Madison, CT Homes for Sale

/31
$545,000
- 3 Beds
- 3 Baths
- 2,640 Sq Ft
108 Sandlewood Dr, Madison, CT 06443

Welcome to easy living with this delightful one-story home in Madison, CT. Located 2.5 miles from the scenic Madison Surf Club! This oversized ranch offers a seamless blend of comfort and potential. Picture yourself unwinding by the fireplace in the cozy living room or enjoying the versatility of the expansive den with plenty of room for flex space or entertaining. This home offers three

Jennifer Bordonaro

William Pitt Sotheby's Int'l

(203) 769-9348

108 Sandlewood Dr, Madison, CT 06443
/37
$2,875,000
- 4 Beds
- 4.5 Baths
- 6,194 Sq Ft
24 Indigo Trail, Madison, CT 06443

Come see this stately custom Brick English Georgian home in sought after Madison CT, nestled on a sprawling 5.65 acre lot with Neck River frontage. This exquisite 6,194 square foot colonial offers an unparalleled blend of luxury, privacy and natural beauty. With 4 bedrooms and 4.5 baths, it is designed for those who appreciate both elegance and tranquility. This unique residence is surrounded by

Ron Stewart

Houlihan Lawrence WD

(475) 405-2519

24 Indigo Trail, Madison, CT 06443
/37
$679,000
- 4 Beds
- 1.5 Baths
- 2,458 Sq Ft
29 Flintlock Rd, Madison, CT 06443

***HIGHEST AND BEST DUE BY WEDNESDAY, JULY 16 AT NOON*** This 4-bedroom colonial provides a seamless blend of open design and cozy space. The first floor has hardwood floors, an open floor plan, a welcoming living room with fireplace, and a bright family room set just off the kitchen-perfect for gatherings. Upstairs, you'll find four spacious bedrooms with hardwood floors and an updated full

Betsy Anderson

William Pitt Sotheby's Int'l

(203) 875-0286

29 Flintlock Rd, Madison, CT 06443
/40
$1,595,000
- 4 Beds
- 3.5 Baths
- 5,219 Sq Ft
12 Stanton Ct, Madison, CT 06443

Just minutes from Madison's beautiful beaches and vibrant town center, this exceptional architect-designed home sits at the end of a quiet cul-de-sac. Light-filled and thoughtfully designed, it features a newly remodeled custom kitchen and an open, airy floor plan ideal for modern living. With 4 bedrooms and 3.5 baths, the home includes a spacious primary suite showcasing a wall of windows that

Cathy Lynch

Coldwell Banker Realty

(475) 303-6867

12 Stanton Ct, Madison, CT 06443
/40
$1,995,000
- 5 Beds
- 3.5 Baths
- 3,912 Sq Ft
30 Meeting House Ln, Madison, CT 06443

Once known as "Hartsbourne," this storied Madison residence is celebrated for its premier location overlooking the town green and its timeless architectural presence. A true local landmark, the home is distinguished by its striking curved eaved roofline, reminiscent of a pagoda with a unique flat seamed copper roof center. Beautifully aligned with the neighboring Congregational Church, the home

Cathy Lynch

Coldwell Banker Realty

(203) 442-9594

30 Meeting House Ln, Madison, CT 06443
/40
$3,000,000
- 6 Beds
- 4.5 Baths
- 6,300 Sq Ft
37 Lantern Hill Rd, Madison, CT 06443

Welcome to 37 Lantern Hill Road, a luxurious residence nestled in the heart of Madison's most coveted neighborhood. Just a short stroll from pristine beaches, the charming town center, and the Madison Country Club, this home offers an unparalleled lifestyle of comfort and convenience. Tucked away along picturesque brick-lined sidewalks and illuminated by classic lanterns, this exceptional

Cathy Lynch

Coldwell Banker Realty

(475) 283-9847

37 Lantern Hill Rd, Madison, CT 06443
/40
$625,000
- 3 Beds
- 3,768 Sq Ft
36 Jannas Ln, Madison, CT 06443

Hey there! Check out this stunning contemporary house located just a few houses north of Rt 1. It's sitting on a knoll and has so much potential, but it does need a complete remodeling. This is your chance to redesign the interior and make it your own! The location is perfect - close to town, the Long Island Sound, and even a golf course. This could be your ideal summer retreat or a cozy

Harry Finer

William Raveis Real Estate

(203) 580-6329

36 Jannas Ln, Madison, CT 06443
/15
$173,500
- Land
- 1.55 Acres
- $111,935 per Acre
728 Durham Rd, Madison, CT 06443

Imagine building your dream home on this picturesque 1.55-acre lot in Madison, Connecticut, offering seasonal views of the serene Hog Pond. Throughout the year, enjoy the changing scenery and abundant wildlife, with opportunities for ice skating and hockey on the pond during winter months. The property includes a recent survey with topographical details and a septic design, pending only perc

