Vintage homes for sale & real estate in Fairfield County, CT

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OPEN OCT 19, 1PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Tucked among some of Black Rock's most beautiful homes-and just steps from the Black Rock Yacht Club and St. Mary's by the Sea-37 Thorne Place is a grand and utterly unique residence set on a spectacular double lot. With its distinctive Tudor-inspired architecture, sweeping grounds, multiple porches, soaring ceilings, gorgeous gardens & exceptional scale, this is a home with presence- and personality. Inside, original character meets a wonderfully playful aesthetic, with rich color, pattern, beautiful millwork, arched doorways, handsome fireplaces & walls of windows at every turn. A spectacular green sunroom wrapped in windows overlooks the gardens, while gracious living &

$2,499,000

5 beds5 baths4,329 sq ft

37 Thorne Pl, Bridgeport, CT 06605

0.42 acre lot • 2 garage spots • Built 1918

OPEN SUN, 1PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Set on a tranquil street in a convenient Fairfield location, this Colonial offers a versatile floor plan with plenty of room to live, relax, and entertain. Situated on a level quarter acre property within walking distance of the elementary school, the home features generous indoor and outdoor living spaces, freshly painted interiors, and beautifully refinished hardwood floors. The inviting living room features a classic brick fireplace framed by rich mahogany trim, adding warmth and character. At the back of the home, a sun drenched family room welcomes an abundance of natural light, with sliding doors opening to a wraparound deck overlooking the expansive, level backyard. The main level al

$865,000

4 beds2 baths2,292 sq ft

38 Milandale Rd, Fairfield, CT 06824

0.24 acre lot • 2 garage spots • Built 1958

OPEN SUN, 12PM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
11 Oldfield Drive offers the rare combination of neighborhood charm, a turnkey home, and an exceptional in-town location. Set on a quiet cul-de-sac, this classic Cape features approximately 2,000 square feet of finished living space with four true bedrooms, two full baths, and a finished lower level offering valuable flexibility for a home office, playroom, gym, or additional living space. The bright white kitchen is equipped with Viking appliances and opens to the inviting living room, anchored by a wood-burning fireplace. Outside, the fenced yard is designed for easy everyday living and entertaining, with a dining patio, mature arborvitaes providing privacy, and a classic white picket fen

$1,195,000

4 beds2 baths2,124 sq ft

11 Oldfield Dr, Fairfield, CT 06824

Dining patio • Viking appliances • Bright white kitchen

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 95 Orange Street. A beautiful, clean, spacious sunlit Colonial home tucked away in the Eastern part of the City; having a versatile floor plan with 4 levels of living space. Newer roof (solar), updated windows, 3/4 fenced grassy yard, detached 1 car garage with power & partially covered & open deck & vinyl siding complete the exterior. The entry foyer has a large closet; there are beautiful hardwood floors, large eat-in kitchen w/ stone counters & S/S appliances. Living room with brick fireplace, formal dining room with an attached den/office/bedroom. Upstairs there are 3 bedrooms, walk-in closet, full bath & finished attic with huge closet - could b

$675,000

4 beds2.5 baths1,729 sq ft

95 Orange St, Stamford, CT 06902

Newer roof • Updated windows • Sunlit colonial home

OPEN SUN, 2AM TO 4PM

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 38 Carlisle Place, a charming 3-bedroom, 2-bath Cape offering an inviting blend of character, updates and versatility. Inside, enjoy hardwood floors, a beautifully updated eat-in kitchen with quartz countertops, a bright sunroom with French doors, and a full bath on each level. The expansive upper-level primary bedroom offers exciting potential for a future 4-bedroom layout. Outside, a newly improved backyard and beautiful new stonework create the perfect setting for entertaining and outdoor living. Additional highlights include a newer roof and boiler, attached garage, private driveway, and a large unfinished basement offering exceptional storage and future possibilities. Conven

