Madison, CT Homes

• 

  Est $666,300 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  263 Legend Hill Rd, Madison, CT 06443

  263 Legend Hill Rd, Madison, CT 06443
• 

  

  

  /39

  $1,785,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 6,278 Sq Ft

  584 Boston Post Rd, Madison, CT 06443

  IN TOWN LIVING! 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 light. The newly updated kitchen, fresh

  Kate Jasko Coldwell Banker Realty

  584 Boston Post Rd, Madison, CT 06443
• 

  $621,000 Sold Jun 24, 2025

  • 1,383 Sq Ft
  • $449/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  173 Bradley Corners Rd, Madison, CT 06443

  This beautifully renovated carriage house offers a blend of modern elegance and serene countryside charm. Set on just under two meticulously landscaped acres, the property features thoughtfully designed walking trails that meander through lush greenery, creating a peaceful retreat. The main level features a welcoming mudroom, a spacious laundry room for added convenience, versatile bedroom suite

  Cathy Lynch Coldwell Banker Realty

  173 Bradley Corners Rd, Madison, CT 06443
• 

  Est $575,243 Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 2,476 Sq Ft

  279 Legend Hill Rd, Madison, CT 06443

  279 Legend Hill Rd, Madison, CT 06443
• 

  

  

  /40

  $575,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  113 Scotland Rd, Madison, CT 06443

  Turn-key! First floor living awaits in fabulous Madison! Thoughtfully renovated 3 Bedroom, 2 Full Bath Cape Cod w/ detached garage offers classic charm w/ convenience & accessibility. Gleaming hardwood floors, new crown molding & recessed lighting throughout main level. Living room w/ beautifully crafted knotty pine built-ins surround the wood-burning fireplace. Living room opens to sun-drenched

  Katie Westrin William Raveis Real Estate

  113 Scotland Rd, Madison, CT 06443
• 

  $1,220,000 Sold Jun 24, 2025

  • 4,442 Sq Ft
  • $275/SF
  • 37 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1992

  59 Copperfield Dr, Madison, CT 06443

  Graciously Remodeled Colonial located in a highly desirable neighborhood at the end of a peaceful cul-de-sac, this beautifully remodeled 4-bedroom colonial offers timeless charm with modern updates. Step into a welcoming two-story foyer that opens to a sunlit, open-concept layout with soaring cathedral ceilings-perfect for entertaining. The remodeled kitchen flows seamlessly into the family room,

  Cathy Lynch Coldwell Banker Realty

  59 Copperfield Dr, Madison, CT 06443
• 

  Est $565,071 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 2,140 Sq Ft

  75 Legend Hill Rd, Madison, CT 06443

  75 Legend Hill Rd, Madison, CT 06443
• 

  

  /40

  $1,098,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,660 Sq Ft

  62 Wellsweep Dr, Madison, CT 06443

  An Exceptional Home in the Tall Oaks subdivision... This meticulously maintained and constantly upgraded private home in the cul-de-sac Wellsweep neighborhood is absolutely turnkey. Set on a hill, among tall oaks and beautiful landscaping, this 3-4 bedroom unique Colonial style home exudes charm with all the extra modern features, and then some. Every room is spacious and airy with hardwood

  Alison Gould Gould Group LLC

  62 Wellsweep Dr, Madison, CT 06443
• 

  $637,500 Sold Jun 23, 2025

  • 1,747 Sq Ft
  • $365/SF
  • 2 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1952

  1225 Durham Rd, Madison, CT 06443

  Be ready to fall in love with this beautifully maintained 1952 Cape Cod, offering 3 bedrooms and 3 baths. The heart of this home is its stunning, renovated kitchen, featuring all the modern amenities you could want, perfectly blending classic charm with contemporary design. Set on 2 bucolic acres, this property offers a serene and private retreat with an inviting inground pool, ideal for relaxing

  Carol Farmer William Raveis Real Estate

  1225 Durham Rd, Madison, CT 06443
• 

  Est $554,173 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,946 Sq Ft

  22 Legend Hill Rd, Madison, CT 06443

  22 Legend Hill Rd, Madison, CT 06443
• 

  

