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:
Completely reimagined and renovated, this exceptional home offers breathtaking lake views and high-end upgrades throughout. Recent improvements include new siding, a new architectural roof, new hardwood flooring, custom kitchen cabinetry, a new electric heat pump HVAC system, upgraded electrical service, and a new septic system. The dramatic vaulted living room features a stunning floor-to-ceiling stone fireplace, creating a warm and inviting focal point. Outdoor living is second to none with a spacious mahogany deck showcasing sleek black railings, multiple access points, and plenty of room for entertaining, dining, or simply enjoying the panoramic water views. A beautiful stone patio prov

$699,999

2 beds1 bath768 sq ft

2 Longview Dr, Brookfield, CT 06804

New siding • Lake views • 6,969 sq ft lot

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

$649,900

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:
Attention Investors, Contractors & Flippers! Excellent opportunity in a desirable and sought-after area! This 3-bedroom, 3-bath home with a detached 2-car garage is already halfway through the renovation process, giving the next owner a great head start. Much of the heavy work has already been completed, including all demolition, new electrical wiring, and most of the new plumbing. Now it's ready for someone with vision to step in, complete the renovation, and bring this property back to liThe seller originally intended to finish the project but became involved in a larger renovation project and simply does not have the time to complete this one. A great opportunity for an investor, c

$549,900

3 beds1.5 baths1,090 sq ft

33 Melville Ave, Fairfield, CT 06825

5,227 sq ft lot • 2 garage spots • Built 1924

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to easy living in one of Stratford's most convenient locations! This beautifully maintained Ranch offers the perfect combination of comfort, privacy, and accessibility. Enjoy a spacious, nearly double-sized private yard and an oversized patio-perfect for entertaining, summer gatherings, or simply relaxing outdoors. Ideally located just minutes from Short Beach Park and Long Island Sound, with easy access to the Housatonic River, Metro-North train station, I-95, shopping, dining, and everyday conveniences. The home has been lovingly maintained and is ready for its next owner to add their personal touches and make it their own. Whether you're enjoying peaceful days at home, entertaini

$550,000

3 beds1.5 baths1,454 sq ft

1680 Main St, Stratford, CT 06615

Long island sound • Short beach park • Oversized patio

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Huge rare find! This impressive 4,590 sq. ft. 3-family property offers incredible versatility with zoning that allows for residential, commercial, or mixed-use possibilities. The property features three separate units, a detached 5-car garage, and a spacious driveway with plenty of parking. The first-floor unit is currently set up as an insurance office and offers a living room, eat-in kitchen with laundry area, 3 bedrooms, and an updated full bath. The second-floor unit features a spacious living room, dining room, eat-in kitchen with laundry area, 3 bedrooms, an updated full bath, and an enclosed porch. The entire third floor has been completely gutted, with all electrical and plumbing in

