Madison, CT Houses for Sale

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  /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
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  /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
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  /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
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  /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
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  /40

  $1,445,000

  • 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 on a quiet o cul-de-sac street. This home boasts both town water and Natural gas. 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

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 693-9631

  12 Stanton Ct, Madison, CT 06443
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  /40

  $949,900

  • 4 Beds
  • 5 Baths
  • 3,986 Sq Ft

  16 Yankee Peddler Path, Madison, CT 06443

  This fully renovated and expanded Farmhouse Colonial offers nearly 4,000 sq ft of luxurious living space on a private 1.6-acre lot, blending timeless charm with modern upgrades. Every detail has been thoughtfully updated from roof to flooring, including new HVAC system, electrical, plumbing, a gourmet kitchen with center island and huge walk-in pantry, stylish bathrooms, and more. With 4 spacious

  Linda Toscano Coldwell Banker Realty

  16 Yankee Peddler Path, Madison, CT 06443
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  /40

  $849,999

  • 4 Beds
  • 2.5 Baths
  • 4,879 Sq Ft

  48 Shepherds Trail, Madison, CT 06443

  This one-of-a-kind Contemporary Colonial home features 4 bedrooms, 2.5 baths, and a versatile floor plan designed for both grand entertaining and everyday comfort. Step into the impressive foyer, where an expansive living room and formal dining area set the stage for large gatherings. At the heart of the main level, the kitchen shines with granite countertops, stainless steel appliances, and a

  Erin Connelly Coldwell Banker Realty

  48 Shepherds Trail, Madison, CT 06443
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  /40

  $869,000

  • 3 Beds
  • 3 Baths
  • 2,393 Sq Ft

  43 Burcam Dr, Madison, CT 06443

  Do not miss this beautiful expanded Cape with its great entertainment areas and breathtaking gardens. Less than a mile to the farmers market and live music on the green; enjoy easy access to Madison's beaches and quaint town. This home offers both privacy and convenience to all. With 3 bedrooms and 3 full bathrooms, a fully finished basement, extensive storage, a stunning four season room and a

  Kimberly Stasiak Century 21 AllPoints Realty

  43 Burcam Dr, Madison, CT 06443
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  /36

  $779,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 2,698 Sq Ft

  129 Acorn Rd, Madison, CT 06443

  MARRY the HOUSE DATE THE MORTGAGE a stone's throw away from the heart of Madison Village, perfectly positioned at 1.4 miles from the bustling center, with beaches, recreational fields, and the renowned Bookstore. Shopping, dining, and are all conveniently close, making this an ideal location for those seeking both tranquility and community amenities. Occupying a generous .74-acre level lot, the

  Ann Stewart William Pitt Sotheby's Int'l

  129 Acorn Rd, Madison, CT 06443
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  /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
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  /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
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  /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
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  /26

  $699,000

  • 4 Beds
  • 2 Baths
  • 1,896 Sq Ft

  7 Derenthal Dr, Madison, CT 06443

  Welcome to this beautifully updated 4-bedroom, 2-bath split-level home with a sleek, contemporary design. The main level features an open-concept layout with an updated kitchen, hardwood flooring, and vaulted ceiling. Sliding doors lead to a spacious enclosed 3 season porch, complete with a skylight and ceiling fan-perfect for relaxing or entertaining. Step outside to enjoy a deck, a patio, and

  Susan Warner-Lambert Carbutti & Co., Realtors

  7 Derenthal Dr, Madison, CT 06443
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  /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
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  /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
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  /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
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  /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
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  /34

  $799,900 Open House 8/06

  • 4 Beds
  • 2.5 Baths
  • 3,999 Sq Ft

  42 Buck Hill Rd, Madison, CT 06443

  Tucked away on 1.88 acres of level land in one of the area's most beautiful neighborhoods, this 4-bedroom contemporary colonial offers the perfect blend of privacy. Inside, natural light floods the home through skylights and oversized windows. The dramatic two-story entry opens to a bright living room with soaring ceilings, creating an immediate sense of space and comfort. The living room flows

  Susan Santoro William Pitt Sotheby's Int'l

  42 Buck Hill Rd, Madison, CT 06443
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  /32

  $849,000 Open Fri 4PM - 6PM

  • 4 Beds
  • 3 Baths
  • 3,464 Sq Ft

  241 Hunters Trail, Madison, CT 06443

  Tucked away in one of Madison's most desirable subdivisions, this spacious 4-bedroom, 3.5-bath colonial offers the perfect blend of function, flow, and comfort-just minutes to downtown, beaches, the highway, and medical facilities. The heart of the home is the warm and inviting kitchen, complete with rich cherry cabinets, an oversized island, ample storage, and generous counter space-designed for

