Vintage homes for sale & real estate in Connecticut, CT

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ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Currently set up as a multifamily in a single family zone. Exceptional opportunity in one of Cos Cob's most desirable neighborhoods! This charming two-family offers incredible versatility for investors, builders, and end users. Renovate the existing multifamily or explore conversion into a beautiful single-family residence. With current rents below market, there is immediate income and significant potential to optimize rental revenue. Buyers considering conversion can collect rent to offset carrying costs while pursuing plans and approvals. Features include hardwood floors, spacious living areas, a large rear deck, private backyard, attached garage, and driveway parking. A rare opportunity

$1,495,000

4 beds3 baths2,243 sq ft

4 Tremont St, Greenwich, CT 06830

Attached garage • Private backyard • Driveway parking

Mike Parelli Real Estate LLC

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Welcome to Spring Path Farm-a serene and sophisticated 15+ acre gentleman's estate offering a rare blend of timeless country elegance, privacy, and endless possibility. Approached by a long, winding private drive, the stately 7,698 sq ft Colonial residence has been thoughtfully renovated and expanded with exceptional craftsmanship. Inside, classic millwork, four warm stone fireplaces, and floor-to-ceiling windows framed by stunning nature views set a refined tone. Designed for both relaxation and grand entertaining, the main house features a primary bedroom suite with a private deck for quiet mornings, a vast back deck built for summer gatherings, and a lower-level billiard and media room d

$2,200,000

4 beds4.5 baths7,698 sq ft

6 Pine Hill Rd, Burlington, CT 06013

Vast back deck • Lush grounds • Stone walls

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
86-90 West Street, Litchfield, CT offers the beauty of a character-filled antique home and the possibilities of three residential buildings, all in the center of historic town. A gracious covered porch, columned entrance, bay windows, and distinctive arched windows create an inviting architectural presence. With village shops, restaurants, and the historic Green nearby, this is a setting where the pleasures of Litchfield become part of everyday life. Inside, richly varied wood floors reveal beautiful honey, amber, and deeper brown tones. Substantial paneled pocket doors connect sunlit rooms, while intricate woodwork, a carved fireplace mantel, and a beautifully detailed staircase showcase c

$1,245,000

7 beds6 baths3,289 sq ft

86-90 West St, Litchfield, CT 06759

Covered porch • Wood floors • Columned entrance

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Welcome to 53 Two Mile Road, Farmington, CT! This charming ranch-style home offers comfortable one-level living in a highly sought-after Farmington location. Featuring 3 spacious bedrooms, 1.5 bathrooms, and an inviting open floor plan, this home provides a wonderful combination of functionality, comfort, and modern updates. The updated kitchen features newer cabinetry and appliances, while the generously sized bedrooms offer plenty of space for relaxation. A bright, fully windowed additional living room provides a versatile space for entertaining, a home office, or everyday enjoyment. The property also boasts a large, level backyard, perfect for outdoor activities, gardening, or gatherings

$549,900

3 beds1.5 baths1,836 sq ft

53 Two Mile Rd, Farmington, CT 06032

Updated kitchen • Large level backyard • One level living

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
This well-maintained 5-bedroom, 2-full-bath home at 1885 Old Town Rd offers approximately 1,831 square feet of living space, including the basement area. The property features natural gas, city water, and city sewer, with a new water heater installed in 2026. Currently rented for $4,500 per month through May 31, 2027, the home offers immediate rental income for the current owner while providing flexibility for the next owner. Whether you're looking for an income-producing property, considering future owner occupancy, or looking for an opportunity to increase rental income over time, this property offers several possibilities. Ideally located in Bridgeport's North End, the home is close to

