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

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NEW 14 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Fully renovated and modernized, this farmhouse seamlessly blends historic charm with contemporary style across four finished levels. The 4-bedroom, 2-bath home features exposed brick, red fir floors, cherry cabinetry, elegant Brazilian granite and a pantry. The primary suite boasts vaulted ceilings, custom birch closets and a slate double shower. A walk-out lower level offers additional finished space, built-in homework stations and a media room. Additional highlights include whole-home water filtration, kitchen reverse osmosis, an expansive deck, generous green space, a long driveway and potential for an ADU. Near Byram Park's sandy beach, marina, tennis courts, playground, pool and splash

$1,195,000

4 beds2 baths1,684 sq ft

351 Delavan Ave, Greenwich, CT 06830

Pantry • Exposed brick • Brazilian granite

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 271 Success Ave #271 in Bridgeport! This move-in-ready 2-bedroom, 1-bath townhouse offers comfortable living with a functional layout featuring a kitchen and inviting living room. Enjoy the convenience of a low-maintenance lifestyle, with common fees including heat, hot water, exterior maintenance, trash removal, property taxes, and insurance. A great opportunity for comfortable and convenient living.

$72,500

2 beds1 bath622 sq ft

271 Success Ave #271, Bridgeport, CT 06610

$568 HOA • Built 1943 • Listed 7 days

NEW 20 MINS AGO

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 70 Trumbull Avenue, a beautifully appointed single-family home situated in Bridgeport's desirable North End! Offering 4 bedrooms, 3 full bathrooms, and approximately 1,750 square feet of living space, this property combines comfort, functionality, and modern finishes. Step inside to discover an inviting living room, a dedicated dining area, and a spacious kitchen featuring quartz countertops, stainless steel appliances, white cabinetry, and a center island perfect for everyday living and entertaining. The thoughtfully designed layout offers versatile living spaces, while the finished basement provides additional room for recreation, a home office, or other flexible uses. Outside,

$525,000

4 beds3 baths1,750 sq ft

70 Trumbull Ave, Bridgeport, CT 06606

4,791 sq ft lot • Built 1957

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to this charming ranch-style home in the highly desirable St. Mary's-by-the-Sea section of Black Rock. Offering easy one-level living, this well-appointed residence features three bedrooms, two full bathrooms, and a spacious living room filled with natural light from large windows. Hardwood floors add warmth to the living room, dining room, and inviting sunroom, which overlooks the mature gardens and offers beautiful sunset views. The kitchen features granite countertops, a cooktop, wall oven, and breakfast bar. A main-level laundry room adds everyday convenience. One full bathroom has been thoughtfully updated, while the second retains its original character. Enjoy the outdoors fro

$995,000

3 beds2 baths1,926 sq ft

265 Balmforth St, Bridgeport, CT 06605

Mature gardens • Inviting sunroom • Natural light

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Nestled on a picturesque stretch of bucolic Turtleback Road-a long-time favorite route for local walkers-this inviting 3-bedroom, 2-bathroom ranch offers a rare connection to Wilton's historic pastoral roots. Once part of a cherished local dairy farm, the property carries a peaceful, storied atmosphere that's hard to find. Inside, the home feels bright, refreshed, and rejuvenated, boasting beautiful refinished hardwood floors and a fresh coat of paint throughout an effortless, single-level layout. While the interior shines, the view out of every window truly steals the show. The property backs directly onto expansive woodlands, offering easy access to miles of hiking leading to the historic

