Vintage homes for sale & real estate in Connecticut, CT

3,157 homes + 2 early access

Sort:

Recommended

Greenwich
Stamford
West Hartford
Norwalk
Westport
New Haven
Milford
Darien
Hartford
Ridgefield
Shelton
Danbury
Trumbull
Bridgeport
Stratford

COMING SOONFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Own a piece of the Connecticut Shoreline lifestyle with this exceptional dual-cottage property in the sought-after Chapman Beach community! Just a short stroll to the sand with deeded private beach rights, this rare offering features two completely renovated, year-round single-family homes on one lot. This distinctive coastal property offers the perfect combination of seaside living, flexibility, and established rental income potential. The charming 824 sq. ft. guest cottage is a proven 5-star Airbnb with an established rental history and Summer 2027 reservations already secured, which must be honored by the buyer. Rental income details are available upon request. Also offering a history of

$1,375,000

4 beds2 baths1,954 sq ft

73 Chapman Beach Rd, Westbrook, CT 06498

Private yard • Custom patio • Outdoor shower

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Cute Cape in a quiet neighborhood. Recent upgrades make this house a great starter home for anyone looking for easy route 8 Access. Walk to nearby restaurants. A must see for anyone looking in this price range. New photos to follow on 11/4 Owner is finishing up some cosmetic work and will be ready by November 4th.

$349,900

3 beds1.5 baths1,310 sq ft

59 Avenue E, Beacon Falls, CT 06403

Quiet neighborhood • Easy route 8 access • 0.25 acre lot

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
LIVE 11/2! Welcome to 126 Metro Street - An inviting 3-bedroom, 2-full-bath ranch with wonderful combination of classic charm, valuable updates, and endless possibilities! Situated on a level corner lot, this home features a spacious, fireplaced living room that creates a warm and welcoming atmosphere, beautiful hardwood flooring throughout most of the main level, and a bright all-season sunroom with sliding glass doors leading to the backyard-perfect for relaxing or entertaining. The full basement offers exceptional potential, featuring a partially finished area with framed-out space awaiting your personal vision and finishing touches. Whether you're dreaming of a recreation room, home off

$400,000

3 beds2 baths1,446 sq ft

126 Metro St, Bristol, CT 06010

Hardwood flooring • All-season sunroom • Corner lot

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Welcome to 30 Hillside St in Meriden! This charming Cape Cod-style home is situated on a quiet street and offers a welcoming feel from the moment you arrive. Step inside to find an inviting layout featuring an eat-in kitchen with stainless steel refrigerator, gas oven, quartz countertops and tile backsplash complemented by convenient under-cabinet lighting. A first-floor bedroom and spacious full bathroom provide added flexibility and convenience. Head upstairs to find two additional bedrooms, offering comfortable space for family, guests, or a home office. The living room and staircase feature new carpeting installed in 2026. Outside, enjoy the picture-perfect front porch, complete with li

$349,900

3 beds1 bath941 sq ft

30 Hillside St, Meriden, CT 06451

Quartz countertops • Gas oven • Eat-in kitchen

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Old Greenwich living made easy. Welcome to Havemeyer House, where a relaxed coastal lifestyle meets the comfort and convenience of a thoughtfully updated home. Set in one of Greenwich's most sought-after communities, this inviting Cape offers an approachable entry into the Old Greenwich lifestyle with thoughtful details, versatile spaces and a location that makes everyday living feel just a little more exceptional. Inside, natural light, hardwood floors and an open layout create a home that feels warm, comfortable and uncomplicated. The renovated kitchen adds character with a custom live-edge sycamore countertop, creating a natural gathering place at the heart of the home. Flex living is pa

$1,375,000

3 beds2 baths1,669 sq ft

50 Havemeyer Ln, Old Greenwich, CT 06870

First-floor bedroom • Ensuite bath • Renovated kitchen

Property at 91 Clarkson St, Bridgeport, CT 06605, 3 beds, 1.5 baths

$799,000

3 beds1.5 baths1,458 sq ft

91 Clarkson St, Bridgeport, CT 06605

Property at Undisclosed address, Redding, CT 06896, 4 beds, 3 baths

$1,500,000

4 beds3 baths3,588 sq ft

Undisclosed address, Redding, CT 06896

Property at 71 Strawberry Hill Ave #906, Stamford, CT 06902, 1 bed, 1 bath

$237,500

1 bed1 bath725 sq ft

71 Strawberry Hill Ave #906, Stamford, CT 06902

Property at 60 Robin Hood Rd, Stamford, CT 06907, 3 beds, 3 baths

$789,000

3 beds3 baths1,950 sq ft

60 Robin Hood Rd, Stamford, CT 06907

Property at 36 Main St S, Woodbury, CT 06798, 3 beds, 2.5 baths

$595,000

3 beds2.5 baths1,909 sq ft

36 Main St S, Woodbury, CT 06798

Property at 555 Middle Road Tpke, Woodbury, CT 06798, 2 beds, 1 bath

$359,900

2 beds1 bath990 sq ft

555 Middle Road Tpke, Woodbury, CT 06798

Property at 133 Castle Ave, Fairfield, CT 06825, 5 beds, 3 baths

$950,000

5 beds3 baths2,629 sq ft

133 Castle Ave, Fairfield, CT 06825

Property at 155 Nichols Ave, Shelton, CT 06484, 3 beds, 1 bath

$399,900

3 beds1 bath1,356 sq ft

155 Nichols Ave, Shelton, CT 06484

Property at 15 Placid St, Trumbull, CT 06611, 3 beds, 2.5 baths

$699,900

3 beds2.5 baths2,308 sq ft

15 Placid St, Trumbull, CT 06611

Property at 147 Chapel St, Stratford, CT 06614, 2 beds, 2.5 baths

$625,000

2 beds2.5 baths2,545 sq ft

147 Chapel St, Stratford, CT 06614

Property at 9 Terrace Dr, Bethel, CT 06801, 3 beds, 2.5 baths

$529,900

3 beds2.5 baths1,753 sq ft

9 Terrace Dr, Bethel, CT 06801

Property at 157 Pythian Ave, Torrington, CT 06790, 6 beds, 3 baths

$399,000

6 beds3 baths3,074 sq ft

157 Pythian Ave, Torrington, CT 06790

Property at 232 W Norwalk Rd, Norwalk, CT 06850, 4 beds, 3.5 baths

$1,475,000

4 beds3.5 baths3,283 sq ft

232 W Norwalk Rd, Norwalk, CT 06850

Property at 143 Wilson St, Hartford, CT 06106, 6 beds, 3 baths

$610,000

6 beds3 baths2,878 sq ft

143 Wilson St, Hartford, CT 06106

Property at 872 Main St, Torrington, CT 06790, 6 beds, 2 baths

$549,900

6 beds2 baths2,992 sq ft

872 Main St, Torrington, CT 06790

Property at 58-A Kelsey Pl, Madison, CT 06443, 2 beds, 1 bath

$725,000

Land0.28 acre (lot)

58-A Kelsey Pl, Madison, CT 06443

Property at 37 Quarry Rd, Beacon Falls, CT 06403, 4 beds, 1 bath

$39,900

Land8,276 sq ft (lot)

37 Quarry Rd, Beacon Falls, CT 06403

Viewing page 9 of 77

Based on information submitted to the MLS GRID as of Sat Oct 31 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 3139 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.

Vintage homes for sale & real estate in Connecticut, CT

Vintage Homes for Sale in Connecticut

Popular Cities in Connecticut

Popular Searches in Connecticut, CT