$490,000

3 beds1.5 baths1,092 sq ft

1885 Old Town Rd, Bridgeport, CT 06606

6,969 sq ft lot • Built 1960 • Listed 26 days

Property at 11 Gates Ave, Waterbury, CT 06705, 3 beds, 1.5 baths

$275,000

3 beds1.5 baths1,366 sq ft

11 Gates Ave, Waterbury, CT 06705

Property at 585 Hartford Tpke, Vernon, CT 06066, 3 beds, 1.5 baths

$375,000

3 beds1.5 baths1,536 sq ft

585 Hartford Tpke, Vernon, CT 06066

Property at 685 Main St, Ansonia, CT 06401, 3 beds, 1 bath

$289,900

3 beds1 bath1,280 sq ft

685 Main St, Ansonia, CT 06401

Property at 110 Matianuck Ave, Windsor, CT 06095, 3 beds, 2 baths

$275,000

3 beds2 baths1,229 sq ft

110 Matianuck Ave, Windsor, CT 06095

Property at 66 Carroll Dr, Torrington, CT 06790, 3 beds, 2 baths

$359,900

3 beds2 baths1,506 sq ft

66 Carroll Dr, Torrington, CT 06790

Property at 163 Saltonstall Ave, New Haven, CT 06513, 3 beds, 2 baths

$299,900

3 beds2 baths1,435 sq ft

163 Saltonstall Ave, New Haven, CT 06513

Property at 467 Quaker Farms Rd, Oxford, CT 06478, 4 beds, 2.5 baths

$775,000

4 beds2.5 baths2,049 sq ft

467 Quaker Farms Rd, Oxford, CT 06478

Property at 159 Lydall Rd, East Hartford, CT 06118, 3 beds, 1.5 baths

$319,900

3 beds1.5 baths1,307 sq ft

159 Lydall Rd, East Hartford, CT 06118

Property at Undisclosed address, Waterbury, CT 06708, 3 beds, 2 baths

$259,900

3 beds2 baths1,920 sq ft

Undisclosed address, Waterbury, CT 06708

Property at 118 Camp St, Middletown, CT 06457, 3 beds, 2.5 baths

$425,000

3 beds2.5 baths1,740 sq ft

118 Camp St, Middletown, CT 06457

Property at 86 Lincoln Ave, Bristol, CT 06010, 3 beds, 1.5 baths

$295,000

3 beds1.5 baths1,114 sq ft

86 Lincoln Ave, Bristol, CT 06010

Property at 78 Hammond Hill Rd, Hampton, CT 06247, 4 beds, 2 baths

$449,900

4 beds2 baths2,002 sq ft

78 Hammond Hill Rd, Hampton, CT 06247

Property at 107 Division St, Ansonia, CT 06401, 4 beds, 2 baths

$400,000

4 beds2 baths1,509 sq ft

107 Division St, Ansonia, CT 06401

Property at 109 Oaklawn Ave, Stamford, CT 06905, 6 beds, 3.5 baths

$975,000

6 beds3.5 baths3,167 sq ft

109 Oaklawn Ave, Stamford, CT 06905

Property at 5 Whippoorwill Ln, Seymour, CT 06483, 3 beds, 1 bath

$369,000

3 beds1 bath1,412 sq ft

5 Whippoorwill Ln, Seymour, CT 06483

Property at 375 S Main St, Manchester, CT 06040, 3 beds, 3 baths

$480,000

3 beds3 baths1,787 sq ft

375 S Main St, Manchester, CT 06040

Property at 1016 Sperry Rd, Cheshire, CT 06410, 2 beds, 1 bath

$415,000

2 beds1 bath974 sq ft

1016 Sperry Rd, Cheshire, CT 06410

Property at 210 Maple Ave, Uncasville, CT 06382, 3 beds, 1.5 baths

$360,000

3 beds1.5 baths1,421 sq ft

210 Maple Ave, Uncasville, CT 06382

Property at 26 Fern Dr, Torrington, CT 06790, 4 beds, 1.5 baths

$365,000

4 beds1.5 baths1,770 sq ft

26 Fern Dr, Torrington, CT 06790

Property at 173 Stillwell Dr, Plainville, CT 06062, 3 beds, 2 baths

$339,900

3 beds2 baths1,248 sq ft

173 Stillwell Dr, Plainville, CT 06062

Property at 22 Jordan Ter, Waterford, CT 06385, 3 beds, 3 baths

$529,900

3 beds3 baths1,858 sq ft