  Heidi DeRusso Coldwell Banker Realty

  241 Hunters Trail, Madison, CT 06443
• 

  /2

  $800,000 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  677 Durham Rd, Madison, CT 06443

  Stunning 3-Bed, 2.5-Bath Home Built in 2022 - Immaculate and Move-In Ready! Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home, built in 2022 and designed for modern living. From the moment you step inside, you'll be impressed by the open floor plan that seamlessly blends living, dining, and kitchen spaces-perfect for both everyday life and entertaining. Custom built-ins

  Meig Walz Newcomb Coldwell Banker Realty

  677 Durham Rd, Madison, CT 06443
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  /38

  $795,000

  • 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
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  /37

  $212,000

  • 2 Beds
  • 1 Bath
  • 647 Sq Ft

  26 North St, Madison, CT 06443

  Madison Connecticut - By the sea, literally! Beautifully framed cottage is evident here! Character in exposed wood and wooden beamed vaulted ceilings. Tons of sunlight stream into this beautiful home! Sunny living room, bedroom/den, and patio. This CORNER lot provides easy parking, a darling patio, exceptional large wooden shed, professionally landscaped lawn! Location offers an easy one mile

  Laurie McCann William Pitt Sotheby's Int'l

  26 North St, Madison, CT 06443
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  /32

  $249,000

  • 3 Beds
  • 1 Bath
  • 897 Sq Ft

  4 North St, Madison, CT 06443

  **Seasonal Beach Living in Madison** Experience the ultimate coastal getaway with this charming seasonal cottage, available from April 1 to October 31. Nestled within a mile of stunning beaches, you'll have easy access to not only the sun and surf but also scenic hiking and biking trails nearby. Enjoy the vibrant local culture with a variety of delightful shoreline restaurants and unique shops

  Kristy Vaiuso Coldwell Banker Realty

  4 North St, Madison, CT 06443
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  /33

  $650,000

  • 4 Beds
  • 2.5 Baths
  • 1,894 Sq Ft

  9 Monroe Ln, Madison, CT 06443

  Nestled on a corner lot in a quiet cul-de-sac sits this lovely 4 bed, 2.5 bath Colonial in a great neighborhood near everything: schools, downtown, beaches, highway, Madison Land Trust & Cockaponset State Forest! Classic colonial floor plan offers generously sized living room, dining room for entertaining, large kitchen with eat-in-area and 3 season sunporch all on the 1st floor. Lots of natural

  Karen Lee Coldwell Banker Realty

  9 Monroe Ln, Madison, CT 06443
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  /40

  $2,799,000

  • 5 Beds
  • 4 Baths
  • 3,397 Sq Ft

  25 Seaview Ave, Madison, CT 06443

  Unique, custom, architecturally designed home in the desirable Seaview Beach area. Situated on a high point of Seaview Ave on a corner lot, with deeded access rights to Long Island Sound. The sandy beach is accessed by a dedicated waterway with cabana. Perfect for a second or summer home, as well as a primary residence. This home was entirely rebuilt in 2010 and boasts numerous amenities &

  Alison Gould Gould Group LLC

  25 Seaview Ave, Madison, CT 06443
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  /32

  $580,000

  • 4 Beds
  • 3.5 Baths
  • 2,656 Sq Ft

  40 Puritan Ln, Madison, CT 06443

  Spacious and thoughtfully expanded, this one-owner split-level home offers 4 bedrooms and 3.1 bathrooms and is ideally located just 1.5 miles from downtown Madison. Over the years, the home has been enhanced to create a desirable open floor plan, featuring a sun-filled great room with cathedral ceilings, a fireplace and screened porch at the rear of the home-perfect for everyday living and

  Dana Weinstein Coldwell Banker Realty

  40 Puritan Ln, Madison, CT 06443
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  /27

  $625,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  108 Boston Post Rd, Madison, CT 06443

  Welcome to this beautifully preserved and tastefully updated antique home, ideally situated on a generous 0.92-acre lot in the heart of Madison. Offering three bedrooms and two full baths, this residence perfectly balances historic character with everyday comfort. The inviting kitchen features exposed beams that bring warmth and charm, while thoughtful updates ensure a seamless blend of rustic

  Cindy Breckheimer Forever Homes Real Estate LLC

  108 Boston Post Rd, Madison, CT 06443
• 

  

  /19

  $156,900

  • 2 Beds
  • 1 Bath
  • 396 Sq Ft

  92 4th St, Madison, CT 06443

  Nestled in the heart of picturesque Madison, this charming 2-bedroom, 1-bathroom seasonal cottage offers a serene sanctuary for enjoying summers along the shoreline. With a cozy living space, this quaint abode is perfectly designed for those seeking a peaceful beachside getaway. As you step inside, you're greeted by a warm and inviting atmosphere that captures the essence of coastal living. The

