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:
Charming & Meticulously Cared-For Cape in North End | 720 Jewett Ave. Charming North End Cape with Park-Like Yard & Hot Tub. Welcome to 720 Jewett Avenue, a beautifully maintained 3-bedroom Cape Cod home located in Bridgeport's desirable North End. Combining classic architectural detail with key energy-efficient upgrades, this home offers warmth, comfort, and an exceptional layout for everyday living and outdoor entertaining. Property Highlights: Inviting Main Level features a formal dining room, cozy living room with detailed crown molding and raised-panel woodwork throughout. Updated Kitchen: Equipped with newer cabinetry and designed for easy flow into the dining room for sea

$439,000

3 beds1 bath1,152 sq ft

720 Jewett Ave, Bridgeport, CT 06606

Hot tub • Covered patio • Park-like yard

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Discover a unique combination of space, privacy and versatility in this 4-bedroom, 2-full-bath Colonial offering approximately 2,782 square feet of living space on just over an acre. Recent improvements include a newly renovated second-floor bathroom and a new deck, adding to the appeal of this spacious Stratford home. Hardwood floors complement the main level, where a generous living room with fireplace and bay window creates a warm gathering space. A versatile den provides additional room to relax and offers direct access to the new deck, perfect for extending your living space outdoors. The light-filled dining area features vaulted ceilings and access to the outdoors. Three bedrooms and

$649,000

4 beds2 baths2,782 sq ft

1149 Warner Hill Rd, Stratford, CT 06614

Versatile den • New deck • Central air

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 215 Knickerbocker Avenue, an expansive 4-bedroom, 3.5-bath Colonial offering exceptional space, flexibility, and comfort in Stamford's desirable Springdale neighborhood. The main level is ideal for both everyday living and entertaining, featuring a kitchen with quartz countertops, a large center island, pantry, and stainless-steel appliances, opening to an expansive family room. Formal living and dining rooms with hardwood floors provide additional gathering space, while a main-level bedroom and full bath offer excellent flexibility for guests, a home office, or multigenerational living. Upstairs, the impressive primary suite creates a true private retreat with cathedral ceilings

$999,999

4 beds3.5 baths3,653 sq ft

215 Knickerbocker Ave, Stamford, CT 06907

Large center island • Main level bedroom • 7,405 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 33 Monroe St, a completely remodeled Colonial in Shelton offering 3 bedrooms, 1 full bath, and 1 half bath. This home features approximately 1,727 square feet of living space, hardwood floors, a spacious kitchen, dining room, and living room. The property also offers a full basement with walk-out access, walk-up attic, enclosed porch, porch, and deck. Conveniently located in Shelton with access to public utilities and natural gas heat. A great opportunity to make this home your own. The property offers a traditional Colonial layout with three bedrooms and flexible living spaces. Additional features include central air, natural gas heating, public water and public sewer, hardwood

$449,777

3 beds1.5 baths1,727 sq ft

33 Monroe St, Shelton, CT 06484

Walk-out access • Full basement • Enclosed porch

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Prestigious location. Stately presence. Exceptional living. Presenting a Premier 1.25-acre Sasco Hill estate w/ unrivaled luxury across 4 levels of living. This magnificent home features 5 bedrooms, 9 baths & an uncompromised commitment to fine detail. Outside, a private resort awaits featuring a heated pool & spa, a fully equipped outdoor kitchen & an expansive terrace overlooking gorgeous gardens. For those seeking future expansion, this estate offers an accessory apartment over the garage w/ roughed-in plumbing & electricity in place. Iron gates flanked by stone lions welcome you to a grand 2 story foyer. The main level presents rare, fine details starting w/ the

$7,500,000

5 beds7.5 baths11,999 sq ft

541 Sasco Hill Rd, Fairfield, CT 06824

1.25-acre estate • Grand foyer • Heated pool

Property at 65 Glenwood Ave, Stratford, CT 06614, 3 beds, 1 bath

$470,000

3 beds1 bath1,528 sq ft

65 Glenwood Ave, Stratford, CT 06614

Property at 474 Brookside Rd, New Canaan, CT 06840, 6 beds, 4.5 baths

$5,895,000

6 beds4.5 baths7,723 sq ft

474 Brookside Rd, New Canaan, CT 06840

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 2029 Kings Hwy, Fairfield, CT 06824, 6 beds, 3 baths

$1,200,000

6 beds3 baths2,487 sq ft

2029 Kings Hwy, Fairfield, CT 06824

Property at 40 Kellogg St, Brookfield, CT 06804, 5 beds, 2 baths

$885,000

5 beds2 baths2,130 sq ft

40 Kellogg St, Brookfield, CT 06804

Property at 139 Lee Ave, Bridgeport, CT 06605, 6 beds, 3 baths

$634,500

6 beds3 baths4,000 sq ft

139 Lee Ave, Bridgeport, CT 06605

Property at 213 Knapps Hwy, Fairfield, CT 06825, 4 beds, 2 baths

$569,000

4 beds2 baths1,075 sq ft

213 Knapps Hwy, Fairfield, CT 06825

Property at 16 Mount Nebo Rd, Newtown, CT 06470, 6 beds, 7 baths

$895,000

6 beds7 baths4,228 sq ft

16 Mount Nebo Rd, Newtown, CT 06470

Property at 25-35-37 Mills Ln, Easton, CT 06612, 3 beds, 2 baths

$1,248,000

3 beds2 baths2,284 sq ft

25-35-37 Mills Ln, Easton, CT 06612

Property at 195 Webb Cir, Monroe, CT 06468, 4 beds, 2.5 baths

$949,000

4 beds2.5 baths3,074 sq ft

195 Webb Cir, Monroe, CT 06468

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 220 Priscilla St, Bridgeport, CT 06610, 5 beds, 2.5 baths

