Madison, CT Homes

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  /11

  $1,450,000 Pending

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

  26 Opening Hill Rd, Madison, CT 06443

  2024 is the year to have the home of your dreams! Come see this gorgeous enclave of four to-be-built houses in an ideal location less than 10 minutes from the center of Madison, with restaurants, beaches, shops, and the historic Green all within 5 miles. Surrounded by natural wooded beauty and bordered by Madison Conservation Land, these lots are stunning! Includes all the details you would

  Karen Rosenthal William Raveis Real Estate

  26 Opening Hill Rd, Madison, CT 06443
• 

  $1,060,000 Sold Jun 10, 2025

  • 2,418 Sq Ft
  • $438/SF
  • 74 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2003

  5 Evarts Ln, Madison, CT 06443

  Nestled in the heart of downtown Madison, this stunning townhouse with a freshly painted interior offers the perfect blend of luxury and convenience-just a short stroll from sandy beaches, the library, a cinema, a charming independent bookstore, and an array of shops and restaurants. The beautifully designed kitchen boasts soaring 9'+ ceilings, a SubZero refrigerator, and an inviting eat-in space

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  5 Evarts Ln, Madison, CT 06443
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  Est $636,236 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,980 Sq Ft

  141 Saint Francis Woods Rd, Madison, CT 06443

  141 Saint Francis Woods Rd, Madison, CT 06443
• 

  

  

  /11

  $1,500,000 Pending

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

  38 Opening Hill Rd, Madison, CT 06443

  2024 is the year to have the home of your dreams! Come see this gorgeous enclave of four to-be-built houses in an ideal location less than 10 minutes from the center of Madison, with restaurants, beaches, shops, and the historic Green all within 5 miles. Surrounded by natural wooded beauty and bordered by Madison Conservation Land, these lots are stunning! Includes all the details you would

  Karen Rosenthal William Raveis Real Estate

  38 Opening Hill Rd, Madison, CT 06443
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  $799,000 Sold Jun 09, 2025

  • 1,415 Sq Ft
  • $565/SF
  • 32 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1890

  67 Copse Rd, Madison, CT 06443

  A Picture Perfect Jewel Box! Just a short walk to downtown Madison, the Farmer's market, a bike ride to West Wharf or the Surf Club, and only minutes to 95, this beautifully renovated home (2011) is a GEM! The well appointed kitchen is equipped with stainless Electrolux appliances, a gas cooktop, granite counters, and ample counter space. The open concept living room boasts a gas fireplace,

  Phoebe Finch William Pitt Sotheby's Int'l

  67 Copse Rd, Madison, CT 06443
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  Est $751,462 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,172 Sq Ft

  115 Saint Francis Woods Rd, Madison, CT 06443

  115 Saint Francis Woods Rd, Madison, CT 06443
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  /40

  $2,290,000 Pre-Foreclosure

  • 5 Beds
  • 3 Baths
  • 3,172 Sq Ft

  15 Highland Terrace, Madison, CT 06443

  COME SEE THIS ONE OF KIND FULLY RENOVATED MADISON HOME WITH PRIVATE BEACH RIGHTS!!! Just 300 feet from the sand, this home was once a traditional raised ranch and now has been brilliantly redesigned into a spacious 'elevated ranch' with an open-concept floor plan that feels airy, bright, and made for entertaining! Step into coastal luxury with this fully reimagined Madison home, where every

  John Cronin Century 21 AllPoints Realty

  15 Highland Terrace, Madison, CT 06443
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  $620,000 Sold Jun 06, 2025

  • 1,748 Sq Ft
  • $355/SF
  • 2 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2018

  67 Boston Post Rd Unit 1-1, Madison, CT 06443

  Welcome to 67 Boston Post Road, Unit #11 - a stunning, turn-key luxury residence that perfectly blends modern comfort with timeless elegance. Nestled in one of Madison's most sought-after communities, this exquisite home is just minutes from the charming Madison town center and the picturesque Guilford Green. Step inside to discover a spacious open-concept layout featuring gleaming hardwood

  Matt Healy Coldwell Banker Realty

  67 Boston Post Rd Unit 1-1, Madison, CT 06443
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  Est $789,683 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,180 Sq Ft

  7 Williamsburg Cir, Madison, CT 06443

  7 Williamsburg Cir, Madison, CT 06443
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  /31

  $825,000 Pre-Foreclosure

  • 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
• 

  $120,000 Sold Jun 06, 2025

  • 680 Sq Ft
  • $176/SF
  • 244 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1940

