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

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OPEN SUN, 1PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Welcome to this charming and nicely updated 2-bedroom, 1.5-bath Cape Cod-style home, conveniently located just minutes from downtown New Milford! Offering a wonderful combination of classic character and modern conveniences, this home is move-in ready and has plenty to offer. Step inside to find hardwood floors throughout, a comfortable living room featuring a fireplace, and an updated kitchen with stainless steel appliances. Both bedrooms are generously sized, providing plenty of room for comfortable everyday living. Recent improvements include a central air conditioning system installed approximately five years ago. The home also features public water and solar panels at just $50 per mont

$399,000

2 beds1.5 baths1,197 sq ft

62 Park Lane Rd, New Milford, CT 06776

Updated kitchen • Hardwood floors • Fireplace

NEW 1 HR AGOFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Charming Colonial situated on a quiet, private street in North Canaan, just a short walk to town. Recently updated, this inviting home offers four bedrooms and 1.5 baths, blending classic character with modern improvements. Beautiful old hardwood floors run throughout, adding warmth and charm. Recent upgrades include all new windows, a new entryway, and spray foam insulation in the attic for improved energy efficiency. Outside, a level, private backyard provides a wonderful setting for outdoor entertaining, gardening, or simply relaxing. A lovely home in a convenient location, offering the perfect combination of classic New England charm and modern comfort.

$395,000

4 beds1 bath1,396 sq ft

41 Reed St, Canaan, CT 06018

Recent upgrades • Level backyard • Private street

OPEN SAT, 1PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Full of charm and character, this early 1900s Colonial offers a welcoming blend of classic style and everyday comfort. Featuring 3 bedrooms and 2 full bathrooms, this inviting home offers a warm and comfortable atmosphere throughout. The kitchen features beautiful wood cabinetry and stainless steel appliances, creating a timeless look with modern appeal. Outside, enjoy a cute yard with space to relax, garden, or entertain. With its charming character and appealing features, this delightful Colonial is ready to welcome its next owner and offers a wonderful opportunity to make it your own.

$310,000

3 beds2 baths1,373 sq ft

28 Eagle St, Terryville, CT 06786

Wood cabinetry • Cute yard • 6,969 sq ft lot

OPEN SAT, 12PM TO 2:30PM

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Step inside the welcoming foyer and discover this beautifully updated home featuring gleaming hardwood floors and a spacious, semi-open-concept main level. The inviting living room flows seamlessly into the dining area and eat-in kitchen, complete with stainless steel appliances and plenty of space for everyday living and entertaining. Just off the kitchen, you'll find an additional well-appointed living space, a versatile office or playroom, a full bathroom, and the convenience of main-level laundry. A stunning turned staircase leads to the second floor, where you'll find three generously sized bedrooms, including an exceptionally spacious primary bedroom with a large walk-in closet. The b

$400,000

3 beds2 baths1,582 sq ft

46 Central Ave, Oakville, CT 06779

Turned staircase • Main-level laundry • Large walk-in closet

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Opportunity awaits in the Terryville section of Plymouth! This versatile 2-family offers two bedrooms on each floor, a detached 2-car garage, and a . 26-acre lot. Both units feature their own front porches and vinyl-clad thermopane windows. Both units have been freshly painted! The first-floor and has oil heat, a brand-new 40-gallon electric hot water tank, and convenient washer/dryer hookups in the basement. Upstairs, the second-floor unit features an updated kitchen and bath, a fully applianced kitchen, in-unit washer/dryer hookups, electric heat, and a 6-year-old 40-gallon gas hot water tank. A walk-up, floored attic provides additional storage. With both units ready for new tenants or o