Gene Pica

RE/MAX Alliance

(475) 290-6060

728 Durham Rd, Madison, CT 06443
/40
$1,899,000
- 5 Beds
- 5.5 Baths
- 6,278 Sq Ft
584 Boston Post Rd, Madison, CT 06443

Elegant European-Style home in the Heart of Madison. A perfect blend of luxury, privacy, and convenience in this remarkable home, ideally located just steps from the Madison Town Green, downtown shops, and stunning beaches. This five-bedroom home offers a host of exceptional features. Step through the front door into a dramatic two-story great room with an open floor plan, bathed in natural

Kate Jasko Coldwell Banker Realty

584 Boston Post Rd, Madison, CT 06443
/40
$875,000
- 3 Beds
- 4 Baths
- 2,235 Sq Ft
3 Arrowhead Rd, Madison, CT 06443

Newly Priced! Embrace the enchantment of Shoreline Living at its finest with this sun-drenched haven at 3 Arrowhead, a jewel nestled in a quaint community with the river at your doorstep. As you step into this radiant abode, you're welcomed by a symphony of natural light and the serene melodies of local birdsong. The home's design harmoniously blends the outdoors with the indoors, creating a

Diana Hartman William Pitt Sotheby's Int'l

3 Arrowhead Rd, Madison, CT 06443
/39
$990,000 Open House 7/27
- 3 Beds
- 2.5 Baths
- 2,558 Sq Ft
659 Summer Hill Rd, Madison, CT 06443

Have Fun! Summer: pool, large deck, fenced yard, and central AC! Winter: Fireplaces, holiday meals, room for guests. Yesterday's charm & all the conveniences of today (new roof, new boiler, new central AC, Updated Kitchen) With wide plank Chestnut floors and 3 fireplaces on the first floor: the vintage house charm with current comfort is inviting! Access to the deck from the Dining Room and

Leigh Whiteman William Raveis Real Estate

659 Summer Hill Rd, Madison, CT 06443
/39
$1,665,000
- 5 Beds
- 6 Baths
- 5,779 Sq Ft
110 Randi Dr, Madison, CT 06443

Welcome to 110 Randi Drive, where a stately circular driveway ushers you into a realm of elegance & comfort. This grand & classic 5,779 sf residence is a testament to luxurious living, offering a harmonious blend of expansive open areas. As you step through the front door, you're greeted by a formal living room adorned w/ French doors & the first of 3 fireplaces, a space that could effortlessly

Amy Kirst William Pitt Sotheby's Int'l

110 Randi Dr, Madison, CT 06443
/26
$850,000
- 3 Beds
- 1.5 Baths
- 1,116 Sq Ft
57 Circle Beach Rd, Madison, CT 06443

Nestled along the shores of Long Island Sound, this classic 3-bedroom, 1.5-bath, this 1116 sq.ft cottage offers a rare opportunity to own a true waterfront retreat with panoramic views-including Faulkner's Island-and a separate deep water dock on the Neck River just across the street. From the moment you step inside, you're welcomed by sweeping, unobstructed water views and endless potential.

Cheryl Kebalo ENRG Global Realty, LLC

57 Circle Beach Rd, Madison, CT 06443
/40
$1,098,000
- 5 Beds
- 3 Baths
- 2,781 Sq Ft
8 Highview Rd, Madison, CT 06443

One-of-a-kind home in a small, sought-after subdivision close to the heart of charming Madison, CT. This architecturally distinctive residence features soaring cathedral ceilings and skylights in the living room, vaulted ceilings in the dining room, and a striking shiplap ceiling in the expansive family room. Two wood-burning fireplaces create cozy focal points in both living and family rooms.

Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

8 Highview Rd, Madison, CT 06443
/40
$875,000
- 4 Beds
- 2.5 Baths
- 4,879 Sq Ft
48 Shepherds Trail, Madison, CT 06443

Welcome to your private oasis-This one-of-a-kind Contemporary Colonial home offers 4 bedrooms, 2.5 baths, and a versatile floor plan designed for both grand entertaining & everyday comfort. Step into the impressive foyer, where an expansive living room & formal dining area set the stage for elegant gatherings. The kitchen at the heart of the main level gleams with granite countertops,

Erin Connelly Coldwell Banker Realty

48 Shepherds Trail, Madison, CT 06443
/40
$1,395,000
- 3 Beds
- 2.5 Baths
- 2,538 Sq Ft
908 Boston Post Rd, Madison, CT 06443