  /40

  $377,500 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,434 Sq Ft

  15D Yankee Glen Rd Unit 15D, Madison, CT 06443

  Welcome to 15D Yankee Glen, Madison! Come see this beautifully appointed condo! Location is ideal - so close to Downtown Madison, train, and highway. This unit has been lovingly maintained and is ready for its new owner! The open floor plan and vaulted ceilings fill this charming unit with a bright, airy, and inviting atmosphere. With a wood burning fireplace, public water, natural gas, newer

  Lisa Rollins Team Compass Connecticut, LLC

  15D Yankee Glen Rd Unit 15D, Madison, CT 06443
• 

  $550,000 Sold Jun 23, 2025

  • 1,576 Sq Ft
  • $349/SF
  • 201 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  67 New Rd, Madison, CT 06443

  Perfect Location - Just Minutes to Hammonasset Beach, Downtown Madison & I-95! This beautifully updated 3-bedroom, 2-bathroom ranch offers comfortable single-level living with an additional office and a spacious family room. The eat-in kitchen has been tastefully updated with Corian countertops and stainless-steel appliances. A screened-in porch leads to a new paver patio-perfect for outdoor

  Nancy Potts Coldwell Banker Realty

  67 New Rd, Madison, CT 06443
• 

  Est $573,017 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,768 Sq Ft

  39 Beechwood Dr, Madison, CT 06443

  39 Beechwood Dr, Madison, CT 06443
• 

  

  /32

  $699,000 Pending

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  29 Circle Beach Rd, Madison, CT 06443

  A little piece of paradise awaits you in this direct, waterfront cottage. Perfectly situated with unobstructed views of Long Island Sound. Shoreline living at its best in this beautiful beach community! So much potential and options to make this 2-bedroom gem your own. Re-model to your taste or utilize the walk-up attic, to build up, for additional living space. Enjoy your private beach or the

  Gary Piccirillo RE/MAX Right Choice

  29 Circle Beach Rd, Madison, CT 06443
• 

  $349,000 Sold Jun 20, 2025

  • 1,261 Sq Ft
  • $277/SF
  • 5 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  23A Yankee Glen Rd Unit 23A, Madison, CT 06443

  Welcome to this beautiful freestanding condo ideally located within walking distance to downtown and the train station. This inviting home features cathedral ceilings and an open-concept layout that seamlessly connects the kitchen, dining, and living areas-perfect for both everyday living and entertaining. A cozy fireplace adds warmth and charm to the living space, while large windows offer

  Kelsey Oddo Kelsey & Co. Real Estate

  23A Yankee Glen Rd Unit 23A, Madison, CT 06443
• 

  Est $566,827 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  14 Oakwood Dr, Madison, CT 06443

  14 Oakwood Dr, Madison, CT 06443
• 

  

  /40

  $869,000 Pending

  • 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
• 

  $972,000 Sold Jun 20, 2025

  • 3,068 Sq Ft
  • $317/SF
  • 92 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1955

  114 Neck Rd, Madison, CT 06443

  This stunning riverfront colonial, just blocks from the Long Island Sound, offers an unparalleled lifestyle. Imagine relaxing in your private backyard, complete with a saltwater hot tub, while enjoying breathtaking views of the Neck River. The home's interior is equally captivating. A spacious living room, featuring a wood-burning fireplace, provides a focal point with direct river views.

  Toni Iandoli William Pitt Sotheby's Int'l

  114 Neck Rd, Madison, CT 06443
• 

  Est $748,135 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,568 Sq Ft

  674 Opening Hill Rd, Madison, CT 06443

  674 Opening Hill Rd, Madison, CT 06443
• 

  

  /40

  $550,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,896 Sq Ft

  26 Legend Hill Rd Unit 26, Madison, CT 06443

  Rarely Available Ranch-Style Unit with Attached Garage in Legend Hill. Beautifully renovated offering the ease of one-floor living in a serene and luxurious setting. Featuring hardwood floors and light-filled interiors, the open-concept layout includes a spacious dining area that flows seamlessly into a living room with a cozy wood-burning fireplace; perfect for entertaining or relaxing at home.

