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:
Set on beautifully landscaped 1.41 acres, this distinguished Tudor-style estate with water views combines fine craftsmanship, abundant natural light and seamless indoor-outdoor living. Expanded in 2006 and renovated in 2022 with meticulous attention to detail, the home has been impeccably maintained. The outdoor oasis features a pool, pool house with kitchenette and powder room, outdoor fireplace, lush lawn and hot tub. Inside, a dramatic double-height billiards room with custom bar opens to an expansive terrace. Six bedrooms feature custom Bliss Nor-Am windows and exquisite millwork. The primary suite offers vaulted ceilings and a spa-style bath with steam shower. Four-car garage and full-

$9,950,000

6 beds7 baths10,130 sq ft

297 Shore Rd, Greenwich, CT 06830

Outdoor fireplace • Water views • Hot tub

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Charming Antique Colonial with Stunning Lake Views -- Welcome to this alluring antique Colonial farmhouse, built circa 1900, where historic character meets modern updates. This 3-bedroom, 2-full-bath home offers 1,647 square feet of living space, beautiful hardwood floors and recessed lighting throughout, wood-beam ceilings, and a striking stone fireplace in the main living room. The large double-insulated windows capture beautiful property and lake views from multiple rooms, especially the living room and dining room and the primary bedroom. A main-level bedroom with a full bath offers flexibility for guests or one-level living, or could also serve as an office, den or playroom. The primar

$685,000

3 beds2 baths1,647 sq ft

17 Fire Hill Rd, Ridgefield, CT 06877

Private deck • Lake views • Spacious lawn

OPEN SUN, 12PM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Move right in to this freshly painted (inside & out) turnkey home featuring new windows throughout and updated insulation. Half the property has been modernized with updated plumbing and electrical wiring for complete peace of mind. The main level boasts a sun-filled living room with refaced fireplace, home office/sumroom, formal dining room, and a brand-new eat-in kitchen complete with sleek custom cabinets, stunning island, and new countertops. Upstairs, find 3 bedrooms-including a primary suite with a private sunroom-a newly renovated full bath, and a walk-up finished 3rd level for a family room space . Complete with a full lower level (laundry & storage), large 2-car garage,

$730,000

3 beds1.5 baths1,510 sq ft

155 Moody Ave, Fairfield, CT 06825

Freshly painted • New windows • Updated insulation

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

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 15 Flat Swamp Road! This beautifully maintained, move-in-ready 3-bedroom, 2-full-bath home offers a level of pride of ownership rarely seen today. The remodeled kitchen (2020) features crisp white cabinetry, expansive granite countertops, stainless steel appliances, and subway tile backsplash. Gleaming hardwood floors add warmth throughout. The updated primary suite (2025) offers a new full bath, while two generously sized bedrooms share an updated hall bath. One bedroom features beautiful built-ins while both utilize a Jack-and-Jill-style walk-in closet. Major improvements include a new septic system (2018), heat pump mini-splits for AC (2022) that cool the entire space, new win

$609,000

3 beds2 baths1,616 sq ft

15 Flat Swamp Rd, Newtown, CT 06470

Remodeled kitchen • New full bath • 2.07 acre lot

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 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 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 716 Cheese Spring Rd, New Canaan, CT 06840, 5 beds, 5.5 baths

$3,600,000

5 beds5.5 baths5,135 sq ft

716 Cheese Spring Rd, New Canaan, CT 06840

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

$480,000

4 beds1.5 baths1,896 sq ft

162 Anson St, Stratford, CT 06614

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

$3,300,000

3 beds3.5 baths3,040 sq ft

321 Oenoke Rdg, New Canaan, CT 06840

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 29 Mohawk Dr, Easton, CT 06612, 3 beds, 2 baths

$649,000

3 beds2 baths1,270 sq ft

29 Mohawk Dr, Easton, CT 06612

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 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 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 11 Cardinal Pl, Stratford, CT 06614, 3 beds, 1 bath

$355,700

3 beds1 bath1,267 sq ft

11 Cardinal Pl, Stratford, CT 06614

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

$249,000

2 beds2 baths1,042 sq ft

145 Canal St #13, Shelton, CT 06484

Property at 9 Cornwall Rd, Norwalk, CT 06850, 3 beds, 1.5 baths

$715,000

3 beds1.5 baths1,496 sq ft

9 Cornwall Rd, Norwalk, CT 06850

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

$435,000

2 beds1 bath800 sq ft

1285 Hope St #12, Stamford, CT 06907

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 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 52 Lafayette Pl Unit 2B, Greenwich, CT 06830, 1 bed, 1 bath

$479,000

1 bed1 bath585 sq ft

52 Lafayette Pl Unit 2B, Greenwich, CT 06830

Property at 28 Brookside Ave, Bridgeport, CT 06606, 4 beds, 3 baths

$649,900

4 beds3 baths2,554 sq ft

28 Brookside Ave, Bridgeport, CT 06606

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 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 8 Driftway Rd Unit E1, Danbury, CT 06811, 3 beds, 1.5 baths

$385,000

3 beds1.5 baths1,500 sq ft

8 Driftway Rd Unit E1, Danbury, CT 06811

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 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 73 Yale St, Bridgeport, CT 06605, 5 beds, 3 baths

$570,000

5 beds3 baths3,044 sq ft

73 Yale St, Bridgeport, CT 06605

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 33-35 Ash St, Bridgeport, CT 06605, 4 beds, 2 baths

$479,900

4 beds2 baths2,409 sq ft

33-35 Ash St, Bridgeport, CT 06605

Property at 351 Wilton Rd W, Ridgefield, CT 06877, 5 beds, 6 baths

$2,295,000

5 beds6 baths5,410 sq ft

351 Wilton Rd W, Ridgefield, CT 06877

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 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 Fri Oct 23 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 876 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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