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

886 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
There are homes you visit, and there are homes you never want to leave. Rich in character & thoughtfully reimagined, this classic residence is the latter. A rare blend of timeless architecture, designer-appointed details, & easy living just minutes from the train, schools and vibrant Greenwich Avenue. The first floor features a gracious dining room that frames the backyard through an oversized picture window, while a warm and inviting family room, accented by exposed beams and a wall of sliding glass doors, creates a seamless connection to the outdoors. At the heart of it all is a carefully curated chef's kitchen, including a sun-washed banquette wrapped in windows; the perfect s

$5,745,000

6 beds7.5 baths6,878 sq ft

580 Lake Ave, Greenwich, CT 06830

Sliding glass doors • Bonus sunroom • Exposed beams

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Price Reduction! Welcome to this beautifully updated Cape Cod home located in a quiet South Ridgefield neighborhood, offering the perfect blend of classic charm and modern upgrades. The heart of the home is the stunning newly designed chef's kitchen featuring all new GE Cafe appliances, including a refrigerator, 6-burner gas range with griddle and 1.5 ovens, French door convection oven, dishwasher, and a microwave that also converts to a second oven. The spacious living room showcases hardwood floors and a wood-burning fireplace, while French doors open to a versatile family room or home office. The kitchen leads directly to the deck, creating the perfect space for indoor and outdoor entert

$875,000

4 beds3 baths3,028 sq ft

24 White Birch Rd, Ridgefield, CT 06877

Private walkout deck • Ge cafe appliances • 1.02 acre lot

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
LEGAL 3 FAMILY HOME STEPS TO BRIDGEPORT HOSPITAL AND STEELPOINTE DEVELOPMENT ON STRATFORD LINE, ALL MINUTES TO SCHOOLS, RETAIL/SHOPPING, RESTAURANTS, BEARDSLEY PARK, PARKS/REC, BUSLINE, METRO NORTH TRAIN STATION WITH EASY ACCESS TO I-95, RT 25/8 AND RT 15 MERRITT PARKWAY. TENANTS RESPONSIBLE FOR HEAT, HOT WATER AND ELECTRICITY WITH A PRIVATE, FENCED YARD AND A FULL LOWER LEVEL FOR LAUNDRY AND STORAGE. ADD TO YOUR INVESTMENT PORTFOLIO, SIT BACK AND COUNT YOUR RETURNS.

$549,500

6 beds3 baths2,940 sq ft

240 Sheridan St, Bridgeport, CT 06610

Easy access to i-95 • Private fenced yard • 3,920 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
NEW PRICE - NOW OFFERED AT $550,000! A wonderful opportunity to own a spacious and thoughtfully updated home in a desirable Stratford location-now with an exceptional new price! This inviting 4-bedroom, 2.5-bath home offers approximately 2,826 square feet of living space, a flexible layout, and features designed for comfortable everyday living for all family members. The first-floor primary suite, updated kitchen, newer windows, solar panels, mini-split cooling, and attached 3-car tandem garage are just some of the highlights. Step outside to enjoy a private, beautifully landscaped yard complete with gazebo and shed-an ideal setting for relaxing, entertaining, or enjoying the outdoors. Con

$550,000

4 beds2.5 baths2,826 sq ft

161 Delaware Dr, Stratford, CT 06614

Charming gazebo • Private oasis • Updated kitchen

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
A Frazier Peters masterpiece awaits its next steward on a private two-acre sanctuary in New Canaan. Enchanting stone steps lead the way to this magical home, where a great room with a soaring cathedral ceiling and large wood burning fireplace anchors the residence - flanked on one side by effortless entertaining spaces including a gourmet kitchen, formal dining room, and wet bar, as well as the private primary suite, and on the other by three additional bedrooms, a dedicated office, and two full baths. A sunroom bathes the home in natural light, offering a serene retreat to take in the lush, private grounds. Full of timeless character, architectural provenance, and enduring construction qua