THE GENERAL'S RESIDENCES at Fence Creek, the perfect & rare combination of location, luxury & comfort in the heart of charming small town Madison w/ it's nationally recognized independent R J Julia Booksellers, 2 screens Madison Arts Cinema, specialty shops & numerous fine dining establishments. There is a glorious & sandy Town Beach for residents only literally just a walk down the street w/ not

Todd Gould William Pitt Sotheby's Int'l

908 Boston Post Rd, Madison, CT 06443
/28
$1,950,000
- 4 Beds
- 3 Baths
- 2,864 Sq Ft
917 Boston Post Rd, Madison, CT 06443

This iconic property offers a rare opportunity to own a piece of Madison's history. This meticulously restored colonial offers the perfect blend of historic charm and modern luxury. Just a short walk from the library, Bar Bouchee, and the beach, this home provides an unparalleled lifestyle in one of the area's most coveted locations. With keen attention to detail, every aspect of this home has

Meig Walz Newcomb Coldwell Banker Realty

917 Boston Post Rd, Madison, CT 06443
/31
$899,000
- 3 Beds
- 3.5 Baths
- 3,772 Sq Ft
13 Longview Terrace, Madison, CT 06443

Privately sited at the end of Longview Terrace with expansive marsh and river views this larger than most free-standing colonial at over 3700 sf offers luxurious condo living. With a three-story generous layout this unit is south facing and full of light and custom details. The oversized kitchen with breakfast area is open to a 22x17 private deck. The primary suite offers a fireplace, a very

Margaret Muir William Pitt Sotheby's Int'l

13 Longview Terrace, Madison, CT 06443
/9
$1,350,000 New Construction
- 4 Beds
- 3.5 Baths
- 3,568 Sq Ft
454 Horse Pond Rd Unit C, Madison, CT 06443

2025 is the year to have the home of your dreams! Come see this gorgeous enclave of five to-be-built houses on a private road in the charming coastal town of Madison. Ideally located just two hours from both NYC and Boston, Madison is beloved for its award-winning schools, restaurants, shops, and of course, beautiful beaches! Constructed by a well-established local Madison builder, these houses

Karen Rosenthal William Raveis Real Estate

454 Horse Pond Rd Unit C, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,568 Sq Ft
1339 Boston Post Rd Unit 2-5, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1339 Boston Post Rd Unit 2-5, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,150 Sq Ft
1339 Boston Post Rd Unit 2-6, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1339 Boston Post Rd Unit 2-6, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,568 Sq Ft
1339 Boston Post Rd Unit 3-1, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1339 Boston Post Rd Unit 3-1, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,230 Sq Ft
1339 Boston Post Rd Unit 3-2, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1339 Boston Post Rd Unit 3-2, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,470 Sq Ft
1339 Boston Post Rd Unit 3-3, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1339 Boston Post Rd Unit 3-3, Madison, CT 06443
/8
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,568 Sq Ft
1339 Boston Post Rd Unit 3-5, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1339 Boston Post Rd Unit 3-5, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,150 Sq Ft
1339 Boston Post Rd Unit 3-6, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1339 Boston Post Rd Unit 3-6, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,140 Sq Ft
1341 Boston Post Rd Unit 3-6, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1341 Boston Post Rd Unit 3-6, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,470 Sq Ft
1341 Boston Post Rd Unit 3-5, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1341 Boston Post Rd Unit 3-5, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,470 Sq Ft
1341 Boston Post Rd Unit 3-3, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1341 Boston Post Rd Unit 3-3, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,230 Sq Ft
1341 Boston Post Rd Unit 3-2, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1341 Boston Post Rd Unit 3-2, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,470 Sq Ft
1341 Boston Post Rd Unit 3-1, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1341 Boston Post Rd Unit 3-1, Madison, CT 06443
/7
$1,450,000 New Construction
- 2 Beds
- 2 Baths
- 1,140 Sq Ft
1341 Boston Post Rd Unit 2-6, Madison, CT 06443

Welcome to the Marketplace of Madison, located on the beautiful Madison shoreline this exquisite new construction project featuring 24 luxury units designed with the finest finishes and modern conveniences. Nestled in the heart of Madison, CT, these stunning residences offer a mix of one and two-bedroom units, each thoughtfully crafted to provide the ultimate living experience. Each unit boasts

Vinny Valentino Advise Realty Services

1341 Boston Post Rd Unit 2-6, Madison, CT 06443
/38
$850,000
- 3 Beds
- 3 Baths
- 2,220 Sq Ft
330 Foxwood Rd, Guilford, CT 06437

