Madison, CT Homes

• 

  $761,000 Sold Aug 14, 2025

  • 2,989 Sq Ft
  • $255/SF
  • 46 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1984

  37 Sheffield Ln, Madison, CT 06443

  Welcome home! This lovingly maintained 4-bedroom colonial is Located at the end of a beautiful cul-de-sac neighborhood only 15 minutes to the quaint Madison downtown and its beaches. Plenty of room for everyone including the family dog in this 2377 square foot home with finished walkout basement and invisible fence. Hardwood floors throughout with a lovely woodburning woodstove in the family

  Jane Cardarelli William Raveis Real Estate

  37 Sheffield Ln, Madison, CT 06443
• 

  Est $596,200 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,052 Sq Ft

  69 Mendingwall Cir, Madison, CT 06443

  69 Mendingwall Cir, 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
• 

  $690,000 Sold Aug 13, 2025

  • 3,120 Sq Ft
  • $221/SF
  • 33 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1966

  41 Sportsman Hill Rd, Madison, CT 06443

  Welcome to this spacious and versatile Colonial home located less than 2 miles from charming downtown Madison, CT. With 4-5 bedrooms, 3.1 baths, and three fireplaces, this home offers the perfect blend of classic elegance and modern functionality. The large living room with fireplace is ideal for gatherings, while the inviting family room features built-in cabinetry, bookshelves, a cozy

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  41 Sportsman Hill Rd, Madison, CT 06443
• 

  Est $664,064 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,646 Sq Ft

  7 Twilight Dr, Madison, CT 06443

  7 Twilight Dr, 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
• 

  $1,350,000 Sold Aug 12, 2025

  • 3,569 Sq Ft
  • $378/SF
  • 41 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2015

  78 Wildcat Springs Dr, Madison, CT 06443

  Unlike anything else on the market in Madison! This truly exceptional 2015 Colonial sits on a beautifully landscaped 1.41-acre lot featuring a resort-style infinity saltwater pool, fire pit, private association pond, dock and immaculate landscaping. Private, elegant, pristinely maintained, thoughtfully updated, in a highly desirable neighborhood AND just minutes to everything, this one is a WOW!

  Phoebe Finch William Pitt Sotheby's Int'l

  78 Wildcat Springs Dr, Madison, CT 06443
• 

  Est $594,551 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,740 Sq Ft

  1474 Durham Rd, Madison, CT 06443

  1474 Durham Rd, 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
• 

  $225,000 Sold Aug 11, 2025

  • 863 Sq Ft
  • $261/SF
  • 47 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1986

  28 Brantwood Dr, Madison, CT 06443

  Charming 1-Bedroom Condo with Spacious Layout in Prime Madison Location! Welcome to this beautifully designed 1-bedroom, 1-bath condo offering a thoughtfully laid-out living space with an open and airy feel. Step into a bright and expansive living room, perfect for entertaining or relaxing, with plenty of space for both lounging and dining. The kitchen features a functional layout with generous

  Jules Gaughran - Etes William Pitt Sotheby's Int'l

  28 Brantwood Dr, Madison, CT 06443
• 

  Est $576,700 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,908 Sq Ft

  34 Great Meadow Rd, Madison, CT 06443

  34 Great Meadow Rd, 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
• 

  $648,500 Sold Aug 08, 2025

  • 1,668 Sq Ft
  • $389/SF
  • 60 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1976

  94 Boston Post Rd, Madison, CT 06443

  UNIQUE CONTEMPORARY HOME SURROUNDED BY NATURE. CONVENIENTLY LOCATED IN SMALL ENCLAVE OF THREE HOMES, SET BACK OFF THE BOSTON POST ROAD. COMPLETELY RENOVATED IN 2013-2015. NEW ROOF, KITCHEN, BATHS, FLOORING, HEATING, A/C, WINDOWS, STAIRCASE, LIGHTING,ELECTRICAL , TONGUE AND GROOVE PINE VAULTED CEILING, AND MORE. LIKE WALKING IN ARCHITECTAUL DIGEST MAGAIZINE! FIRST FLOOR MASTERBEDROOM WITH GORGEOUS

  Camille Ackermann Berkshire Hathaway NE Prop.

