Vintage homes for sale & real estate in Connecticut, CT

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ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Well maintained two family home located on the Hills. Many renovations have been done within the four years it has been owned by the Ruiz's. New windows, garage doors, and heating system. This property is ready for a new owner. Landlords, investors, or simply a large family willing to live together, whomever you are, come and take a look. AS IS.

$410,000

4 beds2 baths1,738 sq ft

91 Jewett St, Ansonia, CT 06401

Garage doors • Two family home • Heating system

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
"Rare redevelopment opportunity in Bridgeport's sought-after North End!" This offering includes three separately assessed parcels -936 Chopsey Hill Road, 475 Alba Ave. and 495 Alba Ave. - all to be conveyed together. No exceptions!! Total list price for all 3 parcels combined is $519,900. (936 Chopsey Hill Rd $255,000 + 475 Alba Ave. $142,750 + 495 Alba Ave. $122,150) property taxes combined are $5,970.00. The existing 2 bedroom, 1 bath Ranch requires renovation and is likely best suited for removal, to maximize the full development potential of the land. Any future subdivision, utilities, or development potential is subject to buyer's due diligence and City of Bridgeport approval

$255,000

2 beds1 bath994 sq ft

936 Chopsey Hill Rd, Bridgeport, CT 06606

6,969 sq ft lot • 2 garage spots • Built 1960

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Discover this meticulously maintained and oversized 2-family home located in a highly desirable neighborhood of Upper Bridgeport. Perfect for owner-occupants and investors alike, the property also includes a bonus "owner's unit, " offering exceptional versatility and added value. All units have been tastefully updated with modern kitchens, refreshed bathrooms, upgraded flooring, and contemporary fixtures throughout. Major mechanicals and essential home systems are in like-new condition, providing peace of mind and minimal ongoing maintenance. The first unit offers a spacious 3-bedroom layout, while the second unit and bonus owner's unit each feature 2 bedrooms. With ample off-stre

$599,900

7 beds3 baths2,708 sq ft

865 Iranistan Ave, Bridgeport, CT 06604

Modern kitchens • Upgraded flooring • Bonus owner's unit

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
CALLING ALL INVESTORS! This well-kept two-family duplex in a neighborhood of similar multi-family homes offers a solid and reliable rental history. Each unit is a mirror image, featuring a living room, eat-in kitchen, and private access to a partial basement. The upper level includes two bedrooms, and a full bath. Added perks include in-unit laundry hookups, dedicated storage space in the basement, gas furnace, newer water heater in unit 37 (2023), and fenced backyard. Separate utilities. A simple, efficient, and easy-to-rent income-producing property ready to enhance any investor's portfolio.

$350,000

4 beds2 baths1,584 sq ft

37 Seaman Cir, Manchester, CT 06040

Separate utilities • Two-family duplex • Fenced backyard

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
This 1-2 BR Ranch Cottage is situated on a 0.24 acre corner lot. It is 5 minutes to Route 8 & the Merrit Parkway (Rte. 15). House is hooked up to City Water & Sewer. At this price you could renovate or tear down & build your new home. This is conveniently located to all Shelton has to offer and of course, LOW Shelton Taxes! Please note that house is Winterized! Sold As Is!

$210,000

1 bed1 bath662 sq ft

35 Saginaw Trl, Shelton, CT 06484

City water • Low shelton taxes • Corner lot

Property at 366 Columbus Ave, Stratford, CT 06615, 2 beds, 1 bath

$335,900

2 beds1 bath952 sq ft

366 Columbus Ave, Stratford, CT 06615

Property at 9 Omar St, Seymour, CT 06483, 3 beds, 2.5 baths

$479,000

3 beds2.5 baths1,865 sq ft

9 Omar St, Seymour, CT 06483

Property at 16 Cedar Hill Rd, Shelton, CT 06484, 3 beds, 2 baths

$529,900

3 beds2 baths1,704 sq ft

16 Cedar Hill Rd, Shelton, CT 06484

Property at 509 Pembroke St, Bridgeport, CT 06608, 4 beds, 3 baths

$449,000

4 beds3 baths2,290 sq ft

509 Pembroke St, Bridgeport, CT 06608

Property at 10 Brookside Dr, Woodbridge, CT 06525, 3 beds, 3 baths

$684,900

3 beds3 baths2,541 sq ft

10 Brookside Dr, Woodbridge, CT 06525

Property at 21 Ormond St, Milford, CT 06461, 3 beds, 1.5 baths

$489,900

3 beds1.5 baths1,120 sq ft

21 Ormond St, Milford, CT 06461

Property at 28 Aquila Rd, Stamford, CT 06902, 4 beds, 2 baths

$649,900

4 beds2 baths1,344 sq ft

28 Aquila Rd, Stamford, CT 06902

Property at 9 Cook St, Manchester, CT 06040, 3 beds, 1.5 baths

$279,900

3 beds1.5 baths1,164 sq ft

9 Cook St, Manchester, CT 06040

Property at 574 Butternut St, Middletown, CT 06457, 4 beds, 3 baths

$365,000

4 beds3 baths1,876 sq ft

574 Butternut St, Middletown, CT 06457

Property at 13 Town St, Norwich, CT 06360, 3 beds, 2.5 baths

$299,900

3 beds2.5 baths1,252 sq ft

13 Town St, Norwich, CT 06360

Property at 44 3rd St, Wallingford, CT 06492, 3 beds, 2 baths

$349,900

3 beds2 baths1,442 sq ft

44 3rd St, Wallingford, CT 06492

Property at 9 Madison St, Hartford, CT 06183, 5 beds, 2.5 baths

$425,000

5 beds2.5 baths3,613 sq ft

9 Madison St, Hartford, CT 06183

Property at 105 Jericho Rd, Middlebury, CT 06762, 3 beds, 2.5 baths

$465,000

3 beds2.5 baths2,364 sq ft

105 Jericho Rd, Middlebury, CT 06762

Property at 20 Georgetown Rd, Weston, CT 06883, 3 beds, 2 baths

$524,000

3 beds2 baths1,616 sq ft

20 Georgetown Rd, Weston, CT 06883

Property at 118 Lake Shore Blvd, Stafford Springs, CT 06076

$44,900

— beds— baths— sq ft

118 Lake Shore Blvd, Stafford Springs, CT 06076

Property at 54 Lavelle Ave, New Fairfield, CT 06812

$150,000

— beds— baths— sq ft

54 Lavelle Ave, New Fairfield, CT 06812

Property at 671 oxford Rd, Oxford, CT 06478

$1,250,000

— beds— baths— sq ft

671 oxford Rd, Oxford, CT 06478

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Based on information submitted to the MLS GRID as of Tue Dec 09 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 Connecticut

There are currently 2062 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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