$479,000

5 beds2.5 baths2,052 sq ft

220 Priscilla St, Bridgeport, CT 06610

Property at 216 Cross Hill Rd, Monroe, CT 06468, 2 beds, 1 bath

$336,000

2 beds1 bath932 sq ft

216 Cross Hill Rd, Monroe, CT 06468

Property at 145 Canal St #12, Shelton, CT 06484, 1 bed, 1 bath

$229,999

1 bed1 bath900 sq ft

145 Canal St #12, Shelton, CT 06484

Property at 704 W Taft Ave, Bridgeport, CT 06604, 3 beds, 1.5 baths

$474,900

3 beds1.5 baths1,578 sq ft

704 W Taft Ave, Bridgeport, CT 06604

Property at 86 Vanguard St, Bridgeport, CT 06606, 2 beds, 1.5 baths

$479,000

2 beds1.5 baths1,852 sq ft

86 Vanguard St, Bridgeport, CT 06606

Property at 52 Lafayette Pl Unit 2I, Greenwich, CT 06830, 1 bed, 1 bath

$449,999

1 bed1 bath570 sq ft

52 Lafayette Pl Unit 2I, Greenwich, CT 06830

Property at 260 Success Ave Unit 11 Bldg 91, Bridgeport, CT 06610, 2 beds, 1 bath

$65,000

2 beds1 bath625 sq ft

260 Success Ave Unit 11 Bldg 91, Bridgeport, CT 06610

Property at 70 Stonehouse Rd, Trumbull, CT 06611, 3 beds, 2 baths

$700,000

3 beds2 baths1,701 sq ft

70 Stonehouse Rd, Trumbull, CT 06611

Property at 13 Fairchild Dr, Bethel, CT 06801, 4 beds, 1 bath

$550,000

4 beds1 bath1,176 sq ft

13 Fairchild Dr, Bethel, CT 06801

Property at 180 Dupont Pl, Bridgeport, CT 06610, 4 beds, 2 baths

$599,900

4 beds2 baths1,620 sq ft

180 Dupont Pl, Bridgeport, CT 06610

Property at 57-59 Fairview Ave, Bridgeport, CT 06606, 6 beds, 2 baths

$689,900

6 beds2 baths2,962 sq ft

57-59 Fairview Ave, Bridgeport, CT 06606

Property at 51 Brown Ave, Stamford, CT 06902, 9 beds, 4 baths

$1,500,000

9 beds4 baths3,342 sq ft

51 Brown Ave, Stamford, CT 06902

Property at 114 Woodward Ave, Norwalk, CT 06854, 4 beds, 4 baths

$685,000

4 beds4 baths2,126 sq ft

114 Woodward Ave, Norwalk, CT 06854

Property at 37 Allview Ave, Norwalk, CT 06854, 2 beds, 2 baths

$599,000

2 beds2 baths1,572 sq ft

37 Allview Ave, Norwalk, CT 06854

Property at 31 Meadow Wood Dr, Greenwich, CT 06830, 3 beds, 3.5 baths

$6,995,000

3 beds3.5 baths2,425 sq ft

31 Meadow Wood Dr, Greenwich, CT 06830

Property at 1031 Lindley St, Bridgeport, CT 06606, 4 beds, 2 baths

$599,900

4 beds2 baths2,376 sq ft

1031 Lindley St, Bridgeport, CT 06606

Property at 24 Elm St, Shelton, CT 06484, 6 beds, 2 baths

$539,000

6 beds2 baths1,748 sq ft

24 Elm St, Shelton, CT 06484

Property at 71 Alvord Ln, Stamford, CT 06902, 3 beds, 2 baths

$799,000

3 beds2 baths1,980 sq ft

71 Alvord Ln, Stamford, CT 06902

Property at 866 Merritt St, Bridgeport, CT 06606, 3 beds, 1.5 baths

$475,000

3 beds1.5 baths1,967 sq ft

866 Merritt St, Bridgeport, CT 06606

Property at 161-163 Harriet St, Bridgeport, CT 06608, 6 beds, 3 baths

$549,000

6 beds3 baths2,957 sq ft

161-163 Harriet St, Bridgeport, CT 06608

Property at 18 Patch St, Danbury, CT 06810, 6 beds, 2 baths

$615,000

6 beds2 baths1,102 sq ft

18 Patch St, Danbury, CT 06810

Property at 3 Beacon Sq, Fairfield, CT 06825, 3 beds, 1 bath

$624,999

3 beds1 bath1,257 sq ft

3 Beacon Sq, Fairfield, CT 06825

Property at 810 North Ave, Bridgeport, CT 06606, 8 beds, 3 baths

$689,000

8 beds3 baths3,348 sq ft

810 North Ave, Bridgeport, CT 06606

Property at 1074 Sturges Hwy, Fairfield, CT 06824, 5 beds, 4 baths

$2,690,000

5 beds4 baths4,540 sq ft

1074 Sturges Hwy, Fairfield, CT 06824

Property at 63 Mencel Cir Unit C, Bridgeport, CT 06610, 2 beds, 1 bath

$219,000

2 beds1 bath900 sq ft

63 Mencel Cir Unit C, Bridgeport, CT 06610

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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 847 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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