Vintage homes for sale & real estate in Madison, CT

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ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Step into a story nearly three centuries in the making. Tucked away on a total of 3 enchanting acres along Connecticut's picturesque shoreline, this extraordinary circa-1752 former Helen Foster Snow homestead is a place where history whispers through every room and timeless beauty meets modern living. Ideally located just minutes from the area's scenic shoreline destinations, including Hammonasset Beach State Park (~5 miles) and the Surf Club Beach (~4 miles), this exceptional property offers the rare combination of historic charm, privacy, and coastal living. Once home to the renowned journalist, author, and humanitarian, the property carries a remarkable legacy while inviting its next ste

$1,200,000

4 beds4 baths2,354 sq ft

Two classic barns • Peaceful pond • Developable lot

148 Mungertown Rd, Madison, CT 06443

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
BEACH HOME! BEACH RIGHTS! NEEDS WORK! It is not everyday that an opportunity to own a double lot in such a shoreline area. This charming English Cottage-style Cape, situated on a generous footprint for the area, is ready for it's next chapter-whether that involves a thoughtful renovation or the construction of a brand-new coastal home perhaps. Residents enjoy deeded rights to a private association sandy beach located just at the end of the street! The main residence of which there are no photos for obvious reasons once you see it (NEEDS WORK) currently features three bedrooms and 1.5 baths but adding to the property's versatility is a delightful in good condition accessory apartment, which

$700,000

3 beds2.5 baths2,124 sq ft

Beach rights • Full kitchen • Deeded rights

67 Blakeman Rd, Madison, CT 06443

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Escape to the Connecticut shoreline with this beautifully styled Cape, ideally situated in desirable Madison. Offering 3 bedrooms and 1 full bath, this charming home features inviting indoor and outdoor living spaces designed for comfortable everyday living and relaxed coastal living. Set on a private, lightly wooded corner lot, the property offers a peaceful sense of privacy while remaining close to everything Madison has to offer. Recent improvements include new cedar siding, windows throughout with custom window treatments, propane fireplace installation, and professional interior painting, all completed in 2025. The roof and septic system were both replaced in 2022. Just a 5-minute dri

$579,900

3 beds1 bath1,077 sq ft

New cedar siding • Roof replaced • 1.03 acre lot

6 Bower Rd, Madison, CT 06443

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Enjoy the best the shoreline has to offer in this charming seasonal summer cottage. Bring your swimsuits, sunscreen, and a book. .. and move right into this furnished, turnkey summer house. One of the largest cottages, this home has central air, 2-3 parking spaces, and a lovely lot. Sun-filled, airy, and spacious, with a large kitchen and dining room, a generous living room, and 2 additional rooms. Listed as a 1-bedroom, but could easily be used as 2 bedrooms, or 1 bedroom and a flex room. The half bath even has an all-in-one washer/dryer unit. You'll love the outdoor shower, fresh air, under the stars, no sand in the house. Outside is a large storage shed and a screened gazebo, perfect for

$210,000

1 bed0.5 baths732 sq ft

Large kitchen • Dining room • Generous living room

40 East St, Madison, CT 06443

ABOUT THIS HOME
Vintage Home for sale in Madison, 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

