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:
Tucked along a tranquil lane, mere steps from the soft sands of Westport's coveted Compo Beach, 19 Roosevelt Road is coastal living at its most refined. This picture-perfect residence of four bedrooms and three and a half baths pairs timeless elegance with effortless comfort. It was reimagined from the studs up in 2019 and is fully FEMA-compliant, with two light-filled levels and every modern convenience. On the main level, a gracious living room sets the tone, framed by custom built-in bookcases and warmed by a gas fireplace. The chef's kitchen is the heart of the home. It has a generous center island, a Sub-Zero refrigerator, a Wolf gas range and a dedicated wine refrigerator. Beyond it,

$4,250,000

4 beds3.5 baths2,762 sq ft

19 Roosevelt Rd, Westport, CT 06880

Gas fireplace • Wolf gas range • Chef's kitchen

OPEN TODAY, 12PM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
SELLER WILL PAY UP TO 3% CLOSING COST & PREPAIDS ACCDEPTED OFFER! POOL, FENCED YARD, SCREENED PORCH & FIREPLACE - WELCOME TO 51 MAHER DRIVE! This inviting 3-bedroom, 1-1.5bath split-level offers the perfect combination of indoor comfort, outdoor enjoyment and convenient Norwalk living. Situated on a . 20-acre lot, the home features 6 rooms with a versatile split-level layout, a warm and inviting living area with fireplace, 3 bedrooms above with a possible 4th converting family room by placing a door at stairs, 1 full 1 Half baths and a one-car garage. Step outside and enjoy your own backyard retreat! The fenced-in yard provides privacy and plenty of room for entertaining, recrea

$699,900

3 beds1.5 baths1,076 sq ft

51 Maher Dr, Norwalk, CT 06850

Fenced yard • Convenient access • Screened porch

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:
Step into the timeless charm of Bethel with this classic antique Colonial, cherished by the same family for almost 50 years. Rich with character and awaiting its next chapter, this four-bedroom home offers a delightful canvas for bringing your vision to life. Original details and a classic layout provide an inviting foundation for a truly special residence. Once refreshed, the combination of historic character and modern finishes will create a remarkable home in one of Bethel's most convenient locations. This home is being sold As-Is, and a new boiler and hot water heater, both installed in 2025, provide a great head start. The compact parcel means less time devoted to yard maintenance and

$359,000

4 beds1.5 baths1,482 sq ft

72 Chestnut St, Bethel, CT 06801

Convenient locations • Original details • Historic character

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Set on a quiet street in the desirable Cranbury neighborhood, this beautifully maintained 4-bedroom, 3 full bath home offers a wonderful blend of comfort, updates, and flexible living space. The main level features hardwood floors, a welcoming living room, dining room with fireplace, and a spacious kitchen with granite countertops, stainless steel appliances, and abundant cabinetry. The home is filled with natural light and includes updated bathrooms and a partially finished lower level ideal for a family room, home office, gym, recreation area, or guests. The lower level walks out to a large patio and private in-ground pool featuring new marble coping, a newer pool pump motor, and pool hea

$899,900

4 beds3 baths2,346 sq ft

59 Creeping Hemlock Dr, Norwalk, CT 06851

Spacious kitchen • Abundant cabinetry • Granite countertops

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 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 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 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 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 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 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 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 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 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 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 145 Canal St #13, Shelton, CT 06484, 2 beds, 2 baths

$229,000

2 beds2 baths1,042 sq ft

145 Canal St #13, Shelton, CT 06484

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 175 Eaton St, Bridgeport, CT 06604, 3 beds, 1.5 baths

$449,999

3 beds1.5 baths2,000 sq ft

175 Eaton St, Bridgeport, CT 06604

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 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 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 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 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 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 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 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 15 Flat Swamp Rd, Newtown, CT 06470, 3 beds, 2 baths

$609,000

3 beds2 baths1,616 sq ft

15 Flat Swamp Rd, Newtown, CT 06470

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 73-75 Fairlawn Ave, Bridgeport, CT 06605, 6 beds, 3 baths

$799,000

6 beds3 baths3,487 sq ft

73-75 Fairlawn Ave, Bridgeport, CT 06605

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 3 Alfred Ct, Stratford, CT 06615, 2 beds, 1.5 baths

$380,000

2 beds1.5 baths1,074 sq ft

3 Alfred Ct, Stratford, CT 06615

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 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 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 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 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 95 Disbrow St, Stratford, CT 06614, 3 beds, 1 bath

$459,000

3 beds1 bath1,352 sq ft

95 Disbrow St, Stratford, CT 06614

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

$489,999

4 beds2 baths1,227 sq ft

406 Lakeside Dr, Bridgeport, CT 06606

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Based on information submitted to the MLS GRID as of Sat Oct 24 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 886 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 895 condos, 1 townhouse, and 218 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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