Vintage homes for sale & real estate in Fairfield County, CT

508 homes

Sort:

Recommended

NEW 25 MINS AGO

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, 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

3,920 sq ft lot • Built 1890

NEW 17 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, 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

NEW 19 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Stunning sun-filled 2-bedroom, 1-bath end unit fully renovated in 2021 with designer finishes throughout. Bright and airy with hardwood floors and incredible natural light flowing through every room from three exposures. The chef-inspired kitchen features custom cabinetry and newer stainless steel appliances, paired with a full-size, newer full size washer and dryer for true convenience. Both bedrooms offer excellent light and comfort, and the beautifully updated bathroom provides a sleek, spa-like feel. Enjoy indoor-outdoor living with a private balcony perfect for relaxing or entertaining. Additional storage includes a pull down attic plus shared basement space. Minutes to downtown Greenw

$695,000

2 beds1 bath986 sq ft

36 Putnam Park, Greenwich, CT 06830

Custom cabinetry • Fully renovated • Pull down attic

NEW 22 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Completely renovated home from the new insulation, sheetrock, electrical, furnace, water heater, CA, plumbing, doors, windows roof and more. Even new stairs from the first to second floors and a freshly painted exterior. Owner also indicates all utilities have been separated from the neighboring duplex. Hardwood floors in the living room and dining room, laminate on the second-floor hall and bedrooms with new tiled floors in the kitchen and bath. The driveway will also be sealed before closing. All you have to do is move right in and add a washer and dryer and enjoy. Close to bus lines, shopping and highways.

$335,900

2 beds1 bath952 sq ft

366 Columbus Ave, Stratford, CT 06615

New furnace • Renovated home • New plumbing

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Turnkey two-family home in Bridgeport's sought-after North End, delivering a powerful combination of comfort, updates, and a total monthly rent of $4,440. Each unit offers inviting living space, well-sized rooms, and thoughtful layouts that make the property appealing for both investors and future owner-occupants. The first floor features a bright interior with an updated kitchen and easy access to the yard. The upper unit adds exceptional space with multiple bedrooms and modern improvements that support long-term tenant stability. Recent upgrades include a newer asphalt roof (approx. 10 years), treated exterior decking, updated mechanical systems, gas heat, and public water and sewer. Sepa

$630,000

6 beds3 baths2,418 sq ft

605 Merritt St, Bridgeport, CT 06606

4,791 sq ft lot • Built 1942

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

$529,900

3 beds2 baths1,344 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 6 Windaway Rd, Bethel, CT 06801, 2 beds, 1 bath

$425,000

2 beds1 bath1,494 sq ft

6 Windaway Rd, Bethel, CT 06801

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 74 W North St, Stamford, CT 06902, 3 beds, 2 baths

