Madison, CT Homes

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  $439,999 Under Contract

  • 4 Beds
  • 1 Bath
  • 1,253 Sq Ft

  58 Railroad Ave, Madison, CT 06443

  Nestled on just under an acre in-town, this classic 1930's bungalow offers a rare opportunity to own a piece of Madison's history with endless potential. Whether you are drawn to restoring its original charm or envisioning a brand-new dream home, the setting is perfect for both. Imagine morning strolls on the sidewalk leading you straight into vibrant downtown Madison, afternoons at nearby

  Nancy Leonard William Raveis Real Estate

  58 Railroad Ave, Madison, CT 06443
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  $580,000 Sold Aug 19, 2025

  • 2,256 Sq Ft
  • $257/SF
  • 31 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1985

  73 Legend Hill Rd, Madison, CT 06443

  Welcome to this beautifully maintained two-bedroom, 2.1-bath townhouse condominium in Madison's sought-after Legend Hill community. Set within an 88-acre private enclave of 90 homes, Legend Hill is rich in history and charm, with residences thoughtfully arranged around the historic Northam Manor. Perched on one of the highest elevations between Boston and the New York shoreline, the community

  Dana Weinstein Coldwell Banker Realty

  73 Legend Hill Rd, Madison, CT 06443
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  Est $691,547 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,271 Sq Ft

  56 Walnut Hill Rd, Madison, CT 06443

  56 Walnut Hill Rd, Madison, CT 06443
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  $675,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,028 Sq Ft

  735 Opening Hill Rd, Madison, CT 06443

  This storybook Cape is a hidden treasure, offering 2,000 sq. ft. of character-filled living space plus a heated 975 sq. ft. studio-ideal for work, art, or guests. At its heart lies a true culinary centerpiece: an epicurean's dream kitchen with a 6-burner range, custom finishes, and timeless details that anchor the open floor plan. The main level continues with a welcoming living room and cozy

  Melanie Scull William Pitt Sotheby's Int'l

  735 Opening Hill Rd, Madison, CT 06443
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  $325,000 Sold Aug 19, 2025

  • 1,332 Sq Ft
  • $244/SF
  • 34 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1986

  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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  Est $625,834 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,624 Sq Ft

  119 Squires Rd, Madison, CT 06443

  119 Squires Rd, Madison, CT 06443
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  $749,000 Under Contract

  • 4 Beds
  • 3.5 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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  $212,000 Sold Aug 15, 2025

  • 647 Sq Ft
  • $328/SF
  • 19 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  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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  Est $542,561 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,200 Sq Ft

  83 Squires Rd, Madison, CT 06443

  83 Squires Rd, Madison, CT 06443
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  $525,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,660 Sq Ft

  1071 Durham Rd, Madison, CT 06443

  Charming 3 Bedroom Colonial home with lasting appeal! Step inside to discover nicely refinished hardwood floors that add warmth and character throughout. Updated kitchen with granite countertops and stainless-steel appliances leads to an expansive family room with woodburning fireplace. Home offers newer Anderson windows throughout. Steps to the 2-car attached garage. Unwind on the screened

  Jane Cardarelli William Raveis Real Estate

  1071 Durham Rd, Madison, CT 06443
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  $1,200,000 Sold Aug 15, 2025

  • 4,437 Sq Ft
  • $270/SF
  • 50 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1820

  479 Opening Hill Rd, Madison, CT 06443

  You won't want to miss this move-in ready Colonial-style home, completely renovated in 2021! The property offers over 4,000 square feet of living space, is on more than 3 acres of land, and is conveniently located minutes from the heart of Madison, schools, shopping, I-95 and famous Madison beaches. This 4-bedroom, 2.5-bath home combines traditional charm with beautiful modern updates. The

  Erin Connelly Coldwell Banker Realty

  479 Opening Hill Rd, Madison, CT 06443
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  Est $677,335 Not Listed For Sale

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

  69 Squires Rd, Madison, CT 06443

  69 Squires Rd, Madison, CT 06443
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  $1,300,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,031 Sq Ft