  12 North St, Madison, CT 06443

  Charming and turn-key, this lovely, seasonal Madison cottage located on leased land is minutes to Hammonasset State Park with its sandy beaches and sparkling salt waters of Long Island Sound. Path to the beach is 1 mile to the water's edge. Hammonasset State Park is one on Connecticut's gems! It has 2 miles of sandy beaches, numerous walking/biking paths, and a wildlife sanctuary with 936 acres

  Jane Cardarelli William Raveis Real Estate

  12 North St, Madison, CT 06443
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  Est $734,333 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,938 Sq Ft

  24 Lyle Dr, Madison, CT 06443

  24 Lyle Dr, Madison, CT 06443
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  /40

  $549,500 Open Sat 12PM - 2PM

  • 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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  $578,000 Sold Jun 05, 2025

  • 1,404 Sq Ft
  • $412/SF
  • 67 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1968

  100 Warpas Rd, Madison, CT 06443

  Nestled on a lightly wooded and private lot in Madison, this charming 3-bedroom, 2.5-bath split-level home offers a perfect blend of comfort and convenience. Just minutes from I-95, route 1, schools, beaches and downtown. The home features beautiful hardwood floors throughout. The main level of the home boasts a spacious living and dining room-ideal for gatherings and entertaining. Elegant

  Erin Connelly Coldwell Banker Realty

  100 Warpas Rd, Madison, CT 06443
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  Est $705,607 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,004 Sq Ft

  524 Opening Hill Rd, Madison, CT 06443

  524 Opening Hill Rd, Madison, CT 06443
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  /21

  $600,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,853 Sq Ft

  7 Downing Way, Madison, CT 06443

  Riverside elegance with marshland serenity! Nestled within the tranquil enclave of the Windermere West Association, this exquisite townhouse condo presents a rare opportunity to embrace riverfront living at its finest. The second floor has 2 large bedrooms and 2 bathrooms, office space/upstairs family room, laundry and plentiful attic storage. There are sweeping vistas of the Hammonasset River

  Margaret Muir William Pitt Sotheby's Int'l

  7 Downing Way, Madison, CT 06443
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  $700,000 Sold Jun 04, 2025

  • 1,854 Sq Ft
  • $378/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1976

  15 Pepperwood Ct, Madison, CT 06443

  ***Highest & Best Due Monday (4/28 at 8 pm!!}*** Welcome to 15 Pepperwood Ct., an 1854-square-foot colonial that awaits its new owners. This four-bedroom, two-and-a-half-bathroom colonial features hardwood floors throughout, creating an inviting ambiance. The updated Chefs kitchen is equipped with granite countertops, GE Profile SS double wall ovens, New Whirlpool SS double-door refrigerator with

  Joe Scarpellino Coldwell Banker Realty

  15 Pepperwood Ct, Madison, CT 06443
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  Est $740,058 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,380 Sq Ft

  579 Opening Hill Rd, Madison, CT 06443

  579 Opening Hill Rd, Madison, CT 06443
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  /36

  $589,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 1,792 Sq Ft

  338 Opening Hill Rd, Madison, CT 06443

  Extensively updated ranch offering effortless one-level living! This charming 4-bedroom, 2.5-bath home features many recent improvements, including a new roof with skylights, extensive landscaping, LeafGuard gutters, refinished floors, updated kitchen and bathrooms, garage doors, fresh paint, a new well tank and pump and more. Enjoy central air, a bonus three-season room (perfect office), fire

  Barbara Goetsch William Pitt Sotheby's Int'l

  338 Opening Hill Rd, Madison, CT 06443
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  $693,000 Sold Jun 03, 2025

  • 2,030 Sq Ft
  • $341/SF
  • 24 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1983

  68 White Cedar Dr, Madison, CT 06443

  Please have all offers in by Tuesday at noon. Tucked away at the end of a peaceful cul-de-sac in Madison, this impeccably maintained three-bedroom home offers both comfort and charm in equal measure. Set on a generous, beautifully landscaped lot, the property boasts a spacious yard perfect for outdoor living, gardening, or simply relaxing in your own private oasis. Step inside to discover a home

  Meig Walz Newcomb Coldwell Banker Realty

  68 White Cedar Dr, Madison, CT 06443
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  Est $615,924 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,077 Sq Ft