  94 Boston Post Rd, Madison, CT 06443
• 

  Est $530,695 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  1477 Durham Rd, Madison, CT 06443

  1477 Durham Rd, 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
• 

  $692,000 Sold Aug 08, 2025

  • Land
  • 1 Acre
  • $692,000 per Acre

  • 156 Days On Market

  00 Stone Rd, Madison, CT 06443

  Discover the perfect opportunity to build your dream home on this exceptional buildable lot, offering coveted deeded beach rights. Nestled in a prime location, this property provides direct access to pristine Madison shore, allowing you to enjoy the beauty of coastal living every day. Whether you're looking to create a private retreat, or a vacation/second home, this lot offers unlimited

  Betsy Anderson William Pitt Sotheby's Int'l

  00 Stone Rd, Madison, CT 06443
• 

  Est $410,443 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,611 Sq Ft

  1467 Durham Rd, Madison, CT 06443

  1467 Durham Rd, 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
• 

  $705,000 Sold Aug 07, 2025

  • 1,840 Sq Ft
  • $383/SF
  • 17 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1967

  118 Flintlock Rd, Madison, CT 06443

  Mid century modern, custom designed and built expanded ranch surrounded by many mature plantings provides sought after one level living. Wonderful open floor plan with picture windows in the living room and eat-in kitchen/dining area look onto the lovely rolling front lawn. A large bar is conveniently located in the kitchen designed for more casual dining. Six rooms, 3 bedrooms and 2 full baths.

  Faith Whitehead William Raveis Real Estate

  118 Flintlock Rd, Madison, CT 06443
• 

  Est $745,229 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  24 Genesee Ln, Madison, CT 06443

  24 Genesee Ln, Madison, CT 06443
• 

  

  /21

  $525,000

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  7 Madrina Ln, Madison, CT 06443

  Introducing a charming and well-maintained raised ranch home, nestled in the heart of shoreline Madison. Here at 7 Madrina Lane, step into an inviting living room with fireplace, and newer kitchen equipped with stainless steel appliances. Boasting 3 bedrooms, and pristine hardwood flooring - this delightful residence offers a cozy, spacious environment for everyday living. The rear covered deck

  Kayla Chasse Compass Connecticut, LLC

  7 Madrina Ln, Madison, CT 06443
• 

  $510,000 Sold Aug 04, 2025

  • 1,680 Sq Ft
  • $304/SF
  • 95 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1977

  11 Strathmore Ln, Madison, CT 06443

  Meticulously maintained townhouse condo now available. Two bedrooms (office serving as a 3rd bedroom) bright & sunny kitchen, combined living & dining room, family room w/sliders out to private patio, one car attached garage w/additional parking. Savor the best of indoor and outdoor living minutes to beaches, restaurants, world famous RJ Julia Bookstore, library, train and commuter routes. Just

  Pam Kadamus William Pitt Sotheby's Int'l

  11 Strathmore Ln, Madison, CT 06443
• 

  Est $1,017,861 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,680 Sq Ft

  163 Genesee Ln, Madison, CT 06443

  163 Genesee Ln, Madison, CT 06443
• 

  

  /34

  $699,900 Open Sun 12PM - 2PM

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

  42 Buck Hill Rd, Madison, CT 06443

  This is the Madison home you have been waiting for!! Tucked away on 1.88 acres of level land in one of the area's most beautiful neighborhoods, this 4-bedroom colonial offers the perfect blend of privacy & convenience. 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

  Susan Santoro William Pitt Sotheby's Int'l

  42 Buck Hill Rd, Madison, CT 06443
• 

  $875,000 Sold Aug 01, 2025

  • 2,804 Sq Ft
  • $312/SF
  • 23 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1976

