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

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ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Classic New England charm meets modern luxury in this beautifully updated 1921 Colonial. Perfectly situated just minutes from the quaint Georgetown boutique shops , restaurants, and Route 7. Set on nearly half an acre lot, this home offers effortless living and entertaining inside and out. The heart of the home features a renovated eat-in kitchen with timeless marble countertops, a 4 seated island, and newer stainless-steel appliances. Entertain with ease in the formal dining room, unwind by the gas fireplace in the living room, or settle into the versatile sunroom - equally suited as a home office. Upstairs, the primary suite is a true sanctuary, complete with gas fireplace, a spacious wal

$1,099,000

4 beds2 baths3,124 sq ft

207 Redding Rd, Redding, CT 06896

Formal dining room • Primary suite • Gas fireplace

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
A beautifully preserved historic treasure, 143 Chestnut Hill blends more than a century of character with extraordinary craftsmanship and modern-day function. Built in 1900, with just three owners and lovingly curated by the current owners for over 40 years, the home has been thoughtfully expanded while honoring its original wide-board floors, stonework, doors, millwork and reclaimed antique beams. Throughout, extensive custom cabinetry was designed specifically for each room, with inset dressers, drawers, armoires and ingenious storage creating a true place for everything. At the heart of the home is a spectacular chef's kitchen with a 7ft island topped in reclaimed white oak, 48" Ber

$2,375,000

6 beds5.5 baths5,455 sq ft

143 Chestnut Hill Rd, Wilton, CT 06897

Custom cabinetry • Historic treasure • Wide-board floors

OPEN SAT, 1PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
SUNNY 3 BEDROOM, 2 BATH END UNIT IN A COVETED CORNER OF PUTNAM PARK. Tucked away in a delightful, secluded courtyard, this spacious home has 3 exposures, flexible floor plan, 1-level living on 2nd floor, and wide open views of lush lawns, gardens & greenery. Living Room with balcony facing courtyard could be a Living/Dining Room. The 3rd Bedroom could be a Family Room, Home Office or Formal Dining Room, as currently used. Master Bedroom has walk-in closet & ensuite Bath w/ stall shower. Hardwood floors, new windows, crown molding. On 12 landscaped acres in a pet-friendly complex in prime central Greenwich. Onsite parking; garage rental $85/mo. Near Whole Foods, just blocks to Gr

$700,000

3 beds2 baths1,250 sq ft

61 Putnam Park #61, Greenwich, CT 06830

1-level living • Flexible floor plan • Walk-in closet

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Step into a storybook setting at 150 Holmes Avenue, where the timeless elegance of a classic Victorian meets a meticulous, top-to-bottom modernization. From the moment you approach you'll feel the historic charm that defines this Darien gem. Inside, the transformation is striking. The entire interior has been freshly painted in a crisp, sophisticated palette, perfectly complementing the hardwood floors throughout. The heart of the home is a beautifully updated kitchen, blending contemporary convenience with the home's original soulful character. Every corner of this residence shines with pride of ownership; it is exceptionally clean, bright, and truly move-in ready. Whether you are hosting

$1,795,000

4 beds2 baths2,091 sq ft

150 Holmes Ave, Darien, CT 06820

Wrap-around porch • Updated kitchen • 0.24 acre lot

OPEN SUN, 1PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
This is a truly must-see home! A modernized Mid-Century Contemporary residence with a peaceful babbling brook view, offering 3 bedrooms and 3 full bathrooms in a condition that feels as close to new construction as possible. The home features all-new hardwood floors, 9-foot ceilings, and dramatic floor-to-ceiling windows that fill the space with natural light. A striking stone fireplace anchors the living room, while the main level also includes a convenient laundry/mudroom and a bright breakfast room. Outdoor living is elevated with two spacious decks and a patio overlooking the serene setting. The lower-level family room offers an additional fireplace, creating a warm and inviting retreat