$725,000

8 beds3 baths4,590 sq ft

1757 E Main St, Bridgeport, CT 06610

Updated full bath • Enclosed porch • Spacious driveway

Property at 200 Griffin Ave, Bridgeport, CT 06606, 5 beds, 2 baths

$650,000

5 beds2 baths1,423 sq ft

200 Griffin Ave, Bridgeport, CT 06606

Property at 164 Virginia Ave Unit B, Bridgeport, CT 06610, 1 bed, 1 bath

$129,900

1 bed1 bath650 sq ft

164 Virginia Ave Unit B, Bridgeport, CT 06610

Property at 57-59 West St, Danbury, CT 06810, 9 beds, 6 baths

$1,399,000

9 beds6 baths5,338 sq ft

57-59 West St, Danbury, CT 06810

Property at 60 Boston Ter, Bridgeport, CT 06610, 3 beds, 1.5 baths

$449,999

3 beds1.5 baths2,054 sq ft

60 Boston Ter, Bridgeport, CT 06610

$489,900

4 beds2.5 baths1,710 sq ft

276 Nichols Ter, Stratford, CT 06614

$649,900

6 beds3 baths3,021 sq ft

438 Hollister Ave, Bridgeport, CT 06607

Property at 267 Westport Rd, Wilton, CT 06897, 4 beds, 4 baths

$1,595,000

4 beds4 baths5,335 sq ft

267 Westport Rd, Wilton, CT 06897

Property at 58 Sheephill Rd, Riverside, CT 06878, 4 beds, 4 baths

$1,850,000

4 beds4 baths2,899 sq ft

58 Sheephill Rd, Riverside, CT 06878

Property at 88 Indian Field Rd, Greenwich, CT 06830, 5 beds, 4 baths

$2,650,000

5 beds4 baths3,464 sq ft

88 Indian Field Rd, Greenwich, CT 06830

Property at 38 Guyer Rd, Westport, CT 06880, 4 beds, 2 baths

$1,399,000

4 beds2 baths1,665 sq ft

38 Guyer Rd, Westport, CT 06880

Property at 9 Keplers Way, New Fairfield, CT 06812, 2 beds, 1.5 baths

$349,000

2 beds1.5 baths902 sq ft

9 Keplers Way, New Fairfield, CT 06812

Property at 90 Weed Hill Ave, Stamford, CT 06907, 2 beds, 1 bath

$439,000

2 beds1 bath1,170 sq ft

90 Weed Hill Ave, Stamford, CT 06907

Property at 383 High Ridge Rd, Fairfield, CT 06825, 2 beds, 2 baths

$699,999

2 beds2 baths2,335 sq ft

383 High Ridge Rd, Fairfield, CT 06825

Property at 53 Cross Hwy, Westport, CT 06880, 3 beds, 2 baths

$1,000,000

3 beds2 baths1,400 sq ft

53 Cross Hwy, Westport, CT 06880

Property at 17 Driftwood Ln, Norwalk, CT 06851, 4 beds, 2 baths

$949,000

4 beds2 baths3,502 sq ft

17 Driftwood Ln, Norwalk, CT 06851

Property at 121 Parry Rd, Stamford, CT 06907, 5 beds, 3.5 baths

$1,450,000

5 beds3.5 baths4,177 sq ft

121 Parry Rd, Stamford, CT 06907

Property at 27 White Oak Shade Ln, New Canaan, CT 06840, 4 beds, 3 baths

$1,499,000

4 beds3 baths2,478 sq ft

27 White Oak Shade Ln, New Canaan, CT 06840

Property at 27 Rayfield Rd, Westport, CT 06880, 3 beds, 4 baths

$1,800,000

3 beds4 baths3,104 sq ft

27 Rayfield Rd, Westport, CT 06880

Property at 5 Cross Rd, Darien, CT 06820, 4 beds, 4 baths

$3,795,000

4 beds4 baths4,361 sq ft

5 Cross Rd, Darien, CT 06820

Property at 172 Hope St, Stamford, CT 06906, 3 beds, 2 baths

$565,000

3 beds2 baths1,358 sq ft

172 Hope St, Stamford, CT 06906

Property at 107 Maple Ave, Greenwich, CT 06830, 5 beds, 7.5 baths

$8,800,000

5 beds7.5 baths6,637 sq ft

107 Maple Ave, Greenwich, CT 06830

Property at 15 Brooklawn Ave, Stamford, CT 06906, 3 beds, 1.5 baths

$749,000

3 beds1.5 baths1,958 sq ft

15 Brooklawn Ave, Stamford, CT 06906

Property at 4438 Madison Ave, Trumbull, CT 06611, 3 beds, 3 baths

$550,000

3 beds3 baths2,184 sq ft

4438 Madison Ave, Trumbull, CT 06611

Property at 2493 Redding Rd, Fairfield, CT 06824, 5 beds, 5 baths

$2,395,000

5 beds5 baths5,415 sq ft

2493 Redding Rd, Fairfield, CT 06824

Property at 999 Bronson Rd, Fairfield, CT 06824, 4 beds, 2.5 baths

$1,949,000

4 beds2.5 baths2,670 sq ft

999 Bronson Rd, Fairfield, CT 06824

Property at 303 Bruce Ave, Stratford, CT 06614, 4 beds, 2 baths

$300,000

4 beds2 baths1,448 sq ft

303 Bruce Ave, Stratford, CT 06614

Property at 13 Chestnut St, Darien, CT 06820, 4 beds, 3 baths

$1,895,000

4 beds3 baths2,303 sq ft

13 Chestnut St, Darien, CT 06820

Property at 11 Oldfield Dr, Fairfield, CT 06824, 4 beds, 2 baths

$1,195,000

4 beds2 baths2,124 sq ft

11 Oldfield Dr, Fairfield, CT 06824

Property at 8 Somerset Ln, Riverside, CT 06878, 6 beds, 6.5 baths

$5,295,000

6 beds6.5 baths5,278 sq ft

8 Somerset Ln, Riverside, CT 06878

Property at 19 Weed Ave, Norwalk, CT 06850, 3 beds, 1.5 baths

$565,000

3 beds1.5 baths1,392 sq ft

19 Weed Ave, Norwalk, CT 06850

Property at 39 Sorghum Rd, Shelton, CT 06484, 3 beds, 3 baths

$639,999

3 beds3 baths2,442 sq ft

39 Sorghum Rd, Shelton, CT 06484

Property at 47 Purdy Rd E, Norwalk, CT 06850, 4 beds, 2.5 baths

$765,000

4 beds2.5 baths1,782 sq ft

47 Purdy Rd E, Norwalk, CT 06850

Property at 207 Redding Rd, Redding, CT 06896, 4 beds, 2 baths

$1,099,000

4 beds2 baths3,124 sq ft

207 Redding Rd, Redding, CT 06896

Property at 143 Chestnut Hill Rd, Wilton, CT 06897, 6 beds, 5.5 baths

$2,375,000

6 beds5.5 baths5,455 sq ft

143 Chestnut Hill Rd, Wilton, CT 06897

Property at 61 Putnam Park #61, Greenwich, CT 06830, 3 beds, 2 baths

$700,000

3 beds2 baths1,250 sq ft

61 Putnam Park #61, Greenwich, CT 06830

Property at 128 Linley Dr, Fairfield, CT 06825, 3 beds, 3 baths

$1,195,000

3 beds3 baths2,169 sq ft

128 Linley Dr, Fairfield, CT 06825

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Based on information submitted to the MLS GRID as of Thu Oct 08 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 842 vintage homes for sale in Fairfield County at a median listing price of $700K. 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, 747 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 892 condos, 1 townhouse, and 213 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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