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:
Opportunity awaits! This multifamily home is located minutes from E. Gaynor Brennan golf course, Stamford Hospital, the Boys & Girls Club, and more. Zoned as VC - Village Commercial - which supports small scale, commercial districts in residential neighborhoods. It is designed to allow a mix of a mix of retail, service, and residential uses while maintaining a traditional, village-style architectural character. Renovate for maximum rental potential or build new. Sold as is.

$999,000

5 beds2 baths2,803 sq ft

256 Stillwater Ave, Stamford, CT 06902

Multifamily home • Zoned vc • 0.25 acre lot

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Incredible location meets endless potential! Tucked away on a quiet cul-de-sac in a wonderful, established neighborhood, this single-level ranch features 4 bedrooms and 1.5 baths-offering convenient single-floor living with plenty of room for family or guests. Situated on a manageable level lot, the property is just minutes from Fairfield University, top local amenities, commuter routes, and schools. The interior is ready for your personal touch and cosmetic updates-bring your vision to transform this space into your dream home or investment property. Opportunities in this prime neighborhood don't last long-schedule your tour today! Property is being sold as-is, subject to probate approval.

$685,000

4 beds1.5 baths1,612 sq ft

17 Greenbriar Cir, Fairfield, CT 06824

Single-level ranch • Manageable level lot • Quiet cul-de-sac

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Huge rare find! This impressive 4,590 sq. ft. 3-family property offers incredible versatility with zoning that allows for residential, commercial, or mixed-use possibilities. The property features three separate units, a detached 5-car garage, and a spacious driveway with plenty of parking. The first-floor unit is currently set up as an insurance office and offers a living room, eat-in kitchen with laundry area, 3 bedrooms, and an updated full bath. The second-floor unit features a spacious living room, dining room, eat-in kitchen with laundry area, 3 bedrooms, an updated full bath, and an enclosed porch. The entire third floor has been completely gutted, with all electrical and plumbing in

$725,000

8 beds3 baths4,590 sq ft

1757 E Main St, Bridgeport, CT 06610

Updated full bath • Enclosed porch • Spacious driveway

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Oversized 4,488 sq ft brick 3-family home in Bridgeport's prime North End / St. Vincent's Hospital neighborhood! Featuring 8 total bedrooms across three spacious units (3BR / 3BR / 2BR), this property delivers unbeatable scale and utility. Key updates and highlights include natural gas heating, a 2019 roof, a 1st floor unit with a private concrete terrace off the living room, and an updated 2nd floor with dedicated solar panels. Complete with a large full basement offering endless possibilities, an expansive side yard, and a rare 3-car detached garage. Prime location close to medical centers, public transit, and major highways-a must-see for investors and owner-occupants alike!

$775,000

8 beds3 baths4,488 sq ft

260 Whitney Ave, Bridgeport, CT 06606

Expansive side yard • Prime location • Large full basement

COMING SOONFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Some places change the way you spend your time. Bloomsbury Ridge is one of them. Set high along scenic Long Ridge Road, this extraordinary 80-acre estate offers a rare world of privacy, beauty and possibility, yet remains remarkably connected to everything beyond its 80 acres. The magnificent country house was designed to be elegant without formality, with a soaring two-story library, richly detailed Great Room, five bedrooms, multiple fireplaces and spaces that invite both quiet weekends and unforgettable gatherings. Outside, the property becomes a world unto itself: swim in the secluded pool, play on the red clay tennis court, wander through fields and woods, tend the orchard and vegetabl

$12,500,000

5 beds6.5 baths9,140 sq ft

125 Long Ridge Rd, Danbury, CT 06810

Multiple fireplaces • Secluded pool • Two story library

Property at 471 Housatonic Ave, Stratford, CT 06615, 3 beds, 2 baths

$579,000

3 beds2 baths1,894 sq ft

471 Housatonic Ave, Stratford, CT 06615

Property at 76-78 Suburban Ave, Bridgeport, CT 06604, 4 beds, 2 baths

$595,000

4 beds2 baths1,918 sq ft

76-78 Suburban Ave, Bridgeport, CT 06604

Property at 1149 Warner Hill Rd, Stratford, CT 06614, 4 beds, 2 baths

$649,000

4 beds2 baths2,782 sq ft

1149 Warner Hill Rd, Stratford, CT 06614

Property at 240 Sheridan St, Bridgeport, CT 06610, 6 beds, 3 baths

$549,500

6 beds3 baths2,940 sq ft

240 Sheridan St, Bridgeport, CT 06610

Property at 70 Benedict Ave, Fairfield, CT 06825, 2 beds, 2 baths

$648,000

2 beds2 baths1,280 sq ft

70 Benedict Ave, Fairfield, CT 06825

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

Property at 164 Virginia Ave Unit B, Bridgeport, CT 06610, 1 bed, 1 bath

$129,900

1 bed1 bath650 sq ft

164 Virginia Ave Unit B, Bridgeport, CT 06610

Property at 40 Kellogg St, Brookfield, CT 06804, 5 beds, 2 baths

$885,000

5 beds2 baths2,130 sq ft

40 Kellogg St, Brookfield, CT 06804

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 57-59 West St, Danbury, CT 06810, 9 beds, 6 baths