  Rose Ciardiello William Raveis Real Estate

  26 Legend Hill Rd Unit 26, Madison, CT 06443
• 

  $1,225,000 Sold Jun 19, 2025

  • 2,340 Sq Ft
  • $524/SF
  • 46 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1957

  16 Rockledge Dr, Madison, CT 06443

  Welcome to 16 Rockledge Dr, an amazing home that blends modern elegance of mid-century with New England Beautiful Style. The house Sets proudly on the opening of Rockledge hill overlooking the Madison Country Club golf course and the Long Island Sound in one of the most desirable Neighborhoods in the town of Madison. Beautifully maintained Gunite pool/spa and large pool deck, strategically

  Bob Yostos Coldwell Banker Realty

  16 Rockledge Dr, Madison, CT 06443
• 

  Est $1,190,519 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,879 Sq Ft

  90 Joshua Trail, Madison, CT 06443

  90 Joshua Trail, Madison, CT 06443
• 

  

  /40

  $1,275,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 5,527 Sq Ft

  188 Bartlett Dr, Madison, CT 06443

  Welcome to your dream home! Nestled in the prestigious Neck River Farms, this stunning 4-bedroom colonial offers the ultimate in comfort and elegance. Imagine preparing gourmet meals in your chef-inspired kitchen, boasting high-end cabinetry, a sprawling island, double ovens, gleaming granite countertops, and stainless-steel appliances. Sun-drenched mornings await in the breakfast nook,

  James Montanaro Coldwell Banker Realty

  188 Bartlett Dr, Madison, CT 06443
• 

  $715,000 Sold Jun 18, 2025

  • 1,986 Sq Ft
  • $360/SF
  • 41 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1974

  81 Colonial Rd, Madison, CT 06443

  Move right in to this beautifully renovated 4-bedroom, 2.5-bath Saltbox Colonial offering over 2,600 sq. ft. of stylish living space, just minutes from town and beaches. Set on 1.63 lightly wooded acres, the property backs up to land trust and 33 acres of Cockaponsett State Forest, with seasonal views of Madison Lakes to the east. Designer touches throughout include walnut-stained wide board

  Willard Finkle Coldwell Banker Realty

  81 Colonial Rd, Madison, CT 06443
• 

  Est $1,179,711 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,678 Sq Ft

  87 Joshua Trail, Madison, CT 06443

  87 Joshua Trail, Madison, CT 06443
• 

  

  /12

  $1,375,000 Pending

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

  462 Horse Pond Rd, 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

  462 Horse Pond Rd, Madison, CT 06443
• 

  $245,000 Sold Jun 17, 2025

  • 792 Sq Ft
  • $309/SF
  • 6 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1987

  65 Old Route 79 Unit 8, Madison, CT 06443

  A great price to get a start in the town of Madison. Newer kitchen & Living room floors. Kitchen with eating area. Laundry Hook-ups on the main Level. Large Primary Bedroom with plenty of space for a combo office area with a walk-in closet and a second closet with shelving. Pull downstairs to attic for storage. Convenient location. Close enough to walk to train depot and town. Quaint small

  Robert Teodosio William Raveis Real Estate

  65 Old Route 79 Unit 8, Madison, CT 06443
• 

  Est $530,567 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  33 Deepwood Dr, Madison, CT 06443

  33 Deepwood Dr, Madison, CT 06443
• 

  

  /6

  $1,250,000 Pending

  • 2 Beds
  • 3.5 Baths
  • 2,000 Sq Ft

  0 Bushnell Ln, Madison, CT 06443

  Location, location, location! Build your home in the shoreline town of Madison! This proposed 2000sf modern farmhouse style home has a first floor primary bedroom, 3 full baths with additional space for an office, a rec room and an open floor plan. Vaulted ceilings, lots of natural light and energy efficiency make this build stand out. The proposed design can be modified to meet your needs.

  Justin Bradley Coldwell Banker Realty

  0 Bushnell Ln, Madison, CT 06443
• 

  $1,667,000 Sold Jun 17, 2025

  • 2,724 Sq Ft
  • $612/SF
  • 15 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1992

  50 Whedon Ln, Madison, CT 06443

  PRIVATE, CUSTOM DESIGNED and SOUND VIEWS! In a world of its own, this 2724 sf retreat gives both complete privacy and a front row seat to an ever changing nature display, south of Route 1. On over 2.5 acres, the original owner was able to bring a forward thinking vision to life with this multi-level transitional home. Offering 3 BR's, options for home office spaces, a heated sunroom, & a private

  Margaret Muir William Pitt Sotheby's Int'l

  50 Whedon Ln, Madison, CT 06443
• 

  Est $701,060 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,472 Sq Ft

  4 Thames Way, Madison, CT 06443

  4 Thames Way, Madison, CT 06443
• 

  

