Vintage homes for sale & real estate in Madison, CT

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COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Coming Soon in Madison! Available for showings on 12-15-25! Professional Pics and more information will be loaded soon. Stellar location! Just 1 mile from the historic Town Green. Easy access: 1.4 miles to the Madison Surf Club and Train Station, plus close proximity to schools (including the brand new Neck River Elementary) and the picturesque Bauer Park. This 3 bedroom, ONE LEVEL living home with newer appliances is set on nearly an acre of beautifully landscaped grounds creating privacy (with a fenced in yard for Fido). A gardeners delight! You will have blooms from Spring to Fall with the various, multiple plantings. This home also offers a finished room, including a half bath (plumbed

$540,000

3 beds1.5 baths1,346 sq ft

43 Fort Path Rd, Madison, CT 06443

0.92 acre lot • 2 garage spots • Built 1960

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Ranch-style single-family home situated on 1 acre, just 5 minutes from Hammonasset State Beach. The property features classic New England stone walls surrounding much of the land, along with a detached two-car garage. Inside, has nice looking exposed beams! Then living room, kitchen, three bedrooms, and one bathroom-all on the main floor. Full unfinished basement with an exterior hatch. The property is on well and septic and requires significant renovation throughout, but it has tremendous potential to become a beautiful residence, profitable flip, or solid rental. Home to be sold as is. Final & Best Thursday the 18th 5pm

$325,000

3 beds1 bath1,080 sq ft

42 Wildcat Rd, Madison, CT 06443

Exterior hatch • Ranch-style home • 1 acre

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Great downtown location with beautiful salt marsh views. This lovely 3-bedroom home offers easy living and stunning scenery throughout. The main level includes two bedrooms with a shared full bath, while the private primary suite upstairs features vaulted ceilings, a gas fireplace, full bath, and a balcony overlooking the marsh. The bright living room opens to an oversized deck with serene views and gorgeous sunsets. The vaulted dining room with gas fireplace creates an inviting space for indoor gatherings. The kitchen features granite countertops, a breakfast bar, and appliances including a gas cooktop and double ovens. Ideally situated between Madison Village and the Guilford Green-just m

$549,900

3 beds2 baths2,034 sq ft

90 Boston Post Rd, Madison, CT 06443

Oversized deck • Gas fireplace • Downtown location

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Welcome to 1281 Durham Road in Madison, CT. This beautifully maintained home offers just under 2,200 sq ft of living space and sits on nearly half an acre in a highly desirable neighborhood. The main level features two bedrooms, a spacious living room with a fireplace, a large kitchen, a full bathroom, a laundry room, and a huge bonus room that extends the entire length of the house. The windows throughout this floor bring in an abundance of natural light, creating a warm and inviting atmosphere. Upstairs, you'll find another kitchen, a comfortable living room, two additional bedrooms, a full bathroom, and a private enclosed balcony overlooking the expansive yard. This upper level also rece

$499,900

4 beds2.5 baths2,192 sq ft

1281 Durham Rd, Madison, CT 06443

Expansive yard • 0.48 acre lot • Garage

CLMA Realty

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Welcome home to this picture-perfect ranch in peaceful North Madison-where comfort, charm, and convenience come together beautifully. With just over 1,100 square feet of thoughtfully designed living space, this home offers two bedrooms plus flexible office space, ideal for working from home or creating a cozy guest space. The open floor plan fills the home with natural light and makes everyday living feel easy and connected. The kitchen flows seamlessly into the dining and living areas, where a wood burning fireplace adds warmth, creating the perfect gathering space. Step outside to a beautiful, open backyard-ideal for morning coffee, summer barbecues, or simply soaking in the serenity of n

