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:
A house-it's a place where life feels easy and full of warmth. Sunlight pours through wide windows and across hardwood floors, filling each room with a natural glow. Every room also elegantly flows from one to another which is ideal for loved ones congregating and also having your own personal space. The kitchen is the heart of the home with granite counters, stainless appliances, and a cozy breakfast nook where mornings begin with bringing the family close over coffee and conversation. The family room, anchored with a wood burning stove, is made for quiet evenings, perfect for the long winter months ahead. The sliders open to a spacious deck and backyard designed for summer gatherings and

$629,999

3 beds3 baths2,104 sq ft

22 Fair St, Norwalk, CT 06851

Breakfast nook • Stainless appliances • Wide windows

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
THE BEDFORD HOUSE - Architecturally and historically significant estate in coveted Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's most superb homes. Set on 2.33 acres with a gunite pool/spa, court and a 2400 sq ft barn featuring a 3-car garage, loft & more, the estate blends timeless elegance with modern comfort. Originally built in 1904 and designed by noted architects Visscher and Burley, this Colonial Revival home has undergone thoughtful renovations over the years to preserve and enhance its character. The main residence features 5 Bedrooms and 6.5 Baths with a well-planned layout for today's lifestyle. High ceilings, oversized windows,

$3,500,000

5 beds6.5 baths5,789 sq ft

221 Greens Farms Rd, Westport, CT 06880

2.33 acre lot • 3 garage spots • Pool

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
If you're looking for a well-kept home with character and spacious rooms in an established neighborhood, this charming home might be just what you've been waiting for. This cape-style home offers 4 comfortable bedrooms and 1 full bathroom. 2 of the bedrooms, as well as the full bath, are conveniently located on the first floor, allowing for 1-level living options. Step inside and you'll find a warm and inviting living space full of architectural charm. The layout is simple and functional, perfect for both relaxing and entertaining. The unfinished basement adds extra flexibility-whether you need a playroom, home office, workout space, or just some extra storage, you've got options. Let's not

$400,000

4 beds1 bath1,590 sq ft

216 Clover St, Stratford, CT 06614

5,227 sq ft lot • 3 parking spots • Built 1948

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
One-of-a-kind property, dwellings built by owners' grandfather. Summer porch included with upper larger unit. Small apartment has large open porch as well. Sixty- one has patio and nice rear property. Fifty-seven has front and rear property. See Addendum for additional dwelling. Unique income property - one of only four multiple rental dwellings in New Canaan with several buildings on one property. * * Property may not be subdivided. * * Driveway/accessway is property of State of Connecticut. New Canaan Public Works Department is responsible for snowplowing, blacktopping, and maintenance of accessway - very dependable, courteous service. Number sixty-one (larger dwelling) has studio apar

$1,300,000

4 beds3.5 baths2,064 sq ft

61 Smith Ridge Rd, New Canaan, CT 06840

Red barn • Open porch • Studio apartment

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Nicely updated and bright 3BR, 2 bath top floor apartment with great space, large windows, exceptional views, pretty finishes and fixtures with great attention to detail. There is a large open living room with built-ins, a breakfast & dining area, a lovely cherry and granite kitchen with top appliances, including a gas cooktop. Adjacent to the dining area are large sliders that open to an oversized private balcony overlooking treetops, an ideal spot for entertaining. The primary bedroom features a large oversized walk-in, and a lux bath with marble & granite stall shower and vanity. The two secondary bedrooms (one outfitted as an office) share a pretty hall bath. Added features

$995,000

3 beds3 baths1,508 sq ft

4 Putnam Hill Ln, Greenwich, CT 06830

Top floor apartment • Lux bath • Full-size laundry

Property at 508 Round Hill Rd, Greenwich, CT 06831, 6 beds, 4.5 baths

$6,395,000

6 beds4.5 baths4,629 sq ft

508 Round Hill Rd, Greenwich, CT 06831

Property at 44 Benedict Hill Rd, New Canaan, CT 06840, 5 beds, 3.5 baths

$2,750,000

5 beds3.5 baths3,200 sq ft

44 Benedict Hill Rd, New Canaan, CT 06840

Property at 108 Gregory Blvd, Norwalk, CT 06855, 4 beds, 3.5 baths

$2,299,000

4 beds3.5 baths3,030 sq ft

108 Gregory Blvd, Norwalk, CT 06855

Property at 14 Northfield Dr, Westport, CT 06880, 3 beds, 2 baths

$1,169,000

3 beds2 baths1,813 sq ft

14 Northfield Dr, Westport, CT 06880

Property at 546 Lake Ave, Greenwich, CT 06830, 6 beds, 6.5 baths

$9,870,000

6 beds6.5 baths7,456 sq ft

546 Lake Ave, Greenwich, CT 06830

Property at 21 oven Rock Rd, Bethel, CT 06801, 4 beds, 2 baths

$435,000

4 beds2 baths1,756 sq ft

21 oven Rock Rd, Bethel, CT 06801

Property at 58 Old Rock Ln, Norwalk, CT 06850, 3 beds, 3 baths

$975,000

3 beds3 baths1,762 sq ft

58 Old Rock Ln, Norwalk, CT 06850

Property at 101 Parade Hill Rd, New Canaan, CT 06840, 3 beds, 2 baths

$1,179,900

3 beds2 baths1,304 sq ft

101 Parade Hill Rd, New Canaan, CT 06840

Property at 270 East Ave, Bridgeport, CT 06610, 4 beds, 1.5 baths

$275,000

4 beds1.5 baths1,645 sq ft

270 East Ave, Bridgeport, CT 06610

Property at 51 Princeton St, Bridgeport, CT 06605, 4 beds, 2 baths

$529,900

4 beds2 baths1,994 sq ft

51 Princeton St, Bridgeport, CT 06605

Property at 45 Hecker Ave, Darien, CT 06820, 5 beds, 2 baths

$999,999

5 beds2 baths2,844 sq ft

45 Hecker Ave, Darien, CT 06820

Property at 785 Connecticut Ave #2, Bridgeport, CT 06607, 1 bed, 1 bath

$55,000

1 bed1 bath625 sq ft

785 Connecticut Ave #2, Bridgeport, CT 06607

Property at 20 Georgetown Rd, Weston, CT 06883, 3 beds, 2 baths

$524,000

3 beds2 baths1,616 sq ft

20 Georgetown Rd, Weston, CT 06883

Property at 45 Lake Dr S, New Fairfield, CT 06812, 4 beds, 3.5 baths

$1,745,000

4 beds3.5 baths3,020 sq ft

45 Lake Dr S, New Fairfield, CT 06812

Property at 5 Outer Rd, Norwalk, CT 06854

$1,350,000

— beds— baths— sq ft

5 Outer Rd, Norwalk, CT 06854

Property at 549 Round Hill Rd, Greenwich, CT 06831

$6,950,000

— beds— baths— sq ft

549 Round Hill Rd, Greenwich, CT 06831

Property at 320 Union Ave, Bridgeport, CT 06607

$175,000

— beds— baths1,405 sq ft

320 Union Ave, Bridgeport, CT 06607

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Based on information submitted to the MLS GRID as of Sun Nov 30 2025. 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 508 vintage homes for sale in Fairfield County at a median listing price of $680K. 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 48 days and receive 4 offers. This map is refreshed with the newest listings in Fairfield County every 15 minutes.

In the past month, 896 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 778 condos, 1 townhouse, and 200 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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