Vintage homes for sale & real estate in Connecticut, CT

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ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Timeless New England charm meets contemporary style in this beautifully remodeled Cape, where classic character and thoughtful modern updates come together effortlessly. The inviting interior features an open-concept kitchen and dining area designed for both everyday living and effortless entertaining. Just off the kitchen, a lovely deck extends the living space outdoors, creating the perfect setting for al fresco dining, relaxed afternoons, and gathering with family and friends. The spacious living room, centered around a wood-burning fireplace, offers warmth and timeless appeal. Two generously sized bedrooms, beautifully updated bathrooms, and California Closets provide comfort and refine

$599,000

2 beds2.5 baths1,390 sq ft

182 Green Hill Rd, Madison, CT 06443

Garage • California closets • Open-concept kitchen

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Classic charm meets everyday convenience in Waterbury's Overlook neighborhood! Just a short stroll away, Fulton Park offers a serene pond, tennis and basketball courts, a baseball field, and a public pool for cooling off on summer days. Shopping, dining, everyday essentials, and highway access are all within easy reach. This 3-bedroom, 1.5-bath Colonial features hardwood floors, a living room with a fireplace, separate dining area, sunroom, partially finished basement, and a walk-up attic for additional storage. The owner is re-staining the hardwood floors to restore their shine and repairing minor driveway cracks. The spacious deck needs some TLC but offers great potential for outdoor gath

$278,000

3 beds1.5 baths1,360 sq ft

71 Clinton St, Waterbury, CT 06710

Serene pond • Highway access • Baseball field

OPEN SUN, 12PM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Looking for land? This home comes with an additional lot. Discover space, character, and room to make it your own at 245 Riverside Street! This inviting four-bedroom Cape offers the convenience of a location close to shopping and local amenities, paired with an expansive outdoor setting. The sale includes the home's . 44-acre lot plus a separate parcel of just over three-quarters of an acre, providing generous space for gardening, outdoor enjoyment, and hobbies. Inside, hardwood floors throughout much of the home add warmth and charm, while a living room, separate dining room, and four upper-level bedrooms provide a versatile layout. The walk-out lower level offers additional space to accom

$288,000

4 beds1.5 baths1,432 sq ft

245 Riverside St, Oakville, CT 06779

Usable outdoor space • Cleared land • Separate parcel

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
-Step back in time and experience the timeless charm of this distinctive antique brick Colonial, set on approximately 3 acres of beautifully cultivated grounds. Blending historic character with thoughtful modern updates, this 3-bedroom, 2-full-bath home offers inviting living spaces, multiple fireplaces, and an exceptional chef's kitchen featuring an oversized island, stone countertops, new appliances, a large basin sink, and a convenient pantry. The kitchen overlooks the spectacular outdoor setting, where nearly 1,100 square feet of newly laid bluestone patio provides the perfect backdrop for entertaining, outdoor dining, or simply enjoying the surrounding gardens. The main level also feat

$469,900

3 beds2 baths2,400 sq ft

15 Chaplin St, Chaplin, CT 06235

Seven apple trees • Oversized island • Three plum trees

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Discover comfort, convenience, and versatility at 20 Pine Street! Situated on a peaceful cul-de-sac, this charming single-level home offers a thoughtfully designed layout, modern updates, and easy access to everyday amenities. Step inside to find updated luxury vinyl tile flooring, a welcoming living room with vaulted ceilings, and an inviting atmosphere perfect for relaxing or entertaining. The refreshed eat-in kitchen features stainless steel appliances, gas cooking, and stylish finishes, while an additional flexible space provides the perfect opportunity for a home office, den, or hobby room. Three generously sized bedrooms and an updated full bathroom with newer fixtures and beadboard d

$270,000

3 beds1 bath1,151 sq ft

20 Pine St, Waterford, CT 06385

Flexible space • Gas cooking • Cul-de-sac

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 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 180 Gardner Ave, New London, CT 06320, 3 beds, 1 bath

$379,900

3 beds1 bath1,240 sq ft

180 Gardner Ave, New London, CT 06320

Property at 67 Nortontown Rd, Madison, CT 06443, 4 beds, 2 baths

$695,000

4 beds2 baths1,956 sq ft

67 Nortontown Rd, Madison, CT 06443

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 71 Reservoir Ave, Meriden, CT 06451, 3 beds, 1.5 baths

