Madison, CT Homes

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  /40

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 3,711 Sq Ft

  1543 Durham Rd, Madison, CT 06443

  Bring your imagination! This spacious home offers 3 bedrooms and 2.5 bathrooms, ready for your vision and updates. Featuring classic architectural details, generous room sizes, and a functional floor plan, this property has great bones and endless potential. The main level includes a large living room, formal dining area, and a kitchen ready for redesign. Upstairs, you'll find three comfortable

  

  Rob McConville

  William Pitt Sotheby's Int'l

  (475) 290-6326

  1543 Durham Rd, Madison, CT 06443
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  Explore Madison

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  /40

  $4,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,809 Sq Ft
  • House for Rent

  156 Concord Dr, Madison, CT 06443

  Quintessential New England Cape on over an acre, situated perfectly to enjoy the serene natural beauty of North Madison, while being only minutes from downtown or Madison beaches. Main level of the house features hardwood floors throughout an incredibly versatile floorplan with multiple living areas, large newly updated kitchen, dining room (or den) and convenient half bath... as well as 2 wood

  

  Jared Verrillo

  Seabury Hill REALTORS

  (475) 281-3505

  156 Concord Dr, Madison, CT 06443
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  $625,000 Sold Sep 17, 2025

  • 1,921 Sq Ft
  • $325/SF
  • 32 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  181 Ridge Rd, Madison, CT 06443

  Welcome to this beautifully renovated Mid-Century split-level home, thoughtfully updated to offer modern comfort and style throughout. The open-concept layout features gleaming hardwood floors, a granite kitchen with newer SS appliances, and fully remodeled bathrooms. A spacious three-season porch off the dining area provides a versatile bonus space-currently used as a home gym and playroom, can

  Renee Autorino Coldwell Banker Realty

  181 Ridge Rd, Madison, CT 06443
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  Est $859,994 Not Listed For Sale

  2 Grove Ave, Madison, CT 06443

  2 Grove Ave, 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 Brick English Georgian 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

  

  Ron Stewart

  Houlihan Lawrence WD

  (475) 405-2519

  24 Indigo Trail, Madison, CT 06443
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  /14

  $2,500 per month

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft
  • House for Rent

  49 Cottage Rd, Madison, CT 06443

  Welcome to your ideal rental property in Madison, CT! This charming home offers a wonderful opportunity for comfortable living in a vibrant community. Located just minutes away from several great restaurants and a nearby department store, convenience is at your doorstep. Enjoy the natural beauty of Hammonasset Beach State Park, perfect for leisurely walks and relaxation.While specific

  49 Cottage Rd, Madison, CT 06443
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  $835,000 Sold Sep 15, 2025

  • 2,568 Sq Ft
  • $325/SF
  • 19 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2002

  35 Bishop Ln, Madison, CT 06443

  Welcome to 35 Bishop Ln, Madison-a beautifully remodeled haven that embodies elegance & comfort. Its proximity to town (only 1.7 miles), Madison Beaches (including Hammonasset State Pk only 2.8 miles away) & the local swim & racquet club adds to the appeal, making this property the ultimate retreat. This stunning home offers 2,568sf of refined living space, w/an additional 852sf in the finished

  Lisa Rollins Team Compass Connecticut, LLC

  35 Bishop Ln, Madison, CT 06443
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  Est $191,575 Not Listed For Sale

  2117 Durham Rd, Madison, CT 06443

  2117 Durham Rd, Madison, CT 06443
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  /39

  $1,295,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,580 Sq Ft

  110 E Wharf Rd, Madison, CT 06443

  Steps to the Shoreline - Four-Bedroom Beach Retreat with Deeded Beach Right Away! Tucked away on a serene interior lot in Madison's coveted East Wharf neighborhood, this four-bedroom, two-bath coastal gem blends timeless seaside charm with modern comfort-plus valuable income-producing potential. With a deeded beach right away, your days can begin and end just steps from a sandy, private,

  

  Lisa Daniele

  William Raveis Real Estate

  (203) 689-0705

  110 E Wharf Rd, Madison, CT 06443
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  /30

  $2,900 per month

  • 2 Beds
  • 1 Bath
  • 891 Sq Ft
  • House for Rent

  40 Whedon Ln, Madison, CT 06443

  Great location! Academic rental available October 3-May 31. Just five minutes to beaches and Madison village center, this home is completely updated and fully furnished, including linens and all kitchen utensils. Stylish 2 bedroom/ 1 bath ranch in quiet location at the end of a private road, south of the Boston Post Rd. Remodeled with white Shaker cabinets, quartz counters, stainless steel

