Vintage homes for sale & real estate in Fairfield, CT

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NEW 9 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Fairfield, CT:
Welcome to this beautifully updated 3 bedroom, 3 full bath Cape Cod offering 1,753 square feet of above grade living space in Fairfield. Conveniently located near Black Rock Turnpike, I-95, downtown Fairfield, Metro North train stations, shopping, and restaurants. Inside, hardwood floors flow throughout the main living areas, including a beautifully updated kitchen featuring white cabinetry, quartz countertops, stainless steel appliances, under cabinet lighting, and a separate pantry area. The spacious living room features custom shelving, while a bright and inviting enclosed sunroom offers the perfect space for a home office, additional family room, or simply a place to relax and enjoy the

$799,900

3 beds3 baths2,175 sq ft

106 Moritz Pl, Fairfield, CT 06824

Separate pantry area • Quartz countertops • Updated kitchen

NEW 12 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield, CT:
YOUR OPPORTUNITY AWAITS TO SETTLE IN AND ENJOY THE 2800+ SQUARE FEET OF LIVING AREA IN THIS 4+ BEDROOM, 2.5 BATH STRATFIELD HOME IDEAL FOR EXTENDED FAMILY OR IN-LAW WITH SEPARATE LEGAL APARTMENT PLUS PARTIALLY FINISHED WALK OUT LOWER LEVEL WITH OVERSIZED 2 CAR GARAGE AND PRIVATE REAR YARD. MAIN LEVEL LIVING AREA FEATURES LARGE LIVING ROOM WITH FIREPLACE, BANQUET SIZED FORMAL DINING ROOM AND SPACIOUS EAT IN KTICHEN. 3 GENEROUS SIZED BEDROOMS WITH EXTRA CLOSET SPACE COMPLETE THE MAIN HOME. UPPER LEVEL UNIT INCLUDES UPDATED KITCHEN WITH PERSONAL LAUNDRY, EXTENSIVE LIVING/DINING AREA AND ROOMY BEDROOM WITH EXTRA CLOSETS/STORAGE. ALL NEWER HEATING, HOT WATER HEATER, MAIN ELECTRIC SERVICE, LOWER

$829,500

4 beds2.5 baths2,810 sq ft

255 Fairfield Woods Rd, Fairfield, CT 06825

Newer heating • Private rear yard • Personal laundry

OPEN SAT, 12:30PM TO 2:30PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield, CT:
Welcome to 258 Bennett Street, a beautifully refreshed Fairfield home offering 4 bedrooms, 2 full bathrooms, and a versatile bonus room with direct backyard access. Recent improvements include new plumbing, new siding, a newer heating and cooling HVAC system, new flooring, a new kitchen, and updated bathrooms. Bright living and dining spaces, a first-floor full bath, semi-finished basement, garage, and private backyard add to the home's functionality. Located on a cul-de-sac and approximately an 11-minute walk to Owen Fish Park, with convenient access to North Stratfield School, shopping, dining, and transportation.

$649,999

4 beds2 baths1,427 sq ft

258 Bennett St, Fairfield, CT 06825

New plumbing • New kitchen • New siding

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Fairfield, CT:
Welcome to this beautifully renovated 4-bedroom, 2-bath Cape Cod home in Fairfield's University area. Offering 1,814 square feet of finished living space, this home features an open-concept kitchen with custom cabinetry, quartz countertops, a waterfall island, and stainless steel appliances. The main-level primary bedroom includes an updated en-suite bath, while three additional bedrooms and a full bath are located upstairs. Wide-plank flooring and recessed lighting complement the inviting living spaces, which include a living room with a fireplace and a separate family room. Outside, enjoy an oversized deck overlooking the spacious backyard. Additional features include central air and an a

$1,050,000

4 beds2 baths2,698 sq ft

1646 Jennings Rd, Fairfield, CT 06824

Custom cabinetry • Quartz countertops • Open-concept kitchen

ABOUT THIS HOME
Vintage Home for sale in Fairfield, CT:
Classic charm meets modern living in this beautifully renovated home, completely transformed down to the studs in 2018. Thoughtfully designed with an open, flexible floor plan, stylish finishes, and custom details throughout, this home offers the perfect blend of character and functionality. An inviting foyer welcomes you into the spacious main level, featuring a living room with a gas fireplace and wood shiplap detailing that flows seamlessly into the dining area and stunning kitchen. Highlights include quartz countertops, a breakfast bar, center island with storage, stainless steel KitchenAid appliances, and a custom built-in dining nook. A versatile office/playroom and powder room comple

