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:
3 houses on 1 property!! Tucked away on 6 private acres in the highly desirable Aspetuck section is this rare opportunity to own 3 individual residences on one parcel. Whether envisioned as a multi-generational compound, an investment property, or a private homestead with in-law/ guest/rentals, the possibilities are as unique as the property itself. #25 (Building 1 on field card) is the first home you arrive at along the driveway. Built in 1930 and modernized in 1985, this charming colonial features 3/4 bedrooms, 2,284 sqft, a fireplace, gambrel barn, chicken coop, raised garden planters, attached garage under house, and detached garage/carport. Plus solar panels were installed about 10 yea

$1,248,000

3 beds2 baths2,284 sq ft

25-35-37 Mills Ln, Easton, CT 06612

Private acres • Investment property • Modernized in 1985

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
This timeless estate, situated in an exclusive private association moments from town, masterfully blends turn-of-the-century grandeur with 21st-century luxury. The main house was extensively renovated and expanded in 2006 by award-winning architects Austin Patterson Disston. It showcases grand-scale rooms, soaring ceilings, and impeccable millwork. In 2016 the current owners made it their own by adding a wine cellar and renovating the primary suite to the same outstanding standards. The main house features six ensuite bedrooms and 7.3 baths. The expansive primary suite is a true sanctuary, complete with private office, custom walk-in dressing room, and a large balcony overlooking the ground

$8,495,000

6 beds8.5 baths8,704 sq ft

7 Calhoun Dr, Greenwich, CT 06831

Over-sized pool • Wine cellar • Large balcony

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Now under construction at 94 Soundview Road in a sought-after South Ridgefield neighborhood, this exceptional modern farmhouse will showcase superior craftsmanship, quality construction, and thoughtfully selected luxury finishes throughout. Built by a highly regarded second-generation Ridgefield builder, the home offers 5 bedrooms and 4.5 baths with a sophisticated design created for both everyday living and effortless entertaining. A welcoming front porch and stone walkway set the tone for the home, opening to a spacious and beautifully appointed interior. The main level features an impressive eat-in chef's kitchen, expansive family room with fireplace, formal dining room, and living room,

$2,200,000

5 beds4.5 baths4,592 sq ft

94 Soundview Rd, Ridgefield, CT 06877

Quality construction • Luxury finishes • Modern farmhouse

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to this beautifully maintained classic 1938 Ranch located in the heart of the Center District. This home offers single level living space with hardwood floors throughout. The inviting living room is highlighted with a beautiful stone fireplace, custom built-ins and a soaring ceiling. The kitchen boasts granite countertops, tile flooring, gas for cooking, plenty of cabinetry and a bright skylight that fills the space with natural light. A mud room is conveniently located off the kitchen. Both bedrooms are on the main level, including a huge primary bedroom, with an oversized double closet and a private en suite bath. The second bedroom has custom built-ins with plenty of storage alon

$530,000

2 beds2 baths1,168 sq ft

464 Church Hill Rd, Trumbull, CT 06611

Bright skylight • Custom built-ins • Stone fireplace

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 160 Cedar Road, a truly special farmhouse in Southport that has been thoughtfully renovated and reimagined. Filled with warmth, character, and modern updates, this unique property beautifully blends timeless charm with contemporary comfort. Privately set and abutting Aspetuck Land Trust property, the 2-bedroom, possible 3-bedroom, 1.5-bath home enjoys a beautiful natural setting on 4.45 acres while being conveniently close to all that Southport and Fairfield have to offer, including beaches, shopping, restaurants, I95 and the train. The property features a saltwater inground pool, pool cabana, tanning deck, and outdoor shower-creating an exceptional setting for relaxing and enter

$1,699,000

2 beds1.5 baths2,131 sq ft

160 Cedar Rd, Southport, CT 06890

Tanning deck • Three barns • Pool cabana

Property at 394 Tashua Rd, Trumbull, CT 06611, 5 beds, 3.5 baths

$949,900

5 beds3.5 baths3,078 sq ft

394 Tashua Rd, Trumbull, CT 06611

Property at 145 Canal St #8, Shelton, CT 06484, 2 beds, 2 baths

$259,900

2 beds2 baths1,180 sq ft

145 Canal St #8, Shelton, CT 06484

Property at 57-59 Fairview Ave, Bridgeport, CT 06606, 6 beds, 2 baths

$689,900

6 beds2 baths2,962 sq ft

57-59 Fairview Ave, Bridgeport, CT 06606

Property at 297 Rock Rimmon Rd, Stamford, CT 06903, 5 beds, 5.5 baths

$1,585,000

5 beds5.5 baths4,022 sq ft

297 Rock Rimmon Rd, Stamford, CT 06903

Property at 19 Olmstead Rd, Redding, CT 06896, 2 beds, 2 baths

$499,900

2 beds2 baths1,125 sq ft

19 Olmstead Rd, Redding, CT 06896

Property at 325 Lafayette St #9105, Bridgeport, CT 06604, 3 beds, 3 baths

$525,000

3 beds3 baths6,360 sq ft

325 Lafayette St #9105, Bridgeport, CT 06604

Property at 52 Merrimac St, Danbury, CT 06810, 2 beds, 1.5 baths

$349,999

2 beds1.5 baths1,075 sq ft

52 Merrimac St, Danbury, CT 06810

Property at 508 Round Hill Rd, Greenwich, CT 06831, 6 beds, 4.5 baths

$5,995,000

6 beds4.5 baths4,629 sq ft

508 Round Hill Rd, Greenwich, CT 06831

Property at 64-66 Hill St, Bridgeport, CT 06606, 5 beds, 2 baths

$485,000

5 beds2 baths2,452 sq ft

64-66 Hill St, Bridgeport, CT 06606

Property at 5 Tod Rd, Norwalk, CT 06851, 4 beds, 2 baths

$834,999

4 beds2 baths1,619 sq ft

5 Tod Rd, Norwalk, CT 06851

Property at 180 Dupont Pl, Bridgeport, CT 06610, 4 beds, 2 baths

$599,900

4 beds2 baths1,620 sq ft

180 Dupont Pl, Bridgeport, CT 06610

Property at 2029 Kings Hwy, Fairfield, CT 06824, 6 beds, 3 baths

$1,200,000

6 beds3 baths2,487 sq ft

2029 Kings Hwy, Fairfield, CT 06824

Property at 68 Oronoque Trl, Shelton, CT 06484, 4 beds, 2 baths

$389,999

4 beds2 baths1,737 sq ft

68 Oronoque Trl, Shelton, CT 06484

Property at 16 Raymond St, New Canaan, CT 06840, 5 beds, 2 baths

$1,250,000

5 beds2 baths1,936 sq ft

16 Raymond St, New Canaan, CT 06840

Property at 152 George Washington Hwy, Ridgefield, CT 06877, 4 beds, 2.5 baths

$1,275,000

4 beds2.5 baths4,006 sq ft

152 George Washington Hwy, Ridgefield, CT 06877

Property at 523 Newfield Ave, Stamford, CT 06905, 3 beds, 2 baths

$739,000

3 beds2 baths1,624 sq ft

523 Newfield Ave, Stamford, CT 06905

Property at 125 West Rd, New Canaan, CT 06840, 6 beds, 6.5 baths

$4,595,000

6 beds6.5 baths6,246 sq ft

125 West Rd, New Canaan, CT 06840

Property at 65 Glenwood Ave, Stratford, CT 06614, 3 beds, 1 bath

$470,000

3 beds1 bath1,528 sq ft

65 Glenwood Ave, Stratford, CT 06614

Property at 70 Canaan Rd, Stratford, CT 06614, 5 beds, 2 baths

$479,900

5 beds2 baths1,570 sq ft

70 Canaan Rd, Stratford, CT 06614

Property at 21 Point Rd, Norwalk, CT 06854, 7 beds, 9.5 baths

$4,895,000

7 beds9.5 baths10,045 sq ft

21 Point Rd, Norwalk, CT 06854

Property at 1031 Lindley St, Bridgeport, CT 06606, 4 beds, 2 baths

$599,900

4 beds2 baths2,376 sq ft

1031 Lindley St, Bridgeport, CT 06606

Property at 35 Sherwood Pl, Southport, CT 06890, 4 beds, 2.5 baths

$1,149,000

4 beds2.5 baths1,892 sq ft

35 Sherwood Pl, Southport, CT 06890

Property at 18 Patch St, Danbury, CT 06810, 6 beds, 2 baths

$605,000

6 beds2 baths1,102 sq ft

18 Patch St, Danbury, CT 06810

Property at 810 North Ave, Bridgeport, CT 06606, 8 beds, 3 baths

$679,000

8 beds3 baths3,348 sq ft

810 North Ave, Bridgeport, CT 06606

Property at 31 Meadow Wood Dr, Greenwich, CT 06830, 3 beds, 3.5 baths

$6,995,000

3 beds3.5 baths2,425 sq ft

31 Meadow Wood Dr, Greenwich, CT 06830

Property at 215 Knickerbocker Ave, Stamford, CT 06907, 4 beds, 3.5 baths

$999,999

4 beds3.5 baths3,653 sq ft

215 Knickerbocker Ave, Stamford, CT 06907

Property at 335 N Bishop Ave #12, Bridgeport, CT 06610, 3 beds, 1 bath

$94,000

3 beds1 bath739 sq ft

335 N Bishop Ave #12, Bridgeport, CT 06610

Property at 49 Perth St, Bridgeport, CT 06606, 5 beds, 3 baths

$450,000

5 beds3 baths1,822 sq ft

49 Perth St, Bridgeport, CT 06606

Property at 517 Newfield Ave, Stamford, CT 06905, 4 beds, 2.5 baths

$1,095,000

4 beds2.5 baths2,217 sq ft

517 Newfield Ave, Stamford, CT 06905

Property at 638 Hope St #4, Stamford, CT 06907, 4 beds, 4.5 baths

$749,000

4 beds4.5 baths4,058 sq ft

638 Hope St #4, Stamford, CT 06907

Property at 163 Huntingtown Rd, Newtown, CT 06470, 2 beds, 1 bath

$350,000

2 beds1 bath960 sq ft

163 Huntingtown Rd, Newtown, CT 06470

Property at 224 Ramapoo Rd, Ridgefield, CT 06877, 2 beds, 2 baths

$699,000

2 beds2 baths1,413 sq ft

224 Ramapoo Rd, Ridgefield, CT 06877

Property at 46 Stonehedge Drive South, Greenwich, CT 06831, 3 beds, 3.5 baths

$3,650,000

3 beds3.5 baths3,200 sq ft

46 Stonehedge Drive South, Greenwich, CT 06831

Property at 36 Sunset New Fairfield, CT Trl, New Fairfield, NY 06812, 3 beds, 2.5 baths

$899,000

3 beds2.5 baths2,268 sq ft

36 Sunset New Fairfield, CT Trl, New Fairfield, NY 06812

Listing by Coldwell Banker Realty

Property at 141 Head Of Meadow Rd, Newtown, CT 06470, 3 beds, 2 baths

$699,000

3 beds2 baths2,376 sq ft

141 Head Of Meadow Rd, Newtown, CT 06470

Property at 41 Quince St, Bridgeport, CT 06606, 3 beds, 2 baths

$399,997

3 beds2 baths1,680 sq ft

41 Quince St, Bridgeport, CT 06606

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Based on information submitted to the MLS GRID as of Wed Oct 28 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 869 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 900 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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