$899,000

3 beds2 baths2,662 sq ft

84 Turtleback Rd, Wilton, CT 06897

Covered parking • Miles of hiking • Expansive woodlands

Property at 6 Meadow Brook Rd, Newtown, CT 06470, 3 beds, 1 bath

$665,000

3 beds1 bath1,928 sq ft

6 Meadow Brook Rd, Newtown, CT 06470

Property at 3 Topping Ln, Norwalk, CT 06854, 3 beds, 2.5 baths

$825,000

3 beds2.5 baths1,342 sq ft

3 Topping Ln, Norwalk, CT 06854

Property at 73 Yale St, Bridgeport, CT 06605, 5 beds, 3 baths

$570,000

5 beds3 baths3,044 sq ft

73 Yale St, Bridgeport, CT 06605

Property at 144 Colonial Rd, Stamford, CT 06906, 4 beds, 2 baths

$904,999

4 beds2 baths2,880 sq ft

144 Colonial Rd, Stamford, CT 06906

Property at 383 Harral Ave, Bridgeport, CT 06604, 9 beds, 3 baths

$859,900

9 beds3 baths2,982 sq ft

383 Harral Ave, Bridgeport, CT 06604

Property at 1046 Sylvan Ave, Bridgeport, CT 06606, 4 beds, 2 baths

$430,000

4 beds2 baths1,586 sq ft

1046 Sylvan Ave, Bridgeport, CT 06606

Property at 16 Winfield Ct, Norwalk, CT 06855, 3 beds, 1.5 baths

$575,000

3 beds1.5 baths1,396 sq ft

16 Winfield Ct, Norwalk, CT 06855

Property at 127 Lake Ave, Greenwich, CT 06830, 4 beds, 3 baths

$1,495,000

4 beds3 baths1,822 sq ft

127 Lake Ave, Greenwich, CT 06830

Property at 7 Idlewild Mnr, Greenwich, CT 06830, 2 beds, 1 bath

$2,000,000

2 beds1 bath783 sq ft

7 Idlewild Mnr, Greenwich, CT 06830

Property at 27 Sachem Ln, Greenwich, CT 06830, 5 beds, 3 baths

$2,195,000

5 beds3 baths2,688 sq ft

27 Sachem Ln, Greenwich, CT 06830

Property at 27 Lakeside Ave, Darien, CT 06820, 3 beds, 3 baths

$1,649,000

3 beds3 baths2,007 sq ft

27 Lakeside Ave, Darien, CT 06820

Property at 78 & 92 Pastures Ln, New Canaan, CT 06840, 7 beds, 7 baths

$9,250,000

7 beds7 baths9,573 sq ft

78 & 92 Pastures Ln, New Canaan, CT 06840

Property at 753 Den Rd, Stamford, CT 06903, 3 beds, 2.5 baths

$980,000

3 beds2.5 baths1,856 sq ft

753 Den Rd, Stamford, CT 06903

Property at 59 Stanwich Rd, Greenwich, CT 06830, 4 beds, 3 baths

$1,850,000

4 beds3 baths2,365 sq ft

59 Stanwich Rd, Greenwich, CT 06830

Property at 29 S Lake Dr, Stamford, CT 06903, 4 beds, 3.5 baths

$1,799,000

4 beds3.5 baths3,247 sq ft

29 S Lake Dr, Stamford, CT 06903

Property at 20 Fulton Dr, New Fairfield, CT 06812, 4 beds, 2 baths

$499,999

4 beds2 baths1,570 sq ft

20 Fulton Dr, New Fairfield, CT 06812

Property at 108 Good Hill Rd, Weston, CT 06883, 6 beds, 3.5 baths

$1,750,000

6 beds3.5 baths4,346 sq ft

108 Good Hill Rd, Weston, CT 06883

Property at 18 Maple St, Trumbull, CT 06611, 4 beds, 3 baths

$719,000

4 beds3 baths1,019 sq ft

18 Maple St, Trumbull, CT 06611

Property at 6 Berry Ln, Darien, CT 06820, 6 beds, 3 baths

$5,025,000

6 beds3 baths4,477 sq ft

6 Berry Ln, Darien, CT 06820

Property at 280 Main St, Westport, CT 06880, 3 beds, 2.5 baths

$1,199,000

3 beds2.5 baths1,936 sq ft

280 Main St, Westport, CT 06880

Property at 363 State Route 37, New Fairfield, CT 06812, 4 beds, 2 baths

$599,000

4 beds2 baths2,838 sq ft

363 State Route 37, New Fairfield, CT 06812

Property at 151 Stanwich Rd, Greenwich, CT 06830, 5 beds, 4.5 baths

$4,795,000

5 beds4.5 baths4,870 sq ft

151 Stanwich Rd, Greenwich, CT 06830

Property at 160 Olmstead Hill Rd, Wilton, CT 06897, 4 beds, 3 baths

$1,899,000

4 beds3 baths3,282 sq ft

160 Olmstead Hill Rd, Wilton, CT 06897

Property at 15 Potter Dr, Old Greenwich, CT 06870, 4 beds, 3.5 baths

$3,400,000

4 beds3.5 baths3,418 sq ft

15 Potter Dr, Old Greenwich, CT 06870

Property at 467 Nod Hill Rd, Wilton, CT 06897, 3 beds, 2.5 baths

$1,295,000

3 beds2.5 baths1,883 sq ft

467 Nod Hill Rd, Wilton, CT 06897

Property at 20 Church St Unit B31, Greenwich, CT 06830, 3 beds, 3 baths

$2,195,000

3 beds3 baths2,060 sq ft

20 Church St Unit B31, Greenwich, CT 06830

Property at 205 Castle Ave, Fairfield, CT 06825, 3 beds, 1.5 baths

$550,000

3 beds1.5 baths1,344 sq ft

205 Castle Ave, Fairfield, CT 06825

Property at 363 State Route 37 Ct, New Fairfield, CT 06812, 4 beds, 2 baths

$599,000

4 beds2 baths2,838 sq ft

363 State Route 37 Ct, New Fairfield, CT 06812

Coldwell Banker Realty

Property at 40 Ogden Rd, New Canaan, CT 06840, 3 beds, 1 bath

$1,049,000

3 beds1 bath1,450 sq ft

40 Ogden Rd, New Canaan, CT 06840

Property at 1 Clearview Ave, Bethel, CT 06801, 3 beds, 2 baths

$550,000

3 beds2 baths1,879 sq ft

1 Clearview Ave, Bethel, CT 06801

Property at 5 Arden Rd, Trumbull, CT 06611, 3 beds, 2 baths

$650,000

3 beds2 baths2,688 sq ft

5 Arden Rd, Trumbull, CT 06611

Property at 1 Villaway Rd, Norwalk, CT 06855, 3 beds, 2 baths

$649,000

3 beds2 baths1,972 sq ft

1 Villaway Rd, Norwalk, CT 06855

Property at 81 Lakeside Dr, Ridgefield, CT 06877, 3 beds, 3 baths

$825,000

3 beds3 baths2,754 sq ft

81 Lakeside Dr, Ridgefield, CT 06877

Property at 25 Tremont Ave, Stamford, CT 06906, 4 beds, 2.5 baths

$875,000

4 beds2.5 baths2,380 sq ft

25 Tremont Ave, Stamford, CT 06906

Property at 140 Beardsley Park Ter, Bridgeport, CT 06610, 3 beds, 1 bath

$370,500

3 beds1 bath1,280 sq ft

140 Beardsley Park Ter, Bridgeport, CT 06610

Property at 253 Shore Rd, Greenwich, CT 06830, 8 beds, 4.5 baths

$5,650,000

8 beds4.5 baths6,522 sq ft

253 Shore Rd, Greenwich, CT 06830

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Based on information submitted to the MLS GRID as of Wed Oct 14 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 853 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 895 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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