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

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FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
* New Roof about to be installed. * Brand New hard wood floor in 30ft primary bedroom. Timeless character meets contemporary comfort in this beautiful antique multi-generational home with attached apartment. Major extensions in 1990, and further upgrades in 2015 and 2020. The main house offers three bedrooms and 3-and-a-half baths. The residence blends historic charm with thoughtful modern upgrades. The inviting family room opens directly onto the deck, creating an effortless connection between indoor and outdoor living. The primary bedroom features large dressing room. The second-floor recreation room opens to a private balcony overlooking the beautifully landscaped gardens. Outside, an ab

$719,900

4 beds3.5 baths3,618 sq ft

66 Taylor Rd, Bethel, CT 06801

Updated antique home • Private balcony • Natural pond

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Spacious 3 Bedroom Condo with the Privacy of a Single Family Home. Welcome to this spacious and inviting 3 bedroom, 2nd-floor condo offering privacy, space, and low maintenance living. With its own private entrance and individual address, only two units sharing the property, and no monthly HOA fee. This home offers many of the benefits of a single-family home without the typical monthly association costs. Step inside to a bright, open floor plan featuring a spacious living room with soaring ceilings. The seamless flow between the living, dining and kitchen areas makes everyday living and entertaining easy. The kitchen offers convenient workspace and storage while remaining connected to the

$369,000

3 beds1 bath1,280 sq ft

1035 Black Rock Tpke #1035, Fairfield, CT 06825

Separate entrance • No monthly hoa • Vaulted ceiling

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Charm Of A Cape With A Unique Layout That Lives Like A Split-Level. The inviting floor plan features a step-down living room and dining room, creating distinct spaces for entertaining and everyday living. Offering three bedrooms and three full baths, the spacious primary suite includes two walk-in closets and a private full bath. Additional highlights include a first-floor family room, some hardwood flooring, two fireplaces, central air conditioning, and a propane generator for added peace of mind. The finished lower level provides flexible space for a recreation room, home office, gym, or guest area. Situated on a beautiful, approximately half-acre lot on a private road, this property offe

$1,595,000

3 beds3 baths2,432 sq ft

21 Hampton Ln, New Canaan, CT 06840

Recreation room • Propane generator • Two fireplaces

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
NEW PRICE - REDUCED $50,000! 5BR/3BA Home in Trumbull Near the Merritt Parkway Now $649,999! Space, character, and opportunity at a newly reduced price. This spacious 5-bedroom, 3-full-bath home offers a flexible layout with two bedrooms on the main level and three upstairs. Hardwood floors, charming arched doorways, and two cozy fireplaces add warmth and character, while a bright sunroom overlooks a backyard with plenty of possibilities for gardens, flowers, and outdoor enjoyment. A partially finished basement offers flexible space for a home office, recreation room, or gym, while the two-car garage provides additional storage and convenience. The Merritt Parkway is just minutes away. Full

$649,999

5 beds3 baths3,864 sq ft

124 Chestnut Hill Rd, Trumbull, CT 06611

Sunroom • Cozy fireplace • Two car garage

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to an incredible opportunity in the highly desirable town of Weston! Set back from Newtown Turnpike on a secluded, level 1.33 acre lot, this exceptionally well maintained 3 bedroom, 2 full bath ranch offers 1,332 square feet of comfortable single level living with hardwood floors throughout and a detached two car garage. Ideally located near the Saugatuck Reservoir, Merritt Parkway, and Devil's Den Nature Preserve, the property is ready for its next owner's vision. Thoughtful updates could transform the existing home into a beautiful retreat, while the generous lot may offer exciting possibilities for expansion, including a potential second story addition or new construction, subjec

$564,900

3 beds2 baths1,332 sq ft

261 Newtown Tpke, Weston, CT 06883

Generous lot • Near merritt parkway • Secluded level lot

Property at 205 Mountain Rd, Wilton, CT 06897, 2 beds, 1 bath

$479,900

2 beds1 bath892 sq ft

205 Mountain Rd, Wilton, CT 06897

Property at 85 Walnut St, Monroe, CT 06468, 3 beds, 2 baths

$585,000

3 beds2 baths1,376 sq ft

85 Walnut St, Monroe, CT 06468

Property at 21 Calhoun Dr, Greenwich, CT 06831, 5 beds, 7 baths

$6,150,000

5 beds7 baths6,143 sq ft

21 Calhoun Dr, Greenwich, CT 06831

Property at 45 Glen Avon Dr, Riverside, CT 06878, 4 beds, 3.5 baths

$8,600,000

4 beds3.5 baths2,783 sq ft

45 Glen Avon Dr, Riverside, CT 06878

Property at 68 Parry Rd, Stamford, CT 06907, 3 beds, 2.5 baths

$1,350,000

3 beds2.5 baths2,790 sq ft

68 Parry Rd, Stamford, CT 06907

Property at 216 Cross Hill Rd, Monroe, CT 06468, 2 beds, 1 bath

$336,000

2 beds1 bath932 sq ft

216 Cross Hill Rd, Monroe, CT 06468

Property at 178 Church St, Monroe, CT 06468, 3 beds, 1 bath

$525,000

3 beds1 bath1,472 sq ft

178 Church St, Monroe, CT 06468

Property at 40 Stonehouse Rd, Trumbull, CT 06611, 4 beds, 2 baths

$639,900

4 beds2 baths2,048 sq ft

40 Stonehouse Rd, Trumbull, CT 06611

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 326 Soundview Ave, Bridgeport, CT 06606, 4 beds, 2 baths

