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

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ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to this sunny and spacious colonial located in the heart of Fairfield! This totally renovated house is everything you would wish for to call it home. Newer kitchen with quartz countertop and appliances, newer bathrooms, newer hardwood floors on main level, newer carpet on second level, newer siding, newer roof, newer central air/ HVAC unit, and so much more to list. 5 bedrooms with an additional small room that can be used as a guest room, office, or play den. The spacious family room has a slider door that leads to a generous sized deck that overlooks the yard and is ready for you to host your family and friends gathering for a BBQ! BONUS walk out partially finished basement that c

$790,000

5 beds2 baths2,400 sq ft

127 Jennings Rd, Fairfield, CT 06825

Quartz countertop • Newer kitchen • Newer siding

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
WELCOME HOME to this well-maintained property featuring an updated kitchen and bathroom, updated windows and durable vinyl siding. The spacious primary bedroom and all bedrooms offer ceiling lights and closets with lights. Also, an oversized 2nd floor linen closet. Enjoy the beautiful hardwood floors through-out the home complimented by a tiled kitchen floor and tiled bathroom. Step outside to a peaceful, private backyard, perfect for relaxing and entertaining. Located on a sidewalk-lined street surrounded by well-kept homes, this property offers comfort, updates, and a welcoming neighborhood setting with public utilities,

$489,900

3 beds1 bath1,352 sq ft

75 Westville Ave, Danbury, CT 06810

Ceiling lights • Durable vinyl siding • Closets with lights

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 10 Prospect Drive, a charming Stratford home offering character, flexibility, and a convenient location. Set in an established neighborhood, this home features a versatile layout with comfortable living spaces and plenty of opportunity to make it your own. A standout feature is the flexible first-floor room, previously used by the seller as a primary bedroom and by past owners as a formal dining room. Whether you need a main-level bedroom, dining room, home office, or additional living space, this room can easily adapt to your needs. Adding to the home's character is its connection to Stratford's local history. Per the seller, homes in the neighborhood were originally built for G

$449,000

4 beds1.5 baths1,222 sq ft

10 Prospect Dr, Stratford, CT 06615

Train access • Near shopping dining • Area amenities

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 148 Ripton Road, a fully renovated 1920 Colonial in Shelton's sought-after Huntington neighborhood, where classic New England character meets a bright, open, modern layout. Completely redone with virtually everything replaced, this home offers approx. 2,470 sq ft of living space across three finished levels on a level, open 0.76-acre lot. The heart of the home is a showpiece kitchen with a soaring vaulted ceiling, custom white shaker cabinetry, black granite counters, open shelving and a full stainless steel appliance package, flowing into the dining and living areas for easy everyday living and entertaining. Gleaming hardwood floors run throughout. A first-floor office and an up

$619,900

3 beds1.5 baths2,470 sq ft

148 Ripton Rd, Shelton, CT 06484

Fully renovated • Showpiece kitchen • Vaulted ceiling

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
This well-maintained 5-bedroom, 2-full-bath home at 1885 Old Town Rd offers approximately 1,831 square feet of living space, including the basement area. The property features natural gas, city water, and city sewer, with a new water heater installed in 2026. Currently rented for $4,500 per month through May 31, 2027, the home offers immediate rental income for the current owner while providing flexibility for the next owner. Whether you're looking for an income-producing property, considering future owner occupancy, or looking for an opportunity to increase rental income over time, this property offers several possibilities. Ideally located in Bridgeport's North End, the home is close to

$510,000

3 beds1.5 baths1,092 sq ft

1885 Old Town Rd, Bridgeport, CT 06606

6,969 sq ft lot • Built 1960 • Listed 7 days

Property at 50 Vine St, Stratford, CT 06614, 3 beds, 1.5 baths

$479,000

3 beds1.5 baths1,857 sq ft

50 Vine St, Stratford, CT 06614

Property at 97 Meadowpark Ave N, Stamford, CT 06905, 4 beds, 2.5 baths

$1,395,000

4 beds2.5 baths4,538 sq ft

97 Meadowpark Ave N, Stamford, CT 06905

Property at 135 Plymouth St, Stratford, CT 06614, 3 beds, 2 baths

$565,000

3 beds2 baths1,985 sq ft

135 Plymouth St, Stratford, CT 06614

Property at 354 Oaklawn Ave, Stamford, CT 06905, 4 beds, 3.5 baths

$1,799,000

4 beds3.5 baths6,503 sq ft

354 Oaklawn Ave, Stamford, CT 06905

Property at 50 Cody Dr, Stamford, CT 06905, 4 beds, 3 baths

$1,050,000

4 beds3 baths2,180 sq ft

50 Cody Dr, Stamford, CT 06905

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 111 Mercer St, Stratford, CT 06614, 3 beds, 2.5 baths