22 Jordan Ter, Waterford, CT 06385

Property at 12 Westover Rd, New Britain, CT 06053, 4 beds, 1 bath

$299,900

4 beds1 bath1,238 sq ft

12 Westover Rd, New Britain, CT 06053

Property at 7 Peaceful Ln, Norwalk, CT 06851, 3 beds, 1 bath

$795,000

3 beds1 bath1,278 sq ft

7 Peaceful Ln, Norwalk, CT 06851

Property at 125 Geary Ave, Bristol, CT 06010, 3 beds, 1 bath

$279,900

3 beds1 bath1,049 sq ft

125 Geary Ave, Bristol, CT 06010

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

$699,000

2 beds2.5 baths1,508 sq ft

48 Preston Ln, Salisbury, CT 06068

Property at 373 Granfield Ave Unit B, Bridgeport, CT 06610, 1 bed, 1 bath

$44,500

1 bed1 bath401 sq ft

373 Granfield Ave Unit B, Bridgeport, CT 06610

Property at 131 Killingworth Rd, Higganum, CT 06441, 2 beds, 2 baths

$549,900

2 beds2 baths1,351 sq ft

131 Killingworth Rd, Higganum, CT 06441

Property at 18 Markham Pl, Meriden, CT 06450, 5 beds, 3 baths

$485,000

5 beds3 baths1,912 sq ft

18 Markham Pl, Meriden, CT 06450

Property at 57 Soundview Ave, Shelton, CT 06484, 3 beds, 2 baths

$629,000

3 beds2 baths1,866 sq ft

57 Soundview Ave, Shelton, CT 06484

Property at 36 Blodgett Roy Dr, New Britain, CT 06053, 3 beds, 1 bath

$379,900

3 beds1 bath1,524 sq ft

36 Blodgett Roy Dr, New Britain, CT 06053

Property at 11 Mountain View Rd, South Windsor, CT 06074, 3 beds, 2.5 baths

$699,900

3 beds2.5 baths3,323 sq ft

11 Mountain View Rd, South Windsor, CT 06074

Property at 5 Hamilton Ct, Norwich, CT 06360, 2 beds, 1 bath

$235,000

2 beds1 bath672 sq ft

5 Hamilton Ct, Norwich, CT 06360

Property at 22 Woodlawn Dr, Torrington, CT 06790, 3 beds, 1.5 baths

$379,900

3 beds1.5 baths1,859 sq ft

22 Woodlawn Dr, Torrington, CT 06790

Property at 26 Powell Ter, Bridgeport, CT 06604, 4 beds, 1.5 baths

$483,990

4 beds1.5 baths2,140 sq ft

26 Powell Ter, Bridgeport, CT 06604

Property at 36 Sultan St, Stratford, CT 06614, 3 beds, 1.5 baths

$499,999

3 beds1.5 baths1,422 sq ft

36 Sultan St, Stratford, CT 06614

Property at 10 Horseshoe Dr, Danbury, CT 06811, 3 beds, 1.5 baths

$499,000

3 beds1.5 baths1,770 sq ft

10 Horseshoe Dr, Danbury, CT 06811

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Based on information submitted to the MLS GRID as of Sun Nov 01 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 Connecticut

There are currently 3130 vintage homes for sale in Connecticut. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. This map is refreshed with the newest listings in Connecticut every 15 minutes.

Find your dream vintage homes in Connecticut 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 Connecticut are local experts and are ready to answer your questions about properties , neighborhoods, schools, and the newest listings for sale in Connecticut. If you're looking to sell your home in the Connecticut area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Connecticut with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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