$725,000

3 beds2 baths2,397 sq ft

74 W North St, Stamford, CT 06902

Property at 42 Wendy Rd, Trumbull, CT 06611, 3 beds, 2 baths

$569,900

3 beds2 baths1,238 sq ft

42 Wendy Rd, Trumbull, CT 06611

Property at 11 Judges Hollow Rd, Fairfield, CT 06824, 2 beds, 2 baths

$950,000

2 beds2 baths1,135 sq ft

11 Judges Hollow Rd, Fairfield, CT 06824

Property at 160 Cedar Rd, Southport, CT 06890, 2 beds, 1.5 baths

$1,699,000

2 beds1.5 baths2,131 sq ft

160 Cedar Rd, Southport, CT 06890

Property at 172 Swanson Ave, Stratford, CT 06614, 3 beds, 2 baths

$499,000

3 beds2 baths1,495 sq ft

172 Swanson Ave, Stratford, CT 06614

Property at 22 Summit Rd, Riverside, CT 06878, 4 beds, 2.5 baths

$2,795,000

4 beds2.5 baths3,022 sq ft

22 Summit Rd, Riverside, CT 06878

Property at 8 Moorland Rd, Trumbull, CT 06611, 4 beds, 4 baths

$875,000

4 beds4 baths3,862 sq ft

8 Moorland Rd, Trumbull, CT 06611

Property at 77 Maple St, Darien, CT 06820, 4 beds, 3 baths

$1,495,000

4 beds3 baths2,180 sq ft

77 Maple St, Darien, CT 06820

Property at 215 Overland Ave, Bridgeport, CT 06606, 4 beds, 2 baths

$435,000

4 beds2 baths1,460 sq ft

215 Overland Ave, Bridgeport, CT 06606

Property at 88 Valleywood Rd, Cos Cob, CT 06807, 2 beds, 1.5 baths

$1,200,000

2 beds1.5 baths1,328 sq ft

88 Valleywood Rd, Cos Cob, CT 06807

Property at 125 Wood Ave, Stratford, CT 06614, 3 beds, 1.5 baths

$425,000

3 beds1.5 baths1,356 sq ft

125 Wood Ave, Stratford, CT 06614

Property at 144 Warsaw St, Fairfield, CT 06825, 6 beds, 2 baths

$749,000

6 beds2 baths2,968 sq ft

144 Warsaw St, Fairfield, CT 06825

Property at 102 Summer St Unit 2A, Stamford, CT 06840, 2 beds, 1 bath

$320,000

2 beds1 bath872 sq ft

102 Summer St Unit 2A, Stamford, CT 06840

Property at 20 Oak Ridge GATE, Danbury, CT 06810, 4 beds, 2 baths

$559,900

4 beds2 baths1,676 sq ft

20 Oak Ridge GATE, Danbury, CT 06810

Property at 59 Pleasant St, Danbury, CT 06810, 6 beds, 2 baths

$579,900

6 beds2 baths1,600 sq ft

59 Pleasant St, Danbury, CT 06810

Property at 209 Rowayton Ave, Norwalk, CT 06853, 3 beds, 2.5 baths

$2,599,000

3 beds2.5 baths2,068 sq ft

209 Rowayton Ave, Norwalk, CT 06853

Property at 69 Glen Cir, Bridgeport, CT 06610, 5 beds, 2 baths

$399,900

5 beds2 baths1,350 sq ft

69 Glen Cir, Bridgeport, CT 06610

Property at 279 Knapps Hwy, Fairfield, CT 06825, 4 beds, 1 bath

$525,000

4 beds1 bath1,086 sq ft

279 Knapps Hwy, Fairfield, CT 06825

Property at 145 Canal St #2, Shelton, CT 06484, 2 beds, 2 baths

$310,000

2 beds2 baths1,050 sq ft

145 Canal St #2, Shelton, CT 06484

Property at 33 Assisi Way, Norwalk, CT 06851, 3 beds, 2 baths

$679,999

3 beds2 baths2,029 sq ft

33 Assisi Way, Norwalk, CT 06851

Property at 715 Wilcoxson Ave, Stratford, CT 06614, 5 beds, 1.5 baths

$580,000

5 beds1.5 baths2,285 sq ft

715 Wilcoxson Ave, Stratford, CT 06614

Property at 206 Huntington Tpke, Bridgeport, CT 06610, 3 beds, 1.5 baths

$499,990

3 beds1.5 baths1,416 sq ft

206 Huntington Tpke, Bridgeport, CT 06610

Property at 70 Strawberry Hill Ave Apt 3-2A, Stamford, CT 06902, 1 bath

$235,000

— beds1 bath660 sq ft

70 Strawberry Hill Ave Apt 3-2A, Stamford, CT 06902

Property at 559 Oak Bluff Ave, Stratford, CT 06615, 3 beds, 1 bath

$629,000

3 beds1 bath1,822 sq ft

559 Oak Bluff Ave, Stratford, CT 06615

Property at 74 Carleton Ave, Bridgeport, CT 06604, 8 beds, 2 baths

$645,000

8 beds2 baths2,849 sq ft

74 Carleton Ave, Bridgeport, CT 06604

Property at 17 Will Merry Ln, Greenwich, CT 06831, 6 beds, 6.5 baths

$4,695,000

6 beds6.5 baths7,168 sq ft

17 Will Merry Ln, Greenwich, CT 06831

Property at 306 Carroll Ave, Bridgeport, CT 06607, 3 beds, 1 bath

$350,000

3 beds1 bath1,318 sq ft

306 Carroll Ave, Bridgeport, CT 06607

Property at 25 Dairy Farm Rd, Norwalk, CT 06851, 4 beds, 2.5 baths

$700,000

4 beds2.5 baths1,672 sq ft

25 Dairy Farm Rd, Norwalk, CT 06851

Property at 131 Henry St, Greenwich, CT 06830, 3 beds, 3.5 baths

$1,200,000

3 beds3.5 baths2,099 sq ft

131 Henry St, Greenwich, CT 06830

Property at 45 Queens Ave, Stratford, CT 06614, 3 beds, 1.5 baths

$459,000

3 beds1.5 baths1,616 sq ft

45 Queens Ave, Stratford, CT 06614

Property at 148 W Hills Rd, New Canaan, CT 06840, 5 beds, 4.5 baths

$2,995,000

5 beds4.5 baths5,731 sq ft

148 W Hills Rd, New Canaan, CT 06840

Property at 533 Clinton Ave, Bridgeport, CT 06605, 6 beds, 2 baths

$699,999

6 beds2 baths3,459 sq ft

533 Clinton Ave, Bridgeport, CT 06605

Viewing page 1 of 9

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 Fairfield County

There are currently 508 vintage homes for sale in Fairfield County at a median listing price of $680K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Fairfield County stay on the market for 48 days and receive 4 offers. This map is refreshed with the newest listings in Fairfield County every 15 minutes.

In the past month, 896 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 778 condos, 1 townhouse, and 200 multi-family units for sale in Fairfield County last month. Find your dream home in Fairfield 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 Fairfield County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Fairfield County. If you're looking to sell your home in the Fairfield County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Fairfield County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Fairfield County, CT

Cities

Nearby Counties

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Fairfield County, CT

How to buy a house in Fairfield County, CT

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Connecticut

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.