Vintage homes for sale & real estate in New Haven County, CT

535 homes

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NEW 4 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in New Haven County, CT:
This expansive family home offers exceptional space where size truly is not an issue. A beautiful front porch welcomes you in, perfect for morning coffee or evening relaxation, and leads to a grand staircase that sets the tone for the home's classic character. Enjoy a generously sized dining room, a large family room anchored by a fireplace, and a bright sunroom just off the living room, ideal for relaxing or entertaining year-round. The home has been freshly painted and features updated bathrooms, blending comfort with timeless appeal. On street parking is complemented by a garage for added convenience. Make this house your home just in time for the holidays there's plenty of room to gathe

$284,000

4 beds3 baths2,436 sq ft

38 Kellogg St, Waterbury, CT 06710

Grand staircase • Front porch • Family room

NEW 3 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in New Haven County, CT:
Stunning Colonial-style home that has been exceptionally well-maintained, showcasing pride of ownership throughout. This elegant residence offers 3 bedrooms, a super spacious living room, and a formal separate dining room ideal for both refined entertaining and everyday comfort. Recent updgrades include newer windows and a roof approximately 10 years old, adding value and peace of mind. The expansive basement offers excellent potential for an in-law setup (Buyer to do diligence). Schedule your appointment!

$350,000

3 beds2 baths2,336 sq ft

27 Woolsey St, New Haven, CT 06513

Newer windows • Expansive basement • Well-maintained

NEW 4 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in New Haven County, CT:
Legal 3-family featuring three (3) 3-bedroom units. Fully renovated and turnkey, with brand-new electrical, plumbing, and sewer, plus new furnaces and appliances throughout. Bright layouts, hardwood floors, and updated bathrooms in each unit. Strong rental demand for 3-bedroom units offers excellent income potential with minimal maintenance. Conveniently located near downtown New Haven, Yale, hospitals, and public transportation.

$525,000

9 beds3 baths3,130 sq ft

52 Ann St, New Haven, CT 06519

Fully renovated • Brand-new plumbing • New appliances

NEW 5 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in New Haven County, CT:
Well-maintained two-family home located on a quiet residential street in New Haven. This property offers two separate units with functional layouts, providing an excellent opportunity for owner-occupants or investors. Each unit features spacious living areas with ample natural light and comfortable room configurations. The home is conveniently situated near local amenities, public transportation, shopping, dining, and major highways, allowing for easy access throughout the city and surrounding areas. A solid multi-family option with strong potential in a desirable New Haven location.

$360,000

5 beds2 baths2,795 sq ft

46 Arthur St, New Haven, CT 06519

Ample natural light • Two separate units • Two family home

NEW 4 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in New Haven County, CT:
CASH-FLOWING MULTI-FAMILY OPPORTUNITY IN THE HEART OF Seymour!!! Welcome to 53-55 Maple Street, a solid income-producing multi-family property perfectly positioned for both savvy investors and owner-occupants looking to offset their mortgage. This well-maintained asset offers strong rental potential, long-term upside, and immediate cash flow in a high-demand rental market. Market area rent between $1,800-$2,400; the garage was previously rented for $250/month. Each unit has 3 bedrooms and 1-bath (plus additional rooms), separate utilities, and abundant natural light, making it highly attractive to tenants. Both units have been newly painted; unit 53 has a new propane tank and new floors. Bo