$1,495,000

3 beds2.5 baths2,220 sq ft

121 Old Post Rd, Fairfield, CT 06824

Quartz countertops • Renovated home • Gas fireplace

Property at 43-45 Helen St, Fairfield, CT 06824, 7 beds, 3 baths

$1,299,000

7 beds3 baths1,890 sq ft

43-45 Helen St, Fairfield, CT 06824

Property at 63 Beacon View Dr, Fairfield, CT 06825, 1 bed, 1 bath

$320,000

1 bed1 bath625 sq ft

63 Beacon View Dr, Fairfield, CT 06825

Property at 33 New England Ave, Fairfield, CT 06824, 2 beds, 1.5 baths

$609,900

2 beds1.5 baths1,560 sq ft

33 New England Ave, Fairfield, CT 06824

Property at 633 Black Rock Tpke, Fairfield, CT 06825, 3 beds, 2 baths

$625,000

3 beds2 baths1,268 sq ft

633 Black Rock Tpke, Fairfield, CT 06825

Property at 45 Dogwood Ln, Fairfield, CT 06824, 4 beds, 2.5 baths

$1,185,000

4 beds2.5 baths2,752 sq ft

45 Dogwood Ln, Fairfield, CT 06824

Property at 126 Dwight St, Fairfield, CT 06824, 4 beds, 3 baths

$1,225,000

4 beds3 baths2,052 sq ft

126 Dwight St, Fairfield, CT 06824

Property at 98 Banks Pl, Southport, CT 06890, 4 beds, 5 baths

$5,995,000

4 beds5 baths5,699 sq ft

98 Banks Pl, Southport, CT 06890

Property at 1664 Melville Ave, Fairfield, CT 06825, 3 beds, 2 baths

$699,000

3 beds2 baths1,134 sq ft

1664 Melville Ave, Fairfield, CT 06825

Property at 9 Millspaugh Dr, Fairfield, CT 06824, 3 beds, 2 baths

$899,000

3 beds2 baths1,497 sq ft

9 Millspaugh Dr, Fairfield, CT 06824

Property at 15 Wheeler Park Pl, Fairfield, CT 06825, 4 beds, 3 baths

$997,500

4 beds3 baths2,528 sq ft

15 Wheeler Park Pl, Fairfield, CT 06825

Property at 72 Toll House Ln, Fairfield, CT 06825, 3 beds, 1 bath

$585,000

3 beds1 bath1,064 sq ft

72 Toll House Ln, Fairfield, CT 06825

Property at 70 Southfield Rd, Fairfield, CT 06824, 3 beds, 2.5 baths

$1,375,000

3 beds2.5 baths1,856 sq ft

70 Southfield Rd, Fairfield, CT 06824

Property at 36 Brooklawn Pkwy, Fairfield, CT 06825, 4 beds, 2.5 baths

$949,000

4 beds2.5 baths2,368 sq ft

36 Brooklawn Pkwy, Fairfield, CT 06825

Property at 295 Reid St, Fairfield, CT 06824, 3 beds, 2 baths

$749,900

3 beds2 baths1,393 sq ft

295 Reid St, Fairfield, CT 06824

Property at 195 Old South Rd, Southport, CT 06890, 4 beds, 4 baths

$4,950,000

4 beds4 baths4,254 sq ft

195 Old South Rd, Southport, CT 06890

Property at 38 Reynolds Dr, Fairfield, CT 06824, 3 beds, 2.5 baths

$845,000

3 beds2.5 baths1,898 sq ft

38 Reynolds Dr, Fairfield, CT 06824

Property at 1321 Brookside Dr, Fairfield, CT 06824, 2 beds, 2 baths

$1,500,000

2 beds2 baths2,064 sq ft

1321 Brookside Dr, Fairfield, CT 06824

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 38 Milandale Rd, Fairfield, CT 06824, 4 beds, 2 baths

$865,000

4 beds2 baths2,292 sq ft

38 Milandale Rd, Fairfield, CT 06824

Property at 2493 Redding Rd, Fairfield, CT 06824, 5 beds, 5 baths

$2,195,000

5 beds5 baths5,415 sq ft

2493 Redding Rd, Fairfield, CT 06824

Property at 11 Oldfield Dr, Fairfield, CT 06824, 4 beds, 2 baths

$1,150,000

4 beds2 baths2,124 sq ft

11 Oldfield Dr, Fairfield, CT 06824

Property at 85 Newman Pl, Fairfield, CT 06825, 4 beds, 2.5 baths

$989,000

4 beds2.5 baths2,338 sq ft

85 Newman Pl, Fairfield, CT 06825

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

$714,900

3 beds1.5 baths1,510 sq ft

155 Moody Ave, Fairfield, CT 06825

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 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 211 Old Farm Rd, Fairfield, CT 06825, 4 beds, 2.5 baths

$974,000

4 beds2.5 baths3,013 sq ft

211 Old Farm Rd, Fairfield, CT 06825

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 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 1035 Black Rock Tpke #1035, Fairfield, CT 06825, 3 beds, 1 bath

$369,000

3 beds1 bath1,280 sq ft

1035 Black Rock Tpke #1035, Fairfield, CT 06825

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 245 Cedar Rd, Southport, CT 06890, 4 beds, 3.5 baths

$2,349,000

4 beds3.5 baths3,519 sq ft

245 Cedar Rd, Southport, CT 06890

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 1074 Sturges Hwy, Fairfield, CT 06824, 5 beds, 4 baths

$2,690,000

5 beds4 baths4,540 sq ft

1074 Sturges Hwy, Fairfield, CT 06824

Property at 33 Melville Ave, Fairfield, CT 06825, 3 beds, 1.5 baths

$549,900

3 beds1.5 baths1,090 sq ft

33 Melville Ave, Fairfield, CT 06825

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

$599,000

4 beds2 baths1,142 sq ft

438 High St, Fairfield, CT 06824

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

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Based on information submitted to the MLS GRID as of Fri Oct 30 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

There are currently 70 vintage homes for sale in Fairfield at a median listing price of $1.06M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Fairfield stay on the market for 40 days and receive 8 offers. This map is refreshed with the newest listings in Fairfield every 15 minutes.

In the past month, 45 homes have been sold in Fairfield. In addition to houses in Fairfield, there were also 34 condos, 0 townhouses, and 3 multi-family units for sale in Fairfield last month. Find your dream home in Fairfield 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 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Fairfield. If you're looking to sell your home in the Fairfield area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Fairfield with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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