Vintage homes for sale & real estate in Connecticut, CT

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ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Excellent investment opportunity OR owner-occupied three-family in a convenient Norwich location! This well-maintained property features 3 spacious units consisting of 2x 2-bedroom, 1-bath apartments and 1x 1-bedroom, 1-bath apartment, offering an attractive mix for both investors and owner-occupants. Each unit has been thoughtfully maintained and offers bright, functional living spaces, generously sized bedrooms, and the convenience of its own laundry hookups, providing value and appeal for tenants. Outside, you'll appreciate the expansive off-street parking lot, offering ample parking for residents and guests alike-a rare and highly desirable feature for a multi-family property. The prope

$429,900

5 beds3 baths2,561 sq ft

84 Laurel Hill Ave, Norwich, CT 06360

Three-family • Laundry hookups • Strong rental appeal

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Discover a premier investment or owner-occupant opportunity in New Haven's Fair Haven District. This side-by-side duplex two-family home is perfect for those looking to live in one unit while renting the other, or for savvy investors seeking growth. Unit 71 was completely renovated in 2018, while the second unit offers a flexible layout. Both units currently feature under-market rents, providing significant room for value increase. Enjoy stunning views from private back decks on a serene . 32-acre wooded lot. Complete with a full basement, this versatile property is being sold "as-is. " * * Note you will not be able to access this property from Lenox St * * to get to 71-73 L

$340,000

3 beds2 baths1,344 sq ft

71 Lenox St, New Haven, CT 06511

Private back decks • Wooded lot • Flexible layout

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Offering more than 2,400 square feet of living space for UNDER $400k! and in the heart of Spring Glen, 40 Filbert Street is an exceptional opportunity at this new price. Its generous size, flexible floor plan, and desirable location give buyers the chance to enjoy the home now, add their own personal style, and build equity for the future. Hardwood floors, high ceilings, and two fireplaces bring warmth and character to the home. The main level offers wonderful versatility, with a welcoming living room centered around a fireplace, a bright dining room, and a large eat-in kitchen. An oversized family room with a second fireplace provides even more space for movie nights, celebrations, or simp

$399,900

3 beds2.5 baths2,436 sq ft

40 Filbert St, Hamden, CT 06517

Spring glen location • Large eat-in kitchen • Huge family room

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Welcome to 220 Jackson Street. This is a beautifully renovated home with an in-law suite. This spacious property offers an exceptional opportunity for generational living, investors and owner-occupants. Originally built in 1845, the home blends timeless character with modern updates and features two well-designed living areas, generous living space, and a large 1.8-acre lot. This versatile property offers endless possibilities in a convenient Thomaston location.

$529,900

5 beds2 baths2,814 sq ft

220 Jackson St, Thomaston, CT 06787

In-law suite • Large lot • Two living areas

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Preston multi-family ideally located between two of the world's largest casinos and the campus for Electric Boat, the US Sub Base and the US Coast Guard. Ideal multi-family property with parking and rear yard for entertaining guests or letting the pets run in an open environment. Ideal investment opportunity for 1031 Exchange. Multi-family home currently has tenants in both units. Conveniently located to both I395 and I95 and the Mystic community. Enjoy shoreline communities of Westerly and Rhode Island Beaches. Each of the 2 units has 3 bedrooms and 1 full bathroom with tub. Excellent investment opportunity.