  31 Pine Dr, Madison, CT 06443

  Set on quiet cul-de-sac, so convenient to everything Madison has to offer, this immaculate well maintained Colonial is move in condition! The private home itself is set back from the road, w/ gorgeous landscaping & an impressive stone walk up to the welcoming & covered front entryway. Once inside the spacious foyer, there is a comfortable office or first floor guest room w/ custom built-ins, a

  Todd Gould William Pitt Sotheby's Int'l

  31 Pine Dr, Madison, CT 06443
• 

  Est $950,655 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,366 Sq Ft

  145 Genesee Ln, Madison, CT 06443

  145 Genesee Ln, Madison, CT 06443
• 

  

  /33

  $450,000 Open Sun 12PM - 2PM

  • 1 Bed
  • 1 Bath
  • 784 Sq Ft

  24 Pent Rd, Madison, CT 06443

  Fulfill your dream of having a beach cottage just steps to one of Madison's finest beaches. This precious little home has been loved by the same family for decades and now it is ready for someone new to cherish. With one bedroom and bathroom on the main floor and finished attic space for overflow guests, you won't want to be anywhere else during summer months. You may access the Shoreline

  Julie Ovian William Pitt Sotheby's Int'l

  24 Pent Rd, Madison, CT 06443
• 

  $1,350,000 Sold Aug 01, 2025

  • 2,610 Sq Ft
  • $517/SF
  • 284 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1830

  108 Neck Rd, Madison, CT 06443

  TWO HOUSES SITED ON ONE BEAUTIFUL RIVERFRONT PROPERTY WITH 4000+ SF OF LIVING SPACE! Both charming, historic houses are on 1.1 acres with mesmerizing views of the Neck River. The main house, built c.1830 in the Federal style by shipbuilder Ellsworth Bassett, has been renovated for a modern look but retains its historic charm. Off the foyer, you'll find the LR with its impressive granite FP & the

  Margaret Muir William Pitt Sotheby's Int'l

  108 Neck Rd, Madison, CT 06443
• 

  Est $1,321,399 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 6,267 Sq Ft

  546 Summer Hill Rd, Madison, CT 06443

  546 Summer Hill Rd, Madison, CT 06443
• 

  

  /40

  $699,000

  • 3 Beds
  • 3 Baths
  • 2,025 Sq Ft

  69 Squires Rd, Madison, CT 06443

  This beautifully renovated modern home offers 2,025 sq ft of modern living with every upgrade already done for you. Set on over an acre of level land on a quiet street, the home features 3 bedrooms and 3 full baths, including a first-floor primary suite with its own fireplace, patio access, and spa-like bath with heated floors. The open floor plan is bright and welcoming, enhanced by new hardwood

  Sue Woods William Pitt Sotheby's Int'l

  69 Squires Rd, Madison, CT 06443
• 

  $515,000 Sold Jul 31, 2025

  • 1,860 Sq Ft
  • $277/SF
  • 21 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1977

  381 Horse Pond Rd, Madison, CT 06443

  Nestled in the heart of Madison, Connecticut, on a peaceful acre of level land, there's a two-bedroom ranch that tells a story of comfort, charm, and possibility. From the moment you arrive, you feel the space breathe. The flat, open yard invites summer cookouts, garden beds, or perhaps a hammock strung between trees. It's the kind of land that welcomes laughter, creativity, and calm-where young

  Lisa Daniele William Raveis Real Estate

  381 Horse Pond Rd, Madison, CT 06443
• 

  Est $862,173 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,177 Sq Ft

  29 Bridle Path Ln, Madison, CT 06443

  29 Bridle Path Ln, Madison, CT 06443
• 

  

  /36

  $725,000 Open Sat 1:30PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,283 Sq Ft

  14 Horseshoe Ln, Madison, CT 06443

  Close to town, on a quiet cul de sac, sits this 2300 sf one floor custom home with an additional 300 sf three season sun room (with propane stove) in a lush, very private setting. This gracious home is situated on over an acre of private mature landscaped grounds, including a tennis court (needs some work), offering privacy while still part of a cul de sac neighborhood. Freshly painted inside and