  Melanie Abbott William Pitt Sotheby's Int'l

  92 4th St, Madison, CT 06443
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  /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
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  /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
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  /38

  $4,000,000

  • 5 Beds
  • 6 Baths
  • 4,450 Sq Ft

  77 E Wharf Rd, Madison, CT 06443

  Welcome to 77 East Wharf! This beautifully designed five-bedroom Cape Cod-style home is perfectly situated high on the property to capture breathtaking views of the Long Island Sound and tranquil Fence Creek. Ideal for entertaining or hosting beach-loving visitors, this home also includes a charming one-bedroom apartment over the garage. Begin your experience with a private walkway bordered by a

  Meig Walz Newcomb Coldwell Banker Realty

  77 E Wharf Rd, Madison, CT 06443
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  /27

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,192 Sq Ft

  1281 Durham Rd, Madison, CT 06443

  CHARMING LARGE MADISON MOTHER /DAUGHTER 2 BEDROOMS LARGE MODERN CHEFS KITCHEN LIVING ROOM WITH FIREPLACE LARGE BATH LAUNDRY AND BONUSROOM EXTENDING THE WIDTH OF THE HOUSE UPSTAIRS ALL NEW A LARGE LIVING ROOM KITCHEN BATH 2 BEDROOMS AND A PRIVATE ENCLOSED BALCONY OVERLOOKING THE BEAUTIFUL JUST SHY 1/2 ACRE PRIVATE YARD. AND GARAGE. A MUST SEE A TRUE FAMILY HOME !!!

  Dan Rocano Exit Realty Everyday

  1281 Durham Rd, Madison, CT 06443
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  /18

  $179,900

  • 1 Bed
  • 1 Bath
  • 441 Sq Ft

  7 3rd St, Madison, CT 06443

  Madison, SEASHORE! - Coastal living adjacent to Hammonassett Beach State Park! HIGH VALUE! This astute, masterfully updated, well built circa 1958 cottage is the perfect vacation retreat! Big open floor plan living room!! Young's Village is seasonal offering a 7 month term of full time use. Seasonal community where you may occupy your home full time April 1 - October 31. Third Street offers

  Laurie McCann William Pitt Sotheby's Int'l

  7 3rd St, Madison, CT 06443
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  /18

  $140,000

  • 1 Bed
  • 1 Bath
  • 476 Sq Ft

  16 North St, Madison, CT 06443

  If you're dreaming of summers by the shoreline, this charming cottage in Dud's Village, Madison, offers the perfect seasonal escape. Less than a mile from Hammonasset Beach State Park-Connecticut's largest shoreline park-this move-in-ready cottage offers easy access to two miles of sandy beaches, scenic walking and biking paths, and endless outdoor activities. A private path from the village

  Margaret Curry William Raveis Real Estate

  16 North St, Madison, CT 06443
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  /9

  $1,375,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 4,357 Sq Ft

  454 Horse Pond Rd Unit B, 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 B, Madison, CT 06443
• 

  

  /9

  $1,275,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 3,568 Sq Ft

  454 Horse Pond Rd Unit A, 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 A, Madison, CT 06443
• 

  

  /33

  $465,000 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  24 Deepwood Dr, Madison, CT 06443

  Great Opportunity To Live In Madison for a reasonable price. This three level split home on a level, treed lot in established neighborhood is ready to be your next home. Hardwood throughout living room and all 3 bedrooms. Enjoy the oversized 3 season screen porch this Fall and cozy up in front of the raised hearth fireplace this Winter. Just under one full acre, this home is private and set on a

  Carol Mancini William Pitt Sotheby's Int'l

  24 Deepwood Dr, Madison, CT 06443
• 

  /2

  $249,000 Coming Soon

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  2175 Durham Rd, Madison, CT 06443

  Opportunity Knocks! The 3-bedroom ranch situated on just under 1 acre offers the perfect chance to create your own vision. With some TLC, this single-level home can be transformed into a cozy and comfortable retreat tailored to your style. Whether you're a first-time buyer or looking to downsize, this property provides a solid foundation in a peaceful neighborhood. Enjoy the ease of single-level

  Nicholas Mastrangelo Coldwell Banker Realty

  2175 Durham Rd, Madison, CT 06443
• 

  

  /30

  $295,000

  • 3 Beds
  • 1 Bath
  • 2,199 Sq Ft

  25 Route 79, Killingworth, CT 06419

  Backyarder Bonus Stonehouse! Quality crafted stone house with huge outbuilding. Main level bedroom with fireplace, Great room crafted from ship hull with heart shaped fireplace. Two additional bedrooms on upper level. Walk out lower level with playspace. This is a Fannie Mae home.

  Billie Galessio HomeRun Realty LLC

  25 Route 79, Killingworth, CT 06419

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