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:
VERY motivated sellers! Reduced below recent bank appraisal! Beautifully situated on a spacious corner lot, this exceptional home enjoys the added privacy of a quiet dead-end street as its crossroad. Offering over 3,300 sq. ft of living space, this versatile floor plan provides generous room for today's lifestyle w/ endless possibilities for customization. The bright & inviting main level features a spacious living room, dining area, updated kitchen w/ sliders to deck, & an expansive family room perfect for gatherings & entertaining leading to patio. The oversized laundry room offers excellent potential for custom built-in cabinetry, a folding station, mudroom organization,

$945,000

4 beds3 baths3,300 sq ft

311 Mountain Rd, Wilton, CT 06897

Walk-in closet • Updated kitchen • Corner lot

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Classic New England Charm in West Redding Center! This charming home offers far more than meets the eye. Hardwood floors flow throughout, beginning in the spacious living room, where a beautiful stone fireplace adds warmth, character, and timeless appeal. -------- The thoughtfully renovated kitchen features granite countertops, a center island, and stainless-steel appliances, all new in 2024, including an induction range. Just off the kitchen is a flexible den or dining room, along with a convenient mudroom/laundry room offering abundant storage and access to a three-quarter bath. The light-filled sunroom overlooks the private backyard, creating a bright and inviting place to relax. An addi

$699,000

4 beds2 baths2,004 sq ft

248 Simpaug Tpke, Redding, CT 06896

Renovated kitchen • Stone fireplace • Granite countertops

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Beautifully expanded and thoughtfully renovated Cape offering a wonderful blend of classic charm and modern updates. This inviting 4 bedroom, 2 full bath home features a flexible floor plan with comfortable living spaces and plenty of room to grow. A versatile den/office opens through sliders to a large deck overlooking the landscaped fully fenced yard, perfect for entertaining, relaxing, or enjoying outdoor living. The outdoor space includes a patio and pergola, creating an ideal setting for gatherings or quiet afternoons. The fully finished attic provides valuable additional living space, while the under-house garage offers convenient parking and storage. Numerous updates throughout make

$635,000

4 beds2 baths1,322 sq ft

91 Ward St, Norwalk, CT 06851

Large deck • Flexible floor plan • Expanded cape

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Once in a blue moon does a home like this become available! Nestled in the Webb Mountain region of Monroe, this 7.5-acre property features a 4 BD, 2.5 BTH Cape-style home with all the comforts and updates for today's living, while preserving the peaceful, serene charm of yesteryear. Step back in time & enjoy bucolic open fields, a gardener's paradise with raspberry bushes & homegrown vegetables of every kind & plenty of land where pets can roam freely! A lovely custom cabana, fully fenced I/G pool & patio create the perfect setting for entertaining. With 3,074 SQFT plus a finished LL with a second FPL, this spacious home boasts numerous upgrades & improvements

$920,000

4 beds2.5 baths3,074 sq ft

195 Webb Cir, Monroe, CT 06468

Finished ll • Custom cabana • Conservation land

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Welcome to 63 Harral Ave, a fully renovated 3-bedroom, 2-full-bath single-family home in Bridgeport. This three-story home offers approximately 1,726 square feet of living space with updated finishes throughout. The first floor features a living room, dining area, kitchen, full bathroom, and washer and dryer hookups. The second floor offers three bedrooms and a full bathroom. The third floor provides additional living space, offering flexibility for a home office, recreation area, or other use. The property sits on approximately 0.05 acres and is conveniently located near shopping, dining, parks, transportation, and other local amenities. The home is fully renovated and ready for occupancy.

$375,000

3 beds2 baths1,726 sq ft

63 Harral Ave, Bridgeport, CT 06604

Fully renovated • Convenient access • 2,178 sq ft lot

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

$450,000

3 beds2 baths1,996 sq ft

380 Rockwell Ave, Stratford, CT 06615

Property at 181 Georgetown Rd, Weston, CT 06883, 4 beds, 3.5 baths

$1,249,000

4 beds3.5 baths2,958 sq ft

181 Georgetown Rd, Weston, CT 06883

Property at 100 Brenair Ter, Stratford, CT 06615, 4 beds, 1.5 baths

$550,000

4 beds1.5 baths2,084 sq ft

100 Brenair Ter, Stratford, CT 06615

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 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 66 Cayer Cir, Shelton, CT 06484, 4 beds, 2.5 baths

$824,900

4 beds2.5 baths3,002 sq ft

66 Cayer Cir, Shelton, CT 06484

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 28 Walnut Hill Rd, Bethel, CT 06801, 5 beds, 2 baths

