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:
Exceptional opportunity in one of Cos Cob's most desirable neighborhoods! This charming two-family offers incredible versatility for investors, builders, and end users. Renovate the existing multifamily or explore conversion into a beautiful single-family residence. With current rents below market, there is immediate income and significant potential to optimize rental revenue. Buyers considering conversion can collect rent to offset carrying costs while pursuing plans and approvals. Features include hardwood floors, spacious living areas, a large rear deck, private backyard, attached garage, and driveway parking. A rare opportunity to unlock value in a sought-after Cos Cob location!

$1,495,000

4 beds3 baths2,243 sq ft

4 Tremont St, Greenwich, CT 06807

Multifamily • Private backyard • Two-family

Mike Parelli Real Estate LLC

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome home to this charming Cape Cod-style home offering 3 bedrooms and 1.5 bathrooms with a comfortable and functional layout. Enjoy the efficiency of natural gas heat along with central air conditioning for year-round comfort. The home features inviting living spaces, generously sized bedrooms, and plenty of potential to make it your own. With its classic Cape Cod character and practical amenities, this home is a wonderful opportunity for anyone looking for comfort, convenience, and a place to call home.

$369,000

3 beds1.5 baths1,491 sq ft

326 Burritt Ave, Stratford, CT 06615

5,227 sq ft lot • Garage • Built 1939

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Tucked among some of Black Rock's most beautiful homes-and just steps from the Black Rock Yacht Club and St. Mary's by the Sea-37 Thorne Place is a grand and utterly unique residence set on a spectacular double lot. With its distinctive Tudor-inspired architecture, sweeping grounds, multiple porches, soaring ceilings, gorgeous gardens & exceptional scale, this is a home with presence- and personality. Inside, original character meets a wonderfully playful aesthetic, with rich color, pattern, beautiful millwork, arched doorways, handsome fireplaces & walls of windows at every turn. A spectacular green sunroom wrapped in windows overlooks the gardens, while gracious living &

$2,499,000

5 beds5 baths4,329 sq ft

37 Thorne Pl, Bridgeport, CT 06605

0.42 acre lot • 2 garage spots • Built 1918

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
COMING SOON! INVESTOR & FIXER UPPER OPPORTUNITY IN STRATFORD, CT! Calling all investors, contractors, and buyers with a vision! Located in the desirable South End of Stratford Connecticut, close to New York line, this property offers an exciting opportunity to bring a home back to life and make it your own. Featuring 3/4 bedrooms and 2 full bathrooms, this property offers a layout with unique room access that provides an opportunity to reimagine the space during renovation. The first floor full bathroom includes existing plumbing for a washer and dryer. The second full bathroom is accessed through none of the bedrooms. The entire home needs renovation, making this a great opportunity

$350,000

4 beds2 baths1,666 sq ft

1547 Stratford Ave, Stratford, CT 06615

Unique room access • Nice sized backyard • Long driveway

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Space, warmth and an opportunity to make it your own await at 101 Hoyt Street. Set on approximately 0.4 acres, this home offers a spacious layout and three fireplaces that add character throughout. A generous kitchen connects to the family room, creating a welcoming gathering place for everyday living and entertaining. The spacious primary suite features a private full bath and its own fireplace-a cozy retreat at the end of the day. This home offers flexibility for guests, a home office or creative pursuits, while an attached two-car garage adds everyday convenience. The home also features a new roof. Located within walking distance of Holmes Elementary School, this home combines space and

$1,850,000

4 beds3 baths3,414 sq ft

101 Hoyt St, Darien, CT 06820

Generous kitchen • Three fireplaces • Private full bath

Property at 4 Mallard Rd, Norwalk, CT 06850, 2 beds, 1 bath

$699,999

2 beds1 bath1,189 sq ft

4 Mallard Rd, Norwalk, CT 06850

Property at 148 Cross Hill Rd, Monroe, CT 06468, 3 beds, 2 baths

$599,000

3 beds2 baths2,130 sq ft

148 Cross Hill Rd, Monroe, CT 06468

Property at 59 Creeping Hemlock Dr, Norwalk, CT 06851, 4 beds, 3 baths

$899,900

4 beds3 baths2,346 sq ft

59 Creeping Hemlock Dr, Norwalk, CT 06851

Property at 60 Broadbridge Rd, Bridgeport, CT 06610, 4 beds, 2.5 baths

$629,900

4 beds2.5 baths3,282 sq ft

60 Broadbridge Rd, Bridgeport, CT 06610

Property at 66 Lincoln Ave, Stamford, CT 06902, 10 beds, 3 baths

$1,030,000

10 beds3 baths3,136 sq ft

66 Lincoln Ave, Stamford, CT 06902

Property at 22 Hemlock Trl, Sandy Hook, CT 06482, 2 beds, 1 bath

$413,500

2 beds1 bath1,222 sq ft

22 Hemlock Trl, Sandy Hook, CT 06482

Property at 1535 Park Ave, Bridgeport, CT 06604, 9 beds, 3 baths

$725,000

9 beds3 baths5,190 sq ft

1535 Park Ave, Bridgeport, CT 06604

Property at 76 Peaceable St, Redding, CT 06896, 3 beds, 3.5 baths

$1,400,000

3 beds3.5 baths2,400 sq ft

76 Peaceable St, Redding, CT 06896

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 85 Newman Pl, Fairfield, CT 06825, 4 beds, 2.5 baths

