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

883 homes

Sort:

Recommended

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:
This beautifully updated Cape Cod home offers 3 bedrooms and 3 full updated baths. The home features central air conditioning, newer windows and doors, and hardwood floors throughout. The renovated eat-in kitchen with center island has stainless-steel appliances and provides great space for everyday meals, while the formal dining room offers additional space for special gatherings. The walk-out finished basement includes a convenient washer and dryer and also provides versatile additional living space. Outside, enjoy the spacious, level yard. Walking distance to the elementary school. Home warranty to the buyer for one year included.

$879,000

3 beds3 baths1,939 sq ft

71 Country Rd, Fairfield, CT 06824

Newer windows • Granite countertops • Hardwood floors

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

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

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Opportunity awaits at Success Village! Offered at $65,900, this spacious 3-bedroom, 1-bath co-op is one of the larger-style units within the complex and features both a fenced front yard and fenced backyard-a great bonus for outdoor enjoyment. Held within the same family since originally built, this home is ready for its next chapter and offers plenty of potential for a buyer willing to bring their vision and make it their own. Property is being sold strictly AS IS, WHERE IS and CASH ONLY. Contents remaining in the unit at closing will convey with the property; some items may be removed prior to closing. Owner-occupants. Buyer and all interested parties are subject to association approval.

$65,900

3 beds1 bath737 sq ft

28 Court B Bldg 21, Bridgeport, CT 06610

Fenced front yard • Fenced backyard • $689 HOA

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 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 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 162 Anson St, Stratford, CT 06614, 4 beds, 1.5 baths

$480,000

4 beds1.5 baths1,896 sq ft

162 Anson St, Stratford, CT 06614

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 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 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 59 Gillotti Rd, New Fairfield, CT 06812, 1 bed, 1 bath

$349,000

1 bed1 bath736 sq ft

59 Gillotti Rd, New Fairfield, CT 06812

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 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 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 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 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 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 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 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 95 Disbrow St, Stratford, CT 06614, 3 beds, 1 bath

$459,000

3 beds1 bath1,352 sq ft

95 Disbrow St, Stratford, CT 06614

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 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 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 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 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 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 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 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 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 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 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 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 135 Legion Ave, Stratford, CT 06614, 4 beds, 2 baths

$409,900

4 beds2 baths1,287 sq ft

135 Legion Ave, Stratford, CT 06614

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

$485,000

3 beds1 bath1,344 sq ft

109 Woolsley Ave, Trumbull, CT 06611

Property at 24-22 Evers Ct, Bridgeport, NY 06610, 4 beds, 2 baths

$499,000

4 beds2 baths— sq ft

24-22 Evers Ct, Bridgeport, NY 06610

Listing by RE/MAX Voyage Realty

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

Viewing page 6 of 22

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 876 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.

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

201

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.