$325,000

6 beds2 baths1,913 sq ft

120 Route 2A, Preston, CT 06351

Rear yard • Multi-family • Parking

Property at 366 West Woods Rd, Hamden, CT 06518, 3 beds, 1.5 baths

$350,000

3 beds1.5 baths1,448 sq ft

366 West Woods Rd, Hamden, CT 06518

Property at 15 Matson Ct, Waterbury, CT 06704, 6 beds, 3 baths

$435,000

6 beds3 baths4,003 sq ft

15 Matson Ct, Waterbury, CT 06704

Property at 195 Sherman Ave, Meriden, CT 06450, 3 beds, 2 baths

$274,000

3 beds2 baths1,827 sq ft

195 Sherman Ave, Meriden, CT 06450

Property at 465 Lime Rock Rd, Lakeville, CT 06039, 2 beds, 2.5 baths

$485,000

2 beds2.5 baths1,996 sq ft

465 Lime Rock Rd, Lakeville, CT 06039

Property at 617 E Main St, Norwich, CT 06360, 5 beds, 2 baths

$249,900

5 beds2 baths2,512 sq ft

617 E Main St, Norwich, CT 06360

Property at 40 Main St, Plainfield, CT 06374, 6 beds, 4.5 baths

$995,000

6 beds4.5 baths5,856 sq ft

40 Main St, Plainfield, CT 06374

Property at 32 Liberty St, Madison, CT 06443, 3 beds, 3 baths

$1,299,000

3 beds3 baths1,188 sq ft

32 Liberty St, Madison, CT 06443

Property at 98 Huntington Rd, Bridgeport, CT 06608, 4 beds, 1 bath

$350,000

4 beds1 bath1,895 sq ft

98 Huntington Rd, Bridgeport, CT 06608

Property at 51-71 Park Ave Unit OM8, Danbury, CT 06810, 2 beds, 1 bath

$192,000

2 beds1 bath701 sq ft

51-71 Park Ave Unit OM8, Danbury, CT 06810

Property at 93 Gilliver Rd, Griswold, CT 06351, 3 beds, 1 bath

$400,000

3 beds1 bath1,473 sq ft

93 Gilliver Rd, Griswold, CT 06351

Property at 244 Sherman Ave, New Haven, CT 06518, 6 beds, 4 baths

$499,900

6 beds4 baths4,090 sq ft

244 Sherman Ave, New Haven, CT 06518

Property at 326 Lake Shore Dr, Middlebury, CT 06762, 3 beds, 2 baths

$520,000

3 beds2 baths1,568 sq ft

326 Lake Shore Dr, Middlebury, CT 06762

Property at 130 Plymouth St, New Haven, CT 06519, 5 beds, 3 baths

$525,000

5 beds3 baths2,324 sq ft

130 Plymouth St, New Haven, CT 06519

Property at 106 McDermott Cir, Hamden, CT 06514, 3 beds, 1.5 baths

$449,900

3 beds1.5 baths2,076 sq ft

106 McDermott Cir, Hamden, CT 06514

Property at 350 High St, Naugatuck, CT 06770, 3 beds, 1.5 baths

$290,000

3 beds1.5 baths1,268 sq ft

350 High St, Naugatuck, CT 06770

Property at 14 Rice Rd, Woodbridge, CT 06525, 3 beds, 1.5 baths

$629,900

3 beds1.5 baths2,920 sq ft

14 Rice Rd, Woodbridge, CT 06525

Property at 406 Harbor Rd, Southport, CT 06890, 5 beds, 4.5 baths

$3,850,000

5 beds4.5 baths3,921 sq ft

406 Harbor Rd, Southport, CT 06890

Property at 2415 Durham Rd, Madison, CT 06443, 2 beds, 1.5 baths

$880,000

2 beds1.5 baths1,795 sq ft

2415 Durham Rd, Madison, CT 06443

Property at 380 S Burnham Hwy, Lisbon, CT 06351, 3 beds, 1 bath

$298,000

3 beds1 bath1,033 sq ft

380 S Burnham Hwy, Lisbon, CT 06351

Property at 78 Jobs Rd, Wallingford, CT 06492, 3 beds, 2 baths

$474,900

3 beds2 baths1,134 sq ft

78 Jobs Rd, Wallingford, CT 06492

Property at 250 Main St, Ridgefield, CT 06877, 4 beds, 4.5 baths

$5,495,000

4 beds4.5 baths5,778 sq ft

250 Main St, Ridgefield, CT 06877

Property at 142 Second Hill Rd, New Milford, CT 06776, 3 beds, 3.5 baths

$819,500

3 beds3.5 baths2,866 sq ft

142 Second Hill Rd, New Milford, CT 06776

Property at 461 Wells Hill Rd, Lakeville, CT 06039, 4 beds, 3 baths

$1,645,000

4 beds3 baths2,100 sq ft

461 Wells Hill Rd, Lakeville, CT 06039

Property at 2049 Corbin Ave, New Britain, CT 06053, 3 beds, 1 bath

$299,900

3 beds1 bath1,144 sq ft

2049 Corbin Ave, New Britain, CT 06053

Property at 54 W North St #417, Stamford, CT 06902, 2 beds, 1 bath

$169,950

2 beds1 bath900 sq ft

54 W North St #417, Stamford, CT 06902

Property at 71 Strawberry Hill Ave #909, Stamford, CT 06902, 1 bed, 1 bath

$239,900

1 bed1 bath725 sq ft

71 Strawberry Hill Ave #909, Stamford, CT 06902

Property at 1 Campfield Dr, Fairfield, CT 06825, 2 beds, 2 baths

$749,900

2 beds2 baths2,324 sq ft

1 Campfield Dr, Fairfield, CT 06825

Property at 161 Thompson St, New Haven, CT 06511, 8 beds, 3 baths

$499,000

8 beds3 baths2,936 sq ft

161 Thompson St, New Haven, CT 06511

Property at 68 Morris St, Hamden, CT 06517, 3 beds, 2.5 baths

$439,900

3 beds2.5 baths1,586 sq ft

68 Morris St, Hamden, CT 06517

Property at 96 Allencrest Dr, Stratford, CT 06614, 4 beds, 2 baths

$496,375

4 beds2 baths1,884 sq ft

96 Allencrest Dr, Stratford, CT 06614

Property at 104 Higby Rd, Middletown, CT 06457, 3 beds, 1 bath

$399,999

3 beds1 bath1,112 sq ft

104 Higby Rd, Middletown, CT 06457

Property at 110 Minturn Rd, Bridgeport, CT 06606, 3 beds, 2 baths

$550,000

3 beds2 baths1,504 sq ft

110 Minturn Rd, Bridgeport, CT 06606

Property at 119 W Wakefield Blvd, Winsted, CT 06098, 4 beds, 2 baths

$849,900

4 beds2 baths1,781 sq ft

119 W Wakefield Blvd, Winsted, CT 06098

Property at 589 Racebrook Rd, Orange, CT 06477, 5 beds, 2 baths

$1,095,000

5 beds2 baths2,136 sq ft

589 Racebrook Rd, Orange, CT 06477

Property at 1440 Wood Ave, Bridgeport, CT 06604, 8 beds, 3 baths

$749,500

8 beds3 baths3,938 sq ft

1440 Wood Ave, Bridgeport, CT 06604

Property at 42 Couch Rd, New Preston Marble Dale, CT 06777, 3 beds, 2 baths

$995,000

3 beds2 baths1,910 sq ft

42 Couch Rd, New Preston Marble Dale, CT 06777

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Based on information submitted to the MLS GRID as of Mon Nov 02 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 3096 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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