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

889 homes

Sort:

Recommended

OPEN SAT, 12PM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
SELLER WILL PAY UP TO 3% CLOSING COST & PREPAIDS ACCDEPTED OFFER! POOL, FENCED YARD, SCREENED PORCH & FIREPLACE - WELCOME TO 51 MAHER DRIVE! This inviting 3-bedroom, 1-1.5bath split-level offers the perfect combination of indoor comfort, outdoor enjoyment and convenient Norwalk living. Situated on a . 20-acre lot, the home features 6 rooms with a versatile split-level layout, a warm and inviting living area with fireplace, 3 bedrooms above with a possible 4th converting family room by placing a door at stairs, 1 full 1 Half baths and a one-car garage. Step outside and enjoy your own backyard retreat! The fenced-in yard provides privacy and plenty of room for entertaining, recrea

$699,900

3 beds1.5 baths1,076 sq ft

51 Maher Dr, Norwalk, CT 06850

Fenced yard • Convenient access • Screened porch

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Set on a quiet street in the desirable Cranbury neighborhood, this beautifully maintained 4-bedroom, 3 full bath home offers a wonderful blend of comfort, updates, and flexible living space. The main level features hardwood floors, a welcoming living room, dining room with fireplace, and a spacious kitchen with granite countertops, stainless steel appliances, and abundant cabinetry. The home is filled with natural light and includes updated bathrooms and a partially finished lower level ideal for a family room, home office, gym, recreation area, or guests. The lower level walks out to a large patio and private in-ground pool featuring new marble coping, a newer pool pump motor, and pool hea

$899,900

4 beds3 baths2,346 sq ft

59 Creeping Hemlock Dr, Norwalk, CT 06851

Spacious kitchen • Abundant cabinetry • Granite countertops

OPEN SUN, 12PM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Room to grow, space to entertain, and exceptional flexibility-this Colonial in the heart of Monroe offers a 5-bedroom setup on 1.2 acres of level, partially fenced land. With five rooms currently used as bedrooms, the home provides options for guests, work, and hobbies, adding substantial appeal at this price point. Town tax records designate the home as three bedrooms. Inside, the spacious living room features soaring cathedral ceilings, exposed wood beams, and beautiful hardwood floors. The kitchen offers stainless steel appliances and a peninsula with seating, opening to the dining area for easy everyday living and entertaining. Double doors lead to a large Trex deck overlooking the priv

$599,000

3 beds2 baths2,130 sq ft

148 Cross Hill Rd, Monroe, CT 06468

1.2 acres • Private backyard • 5 bedroom setup

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Step into the timeless charm of this beautifully maintained 1912 Colonial, rich with Victorian-inspired character and modern updates. A Home Warranty is included, providing added peace of mind for the new owner. Throughout the home, you'll find original woodwork, soaring ceilings, spacious rooms, decorative pillars separating the living and dining areas, and classic hardwood floors that showcase the home's historic appeal. The updated kitchen blends modern convenience with period charm and features newer appliances, including a refrigerator, dishwasher, gas range, microwave, washer, and dryer. The home offers 3 bedrooms and 1.5 baths, along with exciting possibilities on the third level. Pr

$699,000

3 beds1.5 baths1,766 sq ft

60 Nashvile Rd, Bethel, CT 06801

Original wood trim • Decorative pillars • New appliances

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Exceptional Investment Opportunity!! Discover the possibilities with this well-maintained legal three-family home, an ideal opportunity for both investors and owner occupants alike. Live comfortably in the spacious first-floor three-bedroom unit while enjoying rental income from the two additional apartments, or maximize the property's income potential as a full investment property. Each unit offers bright, sunny interiors, generous living space, and a welcoming atmosphere. The second-floor apartment features two bedrooms and one full bath, while the third-floor unit offers three bedrooms and one full bath. Recent energy efficient updates provide added value and peace of mind, including a b

$745,000

8 beds3 baths3,380 sq ft

291-293 Bruce Ave, Stratford, CT 06615

Brand-new roof • Natural gas furnaces • 5,227 sq ft lot

Property at 208 Birmingham St, Bridgeport, CT 06606, 1 bed, 1 bath

$274,900

1 bed1 bath1,149 sq ft

208 Birmingham St, Bridgeport, CT 06606

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 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

Property at 35 Beardsley Pkwy, Trumbull, CT 06611, 3 beds, 1.5 baths

$620,000

3 beds1.5 baths1,518 sq ft

35 Beardsley Pkwy, Trumbull, CT 06611

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 75 Hemlock St, Bridgeport, CT 06605, 3 beds, 2 baths

$499,900

3 beds2 baths1,300 sq ft

75 Hemlock St, Bridgeport, CT 06605

Property at 541 Sasco Hill Rd, Fairfield, CT 06824, 5 beds, 7.5 baths

$6,500,000

5 beds7.5 baths11,999 sq ft

541 Sasco Hill Rd, Fairfield, CT 06824

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 17 Fire Hill Rd, Ridgefield, CT 06877, 3 beds, 2 baths

$685,000

3 beds2 baths1,647 sq ft

17 Fire Hill Rd, Ridgefield, CT 06877

Property at 155 Moody Ave, Fairfield, CT 06825, 3 beds, 1.5 baths

$730,000

3 beds1.5 baths1,510 sq ft

155 Moody Ave, Fairfield, CT 06825

Property at 175 Eaton St, Bridgeport, CT 06604, 3 beds, 1.5 baths

$449,999

3 beds1.5 baths2,000 sq ft

175 Eaton St, Bridgeport, CT 06604

Property at 259 Pauline St, Stratford, CT 06615, 5 beds, 2 baths

$695,000

5 beds2 baths2,746 sq ft

259 Pauline St, Stratford, CT 06615

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 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 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 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 39 Sorghum Rd, Shelton, CT 06484, 3 beds, 3 baths

$639,999

3 beds3 baths2,442 sq ft

39 Sorghum Rd, Shelton, CT 06484

Property at 145 Canal St #13, Shelton, CT 06484, 2 beds, 2 baths

$229,000

2 beds2 baths1,042 sq ft

145 Canal St #13, Shelton, CT 06484

Property at 15 Flat Swamp Rd, Newtown, CT 06470, 3 beds, 2 baths

$609,000

3 beds2 baths1,616 sq ft

15 Flat Swamp Rd, Newtown, CT 06470

Property at 10 Hillwood Pl, Norwalk, CT 06850, 4 beds, 2.5 baths

$699,000

4 beds2.5 baths2,150 sq ft

10 Hillwood Pl, Norwalk, CT 06850

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 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 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 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 1285 Hope St #12, Stamford, CT 06907, 2 beds, 1 bath

$429,000

2 beds1 bath800 sq ft

1285 Hope St #12, Stamford, CT 06907

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 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 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 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 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 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 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 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 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 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

Viewing page 6 of 22

Based on information submitted to the MLS GRID as of Fri Oct 23 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 882 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 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

Cities

Nearby Counties

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.