  Jorge Zea Blue Lighthouse Realty, Inc

  40 Whedon Ln, Madison, CT 06443
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  $580,000 Sold Sep 15, 2025

  • 1,955 Sq Ft
  • $297/SF
  • 16 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1964

  37 Riverside Terrace, Madison, CT 06443

  This cozy 3-bedroom, 2.5-bath raised ranch sits on a generous lot in a highly sought-after neighborhood, just minutes from schools, I-95, Route One, town conveniences, and the shoreline. A newly installed stone step entrance adds curb appeal and a welcoming touch as you approach the home. The main level welcomes you with a bright and airy atmosphere, enhanced by hardwood floors throughout. A

  Erin Connelly Coldwell Banker Realty

  37 Riverside Terrace, Madison, CT 06443
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  24 Wilshire Rd Unit 24A, Madison, CT 06443

  24 Wilshire Rd Unit 24A, Madison, CT 06443
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  /40

  $849,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3 Baths
  • 2,576 Sq Ft

  15 Buttonball Ln, Madison, CT 06443

  Stunning Contemporary Home with Ultimate Outdoor Oasis! This beautifully updated contemporary-style home truly has it all-ideally located in a desirable neighborhood close to town and schools. Inside, you'll find 4 spacious bedrooms and 3 full bathrooms, including a luxurious primary suite featuring a gas fireplace, generous walk-in closets, and a spa-inspired bathroom. The heart of the home is

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 264-6914

  15 Buttonball Ln, Madison, CT 06443
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  /22

  $4,000 per month

  • 4 Beds
  • 1.5 Baths
  • 2,458 Sq Ft
  • House for Rent

  29 Flintlock Rd, Madison, CT 06443

  Spacious 4-bedroom colonial with pool in prime location! This inviting 4-bedroom Colonial offers the perfect balance of comfort and convenience. The first floor features hardwood floors, a welcoming living room with fireplace, and a bright family room set just off the kitchen. With two pocket doors, the family room can be opened for gatherings or closed off for privacy. Upstairs, you'll find four

  Emily Lovejoy William Raveis Real Estate

  29 Flintlock Rd, Madison, CT 06443
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  $187,000 Sold Sep 12, 2025

  • 470 Sq Ft
  • $398/SF
  • 110 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1950

  28 1st St, Madison, CT 06443

  Delightful seasonal(4/1-10/31)storybook cottage located in a vintage beach community nestled on leased land located in the picturesque coastal town of Madison Ct. This unique village is on 6 acres situated adjacent to the sandy stretch of Long Island Sounds Hammonassett State Park, Salt Meadow Park (includes dog park) & the Greenway trail. You will be greeted by a freshly painted (exterior)home

  Karen Bruno Roos Williams Real Estate

  28 1st St, Madison, CT 06443
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  Est $2,214,772 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 4,077 Sq Ft

  11 Alexandra Ln, Madison, CT 06443

  11 Alexandra Ln, Madison, CT 06443
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  /40

  $2,000,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 4,988 Sq Ft

  123 Liberty St, Madison, CT 06443

  Welcome to Liberty Street - One of Madison's Most Coveted Locations. This custom-built home blends grace, elegance, and exceptional craftsmanship with exquisite millwork and fine finishes. Enjoy warm summer nights on the charming covered front porch. Inside, wide-plank hardwood floors, a coffered dining room ceiling, and a chef's kitchen with sunny dining area and 8-burner Wolf dual-fuel range

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 241-7103

  123 Liberty St, Madison, CT 06443
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  /19

  $1,800 per month

  • 1 Bed
  • 1 Bath
  • 1,340 Sq Ft
  • Townhouse for Rent

  21 Copse Rd, Madison, CT 06443

  Located in the heart of Madison, this one-bedroom/one bath unit offers relaxation on the multiple large covered decks. Overlooking the Madison Town Green, enjoy the summer concerts from the comfort of your own space. Walk to the events on the Green or the town village. Bike to beaches and more. First floor living in a two-family home. Spacious dining and living area with fireplace and built-ins.

  Brenda Davenport Pearce Real Estate

  21 Copse Rd, Madison, CT 06443
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  $455,000 Sold Sep 12, 2025

  • 1,280 Sq Ft
  • $355/SF
  • 128 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1984

  123 Legend Hill Rd Unit 123, Madison, CT 06443

  Welcome to Legend Hill, where the sunsets from this 2-bedroom 2.5 bath condominium are unsurpassed! You will be in the town of Madison with its private beaches, quaint boutiques, and summer farmers markets on the town green. What a great place to call home! This recently renovated condo has crown molding, engineered hardwood floors, and a gas fireplace, adding warmth and ambiance on those chilly

  Scott Penna William Raveis Real Estate

  123 Legend Hill Rd Unit 123, Madison, CT 06443
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  Est $130,452 Not Listed For Sale