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

89-2 Cottage Rd, Madison, CT 06443

Property at 66 Wildcat Rd, Madison, CT 06443, 2 beds, 1 bath

$349,900

2 beds1 bath625 sq ft

66 Wildcat Rd, Madison, CT 06443

Property at 118 River Rd, Madison, CT 06443, 3 beds, 3 baths

$5,000,000

3 beds3 baths3,109 sq ft

118 River Rd, Madison, CT 06443

Property at 17 Barberry Ln, Madison, CT 06443, 4 beds, 5 baths

$3,000,000

4 beds5 baths4,833 sq ft

17 Barberry Ln, Madison, CT 06443

Property at 2415 Durham Rd, Madison, CT 06443, 2 beds, 1.5 baths

$880,000

2 beds1.5 baths1,795 sq ft

2415 Durham Rd, Madison, CT 06443

Property at 16 North St, Madison, CT 06443, 1 bed, 1 bath

$138,000

1 bed1 bath476 sq ft

16 North St, Madison, CT 06443

Property at 32 Liberty St, Madison, CT 06443, 3 beds, 3 baths

$1,299,000

3 beds3 baths1,188 sq ft

32 Liberty St, Madison, CT 06443

Property at 26 Bassett Ln, Madison, CT 06443, 3 beds, 3.5 baths

$1,950,000

3 beds3.5 baths2,160 sq ft

26 Bassett Ln, Madison, CT 06443

Property at 92 Fourth Ave, Madison, CT 06443, 2 beds, 1 bath

$142,900

2 beds1 bath396 sq ft

92 Fourth Ave, Madison, CT 06443

Property at 1209 Durham Rd, Madison, CT 06443, 5 beds, 5.5 baths

$1,200,000

5 beds5.5 baths3,832 sq ft

1209 Durham Rd, Madison, CT 06443

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 32 North St, Madison, CT 06443, 2 beds, 1 bath

$149,900

2 beds1 bath592 sq ft

32 North St, Madison, CT 06443

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NEW 6 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Welcome to 882 Killingworth Road, a beautifully updated 4-bedroom, 3-bath Colonial set on two private acres in the heart of Haddam. Offering over 2,200 sq ft of living space, this home blends classic New England charm with modern updates, including refinished hardwood floors and a bright, open layout ideal for everyday living and entertaining. The well appointed kitchen flows seamlessly into the dining and living areas, with sliding glass doors leading to a newly installed stone patio overlooking the in-ground pool and expansive yard. A standout main level primary suite features a walk in shower, tile flooring, in-suite laundry, and a spacious walk in closet. Upstairs, three additional bedr

$620,000

4 beds3 baths2,286 sq ft

In-ground pool • Open layout • Updated colonial

882 Killingworth Rd, Higganum, CT 06441

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Historic 1856 Octagon Home Just One Block from the Iconic Guilford Green. Rarely does a home of such architectural distinction and prime location become available. Crafted in 1859 by renowned local builder Edwin A. Leete, this landmark 4-bedroom, 2.5-bath octagonal residence offers a extraordinary blend of mid-19th-century character and seamless modern comfort-all just a single block from the historic Guilford Green. Inside, the distinctive eight-sided floor plan fills the home with exceptional natural light across a generous layout featuring a formal Living Room, dedicated Dining Room, and cozy Family Room. At the heart of the home is a chef-inspired, high-end custom Gulick Kitchen, beauti

$1,125,000

4 beds2.5 baths2,254 sq ft

Flat fenced lot • Prime location • Detached garage

84 Fair St, Guilford, CT 06437

OPEN SAT, 10AM TO 1:30PM

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Imagine strolling to the historic Guilford Green, with downtown shops, dining, and the train station just steps away! Situated on a level 0.68-acre lot, this turnkey 1920 Craftsman at 134 Union perfectly marries vintage soul with effortless modern living. A reclaimed wood ceiling warms the foyer, leading into an open-concept entertainer's dream. The chef's kitchen boasts sweeping quartz counters, a massive island, farmhouse sink, double ovens, and geometric tile. The dining room easily seats ten and flows into a cozy living room. Flawless red oak floors tie the 2,194 sq ft main living space together. Your main-level primary suite features a walk-in closet, reclaimed wood accent wall, and a

$949,000

4 beds2.5 baths2,194 sq ft

Massive island • Farmhouse sink • Level 0.68-acre lot

134 Union St, Guilford, CT 06437

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Welcome to 36 Waterside Lane, a unique historic home located steps from Clinton Town Beach. With its four bedrooms, six fireplaces, wide-plank floors, exposed beams, and original window sashes, this home exudes character throughout. The layout is generous and flexible - studios, libraries, guest quarters, laundry room, walk-in pantry, home offices - without losing the bones that make this place what it is. There is an unmistakable sense of craftsmanship here that no newly constructed residence can reproduce. A detached two-car garage equipped with built-in workbenches, pegboard walls, oversized shelving and 780sq feet of work area provides ample space for an artist's studio, pottery shed, c

$850,000

4 beds1.5 baths2,608 sq ft

Six fireplaces • Exposed beams • Wide plank floors

36 Waterside Ln, Clinton, CT 06413

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Welcome to 100 N Tower Hill Road! This spacious 5-bedroom, 2-bath Colonial is set on 3.6 private acres in desirable Killingworth. Major updates include new windows, a new boiler, new septic system, new carpeting throughout, and fresh interior paint. With over 2,000 square feet, the home offers generous living space, a 2-car garage, and a peaceful country setting. Enjoy the privacy and charm of Killingworth with many major improvements already completed. Don't miss this opportunity!

