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:
Don't miss this Wonderful Opportunity to own a ranch style home in the Lakeside Drive Community across the street from the Lake Forest lake. The Living Room with fireplace opens to the updated Kitchen with SS appliances, granite countertops and breakfast bar. The kitchen has an access door to the outside. 3 Bedrooms on the main level with Full Hall Bath Fully finished Walkout Lower Level features large Family Room plus another room which could be an office or other flexible space. Spacious Full Bath plus Laundry and Mechanical Room also located on this level. Gas Heat & Hot Water. Hardwood floors in Living Room and Bedrooms 2 Car heated Garage with workshop has interior access door t

$489,999

4 beds2 baths1,227 sq ft

406 Lakeside Dr, Bridgeport, CT 06606

Flexible space • Large family room • Walkout lower level

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to this inviting move in ready three-bedroom home in a desirable Fairfield Southport, where comfortable living, thoughtful updates, and everyday convenience meet together. Set in a peaceful residential neighborhood, this home offers a wonderful balance of privacy and accessibility to both Fairfield's and Westport shopping, dining, parks. Fairfield's vibrant town amenities beaches, and train station all within easy reach. Step inside to bright, welcoming living spaces designed for both everyday life and entertaining. The open kitchen serves as the heart of the home, featuring granite countertops and a seamless connection to the adjoining living and dining areas. The open layout creat

$1,180,000

3 beds2 baths2,253 sq ft

228 Woodrow Ave, Southport, CT 06890

Thoughtful updates • Finished basement • Move in ready

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Tucked away on a beautifully landscaped lot in Shelton's sought-after Huntington neighborhood, this exceptional home offers the perfect blend of comfort, space, and resort-style living. Inside, you'll find spacious bedrooms, soaring cathedral ceilings, and a unique loft-style primary suite that creates an open and inviting feel. The enclosed patio provides additional year-round living space, perfect for entertaining or simply unwinding. Outside, escape to your private backyard retreat featuring a sparkling in-ground pool, a peaceful koi pond, and mature landscaping that offers beauty and privacy. Whether hosting family and friends or enjoying a quiet evening outdoors, this home is designed

$639,999

3 beds3 baths2,442 sq ft

39 Sorghum Rd, Shelton, CT 06484

Koi pond • In-ground pool • Landscaped lot

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Charming 1912 Colonial with Victorian Character and Expansion Potential. Home has beautiful Victorian-inspired details throughout, including original wood trim, high ceilings, large rooms, decorative pillars separating the living and dining rooms, and timeless hardwood floors that showcase the home's historic charm. The updated kitchen is equipped with new appliances, including a refrigerator, dishwasher, gas stove, microwave, and a new washer and dryer, offering modern convenience, while preserving the home's character. This home offers 3 bedrooms and 11/2 baths, with additional possibilities on the 3rd level. Previously used as living space, the unfinished third level already features pai

$750,000

3 beds1.5 baths1,766 sq ft

60 Nashvile Rd, Bethel, CT 06801

Original wood trim • Decorative pillars • New appliances

OPEN SAT, 1:30PM TO 3:30PM

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
A one-level opportunity near Wooster Park: renovate, reimagine, make it yours. Bring your vision to this well-located Stratford home and unlock its potential. Situated on a corner lot adjacent to Wooster Park, this 3-bedroom, 1-bath home offers a practical single level floor plan, oversized 1-car garage, driveway parking, central air conditioning and gas baseboard heat. At approximately 1044 square feet, the home provides a manageable footprint with plenty of opportunity for renovation and personalization. This property conveys AS IS