  15 Scenic Rd, Madison, CT 06443

  15 Scenic Rd, Madison, CT 06443
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  /38

  $569,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,593 Sq Ft

  87 Legend Hill Rd Unit 87, Madison, CT 06443

  Welcome to 87 Legend Hill Road at Legend Hill in Madison, CT! This bright and beautiful 2 bedroom, 2.5 bath ranch townhome features an open floor plan with hardwood floors and vaulted, 9+ foot ceilings throughout the living and dining room. Right off the dining room is the gorgeous sunroom to sip your morning coffee or tea. The kitchen features ample counter space and cabinets, with an eating

  Tyler Della Valle Dow Della Valle

  87 Legend Hill Rd Unit 87, Madison, CT 06443
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  $700,000 Sold Jun 02, 2025

  • 2,008 Sq Ft
  • $349/SF
  • 8 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1968

  14 Timber Ridge Rd, Madison, CT 06443

  Welcome Home to This Charming, Move-In Ready Madison Gem! Located on a quiet cul-de-sac just minutes from town and Madison's beautiful beaches, this meticulously maintained home offers the perfect blend of classic charm and modern updates. The sun-drenched, remodeled kitchen features high-end appliances, including a Sub-Zero refrigerator, Thermador dual-fuel 5-burner range, and quartz

  Alicia Mahon William Pitt Sotheby's Int'l

  14 Timber Ridge Rd, Madison, CT 06443
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  Est $925,793 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,678 Sq Ft

  596 Opening Hill Rd, Madison, CT 06443

  596 Opening Hill Rd, Madison, CT 06443
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  /38

  $729,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,068 Sq Ft

  259 Mungertown Rd, Madison, CT 06443

  Beautifully renovated Madison Ranch that seamlessly blends California chic with East Coast charm. This home is anchored by a stunning kitchen with an oversized island that opens to a very pretty family room with a gorgeous stone fireplace. The impressive Great Room features a vaulted ceiling with architecturally intriguing beams, sliders to the stone patio, a stunning original fireplace and is

  Phoebe Finch William Pitt Sotheby's Int'l

  259 Mungertown Rd, Madison, CT 06443
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  $250,000 Sold May 30, 2025

  • 764 Sq Ft
  • $327/SF
  • 4 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1986

  51 Brantwood Dr, Madison, CT 06443

  Now offering, a charming one-bedroom, ranch-style condo. This bright and airy second-floor end unit features a spacious living room filled with natural light and a generous eat-in kitchen. The large bedroom includes two closets, and the full bathroom offers a convenient tub/shower combination. Step out onto a private deck to enjoy the outdoor space. Located just minutes from downtown Madison,

  Rob McConville William Pitt Sotheby's Int'l

  51 Brantwood Dr, Madison, CT 06443
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  Est $536,592 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft

  101 Winding Rd, Madison, CT 06443

  101 Winding Rd, Madison, CT 06443
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  /30

  $549,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,905 Sq Ft

  531 Green Hill Rd, Madison, CT 06443

  Quite Pretty! This charming Madison Colonial features 3 bedrooms, 1.5 baths, a smart and versatile floor plan and is filled with natural light and timeless charm. This happy home has been entirely repainted and has beautifully refinished hardwood floors in the living room, dining room, and bedrooms. Formal crown molding and built in cabinetry adds an elegant touch throughout. The kitchen features

  Phoebe Finch William Pitt Sotheby's Int'l

  531 Green Hill Rd, Madison, CT 06443
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  $400,000 Sold May 30, 2025

  • 2,446 Sq Ft
  • $164/SF
  • 35 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1975

  98 Bartlett Dr, Madison, CT 06443

  Presenting 98 Bartlett Drive, a colonial style home with boundless potential, nestled in the charming town of Madison, CT. This 3-bedroom, 2.5-bath home offers a canvas for those with a vision to create their dream space, complete with a detached two-car garage featuring an unfinished walk-up attic for additional storage or future expansion. The home's versatile layout includes a spacious living

  Nikki Travaglino William Pitt Sotheby's Int'l

  98 Bartlett Dr, Madison, CT 06443
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  Est $472,763 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,884 Sq Ft

  123 Deepwood Dr, Madison, CT 06443

  123 Deepwood Dr, Madison, CT 06443
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  /37

  $2,390,000 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,160 Sq Ft

  86B E Wharf Rd, Madison, CT 06443

  Welcome to your coastal paradise! This exquisite home is ideally located a short stroll from the beach and town, offering the ultimate coastal lifestyle. Built in 2017, this 4-bedroom gem boasts exceptional craftsmanship and sophisticated design, highlighted by custom millwork and finishes that create a peaceful atmosphere. The open-concept floor plan flows effortlessly, with a stunning living