$599,999

5 beds2 baths2,361 sq ft

28 Walnut Hill Rd, Bethel, CT 06801

Property at 33 Assisi Way, Norwalk, CT 06854, 3 beds, 2 baths

$639,999

3 beds2 baths2,029 sq ft

33 Assisi Way, Norwalk, CT 06854

Property at 13 Terre Haute Rd, Danbury, CT 06810, 3 beds, 2 baths

$465,000

3 beds2 baths1,695 sq ft

13 Terre Haute Rd, Danbury, CT 06810

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 28 Gregory Rd, Cos Cob, CT 06807, 4 beds, 3 baths

$1,695,000

4 beds3 baths3,597 sq ft

28 Gregory Rd, Cos Cob, CT 06807

Property at 34 Lansing Ave, Trumbull, CT 06611, 3 beds, 2 baths

$499,000

3 beds2 baths1,608 sq ft

34 Lansing Ave, Trumbull, CT 06611

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 73 Carlson Ave, Bridgeport, CT 06606, 3 beds, 1 bath

$375,000

3 beds1 bath1,472 sq ft

73 Carlson Ave, Bridgeport, CT 06606

Property at 37 Mary Ln, Riverside, CT 06878, 5 beds, 3.5 baths

$2,999,000

5 beds3.5 baths3,176 sq ft

37 Mary Ln, Riverside, CT 06878

Property at 23 Longview Dr, Brookfield, CT 06804, 2 beds, 1 bath

$475,000

2 beds1 bath1,101 sq ft

23 Longview Dr, Brookfield, CT 06804

Property at 406 Lakeside Dr, Bridgeport, CT 06606, 4 beds, 2 baths

$489,999

4 beds2 baths2,227 sq ft

406 Lakeside Dr, Bridgeport, CT 06606

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 Gravel Island Rd, New Canaan, CT 06840, 4 beds, 3 baths

$1,999,000

4 beds3 baths4,183 sq ft

Gravel Island Rd, New Canaan, CT 06840

Property at 3 Catalpa St, Norwalk, CT 06851, 3 beds, 2 baths

$598,000

3 beds2 baths1,364 sq ft

3 Catalpa St, Norwalk, CT 06851

Property at 161 Delaware Dr, Stratford, CT 06614, 4 beds, 2.5 baths

$550,000

4 beds2.5 baths2,826 sq ft

161 Delaware Dr, Stratford, CT 06614

Property at 198 Castle Ave, Fairfield, CT 06825, 4 beds, 2.5 baths

$810,000

4 beds2.5 baths2,205 sq ft

198 Castle Ave, Fairfield, CT 06825

Property at 39 Crane Rd, Stamford, CT 06902, 3 beds, 2 baths

$829,000

3 beds2 baths2,063 sq ft

39 Crane Rd, Stamford, CT 06902

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 149 Dudley Rd, Wilton, CT 06897, 5 beds, 5.5 baths

$2,995,000

5 beds5.5 baths5,940 sq ft

149 Dudley Rd, Wilton, CT 06897

Property at 164 Round Hill Rd, Greenwich, CT 06831, 8 beds, 12.5 baths

$14,600,000

8 beds12.5 baths17,121 sq ft

164 Round Hill Rd, Greenwich, CT 06831

Property at 29 W Wooster St, Danbury, CT 06810, 2 beds, 2 baths

$359,000

2 beds2 baths1,248 sq ft

29 W Wooster St, Danbury, CT 06810

Property at 105 Washington Pkwy, Stratford, CT 06615, 4 beds, 2 baths

$650,000

4 beds2 baths2,298 sq ft

105 Washington Pkwy, Stratford, CT 06615

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 163 Huntingtown Rd, Newtown, CT 06470, 2 beds, 1 bath

$350,000

2 beds1 bath960 sq ft

163 Huntingtown Rd, Newtown, CT 06470

Property at 296 Bennetts Farm Rd, Ridgefield, CT 06877, 2 beds, 2 baths

$699,000

2 beds2 baths1,548 sq ft

296 Bennetts Farm Rd, Ridgefield, CT 06877

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 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 111 Mercer St, Stratford, CT 06614, 3 beds, 2.5 baths

$499,900

3 beds2.5 baths1,870 sq ft

111 Mercer St, Stratford, CT 06614

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

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Based on information submitted to the MLS GRID as of Mon Nov 09 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 824 vintage homes for sale in Fairfield County at a median listing price of $690K. 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 51 days and receive 3 offers. This map is refreshed with the newest listings in Fairfield County every 15 minutes.

In the past month, 750 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 901 condos, 2 townhouses, and 241 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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