  /4

  $1,890,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  31 Stony Lane Lot 2 Rd, Madison, CT 06443

  Indulge in refined living at our Barberry Farm Open Space subdivision with Waterside Building and Development. Your bespoke home, spanning 3,000 to 4,000+ sq ft, promises not just spacious elegance but high-end finishes and meticulous craftsmanship. Situated within walking distance to Madison beaches and a golf course, this enclave blends luxury with convenience. Revel in the exquisite details of

  Lindsay Greenberg William Raveis Real Estate

  31 Stony Lane Lot 2 Rd, Madison, CT 06443
• 

  $1,050,000 Sold Jun 17, 2025

  • 2,820 Sq Ft
  • $372/SF
  • 27 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2004

  9 Evarts Ln, Madison, CT 06443

  Welcome to The Mews 2 bedroom 2-1/2 bath Luxury Townhome with Attached Garage! Prime in-town Madison location just steps from boutique shopping, fine dining, a world-class bookstore, theatre, and only half a mile from the stunning East Wharf Beach, this home truly defines the best of shoreline living. This expanded open-floor plan offers a blend of elegance, comfort, and functionality. An

  Jamie Lombardy William Pitt Sotheby's Int'l

  9 Evarts Ln, Madison, CT 06443
• 

  Est $1,576,004 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,748 Sq Ft

  2 Race Hill Rd, Madison, CT 06443

  2 Race Hill Rd, Madison, CT 06443
• 

  

  /4

  $1,790,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  31 Stony Lane Lot 6 Rd, Madison, CT 06443

  Indulge in refined living at our Barberry Farm Open Space subdivision with Waterside Building and Development. Your bespoke home, spanning 3,000 to 4,000+ sq ft, promises not just spacious elegance but high-end finishes and meticulous craftsmanship. Situated within walking distance to Madison beaches and a golf course, this enclave blends luxury with convenience. Revel in the exquisite details of

  Lindsay Greenberg William Raveis Real Estate

  31 Stony Lane Lot 6 Rd, Madison, CT 06443
• 

  $505,000 Sold Jun 12, 2025

  • 1,196 Sq Ft
  • $422/SF
  • 27 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1972

  44 Puritan Ln, Madison, CT 06443

  Welcome to this beautifully maintained raised ranch which sits on 1.53 acres, ideally located on a peaceful dead-end street and just minutes to downtown Madison. This home features three spacious bedrooms and one fully renovated bathroom, offering both comfort and style. Inside, you'll find newly refinished hardwood floors, fresh paint throughout, and recessed lighting that adds a modern touch to

  Sandra Ciarleglio William Raveis Real Estate

  44 Puritan Ln, Madison, CT 06443
• 

  Est $681,633 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,877 Sq Ft

  171 Bradley Corners Rd, Madison, CT 06443

  171 Bradley Corners Rd, Madison, CT 06443
• 

  

  /5

  $2,495,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,565 Sq Ft

  31 Stony Lane Lot 3 Rd, Madison, CT 06443

  Indulge in refined living at our Barberry Farm Open Space subdivision with Waterside Building and Development. Your bespoke home, spanning 3,000 to 4,000+ sq ft, promises not just spacious elegance but high-end finishes and meticulous craftsmanship. Situated within walking distance to Madison beaches and a golf course, this enclave blends luxury with convenience. Revel in the exquisite details of

  Lindsay Greenberg William Raveis Real Estate

  31 Stony Lane Lot 3 Rd, Madison, CT 06443
• 

  $550,000 Sold Jun 12, 2025

  • 1,374 Sq Ft
  • $400/SF
  • 18 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  46 Legend Hill Rd, Madison, CT 06443

  Highly coveted ranch style end unit in Legend Hill with partial ocean views. Vaulted ceilings, bright light throughout, a finished & heated walkout basement and brand new carpet make this unit a must-see! The sun-drenched 3 season room boasts bucolic views. Features of the community include a large in-ground pool with a community gathering historic clubhouse with patios, terraces & professionally

  Meg Farmer Coldwell Banker Choice Properties

  46 Legend Hill Rd, Madison, CT 06443
• 

  Est $693,916 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,300 Sq Ft

  140 Saint Francis Woods Rd, Madison, CT 06443

  140 Saint Francis Woods Rd, Madison, CT 06443

Showing Results 281 - 320, Page 8 of 18