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:
Welcome to 21 Hill Street, a charming 1925 Colonial offering 1,204 square feet of comfortable living space on a 0.18-acre lot in Norwalk. Featuring a possible 4 bedrooms and 2 bathrooms, this home blends vintage character with a functional multi-level layout. The main level welcomes you with an open-concept flow connecting the living room, dining room, and a spacious kitchen. It is complemented by a convenient main-floor primary bedroom, a full bathroom, and a coat closet near the entrance--great for multi-generational living. Upstairs, you will find three additional bedrooms arranged around a central hallway along with a second full bathroom, providing plenty of private sleeping quarters.

$599,000

4 beds2 baths1,204 sq ft

21 Hill St, Norwalk, CT 06850

Back patio space • Dedicated workshop • New trex deck

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Room to grow, space to entertain, and exceptional flexibility-this Colonial in the heart of Monroe offers a 5-bedroom setup on 1.2 acres of level, partially fenced land. With five rooms currently used as bedrooms, the home provides options for guests, work, and hobbies, adding substantial appeal at this price point. Town tax records designate the home as three bedrooms. Inside, the spacious living room features soaring cathedral ceilings, exposed wood beams, and beautiful hardwood floors. The kitchen offers stainless steel appliances and a peninsula with seating, opening to the dining area for easy everyday living and entertaining. Double doors lead to a large Trex deck overlooking the priv

$599,000

3 beds2 baths2,130 sq ft

148 Cross Hill Rd, Monroe, CT 06468

1.2 acres • Private backyard • 5 bedroom setup

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Step into the timeless charm of this beautifully maintained 1912 Colonial, rich with Victorian-inspired character and modern updates. A Home Warranty is included, providing added peace of mind for the new owner. Throughout the home, you'll find original woodwork, soaring ceilings, spacious rooms, decorative pillars separating the living and dining areas, and classic hardwood floors that showcase the home's historic appeal. The updated kitchen blends modern convenience with period charm and features newer appliances, including a refrigerator, dishwasher, gas range, microwave, washer, and dryer. The home offers 3 bedrooms and 1.5 baths, along with exciting possibilities on the third level. Pr

$699,000

3 beds1.5 baths1,766 sq ft

60 Nashvile Rd, Bethel, CT 06801

Original wood trim • Decorative pillars • New appliances

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
A Hidden Gem in a Great Location! Discover the potential of this spacious Cape-style home, offering 3 bedrooms, 2 full bathrooms, and plenty of room to make it your own! Situated on a generous . 75-acre level corner lot, this property is full of possibilities for homeowners looking to create their dream home. The main level features a spacious kitchen, a comfortable den, dining room, living room and an additional bedroom or family room to suit your needs. Hardwood floors lie beneath all carpeting, and the generously sized rooms offer plenty of space for living and entertaining. Just off the family room, a greenhouse offers the opportunity to create a beautiful sunroom by relocating one wall

$550,000

3 beds2 baths1,879 sq ft

1 Clearview Ave, Bethel, CT 06801

Spacious kitchen • Full-size basement • Comfortable den

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Location, location, location! Sunny and spacious condominium offers a living room, dining room, eat-in kitchen, 1 bedroom, 1 full bathroom, plenty of closet space, and a balcony with views. Fountain Terrace Complex is located within minutes of parks, shopping centers, restaurants, theaters, and all downtown Stamford amenities. Enjoy access to an in-ground pool, fitness center, kids' playground, and clubhouse. The building has 24-hour security, laundry in the basement, and a reserved parking space. Common charges include heat, hot water, and cooking gas. Pets are allowed! Excellent opportunity for first-time home buyers. Why pay rent when you can own!

$245,000

1 bed1 bath725 sq ft

91 Strawberry Hill Ave #240, Stamford, CT 06902

In-ground pool • Balcony with views • Fitness center

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

$695,000

5 beds2 baths2,746 sq ft

259 Pauline St, Stratford, CT 06615

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 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 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 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 541 Sasco Hill Rd, Fairfield, CT 06824, 5 beds, 7.5 baths

$6,500,000

5 beds7.5 baths11,999 sq ft

541 Sasco Hill Rd, Fairfield, CT 06824

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

$274,900

1 bed1 bath1,149 sq ft

208 Birmingham St, Bridgeport, CT 06606

Property at 17 Fire Hill Rd, Ridgefield, CT 06877, 3 beds, 2 baths

$685,000

3 beds2 baths1,647 sq ft

17 Fire Hill Rd, Ridgefield, CT 06877

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 39 Sorghum Rd, Shelton, CT 06484, 3 beds, 3 baths

$639,999

3 beds3 baths2,442 sq ft

39 Sorghum Rd, Shelton, CT 06484

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

$730,000

3 beds1.5 baths1,510 sq ft

155 Moody Ave, Fairfield, CT 06825

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 307 Courtland Ave, Stamford, CT 06906, 3 beds, 1 bath

$625,000

3 beds1 bath1,353 sq ft

307 Courtland Ave, Stamford, CT 06906

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

$429,000

2 beds1 bath800 sq ft

1285 Hope St #12, Stamford, CT 06907

Property at 67 Sultan St, Stratford, CT 06614, 3 beds, 1.5 baths

$550,000

3 beds1.5 baths1,653 sq ft

67 Sultan St, Stratford, CT 06614

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 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 35 Beardsley Pkwy, Trumbull, CT 06611, 3 beds, 1.5 baths

$620,000

3 beds1.5 baths1,518 sq ft

35 Beardsley Pkwy, Trumbull, CT 06611

Property at 402 Patterson Ave, Stratford, CT 06614, 2 beds, 1 bath

$374,900

2 beds1 bath1,008 sq ft

402 Patterson Ave, Stratford, CT 06614

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 235-237 Hanover St, Bridgeport, CT 06605, 6 beds, 2 baths

$575,000

6 beds2 baths2,390 sq ft

235-237 Hanover St, Bridgeport, CT 06605

Property at 406 Lakeside Dr, Bridgeport, CT 06606, 4 beds, 2 baths

$489,999

4 beds2 baths1,227 sq ft

406 Lakeside Dr, Bridgeport, CT 06606

Property at 19 Topstone Dr, Bethel, CT 06801, 3 beds, 2 baths

$549,900

3 beds2 baths1,500 sq ft

19 Topstone Dr, Bethel, CT 06801

Property at 62 Longmeadow Rd, Shelton, CT 06484, 4 beds, 2.5 baths

$659,000

4 beds2.5 baths2,788 sq ft

62 Longmeadow Rd, Shelton, CT 06484

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 64 Garfield Ave, Danbury, CT 06810, 3 beds, 1.5 baths

$545,000

3 beds1.5 baths1,830 sq ft

64 Garfield Ave, Danbury, CT 06810

Property at 276 Nichols Ter, Stratford, CT 06614, 3 beds, 1.5 baths

$489,900

3 beds1.5 baths1,710 sq ft

276 Nichols Ter, Stratford, CT 06614

Property at 23 Park Ln, Norwalk, CT 06854, 4 beds, 3.5 baths

$1,995,000

4 beds3.5 baths2,760 sq ft

23 Park Ln, Norwalk, CT 06854

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Based on information submitted to the MLS GRID as of Mon Oct 26 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 887 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 896 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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