$1,399,000

9 beds6 baths5,338 sq ft

57-59 West St, Danbury, CT 06810

Property at 51 Brown Ave, Stamford, CT 06902, 9 beds, 4 baths

$1,500,000

9 beds4 baths3,342 sq ft

51 Brown Ave, Stamford, CT 06902

Property at 161-163 Harriet St, Bridgeport, CT 06608, 6 beds, 3 baths

$549,000

6 beds3 baths2,957 sq ft

161-163 Harriet St, Bridgeport, CT 06608

$449,999

3 beds1.5 baths2,054 sq ft

60 Boston Ter, Bridgeport, CT 06610

Property at 327 Jelliff Mill Rd, New Canaan, CT 06840, 5 beds, 5 baths

$2,000,000

5 beds5 baths3,383 sq ft

327 Jelliff Mill Rd, New Canaan, CT 06840

Property at 58 Sheephill Rd, Riverside, CT 06878, 4 beds, 4 baths

$1,850,000

4 beds4 baths2,899 sq ft

58 Sheephill Rd, Riverside, CT 06878

Property at 17 Driftwood Ln, Norwalk, CT 06851, 4 beds, 2 baths

$949,000

4 beds2 baths3,502 sq ft

17 Driftwood Ln, Norwalk, CT 06851

Property at 10 Mill Pond Ct, Cos Cob, CT 06807, 3 beds, 2 baths

$1,850,000

3 beds2 baths1,739 sq ft

10 Mill Pond Ct, Cos Cob, CT 06807

Property at 27 Rayfield Rd, Westport, CT 06880, 3 beds, 4 baths

$1,800,000

3 beds4 baths3,104 sq ft

27 Rayfield Rd, Westport, CT 06880

Property at 121 Parry Rd, Stamford, CT 06907, 5 beds, 3.5 baths

$1,450,000

5 beds3.5 baths4,177 sq ft

121 Parry Rd, Stamford, CT 06907

Property at 15 Brooklawn Ave, Stamford, CT 06906, 3 beds, 1.5 baths

$749,000

3 beds1.5 baths1,958 sq ft

15 Brooklawn Ave, Stamford, CT 06906

Property at 2493 Redding Rd, Fairfield, CT 06824, 5 beds, 5 baths

$2,395,000

5 beds5 baths5,415 sq ft

2493 Redding Rd, Fairfield, CT 06824

Property at 105 Glenville St, Greenwich, CT 06831, 3 beds, 2.5 baths

$1,449,000

3 beds2.5 baths1,713 sq ft

105 Glenville St, Greenwich, CT 06831

Property at 207 Redding Rd, Redding, CT 06896, 4 beds, 2 baths

$1,099,000

4 beds2 baths3,124 sq ft

207 Redding Rd, Redding, CT 06896

Property at 49 Old Middle Rd, Brookfield, CT 06804, 4 beds, 2 baths

$539,900

4 beds2 baths1,905 sq ft

49 Old Middle Rd, Brookfield, CT 06804

Property at 11 Oldfield Dr, Fairfield, CT 06824, 4 beds, 2 baths

$1,195,000

4 beds2 baths2,124 sq ft

11 Oldfield Dr, Fairfield, CT 06824

Property at 128 Linley Dr, Fairfield, CT 06825, 3 beds, 3 baths

$1,195,000

3 beds3 baths2,169 sq ft

128 Linley Dr, Fairfield, CT 06825

Property at 143 Chestnut Hill Rd, Wilton, CT 06897, 6 beds, 5.5 baths

$2,375,000

6 beds5.5 baths5,455 sq ft

143 Chestnut Hill Rd, Wilton, CT 06897

Property at 13 Chestnut St, Darien, CT 06820, 4 beds, 3 baths

$1,895,000

4 beds3 baths2,303 sq ft

13 Chestnut St, Darien, CT 06820

Property at 4438 Madison Ave, Trumbull, CT 06611, 3 beds, 3 baths

$599,900

3 beds3 baths2,184 sq ft

4438 Madison Ave, Trumbull, CT 06611

Property at 14 Partrick Ln, Wilton, CT 06897, 3 beds, 3 baths

$899,000

3 beds3 baths2,610 sq ft

14 Partrick Ln, Wilton, CT 06897

Property at 38 Carlisle Pl, Stamford, CT 06902, 3 beds, 2 baths

$739,000

3 beds2 baths1,600 sq ft

38 Carlisle Pl, Stamford, CT 06902

Property at 83 Pepper St, Monroe, CT 06468, 3 beds, 2.5 baths

$649,900

3 beds2.5 baths2,308 sq ft

83 Pepper St, Monroe, CT 06468

Property at 8 Somerset Ln, Riverside, CT 06878, 6 beds, 6.5 baths

$5,295,000

6 beds6.5 baths5,278 sq ft

8 Somerset Ln, Riverside, CT 06878

Property at 150 Route 39 S, Sherman, CT 06784, 2 beds, 1 bath

$399,000

2 beds1 bath1,171 sq ft

150 Route 39 S, Sherman, CT 06784

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 12 Sherman Ave #2, Greenwich, CT 06831, 2 beds, 2.5 baths

$895,000

2 beds2.5 baths1,695 sq ft

12 Sherman Ave #2, Greenwich, CT 06831

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Based on information submitted to the MLS GRID as of Mon Oct 05 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 830 vintage homes for sale in Fairfield County at a median listing price of $689K. 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 51 days and receive 4 offers. This map is refreshed with the newest listings in Fairfield County every 15 minutes.

In the past month, 939 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 883 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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