Set on a serene .92-acre lot in one of Guilford's most desirable neighborhoods, this impeccably maintained 3-bedroom, 3-bath home offers 2,220 square feet of thoughtfully designed living space. With numerous upgrades and attention to detail throughout, this property perfectly blends comfort, functionality, and style. Step inside to find a warm and inviting layout featuring spacious living areas,

Eric Ryalls William Pitt Sotheby's Int'l

330 Foxwood Rd, Guilford, CT 06437
/24
$262,500
- 1 Bed
- 1 Bath
- 548 Sq Ft
76 South St, Madison, CT 06443

Welcome home to 76 South Street - the perfect seasonal retreat to enjoy all seaside Madison offers! Completely and thoughtfully rebuilt in 1999 and meticulously maintained ever since, this wonderfully open and inviting cottage offers the ideal setting for entertaining and tranquility with an interior and exterior that will leave you swooning! Opening the front door and stepping inside, you will

Melanie Abbott William Pitt Sotheby's Int'l

76 South St, Madison, CT 06443
/40
$1,899,000
- 5 Beds
- 6 Baths
- 6,278 Sq Ft
584 Boston Post Rd, Madison, CT 06443

Elegant European-Style home in the Heart of Madison. A remarkable home ideally located just steps from the Madison Town Green, downtown shops, and stunning beaches. This five-bedroom home offers a host of exceptional features including a newly remodeled in-law/accessory apartment with its own private entrance, a gorgeous kitchen, living room, dining area, 2 full baths, and washer and dryer. Step

Kate Jasko Coldwell Banker Realty

584 Boston Post Rd, Madison, CT 06443
/27
$465,000
- 3 Beds
- 1.5 Baths
- 1,468 Sq Ft
20 Robin Ridge Dr, Madison, CT 06443

Welcome to 20 Robin Ridge Drive, a charming ranch-style home located in the highly sought-after Robin Ridge neighborhood! Ideally located just over 2 miles from Downtown Madison and approximately 3 miles to the Madison Beach Hotel, West Wharf Beach, and the Surf Club, this property combines comfort, convenience, and coastal living. This inviting home offers 3 generously sized bedrooms with

Anne Marie Straka Compass Connecticut, LLC

20 Robin Ridge Dr, Madison, CT 06443
/39
$700,000
- 4 Beds
- 2.5 Baths
- 2,424 Sq Ft
310 Opening Hill Rd, Madison, CT 06443

Welcome to this charming and extensively updated colonial home that embodies comfort and style. With a wealth of improvements completed in 2014, including new windows, roof, driveway and a beautiful kitchen, this home is move-in ready. Recent enhancements in 2024 include an updated primary bath and half bath, making it even more inviting for you and your guests. The added Ring doorbell, newly

Barbara Goetsch William Pitt Sotheby's Int'l

310 Opening Hill Rd, Madison, CT 06443
/38
$575,000
- 3 Beds
- 2 Baths
- 2,159 Sq Ft
9 Madrina Ln, Madison, CT 06443

Tucked away at the end of a quiet cul-de-sac, this 3-bedroom, 2-bath contemporary style home sits on a private .6-acre lot in a desirable location; just minutes from beaches, Hammonasset State Park, the scenic Shoreline walking trails, and the vibrant center of town. Steps lead up to the front deck and entry foyer, opening to a light-filled, open-concept living space. Cathedral ceilings with

Rose Ciardiello William Raveis Real Estate

9 Madrina Ln, Madison, CT 06443
/22
$899,900
- Land
- 0.19 Acre
- $4,736,316 per Acre
885 Boston Post Rd, Madison, CT 06443

Fully approved and ready to go, this exceptional commercial lot is situated in the heart of vibrant downtown Madison. Boasting approvals for a 5,000 square foot building the property includes a brand-new septic system, 13 designated parking spaces with additional parking options, and unbeatable proximity to restaurants, shopping, the train station, and I-95. Imagine welcoming clients or customers

Michael Hvizdo Coldwell Banker Realty

885 Boston Post Rd, Madison, CT 06443
/26
$325,000
- 2 Beds
- 3 Baths
- 1,332 Sq Ft
2 Brantwood Dr, Madison, CT 06443

Welcome to this move in ready townhouse located just a short walk to downtown Madison. Newly installed sidewalks make it convenient to visit everything Madison has to offer - shopping, movie theater, restaurants, farmers market and Sunday evening concerts. This unit offers 2 bedrooms, 1.2 baths with over 1300 s.f. The updated kitchen has shaker cabinets, granite countertops and stainless steel

Rebecca Ferguson Coldwell Banker Realty

2 Brantwood Dr, Madison, CT 06443

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