$480,000

6 beds2 baths2,026 sq ft

53 Maple St, Seymour, CT 06483

Newly painted • 0.32 acre lot • Built 1900

Property at 28 Hill St, Waterbury, CT 06704, 15 beds, 5 baths

$899,900

15 beds5 baths6,525 sq ft

28 Hill St, Waterbury, CT 06704

Property at 124 Windsor Ave, Meriden, CT 06451, 4 beds, 2 baths

$360,000

4 beds2 baths2,040 sq ft

124 Windsor Ave, Meriden, CT 06451

Property at 443 Todd Rd, Wolcott, CT 06716, 3 beds, 2 baths

$449,999

3 beds2 baths2,147 sq ft

443 Todd Rd, Wolcott, CT 06716

Property at 185 Springdale Ave, Meriden, CT 06451, 3 beds, 2 baths

$289,000

3 beds2 baths1,320 sq ft

185 Springdale Ave, Meriden, CT 06451

Property at 87 Melrose Ave, Waterbury, CT 06705, 3 beds, 1 bath

$339,999

3 beds1 bath1,545 sq ft

87 Melrose Ave, Waterbury, CT 06705

Property at 621 Wiese Rd, Cheshire, CT 06410, 3 beds, 2 baths

$535,000

3 beds2 baths1,704 sq ft

621 Wiese Rd, Cheshire, CT 06410

Property at 24 Railroad Ave, Madison, CT 06443, 2 beds, 1.5 baths

$475,000

2 beds1.5 baths1,000 sq ft

24 Railroad Ave, Madison, CT 06443

Property at 193 Waterville St, Waterbury, CT 06710, 3 beds, 1 bath

$264,900

3 beds1 bath1,332 sq ft

193 Waterville St, Waterbury, CT 06710

Property at 84 Eileen Rd, West Haven, CT 06516, 3 beds, 1.5 baths

$429,900

3 beds1.5 baths1,945 sq ft

84 Eileen Rd, West Haven, CT 06516

Property at 24 Forest St, Naugatuck, CT 06770, 3 beds, 1 bath

$355,000

3 beds1 bath1,757 sq ft

24 Forest St, Naugatuck, CT 06770

Property at 24 Yates St, West Haven, CT 06516, 2 beds, 1.5 baths

$284,900

2 beds1.5 baths1,220 sq ft

24 Yates St, West Haven, CT 06516

Property at 82 Hemlock St, West Haven, CT 06516, 4 beds, 2 baths

$487,700

4 beds2 baths992 sq ft

82 Hemlock St, West Haven, CT 06516

Property at 58 Cowles St, Milford, CT 06461, 3 beds, 1.5 baths

$464,900

3 beds1.5 baths1,816 sq ft

58 Cowles St, Milford, CT 06461

Property at 9 Milton Dr, Meriden, CT 06450, 3 beds, 1.5 baths

$284,900

3 beds1.5 baths1,092 sq ft

9 Milton Dr, Meriden, CT 06450

Property at 87 Orchard St, New Haven, CT 06519, 4 beds, 2 baths

$350,000

4 beds2 baths2,088 sq ft

87 Orchard St, New Haven, CT 06519

Property at 253 Chatham St, New Haven, CT 06513, 8 beds, 3 baths

$499,900

8 beds3 baths3,579 sq ft

253 Chatham St, New Haven, CT 06513

Property at 1002 Winchester Ave, Hamden, CT 06517, 3 beds, 1.5 baths

$299,999

3 beds1.5 baths1,920 sq ft

1002 Winchester Ave, Hamden, CT 06517

Property at 2603 N Main St, Waterbury, CT 06704, 2 beds, 1 bath

$309,000

2 beds1 bath1,654 sq ft

2603 N Main St, Waterbury, CT 06704

Property at 219 Court St, West Haven, CT 06516, 4 beds, 2 baths

$469,925

4 beds2 baths2,540 sq ft

219 Court St, West Haven, CT 06516

Property at 80 Concord St, Waterbury, CT 06710, 3 beds, 1 bath

$249,900

3 beds1 bath1,460 sq ft

80 Concord St, Waterbury, CT 06710

Property at 39 Cedar Ln, Cheshire, CT 06410, 2 beds, 1 bath

$384,900

2 beds1 bath1,086 sq ft

39 Cedar Ln, Cheshire, CT 06410

Property at 80 Cliff St, Naugatuck, CT 06770, 3 beds, 1.5 baths

$327,900

3 beds1.5 baths1,427 sq ft

80 Cliff St, Naugatuck, CT 06770

Property at 55 Prospect Ave, West Haven, CT 06516, 4 beds, 2.5 baths

$389,900

4 beds2.5 baths4,164 sq ft

55 Prospect Ave, West Haven, CT 06516

Property at 30 Melrose Ave, Waterbury, CT 06705, 3 beds, 2 baths

$335,000

3 beds2 baths1,304 sq ft

30 Melrose Ave, Waterbury, CT 06705

Property at 4 N Spring St, Ansonia, CT 06401, 3 beds, 2 baths

$359,900

3 beds2 baths1,342 sq ft

4 N Spring St, Ansonia, CT 06401

Property at 284 Chestnut Tree Hill Rd, Oxford, CT 06478, 3 beds, 2 baths

$649,900

3 beds2 baths1,812 sq ft

284 Chestnut Tree Hill Rd, Oxford, CT 06478

Property at 131 Wallingford Rd, Cheshire, CT 06410, 3 beds, 2 baths

$335,000

3 beds2 baths1,180 sq ft

131 Wallingford Rd, Cheshire, CT 06410

Property at 102 Surf Ave, Milford, CT 06460, 2 beds, 1 bath

$419,000

2 beds1 bath1,591 sq ft

102 Surf Ave, Milford, CT 06460

Property at 2 Treadwell St, West Haven, CT 06516, 3 beds, 1 bath

$425,000

3 beds1 bath1,640 sq ft

2 Treadwell St, West Haven, CT 06516

Property at 897 First Ave, West Haven, CT 06516, 3 beds, 1 bath

$290,000

3 beds1 bath1,080 sq ft

897 First Ave, West Haven, CT 06516

Property at 67 Clover St, Waterbury, CT 06706, 3 beds, 1.5 baths

$250,000

3 beds1.5 baths1,182 sq ft

67 Clover St, Waterbury, CT 06706

Property at 143 Birch St, Waterbury, CT 06704, 3 beds, 1.5 baths

$265,000

3 beds1.5 baths1,407 sq ft

143 Birch St, Waterbury, CT 06704

Property at 102 Chestnut St, West Haven, CT 06516, 2 beds, 1.5 baths

$369,000

2 beds1.5 baths1,564 sq ft

102 Chestnut St, West Haven, CT 06516

Property at 35 Fairchild St, Naugatuck, CT 06770, 4 beds, 2.5 baths

$379,000

4 beds2.5 baths2,028 sq ft

35 Fairchild St, Naugatuck, CT 06770

Property at 181 Sunset Dr, Ansonia, CT 06401, 2 beds, 1 bath

$329,900

2 beds1 bath1,116 sq ft

181 Sunset Dr, Ansonia, CT 06401

Property at 247 Fairmont Ave, New Haven, CT 06513, 3 beds, 1 bath

$329,900

3 beds1 bath1,081 sq ft

247 Fairmont Ave, New Haven, CT 06513

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Based on information submitted to the MLS GRID as of Tue Dec 23 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 New Haven County

There are currently 535 vintage homes for sale in New Haven County at a median listing price of $399K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in New Haven County stay on the market for 55 days and receive 1 offers. This map is refreshed with the newest listings in New Haven County every 15 minutes.

In the past month, 648 homes have been sold in New Haven County. In addition to houses in New Haven County, there were also 628 condos, 1 townhouse, and 284 multi-family units for sale in New Haven County last month. Find your dream home in New Haven 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 New Haven County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in New Haven County. If you're looking to sell your home in the New Haven County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in New Haven 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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