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:
Tucked along a tranquil lane, mere steps from the soft sands of Westport's coveted Compo Beach, 19 Roosevelt Road is coastal living at its most refined. This picture-perfect residence of four bedrooms and three and a half baths pairs timeless elegance with effortless comfort. It was reimagined from the studs up in 2019 and is fully FEMA-compliant, with two light-filled levels and every modern convenience. On the main level, a gracious living room sets the tone, framed by custom built-in bookcases and warmed by a gas fireplace. The chef's kitchen is the heart of the home. It has a generous center island, a Sub-Zero refrigerator, a Wolf gas range and a dedicated wine refrigerator. Beyond it,

$4,250,000

4 beds3.5 baths2,762 sq ft

19 Roosevelt Rd, Westport, CT 06880

Gas fireplace • Wolf gas range • Chef's kitchen

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ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
This stone Manor is being offered for sale for only the second time in nearly 100 years. Set on an impressive lot, 60 Broadbridge Road offers the space and character that make a classic Colonial feel like home. Pull into your level driveway and attached garage-no scraping snow off the car on cold New England mornings or getting soaked bringing in the groceries. Step inside, where hardwood floors lead through more than 2,300 square feet. Gather around the fireplace for movie nights, holiday mornings and quiet winter evenings. Even better, a main-level primary suite means no stairs and offers tremendous flexibility for a large family, overnight guests or grandparents who want their own comfor

$629,900

4 beds2.5 baths3,282 sq ft

60 Broadbridge Rd, Bridgeport, CT 06610

Attached garage • Level driveway • Enlarged patios

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
4 Bedroom Single Family Cape Style Home Located in Mill Hill Neighborhood in Excellent Condition, Eat in Kitchen, Partially Finished Basement, Solar Panels, 2 Car Detached Garage, Large Back Yard. New Heating System and Water Heater. Convenient to I-95, Bus Line, and 10-Minute Drive to Metro North Train Station. 4 Bedroom Single Family Cape Style Home Located in Mill Hill Neighborhood in Excellent Condition, Eat in Kitchen, Partially Finished Basement, Solar Panels, 2 Car Detached Garage, Large Back Yard. New Heating System and Water Heater. Convenient to I-95, Bus Line, and 10-Minute Drive to Metro North Train Station.

$469,500

4 beds1 bath1,152 sq ft

216 Granfield Ave, Bridgeport, CT 06610

Eat in kitchen • Large back yard • Solar panels

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Beautiful 2-bedroom townhouse corner unit with a large eat-in kitchen, plenty of cabinets and counter space, Gas Range, Washer & Dryer, Porch. Hardwood floors throughout, finished basement, walk-up attic, water heater and main circuit breaker installed in 2020, sump pump installed in 2026, Water and Sewer included in HOA, Great location near the Library and Park, Basketball Court, Beach, Shopping/Mall, Beasley Zoo, Saint Mary By The Sea, Captain's Cove Seaport and Public Transportation. Why rent when you can own your own home? Must see!!! Preferred Conventional Mortgage

$230,000

2 beds1 bath948 sq ft

120 Virginia Ave #120, Bridgeport, CT 06610

Water heater • Washer & dryer • Finished basement

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
'' THE PENTHOUSE '' just a sidewalk away from Greenwich Avenue. This nearly 4,000 sq ft residence offers a flexible layout with expansive living and dining areas, The home features open, light-filled spaces and seamless flow throughout. Enjoy sweeping views of the Long Island Sound and sunsets from multiple vantage points, plus a private roof deck ideal for outdoor entertaining. A rare opportunity combining size, close-to-town convenience, and spectacular water views in a premier location.

$7,495,000

2 beds2.5 baths3,890 sq ft

9 Lafayette Ct, Greenwich, CT 06830

Sweeping views • Flexible layout • Private roof deck

Property at 228 Woodrow Ave, Southport, CT 06890, 3 beds, 2 baths

$1,180,000

3 beds2 baths2,253 sq ft

228 Woodrow Ave, Southport, CT 06890

Property at 75 Hemlock St, Bridgeport, CT 06605, 3 beds, 2 baths

$499,900

3 beds2 baths1,300 sq ft

75 Hemlock St, Bridgeport, CT 06605

Property at 76 Peaceable St, Redding, CT 06896, 3 beds, 3.5 baths

$1,400,000

3 beds3.5 baths2,400 sq ft

76 Peaceable St, Redding, CT 06896

Property at 297 Shore Rd, Greenwich, CT 06830, 6 beds, 7 baths

$9,950,000

6 beds7 baths10,130 sq ft

297 Shore Rd, Greenwich, CT 06830

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 25 Van Buren Ave #1, Norwalk, CT 06850, 1 bed, 1 bath