  513 Boston Post Rd, Madison, CT 06443

  Nestled in the heart of Madison Village, this exquisite Greek Revival-style home offers unparalleled privacy. Tucked behind a grove of trees this is a rare find in downtown Madison. Just a short stroll to the Green, downtown shops, golf course and the beaches, this impeccably maintained antique home blends classic charm with modern convenience. Inside, you'll find an open kitchen that flows into

  Meig Walz Newcomb Coldwell Banker Realty

  513 Boston Post Rd, Madison, CT 06443
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  $935,570 Sold Aug 14, 2025

  • 2,728 Sq Ft
  • $343/SF
  • 42 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1854

  109 Boston Post Rd, Madison, CT 06443

  Built in 1854 for the Chittenden family, this historic Madison home sits on a beautifully landscaped, level one-acre lot and blends classic New England charm with modern upgrades. The main residence features three bedrooms on the second floor, plus a finished third-floor loft that serves as a fourth bedroom, office, or playroom. A highlight is the detached oversized garage with a connected studio

  Jack Hill Seabury Hill REALTORS

  109 Boston Post Rd, Madison, CT 06443
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  Est $609,170 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,324 Sq Ft

  57 Squires Rd, Madison, CT 06443

  57 Squires Rd, Madison, CT 06443
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  $630,000 Under Contract

  • 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
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  $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
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  Est $729,801 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,636 Sq Ft

  37 Squires Rd, Madison, CT 06443

  37 Squires Rd, Madison, CT 06443
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  $725,000 Under Contract

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

  677 Durham Rd, Madison, CT 06443

  Absolutely pristine and Stunning 3-Bed, 2.5-Bath Home Built in 2022 - Immaculate and Move-In Ready! This exquisite home just had a pristine inspection with no issues. 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,

  Meig Walz Newcomb Coldwell Banker Realty

  677 Durham Rd, Madison, CT 06443
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  $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
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  Est $795,057 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,753 Sq Ft

  68 Old Toll Rd, Madison, CT 06443

  68 Old Toll Rd, Madison, CT 06443
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  $785,000 Under Contract

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

  48 Shepherds Trail, Madison, CT 06443

  Check out the new fresh photos. 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

  Erin Connelly Coldwell Banker Realty

  48 Shepherds Trail, Madison, CT 06443
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  $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
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  Est $743,512 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,320 Sq Ft

  168 Concord Dr, Madison, CT 06443

  168 Concord Dr, Madison, CT 06443
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  $213,000 Under Contract

  • Land
  • 2.87 Acres
  • $74,216 per Acre

  983 Boston Post Rd, Madison, CT 06443

  983 Boston Post Road, Madison, CT - Walk to Downtown Madison Center. This is a rare opportunity to build the home of your dreams in Madison - one of the most picturesque communities on the Eastern Connecticut Shoreline! Perfect proximity to town, beaches and schools. Madison is acclaimed for having a top ranked school system. A-2 Survey Map with proposed home and septic location on 2.87ac parcel.

  Jennifer Gurnell William Raveis Real Estate

  983 Boston Post Rd, Madison, CT 06443
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  $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
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  Est $868,677 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,004 Sq Ft

  177 Concord Dr, Madison, CT 06443

  177 Concord Dr, Madison, CT 06443
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  $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
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  Est $646,701 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,129 Sq Ft

  53 Heatherwood Dr, Madison, CT 06443

  53 Heatherwood Dr, Madison, CT 06443
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  $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
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  Est $452,514 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  309 Summer Hill Rd, Madison, CT 06443

  309 Summer Hill Rd, Madison, CT 06443
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  $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
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  Est $620,219 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,261 Sq Ft

  307 Summer Hill Rd, Madison, CT 06443

  307 Summer Hill Rd, Madison, CT 06443
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  $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
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  Est $634,709 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  1079 Durham Rd, Madison, CT 06443

  1079 Durham Rd, Madison, CT 06443
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  $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
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  Est $588,680 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,764 Sq Ft

  1065 Durham Rd, Madison, CT 06443

  1065 Durham Rd, Madison, CT 06443
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  $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
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  Est $675,505 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
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  $1,400,000 Sold Aug 01, 2025

  • 5,527 Sq Ft
  • $253/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1991

  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

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