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:
Set on 2.93 private acres along coveted Long Neck Point, this extraordinary waterfront Colonial offers a rare combination of sweeping water views, privacy, and direct access to the water. Spanning more than 10,000 square feet, the residence is designed to embrace its spectacular setting, with expansive living spaces and breathtaking vistas from nearly every room. The eight-bedroom main residence features seven full and three half baths, eight fireplaces, and an effortless flow between gracious entertaining spaces and comfortable everyday living. A pool and private dock extend the experience outdoors, creating an idyllic setting for waterfront living and entertaining. A charming two-bedroom,

$16,495,000

10 beds10.5 baths11,944 sq ft

155 Long Neck Point Rd, Darien, CT 06820

Waterfront colonial • Private dock • Guest cottage

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 10 Crown Street! A classic home steeped with New England charm while settling comfortably into the highly desirable Fairfield County. This very Charming Vintage Colonial has 3 bedrooms & 1.5 baths. It is situated on a perfectly level corner lot. Features include: An updated Kitchen with granite countertops. A separate Breakast Room. Living Room has a brick fireplace, built-ins, & 2 lovely stained glass decorative windows. Formal Dining Room. Family Room is carpeted & has a vaulted ceiling, skylight, built-ins, & ceiling fan. Hardwood Floors throughout. You will love the Sunroom with French doors & sliders to a wrap around deck. The upper level has 3 be

$595,000

3 beds1.5 baths1,840 sq ft

10 Crown St, Trumbull, CT 06611

Formal dining room • Brick fireplace • Vaulted ceiling

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
New price and an opportunity you do not want to miss in Fairfield's desirable Stratfield neighborhood! This charming Cape offers incredible value, wonderful curb appeal, and a location that puts you close to everything Fairfield has to offer. Step inside to a bright eat in kitchen with granite countertops, stainless steel appliances, and ample cabinet space. The inviting living room features gleaming hardwood floors, a cozy fireplace, and crown moldings. The main level offers a spacious primary bedroom, a full bath with tub and shower accented by white Carrara marble floors, plus a second bedroom ideal for guests, a home office, or den. The upper level includes two generously sized bedrooms

$525,000

4 beds1.5 baths1,082 sq ft

2082 Stratfield Rd, Fairfield, CT 06825

Eat in kitchen • Cozy fireplace • Granite countertops

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to this beautifully maintained classic 1938 Ranch located in the heart of the Center District. This home offers single level living space with hardwood floors throughout. The inviting living room is highlighted with a beautiful stone fireplace, custom built-ins and a soaring ceiling. The kitchen boasts granite countertops, tile flooring, gas for cooking, plenty of cabinetry and a bright skylight that fills the space with natural light. A mud room is conveniently located off the kitchen. Both bedrooms are on the main level, including a huge primary bedroom, with an oversized double closet and a private en suite bath. The second bedroom has custom built-ins with plenty of storage alon

$530,000

2 beds2 baths1,168 sq ft

464 Church Hill Rd, Trumbull, CT 06611

Bright skylight • Custom built-ins • Stone fireplace

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Originally built in 1726 and extensively remodeled, reimagined and re-engineered in 2007, 149 Dudley Road is a rare country estate where nearly three centuries of history meet sophisticated modern living. Set behind gates on more than five magnificent level acres, this exceptional property combines timeless New England character, beautifully considered interiors and extraordinary amenities in an idyllic, park-like setting. The main residence is warm, elegant and filled with natural light, with wide-board floors, handsome millwork, dramatic stone fireplaces, original architectural details and inviting covered and wraparound porches that honor the home's remarkable heritage. Generously scaled

$2,995,000

5 beds5.5 baths5,940 sq ft

149 Dudley Rd, Wilton, CT 06897

Park-like setting • Stunning kitchen • Exceptional property

Property at 366 Brookside Dr, Fairfield, CT 06824, 3 beds, 2 baths

$775,000

3 beds2 baths2,135 sq ft

366 Brookside Dr, Fairfield, CT 06824

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 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 1 Albers Rd, Danbury, CT 06811, 2 beds, 1 bath

$430,000

2 beds1 bath2,024 sq ft

1 Albers Rd, Danbury, CT 06811

Property at 68 Parry Rd, Stamford, CT 06907, 3 beds, 2.5 baths

$1,425,000

3 beds2.5 baths2,790 sq ft

68 Parry Rd, Stamford, CT 06907

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 326 Soundview Ave, Bridgeport, CT 06606, 4 beds, 2 baths

