Vintage homes for sale & real estate in Connecticut, CT

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ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Welcome to 150 Pearl Street! This charming two-story home offers nearly 2,000 square feet of living space, featuring 3 bedrooms, 1.5 bathrooms, and a wonderful blend of character, comfort, and functionality. Freshly painted throughout, the home features beautifully refinished hardwood floors, a fully renovated bathroom, refreshed landscaping, and additional updates waiting to be discovered! Inside, you'll find inviting living spaces, including a cozy living room with a wood-burning stove, perfect for relaxing evenings at home. Additional highlights include central air conditioning, updated electrical, and a flexible floor plan with plenty of room to make it your own. Step outside to enjoy

$419,000

3 beds1.5 baths1,983 sq ft

150 Pearl St, Seymour, CT 06483

Updated electrical • Flexible floor plan • Wood burning stove

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
SPACIOUS 3-FAMILY IN WATERBURY'S NORTH END, CROWNBROOK NEIGHBORHOOD! Offering over 3,100 SF of living space, this substantial multifamily property features three generously sized apartments, each with approximately 1,054 SF, 2 bedrooms, 1 full bath, a large eat-in kitchen, living room and formal dining room. The spacious, functional layouts offer excellent rental appeal, while separate, tenant-paid utilities help keep operating expenses low. Ample off-street parking in the rear adds convenience for tenants. LOCATION HIGHLIGHT = Situated within walking distance of beautiful Fulton Park, offering scenic walking paths, green space and recreational opportunities, with convenient access to shopp

$459,900

6 beds3 baths3,162 sq ft

182 Pearl St, Waterbury, CT 06704

6,534 sq ft lot • 8 parking spots • Built 1925

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Turnkey 3-family offering an excellent opportunity for owner-occupants and investors alike! Each spacious apartment features 2 bedrooms, 1 full bath and approximately 1,140 SF of living space, including a large eat-in kitchen, living room and dining room. Units offer hardwood floors, updated kitchens and bathrooms, and washer/dryer hookups. Exterior improvements include vinyl siding and replacement windows. Separate, tenant-paid electric utilities with no owner's meter help keep operating expenses low. The first-floor unit presents an ideal owner-occupant opportunity, allowing buyers to live in one unit while generating rental income from the others. With minimal maintenance requirements an

$469,900

6 beds3 baths3,443 sq ft

21 Aetna St, Waterbury, CT 06704

Large eat-in kitchen • Updated bathrooms • Vinyl siding

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Don't miss this 3 family gem with city views from the 3rd floor, located on Hill St in Waterbury. This property has been historically income producing but is now vacant for you or your next tenants. Recent updates include kitchens, baths, railings, front porch, hot water heaters and more. The detached 3 car garage is a big plus! Come see for yourself the potential this property brings to the market.

$525,000

5 beds3 baths3,320 sq ft

319 Hill St, Waterbury, CT 06704

Recent updates • City views • Detached garage

OPEN TODAY, 1PM TO 3PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Welcome to 82 Old Mill Road, the perfect balance of privacy and convenience, along with the luxury of an inground pool surrounded by bucolic landscaping. This well-maintained and spacious 3 bed, 2 1/2 bath home is perfectly situated on a secluded acre just steps from Georgetown's restaurants and shops. With almost 2,400 square feet of move-in ready living space, there is room for all. A light-filled and updated eat-in kitchen features new appliances and sliders to the generous backyard patio. Find a welcoming living room with a wood-burning fireplace and picture window, and formal dining room with built-ins. A convenient bedroom and full bath complete the first floor. Upstairs find a genero

