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

508 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Absolute exceptional value for this 4-bed, 5-bath residence offering 3,335 sq. ft. of beautifully designed flexible living space. Meticulously and completely renovated in 2012.. .Light filled public space includes eat-in gourmet kitchen/dining area, living room/fireplace, sunroom & mudroom. Primary Bedroom suite with walk-in closets and additional double bedroom/play space and bath complete the 2nd floor. 3rd floor has amazing possibilities with flexible living space. Use as a fabulous bedroom suite, office, or relaxing space. Lower level is a self-contained apartment, complete with private entry, full bath, laundry, and bedroom/living space. Dream come true exterior patio/ gourmet ou

$949,000

4 beds5.5 baths2,288 sq ft

226 Alberta St, Fairfield, CT 06825

Gourmet kitchen • Walk-in closets • Sunroom

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Excellent investment opportunity in the heart of Bridgeport's Black Rock neighborhood. This 8-unit multifamily building features eight 2-bedroom, 1-bathroom units, each with spacious layouts and strong rental potential. The property includes separate utilities for each unit and has been well-maintained, making it ideal for investors seeking a stable, income-producing asset. Located just minutes from the train station, I-95, restaurants, shopping, and the shoreline, this property is well-positioned in one of Bridgeport's most desirable rental markets. Schedule your private showing today!

$1,900,000

16 beds8 baths5,824 sq ft

31 Whittier St, Bridgeport, CT 06605

Separate utilities • Well maintained • Multifamily building

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Exceptional investment opportunity in Bridgeport's desirable Black Rock neighborhood. This 8-unit multifamily property features eight 2-bedroom, 1-bathroom units, each with spacious layouts ideal for tenants seeking comfort and convenience. The building is well-maintained, with separate utilities and strong rental history, making it a turnkey addition to any portfolio. Located just minutes from Metro-North, I-95, shops, dining, and the waterfront, this property presents long-term value in a high-demand rental market. Schedule your private showing today!

$1,900,000

16 beds8 baths5,824 sq ft

25 Whittier St, Bridgeport, CT 06605

Spacious layouts • Separate utilities • Multifamily property

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Great location north of Barnum Avenue near Wooster Middle School ! Needs some TLC. Featuring living room with a fireplace. 2 full baths. Nice size rear deck. Level manageable sized lot. Expansive basement. Vinyl siding. Subject to Probate Court approval. Being sold "AS IS"

$375,000

2 beds2 baths1,026 sq ft

58 Auburn St, Stratford, CT 06614

Vinyl siding • Rear deck • Expansive basement

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 375 Silver St in Bridgeport-an inviting 4-bed, 2-bath home that's truly move-in ready. The main level offers a comfortable, functional layout with plenty of natural light, while the finished walk-out basement adds valuable extra space for work, play, or guests. Outside, the large yard is a standout feature-ideal for gatherings, gardening, or just spreading out. A newer backyard shed provides convenient storage, and the treehouse adds a touch of charm and fun. Located near shopping, schools, parks, and major routes, the home offers easy access to everyday essentials while still feeling like a private retreat. A great option for anyone looking for space, convenience, and a home tha