$250,000

1 bed1 bath747 sq ft

25 Van Buren Ave #1, Norwalk, CT 06850

Property at 190 North St, Greenwich, CT 06830, 7 beds, 9.5 baths

$12,750,000

7 beds9.5 baths12,176 sq ft

190 North St, Greenwich, CT 06830

Property at 600 Brooklawn Ave, Bridgeport, CT 06604, 5 beds, 4 baths

$925,000

5 beds4 baths3,913 sq ft

600 Brooklawn Ave, Bridgeport, CT 06604

Property at 145 Canal St #503, Shelton, CT 06484, 2 beds, 2 baths

$284,900

2 beds2 baths1,050 sq ft

145 Canal St #503, Shelton, CT 06484

Property at 51 Maher Dr, Norwalk, CT 06850, 3 beds, 1.5 baths

$699,900

3 beds1.5 baths1,076 sq ft

51 Maher Dr, Norwalk, CT 06850

Property at 71 Country Rd, Fairfield, CT 06824, 3 beds, 3 baths

$879,000

3 beds3 baths1,939 sq ft

71 Country Rd, Fairfield, CT 06824

Property at 105 Old Dike Rd, Trumbull, CT 06611, 4 beds, 2 baths

$875,000

4 beds2 baths2,376 sq ft

105 Old Dike Rd, Trumbull, CT 06611

Property at 49 Sunrise Ave, Trumbull, CT 06611, 4 beds, 3 baths

$850,000

4 beds3 baths1,968 sq ft

49 Sunrise Ave, Trumbull, CT 06611

Property at 23 Clara Dr, Norwalk, CT 06851, 3 beds, 2 baths

$799,000

3 beds2 baths1,824 sq ft

23 Clara Dr, Norwalk, CT 06851

Property at 99 William St Unit B, Bridgeport, CT 06608, 3 beds, 1.5 baths

$179,900

3 beds1.5 baths1,121 sq ft

99 William St Unit B, Bridgeport, CT 06608

Property at 307 Courtland Ave, Stamford, CT 06906, 3 beds, 1 bath

$625,000

3 beds1 bath1,353 sq ft

307 Courtland Ave, Stamford, CT 06906

Property at 1285 Hope St #12, Stamford, CT 06907, 2 beds, 1 bath

$429,000

2 beds1 bath800 sq ft

1285 Hope St #12, Stamford, CT 06907

Property at 17 Fire Hill Rd, Ridgefield, CT 06877, 3 beds, 2 baths

$685,000

3 beds2 baths1,647 sq ft

17 Fire Hill Rd, Ridgefield, CT 06877

Property at 291-293 Bruce Ave, Stratford, CT 06615, 8 beds, 3 baths

$745,000

8 beds3 baths3,380 sq ft

291-293 Bruce Ave, Stratford, CT 06615

Property at 9 Reservoir St, Bethel, CT 06801, 5 beds, 2 baths

$599,000

5 beds2 baths1,584 sq ft

9 Reservoir St, Bethel, CT 06801

Property at 1 Sunrise Rd Unit B, Westport, CT 06880, 2 beds, 2.5 baths

$995,000

2 beds2.5 baths1,202 sq ft

1 Sunrise Rd Unit B, Westport, CT 06880

Property at 208 Birmingham St, Bridgeport, CT 06606, 1 bed, 1 bath

$274,900

1 bed1 bath1,149 sq ft

208 Birmingham St, Bridgeport, CT 06606

Property at 51-71 Park Ave Unit 2-51, Danbury, CT 06810, 2 beds, 1 bath

$225,000

2 beds1 bath701 sq ft

51-71 Park Ave Unit 2-51, Danbury, CT 06810

Property at 495 Cutspring Rd, Stratford, CT 06614, 4 beds, 1.5 baths

$599,000

4 beds1.5 baths1,998 sq ft

495 Cutspring Rd, Stratford, CT 06614

Property at 295 & 297 Shore Rd, Old Greenwich, CT 06830, 6 beds, 7 baths

$14,500,000

6 beds7 baths10,130 sq ft

295 & 297 Shore Rd, Old Greenwich, CT 06830

Property at 64 Garfield Ave, Danbury, CT 06810, 3 beds, 1.5 baths

$545,000

3 beds1.5 baths1,830 sq ft

64 Garfield Ave, Danbury, CT 06810

Property at 402 Patterson Ave, Stratford, CT 06614, 2 beds, 1 bath

$374,900

2 beds1 bath1,008 sq ft

402 Patterson Ave, Stratford, CT 06614

Property at 19 Topstone Dr, Bethel, CT 06801, 3 beds, 2 baths

$549,900

3 beds2 baths1,500 sq ft

19 Topstone Dr, Bethel, CT 06801

Property at 35 Beardsley Pkwy, Trumbull, CT 06611, 3 beds, 1.5 baths

$620,000

3 beds1.5 baths1,518 sq ft

35 Beardsley Pkwy, Trumbull, CT 06611

Property at 406 Lakeside Dr, Bridgeport, CT 06606, 4 beds, 2 baths

$489,999

4 beds2 baths2,227 sq ft

406 Lakeside Dr, Bridgeport, CT 06606

Property at 67 Sultan St, Stratford, CT 06614, 3 beds, 1.5 baths

$550,000

3 beds1.5 baths1,653 sq ft

67 Sultan St, Stratford, CT 06614

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

$225,000

2 beds1 bath900 sq ft

78 Haddon St #5, Bridgeport, CT 06605

Property at 62 Longmeadow Rd, Shelton, CT 06484, 4 beds, 2.5 baths

$659,000

4 beds2.5 baths2,788 sq ft

62 Longmeadow Rd, Shelton, CT 06484

Property at 110 Ruby Ln, Stratford, CT 06614, 3 beds, 1.5 baths

$469,000

3 beds1.5 baths1,548 sq ft

110 Ruby Ln, Stratford, CT 06614

Property at 235-237 Hanover St, Bridgeport, CT 06605, 6 beds, 2 baths

$575,000

6 beds2 baths2,390 sq ft

235-237 Hanover St, Bridgeport, CT 06605

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

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Based on information submitted to the MLS GRID as of Thu Oct 29 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 865 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, 754 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 900 condos, 1 townhouse, and 219 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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