Madison, CT Homes

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  /40

  $3,000,000

  • 6 Beds
  • 4.5 Baths
  • 6,300 Sq Ft

  37 Lantern Hill Rd, Madison, CT 06443

  Welcome to 37 Lantern Hill Road, a luxurious residence nestled in the heart of Madison's most coveted neighborhood. Just a short stroll from pristine beaches, the charming town center, and the Madison Country Club, this home offers an unparalleled lifestyle of comfort and convenience. Tucked away along picturesque brick-lined sidewalks and illuminated by classic lanterns, this exceptional

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 283-9847

  37 Lantern Hill Rd, Madison, CT 06443
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  /35

  $5,250 per month

  • 4 Beds
  • 3 Baths
  • 2,065 Sq Ft
  • House for Rent

  33 Grove Ave, Madison, CT 06443

  FULLY FURNISHED - $5,250/TWO WEEKS. Dates available 7/14-7/28 and 8/13-8/31. Will not consider less than two week rental. Four bedroom colonial just steps from Seaview Beach, a private association beach! Fully furnished, internet is available, TV in 3 rooms. Hardwood floors throughout. Sunroom at back of house, along with a wraparound porch with views of Long Island Sound. Kayak in the photos is

  Robert Curry Pearce Real Estate

  33 Grove Ave, Madison, CT 06443
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  $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
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  Est $457,729 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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  /40

  $625,000

  • 3 Beds
  • 3,768 Sq Ft

  36 Jannas Ln, Madison, CT 06443

  Hey there! Check out this stunning contemporary house located just a few houses north of Rt 1. It's sitting on a knoll and has so much potential, but it does need a complete remodeling. This is your chance to redesign the interior and make it your own! The location is perfect - close to town, the Long Island Sound, and even a golf course. This could be your ideal summer retreat or a cozy

  

  Harry Finer

  William Raveis Real Estate

  (203) 580-6329

  36 Jannas Ln, Madison, CT 06443
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  /12

  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 1,538 Sq Ft
  • House for Rent

  32 E Wharf Rd, Madison, CT 06443

  Available from September to May. Step inside to find a light-filled living area with classic colonial touches and a functional layout ideal for everyday living. The kitchen opens to a cozy dining area, perfect for meals at home or entertaining guests. Upstairs, you'll find two generously sized bedrooms with ample closet space and a full bath. Enjoy the convenience and the serenity of a private

  Meig Walz Newcomb Coldwell Banker Realty

  32 E Wharf Rd, 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
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  Est $434,324 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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  /39

  $1,450,000 Pending

  • 4 Beds
  • 7 Baths
  • 4,762 Sq Ft

  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

  (203) 718-0870

  299 Warpas Rd, Madison, CT 06443
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  /25

  $6,000 per month

  • 5 Beds
  • 3 Baths
  • 2,456 Sq Ft
  • House for Rent

  156 Kelsey Place, Madison, CT 06443

  SEPT '25 - MAY '26 ACADEMIC WATERFRONT RENT available now to see. Plan ahead. With amazing views out over Long Island Sound & beyond this light & bright Beach Colonial was built in 2006 plus has a recent 3 BR addition! Featuring an open floor plan, all in excellent condition with lots of glass & a wrap around deck to take full advantage of it's setting. Located at the very end of a private street

  Todd Gould William Pitt Sotheby's Int'l

  156 Kelsey Place, Madison, CT 06443
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  $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
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  Est $393,432 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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  /40

  $799,900 Pending

  • 4 Beds
  • 3 Baths
  • 2,896 Sq Ft

  15 Saxon Rd, Madison, CT 06443

  Sun-Filled Colonial in Prime Madison Location. Ideally situated near Madison's beautiful beaches and vibrant town center, this well-maintained and thoughtfully updated 4-bedroom, 3-bath Colonial offers both comfort and convenience. A spacious family room addition features vaulted ceilings, custom built-ins, and a cozy wood-burning fireplace-perfect for relaxing or entertaining. Upstairs, you'll

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 253-3003

  15 Saxon Rd, Madison, CT 06443
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  /11

  $2,600 per month

  • 2 Beds
  • 1.5 Baths
  • 1,224 Sq Ft
  • House for Rent

  33 Copse Rd Unit B, Madison, CT 06443

  Available September to June, this in-town carriage house will make you feel right at home with its abundance of charm, comfortable furnishings and bright open floor plan. First floor bedroom and full bath. Eat in kitchen with granite counters and stainless appliances also offers a combination washer/dryer. Sun drenched living room with vaulted ceiling makes cottage space very special. A second