$1,999,000

4 beds3 baths4,183 sq ft

Gravel Island Rd, New Canaan, CT 06840

Formal dining room • Wet bar • Gourmet kitchen

Property at 195 Webb Cir, Monroe, CT 06468, 4 beds, 2.5 baths

$949,000

4 beds2.5 baths3,074 sq ft

195 Webb Cir, Monroe, CT 06468

Property at 64 Main St, Newtown, CT 06470, 4 beds, 2.5 baths

$999,900

4 beds2.5 baths2,929 sq ft

64 Main St, Newtown, CT 06470

Property at 15 Shorelands Pl, Old Greenwich, CT 06870, 4 beds, 3.5 baths

$3,795,000

4 beds3.5 baths3,271 sq ft

15 Shorelands Pl, Old Greenwich, CT 06870

Property at 155 Long Neck Point Rd, Darien, CT 06820, 10 beds, 10.5 baths

$16,495,000

10 beds10.5 baths11,944 sq ft

155 Long Neck Point Rd, Darien, CT 06820

Property at 326 North St, Ridgefield, CT 06877, 3 beds, 1.5 baths

$1,150,000

3 beds1.5 baths1,496 sq ft

326 North St, Ridgefield, CT 06877

Property at 213 Knapps Hwy, Fairfield, CT 06825, 4 beds, 2 baths

$555,000

4 beds2 baths1,075 sq ft

213 Knapps Hwy, Fairfield, CT 06825

Property at 375 Rockwell Ave, Stratford, CT 06615, 4 beds, 2 baths

$395,000

4 beds2 baths1,939 sq ft

375 Rockwell Ave, Stratford, CT 06615

Property at 705 Weed St #2, New Canaan, CT 06840, 3 beds, 2.5 baths

$1,565,900

3 beds2.5 baths2,090 sq ft

705 Weed St #2, New Canaan, CT 06840

Property at 845 Kings Hwy W, Fairfield, CT 06825, 3 beds, 2.5 baths

$1,645,000

3 beds2.5 baths2,074 sq ft

845 Kings Hwy W, Fairfield, CT 06825

Property at 45 Cameo Ct, Stratford, CT 06614, 4 beds, 2 baths

$515,000

4 beds2 baths2,140 sq ft

45 Cameo Ct, Stratford, CT 06614

Property at 700 Hollow Tree Ridge Rd, Darien, CT 06820, 5 beds, 5.5 baths

$3,699,500

5 beds5.5 baths5,500 sq ft

700 Hollow Tree Ridge Rd, Darien, CT 06820

Property at 30 Birchwood Rd, Monroe, CT 06468, 3 beds, 1 bath

$440,000

3 beds1 bath1,488 sq ft

30 Birchwood Rd, Monroe, CT 06468

Property at 1908 Stratfield Rd, Fairfield, CT 06825, 7 beds, 3 baths

$875,000

7 beds3 baths4,862 sq ft

1908 Stratfield Rd, Fairfield, CT 06825

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 6 Brinsmade Ln, Sherman, CT 06784, 5 beds, 4 baths

