Madison, CT Homes

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  $739,000

  $10K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft

  20 Forest Hills Dr, Madison, CT 06443

  Picture-perfect English Cape built in 1935, brimming with timeless charm and classic architectural details. A welcoming center-hall foyer features graceful archways leading to the formal living room, where custom built-ins frame the fireplace, and the elegant dining room with its original corner cabinet. It offers a sun-filled kitchen and a family room that opens to a rear deck overlooking a

  

  Dana Weinstein

  Coldwell Banker Realty

  20 Forest Hills Dr, Madison, CT 06443
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  /10

  $3,600 Per Month

  • 2 Beds
  • 1 Bath
  • 1,386 Sq Ft
  • Apartment for Rent

  82 Wall St Unit 200, Madison, CT 06443

  Spacious, fully furnished 2nd floor apartment located in the heart of downtown Madison. Light and bright loft like open concept floor plan with granite countertops, stainless appliances, central air and in-unit laundry. Halfway between New York and Boston, minutes from fine dining, specialty shops, town beaches, library, train and I95.

  

  Cathy Lynch

  Coldwell Banker Realty

  82 Wall St Unit 200, Madison, CT 06443
• 

  $725,000

  Sold Dec 22, 2025

  318 Horse Pond Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,622 Sq Ft
  • Built 1994

  Last Sold Summary

  • $277/SF
  • 40 Days On Market

  Current Estimated Value $774,201

  Last Listing Agent Carol Farmer William Raveis Real Estate

  318 Horse Pond Rd, Madison, CT 06443
• 

  Est $1,391,388

  Not Listed For Sale

  188 Bartlett Dr, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 5,527 Sq Ft
  • Built 1991

  188 Bartlett Dr, Madison, CT 06443

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent James Montanaro Coldwell Banker Realty
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  $1,695,000

  • 5 Beds
  • 3.5 Baths
  • 3,912 Sq Ft

  30 Meeting House Ln, Madison, CT 06443

  Historic gem on the Madison Village Green. Once known as "Hartsbourne," this storied Madison residence is celebrated for its premier location overlooking the town green and its timeless architectural presence. A true local landmark, the home is distinguished by its striking curved eaved roofline, reminiscent of a pagoda with a unique flat seamed copper roof center. Beautifully aligned with the

  

  Cathy Lynch

  Coldwell Banker Realty

  30 Meeting House Ln, Madison, CT 06443
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  /17

  $3,400

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,571 Sq Ft
  • House for Rent

  31 Highland Terrace, Madison, CT 06443

  Available for yearly or academic lease. Can also be partially furnished. Enjoy coastal living in this charming year-round rental just a short walk to private Fountain Beach in Madison. Rent also includes a spot to store a kayak, paddle board or row boat at the private beach. This 2-bedroom, newly refreshed 1-bath home features an inviting open floor plan with beautiful newly refinished hardwood

  31 Highland Terrace, Madison, CT 06443
• 

  $650,000

  Sold Apr 24, 2026

  743 Green Hill Rd, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 2,523 Sq Ft
  • Built 1979

  Last Sold Summary

  • 3% Below List Price
  • $258/SF
  • 25 Days On Market

  Current Estimated Value $670,041

  Last Listing Agent Stacy Anselmo Coldwell Banker Realty

  743 Green Hill Rd, Madison, CT 06443
• 

  Est $897,835

  Not Listed For Sale

  31 Pine Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,804 Sq Ft
  • Built 1976

  31 Pine Dr, Madison, CT 06443

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Todd Gould William Pitt Sotheby's Int'l
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  $1,300,000

  • 5 Beds
  • 3.5 Baths
  • 4,783 Sq Ft

  77 Silo Hill, Madison, CT 06443

  Welcome to this fabulous one-owner custom home in sought-after Neck River Farms. A gracious, spacious foyer warmly welcomes you inside, setting the tone for the beautifully maintained interior filled with abundant natural light. A dedicated home office with elegant French doors offers the perfect space for working remotely or quiet study. The inviting living room is ideal for entertaining,

  

  Cathy Lynch

  Coldwell Banker Realty

  77 Silo Hill, Madison, CT 06443
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  $3,300 Per Month

  • 4 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
• 

  $1,875,000

  Sold Jun 29, 2026

  31 Stony Lane Lot 3 Rd, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 4,565 Sq Ft
  • Built 2024

  Last Sold Summary

  • 25% Below List Price
  • $411/SF
  • 336 Days On Market

  Last Listing Agent Lindsay Greenberg William Raveis Real Estate

  31 Stony Lane Lot 3 Rd, Madison, CT 06443
• 

  Est $719,174

  Not Listed For Sale

  118 Flintlock Rd, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 1967

  118 Flintlock Rd, Madison, CT 06443

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Faith Whitehead William Pitt Sotheby's Int'l
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  $1,378,800