  12 Hathaway Ln, Madison, CT 06443

  12 Hathaway Ln, Madison, CT 06443
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  /28

  $325,000

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  17 Eagle Meadow Rd, Madison, CT 06443

  Located in Eagle Meadow neighborhood, this 2 bedroom 2 bathroom home is full of potential. Currently sits as two single bedroom apartments above a 3 bay garage on 1.93 acres in a wonderful neighborhood. Ideal for an investor anyone needing workshop space, or someone looking to create their dream home in cul de sac neighborhood just north of the Madison circle. Can be sold individually or with MLS

  

  Rob McConville

  William Pitt Sotheby's Int'l

  (203) 779-6248

  17 Eagle Meadow Rd, Madison, CT 06443
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  /24

  $1,975 per month

  • 1 Bed
  • 1 Bath
  • 792 Sq Ft
  • Townhouse for Rent

  65 Old Route 79 Unit 13, Madison, CT 06443

  Great location close to town, train, shopping and beaches. Large kitchen with lots of cabinetry and counter space with a convenient eat-in area too! The bedroom is large and bright with a walk-in closet plus an additional closet. The unit comes with a stackable washer/dryer. The pull down stairs attic has some additional storage space. Central air and radiant heat. This small complex offers

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  65 Old Route 79 Unit 13, Madison, CT 06443
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  $1,425,000 Sold Sep 12, 2025

  • 4,232 Sq Ft
  • $337/SF
  • 94 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 2024

  45 Kaiser Ln, Madison, CT 06443

  Stunning to-be-built home in Madison located at the end of a lovely cul-de-sac in the sought after Century Oak community! Have it all with this new construction situated on a beautiful and peaceful lot that borders open space and is only 5 minutes to the heart of downtown Madison, including beaches, shopping, and the train station. Gorgeous kitchen with breakfast bar leads into living room with

  Karen Rosenthal William Raveis Real Estate

  45 Kaiser Ln, Madison, CT 06443
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  Est $1,371,774 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,232 Sq Ft

  10 Matthew Ct, Madison, CT 06443

  10 Matthew Ct, Madison, CT 06443
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  /35

  $799,000

  • 5 Beds
  • 3.5 Baths
  • 2,564 Sq Ft

  23 Forest Hills Dr, Madison, CT 06443

  Welcome to this classic 5-bedroom Colonial on highly sought-after Forest Hills Drive. This beautifully maintained home offers 5 spacious bedrooms and 3.5 baths, including a finished walkout lower level with a game room, guest bedroom, and full bath-perfect for entertaining or hosting overnight guests. The heart of the home is a newly renovated kitchen featuring quartz countertops, stainless steel

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 271-1979

  23 Forest Hills Dr, Madison, CT 06443
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  /13

  $2,000 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  831 Boston Post Rd, Madison, CT 06443

  Renovated 1-Bedroom Apartment Steps from Downtown. Enjoy the convenience of downtown living in this beautifully updated first-floor apartment, just a short stroll from local shops and restaurants. The gourmet kitchen features new appliances, custom cabinetry, a center island, and a spacious pantry. Perfect for cooking and entertaining. An additional room off the kitchen offers ideal space for a

  Erin Connelly Coldwell Banker Realty

  831 Boston Post Rd, Madison, CT 06443
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  $182,000 Sold Sep 08, 2025

  • 480 Sq Ft
  • $379/SF
  • 26 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1961

  48 East St, Madison, CT 06443

  Situated in the Coastal Charm of Madison, this Seasonal Cottage is your Escape you can plan on Every Summer !! Enjoy all that Madison has to offer w/ Concert's on the Green, Farmers Markets, Restaurants and Beaches. It's a Long Summer too ~ Residence can stay from April 1st all the way through October 31st., a Full 7-Months. Home is perfectly set at the End of East Street (minimal traffic) on an

  Tom Clancy William Pitt Sotheby's Int'l

  48 East St, Madison, CT 06443
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  Est $3,209,487 Not Listed For Sale

  • 5 Beds
  • 9 Baths
  • 6,598 Sq Ft

  61 Lantern Hill, Madison, CT 06443

  61 Lantern Hill, Madison, CT 06443
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  /27

  $165,000

  • 2 Beds
  • 1 Bath
  • 630 Sq Ft

  33 North St, Madison, CT 06443

  Charming Seasonal Cottage in Madison, CT - Steps from the Beach! Welcome to your perfect summer getaway! This cozy and comfortable seasonal cottage offers 629 square feet of well-utilized living space in a family and pet-friendly community, just a short stroll from Hammonasset Beach, a scenic salt pond, and the Hammonasset River. Tucked away in one of Madison's most desirable cottage villages,

  

