Vintage homes for sale & real estate in Connecticut, CT

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ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the home's historic integrity while introducing refined, livable spaces. Interiors by acclaimed designer Katie Ridder bring a fresh yet classic sensibility, blending color, texture, and bespoke detail throughout. The main residence offers 7 bedrooms and 6 full baths, anchored by five fireplac

$7,950,000

9 beds8.5 baths8,188 sq ft

16 East Trl, Darien, CT 06820

2.89 acre lot • 3 garage spots • Pool

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Investor Alert! Property is in Auction Status - Discover the potential at 11 Division Street in Norwich-a classic two-family home offering a total of 2,130 sq ft of living space. Each spacious unit features 4 rooms, including 2 bedrooms and 1 full bath, spread across 1,065 sq ft per floor. This property is a full renovation project, ideal for contractors or buyers looking to customize and create value. With a convenient location close to downtown amenities, schools, and transportation, this is a prime opportunity to transform a diamond in the rough into a profitable investment or multi-generational home. Bring your vision and tools-Condemned by City of Norwich - No entry - Sold As Is. Find

$46,000

4 beds2 baths2,130 sq ft

11 Division St, Norwich, CT 06360

Two-family home • Convenient location • 7,405 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Historic 1868 South Farms area of Middletown Home with Exceptional Outbuildings Step back in time while enjoying the comfort of modern updates in this distinctive 1868 home, set on a property filled with character, history, and functionality. The home features three bedrooms, 1 1/2 baths, an upstairs office, and a completely remodeled kitchen area. The full-height basement has a granite foundation, poured concrete floor, and floor drains, while an updated electrical box adds peace of mind. The property is framed by magnificent pine trees believed to be among some of the oldest in Middletown, creating a truly memorable setting at the front of the home. The outbuildings offer an exce

$599,900

4 beds1.5 baths2,070 sq ft

110 Freeman Rd, Middletown, CT 06457

3 bay open shed • 6 outbuildings • 1 acre lot

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Rarely does a property of this character and versatility come to market. Welcome to 677 N Salem Road - known historically as the Jamesway Barn Estate - a truly singular 2-acre compound in the heart of Ridgefield that blends 19th-century craftsmanship with extraordinary potential. The main Colonial residence is a diamond in the rough, offering 3 bedrooms, rich wide-plank hardwood floors, two wood-burning fireplaces, and a spacious all-season room - a home that simply awaits the right vision to restore it to its full glory. Original architectural details throughout speak to the craftsmanship of a bygone era. The crown jewel of the property is the historic Jamesway Barn - an awe-inspiring stru

$1,499,000

5 beds3 baths3,168 sq ft

677 N Salem Rd, Ridgefield, CT 06877

40 foot ceilings • All season room • 2 acre compound

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Home with seasonal water views of Holly Pond. Present use: Boarding House. Sold "As Is".