$249,900

3 beds1.5 baths1,328 sq ft

71 Reservoir Ave, Meriden, CT 06451

Property at 2 Arthur Rd, East Haven, CT 06512, 3 beds, 1.5 baths

$389,900

3 beds1.5 baths1,142 sq ft

2 Arthur Rd, East Haven, CT 06512

Property at 10 Clearview Dr, Ridgefield, CT 06877, 2 beds, 1 bath

$565,000

2 beds1 bath707 sq ft

10 Clearview Dr, Ridgefield, CT 06877

Property at 41 Florence Ave, New Haven, CT 06512, 3 beds, 2 baths

$397,500

3 beds2 baths1,796 sq ft

41 Florence Ave, New Haven, CT 06512

Property at 26 Calverton Dr, New Fairfield, CT 06812, 3 beds, 1 bath

$399,000

3 beds1 bath1,286 sq ft

26 Calverton Dr, New Fairfield, CT 06812

Property at 14 Dante Pl, Hamden, CT 06514, 3 beds, 1.5 baths

$335,000

3 beds1.5 baths1,376 sq ft

14 Dante Pl, Hamden, CT 06514

Property at 28 Blake St, Ivoryton, CT 06442, 2 beds, 1.5 baths

$389,000

2 beds1.5 baths948 sq ft

28 Blake St, Ivoryton, CT 06442

Property at 200 Damascus Rd, Branford, CT 06405, 4 beds, 2.5 baths

$629,000

4 beds2.5 baths4,087 sq ft

200 Damascus Rd, Branford, CT 06405

Property at 10 Jennifer Rd, Norwalk, CT 06850, 3 beds, 2 baths

$849,000

3 beds2 baths2,426 sq ft

10 Jennifer Rd, Norwalk, CT 06850

Property at 109 Saint Charles Ave, Stamford, CT 06907, 5 beds, 4 baths

$899,999

5 beds4 baths3,718 sq ft

109 Saint Charles Ave, Stamford, CT 06907

Property at 104 Walnut Tree Hill Rd, Shelton, CT 06484, 3 beds, 2 baths

$569,900

3 beds2 baths2,146 sq ft

104 Walnut Tree Hill Rd, Shelton, CT 06484

Property at 5 Hickory Ln, New Milford, CT 06776, 2 beds, 2 baths

$530,000

2 beds2 baths1,567 sq ft

5 Hickory Ln, New Milford, CT 06776

Property at 15-17 Seventh St, Newington, CT 06111, 4 beds, 3 baths

$398,999

4 beds3 baths1,536 sq ft

15-17 Seventh St, Newington, CT 06111

Property at 208 Thornbush Rd, Wethersfield, CT 06109, 3 beds, 1.5 baths

$385,000

3 beds1.5 baths1,488 sq ft

208 Thornbush Rd, Wethersfield, CT 06109

Property at 868 W Main St, West Haven, CT 06516, 2 beds, 1.5 baths

$315,000

2 beds1.5 baths899 sq ft

868 W Main St, West Haven, CT 06516

Property at 108 Strawberry Hill Ave #3, Stamford, CT 06902, 1 bed, 1 bath

$170,000

1 bed1 bath750 sq ft

108 Strawberry Hill Ave #3, Stamford, CT 06902

Property at 52 Anthony Ln, Westbrook, CT 06498, 3 beds, 1.5 baths

$422,377

3 beds1.5 baths914 sq ft

52 Anthony Ln, Westbrook, CT 06498

Property at 45 Broadview Rd, Cheshire, CT 06410, 2 beds, 1 bath

$389,900

2 beds1 bath977 sq ft

45 Broadview Rd, Cheshire, CT 06410

Property at 24 Arrowhead Way, Darien, CT 06820, 5 beds, 8 baths

$6,250,000

5 beds8 baths8,388 sq ft

24 Arrowhead Way, Darien, CT 06820

Property at 141 W Center St, Manchester, CT 06040, 5 beds, 1.5 baths

$232,500

5 beds1.5 baths1,722 sq ft

141 W Center St, Manchester, CT 06040

Property at 260 Nicholson St, Newington, CT 06111, 3 beds, 1.5 baths

$324,900

3 beds1.5 baths1,144 sq ft

260 Nicholson St, Newington, CT 06111

Property at 25 Grand St #249, Norwalk, CT 06851, 2 beds, 1 bath

$375,000

2 beds1 bath1,003 sq ft

25 Grand St #249, Norwalk, CT 06851

Property at 3 Deer Park Rd, Danbury, CT 06811, 4 beds, 4 baths

$899,900

4 beds4 baths4,009 sq ft

3 Deer Park Rd, Danbury, CT 06811

Property at 80 Strong Rd, South Windsor, CT 06074, 4 beds, 2 baths

$399,900

4 beds2 baths1,804 sq ft

80 Strong Rd, South Windsor, CT 06074

Property at 79 Bloomfield Ave, Hartford, CT 06107, 3 beds, 2.5 baths

$675,000

3 beds2.5 baths2,360 sq ft

79 Bloomfield Ave, Hartford, CT 06107

Property at Great Plain Rd, Danbury, CT 06811, 1 bed, 1 bath

$315,000

1 bed1 bath528 sq ft

Great Plain Rd, Danbury, CT 06811

Property at 437 Woodstock Ave, Stratford, CT 06614, 3 beds, 1.5 baths

$469,000

3 beds1.5 baths1,705 sq ft

437 Woodstock Ave, Stratford, CT 06614

Property at 2 Mediterranean Ln, Norwich, CT 06360, 3 beds, 2.5 baths

$294,925

3 beds2.5 baths2,000 sq ft

2 Mediterranean Ln, Norwich, CT 06360

Property at 589 Kent Rd, Gaylordsville, CT 06755, 2 beds, 1.5 baths

$299,900

2 beds1.5 baths1,024 sq ft

589 Kent Rd, Gaylordsville, CT 06755

Property at 55 W Avon Rd, Avon, CT 06001, 4 beds, 3 baths

$715,000

4 beds3 baths2,270 sq ft

55 W Avon Rd, Avon, CT 06001

Property at 225 N Water St, Stonington, CT 06378, 3 beds, 4 baths

$825,000

3 beds4 baths2,458 sq ft

225 N Water St, Stonington, CT 06378

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Based on information submitted to the MLS GRID as of Sat Oct 31 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 3137 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.

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