$739,000

3 beds2 baths1,600 sq ft

38 Carlisle Pl, Stamford, CT 06902

New stonework • Newer roof • Bright sunroom

Property at 21 East Ave, Norwalk, CT 06851, 3 beds, 1 bath

$525,000

3 beds1 bath1,530 sq ft

21 East Ave, Norwalk, CT 06851

Property at 135 Stuart Ave, Norwalk, CT 06851, 3 beds, 1.5 baths

$550,000

3 beds1.5 baths1,188 sq ft

135 Stuart Ave, Norwalk, CT 06851

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 20 Glen Arden Dr S, Fairfield, CT 06824, 3 beds, 3 baths

$899,000

3 beds3 baths2,940 sq ft

20 Glen Arden Dr S, Fairfield, CT 06824

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 21 Hill St, Norwalk, CT 06850, 4 beds, 2 baths

$599,000

4 beds2 baths1,204 sq ft

21 Hill St, Norwalk, CT 06850

Property at 14 Moody Ln, Danbury, CT 06811, 3 beds, 2.5 baths

$550,000

3 beds2.5 baths1,666 sq ft

14 Moody Ln, Danbury, CT 06811

Property at 116 Mulberry St, Stamford, CT 06907, 4 beds, 3 baths

$739,000

4 beds3 baths2,360 sq ft

116 Mulberry St, Stamford, CT 06907

Property at 73 Macarthur Dr, Stratford, CT 06614, 3 beds, 2.5 baths

$369,000

3 beds2.5 baths1,735 sq ft

73 Macarthur Dr, Stratford, CT 06614

Property at 107 Maple Ave, Greenwich, CT 06830, 5 beds, 7.5 baths

$8,800,000

5 beds7.5 baths6,637 sq ft

107 Maple Ave, Greenwich, CT 06830

Property at 32 Depalma Ln, Danbury, CT 06811, 2 beds, 1 bath

$285,000

2 beds1 bath1,036 sq ft

32 Depalma Ln, Danbury, CT 06811

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 96 Van St, Stratford, CT 06614, 4 beds, 2 baths

$435,000

4 beds2 baths1,384 sq ft

96 Van St, Stratford, CT 06614

Property at 60 Nashvile Rd, Bethel, CT 06801, 3 beds, 1.5 baths

$699,000

3 beds1.5 baths1,766 sq ft

60 Nashvile Rd, Bethel, CT 06801

Property at 336 Barnum Ter Ext, Stratford, CT 06614, 3 beds, 1.5 baths

$315,000

3 beds1.5 baths989 sq ft

336 Barnum Ter Ext, Stratford, CT 06614

Property at 61 Putnam Park #61, Greenwich, CT 06830, 3 beds, 2 baths

$700,000

3 beds2 baths1,250 sq ft

61 Putnam Park #61, Greenwich, CT 06830

Property at 72 Chestnut St, Bethel, CT 06801, 4 beds, 1.5 baths

$359,000

4 beds1.5 baths1,482 sq ft

72 Chestnut St, Bethel, CT 06801

Property at 59 Creeping Hemlock Dr, Norwalk, CT 06851, 4 beds, 3 baths

$899,900

4 beds3 baths2,346 sq ft

59 Creeping Hemlock Dr, Norwalk, CT 06851

Property at 14 Park Ln, Norwalk, CT 06851, 3 beds, 2.5 baths

$1,425,000

3 beds2.5 baths1,616 sq ft

14 Park Ln, Norwalk, CT 06851

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 4 Tremont St, Greenwich, CT 06807, 4 beds, 3 baths

$1,495,000

4 beds3 baths2,243 sq ft

4 Tremont St, Greenwich, CT 06807

Mike Parelli Real Estate LLC

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 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 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 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 97 Gorham Rd, Fairfield, CT 06824, 4 beds, 2 baths

$1,049,000

4 beds2 baths1,697 sq ft

97 Gorham Rd, 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 576 Huntington St, Shelton, CT 06484, 5 beds, 2 baths

$775,000

5 beds2 baths2,506 sq ft

576 Huntington St, Shelton, CT 06484

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 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 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 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 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 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 33 Circle Dr, Stratford, CT 06614, 1 bed, 1 bath

$350,000

1 bed1 bath588 sq ft

33 Circle Dr, Stratford, CT 06614

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

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Based on information submitted to the MLS GRID as of Sat Oct 17 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 867 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, 750 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 894 condos, 1 townhouse, and 216 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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