$599,000

5 beds2 baths2,090 sq ft

Private acres • New boiler • New carpeting

100 N Tower Hill Rd, Killingworth, CT 06419

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
13-Acre Secluded Country Oasis nestled in the beautiful Connecticut countryside, offering privacy and an extraordinary connection to nature. Set on a lovely pond with a dock ideal for kayaks, canoes or a rowboat, the property features a gorgeous waterfall cascading into the Ponset Brook. It is truly like living inside a postcard with nature and tranquility. The charming 8-room home features beautiful hardwood floors and inviting spaces throughout. A spectacular oversized office boasts a wall of windows overlooking the waterfall and a second wall lined with built-in bookcases-an inspiring setting for work, reading or simply enjoying the ever-changing beauty of nature. A portion of the home w

$840,000

2 beds2 baths2,454 sq ft

Lovely pond • Large barn • Gorgeous waterfall

33 Little City Rd, Higganum, CT 06441

Property at 11 Autumn Ln, Clinton, CT 06413, 3 beds, 2 baths

$639,000

3 beds2 baths2,508 sq ft

11 Autumn Ln, Clinton, CT 06413

Property at 137 Parmelee Hill Rd, Durham, CT 06422, 4 beds, 2 baths

$424,900

4 beds2 baths2,479 sq ft

137 Parmelee Hill Rd, Durham, CT 06422

Property at 38 Little City Rd, Killingworth, CT 06419, 3 beds, 1 bath

$359,000

3 beds1 bath1,082 sq ft

38 Little City Rd, Killingworth, CT 06419

Property at 4 Pine Pl, Clinton, CT 06413, 4 beds, 2 baths

$699,900

4 beds2 baths1,833 sq ft

4 Pine Pl, Clinton, CT 06413

Property at 18 Fair St #3, Guilford, CT 06437, 2 beds, 2.5 baths

$950,000

2 beds2.5 baths1,816 sq ft

18 Fair St #3, Guilford, CT 06437

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 165 Whitfield St, Guilford, CT 06437, 2 beds, 2.5 baths

$825,000

2 beds2.5 baths2,595 sq ft

165 Whitfield St, Guilford, CT 06437

Property at 234 Airline Rd, Clinton, CT 06413, 3 beds, 1.5 baths

$469,900

3 beds1.5 baths1,496 sq ft

234 Airline Rd, Clinton, CT 06413

Property at 110 East Main St, Clinton, CT 06413, 3 beds, 1.5 baths

$190,000

3 beds1.5 baths1,238 sq ft

110 East Main St, Clinton, CT 06413

Property at 33 Church St, Guilford, CT 06437, 6 beds, 3 baths

$1,185,000

6 beds3 baths3,833 sq ft

33 Church St, Guilford, CT 06437

Property at 100 Pratt Rd, Clinton, CT 06413, 3 beds, 2 baths

$525,000

3 beds2 baths1,296 sq ft

100 Pratt Rd, Clinton, CT 06413

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 511 Route 81, Killingworth, CT 06419, 2 beds, 2 baths

$699,000

2 beds2 baths1,386 sq ft

511 Route 81, Killingworth, CT 06419

Property at 180 Green Hill Rd, Killingworth, CT 06419, 4 beds, 4 baths

$1,299,900

4 beds4 baths4,154 sq ft

180 Green Hill Rd, Killingworth, CT 06419

Vintage Homes for Sale in Madison

There are currently 16 vintage homes for sale in Madison at a median listing price of $709K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Madison stay on the market for 47 days and receive 4 offers. This map is refreshed with the newest listings in Madison every 15 minutes.

In the past month, 31 homes have been sold in Madison. In addition to houses in Madison, there were also 16 condos, 0 townhouses, and 1 multi-family unit for sale in Madison last month. Find your dream home in Madison 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 Madison are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Madison. If you're looking to sell your home in the Madison area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Madison with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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