$435,000

2 beds1.5 baths1,110 sq ft

779 Summer Hill Rd, Madison, CT 06443

0.82 acre lot • Garage • Built 1950

Property at 35 Hotchkiss Ln, Madison, CT 06443, 3 beds, 2.5 baths

$1,695,000

3 beds2.5 baths2,400 sq ft

35 Hotchkiss Ln, Madison, CT 06443

Property at 115 Harbor Ave, Madison, CT 06443, 4 beds, 3 baths

$1,450,000

4 beds3 baths1,999 sq ft

115 Harbor Ave, Madison, CT 06443

Property at 108 Boston Post Rd, Madison, CT 06443, 3 beds, 2 baths

$575,000

3 beds2 baths1,700 sq ft

108 Boston Post Rd, Madison, CT 06443

Property at 153 Middle Beach Rd, Madison, CT 06443, 4 beds, 2 baths

$2,400,000

4 beds2 baths3,083 sq ft

153 Middle Beach Rd, Madison, CT 06443

Property at 141 Duck Hole Rd, Madison, CT 06443, 3 beds, 2 baths

$550,000

3 beds2 baths1,186 sq ft

141 Duck Hole Rd, Madison, CT 06443

Property at 75 Fairview Dr, Madison, CT 06443, 3 beds, 2 baths

$450,000

3 beds2 baths1,419 sq ft

75 Fairview Dr, Madison, CT 06443

Property at 4 North St, Madison, CT 06443, 3 beds, 1 bath

$229,000

3 beds1 bath897 sq ft

4 North St, Madison, CT 06443

Property at 7 Third St, Madison, CT 06443, 1 bed, 1 bath

$164,900

1 bed1 bath441 sq ft

7 Third St, Madison, CT 06443

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NEW 22 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Whether you are looking for a second home or year round living by the water, this is the home for you. Walkable to the town boat dock and 2 restaurants, town beach, train station and vibrant downtown area with shops, restaurants and the prettiest New England green on the shoreline. Perfect for one floor living with two bedrooms and a full bath downstairs and two bedrooms and a full bath upstairs with bonus loft space. First floor has a spacious living room leading to a generous size dining room. There is an ipe deck out the front of the dining room with marsh views. Updated kitchen with Viking gas stove, Nantucket pebble backsplash and black granite. Off the dining room we find a lovely 3 s

$645,000

4 beds2 baths1,559 sq ft

40 Seaview Ter, Guilford, CT 06437

Waterfront community • 0.26 acre lot • Built 1947

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
The home features classic, neutral-toned lap siding that provides a clean, traditional look with neat horizontal lines. This common style offers both durability and low maintenance, presenting a welcoming and well-kept appearance.

$279,000

2 beds1 bath896 sq ft

41 Beaver Meadow Rd, Haddam, CT 06438

1 acre lot • Built 1958 • Listed 2 days

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
LOCATION! LOCATION! LOCATION! Welcome to this beautifully fully remodeled two-family home just steps from the historic Guilford Green. Both units showcase modern finishes featuring new kitchens and bathrooms. The dwelling has also recently been improved with new electrical, plumbing, flooring, fixtures, paint, and septic system. This move-in ready home can offer easy cash flow and is also ideal for owner- occupants looking to live on the Guilford Green and experience all this location has to offer. Don't miss this exceptional opportunity to own a turnkey investment or multi- generational home in pristine condition!

$799,000

4 beds2 baths1,804 sq ft

26 Water St, Guilford, CT 06437

New kitchens • Fully remodeled • New plumbing

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
In the 1720's the back of this house faced the road. In the 2000's the owner had the house lifted, rotated 180 degrees and reset on a new full basement. They spared no effort or expense to retain the rare charm of a true antique home while giving this rare jewel all the conveniences of the 21st Century. Step back in time without sacrificing modern convenience. Built in 1723, this exquisite antique colonial blends rich history with thoughtful updates in a truly one-of-a-kind setting. Featuring 3 bedrooms and 3 full bathrooms, this home showcases wide plank floors, exposed beams, and timeless character throughout-while offering an updated kitchen, central air, a whole house Generac generator,

$650,000

3 beds3 baths3,439 sq ft

4365 Durham Rd, Guilford, CT 06437

4.5 acre lot • 4 parking spots • Built 1723

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Newly remodeled 4 bedroom 3.5 bath Victorian/colonial home walking distance to the Green with sweeping water views of the tidal river, marsh and harbor. Spectacular brand new kitchen with BIG CHILL appliances, granite and soap stone counters, massive island and vaulted ceilings. Hardwood floors throughout. This property also features a two car detached garage with a newly renovated carriage house above the garage that can be used as a rental, guest house or professional office for the homeowner. In addition there is a 2 bedroom four season cottage rental for extra income. Rental income is projected to be in excess of 50k per year for both rear buildings. All mechanicals and roof are brand n

