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

876 homes

Sort:

Recommended

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
What a GEM of a multi-family in sought after Black Rock! Spacious legal 3-family property with ample off street parking, 2-car detached garage, fenced-in rear gravel outdoor storage area, full basement with newer mechanical systems, and beautifully maintained apartments. Fully occupied with wonderful, long-term tenants, separate utilities (natural gas, electric), and low historical vacancy. The first floor apartment includes 3 bedrooms (or 2 bedrooms plus formal living and dining rooms), living room, updated kitchen with pantry and in-unit laundry, bathroom, and front den/storage room (rented for $2300/month EXP 1/31/27). The second floor apartment includes 2 bedrooms, full bathroom, update

$849,000

7 beds3 baths3,361 sq ft

58-60 Scofield Ave, Bridgeport, CT 06605

Off street parking • Full basement • Detached garage

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to this wonderful expanded 4 bedroom Cape, set in a highly desirable Stratford neighborhood and offering a warm, inviting interior with a flexible floor plan. The beautifully remodeled kitchen features Provincial-style cabinetry, quartz countertops, stainless steel appliances, a breakfast counter, thoughtful corner storage, twin spice racks, and a convenient pass-through to the spacious family room. A door from the family room leads directly to the deck, creating an effortless connection between indoor and outdoor living. Just beyond the kitchen is the charming formal dining room with built-in corner hutches, while the expansive front-to-back living room features a fireplace, and bu

$564,900

4 beds1.5 baths2,084 sq ft

100 Brenair Ter, Stratford, CT 06615

Quartz countertops • Corner storage • Remodeled kitchen

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Turn key home! Move right in to this beautifully remodeled 3-bedroom, 2-bath home offering modern updates, comfortable living, and inviting outdoor space. The bright open-concept main level features hardwood floors, a fireplace, and a stylish new kitchen with quartz countertops and stainless steel appliances. The fully finished lower level adds approximately 750 sq. ft. of versatile living space for a home office, gym, recreation room, or guest area. Enjoy the new deck overlooking the expansive yard, perfect for outdoor dining and entertaining. Major updates include remodeled bathrooms, new windows, new well pump and tank, a new roof, central air, and other system improvements. Conveniently

$629,000

3 beds2 baths1,866 sq ft

57 Soundview Ave, Shelton, CT 06484

New well pump • New deck • Central air

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
This property presents an exceptional opportunity for a first-time homebuyer. It features three levels of fully renovated living space, comprising three bedrooms and one and a half bathrooms above grade. The basement is completed with a kitchen, full bathroom, family room, and a man cave. Additionally, there is a detached garage that offers further potential for customization.

$309,900

3 beds2.5 baths1,674 sq ft

302 Dover St, Bridgeport, CT 06610

Completed basement • Detached garage • 2,178 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
TURNKEY INCOME-PRODUCING ASSET + VALUE-ADD OPPORTUNITY IN STAMFORD'S DESIRABLE BULLS HEAD! Just minutes from Downtown Stamford, 109 Oaklawn Ave is a rare legal 2-unit property plus In-Law Apartment offering strong income, modern updates and exceptional future potential. Unit 1 features 3 Bedrooms, 1.5 Baths, spacious Living Room, Eat-in Kitchen and Primary Bedroom with en-suite Half Bath. Unit 2 offers 3 Bedrooms and Full Bath, while Unit 3 is a bright Studio with brand-new Kitchen and beautifully renovated Full Bath. Units 1 & 2 have new in-unit washers/dryers; all units feature new flooring and fresh paint. The partially finished, heated Basement offers potential for a 4th unit (do