  • 3 Beds
  • 2.5 Baths
  • 2,767 Sq Ft

  1308 Durham Rd, Madison, CT 06443

  Originally built in 1825, this residence has been thoughtfully updated to preserve its historic essence while incorporating modern conveniences. Nestled on a generous 4.38-acre lot, this extraordinary home boasts 3 spacious bedrooms and 2.5 beautifully appointed bathrooms within its expansive 3,500 square feet of living space. As you step inside, you'll be captivated by the elegant oak hardwood

  

  Nick Prevost

  William Raveis Real Estate

  1308 Durham Rd, Madison, CT 06443
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  $3,500 Plus Fees

  • 3 Beds
  • 1.5 Baths
  • 1,008 Sq Ft
  • House for Rent

  24 Hamilton Dr, Madison, CT 06443

  Welcome to your new home in the heart of Madison Center, CT! This charming property offers a convenient location, just minutes away from an array of exceptional restaurants and a nearby department store. Enjoy the serene beauty of East Wharf Beach Park, all within walking distance.Key features of this property include a spacious layout with ample light. The comfort of central heating and

  24 Hamilton Dr, Madison, CT 06443
• 

  $1,927,500

  Sold Aug 19, 2025

  44 E Wharf Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,700 Sq Ft
  • Built 1924

  Last Sold Summary

  • 2% Above List Price
  • $714/SF
  • 8 Days On Market

  Current Estimated Value $1,895,406

  Last Listing Agent Margaret Muir William Pitt Sotheby's Int'l

  44 E Wharf Rd, Madison, CT 06443
• 

  Est $673,025

  Not Listed For Sale

  94 Boston Post Rd, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 1,668 Sq Ft
  • Built 1976

  94 Boston Post Rd, Madison, CT 06443

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Camille Ackermann Berkshire Hathaway NE Prop.
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  /40

  $675,000

  • 4 Beds
  • 2.5 Baths
  • 2,536 Sq Ft

  320 Summer Hill Rd, Madison, CT 06443

  Take a 3D Tour or Enjoy a Video Walkthrough 24/7! Set on 1.1 acres, this 2,536 SF Contemporary offers 4 BR, 2.5 Baths & a great opportunity for Buyers ready to make HGTV-inspired updates while building equity in Madison. Built in 1976, the home features a dramatic contemporary layout, multiple fireplaces, a large Living Room, a Family Room with a brick fireplace & sliders to a bright 3-Season

  

  Gregory Hanner

  Garden Realty

  320 Summer Hill Rd, Madison, CT 06443
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  /18

  $3,000 Per Month

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

  37 Beach Ave, Madison, CT 06443

  37 Beach Avenue is ready to welcome its next resident! Simply cute as a button, perfectly positioned off Neck Road and just a short stroll to the shore - complete with beach rights - this is the coastal retreat you've been waiting for! One look and you'll surely feel right at home. Featuring two bedrooms, one full bathroom, on-site, main-level laundry, and a wonderfully sized yard, this adorable

  Melanie Abbott William Pitt Sotheby's Int'l

  37 Beach Ave, Madison, CT 06443
• 

  $780,000

  Sold Apr 17, 2026

  76 Bartlett Dr, Madison, CT 06443

  • 5 Beds
  • 2.5 Baths
  • 3,100 Sq Ft
  • Built 1976

  Last Sold Summary

  • 1% Above List Price
  • $252/SF
  • 23 Days On Market

  Current Estimated Value $773,208

  Last Listing Agent Lisa Liscio Century 21 AllPoints Realty

  76 Bartlett Dr, Madison, CT 06443
• 

  Est $537,232

  Not Listed For Sale

  11 Strathmore Ln, Madison, CT 06443

  • 2 Beds
  • 3 Baths
  • 1,680 Sq Ft
  • Built 1977

  11 Strathmore Ln, Madison, CT 06443

  Last Sold Summary

  • 95 Days On Market

  Last Listing Agent Pam Kadamus William Pitt Sotheby's Int'l
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  /40

  $899,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,253 Sq Ft

  61 Bishop Ln, Madison, CT 06443

  Absolutely charming Cape Cod-style home set on 1.87 private acres, just minutes from downtown Madison. This builder's own residence has been thoughtfully rebuilt from top to bottom in recent years with major updates including the roof, siding, AZEK trim, windows, interior doors, electrical, plumbing, recessed lighting, foam insulation and HVAC, offering peace of mind and modern efficiency. The