$1,650,000

4 beds2.5 baths2,519 sq ft

201 Water St, Guilford, CT 06437

Massive island • Brand new kitchen • Big chill appliances

ABOUT THIS HOME
Vintage Home for sale in Madison, CT:
Welcome to 106 Glenwood Road - a long-time family home ready for its next chapter. Owned by the same family since it was built in 1950, this 3-bedroom, 2-bath ranch offers a solid footprint and excellent potential in one of Clinton's quiet residential neighborhoods. The home sits on a spacious 0.84-acre lot just minutes from town beaches, local shops, and commuter routes. Inside, you'll find comfortable living areas and a layout suited for everyday life, with opportunities to modernize and make it your own. The large yard provides space for outdoor living, gardening, or expansion possibilities. Enjoy the character of a well-loved home and bring your vision to life in this shoreline communit

$375,000

3 beds2 baths1,402 sq ft

106 Glenwood Rd, Clinton, CT 06413

Large yard • Spacious lot • Outdoor living

Property at 52 Fair St, Guilford, CT 06437, 5 beds, 3 baths

$1,450,000

5 beds3 baths2,744 sq ft

52 Fair St, Guilford, CT 06437

Property at 104 Sperry Dr, Guilford, CT 06437, 3 beds, 2 baths

$469,900

3 beds2 baths1,590 sq ft

104 Sperry Dr, Guilford, CT 06437

Property at 64 Boston St, Guilford, CT 06437, 3 beds, 2 baths

$1,000,000

3 beds2 baths2,657 sq ft

64 Boston St, Guilford, CT 06437

Property at 882 Killingworth Rd, Higganum, CT 06441, 4 beds, 3 baths

$679,900

4 beds3 baths2,286 sq ft

882 Killingworth Rd, Higganum, CT 06441

Property at 82 State St, Guilford, CT 06437, 6 beds, 4 baths

$1,095,000

6 beds4 baths2,783 sq ft

82 State St, Guilford, CT 06437

Property at 51 Pearl St, Guilford, CT 06437, 4 beds, 4 baths

$1,225,000

4 beds4 baths2,392 sq ft

51 Pearl St, Guilford, CT 06437

Property at 50 & 61 Grove Way, Clinton, CT 06413, 3 beds, 3 baths

$2,500,000

3 beds3 baths3,164 sq ft

50 & 61 Grove Way, Clinton, CT 06413

Property at 82 N High St, Clinton, CT 06413, 3 beds, 2 baths

$499,000

3 beds2 baths1,780 sq ft

82 N High St, Clinton, CT 06413

Property at 427 Three Mile Crse, Guilford, CT 06437, 3 beds, 2 baths

$524,999

3 beds2 baths1,380 sq ft

427 Three Mile Crse, Guilford, CT 06437

Property at 13 Waterside Ln, Clinton, CT 06413, 4 beds, 1.5 baths

$725,000

4 beds1.5 baths1,920 sq ft

13 Waterside Ln, Clinton, CT 06413

Property at 64 Dohm Ave, Guilford, CT 06437, 4 beds, 2.5 baths

$550,000

4 beds2.5 baths2,126 sq ft

64 Dohm Ave, Guilford, CT 06437

Property at 131 Cow Hill Rd, Clinton, CT 06413, 4 beds, 2 baths

$540,000

4 beds2 baths2,783 sq ft

131 Cow Hill Rd, Clinton, CT 06413

Property at 275 Route 148, Killingworth, CT 06419, 3 beds, 1.5 baths

$879,500

3 beds1.5 baths2,039 sq ft

275 Route 148, Killingworth, CT 06419

Property at 62 Cedar Island Ave, Clinton, CT 06413, 2 beds, 2 baths

$1,000,000

2 beds2 baths930 sq ft

62 Cedar Island Ave, Clinton, CT 06413

Based on information submitted to the MLS GRID as of Thu Dec 11 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 Madison

There are currently 13 vintage homes for sale in Madison at a median listing price of $725K. 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 65 days and receive 3 offers. This map is refreshed with the newest listings in Madison every 15 minutes.

In the past month, 15 homes have been sold in Madison. In addition to houses in Madison, there were also 8 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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