$499,900

3 beds2.5 baths1,870 sq ft

111 Mercer St, Stratford, CT 06614

Property at 44 Lavelle Ave, New Fairfield, CT 06812, 1 bed, 1 bath

$399,999

1 bed1 bath789 sq ft

44 Lavelle Ave, New Fairfield, CT 06812

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 145 Dewey St, Stratford, CT 06615, 5 beds, 5 baths

$749,900

5 beds5 baths3,219 sq ft

145 Dewey St, Stratford, CT 06615

Property at 9 Seaside Pl, Norwalk, CT 06855, 5 beds, 2 baths

$1,999,999

5 beds2 baths2,809 sq ft

9 Seaside Pl, Norwalk, CT 06855

Property at 77 Ridge Rd, Stratford, CT 06614, 4 beds, 2.5 baths

$625,000

4 beds2.5 baths2,700 sq ft

77 Ridge Rd, Stratford, CT 06614

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 175 Eaton St, Bridgeport, CT 06604, 3 beds, 1.5 baths

$489,000

3 beds1.5 baths2,000 sq ft

175 Eaton St, Bridgeport, CT 06604

Property at 421 Wakelee Ave, Stratford, CT 06614, 3 beds, 2 baths

$450,000

3 beds2 baths1,442 sq ft

421 Wakelee Ave, Stratford, CT 06614

Property at 1 Willowbrook Ct #1, Stamford, CT 06902, 2 beds, 1.5 baths

$405,000

2 beds1.5 baths907 sq ft

1 Willowbrook Ct #1, Stamford, CT 06902

Property at 120 Howe Ave, Shelton, CT 06484, 3 beds, 1.5 baths

$449,900

3 beds1.5 baths1,670 sq ft

120 Howe Ave, Shelton, CT 06484

Property at 105 Washington Pkwy, Stratford, CT 06615, 4 beds, 2 baths

$685,000

4 beds2 baths2,298 sq ft

105 Washington Pkwy, Stratford, CT 06615

Property at 251 Bridge St #251, Stamford, CT 06905, 2 beds, 2 baths

$399,000

2 beds2 baths1,872 sq ft

251 Bridge St #251, Stamford, CT 06905

Property at 23 Longview Dr, Brookfield, CT 06804, 2 beds, 1 bath

$485,000

2 beds1 bath1,101 sq ft

23 Longview Dr, Brookfield, CT 06804

Property at 1991 Old Town Rd, Bridgeport, CT 06606, 5 beds, 2 baths

$495,000

5 beds2 baths1,786 sq ft

1991 Old Town Rd, Bridgeport, CT 06606

Property at 23 Park Ln, Norwalk, CT 06854, 4 beds, 3.5 baths

$1,995,000

4 beds3.5 baths2,760 sq ft

23 Park Ln, Norwalk, CT 06854

Property at 94 Soundview Rd, Ridgefield, CT 06877, 5 beds, 4.5 baths

$2,200,000

5 beds4.5 baths4,592 sq ft

94 Soundview Rd, Ridgefield, CT 06877

Property at 391 Court D, Building 51, Bridgeport, CT 06610, 2 beds, 1 bath

$84,250

2 beds1 bath662 sq ft

391 Court D, Building 51, Bridgeport, CT 06610

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 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 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 6 Vanderbilt Ave, Norwalk, CT 06854, 4 beds, 2 baths

$995,000

4 beds2 baths1,452 sq ft

6 Vanderbilt Ave, Norwalk, CT 06854

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 71 School St, Fairfield, CT 06824, 2 beds, 1 bath

$599,900

2 beds1 bath941 sq ft

71 School St, Fairfield, CT 06824

Property at 155 Long Neck Point Rd, Darien, CT 06820, 10 beds, 10.5 baths

$16,495,000

10 beds10.5 baths11,944 sq ft

155 Long Neck Point Rd, Darien, CT 06820

Property at 10 Crown St, Trumbull, CT 06611, 3 beds, 1.5 baths

$595,000

3 beds1.5 baths1,840 sq ft

10 Crown St, Trumbull, CT 06611

Property at 39 Walter Ave, Norwalk, CT 06851, 4 beds, 2 baths

$715,000

4 beds2 baths1,802 sq ft

39 Walter Ave, Norwalk, CT 06851

Property at 580 Lake Ave, Greenwich, CT 06830, 6 beds, 7.5 baths

$5,745,000

6 beds7.5 baths6,878 sq ft

580 Lake Ave, Greenwich, CT 06830

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 845 Kings Hwy W, Fairfield, CT 06825, 3 beds, 2.5 baths

$1,645,000

3 beds2.5 baths2,074 sq ft

845 Kings Hwy W, Fairfield, CT 06825

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Based on information submitted to the MLS GRID as of Mon Oct 12 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 857 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, 750 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 893 condos, 1 townhouse, and 216 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.

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