced yard w amazing perennials and seasonal festive decorating. This stewardship has taken this house to the next level w major improvements and upgrades. Beautiful bright and sunny new kitchen w a breakfast bar and a sitting area. A large wide hallway w leaded glass window encompass's a laundry room and leads to a first-floor primary BR. The living room and dining room have exposed beamed ceilings, brick fp and wide board flooring. Three good sized b

$595,000

5 beds3 baths2,272 sq ft

65 Main St S, Bethlehem, CT 06751

Fenced yard • Private decking • Mature landscaping

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Step back in time and experience the timeless character of this beautiful Colonial in Watertown, built in 1840. Ideally situated on a spacious corner lot. Rich with rustic charm and historic details, this unique home features original wood floors, generous living spaces, and several fireplaces that add warmth and character throughout. The large kitchen provides plenty of room for gathering and everyday living, while a cozy den with a pellet stove opens to a stunning sunroom featuring soaring ceilings, and an abundance of windows overlooking the expansive backyard. With three bedrooms plus dedicated office space, the home offers a flexible layout to suit a variety of needs. One of the bedroo

$439,000

4 beds2.5 baths2,415 sq ft

635 Northfield Rd, Watertown, CT 06795

Cozy den • Stunning sunroom • Original wood floors

OPEN SAT, 11AM TO 1PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Beyond stone entry gates, a long driveway leads to this 1958 midcentury home, set well back from the road on 7.11 acres in Bridgewater. Six fireplaces, exposed-beam ceilings, expansive windows and open living areas connect the interiors to long western views. The open-plan kitchen features a substantial soapstone preparation island with abundant storage, a full-size Viking refrigerator/freezer and a six-burner range with grill and plancha. A fireplace and adjoining breakfast area make it the natural center of the house. A separate dining room with fireplace and a light-filled living room with a built-in bar provide space for larger occasions. The main-level primary suite includes an office

$1,790,000

4 beds5 baths5,006 sq ft

267 Main St S, Bridgewater, CT 06752

Six fireplaces • Midcentury home • Seven acres

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 85 E Litchfield Rd, Litchfield, CT 06759, 4 beds, 2 baths

$449,000

4 beds2 baths1,790 sq ft

85 E Litchfield Rd, Litchfield, CT 06759

Property at 46 Jason Ave, Watertown, CT 06795, 3 beds, 1.5 baths

$350,000

3 beds1.5 baths1,340 sq ft

46 Jason Ave, Watertown, CT 06795

Property at 123 Old Litchfield Rd, Washington Depot, CT 06794, 3 beds, 2 baths

$865,000

3 beds2 baths2,221 sq ft

123 Old Litchfield Rd, Washington Depot, CT 06794

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

$2,495,000

3 beds2.5 baths2,174 sq ft

10 Perkins Rd, New Preston Marble Dale, CT 06777

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

$785,000

3 beds2 baths1,396 sq ft

16 River Rd, Sharon, CT 06069

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 1231 Bantam Rd, Bantam, CT 06750, 4 beds, 2.5 baths