  Joe Rodorigo

  Keystone Realty, LLC

  (203) 872-6960

  33 North St, Madison, CT 06443
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  /16

  $2,350 per month

  • 1 Bed
  • 1 Bath
  • 756 Sq Ft
  • Apartment for Rent

  36 Tuxis Rd, Madison, CT 06443

  This absolutely darling academic rental is unexpectedly available as Tenant had a change in plans. Fully furnished 1 bedroom 1 bath carriage house apartment available for rent SEPTEMBER 2025 - JUNE 2026. This 2nd floor unit overlooks a beautifully manicured backyard and features a private entrance and ample off street parking. Enjoy the walk to beach and downtown as this rental is prime location

  Phoebe Finch William Pitt Sotheby's Int'l

  36 Tuxis Rd, Madison, CT 06443
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  $475,000 Sold Sep 05, 2025

  • 2,640 Sq Ft
  • $180/SF
  • 72 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1968

  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

  108 Sandlewood Dr, Madison, CT 06443
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  Est $479,577 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,055 Sq Ft

  31 Samantha Ln, Madison, CT 06443

  31 Samantha Ln, Madison, CT 06443
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  /29

  $515,000

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

  40 Legend Hill Rd, Madison, CT 06443

  Carefree Living in Madison's Premier Legend Hill Community Set on over 80 acres of beautifully landscaped grounds, Legend Hill offers resort-style amenities including a historic clubhouse, inground pool, and tennis/pickleball courts-all just minutes from Madison's charming town center and sandy beaches. This meticulously maintained ranch style 2-bedroom unit has a lovely kitchen which opens to

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 779-6103

  40 Legend Hill Rd, Madison, CT 06443
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  /27

  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 1,374 Sq Ft
  • House for Rent

  101 Legend Hill Rd Unit 101, Madison, CT 06443

  A unique opportunity at Legend Hill. A beautifully updated one-level ranch unit on a quiet corner lot. Single-level living at its finest: an open, pretty kitchen flows into the dining room, leading to a spacious living room with a vaulted ceiling and gas fireplace. Step from the living room onto the cozy screened porch overlooking tranquil woodlands. The primary suite is bright and spacious with

  Dana Garitta William Pitt Sotheby's Int'l

  101 Legend Hill Rd Unit 101, Madison, CT 06443
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  $475,000 Sold Sep 03, 2025

  • 1,200 Sq Ft
  • $396/SF
  • 27 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1962

  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
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  Est $442,487 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,108 Sq Ft

  12 Samantha Ln, Madison, CT 06443

  12 Samantha Ln, Madison, CT 06443
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  /15

  $173,500

  • Land
  • 1.55 Acres
  • $111,935 per Acre

  728 Durham Rd, Madison, CT 06443

  Imagine building your dream home on this picturesque 1.55-acre lot in Madison, Connecticut, offering seasonal views of the serene Hog Pond. Throughout the year, enjoy the changing scenery and abundant wildlife, with opportunities for ice skating and hockey on the pond during winter months. The property includes a recent survey with topographical details and a septic design, pending only perc

  

  Gene Pica

  RE/MAX Alliance

  (475) 290-6060

  728 Durham Rd, Madison, CT 06443
• 

  

  /22

  $3,300 per month

  • 3 Beds
  • 1.5 Baths
  • 1,322 Sq Ft
  • House for Rent

  60 Bassett Ln, Madison, CT 06443

  Rent this charming home and enjoy the water views and beach access! This well cared for Cape Cod style home with fabulous location at end of dead end road offers privacy, yet the convenience of being in a private beach association and local amenities. Preferred Lease term Oct 1, 2025 thru June 1, 2026. With over 1300 sq feet of living space the light filled main level boasts gorgeous hardwood

  Jennifer Albanesi Berkshire Hathaway NE Prop.

  60 Bassett Ln, Madison, CT 06443
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  $1,610,000 Sold Sep 03, 2025

  • 4,762 Sq Ft
  • $338/SF
  • 5 Days On Market

  • 4 Beds
  • 7 Baths
  • Built 2008

  299 Warpas Rd, Madison, CT 06443

  Nestled on a private 3.3-acre estate, this meticulously maintained residence offers unparalleled luxury and comfort. Originally constructed in 2008 and completed in 2009, this 4-bedroom, 5-bathroom home has been thoughtfully updated to meet the highest standards. The spacious bedrooms each feature en-suite bathrooms, providing ultimate privacy and convenience. The fully finished lower level

  Cathy Lynch Coldwell Banker Realty

  299 Warpas Rd, Madison, CT 06443
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  Est $412,181 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  4 Stephanie Ct, Madison, CT 06443

  4 Stephanie Ct, Madison, CT 06443

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