$449,000

4 beds2 baths1,715 sq ft

326 Soundview Ave, Bridgeport, CT 06606

Property at 136 Alton Rd, Stamford, CT 06906, 3 beds, 2.5 baths

$875,000

3 beds2.5 baths1,992 sq ft

136 Alton Rd, Stamford, CT 06906

Property at 64 Forest Dr, Sandy Hook, CT 06482, 2 beds, 1 bath

$275,000

2 beds1 bath544 sq ft

64 Forest Dr, Sandy Hook, CT 06482

Property at 89 Chestnut Hill Rd, Wilton, CT 06897, 6 beds, 5 baths

$2,395,000

6 beds5 baths5,576 sq ft

89 Chestnut Hill Rd, Wilton, CT 06897

Property at 438 High St, Fairfield, CT 06824, 4 beds, 2 baths

$575,000

4 beds2 baths1,142 sq ft

438 High St, Fairfield, CT 06824

Property at 264 Taconic Rd, Greenwich, CT 06831, 5 beds, 5.5 baths

$5,200,000

5 beds5.5 baths4,190 sq ft

264 Taconic Rd, Greenwich, CT 06831

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

$2,975,000

3 beds3.5 baths3,040 sq ft

321 Oenoke Rdg, New Canaan, CT 06840

Property at 1 Deepwoods Ln, Old Greenwich, CT 06870, 5 beds, 4 baths

$3,695,000

5 beds4 baths4,488 sq ft

1 Deepwoods Ln, Old Greenwich, CT 06870

Berkshire Hathaway HS NE Prop.

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

$384,000

2 beds1 bath1,171 sq ft

150 Route 39 S, Sherman, CT 06784

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 10 Horseshoe Dr, Danbury, CT 06811, 3 beds, 1.5 baths

$489,000

3 beds1.5 baths1,770 sq ft

10 Horseshoe Dr, Danbury, CT 06811

Property at 26 Campbell Dr, Stamford, CT 06903, 4 beds, 3 baths

$899,900

4 beds3 baths2,315 sq ft

26 Campbell Dr, Stamford, CT 06903

Property at 2082 Stratfield Rd, Fairfield, CT 06825, 4 beds, 1.5 baths

$525,000

4 beds1.5 baths1,082 sq ft

2082 Stratfield Rd, Fairfield, CT 06825

Property at 9 Seaside Pl, Norwalk, CT 06855, 5 beds, 2 baths

$1,895,000

5 beds2 baths2,809 sq ft

9 Seaside Pl, Norwalk, CT 06855

Property at 11 Birdseye Rd Ext, Shelton, CT 06484, 3 beds, 2.5 baths

$659,900

3 beds2.5 baths2,354 sq ft

11 Birdseye Rd Ext, Shelton, CT 06484

Property at 70 N Taylor Ave, Norwalk, CT 06854, 3 beds, 2 baths

$639,900

3 beds2 baths1,945 sq ft

70 N Taylor Ave, Norwalk, CT 06854

Property at 16 Grace St, New Canaan, CT 06840, 5 beds, 4.5 baths

$2,895,000

5 beds4.5 baths2,778 sq ft

16 Grace St, New Canaan, CT 06840

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 31 Splitrock Rd, Norwalk, CT 06854, 4 beds, 4 baths

$1,800,000

4 beds4 baths3,392 sq ft

31 Splitrock Rd, Norwalk, CT 06854

Property at 311 Mountain Rd, Wilton, CT 06897, 4 beds, 3 baths

$945,000

4 beds3 baths3,300 sq ft

311 Mountain Rd, Wilton, CT 06897

Property at 21 Byram Rd, Greenwich, CT 06830, 3 beds, 2.5 baths

$899,000

3 beds2.5 baths1,664 sq ft

21 Byram Rd, Greenwich, CT 06830

Property at 415 Old Post Rd, Fairfield, CT 06824, 5 beds, 4.5 baths

$3,975,000

5 beds4.5 baths5,740 sq ft

415 Old Post Rd, Fairfield, CT 06824

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

$635,000

4 beds2 baths1,322 sq ft

91 Ward St, Norwalk, CT 06851

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Based on information submitted to the MLS GRID as of Wed Nov 11 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 813 vintage homes for sale in Fairfield County at a median listing price of $690K. 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 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 902 condos, 2 townhouses, and 242 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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