$309,900

4 beds2 baths1,560 sq ft

7 Schultz St, Terryville, CT 06786

Updated bath • Front porches • Updated kitchen

Property at 245 Riverside St, Oakville, CT 06779, 4 beds, 1.5 baths

$288,000

4 beds1.5 baths1,432 sq ft

245 Riverside St, Oakville, CT 06779

Property at 44 Straits Turnpike Ln, Morris, CT 06763, 2 beds, 1 bath

$399,999

2 beds1 bath1,175 sq ft

44 Straits Turnpike Ln, Morris, CT 06763

Property at 37 Foote Ave, Canaan, CT 06018, 3 beds, 2.5 baths

$489,900

3 beds2.5 baths2,276 sq ft

37 Foote Ave, Canaan, CT 06018

Property at 41 W Morris Rd, Bantam, CT 06750, 2 beds, 1 bath

$485,000

2 beds1 bath1,544 sq ft

41 W Morris Rd, Bantam, CT 06750

Property at 5 Hickory Ln, New Milford, CT 06776, 2 beds, 2 baths

$530,000

2 beds2 baths1,567 sq ft

5 Hickory Ln, New Milford, CT 06776

Property at 82 Porter St, Watertown, CT 06795, 3 beds, 1 bath

$284,999

3 beds1 bath1,248 sq ft

82 Porter St, Watertown, CT 06795

Property at 5-B Chase Hill Rd, Kent, CT 06757, 3 beds, 2 baths

$365,000

3 beds2 baths1,230 sq ft

5-B Chase Hill Rd, Kent, CT 06757

Property at 50 Kasson Ave, Bethlehem, CT 06751, 2 beds, 1.5 baths

$449,900

2 beds1.5 baths888 sq ft

50 Kasson Ave, Bethlehem, CT 06751

Property at 36 E Main St, Panama, NY 14767, 1.5 baths

$135,000

Studio1.5 baths5,360 sq ft

36 E Main St, Panama, NY 14767

Listing by Century 21 Turner Brokers, (716) 763-7506

Property at 75 Bruning Rd, New Hartford, CT 06057, 4 beds, 3 baths

$599,000

4 beds3 baths3,214 sq ft

75 Bruning Rd, New Hartford, CT 06057

Property at 194 Birge Park Rd, Harwinton, CT 06791, 2 beds, 1 bath

$359,900

2 beds1 bath1,229 sq ft

194 Birge Park Rd, Harwinton, CT 06791

Property at 59 Hill St, Torrington, CT 06790, 5 beds, 3 baths

$399,900

5 beds3 baths1,838 sq ft

59 Hill St, Torrington, CT 06790

Property at 815 Cheyenne Rd, Watertown, CT 06795, 2 beds, 1 bath

$189,900

2 beds1 bath680 sq ft

815 Cheyenne Rd, Watertown, CT 06795

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 737 Litchfield Tpke, New Hartford, CT 06057, 3 beds, 1 bath

$189,000

3 beds1 bath1,184 sq ft

737 Litchfield Tpke, New Hartford, CT 06057

Property at 738 North St, Goshen, CT 06756, 1 bed, 1 bath

$199,900

1 bed1 bath432 sq ft

738 North St, Goshen, CT 06756

Property at 290 Torrington Rd, Litchfield, CT 06759, 4 beds, 2 baths

$425,000

4 beds2 baths2,110 sq ft

290 Torrington Rd, Litchfield, CT 06759

Property at 49 Reed St, Canaan, CT 06018, 3 beds, 2 baths

$149,900

3 beds2 baths1,736 sq ft

49 Reed St, Canaan, CT 06018

Property at 11 Summit View Rd, Terryville, CT 06786, 2 beds, 1.5 baths

$289,900

2 beds1.5 baths1,030 sq ft

11 Summit View Rd, Terryville, CT 06786

Property at 92 Amenia Rd, Sharon, CT 06069, 3 beds, 2 baths

$425,000

3 beds2 baths1,502 sq ft

92 Amenia Rd, Sharon, CT 06069

Property at 42 Hardy St, Torrington, CT 06790, 3 beds, 1.5 baths

$219,000

3 beds1.5 baths1,512 sq ft

42 Hardy St, Torrington, CT 06790

Property at 35 Stanley Ave, Watertown, CT 06779, 3 beds, 1.5 baths

$319,900

3 beds1.5 baths1,442 sq ft

35 Stanley Ave, Watertown, CT 06779

Property at 11 Judson Ave, Woodbury, CT 06798, 3 beds, 1.5 baths

$529,000

3 beds1.5 baths2,120 sq ft

11 Judson Ave, Woodbury, CT 06798

Property at 60 Northside Dr, Torrington, CT 06790, 4 beds, 1.5 baths

$354,500

4 beds1.5 baths4,608 sq ft

60 Northside Dr, Torrington, CT 06790

Property at 15 Stone House Rd, Sharon, CT 06069, 3 beds, 2.5 baths

$2,350,000

3 beds2.5 baths4,182 sq ft

15 Stone House Rd, Sharon, CT 06069

Property at 20 N Sawyer Hill Rd, New Preston Marble Dale, CT 06777, 3 beds, 2 baths

$475,000

3 beds2 baths1,413 sq ft

20 N Sawyer Hill Rd, New Preston Marble Dale, CT 06777

Property at 651 High ST EXT, Thomaston, CT 06787, 4 beds, 1.5 baths

$329,900

4 beds1.5 baths1,909 sq ft

651 High ST EXT, Thomaston, CT 06787

Property at 207 Torringford West St, Torrington, CT 06790, 4 beds, 2 baths

$360,000

4 beds2 baths1,702 sq ft

207 Torringford West St, Torrington, CT 06790

Property at 130 Lake Dr, Bethlehem, CT 06751, 3 beds, 3 baths

$949,000

3 beds3 baths1,768 sq ft

130 Lake Dr, Bethlehem, CT 06751

Property at 139 Grantville Rd, Winsted, CT 06098, 5 beds, 4.5 baths

$950,000

5 beds4.5 baths4,212 sq ft

139 Grantville Rd, Winsted, CT 06098

Property at 65 W Shore Rd, New Preston Marble Dale, CT 06777, 3 beds, 2 baths

$1,995,000

3 beds2 baths2,475 sq ft

65 W Shore Rd, New Preston Marble Dale, CT 06777

Property at 2 Pomperaug Rd, Woodbury, CT 06798, 3 beds, 2.5 baths

$875,000

3 beds2.5 baths2,480 sq ft

2 Pomperaug Rd, Woodbury, CT 06798

Property at 16 Oak St, Terryville, CT 06786, 4 beds, 2 baths

$300,000

4 beds2 baths1,473 sq ft

16 Oak St, Terryville, CT 06786

Property at 218 Oak St, Winsted, CT 06098, 3 beds, 1 bath

$235,000

3 beds1 bath1,155 sq ft

218 Oak St, Winsted, CT 06098

Property at 326 West St, Morris, CT 06763, 3 beds, 1.5 baths

$449,900

3 beds1.5 baths1,320 sq ft

326 West St, Morris, CT 06763

Property at 1269 University Dr, Torrington, CT 06790, 2 beds, 1.5 baths

$207,000

2 beds1.5 baths1,648 sq ft

1269 University Dr, Torrington, CT 06790

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Based on information submitted to the MLS GRID as of Thu Oct 22 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 260 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 148 condos, 0 townhouses, and 58 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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