$379,000

3 beds1 bath1,044 sq ft

20 Karen Ave, Stratford, CT 06614

Gas baseboard heat • Corner lot • 9,583 sq ft lot

Property at 162 Anson St, Stratford, CT 06614, 4 beds, 1.5 baths

$500,000

4 beds1.5 baths1,896 sq ft

162 Anson St, Stratford, CT 06614

Property at 1885 Old Town Rd, Bridgeport, CT 06606, 3 beds, 1.5 baths

$510,000

3 beds1.5 baths1,092 sq ft

1885 Old Town Rd, Bridgeport, CT 06606

Property at 87 Giles Hill Rd, Redding, CT 06896, 3 beds, 2 baths

$747,500

3 beds2 baths2,115 sq ft

87 Giles Hill Rd, Redding, CT 06896

Property at 190 North St, Greenwich, CT 06830, 7 beds, 9.5 baths

$12,750,000

7 beds9.5 baths12,176 sq ft

190 North St, Greenwich, CT 06830

Property at 110 Ruby Ln, Stratford, CT 06614, 3 beds, 1.5 baths

$469,000

3 beds1.5 baths1,548 sq ft

110 Ruby Ln, Stratford, CT 06614

Property at 73 Cos Cob Ave, Greenwich, CT 06830, 5 beds, 3 baths

$1,395,000

5 beds3 baths2,805 sq ft

73 Cos Cob Ave, Greenwich, CT 06830

Property at 19 Ridgeway St, Stamford, CT 06907, 3 beds, 2 baths

$630,000

3 beds2 baths1,850 sq ft

19 Ridgeway St, Stamford, CT 06907

Property at 633 Steamboat Rd Apt 4, Greenwich, CT 06830, 2 beds, 2.5 baths

$4,550,000

2 beds2.5 baths2,157 sq ft

633 Steamboat Rd Apt 4, Greenwich, CT 06830

Property at 16 Nathan Hale Dr, Norwalk, CT 06854, 5 beds, 5.5 baths

$24,000,000

5 beds5.5 baths7,369 sq ft

16 Nathan Hale Dr, Norwalk, CT 06854

Property at 30 Court St, Stamford, CT 06902, 4 beds, 4 baths

$1,045,000

4 beds4 baths3,430 sq ft

30 Court St, Stamford, CT 06902

Property at 10 Hillwood Pl, Norwalk, CT 06850, 4 beds, 2.5 baths

$699,000

4 beds2.5 baths2,150 sq ft

10 Hillwood Pl, Norwalk, CT 06850

Property at 55 Oil Mill Rd #26, Danbury, CT 06810, 1 bed, 1 bath

$300,000

1 bed1 bath1,105 sq ft

55 Oil Mill Rd #26, Danbury, CT 06810

Property at 10 Prospect Dr, Stratford, CT 06615, 4 beds, 1.5 baths

$449,000

4 beds1.5 baths1,222 sq ft

10 Prospect Dr, Stratford, CT 06615

Property at 105 Old Dike Rd, Trumbull, CT 06611, 4 beds, 2 baths

$900,000

4 beds2 baths2,376 sq ft

105 Old Dike Rd, Trumbull, CT 06611

Property at 73 Cos Cob Ave, Cos Cob, CT 06807, 5 beds, 3 baths

$1,395,000

5 beds3 baths2,805 sq ft

73 Cos Cob Ave, Cos Cob, CT 06807

Property at 743 Iranistan Ave, Bridgeport, CT 06605, 8 beds, 3 baths

$599,000

8 beds3 baths3,010 sq ft

743 Iranistan Ave, Bridgeport, CT 06605

Property at 81 Louisiana Ave #81, Bridgeport, CT 06610, 2 beds, 1 bath

$160,000

2 beds1 bath948 sq ft

81 Louisiana Ave #81, Bridgeport, CT 06610

Property at 75 Westville Ave, Danbury, CT 06810, 3 beds, 1 bath

$489,900

3 beds1 bath1,352 sq ft

75 Westville Ave, Danbury, CT 06810

Property at 383 Harral Ave, Bridgeport, CT 06604, 9 beds, 3 baths

$899,900

9 beds3 baths2,982 sq ft

383 Harral Ave, Bridgeport, CT 06604

Property at 24-22 Evers Ct, Bridgeport, NY 06610, 4 beds, 2 baths

$499,000

4 beds2 baths— sq ft

24-22 Evers Ct, Bridgeport, NY 06610

Listing by RE/MAX Voyage Realty

Property at 7 Hayes Ave, Norwalk, CT 06855, 3 beds, 2 baths

$685,000

3 beds2 baths1,434 sq ft

7 Hayes Ave, Norwalk, CT 06855

Property at 77 Ridge Rd, Stratford, CT 06614, 4 beds, 2.5 baths

$625,000

4 beds2.5 baths2,700 sq ft

77 Ridge Rd, Stratford, CT 06614

Property at 26 Hickok Ave, Bethel, CT 06801, 4 beds, 2 baths

$499,000

4 beds2 baths1,650 sq ft

26 Hickok Ave, Bethel, CT 06801

Property at 51 Oronoque Trl, Shelton, CT 06484, 2 beds, 1 bath

$374,900

2 beds1 bath1,002 sq ft

51 Oronoque Trl, Shelton, CT 06484

Property at 94 Sheppard St, Stratford, CT 06614, 3 beds, 1.5 baths

$535,000

3 beds1.5 baths1,558 sq ft

94 Sheppard St, Stratford, CT 06614

Property at 33 Circle Dr, Stratford, CT 06614, 1 bed, 1 bath

$375,000

1 bed1 bath588 sq ft

33 Circle Dr, Stratford, CT 06614

Property at 259 Pauline St, Stratford, CT 06615, 5 beds, 2 baths

$799,900

5 beds2 baths2,746 sq ft

259 Pauline St, Stratford, CT 06615

Property at 1 Willowbrook Ct #1, Stamford, CT 06902, 2 beds, 1.5 baths

$405,000

2 beds1.5 baths907 sq ft

1 Willowbrook Ct #1, Stamford, CT 06902

Property at 111 Mercer St, Stratford, CT 06614, 3 beds, 2.5 baths

$499,900

3 beds2.5 baths1,870 sq ft

111 Mercer St, Stratford, CT 06614

Property at 38 Reynolds Dr, Fairfield, CT 06824, 3 beds, 2.5 baths

$869,000

3 beds2.5 baths1,898 sq ft

38 Reynolds Dr, Fairfield, CT 06824

Property at 59 Rennell St #19, Bridgeport, CT 06604, 1 bed, 1 bath

$99,999

1 bed1 bath385 sq ft

59 Rennell St #19, Bridgeport, CT 06604

Property at 44 Lavelle Ave, New Fairfield, CT 06812, 1 bed, 1 bath

$399,999

1 bed1 bath789 sq ft

44 Lavelle Ave, New Fairfield, CT 06812

Property at 7 Peaceful Ln, Norwalk, CT 06851, 3 beds, 1 bath

$795,000

3 beds1 bath1,278 sq ft

7 Peaceful Ln, Norwalk, CT 06851

Property at 26 Powell Ter, Bridgeport, CT 06604, 4 beds, 1.5 baths

$498,990

4 beds1.5 baths2,140 sq ft

26 Powell Ter, Bridgeport, CT 06604

Property at 1076 E Main St #1, Stamford, CT 06902, 2 beds, 1 bath

$299,900

2 beds1 bath708 sq ft

1076 E Main St #1, Stamford, CT 06902

Property at 17 Greenbriar Cir, Fairfield, CT 06824, 4 beds, 1.5 baths

$685,000

4 beds1.5 baths1,612 sq ft

17 Greenbriar Cir, Fairfield, CT 06824

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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 842 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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