  

  Dana Weinstein

  Coldwell Banker Realty

  61 Bishop Ln, Madison, CT 06443
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  $6,000

  Total Monthly Price

  • 4 Beds
  • 3 Baths
  • House for Rent

  187 Wildcat Rd, Madison, CT 06443

  AVAILABLE EARLY SEPTEMBER TO THE END OF MAY, 2027. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse,

  187 Wildcat Rd, Madison, CT 06443
• 

  $575,000

  Sold Jun 16, 2026

  526 Horse Pond Rd, Madison, CT 06443

  • 3 Beds
  • 1.5 Baths
  • 1,544 Sq Ft
  • Built 1986

  Last Sold Summary

  • $372/SF
  • 18 Days On Market

  Current Estimated Value $575,308

  Last Listing Agent Cathy Lynch Coldwell Banker Realty

  526 Horse Pond Rd, Madison, CT 06443
• 

  Est $1,343,929

  Not Listed For Sale

  108 Neck Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,610 Sq Ft
  • Built 1830

  108 Neck Rd, Madison, CT 06443

  Last Sold Summary

  • 284 Days On Market

  Last Listing Agent Margaret Muir William Pitt Sotheby's Int'l
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  /40

  $899,900

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,807 Sq Ft

  9 Randi Dr, Madison, CT 06443

  Nestled on sought-after Randi Drive, this beautifully maintained Colonial offers spacious living in a prime Madison location. The home features a formal living room and dining room, a large kitchen with a sunny breakfast area, and an oversized family room with a fireplace and wood-burning stove. Upstairs you'll find 4 bedrooms, including 2 beautifully remodeled bathrooms. A finished third floor

  

  Cathy Lynch

  Coldwell Banker Realty

  9 Randi Dr, Madison, CT 06443
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  /28

  $11,000 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,418 Sq Ft
  • House for Rent

  122 Taylor Ave, Madison, CT 06443

  AVAILABLE FOR MONTH OF AUGUST. Relax and unwind for a summer at the beach. This well maintained, 3 bedroom home with vintage beach house charm, has easy access to a private association sandy beach just steps away. The open Living Room and Dining Room with the original wood floors are adjacent to a well equipped and modestly updated kitchen for all of your food preparation needs. There is also a

  Kirsten Adams William Pitt Sotheby's Int'l

  122 Taylor Ave, Madison, CT 06443
• 

  $1,045,000

  Sold Sep 26, 2025

  39 Madison Ave, Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 1,891 Sq Ft
  • Built 1957

  Last Sold Summary

  • 10% Above List Price
  • $553/SF
  • 13 Days On Market

  Current Estimated Value $1,194,215

  Last Listing Agent Phoebe Schreiner William Pitt Sotheby's Int'l

  39 Madison Ave, Madison, CT 06443
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  Not Listed For Sale

  00 Stone Rd, Madison, CT 06443

  00 Stone Rd, Madison, CT 06443

  Last Sold Summary

  • 156 Days On Market

  Last Listing Agent Betsy Anderson William Pitt Sotheby's Int'l
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  /40

  $749,000

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  7 Milestone Ln, Madison, CT 06443

  Nestled on a beautifully elevated homesite, this classic Colonial offers the perfect blend of privacy, comfort, and New England charm. Set in a desirable neighborhood just minutes from charming Madison Village, the Town Green, shops, restaurants, and the stunning Connecticut shoreline, this home offers the perfect blend of location and lifestyle. This spacious 4-bedroom home features a welcoming

  

  Cathy Lynch

  Coldwell Banker Realty

  7 Milestone Ln, Madison, CT 06443
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  /32

  $4,500

  Total Monthly Price

  • 4 Beds
  • 3 Baths
  • House for Rent

  82 Scotland Rd, Madison, CT 06443

  This meticulously cared for ranch offers the ideal blend of comfort, style, and convenience-all just moments from town. Set on a stunning private property, the home's setting, condition, and location make it a rare rental opportunity. Step inside to a one level layout filled with charm and thoughtful updates. The newly refreshed kitchen features brand-new appliances, updated countertops and

  82 Scotland Rd, Madison, CT 06443
• 

  $590,000

  Sold Sep 29, 2025

  7 Downing Way, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 1,853 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $318/SF
  • 24 Days On Market

  Current Estimated Value $597,437

  Last Listing Agent Margaret Muir William Pitt Sotheby's Int'l

  7 Downing Way, