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:
716 Cheese Spring Road in New Canaan was built completely new in 2019 and customized by the current owners even further. This turn-key home with five bedrooms, five and a half baths and 5,135 square feet sits on 2.84 acres in the northeast side of town. The kitchen was renovated with an Italian stone island, upgraded Sub-Zero, Wolf and Miele appliances. A built-in coffee bar, patio access and spacious dining area complete the kitchen area. A cozy fireplace anchors the oversized and sun drenched living room. Downstairs, a den and bedroom double as a pool house with a full bath and shower. The luxurious primary suite offers a bedroom with a fireplace, built-ins, two walk-in closets, generous

$3,600,000

5 beds5.5 baths5,135 sq ft

716 Cheese Spring Rd, New Canaan, CT 06840

In-ground pool • Built-in coffee bar • Two fire pits

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
An elegant Regency-style residence with dramatic architectural presence is positioned in a premier location just moments from the village. Inside, ten-foot ceilings and Palladian windows flood the home with natural light. From the barrel-vaulted living room-a true Grand Salon-to the striking onyx-floored dining room, the interior spaces flow effortlessly to an expansive terrace, creating an unforgettable setting for both grand entertaining and quiet family relaxation. Offering a rare opportunity for luxurious, SINGLE-LEVEL living, the home seamlessly pairs grand scale with absolute privacy. The thoughtfully designed floor plan features a chef's kitchen, a sun-drenched breakfast room, a recr

$3,300,000

3 beds3.5 baths3,040 sq ft

321 Oenoke Rdg, New Canaan, CT 06840

Palladian windows • Grand salon • Ten foot ceilings

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Set on a spectacular level acre at the end of a peaceful Lower Easton cul de sac, this beautifully maintained three bedroom ranch offers an exceptional combination of privacy, space and effortless one level living. The inviting living room features gleaming hardwood floors and a wood burning fireplace, flowing seamlessly into the renovated eat-in kitchen with white shaker cabinetry, quartz countertops and stainless steel appliances. An adjoining enclosed sun porch opens to the rear deck and expansive backyard, creating a wonderful setting for entertaining, relaxing and enjoying the surrounding grounds. The primary bedroom features hardwood floors and a private en-suite bath, while two addit

$649,000

3 beds2 baths1,270 sq ft

29 Mohawk Dr, Easton, CT 06612

Quartz countertops • One level living • Enclosed sun porch

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
A charming 3 bedroom Cape Cod-style vintage home. The large remodeled eat-in-kitchen is the hub of the home. The living room has a beautiful stone faced fireplace and golden oak floors. There is a cozy enclosed porch at the front of the home. The dining room has built-in shelving and parquet flooring. There is a first floor bedroom and full bath on the main floor. Upstairs there are two more bedrooms. There is a full basement for storage, with a Bilko door to the yard. There is a two-car detached garage. The beautiful, flat quarter-acre yard is fenced in for privacy or playtime for your pets. The location is advantageous to a commuter being walking distance to the Glenbrook Metro North Trai

$625,000

3 beds1 bath1,353 sq ft

307 Courtland Ave, Stamford, CT 06906

Bilko door • Full basement • Built-in shelving

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 10 Hillwood Place, a charming 1928 Colonial in the desirable Silvermine neighborhood, offering 2,150 square feet of light-filled living space on a quiet 0.23-acre lot. Blending timeless character with modern convenience, this home features 4 bedrooms and 2.5 baths. The main level is designed for effortless living and entertaining, anchored by a convenient layout connecting the living room, dining room, and kitchen. A sunny breakfast room and a spacious family room both offer direct access to the rear deck, creating an easy indoor-outdoor flow. The main floor also hosts a private primary suite complete with multiple closets and a large primary bathroom with a whirlpool tub--perfec

$699,000

4 beds2.5 baths2,150 sq ft

10 Hillwood Pl, Norwalk, CT 06850

Charming porch • Whirlpool tub • Wonderful deck

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 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 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 29 Weatherbell Dr, Norwalk, CT 06851, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths2,044 sq ft

29 Weatherbell Dr, Norwalk, CT 06851

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 91 Ward St, Norwalk, CT 06851, 4 beds, 2 baths

$635,000

4 beds2 baths1,322 sq ft

91 Ward St, Norwalk, CT 06851

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 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 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 557 Wilmot Ave #6, Bridgeport, CT 06607, 2 beds, 1 bath

$48,000

2 beds1 bath750 sq ft

557 Wilmot Ave #6, Bridgeport, CT 06607

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 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 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 211 Old Farm Rd, Fairfield, CT 06825, 4 beds, 2.5 baths

$1,050,000

4 beds2.5 baths3,013 sq ft

211 Old Farm Rd, Fairfield, CT 06825

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 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 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 170 S Main St, Newtown, CT 06470, 2 beds, 1 bath

$450,000

2 beds1 bath800 sq ft

170 S Main St, Newtown, CT 06470

Property at 41 Burritt Ave, Stratford, CT 06615, 4 beds, 1.5 baths

$589,900

4 beds1.5 baths1,981 sq ft

41 Burritt Ave, Stratford, CT 06615

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 144 Colonial Rd, Stamford, CT 06906, 4 beds, 2 baths

$904,999

4 beds2 baths2,880 sq ft

144 Colonial Rd, Stamford, CT 06906

Property at 39 Crane Rd, Stamford, CT 06902, 3 beds, 2 baths

$829,000

3 beds2 baths2,063 sq ft

39 Crane Rd, Stamford, CT 06902

Property at 33 Bridge St, Westport, CT 06880, 2 beds, 1.5 baths

$1,999,999

2 beds1.5 baths1,206 sq ft

33 Bridge St, Westport, CT 06880

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 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 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 127 Jennings Rd, Fairfield, CT 06825, 5 beds, 2 baths

$750,000

5 beds2 baths2,400 sq ft

127 Jennings Rd, Fairfield, CT 06825

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 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 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 142 Cambridge St, Stratford, CT 06614, 3 beds, 1.5 baths

$475,000

3 beds1.5 baths1,752 sq ft

142 Cambridge St, Stratford, CT 06614

Property at 47 Second St, Norwalk, CT 06855, 4 beds, 2 baths

$849,000

4 beds2 baths2,472 sq ft

47 Second St, Norwalk, CT 06855

Property at 18 Southgate Rd, Trumbull, CT 06611, 3 beds, 1 bath

$500,000

3 beds1 bath960 sq ft

18 Southgate Rd, Trumbull, CT 06611

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 109 Woolsley Ave, Trumbull, CT 06611, 3 beds, 1 bath

$485,000

3 beds1 bath1,344 sq ft

109 Woolsley Ave, Trumbull, CT 06611

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Based on information submitted to the MLS GRID as of Wed Oct 21 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 865 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, 753 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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