$975,000

6 beds3.5 baths3,167 sq ft

109 Oaklawn Ave, Stamford, CT 06905

In law apartment • Fresh paint • Modern updates

Property at 1084 Iranistan Ave, Bridgeport, CT 06604, 8 beds, 5 baths

$799,999

8 beds5 baths4,072 sq ft

1084 Iranistan Ave, Bridgeport, CT 06604

Property at 51 Oronoque Trl, Shelton, CT 06484, 2 beds, 1 bath

$374,900

2 beds1 bath1,002 sq ft

51 Oronoque Trl, Shelton, CT 06484

Property at 33 Raymond Ter, Norwalk, CT 06855, 3 beds, 1.5 baths

$799,000

3 beds1.5 baths1,320 sq ft

33 Raymond Ter, Norwalk, CT 06855

Property at 89 Fayerweather Ter, Bridgeport, CT 06605, 3 beds, 1.5 baths

$739,900

3 beds1.5 baths1,567 sq ft

89 Fayerweather Ter, Bridgeport, CT 06605

Property at 55 Oil Mill Rd #26, Danbury, CT 06810, 1 bed, 1 bath

$285,000

1 bed1 bath1,105 sq ft

55 Oil Mill Rd #26, Danbury, CT 06810

Property at 78 Haddon St #5, Bridgeport, CT 06605, 2 beds, 1 bath

$235,000

2 beds1 bath900 sq ft

78 Haddon St #5, Bridgeport, CT 06605

Property at 211 Alsace St, Bridgeport, CT 06604, 1 bed, 1 bath

$99,999

1 bed1 bath600 sq ft

211 Alsace St, Bridgeport, CT 06604

Property at 85 Walnut St, Monroe, CT 06468, 3 beds, 2 baths

$595,000

3 beds2 baths1,376 sq ft

85 Walnut St, Monroe, CT 06468

Property at 60 Olive St, Bridgeport, CT 06605, 3 beds, 1.5 baths

$324,500

3 beds1.5 baths1,320 sq ft

60 Olive St, Bridgeport, CT 06605

Property at 15 Lafayette Ct Unit 1F, Greenwich, CT 06830, 1 bed, 1.5 baths

$1,050,000

1 bed1.5 baths1,144 sq ft

15 Lafayette Ct Unit 1F, Greenwich, CT 06830

Property at 285 Dexter Dr, Bridgeport, CT 06606, 4 beds, 2 baths

$520,900

4 beds2 baths1,876 sq ft

285 Dexter Dr, Bridgeport, CT 06606

Property at 1885 Old Town Rd, Bridgeport, CT 06606, 3 beds, 1.5 baths

$510,000

3 beds1.5 baths1,092 sq ft

1885 Old Town Rd, Bridgeport, CT 06606

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

$49,000

1 bed1 bath401 sq ft

373 Granfield Ave Unit B, Bridgeport, CT 06610

Property at 375 Franklin Ave, Stratford, CT 06614, 3 beds, 1 bath

$489,000

3 beds1 bath1,453 sq ft

375 Franklin Ave, Stratford, CT 06614

Property at 1076 E Main St #1, Stamford, CT 06902, 2 beds, 1 bath

$299,900

2 beds1 bath708 sq ft

1076 E Main St #1, Stamford, CT 06902

Property at 1149 Warner Hill Rd, Stratford, CT 06614, 4 beds, 2 baths

$649,000

4 beds2 baths2,782 sq ft

1149 Warner Hill Rd, Stratford, CT 06614

Property at 98 Ball Pond Rd, Danbury, CT 06811, 6 beds, 6 baths

$850,000

6 beds6 baths3,628 sq ft

98 Ball Pond Rd, Danbury, CT 06811

Property at 1065 Kossuth St, Bridgeport, CT 06608, 7 beds, 3 baths

$579,900

7 beds3 baths2,223 sq ft

1065 Kossuth St, Bridgeport, CT 06608

Property at 59 Rennell St #19, Bridgeport, CT 06604, 1 bed, 1 bath

$99,999

1 bed1 bath385 sq ft

59 Rennell St #19, Bridgeport, CT 06604

Property at 845 Stratford Rd, Stratford, CT 06615, 3 beds, 2 baths

$595,000

3 beds2 baths1,757 sq ft

845 Stratford Rd, Stratford, CT 06615

Property at 33 Melville Ave, Fairfield, CT 06825, 3 beds, 1.5 baths

$549,900

3 beds1.5 baths1,090 sq ft

