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:
Full of potential and freedom. At this price it is cheaper than renting - do the math! Perfect for In home office right on Main ST - Hang your sign, enjoy the tax write off, convenient access, save on brick & mortar rent. Can use private entrance to LL family room. The Family room has sliders to new decking w built-in benches, and pretty, private back yard. Propane line ready for a ventless gas FP, make this your cozy hang out/office or primary suite (potential to convert 1/2 bath laundry rm into full bath)? Living room and dining room have hard wood flooring. Kitchen had been remodeled w vaulted ceiling, skylights and island. Two upstairs bedrooms are not large but once slept 4! Sip

$299,900

2 beds1.5 baths1,872 sq ft

8 Main St N, Bethlehem, CT 06751

New decking • Private back yard • Private entrance

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Charm and modern comfort come together in this beautifully renovated 3BR, 2BA home set on nearly an acre along a quiet country road in Woodbury. The inviting main level features a cozy living room with a fireplace, a spacious first-floor bedroom, and a full bath-perfect for guests or one-level living. A newly updated kitchen opens to the dining area and leads directly to a brand-new deck overlooking a private, level backyard with distant pond and mountain views. The yard has been cleared, seeded, and extends to a peaceful meadow that backs to a wooded preserve. The recent expansion includes an oversized two-car garage, extra deep with high ceilings offering loft or workshop potential. The f

$569,000

3 beds2 baths1,470 sq ft

2 Judd Hill Rd, Woodbury, CT 06798

Brand new deck • Distant pond views • Renovated home

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Distinctive Country Estate with Two Homes on 9.6 Rolling Acres Set amid 9.6 picturesque country acres, this unique property offers two homes and endless potential. The stone and stucco main residence features eight spacious rooms, including four bedrooms and four fireplaces, blending classic character with old-world charm. Rolling open land and mature trees surround the home, providing an ideal setting for a private country retreat, family compound, or restoration project. The detached 843 sq. ft. , two-story guest house adds exceptional versatility-perfect for extended family, rental income, or a studio/workshop. P Restoration to the main house would include a new heating system, bathroo

$500,000

4 beds2.5 baths3,416 sq ft

440 Platt Hill Rd, Winsted, CT 06098

Rolling acres • Two homes • Bathroom updates

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Set on nearly an acre of land along scenic Amenia Road, this beautifully renovated 3-bedroom, 1.5-bathroom home blends classic charm with sophisticated updates. Located just minutes from the village center of Sharon, CT, the home offers a peaceful lifestyle in the heart of Litchfield County. Step inside to a warm, inviting living room featuring a wood-burning fireplace - ideal for cozy evenings. The kitchen is a dream for any home chef, boasting butcher block countertops, Italian Marazzi Rice Tile, and sleek, modern finishes. Design-forward touches include solid unlacquered brass hardware from Rejuvenation, and Schumacher fabric-covered walls that add elegant texture to the entryway and sta

$765,000

3 beds1.5 baths1,596 sq ft

287 Amenia Union Rd, Sharon, CT 06069

0.9 acre lot • Garage • Built 1800

ABOUT THIS HOME
Vintage Home for sale in Litchfield County, CT:
Enjoy this charming and private home on the Shepaug River! Every room in this house is welcoming, comfortable, and offers incredible privacy. The views from the kitchen, living room, screened porch, and bedrooms lead down to the river and up to the hills beyond. While enjoying the secluded setting, fire pit, and river access, you are also just minutes to Litchfield, New Milford, New Preston, Mt. Tom, Lake Waramaug, and so much more! Featuring a BRAND NEW AC split system! It's the perfect spot to enjoy the best of both worlds - fabulous restaurants, shopping, hiking, recreational activities, and the privacy and comfort of your own house in the country. This house has an open farmhouse kitche

$624,900

2 beds1.5 baths1,611 sq ft

2 Valley Rd, New Preston Marble Dale, CT 06777

Shepaug river • River access • Charming pantry

Property at 127 Old Goshen Rd, Norfolk, CT 06058, 7 beds, 6.5 baths

$2,900,000

7 beds6.5 baths4,824 sq ft

127 Old Goshen Rd, Norfolk, CT 06058

Property at 21 Shepard Rd, Norfolk, CT 06058, 4 beds, 1.5 baths

$425,000

4 beds1.5 baths2,528 sq ft

21 Shepard Rd, Norfolk, CT 06058

Property at 96 Squire Rd, Roxbury, CT 06783, 4 beds, 3.5 baths

$1,399,000

4 beds3.5 baths3,077 sq ft

96 Squire Rd, Roxbury, CT 06783

Property at 1 N Shore Rd, Warren, CT 06777, 4 beds, 2 baths

$699,000

4 beds2 baths2,261 sq ft

1 N Shore Rd, Warren, CT 06777

Property at 102 Melius Rd, Warren, CT 06754-1503, 7 beds, 6 baths

$7,400,000

7 beds6 baths6,844 sq ft

102 Melius Rd, Warren, CT 06754-1503

Houlihan Lawrence Inc.