$1,099,000

5 beds4 baths4,200 sq ft

6 Brinsmade Ln, Sherman, CT 06784

Property at 8 Rising Rd, Norwalk, CT 06850, 6 beds, 4 baths

$1,349,000

6 beds4 baths3,860 sq ft

8 Rising Rd, Norwalk, CT 06850

Property at 76 Newton St, Stratford, CT 06614, 3 beds, 1.5 baths

$459,900

3 beds1.5 baths1,569 sq ft

76 Newton St, Stratford, CT 06614

Property at 90 Rockledge Dr, Stamford, CT 06902, 3 beds, 2 baths

$1,099,000

3 beds2 baths2,152 sq ft

90 Rockledge Dr, Stamford, CT 06902

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

$519,000

6 beds3 baths2,957 sq ft

161-163 Harriet St, Bridgeport, CT 06608

Property at 215 Mamanasco Rd #215, Ridgefield, CT 06877, 1 bed, 1 bath

$589,000

1 bed1 bath844 sq ft

215 Mamanasco Rd #215, Ridgefield, CT 06877

Property at 32 Josephine Evaristo Ave, Greenwich, CT 06830, 4 beds, 2 baths

$995,000

4 beds2 baths— sq ft

32 Josephine Evaristo Ave, Greenwich, CT 06830

Mike Parelli Real Estate LLC

Property at 145 Dewey St, Stratford, CT 06615, 5 beds, 5 baths

$749,900

5 beds5 baths4,219 sq ft

145 Dewey St, Stratford, CT 06615

Property at 744 Canaan Rd Unit Blg87 21, Bridgeport, CT 06610, 1 bed, 1 bath

$30,000

1 bed1 bath401 sq ft

744 Canaan Rd Unit Blg87 21, Bridgeport, CT 06610

Property at 70 Strawberry Hill Ave Unit 3-2C, Stamford, CT 06902, 1 bed, 1 bath

$285,000

1 bed1 bath949 sq ft

70 Strawberry Hill Ave Unit 3-2C, Stamford, CT 06902

Property at 380 Rockwell Ave, Stratford, CT 06615, 3 beds, 2 baths

$489,900

3 beds2 baths1,996 sq ft

380 Rockwell Ave, Stratford, CT 06615

Property at 18 Arbor Rd, Monroe, CT 06468, 6 beds, 2 baths

$619,900

6 beds2 baths2,418 sq ft

18 Arbor Rd, Monroe, CT 06468

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

$999,000

3 beds2.5 baths1,664 sq ft

21 Byram Rd, Greenwich, CT 06830

Property at 36 Middle River Rd, Danbury, CT 06811, 4 beds, 2 baths

$550,000

4 beds2 baths2,322 sq ft

36 Middle River Rd, Danbury, CT 06811

Property at 14 Highview Ave, Old Greenwich, CT 06870, 4 beds, 2.5 baths

$3,495,000

4 beds2.5 baths3,670 sq ft

14 Highview Ave, Old Greenwich, CT 06870

Property at 4 Crawford Rd, Westport, CT 06880, 5 beds, 3.5 baths

$2,595,000

5 beds3.5 baths4,471 sq ft

4 Crawford Rd, Westport, CT 06880

Property at 474 Brookside Rd, New Canaan, CT 06840, 6 beds, 4.5 baths

$5,895,000

6 beds4.5 baths7,723 sq ft

474 Brookside Rd, New Canaan, CT 06840

Property at 226 Ludlow St, Stamford, CT 06902, 6 beds, 2 baths

$759,900

6 beds2 baths2,620 sq ft

226 Ludlow St, Stamford, CT 06902

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 14 Rocky Hill Rd, New Fairfield, CT 06812, 3 beds, 3 baths

$500,000

3 beds3 baths1,850 sq ft

14 Rocky Hill Rd, New Fairfield, CT 06812

Property at 94 Soundview Rd, Ridgefield, CT 06877, 5 beds, 4.5 baths

$2,200,000

5 beds4.5 baths4,592 sq ft

94 Soundview Rd, Ridgefield, CT 06877

Property at 37 Allview Ave, Norwalk, CT 06854, 2 beds, 2 baths

$599,000

2 beds2 baths1,572 sq ft

37 Allview Ave, Norwalk, CT 06854

Viewing page 13 of 22

Based on information submitted to the MLS GRID as of Tue Oct 27 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 880 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 896 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.

More real estate resources for Fairfield County, CT

Nearby Counties

Cities

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Fairfield County, CT

How to buy a house in Fairfield County, CT

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

4 Redfin agents serving Fairfield County

Deals*

4.5

Satisfaction

203

Homes closed*

* Data from the last year

Popular Markets in Connecticut

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.