$989,000

4 beds2.5 baths2,338 sq ft

85 Newman Pl, Fairfield, CT 06825

Property at 96 Fitch Ave, Darien, CT 06820, 4 beds, 4 baths

$2,350,000

4 beds4 baths3,025 sq ft

96 Fitch Ave, Darien, CT 06820

Property at 59 Gillotti Rd, New Fairfield, CT 06812, 1 bed, 1 bath

$349,000

1 bed1 bath736 sq ft

59 Gillotti Rd, New Fairfield, CT 06812

Property at 37 Arch St, Greenwich, CT 06830, 9 beds, 1.5 baths

$3,475,000

9 beds1.5 baths3,090 sq ft

37 Arch St, Greenwich, CT 06830

Property at 155 Moody Ave, Fairfield, CT 06825, 3 beds, 1.5 baths

$714,900

3 beds1.5 baths1,510 sq ft

155 Moody Ave, Fairfield, CT 06825

Property at 51 Maher Dr, Norwalk, CT 06850, 3 beds, 1.5 baths

$699,900

3 beds1.5 baths1,076 sq ft

51 Maher Dr, Norwalk, CT 06850

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

$2,975,000

3 beds3.5 baths3,040 sq ft

321 Oenoke Rdg, 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 297 Shore Rd, Greenwich, CT 06830, 6 beds, 7 baths

$9,950,000

6 beds7 baths10,130 sq ft

297 Shore Rd, Greenwich, CT 06830

Property at 228 Woodrow Ave, Southport, CT 06890, 3 beds, 2 baths

$1,180,000

3 beds2 baths2,253 sq ft

228 Woodrow Ave, Southport, CT 06890

Property at 75 Hemlock St, Bridgeport, CT 06605, 3 beds, 2 baths

$499,900

3 beds2 baths1,300 sq ft

75 Hemlock St, Bridgeport, CT 06605

Property at 495 Cutspring Rd, Stratford, CT 06614, 4 beds, 1.5 baths

$599,000

4 beds1.5 baths1,998 sq ft

495 Cutspring Rd, Stratford, CT 06614

Property at 1285 Hope St #12, Stamford, CT 06907, 2 beds, 1 bath

$417,000

2 beds1 bath800 sq ft

1285 Hope St #12, Stamford, CT 06907

Property at 1282 Park Ave, Bridgeport, CT 06604, 6 beds, 4 baths

$489,500

6 beds4 baths2,714 sq ft

1282 Park Ave, Bridgeport, CT 06604

Property at 91 Strawberry Hill Ave #240, Stamford, CT 06902, 1 bed, 1 bath

$245,000

1 bed1 bath725 sq ft

91 Strawberry Hill Ave #240, Stamford, CT 06902

Property at 19 Roosevelt Rd, Westport, CT 06880, 4 beds, 3.5 baths

$4,250,000

4 beds3.5 baths2,762 sq ft

19 Roosevelt Rd, Westport, CT 06880

Property at 51-71 Park Ave Unit 2-51, Danbury, CT 06810, 2 beds, 1 bath

$225,000

2 beds1 bath701 sq ft

51-71 Park Ave Unit 2-51, Danbury, CT 06810

Property at 49 Sunrise Ave, Trumbull, CT 06611, 4 beds, 3 baths

$850,000

4 beds3 baths1,968 sq ft

49 Sunrise Ave, Trumbull, CT 06611

Property at 71 Country Rd, Fairfield, CT 06824, 3 beds, 3 baths

$879,000

3 beds3 baths1,939 sq ft

71 Country Rd, Fairfield, CT 06824

Property at 1 Sunrise Rd Unit B, Westport, CT 06880, 2 beds, 2.5 baths

$995,000

2 beds2.5 baths1,202 sq ft

1 Sunrise Rd Unit B, Westport, CT 06880

Property at 99 William St Unit B, Bridgeport, CT 06608, 3 beds, 1.5 baths

$179,900

3 beds1.5 baths1,121 sq ft

99 William St Unit B, Bridgeport, CT 06608

Property at 295 & 297 Shore Rd, Old Greenwich, CT 06830, 6 beds, 7 baths

$14,500,000

6 beds7 baths10,130 sq ft

295 & 297 Shore Rd, Old Greenwich, CT 06830

Property at 23 Clara Dr, Norwalk, CT 06851, 3 beds, 2 baths

$799,000

3 beds2 baths1,824 sq ft

23 Clara Dr, Norwalk, CT 06851

Property at 9 Lafayette Ct, Greenwich, CT 06830, 2 beds, 2.5 baths

$7,495,000

2 beds2.5 baths3,890 sq ft

9 Lafayette Ct, Greenwich, CT 06830

Property at 291-293 Bruce Ave, Stratford, CT 06615, 8 beds, 3 baths

$745,000

8 beds3 baths3,380 sq ft

291-293 Bruce Ave, Stratford, CT 06615

Property at 216 Granfield Ave, Bridgeport, CT 06610, 4 beds, 1 bath

$469,500

4 beds1 bath1,152 sq ft

216 Granfield Ave, Bridgeport, CT 06610

Property at 208 Birmingham St, Bridgeport, CT 06606, 1 bed, 1 bath

$274,900

1 bed1 bath1,149 sq ft

208 Birmingham St, Bridgeport, CT 06606

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Based on information submitted to the MLS GRID as of Sun Nov 01 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 861 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, 754 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 905 condos, 1 townhouse, and 219 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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