  Peter O'Donnell Sunset Creek Realty, LLC

  14 Horseshoe Ln, Madison, CT 06443
• 

  $770,000 Sold Jul 31, 2025

  • 2,356 Sq Ft
  • $327/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  24 Grouse Ln, Madison, CT 06443

  Contemporary comfort meets timeless charm in this beautifully designed home featuring an open floor, a spacious living room with a cozy fireplace, while the sun-filled family room boasts walls of windows with tranquil view of the lush backyard adjacent to a conservation parcel. The gourmet kitchen includes granite countertops, stainless steel appliances, Cherry cabinets, wet bar, Bosch - two

  Sharon Linder Berkshire Hathaway NE Prop.

  24 Grouse Ln, Madison, CT 06443
• 

  Est $1,331,363 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,915 Sq Ft

  561 Summer Hill Rd, Madison, CT 06443

  561 Summer Hill Rd, Madison, CT 06443
• 

  

  /40

  $4,500,000

  • 5 Beds
  • 4.5 Baths
  • 4,613 Sq Ft

  33 Seaview Ave, Madison, CT 06443

  Stunning one-of-a-kind residence designed by Robert Page, AIA. Set directly on coveted private assoc. Seaview Beach, this iconic 4-level 4,600+ sq. ft. coastal retreat offers an unparalleled blend of modern sensibility and timeless craftmanship. Largely renovated in 2023, no detail was overlooked in this luxurious sanctuary for those who want the exceptional in coastal living. No flood insurance

  Margaret Muir William Pitt Sotheby's Int'l

  33 Seaview Ave, Madison, CT 06443
• 

  $705,000 Sold Jul 30, 2025

  • 2,762 Sq Ft
  • $255/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1991

  14 Martleshamheath Ln, Madison, CT 06443

  Nestled in Desired Neighborhood Beautiful Updated Colonial on 3.46-acres on a quiet cul-de-sac in Seaside Town of Madison. Open casual living, formal spaces, walkout lower level: Natural light fills this home. 2 story Foyer invites you into a Lovely Home offering Dine in Kitchen, Island, Granite, tile, double stainless sink & appliances, recess lighting: Powder Room, Formal Dining & Living Rooms

  Karen Martin Century 21 AllPoints Realty

  14 Martleshamheath Ln, Madison, CT 06443
• 

  Est $912,147 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,765 Sq Ft

  22 Northwood Rd, Madison, CT 06443

  22 Northwood Rd, Madison, CT 06443
• 

  

  /37

  $637,500 Open Sun 11AM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,088 Sq Ft

  81 Bartlett Dr, Madison, CT 06443

  81 Bartlett - a rare find, showcasing a blend of modern updates & outdoor amenities that make it perfect for entertaining & everyday living. Step outside to the double decks that meet with a new patio area & the expansive, level, private backyard offers a lush, grassy yard. Inside, the home greets you with an inviting colonial style layout. The foyer flows seamlessly into both the formal living

  Lauren Freedman Coldwell Banker Realty

  81 Bartlett Dr, Madison, CT 06443
• 

  $1,200,000 Sold Jul 30, 2025

  • 2,375 Sq Ft
  • $505/SF
  • 47 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1920

  290 Neck Rd, Madison, CT 06443

  Welcome to your dream coastal home, nestled in the picturesque town of Madison, Connecticut. This 3-bedroom residence offers stunning Neck River views, Long Island Sound views, marsh vistas and membership to The Highlands East River Civic Corp Beach. Step into the home and be greeted by the wrap around the sun porch that leads into the living room with a wood-burning fireplace and beautiful wood

  Amy Kirst William Pitt Sotheby's Int'l

  290 Neck Rd, Madison, CT 06443

Showing Results 121 - 160, Page 4 of 18