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:
Unit sold "As Is" Condition. Buyer to do their "Due Diligence" before submitting an offer. Agent has not been in the unit. The fieldcard does not reflect the individual unit - it is potentially the building. Information was supplied by President of Assoc, who conveyed it is a TH w/ 2 bedrooms on the 2nd flr. Attorney representing association was not familiar with unit. Subject to DSS & Probate Court Approval. Association must also approve buyer - application attached. Must be owner-occupied. It is believed that there might be a walk up attic and a basement, which might have a washer/dryer hook up. Sq. Ft. is unknown. The rooms, configuration & most of the inf

$40,000

2 beds1 bath99,999 sq ft

1034 Connecticut Ave, Bridgeport, CT 06607

$479 HOA • Built 1914 • Listed 44 days

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Fantastic in-town opportunity for builders and investors! On a tree lined street with the French bakery on the corner, this 2-family home is just 2 blocks to downtown Fairfield and the train and close to all 5 beaches! This 2-family home has been brought down to the studs inside and offers a blank canvas to bring your ideas to life. Currently setup as a 2-family, there are options to keep it a 2-family or build a new single family home. For safety reasons, interior of home cannot be accessed for showings. Interior videos available upon request. Home is in flood zone.

$699,000

3 beds2 baths1,890 sq ft

43 Helen St, Fairfield, CT 06824

3 electrical panels • Tree lined street • 2 gas meters

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Historic charm meets modern luxury on 5 private acres in lower Weston. Set at the end of a long, tree-lined drive, this distinctive country estate offers rare privacy, character, and fully updated amenities. Once the personal retreat of Godspell creator John-Michael Tebelak, the property features a beautifully reimagined Tudor Revival residence expanded and renovated by noted architect Jack Franzen. The main home blends classic craftsmanship with contemporary comfort, offering 7 bedrooms, 8 full and 2 half baths, and a series of refined living spaces. Highlights include a dramatic two-story media and family wing with an 8x10' retractable theater screen, an elegant library, home office, and

$3,795,000

7 beds9 baths11,075 sq ft

214 Good Hill Rd, Weston, CT 06883

Tree lined drive • 4.98 acre lot • 3 garage spots

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to your dream come true lifestyle in the heart of Fairfield's coveted beach/town community-where coastal charm meets everyday convenience. This brand-new modern Colonial is more than a home, it's an upgraded living experience. Imagine morning walks to South Pine Creek Beach, afternoons on the tennis courts or golf course & evenings dining at vibrant restaurants, live music & theatres downtown-all just a short stroll from your front door. With the train only minutes away, your commute becomes effortless, leaving more time to enjoy friends, family. .. and life! This 5-bedroom, 4.5 bath home blends timeless design with a modern edge. The open-concept layout features a brigh

$1,600,000

5 beds4.5 baths3,159 sq ft

226 Ruane St, Fairfield, CT 06824

9,583 sq ft lot • Garage • Built 1917

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
This enchanting stone home is on the market for the first time in 40 years. It is in the heart of downtown New Canaan presenting a rare opportunity to embrace a property rich in character. Nestled on nearly half an acre of meticulously landscaped grounds, this charming colonial offers a private and tranquil atmosphere just a short stroll from the vibrant town center. Over the years, certain areas of the home have been beautifully updated and maintained, while other areas may benefit from renovation. The home being sold "as is" spans 3,557 square feet across three levels, the generous first floor layout features a comfortably sized living and dining room filled with charm, leading