  Dean Mitchell William Pitt Sotheby's Int'l

  86B E Wharf Rd, Madison, CT 06443
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  $705,000 Sold May 30, 2025

  • 2,840 Sq Ft
  • $248/SF
  • 33 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1972

  13 Old Toll Rd, Madison, CT 06443

  Welcome to your own private retreat - 13 Old Toll Rd., Madison! Stunning updated home with Iron Stream Views! This captivating colonial sits on a serene, level lot with a tranquil stream bordering the rear of the property, feeding into picturesque Dream Lake. Perfectly blending luxury and comfort, this home is a true escape. Step into the gourmet kitchen, a chef's dream with granite countertops,

  Allison Ciarcia William Raveis Real Estate

  13 Old Toll Rd, Madison, CT 06443
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  Est $507,988 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,832 Sq Ft

  105 Deepwood Dr, Madison, CT 06443

  105 Deepwood Dr, Madison, CT 06443
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  /20

  $797,900 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,039 Sq Ft

  72 Kelsey Springs Dr, Madison, CT 06443

  Welcome to 72 Kelsey Springs Dr in beautiful Madison, CT! This charming 4-bedroom, 2.5-bath colonial offers over 2,500 sq ft of living space with serene pond views and a peaceful 1-acre level lot in a sought-after neighborhood. Step inside to find a warm and inviting layout perfect for everyday living and entertaining. The spacious kitchen flows into a cozy family room, while the formal dining

  Nick Prevost William Raveis Real Estate

  72 Kelsey Springs Dr, Madison, CT 06443
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  $850,000 Sold May 28, 2025

  • 1,037 Sq Ft
  • $820/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1940

  63 Circle Beach Rd, Madison, CT 06443

  Discover the charm of DIRECT WATERFRONT living with this circa 1940 cottage, perfectly situated on a .11-acre sandy beach along the shores of Long Island Sound. Featuring 3 bedrooms and 2 full baths, this 1,000+ SF home offers a seamless blend of coastal charm and modern convenience, including mini split systems for heating and cooling. The open-concept kitchen, dining, and living areas are

  Rose Ciardiello William Raveis Real Estate

  63 Circle Beach Rd, Madison, CT 06443
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  Est $536,587 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,432 Sq Ft

  99 Deepwood Dr, Madison, CT 06443

  99 Deepwood Dr, Madison, CT 06443
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  /40

  $769,900 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,916 Sq Ft

  73 Devonshire Ln, Madison, CT 06443

  Wow-this home truly has it all, with no detail overlooked. Set on nearly 2 acres of private, manicured grounds, this light-filled 4-bedroom colonial offers a perfect blend of comfort and style. The main floor features gleaming hardwood floors and an ideal layout. A large living room with a gas fireplace that flows seamlessly into an incredible family room with vaulted ceilings and its own heating

  Susan Santoro William Pitt Sotheby's Int'l

  73 Devonshire Ln, Madison, CT 06443
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  $543,800 Sold May 21, 2025

  • 1,932 Sq Ft
  • $281/SF
  • 194 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1994

  6 Apple Way, Madison, CT 06443

  Welcome to the pick of the crop at The Orchards, 6 Apple Way. This in-town stand alone home is being offered for the first time in 28 years. Its ideal location is close to beaches, train station, restaurants and so much more. With newer appliances, less than 5 years old hot water heater, a/c compressors, and Generac generator you will be pleased with the maintenance record. One of the largest

  Julie Ovian William Pitt Sotheby's Int'l

  6 Apple Way, Madison, CT 06443
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  Est $700,668 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,993 Sq Ft

  29 Milano Pond Dr, Madison, CT 06443

  29 Milano Pond Dr, Madison, CT 06443
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  /39

  $525,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,663 Sq Ft

  691 Green Hill Rd, Madison, CT 06443

  Plenty of sun shines into this 3-bedroom, 1.5-bath Tudor-style home. That's most obvious when you enter the tiled foyer and step right into the family room, brightened by a panoramic picture window and warmed by a wood fireplace. Windows light up the adjoined living room and dining room, too, accenting high ceilings, hardwood floors and wall paneling. The remodeled kitchen includes new

  Sue Woods William Pitt Sotheby's Int'l

  691 Green Hill Rd, Madison, CT 06443

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