$649,000

4 beds2.5 baths2,501 sq ft

1231 Bantam Rd, Bantam, CT 06750

Property at 32 Aspetuck Ave, New Milford, CT 06776, 5 beds, 2.5 baths

$825,000

5 beds2.5 baths2,822 sq ft

32 Aspetuck Ave, New Milford, CT 06776

Property at 1620 Guernseytown Rd, Watertown, CT 06795, 3 beds, 1.5 baths

$399,900

3 beds1.5 baths1,663 sq ft

1620 Guernseytown Rd, Watertown, CT 06795

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

$285,000

2 beds1.5 baths1,212 sq ft

11 Cottage Rd, Harwinton, CT 06791

Property at 286 North St, Watertown, CT 06795, 3 beds, 2 baths

$399,000

3 beds2 baths1,637 sq ft

286 North St, Watertown, CT 06795

Property at 229 Jackson St, Thomaston, CT 06787, 3 beds, 1 bath

$299,900

3 beds1 bath858 sq ft

229 Jackson St, Thomaston, CT 06787

Property at 144 Island Trl, Morris, CT 06763, 3 beds, 1.5 baths

$1,250,000

3 beds1.5 baths1,257 sq ft

144 Island Trl, Morris, CT 06763

Property at 280 High ST EXT, Thomaston, CT 06787, 3 beds, 1 bath

$259,000

3 beds1 bath874 sq ft

280 High ST EXT, Thomaston, CT 06787

Property at 497 Cornwall Bridge Rd, Sharon, CT 06069, 3 beds, 2.5 baths

$719,000

3 beds2.5 baths1,861 sq ft

497 Cornwall Bridge Rd, Sharon, CT 06069

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

$789,000

3 beds3 baths2,595 sq ft

16 Rhynus Rd, Sharon, CT 06069

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

$450,000

3 beds2 baths1,430 sq ft

130 Riverton Rd, Winsted, CT 06098

Property at 129 Atwood Rd, Thomaston, CT 06787, 3 beds, 1 bath

$350,000

3 beds1 bath1,178 sq ft

129 Atwood Rd, Thomaston, CT 06787

Property at 26 Weaver St, Torrington, CT 06790, 3 beds, 1.5 baths

$419,900

3 beds1.5 baths1,115 sq ft

26 Weaver St, Torrington, CT 06790

Property at 108 New Litchfield St, Torrington, CT 06790, 3 beds, 2 baths

$349,900

3 beds2 baths1,610 sq ft

108 New Litchfield St, Torrington, CT 06790

Property at 239 Johnson St, Torrington, CT 06790, 3 beds, 1 bath

$274,900

3 beds1 bath1,092 sq ft

239 Johnson St, Torrington, CT 06790

Property at 347 W Wakefield Blvd, Winsted, CT 06098, 2 beds, 1 bath

$289,000

2 beds1 bath596 sq ft

347 W Wakefield Blvd, Winsted, CT 06098

Property at 172 Red Mountain Ave, Torrington, CT 06790, 3 beds, 1.5 baths

$325,000

3 beds1.5 baths1,890 sq ft

172 Red Mountain Ave, Torrington, CT 06790

Property at 9 Steele Brook Rd, Watertown, CT 06795, 4 beds, 2 baths

$415,000

4 beds2 baths1,824 sq ft

9 Steele Brook Rd, Watertown, CT 06795

Property at 14 Cooper St, Torrington, CT 06790, 10 beds, 4 baths

$485,000

10 beds4 baths2,992 sq ft

14 Cooper St, Torrington, CT 06790

Property at 170 Dawes Ave, Torrington, CT 06790, 2 beds, 1 bath

$349,900

2 beds1 bath1,424 sq ft

170 Dawes Ave, Torrington, CT 06790

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

$499,000

4 beds2 baths3,300 sq ft

1318 Litchfield Tpke, New Hartford, CT 06057

Property at 28 Cotton Hill Rd, New Hartford, CT 06057, 4 beds, 2 baths

$280,000

4 beds2 baths1,704 sq ft

28 Cotton Hill Rd, New Hartford, CT 06057

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

$592,500

3 beds2 baths1,503 sq ft

17 Church Hill Rd, Washington Depot, CT 06794

Property at 385 Middle Road Tpke, Woodbury, CT 06798, 4 beds, 2.5 baths

$875,000

4 beds2.5 baths2,394 sq ft

385 Middle Road Tpke, Woodbury, CT 06798

Property at 1 Haviland Rd, New Milford, CT 06776, 1 bed, 1 bath

$259,000

1 bed1 bath579 sq ft

1 Haviland Rd, New Milford, CT 06776

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

$400,000

3 beds1 bath1,050 sq ft

6 Culvert City Rd, New Milford, CT 06776

Property at 32 W Park Rd, Plymouth, CT 06782, 1 bed, 1 bath

$150,000

1 bed1 bath921 sq ft

32 W Park Rd, Plymouth, CT 06782

Property at 58 Maple Ave, Norfolk, CT 06058, 4 beds, 3 baths

$625,000

4 beds3 baths2,653 sq ft

58 Maple Ave, Norfolk, CT 06058

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Based on information submitted to the MLS GRID as of Mon Sep 07 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 247 vintage homes for sale in Litchfield County at a median listing price of $499K. 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 57 days and receive 1 offers. This map is refreshed with the newest listings in Litchfield County every 15 minutes.

In the past month, 239 homes have been sold in Litchfield County. In addition to houses in Litchfield County, there were also 149 condos, 0 townhouses, and 53 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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