Vintage homes for sale & real estate in Connecticut, CT

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ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
A character-rich 3-bedroom, 1-bath single-family home nestled in one of Connecticut's most beloved shoreline neighborhoods - Pawson Park. Built in 1920, this home carries the warmth and craftsmanship of early 20th-century New England construction. The interior was designed by Vincent Scully, a Yale Professor and a National Medal of Arts recipient. Three well-proportioned bedrooms offer genuine flexibility for families, remote workers, and anyone who values having room to live comfortably. The kind of home that feels instantly familiar - rooted, honest, and full of potential - on a street where neighbors know each other by name and properties almost never come to market. An exceptional oppor

$649,000

3 beds1 bath1,428 sq ft

207 Pawson Rd, Branford, CT 06405

4,791 sq ft lot • Garage • Built 1920

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ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Location, Location, Location! Walk to vibrant downtown Milford, the Milford Green, restaurants, shops, and the Metro-North train station (0.7 miles) with direct service to New York City from this meticulously renovated 3-bedroom, 2.5-bath Colonial. The inviting main level features beautiful hardwood floors throughout the spacious living room with a cozy fireplace and the formal dining room, creating the perfect setting for everyday living and entertaining. The beautifully designed eat-in kitchen offers quartz countertops, stainless steel appliances, abundant cabinetry, and flows seamlessly to a convenient main-level half bath. Upstairs, you'll find three generously sized bedrooms and two fu

$560,000

3 beds2.5 baths1,476 sq ft

299 W Main St, Milford, CT 06460

Quartz countertops • Eat-in kitchen • Cozy fireplace

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Set within the sought after Lake Forest Association, this charming, stone front cape house offers an exceptional opportunity to enjoy lake living on a generous . 27 acre property. With three bedrooms and 1.5 baths, this home combines timeless character with an easy, functional layout designed for everyday comfort. The expansive backyard extends down towards the lake, creating a peaceful, private setting ideal for outdoor living. A raised deck provides the perfect vantage point overlooking the serene grounds and short walk to the lake. Inside, the living room centers around a cozy fireplace, while the dining room features French doors open to the deck, enhancing the indoor/outdoor connection

$430,000

3 beds1.5 baths1,381 sq ft

555 Lakeside Dr, Bridgeport, CT 06606

Lakefront living • Recent updates • French doors

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Welcome to this classic Colonial-style home in New Britain, Connecticut, offering timeless charm, functional space, and an elevated setting with scenic valley views. Perched atop a hill, this property provides a peaceful backdrop while remaining conveniently located near local amenities, shopping, dining, parks, and major commuting routes. Inside, you'll find a well-designed layout with comfortable living spaces and plenty of room to make it your own. A spacious two-car detached garage offers exceptional storage for vehicles, tools, hobbies, or seasonal items. The full walk-in basement provides even more versatile space with ample storage potential, making organization easy. Whether you're

$300,000

3 beds2 baths1,674 sq ft

136 Sexton St, New Britain, CT 06051

Versatile space • Colonial style home • Well-designed layout

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Highly sought after and rarely available-until now! 89-2 Cottage Road is the seasonal Madison cottage you'll want to run toward. Proudly part of the historic Little Colony community settled by veterans just after World War II, this lovely abode offers two bedrooms and a thoughtfully renovated full bath. The heart of the home is a generous, open-concept living space featuring a beautifully updated kitchen with granite countertops and a center island with a waterfall edge. Outfitted with newer appliances, new flooring throughout, and professional landscaping outside, each upgrade was carefully chosen to cultivate a beautiful yet serene space-easy to maintain, even easier to enjoy! Plus, the f