Property at 1657 Weed Rd, Torrington, CT 06790, 3 beds, 2 baths

$524,900

3 beds2 baths2,604 sq ft

1657 Weed Rd, Torrington, CT 06790

Property at 110 Sharon Rd, Lakeville, CT 06039, 4 beds, 4 baths

$2,295,000

4 beds4 baths3,114 sq ft

110 Sharon Rd, Lakeville, CT 06039

Property at 143 Whitcomb Hill Rd, Cornwall Bridge, CT 06754, 3 beds, 2 baths

$795,000

3 beds2 baths1,951 sq ft

143 Whitcomb Hill Rd, Cornwall Bridge, CT 06754

Property at 118 Lake Dr, Bethlehem, CT 06751, 3 beds, 3.5 baths

$950,000

3 beds3.5 baths2,416 sq ft

118 Lake Dr, Bethlehem, CT 06751

Property at 24 Whittlesey Ave, New Milford, CT 06776, 5 beds, 1.5 baths

$525,000

5 beds1.5 baths2,192 sq ft

24 Whittlesey Ave, New Milford, CT 06776

Property at 47 South St, Roxbury, CT 06783, 3 beds, 2 baths

$875,000

3 beds2 baths2,489 sq ft

47 South St, Roxbury, CT 06783

Property at 537 Main St, New Hartford, CT 06057, 4 beds, 2.5 baths

$459,900

4 beds2.5 baths2,363 sq ft

537 Main St, New Hartford, CT 06057

Property at 9 Riverview Ct, New Milford, CT 06776, 2 beds, 1 bath

$295,000

2 beds1 bath1,269 sq ft

9 Riverview Ct, New Milford, CT 06776

Property at 46 Hart St, Watertown, CT 06795, 3 beds, 1 bath

$379,900

3 beds1 bath1,120 sq ft

46 Hart St, Watertown, CT 06795

Property at 528 Clearview Ave, Torrington, CT 06790, 1 bed, 1 bath

$170,000

1 bed1 bath735 sq ft

528 Clearview Ave, Torrington, CT 06790

Property at 22 Park St, Thomaston, CT 06787, 4 beds, 3 baths

$389,900

4 beds3 baths1,629 sq ft

22 Park St, Thomaston, CT 06787

Property at 298 Kenyon Rd, Morris, CT 06763, 4 beds, 2 baths

$599,999

4 beds2 baths1,746 sq ft

298 Kenyon Rd, Morris, CT 06763

Property at 159 Merryall Rd, New Milford, CT 06776, 3 beds, 2 baths

$1,250,000

3 beds2 baths1,796 sq ft

159 Merryall Rd, New Milford, CT 06776

Property at 279 Main St, Torrington, CT 06790, 3 beds, 1 bath

$269,900

3 beds1 bath1,697 sq ft

279 Main St, Torrington, CT 06790

Property at 291 E Main St, Torrington, CT 06790, 6 beds, 6 baths

$600,000

6 beds6 baths4,431 sq ft

291 E Main St, Torrington, CT 06790

Property at 227 Morro St, Oakville, CT 06779, 2 beds, 2 baths

$275,000

2 beds2 baths1,470 sq ft

227 Morro St, Oakville, CT 06779

Property at 16 Gaylord Rd, Gaylordsville, CT 06755, 2 beds, 1 bath

$340,000

2 beds1 bath1,774 sq ft

16 Gaylord Rd, Gaylordsville, CT 06755

Property at 179 Greenridge Rd, Torrington, CT 06790, 5 beds, 2 baths

$275,000

5 beds2 baths1,818 sq ft

179 Greenridge Rd, Torrington, CT 06790

Property at 74 Middle Quarter Rd, Woodbury, CT 06798, 4 beds, 2.5 baths

$725,000

4 beds2.5 baths2,874 sq ft

74 Middle Quarter Rd, Woodbury, CT 06798

Property at 785 Main St, Plymouth, CT 06782, 3 beds, 1 bath

$277,300

3 beds1 bath1,175 sq ft

785 Main St, Plymouth, CT 06782

Property at 163 Dublin Rd, Falls Village, CT 06031, 2 beds, 2 baths

$925,000

2 beds2 baths1,784 sq ft

163 Dublin Rd, Falls Village, CT 06031

Property at 50 Main St, Salisbury, CT 06039, 4 beds, 3.5 baths

$2,345,000

4 beds3.5 baths3,058 sq ft

50 Main St, Salisbury, CT 06039

Property at Undisclosed address, Washington Depot, CT 06794, 2 beds, 1 bath

$985,000

2 beds1 bath800 sq ft

Undisclosed address, Washington Depot, CT 06794

Property at 115 Margerie St, Torrington, CT 06790, 3 beds, 2 baths

$275,000

3 beds2 baths1,560 sq ft

115 Margerie St, Torrington, CT 06790

Property at 37 Linden St, Torrington, CT 06790, 4 beds, 1.5 baths

$319,890

4 beds1.5 baths2,136 sq ft

37 Linden St, Torrington, CT 06790

Property at 168 Newfield Rd, Torrington, CT 06790, 2 beds, 1 bath

$229,900

2 beds1 bath825 sq ft

168 Newfield Rd, Torrington, CT 06790

Property at 11 Old Creamery Rd, Colebrook, CT 06021, 3 beds, 2 baths

$499,000

3 beds2 baths2,186 sq ft

11 Old Creamery Rd, Colebrook, CT 06021

Property at 21 Perry St, Lakeville, CT 06039, 3 beds, 3 baths

$1,045,000

3 beds3 baths2,113 sq ft

21 Perry St, Lakeville, CT 06039

Property at 406 Wells Hill Rd, Lakeville, CT 06039, 6 beds, 6.5 baths

$8,875,000

6 beds6.5 baths8,334 sq ft

406 Wells Hill Rd, Lakeville, CT 06039

Property at 3824 Hall Meadow Rd, Norfolk, CT 06058, 4 beds, 3 baths

$474,900

4 beds3 baths2,504 sq ft

3824 Hall Meadow Rd, Norfolk, CT 06058

Property at 109 Church Hill Rd, Washington Depot, CT 06794, 3 beds, 3.5 baths

$995,000

3 beds3.5 baths2,279 sq ft

109 Church Hill Rd, Washington Depot, CT 06794

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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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