$1,800,000

4 beds3 baths2,747 sq ft

180 Summer St, New Canaan, CT 06840

Stone home • Open-concept kitchen • Large loft above

Property at 1170 South Ave, Stratford, CT 06615, 3 beds, 2.5 baths

$529,900

3 beds2.5 baths1,841 sq ft

1170 South Ave, Stratford, CT 06615

Property at 1148 Hope St, Stamford, CT 06907, 3 beds, 2 baths

$849,900

3 beds2 baths2,397 sq ft

1148 Hope St, Stamford, CT 06907

Property at 53 Hilltop Dr, Southport, CT 06890, 3 beds, 2 baths

$699,999

3 beds2 baths1,382 sq ft

53 Hilltop Dr, Southport, CT 06890

Property at 50 Goddard Ave, Bridgeport, CT 06610, 4 beds, 1 bath

$350,000

4 beds1 bath1,482 sq ft

50 Goddard Ave, Bridgeport, CT 06610

Property at 516 Valley Rd, Stratford, CT 06615, 2 beds, 2 baths

$549,900

2 beds2 baths1,759 sq ft

516 Valley Rd, Stratford, CT 06615

Property at 15 Flak Ln, New Fairfield, CT 06812, 3 beds, 3 baths

$680,000

3 beds3 baths2,292 sq ft

15 Flak Ln, New Fairfield, CT 06812

Property at 161 Jockey Hollow Rd, Monroe, CT 06468, 3 beds, 1.5 baths

$465,000

3 beds1.5 baths1,986 sq ft

161 Jockey Hollow Rd, Monroe, CT 06468

Property at 22 Glenbrook Rd #414, Stamford, CT 06902, 1 bed, 1 bath

$199,000

1 bed1 bath535 sq ft

22 Glenbrook Rd #414, Stamford, CT 06902

Property at 32 Redwood Dr, Bethel, CT 06801, 5 beds, 4.5 baths

$749,000

5 beds4.5 baths2,878 sq ft

32 Redwood Dr, Bethel, CT 06801

Property at 54 Vernon St, Stratford, CT 06615, 3 beds, 2 baths

$469,000

3 beds2 baths1,616 sq ft

54 Vernon St, Stratford, CT 06615

Property at 22 Fair St, Norwalk, CT 06851, 3 beds, 3 baths

$629,999

3 beds3 baths2,104 sq ft

22 Fair St, Norwalk, CT 06851

Property at 130 Ash St, Stratford, CT 06615, 3 beds, 1 bath

$500,000

3 beds1 bath1,697 sq ft

130 Ash St, Stratford, CT 06615

Property at 31 Whittier St, Bridgeport, CT 06605, 16 beds, 8 baths

$1,900,000

16 beds8 baths5,824 sq ft

31 Whittier St, Bridgeport, CT 06605

Property at 643 Newfield Ave, Bridgeport, CT 06607, 6 beds, 3 baths

$460,000

6 beds3 baths2,644 sq ft

643 Newfield Ave, Bridgeport, CT 06607

Property at 2 Coldspring St, Norwalk, CT 06850, 3 beds, 3 baths

$599,000

3 beds3 baths1,464 sq ft

2 Coldspring St, Norwalk, CT 06850

Property at 182 Trumbull Ave, Bridgeport, CT 06606, 3 beds, 1 bath

$349,000

3 beds1 bath1,001 sq ft

182 Trumbull Ave, Bridgeport, CT 06606

Property at 40 Maple Ave N, Westport, CT 06880, 3 beds, 2 baths

$1,699,900

3 beds2 baths3,171 sq ft

40 Maple Ave N, Westport, CT 06880

Property at 40 Arnold Ln, Norwalk, CT 06853, 4 beds, 4.5 baths

$1,895,000

4 beds4.5 baths3,319 sq ft

40 Arnold Ln, Norwalk, CT 06853

Property at 11 Sterling Dr, Westport, CT 06880, 4 beds, 4 baths

$4,435,000

4 beds4 baths4,446 sq ft

11 Sterling Dr, Westport, CT 06880

Property at 62 Old Hawleyville Rd, Bethel, CT 06801, 3 beds, 2.5 baths

$699,000

3 beds2.5 baths3,492 sq ft

62 Old Hawleyville Rd, Bethel, CT 06801

Property at 3 Finney Knoll Ln, Riverside, CT 06878, 4 beds, 3.5 baths

$3,299,000

4 beds3.5 baths4,600 sq ft

3 Finney Knoll Ln, Riverside, CT 06878

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 695 697 LAUREL Ave, Bridgeport, CT 06604, 6 beds, 3 baths

$537,600

6 beds3 baths3,826 sq ft

695 697 LAUREL Ave, Bridgeport, CT 06604

Property at Undisclosed address, Bridgeport, CT 06607, 2 beds, 1 bath

$64,000

2 beds1 bath700 sq ft

Undisclosed address, Bridgeport, CT 06607

Property at 185 Haviland Rd, Stamford, CT 06903, 3 beds, 3 baths

$1,280,000

3 beds3 baths4,155 sq ft

185 Haviland Rd, Stamford, CT 06903

Property at 4 Colony Rd, Weston, CT 06883, 2 beds, 2 baths

$829,000

2 beds2 baths1,689 sq ft

4 Colony Rd, Weston, CT 06883

Property at 500 Dewey St, Bridgeport, CT 06605, 3 beds, 1 bath

$250,000

3 beds1 bath1,460 sq ft

500 Dewey St, Bridgeport, CT 06605

Property at 2281 Redding Rd, Fairfield, CT 06824, 5 beds, 4.5 baths

$4,995,000

5 beds4.5 baths4,191 sq ft

2281 Redding Rd, Fairfield, CT 06824

Property at 114 Ferris Hill Rd, New Canaan, CT 06840, 6 beds, 7.5 baths

$4,995,000

6 beds7.5 baths7,700 sq ft

114 Ferris Hill Rd, New Canaan, CT 06840

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 375 Ruth St, Bridgeport, CT 06606, 3 beds, 1 bath

$400,000

3 beds1 bath1,116 sq ft

375 Ruth St, Bridgeport, CT 06606

Property at 75 Coolidge Ave, Stamford, CT 06906, 8 beds, 8.5 baths

$1,495,000

8 beds8.5 baths5,530 sq ft

75 Coolidge Ave, Stamford, CT 06906

Property at 39 Jane St, Bridgeport, CT 06608, 6 beds, 2 baths

$479,000

6 beds2 baths2,156 sq ft

39 Jane St, Bridgeport, CT 06608

Property at 196 Avon St, Stratford, CT 06615, 5 beds, 3 baths

$499,900

5 beds3 baths2,178 sq ft

196 Avon St, Stratford, CT 06615

Property at 32 Old Green Rd, Sandy Hook, CT 06482, 3 beds, 1 bath

$499,500

3 beds1 bath1,724 sq ft

32 Old Green Rd, Sandy Hook, CT 06482

Property at 106 Patterson Ave, Greenwich, CT 06830, 5 beds, 4 baths

$4,500,000

5 beds4 baths3,448 sq ft

106 Patterson Ave, Greenwich, CT 06830

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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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