$1,195,000

3 beds3 baths2,169 sq ft

128 Linley Dr, Fairfield, CT 06825

Babbling brook view • Breakfast room • Laundry mudroom

Property at 716 Cheese Spring Rd, New Canaan, CT 06840, 5 beds, 5.5 baths

$3,600,000

5 beds5.5 baths5,135 sq ft

716 Cheese Spring Rd, New Canaan, CT 06840

Property at 38 Carlisle Pl, Stamford, CT 06902, 3 beds, 2 baths

$739,000

3 beds2 baths1,600 sq ft

38 Carlisle Pl, Stamford, CT 06902

Property at 325 Lafayette St #3302, Bridgeport, CT 06604, 2 beds, 1 bath

$155,000

2 beds1 bath890 sq ft

325 Lafayette St #3302, Bridgeport, CT 06604

Property at 1 Tulip Tree Ln, Norwalk, CT 06851, 4 beds, 4 baths

$1,395,000

4 beds4 baths5,729 sq ft

1 Tulip Tree Ln, Norwalk, CT 06851

Property at 360 Pansy Rd, Fairfield, CT 06824, 3 beds, 3 baths

$675,000

3 beds3 baths2,688 sq ft

360 Pansy Rd, Fairfield, CT 06824

Property at 61 Clapboard Hill Rd, Westport, CT 06880, 4 beds, 3.5 baths

$3,698,000

4 beds3.5 baths3,418 sq ft

61 Clapboard Hill Rd, Westport, CT 06880

Property at 94 Ascolese Rd, Trumbull, CT 06611, 4 beds, 2 baths

$599,900

4 beds2 baths2,482 sq ft

94 Ascolese Rd, Trumbull, CT 06611

Property at 83 Pepper St, Monroe, CT 06468, 3 beds, 2.5 baths

$649,900

3 beds2.5 baths2,308 sq ft

83 Pepper St, Monroe, CT 06468

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

$399,000

2 beds1 bath1,171 sq ft

150 Route 39 S, Sherman, CT 06784

Property at 39 Powder Horn Hill Rd, Wilton, CT 06897, 5 beds, 4.5 baths

$1,799,000

5 beds4.5 baths5,231 sq ft

39 Powder Horn Hill Rd, Wilton, CT 06897

Property at 12 Sherman Ave #2, Greenwich, CT 06831, 2 beds, 2.5 baths

$895,000

2 beds2.5 baths1,695 sq ft

12 Sherman Ave #2, Greenwich, CT 06831

Property at 126 Oldfield Rd, Fairfield, CT 06824, 3 beds, 2.5 baths

$1,315,000

3 beds2.5 baths1,984 sq ft

126 Oldfield Rd, Fairfield, CT 06824

Property at 32 Depalma Ln, Danbury, CT 06811, 2 beds, 1 bath

$299,900

2 beds1 bath1,036 sq ft

32 Depalma Ln, Danbury, CT 06811

Property at 21 Tyler Dr, Stamford, CT 06903, 3 beds, 3 baths

$1,150,000

3 beds3 baths2,484 sq ft

21 Tyler Dr, Stamford, CT 06903

Property at 233 Beaumont St, Fairfield, CT 06824, 4 beds, 2 baths

$1,295,000

4 beds2 baths2,684 sq ft

233 Beaumont St, Fairfield, CT 06824

Property at 14 Park Ln, Norwalk, CT 06851, 3 beds, 2.5 baths

$1,425,000

3 beds2.5 baths1,616 sq ft

14 Park Ln, Norwalk, CT 06851

Property at 9 Stonecrop Rd, Norwalk, CT 06851, 4 beds, 2 baths

$695,000

4 beds2 baths2,444 sq ft

9 Stonecrop Rd, Norwalk, CT 06851

Property at 6 Martin Dl, Greenwich, CT 06830, 4 beds, 4 baths

$6,950,000

4 beds4 baths4,239 sq ft

6 Martin Dl, Greenwich, CT 06830

Property at 20 Glen Arden Dr S, Fairfield, CT 06824, 3 beds, 3 baths

$995,000

3 beds3 baths2,940 sq ft

20 Glen Arden Dr S, Fairfield, CT 06824

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 5 Michael St, Norwalk, CT 06854, 3 beds, 2 baths

$679,000

3 beds2 baths1,428 sq ft

5 Michael St, Norwalk, CT 06854

Property at 36 Sultan St, Stratford, CT 06614, 3 beds, 1.5 baths

$499,999

3 beds1.5 baths1,422 sq ft

36 Sultan St, Stratford, CT 06614

Property at 97 Gorham Rd, Fairfield, CT 06824, 4 beds, 2 baths

$1,149,000

4 beds2 baths1,697 sq ft

97 Gorham Rd, Fairfield, CT 06824

Property at 78 Knapp St, Stamford, CT 06907, 4 beds, 2.5 baths

$810,000

4 beds2.5 baths2,482 sq ft

78 Knapp St, Stamford, CT 06907

Property at 19 Starlight Dr, Norwalk, CT 06851, 3 beds, 2 baths

$799,000

3 beds2 baths3,216 sq ft

19 Starlight Dr, Norwalk, CT 06851

Property at 20 Mountain Rd, Wilton, CT 06897, 3 beds, 2.5 baths

$975,000

3 beds2.5 baths2,125 sq ft

20 Mountain Rd, Wilton, CT 06897

Property at 10 Blackberry Ln, Norwalk, CT 06850, 3 beds, 2.5 baths

$799,000

3 beds2.5 baths2,611 sq ft

10 Blackberry Ln, Norwalk, CT 06850

Property at 23 Dana Rd, Danbury, CT 06811, 3 beds, 1 bath

$489,900

3 beds1 bath2,304 sq ft

23 Dana Rd, Danbury, CT 06811

Property at 90 Taconic Rd, Greenwich, CT 06831, 5 beds, 3.5 baths

$3,100,000

5 beds3.5 baths3,791 sq ft

90 Taconic Rd, Greenwich, CT 06831

Property at 205 Glenville Rd, Greenwich, CT 06831, 3 beds, 2 baths

$1,375,000

3 beds2 baths1,368 sq ft

205 Glenville Rd, Greenwich, CT 06831

Property at 170 S Main St, Newtown, CT 06470, 2 beds, 1 bath

$450,000

2 beds1 bath800 sq ft

170 S Main St, Newtown, CT 06470

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 4 Bradley St, Westport, CT 06880, 5 beds, 4 baths

$2,885,000

5 beds4 baths3,255 sq ft

4 Bradley St, Westport, CT 06880

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

$1,050,000

4 beds2.5 baths3,013 sq ft

211 Old Farm Rd, Fairfield, CT 06825

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

$495,000

2 beds1 bath892 sq ft

205 Mountain Rd, Wilton, CT 06897

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Based on information submitted to the MLS GRID as of Thu Oct 08 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 844 vintage homes for sale in Fairfield County at a median listing price of $700K. 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, 747 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 892 condos, 1 townhouse, and 213 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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