33 Melville Ave, Fairfield, CT 06825

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

$498,990

4 beds1.5 baths2,140 sq ft

26 Powell Ter, Bridgeport, CT 06604

Property at 216 Cross Hill Rd, Monroe, CT 06468, 2 beds, 1 bath

$336,000

2 beds1 bath932 sq ft

216 Cross Hill Rd, Monroe, CT 06468

Property at 6 Brinsmade Ln, Sherman, CT 06784, 5 beds, 4 baths

$1,099,000

5 beds4 baths4,200 sq ft

6 Brinsmade Ln, Sherman, CT 06784

Property at 40 Kellogg St, Brookfield, CT 06804, 5 beds, 2 baths

$885,000

5 beds2 baths2,130 sq ft

40 Kellogg St, Brookfield, CT 06804

Property at 240 Sheridan St, Bridgeport, CT 06610, 6 beds, 3 baths

$549,500

6 beds3 baths2,940 sq ft

240 Sheridan St, Bridgeport, CT 06610

Property at 1680 Main St, Stratford, CT 06615, 3 beds, 1.5 baths

$550,000

3 beds1.5 baths1,454 sq ft

1680 Main St, Stratford, CT 06615

Property at 195 Webb Cir, Monroe, CT 06468, 4 beds, 2.5 baths

$949,000

4 beds2.5 baths3,074 sq ft

195 Webb Cir, Monroe, CT 06468

Property at 465 James Farm Rd, Stratford, CT 06614, 4 beds, 2 baths

$679,900

4 beds2 baths2,034 sq ft

465 James Farm Rd, Stratford, CT 06614

Property at 220 Priscilla St, Bridgeport, CT 06610, 5 beds, 2.5 baths

$479,000

5 beds2.5 baths2,052 sq ft

220 Priscilla St, Bridgeport, CT 06610

Property at 326 Soundview Ave, Bridgeport, CT 06606, 4 beds, 2 baths

$459,000

4 beds2 baths1,715 sq ft

326 Soundview Ave, Bridgeport, CT 06606

Property at 11 Bedford Ave Unit S1, Norwalk, CT 06850, 1 bed, 1 bath

$229,000

1 bed1 bath492 sq ft

11 Bedford Ave Unit S1, Norwalk, CT 06850

Property at 2029 Kings Hwy, Fairfield, CT 06824, 6 beds, 3 baths

$1,200,000

6 beds3 baths2,487 sq ft

2029 Kings Hwy, Fairfield, CT 06824

Property at 256 Stillwater Ave, Stamford, CT 06902, 5 beds, 2 baths

$999,000

5 beds2 baths2,803 sq ft

256 Stillwater Ave, Stamford, CT 06902

Property at 1757 E Main St, Bridgeport, CT 06610, 8 beds, 3 baths

$725,000

8 beds3 baths4,590 sq ft

1757 E Main St, Bridgeport, CT 06610

Property at 57-59 West St, Danbury, CT 06810, 8 beds, 6 baths

$1,399,000

8 beds6 baths5,338 sq ft

57-59 West St, Danbury, CT 06810

Viewing page 8 of 22

Based on information submitted to the MLS GRID as of Mon Oct 19 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 Fairfield County

There are currently 869 vintage homes for sale in Fairfield County at a median listing price of $699K. 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 49 days and receive 3 offers. This map is refreshed with the newest listings in Fairfield County every 15 minutes.

In the past month, 752 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 893 condos, 1 townhouse, and 218 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

Nearby Counties

Cities

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

4 Redfin agents serving Fairfield County

Deals*

4.5

Satisfaction

201

Homes closed*

* Data from the last year

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

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.