$335,000

2 beds1 bath764 sq ft

89-2 Cottage Rd, Madison, CT 06443

Full basement • Updated kitchen • 2,178 sq ft lot

Property at 311 Mountain Rd, Wilton, CT 06897, 4 beds, 3 baths

$1,085,000

4 beds3 baths3,300 sq ft

311 Mountain Rd, Wilton, CT 06897

Property at 373 Lake Rd, Warren, CT 06777, 5 beds, 2 baths

$2,200,000

5 beds2 baths2,592 sq ft

373 Lake Rd, Warren, CT 06777

Property at 110 Ruby Ln, Stratford, CT 06614, 3 beds, 1.5 baths

$480,000

3 beds1.5 baths1,548 sq ft

110 Ruby Ln, Stratford, CT 06614

Property at 44 Miamis Rd, West Hartford, CT 06117, 6 beds, 4.5 baths

$785,000

6 beds4.5 baths3,558 sq ft

44 Miamis Rd, West Hartford, CT 06117

Property at 5 Tod Rd, Norwalk, CT 06851, 4 beds, 2 baths

$869,000

4 beds2 baths1,619 sq ft

5 Tod Rd, Norwalk, CT 06851

Property at 9 Wood Ave, Milford, CT 06460, 1 bed, 2 baths

$469,000

1 bed2 baths742 sq ft

9 Wood Ave, Milford, CT 06460

Property at 149 Liberty St, Clinton, CT 06413, 3 beds, 2 baths

$479,900

3 beds2 baths1,520 sq ft

149 Liberty St, Clinton, CT 06413

Property at 219 Hillside Ave, Naugatuck, CT 06770, 6 beds, 3.5 baths

$761,000

6 beds3.5 baths3,930 sq ft

219 Hillside Ave, Naugatuck, CT 06770

Property at 4 Bradley St, Westport, CT 06880, 5 beds, 4 baths

$2,997,000

5 beds4 baths3,255 sq ft

4 Bradley St, Westport, CT 06880

Property at 15 Muriel Dr, Stamford, CT 06907, 3 beds, 1 bath

$725,000

3 beds1 bath1,448 sq ft

15 Muriel Dr, Stamford, CT 06907

Property at 383 Center St, Manchester, CT 06040, 3 beds, 1.5 baths

$284,000

3 beds1.5 baths1,506 sq ft

383 Center St, Manchester, CT 06040

Property at 128 Holmes Rd, Pomfret Center, CT 06259, 4 beds, 3 baths

$545,000

4 beds3 baths2,893 sq ft

128 Holmes Rd, Pomfret Center, CT 06259

Property at 92 Pine St, Columbia, CT 06237, 3 beds, 1 bath

$299,000

3 beds1 bath1,220 sq ft

92 Pine St, Columbia, CT 06237

Property at 56 Evergreen Ave, New London, CT 06320, 3 beds, 1 bath

$305,000

3 beds1 bath1,232 sq ft

56 Evergreen Ave, New London, CT 06320

Property at 40 Rolling Ridge Rd, Orange, CT 06477, 4 beds, 2.5 baths

$680,000

4 beds2.5 baths2,948 sq ft

40 Rolling Ridge Rd, Orange, CT 06477

Property at 11 Route 7 N, Falls Village, CT 06031, 3 beds, 2.5 baths

$595,000

3 beds2.5 baths2,069 sq ft

11 Route 7 N, Falls Village, CT 06031

Property at 370 Calf Pen Ln, Milford, CT 06460, 4 beds, 3 baths

$649,900

4 beds3 baths2,882 sq ft

370 Calf Pen Ln, Milford, CT 06460

Property at 150 Sherman Ct #150, Fairfield, CT 06824, 3 beds, 2.5 baths

$1,089,000

3 beds2.5 baths1,738 sq ft

150 Sherman Ct #150, Fairfield, CT 06824

Property at 3 Stone Ct, Gales Ferry, CT 06335, 3 beds, 1 bath

$299,000

3 beds1 bath1,523 sq ft

3 Stone Ct, Gales Ferry, CT 06335

Property at 47 W Granby Rd, Granby, CT 06035, 1 bed, 1 bath

$339,900

1 bed1 bath696 sq ft

47 W Granby Rd, Granby, CT 06035

Property at 55 Gavitt Rd, Barkhamsted, CT 06063, 3 beds, 1.5 baths

$419,000

3 beds1.5 baths2,104 sq ft

55 Gavitt Rd, Barkhamsted, CT 06063

Property at 1553 Glasgo Rd, Griswold, CT 06351, 6 beds, 3 baths

$425,000

6 beds3 baths5,980 sq ft

1553 Glasgo Rd, Griswold, CT 06351

Property at 40 Mills Ave, Milford, CT 06460, 3 beds, 2 baths

$595,000

3 beds2 baths1,622 sq ft

40 Mills Ave, Milford, CT 06460

Property at 104 Cherniske Rd, New Milford, CT 06776, 2 beds, 1.5 baths

$675,000

2 beds1.5 baths1,236 sq ft

104 Cherniske Rd, New Milford, CT 06776

Property at 18 Chatham Dr, Norwalk, CT 06854, 3 beds, 1.5 baths

$599,900

3 beds1.5 baths1,242 sq ft

18 Chatham Dr, Norwalk, CT 06854

Property at 46 S Stonehedge Drive South, Greenwich, CT 06831, 3 beds, 3.5 baths

$3,895,000

3 beds3.5 baths3,200 sq ft

46 S Stonehedge Drive South, Greenwich, CT 06831

Property at 57 Revonah Ave, Stamford, CT 06905, 5 beds, 3.5 baths

$1,499,000

5 beds3.5 baths2,629 sq ft

57 Revonah Ave, Stamford, CT 06905

Property at 267 Newtown Tpke, Weston, CT 06883, 3 beds, 2.5 baths

$949,000

3 beds2.5 baths2,026 sq ft

267 Newtown Tpke, Weston, CT 06883

Property at 18 Summit Rd, Vernon, CT 06066, 4 beds, 3 baths

$285,000

4 beds3 baths2,426 sq ft

18 Summit Rd, Vernon, CT 06066

Property at 40 River Ave, Norwich, CT 06360, 3 beds, 2 baths

$242,500

3 beds2 baths2,435 sq ft

40 River Ave, Norwich, CT 06360

Property at 61 Cheshire Rd, Wallingford, CT 06492, 2 beds, 1 bath

$384,900

2 beds1 bath1,036 sq ft

61 Cheshire Rd, Wallingford, CT 06492

Property at 42 Academy St #2, New Haven, CT 06511, 2 beds, 2 baths

$595,000

2 beds2 baths1,524 sq ft

42 Academy St #2, New Haven, CT 06511

Property at 662 Coleman Rd, Cheshire, CT 06410, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths3,143 sq ft

662 Coleman Rd, Cheshire, CT 06410

Property at 10 Middle Ln, Simsbury, CT 06070, 3 beds, 1.5 baths

$300,000

3 beds1.5 baths950 sq ft

10 Middle Ln, Simsbury, CT 06070

Property at 397 Christian St, Bridgewater, CT 06752, 4 beds, 3.5 baths

$1,795,000

4 beds3.5 baths2,929 sq ft

397 Christian St, Bridgewater, CT 06752

Property at 1797 Middletown Ave, Northford, CT 06472, 3 beds, 2 baths

$549,900

3 beds2 baths2,464 sq ft

1797 Middletown Ave, Northford, CT 06472

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Based on information submitted to the MLS GRID as of Tue Sep 01 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 2602 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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