  Julie Ovian William Pitt Sotheby's Int'l

  33 Copse Rd Unit B, Madison, CT 06443
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  $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
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  Est $529,989 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,281 Sq Ft

  20 Jasper Ln, Madison, CT 06443

  20 Jasper Ln, Madison, CT 06443
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  /16

  $379,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,116 Sq Ft

  339 Horse Pond Rd, Madison, CT 06443

  Charming 1933 Cape Cod located in Madison, one of Connecticut's most desirable shoreline towns! This vintage 3-bedroom Cape is full of charm and potential. Just minutes from Madison's beautiful town beaches, Hammonasset Beach State Park, and a vibrant, walkable downtown filled with cafes, boutiques, an award-winning bookstore, a cinema, and more. The flexible layout features a cozy living room

  Linda Lang-Bankowski The Real Estate Boutique, LLC

  339 Horse Pond Rd, Madison, CT 06443
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  /20

  $3,000 per month

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

  36 Whedon Ln, Madison, CT 06443

  Location! 5 minutes from the beautiful Surf Club Beach and the quaint village of Madison. Academic rental Sept.1- May 31. This updated cottage sits at the end of a peaceful private road south of Boston Post Rd. One floor living, with eat-in kitchen, quartz counters, large island, stainless appliances. Washer/dryer. King and Queen bedrooms feature ceiling fans. Ductless AC/heat pump throughout.

  Jorge Zea Blue Lighthouse Realty, Inc

  36 Whedon Ln, Madison, CT 06443
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  $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
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  Est $461,191 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,177 Sq Ft

  17 Jasper Ln, Madison, CT 06443

  17 Jasper Ln, Madison, CT 06443
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  /39

  $995,000

  • 3 Beds
  • 3 Baths
  • 2,728 Sq Ft

  109 Boston Post Rd, Madison, CT 06443

  Built in 1865 for John Newton Chittenden, this historic home is sited on a professionally landscaped one-acre flat lot. Blending the best elements of classic charm and new upgrades, this house has it all! On the main level, you'll find a formal living room with hardwood floors, a wood-burning fireplace, and built-in bookshelves. The dining room is truly spacious with vaulted ceilings, another

  Jack Hill Seabury Hill REALTORS

  109 Boston Post Rd, Madison, CT 06443
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  /30

  $8,000 per month

  • 7 Beds
  • 7 Baths
  • 5,075 Sq Ft
  • House for Rent

  118 Middle Beach Rd, Madison, CT 06443

  ACADEMIC RENTAL! The iconic, water-front 118 Middle Beach Road is available for rent for the academic year beginning October 1, 2025. This sensational property offers comfortable occupancy for up to fourteen people with 7 bedrooms, 5 full baths, and 2 half baths. The main level is an entertainer's dream featuring an oversized, eat-in kitchen, formal dining area, living room with water views from

  Melanie Abbott William Pitt Sotheby's Int'l

  118 Middle Beach Rd, Madison, CT 06443
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  $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
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  Est $466,044 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,336 Sq Ft

  2313 Durham Rd, Madison, CT 06443

  2313 Durham Rd, Madison, CT 06443
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  /26

  $850,000 Open Sat 12:30PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,116 Sq Ft

  57 Circle Beach Rd, Madison, CT 06443

  Nestled along the shores of Long Island Sound, this classic 3-bedroom, 1.5-bath, this 1116 sq.ft cottage offers a rare opportunity to own a true waterfront retreat with panoramic views-including Faulkner's Island-and a separate deep water dock on the Neck River just across the street. From the moment you step inside, you're welcomed by sweeping, unobstructed water views and endless potential.

  Cheryl Kebalo ENRG Global Realty, LLC

  57 Circle Beach Rd, Madison, CT 06443
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  /39

  $3,300 per month

  • 4 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • House for Rent

  32 Bassett Ln, Madison, CT 06443

  AVAILABLE FROM SEPTEMBER 8, 2025 TO JUNE 15, 2026! Welcome to this enchanting 4 bedroom, 2 full bath home, where the beach is just a half-block stroll away! Located off Neck Road, 1 mile from the heart of Madison, CT, this residence offers the perfect blend of coastal charm and convenience. As you enter, the first floor greets you with a Family Room, through to a Kitchen, then onto the Living

  Kirsten Adams William Pitt Sotheby's Int'l

  32 Bassett Ln, Madison, CT 06443
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  $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
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  Est $1,283,762 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,865 Sq Ft