$1,049,000

3 beds2.5 baths2,391 sq ft

82 Old Mill Rd, Wilton, CT 06897

Finished basement • Inground pool • 1.08 acre lot

Property at 193 Wheelers Farms Rd, Milford, CT 06461, 5 beds, 2.5 baths

$949,000

5 beds2.5 baths2,340 sq ft

193 Wheelers Farms Rd, Milford, CT 06461

Property at 198 Straitsville Rd, Prospect, CT 06712, 2 beds, 2 baths

$265,000

2 beds2 baths1,684 sq ft

198 Straitsville Rd, Prospect, CT 06712

Property at 151 Brushy Hill Rd, Newtown, CT 06470, 3 beds, 3 baths

$649,000

3 beds3 baths2,549 sq ft

151 Brushy Hill Rd, Newtown, CT 06470

Property at Undisclosed address, Union, CT 06076, 3 beds, 2 baths

$400,000

3 beds2 baths2,492 sq ft

Undisclosed address, Union, CT 06076

Property at 17 Knoll St, Riverside, CT 06878, 4 beds, 3.5 baths

$2,395,000

4 beds3.5 baths2,276 sq ft

17 Knoll St, Riverside, CT 06878

Property at 436 New Haven Ave, Derby, CT 06418, 3 beds, 2 baths

$385,000

3 beds2 baths1,433 sq ft

436 New Haven Ave, Derby, CT 06418

Property at 96 Harpsichord Tpke, Stamford, CT 06903, 4 beds, 4 baths

$2,175,000

4 beds4 baths5,492 sq ft

96 Harpsichord Tpke, Stamford, CT 06903

Property at 157 Mountain Rd, Ridgefield, CT 06877, 2 beds, 2 baths

$649,000

2 beds2 baths972 sq ft

157 Mountain Rd, Ridgefield, CT 06877

Property at 87 Selden Hill Dr, West Hartford, CT 06107, 4 beds, 2 baths

$399,900

4 beds2 baths1,923 sq ft

87 Selden Hill Dr, West Hartford, CT 06107

Property at 58 Muriel Dr, Stamford, CT 06907, 3 beds, 2 baths

$749,000

3 beds2 baths1,360 sq ft

58 Muriel Dr, Stamford, CT 06907

Property at 444 Leetes Island Rd, Guilford, CT 06437, 3 beds, 1.5 baths

$795,000

3 beds1.5 baths1,724 sq ft

444 Leetes Island Rd, Guilford, CT 06437

Property at 374 Flax Hill Rd, Norwalk, CT 06854, 3 beds, 4 baths

$888,927

3 beds4 baths3,577 sq ft

374 Flax Hill Rd, Norwalk, CT 06854

Property at 101 Route 39 S, Sherman, CT 06784, 1 bed, 1 bath

$308,000

1 bed1 bath882 sq ft

101 Route 39 S, Sherman, CT 06784

Property at 1360 Main St, Glastonbury, CT 06033, 4 beds, 2.5 baths

$550,000

4 beds2.5 baths2,215 sq ft

1360 Main St, Glastonbury, CT 06033

Property at 126 Picketts Ridge Rd, Redding, CT 06896, 4 beds, 2.5 baths

$925,000

4 beds2.5 baths2,727 sq ft

126 Picketts Ridge Rd, Redding, CT 06896

Property at 792 Smith Ridge Rd, New Canaan, CT 06840, 2 beds, 3 baths

$1,295,000

2 beds3 baths2,262 sq ft

792 Smith Ridge Rd, New Canaan, CT 06840

Property at 207 Summit St, Willimantic, CT 06226, 3 beds, 2 baths

$329,900

3 beds2 baths2,318 sq ft

207 Summit St, Willimantic, CT 06226

Property at 39 Jaffee Ter, Colchester, CT 06415, 3 beds, 2.5 baths

$260,000

3 beds2.5 baths3,088 sq ft

39 Jaffee Ter, Colchester, CT 06415

Property at 214 Wheeler Rd, Litchfield, CT 06759, 3 beds, 1 bath

$399,900

3 beds1 bath1,239 sq ft

214 Wheeler Rd, Litchfield, CT 06759

Property at 30 Tersana Dr, Easton, CT 06612, 3 beds, 1.5 baths

$500,000

3 beds1.5 baths1,515 sq ft

30 Tersana Dr, Easton, CT 06612

Property at 83 Haynes Rd, West Hartford, CT 06117, 4 beds, 2.5 baths

$515,000

4 beds2.5 baths2,420 sq ft

83 Haynes Rd, West Hartford, CT 06117

Property at 24 Hendrie Drive Extension, Old Greenwich, CT 06870, 5 beds, 5.5 baths

$9,500,000

5 beds5.5 baths5,351 sq ft

24 Hendrie Drive Extension, Old Greenwich, CT 06870

Property at 27 Woodland Rd, Niantic, CT 06357, 3 beds, 2 baths

$419,000

3 beds2 baths1,446 sq ft

27 Woodland Rd, Niantic, CT 06357

Property at 7 Apple Blossom Ln, Danbury, CT 06811, 3 beds, 2 baths

$482,500

3 beds2 baths2,131 sq ft

7 Apple Blossom Ln, Danbury, CT 06811

Property at 8 Beverly Rd, West Hartford, CT 06119, 6 beds, 5 baths

$949,999

6 beds5 baths3,856 sq ft

8 Beverly Rd, West Hartford, CT 06119

Property at 68 Witch Ln, Norwalk, CT 06853, 3 beds, 1.5 baths

$1,250,000

3 beds1.5 baths1,056 sq ft

68 Witch Ln, Norwalk, CT 06853

Property at 695 Forest Rd, West Haven, CT 06516, 4 beds, 2.5 baths

$599,900

4 beds2.5 baths2,302 sq ft

695 Forest Rd, West Haven, CT 06516

Property at 19 Ambler Dr, Norwalk, CT 06851, 3 beds, 2 baths

$685,000

3 beds2 baths1,368 sq ft

19 Ambler Dr, Norwalk, CT 06851

Property at 321 Boston St, Guilford, CT 06437, 4 beds, 3.5 baths

$1,175,000

4 beds3.5 baths3,637 sq ft

321 Boston St, Guilford, CT 06437

Property at 18 Booth Pl, Greenwich, CT 06830, 5 beds, 4 baths

$1,497,000

5 beds4 baths3,091 sq ft

18 Booth Pl, Greenwich, CT 06830

Property at 17 E River Rd, Guilford, CT 06437, 3 beds, 1.5 baths

$749,999

3 beds1.5 baths2,238 sq ft

17 E River Rd, Guilford, CT 06437

Property at 521 W Wolcott Ave, Windsor, CT 06095, 5 beds, 4.5 baths

$385,000

5 beds4.5 baths2,812 sq ft

521 W Wolcott Ave, Windsor, CT 06095

Property at 182 Green Hill Rd, Madison, CT 06443, 2 beds, 2.5 baths

$599,000

2 beds2.5 baths1,390 sq ft

182 Green Hill Rd, Madison, CT 06443

Property at 12 Cedarwood Ln, Shelton, CT 06484, 3 beds, 1.5 baths

$515,000

3 beds1.5 baths1,551 sq ft

12 Cedarwood Ln, Shelton, CT 06484

Property at 71 Clinton St, Waterbury, CT 06710, 3 beds, 1.5 baths

$278,000

3 beds1.5 baths1,360 sq ft

71 Clinton St, Waterbury, CT 06710

Property at 23 Beech Tree Rd, Brookfield, CT 06804, 3 beds, 2.5 baths

$599,900

3 beds2.5 baths2,556 sq ft

23 Beech Tree Rd, Brookfield, CT 06804

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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 3139 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.

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