$2,525,000

8 beds3 baths3,443 sq ft

2646 Boston Post Rd, Darien, CT 06820

0.68 acre lot • Garage • Built 1915

Property at 106 Sherland Ave, New Haven, CT 06513, 3 beds, 1.5 baths

$349,900

3 beds1.5 baths1,964 sq ft

106 Sherland Ave, New Haven, CT 06513

Property at 15 Henry St, Greenwich, CT 06830, 2 beds

$799,000

2 beds— baths— sq ft

15 Henry St, Greenwich, CT 06830

Mike Parelli Real Estate LLC

Property at 79 Wesley Ave, Westbrook, CT 06498, 2 beds, 2 baths

$500,000

2 beds2 baths1,320 sq ft

79 Wesley Ave, Westbrook, CT 06498

Property at 567 Roosevelt Dr, Oxford, CT 06478, 2 beds, 1 bath

$390,000

2 beds1 bath1,100 sq ft

567 Roosevelt Dr, Oxford, CT 06478

Property at 18 Overlook Dr, East Haddam, CT 06423, 4 beds, 2 baths

$299,900

4 beds2 baths2,464 sq ft

18 Overlook Dr, East Haddam, CT 06423

Property at 30 Hartford Ave Unit B, Old Lyme, CT 06371, 2 beds, 1 bath

$279,900

2 beds1 bath714 sq ft

30 Hartford Ave Unit B, Old Lyme, CT 06371

Property at 440 Dunbar Hill Rd, Hamden, CT 06514, 3 beds, 2 baths

$458,000

3 beds2 baths2,440 sq ft

440 Dunbar Hill Rd, Hamden, CT 06514

Property at 80-90 Comstock Hill Rd, Norwalk, CT 06850, 6 beds, 5.5 baths

$3,900,000

6 beds5.5 baths25,115 sq ft

80-90 Comstock Hill Rd, Norwalk, CT 06850

Property at 173 Highwoods Dr, Guilford, CT 06437, 5 beds, 7 baths

$1,895,000

5 beds7 baths5,414 sq ft

173 Highwoods Dr, Guilford, CT 06437

Property at 18 Willow Ln, Morris, CT 06763, 2 beds, 1.5 baths

$579,000

2 beds1.5 baths868 sq ft

18 Willow Ln, Morris, CT 06763

Property at 57 Grove St, Clinton, CT 06413, 2 beds, 1 bath

$444,900

2 beds1 bath957 sq ft

57 Grove St, Clinton, CT 06413

Property at 118 Meadow St, Winsted, CT 06098, 3 beds, 2 baths

$259,000

3 beds2 baths1,652 sq ft

118 Meadow St, Winsted, CT 06098

Property at 2222 Ridge Rd, North Haven, CT 06473, 4 beds, 3.5 baths

$899,000

4 beds3.5 baths3,053 sq ft

2222 Ridge Rd, North Haven, CT 06473

Property at 97 North St, Milford, CT 06460, 7 beds, 4.5 baths

$1,175,000

7 beds4.5 baths4,434 sq ft

97 North St, Milford, CT 06460

Property at 203 Spring St, Meriden, CT 06451, 4 beds, 2 baths

$310,000

4 beds2 baths1,848 sq ft

203 Spring St, Meriden, CT 06451

Property at 4 Sherwood Island Ln, Westport, CT 06880, 7 beds, 6.5 baths

$10,500,000

7 beds6.5 baths6,215 sq ft

4 Sherwood Island Ln, Westport, CT 06880

Property at 271 Brown St, West Haven, CT 06516, 3 beds, 2 baths

$365,000

3 beds2 baths1,248 sq ft

271 Brown St, West Haven, CT 06516

Property at 17 High St, Groton, CT 06340, 3 beds, 1.5 baths

$749,900

3 beds1.5 baths1,394 sq ft

17 High St, Groton, CT 06340

Property at 82 Bingham St, Bristol, CT 06010, 3 beds, 1.5 baths

$299,900

3 beds1.5 baths918 sq ft

82 Bingham St, Bristol, CT 06010

Property at 185 Grandview Ave, Bridgeport, CT 06606, 6 beds, 2 baths

$495,000

6 beds2 baths3,108 sq ft

185 Grandview Ave, Bridgeport, CT 06606

Property at 19 Fawn Dr, Woodbridge, CT 06525, 3 beds, 2 baths

$579,000

3 beds2 baths1,450 sq ft

19 Fawn Dr, Woodbridge, CT 06525

Property at 30 Meeting House Ln, Madison, CT 06443, 5 beds, 3.5 baths

$1,695,000

5 beds3.5 baths3,912 sq ft

30 Meeting House Ln, Madison, CT 06443

Property at 133 Chambers Rd, Danbury, CT 06811, 4 beds, 3.5 baths

$745,000

4 beds3.5 baths3,154 sq ft

133 Chambers Rd, Danbury, CT 06811

Property at 1335 Pequot Trl, Stonington, CT 06378, 3 beds, 3.5 baths

$1,350,000

3 beds3.5 baths3,570 sq ft

1335 Pequot Trl, Stonington, CT 06378

Property at 9 Sylvester Ct, Norwalk, CT 06855, 5 beds, 4 baths

$3,295,000

5 beds4 baths4,241 sq ft

9 Sylvester Ct, Norwalk, CT 06855

Property at 5 Shady Knls, Danbury, CT 06811, 3 beds, 4 baths

$3,450,000

3 beds4 baths3,773 sq ft

5 Shady Knls, Danbury, CT 06811

Property at 7 Gravel St #1, Mystic, CT 06355, 3 beds, 2 baths

$1,395,000

3 beds2 baths2,338 sq ft

7 Gravel St #1, Mystic, CT 06355

Property at 124 Richards St, West Haven, CT 06516, 3 beds, 1.5 baths

$349,900

3 beds1.5 baths1,544 sq ft

124 Richards St, West Haven, CT 06516

Property at 94 Second St, Hamden, CT 06514, 3 beds, 1 bath

$300,000

3 beds1 bath1,504 sq ft

94 Second St, Hamden, CT 06514

Property at 259 Ference Rd, Ashford, CT 06278, 3 beds, 2 baths

$239,000

3 beds2 baths3,243 sq ft

259 Ference Rd, Ashford, CT 06278

Property at 11 Cribbins Ave, Shelton, CT 06484, 3 beds, 3 baths

$570,000

3 beds3 baths1,917 sq ft

11 Cribbins Ave, Shelton, CT 06484

Property at 368 Park St, New Britain, CT 06051, 3 beds, 2 baths

$250,000

3 beds2 baths1,380 sq ft

368 Park St, New Britain, CT 06051

Property at 43 Wharton St, West Haven, CT 06516, 3 beds, 1 bath

$320,000

3 beds1 bath1,224 sq ft

43 Wharton St, West Haven, CT 06516

Property at 386 Parker St, Manchester, CT 06042, 4 beds, 2 baths

$499,000

4 beds2 baths1,468 sq ft

386 Parker St, Manchester, CT 06042

Property at 20 Wellers Bridge Rd, Roxbury, CT 06783, 3 beds, 2.5 baths

$725,000

3 beds2.5 baths2,059 sq ft

20 Wellers Bridge Rd, Roxbury, CT 06783

Property at 475 Whitney Ave, New Haven, CT 06511

$2,100,000

— beds— baths7,467 sq ft

475 Whitney Ave, New Haven, CT 06511

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Based on information submitted to the MLS GRID as of Wed Sep 02 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 Connecticut

There are currently 2611 vintage homes for sale in Connecticut. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. This map is refreshed with the newest listings in Connecticut every 15 minutes.

Find your dream vintage homes in Connecticut 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 Connecticut are local experts and are ready to answer your questions about properties , neighborhoods, schools, and the newest listings for sale in Connecticut. If you're looking to sell your home in the Connecticut area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Connecticut with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

Vintage homes for sale & real estate in Connecticut, CT

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