  217 Devonshire Ln, Madison, CT 06443

  217 Devonshire Ln, Madison, CT 06443
• 

  

  /40

  $1,098,000

  • 5 Beds
  • 3 Baths
  • 2,781 Sq Ft

  8 Highview Rd, Madison, CT 06443

  One-of-a-kind home in a small, sought-after subdivision close to the heart of charming Madison, CT. This architecturally distinctive residence features soaring cathedral ceilings and skylights in the living room, vaulted ceilings in the dining room, and a striking shiplap ceiling in the expansive family room. Two wood-burning fireplaces create cozy focal points in both living and family rooms.

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  8 Highview Rd, Madison, CT 06443
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  /29

  $3,100 per month

  • 3 Beds
  • 2 Baths
  • 1,529 Sq Ft
  • House for Rent

  27 Ridgewood Ave, Madison, CT 06443

  SEEKING A 3 BEDROOM FULLY FURNISHED ACADEMIC RENTAL IN A MADISON BEACH COMMUNITY? This lovely home, located in the Neck Road area of Madison, with beach rights, is filled with old world charm but with modern conveniences - large Living Room is the entire front of the home, over looking a screened in porch. There is a dedicated Dining Room, 1st floor Den (office) with pull out couch and access to

  Kirsten Adams William Pitt Sotheby's Int'l

  27 Ridgewood Ave, Madison, CT 06443
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  $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
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  Est $785,160 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,040 Sq Ft

  37 Blueberry Hill Dr, Madison, CT 06443

  37 Blueberry Hill Dr, Madison, CT 06443
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  /40

  $1,495,000

  • 5 Beds
  • 3.5 Baths
  • 2,647 Sq Ft

  20 Cherry Ln, Madison, CT 06443

  The best of all worlds awaits in this year-round 5-bedroom, 3-bath home located on a private, quiet road across from the third hole of the Madison Country Club. Walk downtown or stroll to the beach to enjoy sandy shores and breathtaking sunsets. Perfect for entertaining, the layout features a bright living room that opens to the dining area. The galley-style kitchen, thoughtfully designed by

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  20 Cherry Ln, Madison, CT 06443
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  /38

  $6,500 per month

  • 4 Beds
  • 2.5 Baths
  • 3,127 Sq Ft
  • House for Rent

  144 Middle Beach Rd, Madison, CT 06443

  Your beach sanctuary awaits!!! This direct waterfront beauty will be available as an academic year rental from Labor Day through Memorial Day. Enjoy your own private sandy beach at low tide. With 4 bedrooms and 2.5 baths, you'll have plenty of space for friends and family. Upon entry, you are welcomed by an open floor plan, with a tastefully remodeled kitchen, living room and dining room combo,

  Agota Perry-Hill William Raveis Real Estate

  144 Middle Beach Rd, Madison, CT 06443
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  $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
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  Est $812,773 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,392 Sq Ft

  211 Devonshire Ln, Madison, CT 06443

  211 Devonshire Ln, Madison, CT 06443
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  /40

  $1,050,000

  • 3 Beds
  • 2.5 Baths
  • 2,558 Sq Ft

  659 Summer Hill Rd, Madison, CT 06443

  The 1779 Curtis Dudley center chimney cape w/extensive expansion & renovation is 2558 Sf of inviting & elegant spaces. Yesterday's charm & all the conveniences of today (new roof, central air conditioning, etc.) With wide plank Chestnut floors and 3 fireplaces in the first floor Living Room, Dining Room & Keeping Room the vintage house charm is so inviting! The Keeping Room has a wall of French

  Leigh Whiteman William Raveis Real Estate

  659 Summer Hill Rd, Madison, CT 06443
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  /31

  $11,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,518 Sq Ft
  • House for Rent

  22 Fairview Ave, Madison, CT 06443

  Enjoy the month of August (would consider a week or two at a prorated price) in this charming, mint condition, furnished cape located in the very desirable Seaview beach area. Perfect retreat for a relaxing escape by the sea. Your very own beach association is just steps away. All you need is a beach chair and a good book and feel any stress you may have simply dissipate! The sunrises and sunsets

  Anne-Marie Pagli William Raveis Real Estate

  22 Fairview Ave, Madison, CT 06443
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  $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
• 

  Est $717,491 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,607 Sq Ft

  98 Dorset Ln, Madison, CT 06443

  98 Dorset Ln, Madison, CT 06443

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