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:
Escape the city and discover this wonderful estate, formerly Brinsmade Farm, in Sherman, Connecticut, offered for the first time in 60 years. Set on approximately 10 scenic acres in the heart of charming Sherman, this exceptional country home combines timeless New England charm with modern living. Originally a working dairy farm, the property was transformed in 1945 when the barn became a private residence. The estate includes three dwellings, perfect for extended family, guests, or multi-generational living-the Main House, Carriage House, and Pool House-offering approximately 5,200 sq ft with 6 bedrooms and 5 full baths. The Main House showcases cathedral ceilings, exposed beams, wide-plan

$1,849,000

6 beds5 baths5,500 sq ft

6 Brinsmade Ln, Sherman, CT 06784

12 acre lot • 6 garage spots • Pool

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Wonderful mid-city location. This Hampshire House apt is a short walk to vibrant downtown, Tully Center, restaurants, theater, shopping, transportation, etc. One level living with hardwood floors throughout, extra storage unit, and well-maintained grounds. Heat, hot water and taxes included in common charges. Don't miss out on this well-maintained unit. No dogs allowed, only cats

$185,000

1 bed1 bath740 sq ft

108 Strawberry Hill Ave #1, Stamford, CT 06902

Extra storage unit • Mid-city location • Hardwood floors

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
This inviting 2-bedroom home beautifully blends the charm of the past with thoughtful modern upgrades. The moment you step inside, you'll appreciate the cozy ambiance alongside the convenience of contemporary living. The kitchen has been completely updated, featuring modern cabinetry, sleek countertops, and quality appliances-perfect for everyday cooking and entertaining guests. Both bathrooms have also been fully renovated, offering stylish fixtures and comfortable layouts for your daily routine. Since 2006, the current owner has meticulously updated the home, preserving its original character while enhancing functionality and aesthetics. The result is a space that feels warm and welcoming

$449,900

2 beds1.5 baths804 sq ft

700 Huntington Rd, Stratford, CT 06614

Quality appliances • Stylish fixtures • Modern cabinetry

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Chateau Rochamore - a French Normandy stone manor of timeless grace - sits on over three park-like acres in North Stamford. Designed at the turn of the century by renowned New York City architect Gustave Steinbeck as a summer residence for himself and his family, this historic landmark offers nearly 6,000 square feet of elegant living space steeped in old-world craftsmanship and charm. From the moment you pass through the stone-pillared gates, the home's architectural details captivate: ornamental hand-carved gargoyles preside above the three-car garage, stately stone chimneys rise above the slate roof, and every element reflects the artistry of a bygone era. Step into the great hall, where

$2,150,000

5 beds3.5 baths5,593 sq ft

271 Hunting Ridge Rd, Stamford, CT 06903

3.25 acre lot • 3 garage spots • Built 1906

ABOUT THIS HOME
Vintage Home for sale in Fairfield County, CT:
Newly renovated multifamily located in a convenient location. New kitchens, baths and flooring in all units. New siding. Freshly paved driveway with 4 car garage for storage. Very large storage shed with lots of potential. Great opportunity for investor or owner occupant! Motivated Seller. Please note driveway is too narrow for a car to access backyard.