$459,000

4 beds2 baths1,715 sq ft

326 Soundview Ave, Bridgeport, CT 06606

Property at 98 Ball Pond Rd, Danbury, CT 06811, 6 beds, 6 baths

$850,000

6 beds6 baths3,628 sq ft

98 Ball Pond Rd, Danbury, CT 06811

Property at 744 Canaan Rd Unit Blg87 21, Bridgeport, CT 06610, 1 bed, 1 bath

$30,000

1 bed1 bath401 sq ft

744 Canaan Rd Unit Blg87 21, Bridgeport, CT 06610

Property at 73 Carlson Ave, Bridgeport, CT 06606, 3 beds, 1 bath

$395,000

3 beds1 bath1,472 sq ft

73 Carlson Ave, Bridgeport, CT 06606

Property at 51 Maher Dr, Norwalk, CT 06850, 3 beds, 2 baths

$699,900

3 beds2 baths1,076 sq ft

51 Maher Dr, Norwalk, CT 06850

Property at 21 Soundview Ave, Norwalk, CT 06854, 5 beds, 2.5 baths

$785,000

5 beds2.5 baths1,826 sq ft

21 Soundview Ave, Norwalk, CT 06854

Property at 17 Huckleberry Dr S, Norwalk, CT 06850, 4 beds, 2.5 baths

$1,150,000

4 beds2.5 baths2,628 sq ft

17 Huckleberry Dr S, Norwalk, CT 06850

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

$475,000

3 beds1.5 baths1,670 sq ft

120 Howe Ave, Shelton, CT 06484

Property at 326 North St, Ridgefield, CT 06877, 3 beds, 1.5 baths

$1,150,000

3 beds1.5 baths1,496 sq ft

326 North St, Ridgefield, CT 06877

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 240 Milford Ave, Stratford, CT 06615, 3 beds, 1 bath

$425,000

3 beds1 bath1,155 sq ft

240 Milford Ave, Stratford, CT 06615

Property at 220 Melville Dr, Fairfield, CT 06825, 2 beds, 1 bath

$390,000

2 beds1 bath806 sq ft

220 Melville Dr, Fairfield, CT 06825

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

$1,695,000

3 beds2.5 baths2,074 sq ft

845 Kings Hwy W, Fairfield, CT 06825

Property at 438 High St, Fairfield, CT 06824, 4 beds, 2 baths

$629,000

4 beds2 baths1,142 sq ft

438 High St, Fairfield, CT 06824

Property at 1250 Hillside Ave, Stratford, CT 06614, 4 beds, 2 baths

$519,900

4 beds2 baths1,923 sq ft

1250 Hillside Ave, Stratford, CT 06614

Property at 136 Chatham Rd, Fairfield, CT 06825, 3 beds, 2.5 baths

$1,049,000

3 beds2.5 baths2,352 sq ft

136 Chatham Rd, Fairfield, CT 06825

Property at 480 Ezra St, Bridgeport, CT 06606, 3 beds, 2 baths

$420,000

3 beds2 baths1,296 sq ft

480 Ezra St, Bridgeport, CT 06606

Property at 31 Splitrock Rd, Norwalk, CT 06854, 4 beds, 4 baths

$1,900,000

4 beds4 baths3,392 sq ft

31 Splitrock Rd, Norwalk, CT 06854

Property at 12 Edgewood Ave, Trumbull, CT 06611, 3 beds, 2.5 baths

$679,900

3 beds2.5 baths1,734 sq ft

12 Edgewood Ave, Trumbull, CT 06611

Property at 501 Lake Ave, Bridgeport, CT 06605, 2 beds, 1 bath

$699,000

2 beds1 bath1,344 sq ft

501 Lake Ave, Bridgeport, CT 06605

Property at 321 Oenoke Rdg, New Canaan, CT 06840, 3 beds, 3.5 baths

$3,300,000

3 beds3.5 baths5,520 sq ft

321 Oenoke Rdg, New Canaan, CT 06840

Property at 8 Rising Rd, Norwalk, CT 06850, 6 beds, 4 baths

$1,349,000

6 beds4 baths3,860 sq ft

8 Rising Rd, Norwalk, CT 06850

Property at 845 Stratford Rd, Stratford, CT 06615, 3 beds, 2 baths

$595,000

3 beds2 baths1,757 sq ft

845 Stratford Rd, Stratford, CT 06615

Property at 720 Jewett Ave, Bridgeport, CT 06606, 3 beds, 1 bath

$439,000

3 beds1 bath1,152 sq ft

720 Jewett Ave, Bridgeport, CT 06606

Property at 6 Brinsmade Ln, Sherman, CT 06784, 5 beds, 4 baths

$1,099,000

5 beds4 baths4,200 sq ft

6 Brinsmade Ln, Sherman, CT 06784

Property at 43 Breyer Ave, Bridgeport, CT 06606, 2 beds, 1 bath

$419,000

2 beds1 bath984 sq ft

43 Breyer Ave, Bridgeport, CT 06606

Property at 226 Ludlow St, Stamford, CT 06902, 6 beds, 2 baths

$759,900

6 beds2 baths2,620 sq ft

226 Ludlow St, Stamford, CT 06902

Property at 660 W Jackson Ave, Bridgeport, CT 06604, 4 beds, 1.5 baths

$459,900

4 beds1.5 baths1,821 sq ft

660 W Jackson Ave, Bridgeport, CT 06604

Property at 215 Knickerbocker Ave, Stamford, CT 06907, 4 beds, 3.5 baths

$999,999

4 beds3.5 baths3,653 sq ft

215 Knickerbocker Ave, Stamford, CT 06907

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Based on information submitted to the MLS GRID as of Mon Oct 05 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 831 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, 740 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 883 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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