$499,900

4 beds2 baths1,296 sq ft

375 Silver St, Bridgeport, CT 06610

Newer backyard shed • Treehouse • Large yard

Property at 68 Center St, Westport, CT 06880, 4 beds, 2.5 baths

$925,000

4 beds2.5 baths2,044 sq ft

68 Center St, Westport, CT 06880

Property at 266 Peace St, Stratford, CT 06615, 8 beds, 4 baths

$849,000

8 beds4 baths2,469 sq ft

266 Peace St, Stratford, CT 06615

Property at 48 Richland Rd, Greenwich, CT 06830, 2 beds, 2 baths

$1,999,000

2 beds2 baths4,081 sq ft

48 Richland Rd, Greenwich, CT 06830

Property at 50 Pilgrim Rd, Bridgeport, CT 06610, 3 beds, 1.5 baths

$435,000

3 beds1.5 baths1,078 sq ft

50 Pilgrim Rd, Bridgeport, CT 06610

Property at 2 Chestnut St, Bethel, CT 06801, 3 beds, 2 baths

$635,000

3 beds2 baths2,751 sq ft

2 Chestnut St, Bethel, CT 06801

Property at 209 McGrath Ct, Stratford, CT 06615, 2 beds, 1 bath

$199,000

2 beds1 bath952 sq ft

209 McGrath Ct, Stratford, CT 06615

Property at 554 Brewster St #4, Bridgeport, CT 06605, 1 bed, 1 bath

$179,900

1 bed1 bath750 sq ft

554 Brewster St #4, Bridgeport, CT 06605

Property at 276 Otter Rock Dr, Greenwich, CT 06830, 8 beds, 6.5 baths

$27,500,000

8 beds6.5 baths11,536 sq ft

276 Otter Rock Dr, Greenwich, CT 06830

Property at 125 Prospect St Apt 2E, Stamford, CT 06901, 2 beds, 2 baths

$329,000

2 beds2 baths1,250 sq ft

125 Prospect St Apt 2E, Stamford, CT 06901

Property at 78 Fairmount Ave, Bridgeport, CT 06606, 5 beds, 2 baths

$560,000

5 beds2 baths1,600 sq ft

78 Fairmount Ave, Bridgeport, CT 06606

Property at 47 Lenox Ave, Bridgeport, CT 06605, 5 beds, 1.5 baths

$399,000

5 beds1.5 baths2,507 sq ft

47 Lenox Ave, Bridgeport, CT 06605

Property at 123 Beverly Dr, Bridgeport, CT 06610, 4 beds, 2 baths

$395,000

4 beds2 baths2,140 sq ft

123 Beverly Dr, Bridgeport, CT 06610

Property at 356 Taft Ave, Bridgeport, CT 06604, 4 beds, 2 baths

$499,900

4 beds2 baths1,960 sq ft

356 Taft Ave, Bridgeport, CT 06604

Property at 720 Queen St, Bridgeport, CT 06606, 6 beds, 4 baths

$725,000

6 beds4 baths2,542 sq ft

720 Queen St, Bridgeport, CT 06606

Property at 189 East Ave, Norwalk, CT 06855, 2 beds, 2.5 baths

$999,000

2 beds2.5 baths2,116 sq ft

189 East Ave, Norwalk, CT 06855

Property at 212 Denver Ave, Bridgeport, CT 06605, 5 beds, 2 baths

$379,990

5 beds2 baths1,833 sq ft

212 Denver Ave, Bridgeport, CT 06605

Property at 3 John St, Greenwich, CT 06831, 3 beds, 2.5 baths

$1,750,000

3 beds2.5 baths2,906 sq ft

3 John St, Greenwich, CT 06831

Property at 155 Moody Ave, Fairfield, CT 06825, 3 beds, 1.5 baths

$509,500

3 beds1.5 baths1,510 sq ft

155 Moody Ave, Fairfield, CT 06825

Property at 65 Clearview Dr, Bridgeport, CT 06606, 3 beds, 2 baths

$550,000

3 beds2 baths1,633 sq ft

65 Clearview Dr, Bridgeport, CT 06606

Property at 41 Baxter Dr, Norwalk, CT 06854, 4 beds, 2.5 baths

$620,000

4 beds2.5 baths1,659 sq ft

41 Baxter Dr, Norwalk, CT 06854

Property at 1867 Main St, Stratford, CT 06615, 6 beds, 2 baths

$799,900

6 beds2 baths3,725 sq ft

1867 Main St, Stratford, CT 06615

Property at 88 Brewster St, Stratford, CT 06614, 3 beds, 2 baths

$575,000

3 beds2 baths2,105 sq ft

88 Brewster St, Stratford, CT 06614

Property at 13 School St, Monroe, CT 06468, 3 beds, 2 baths

$649,900

3 beds2 baths1,638 sq ft

13 School St, Monroe, CT 06468

Property at 1922 Boston Ave, Bridgeport, CT 06610, 10 beds, 4 baths

$700,000

10 beds4 baths2,988 sq ft

1922 Boston Ave, Bridgeport, CT 06610

Property at 581 California St, Stratford, CT 06614, 3 beds, 2 baths

$474,900

3 beds2 baths1,502 sq ft

581 California St, Stratford, CT 06614

Property at 419 Huntington Rd, Stratford, CT 06614, 4 beds, 2.5 baths

$499,900

4 beds2.5 baths1,860 sq ft

419 Huntington Rd, Stratford, CT 06614

Property at 30 Winfield Dr, Stratford, CT 06615, 3 beds, 1 bath

$459,000

3 beds1 bath1,354 sq ft

30 Winfield Dr, Stratford, CT 06615

Property at 381 W Mountain Rd, Ridgefield, CT 06877, 5 beds, 3.5 baths

$1,374,000

5 beds3.5 baths3,938 sq ft

381 W Mountain Rd, Ridgefield, CT 06877

Property at 37 Rowsley St #6, Bridgeport, CT 06605, 1 bed, 1 bath

$194,900

1 bed1 bath755 sq ft

37 Rowsley St #6, Bridgeport, CT 06605

Property at 25 Topstone Dr, Danbury, CT 06810, 2 beds, 1 bath

$389,000

2 beds1 bath936 sq ft

25 Topstone Dr, Danbury, CT 06810

Property at 9 Mountainville Rd, Danbury, CT 06810, 5 beds, 2 baths

$599,000

5 beds2 baths2,287 sq ft

9 Mountainville Rd, Danbury, CT 06810

Property at 30 Sherman Ave, Greenwich, CT 06830, 3 beds, 1.5 baths

$869,000

3 beds1.5 baths1,699 sq ft

30 Sherman Ave, Greenwich, CT 06830

Property at 105 Asylum St, Bridgeport, CT 06610, 8 beds, 3 baths

$649,900

8 beds3 baths2,530 sq ft

105 Asylum St, Bridgeport, CT 06610

Property at 274 Park St, Bridgeport, CT 06608, 4 beds, 2 baths

$575,000

4 beds2 baths3,097 sq ft

274 Park St, Bridgeport, CT 06608

Property at 217 Huntington Rd, Stratford, CT 06614, 3 beds, 3 baths

$699,000

3 beds3 baths2,888 sq ft

217 Huntington Rd, Stratford, CT 06614

Property at 7 Renzulli Rd, Norwalk, CT 06851, 3 beds, 3 baths

$1,500,000

3 beds3 baths2,822 sq ft

7 Renzulli Rd, Norwalk, CT 06851

Viewing page 3 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.