$599,000

4 beds2 baths2,217 sq ft

530 Jane St, Bridgeport, CT 06608

New kitchens • New baths • New siding

Property at 162 Cottage St, Bridgeport, CT 06605, 3 beds, 2 baths

$420,000

3 beds2 baths1,781 sq ft

162 Cottage St, Bridgeport, CT 06605

Property at 24 Valley Rd, Cos Cob, CT 06807, 4 beds, 4.5 baths

$2,398,000

4 beds4.5 baths3,221 sq ft

24 Valley Rd, Cos Cob, CT 06807

Property at 50 Goddard Ave, Bridgeport, CT 06610, 4 beds, 1 bath

$350,000

4 beds1 bath1,482 sq ft

50 Goddard Ave, Bridgeport, CT 06610

Property at 400 East Ave, Bridgeport, CT 06610, 3 beds, 1 bath

$339,000

3 beds1 bath1,267 sq ft

400 East Ave, Bridgeport, CT 06610

Property at 89 Grace St, Fairfield, CT 06825, 2 beds, 1.5 baths

$325,000

2 beds1.5 baths715 sq ft

89 Grace St, Fairfield, CT 06825

Property at 59 Lenox Ave, Stratford, CT 06615, 2 beds, 2.5 baths

$319,000

2 beds2.5 baths1,776 sq ft

59 Lenox Ave, Stratford, CT 06615

Property at 40 Orchard St, Stamford, CT 06902, 4 beds, 2 baths

$499,900

4 beds2 baths1,878 sq ft

40 Orchard St, Stamford, CT 06902

Property at 887 Westover Rd, Stamford, CT 06902, 5 beds, 4.5 baths

$979,000

5 beds4.5 baths3,530 sq ft

887 Westover Rd, Stamford, CT 06902

Property at 477 Newtown Tpke, Redding, CT 06896, 2 beds, 2 baths

$589,000

2 beds2 baths1,618 sq ft

477 Newtown Tpke, Redding, CT 06896

Property at 204 Parade Hill Rd, New Canaan, CT 06840, 4 beds, 4 baths

$2,595,000

4 beds4 baths3,260 sq ft

204 Parade Hill Rd, New Canaan, CT 06840

Property at 492 Newtown Tpke, Weston, CT 06883, 1 bed, 1 bath

$349,000

1 bed1 bath576 sq ft

492 Newtown Tpke, Weston, CT 06883

Property at 1018 North St, Greenwich, CT 06831, 3 beds, 1.5 baths

$999,000

3 beds1.5 baths1,546 sq ft

1018 North St, Greenwich, CT 06831

Property at 95 Byram Rd, Greenwich, CT 06830, 2 beds, 1 bath

$750,000

2 beds1 bath881 sq ft

95 Byram Rd, Greenwich, CT 06830

Property at 1260 Elm St, Stratford, CT 06615, 3 beds, 2 baths

$575,000

3 beds2 baths1,675 sq ft

1260 Elm St, Stratford, CT 06615

Property at 175 Lake Ave, Greenwich, CT 06830, 5 beds, 4.5 baths

$3,295,000

5 beds4.5 baths3,056 sq ft

175 Lake Ave, Greenwich, CT 06830

Property at 29 Carol St, Danbury, CT 06810, 3 beds, 4 baths

$650,000

3 beds4 baths2,050 sq ft

29 Carol St, Danbury, CT 06810

Property at 81 Currituck Rd, Newtown, CT 06470, 3 beds, 2 baths

$1,595,000

3 beds2 baths2,906 sq ft

81 Currituck Rd, Newtown, CT 06470

Property at 27 Wellington Dr, Stamford, CT 06903, 4 beds, 3 baths

$799,999

4 beds3 baths2,402 sq ft

27 Wellington Dr, Stamford, CT 06903

Property at 213 Mamanasco Rd, Ridgefield, CT 06877, 1 bed, 1.5 baths

$399,000

1 bed1.5 baths802 sq ft

213 Mamanasco Rd, Ridgefield, CT 06877

Property at 107 Dewey St, Stratford, CT 06615, 4 beds, 2 baths

$484,000

4 beds2 baths1,647 sq ft

107 Dewey St, Stratford, CT 06615

Property at 1170 South Ave, Stratford, CT 06615, 3 beds, 2.5 baths

$529,900

3 beds2.5 baths1,841 sq ft

1170 South Ave, Stratford, CT 06615

Property at 196 Avon St, Stratford, CT 06615, 5 beds, 3 baths

$499,900

5 beds3 baths2,178 sq ft

196 Avon St, Stratford, CT 06615

Property at 43 Sterling Rd, Greenwich, CT 06831, 7 beds, 7 baths

$3,895,000

7 beds7 baths9,267 sq ft

43 Sterling Rd, Greenwich, CT 06831

Property at 1 Blue Mountain Rdg, Norwalk, CT 06851, 3 beds, 3 baths

$849,000

3 beds3 baths2,489 sq ft

1 Blue Mountain Rdg, Norwalk, CT 06851

Property at 724 Capitol Ave, Bridgeport, CT 06606, 10 beds, 3 baths

$735,000

10 beds3 baths3,318 sq ft

724 Capitol Ave, Bridgeport, CT 06606

Property at 71 Peaceable Ridge Rd, Ridgefield, CT 06877, 4 beds, 4.5 baths

$2,695,000

4 beds4.5 baths3,218 sq ft

71 Peaceable Ridge Rd, Ridgefield, CT 06877

Property at 880 Pearl Harbor St, Bridgeport, CT 06610, 2 beds, 2 baths

$359,000

2 beds2 baths1,196 sq ft

880 Pearl Harbor St, Bridgeport, CT 06610

Property at 32 Old Green Rd, Sandy Hook, CT 06482, 3 beds, 1 bath

$499,500

3 beds1 bath1,724 sq ft

32 Old Green Rd, Sandy Hook, CT 06482

Property at 4 Colony Rd, Weston, CT 06883, 2 beds, 2 baths

$829,000

2 beds2 baths1,689 sq ft

4 Colony Rd, Weston, CT 06883

Property at 39 Jane St, Bridgeport, CT 06608, 6 beds, 2 baths

$479,000

6 beds2 baths2,156 sq ft

39 Jane St, Bridgeport, CT 06608

Property at 1034 Connecticut Ave, Bridgeport, CT 06607, 2 beds, 1 bath

$40,000

2 beds1 bath99,999 sq ft

1034 Connecticut Ave, Bridgeport, CT 06607

Property at 643 Newfield Ave, Bridgeport, CT 06607, 6 beds, 3 baths

$460,000

6 beds3 baths2,644 sq ft

643 Newfield Ave, Bridgeport, CT 06607

Property at 1148 Hope St, Stamford, CT 06907, 3 beds, 2 baths

$849,900

3 beds2 baths2,397 sq ft

1148 Hope St, Stamford, CT 06907

Property at 999 Monroe Tpke, Monroe, CT 06468, 3 beds, 2 baths

$595,000

3 beds2 baths2,382 sq ft

999 Monroe Tpke, Monroe, CT 06468

Property at 130 Ash St, Stratford, CT 06615, 3 beds, 1 bath

$500,000

3 beds1 bath1,697 sq ft

130 Ash St, Stratford, CT 06615

Property at 5 Rabbit Ln, Brookfield, CT 06804, 2 beds, 1.5 baths

$430,000

2 beds1.5 baths1,015 sq ft

5 Rabbit Ln, Brookfield, CT 06804

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Based on information submitted to the MLS GRID as of Sun Nov 30 2025. 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 508 vintage homes for sale in Fairfield County at a median listing price of $680K. 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 48 days and receive 4 offers. This map is refreshed with the newest listings in Fairfield County every 15 minutes.

In the past month, 896 homes have been sold in Fairfield County. In addition to houses in Fairfield County, there were also 778 condos, 1 townhouse, and 200 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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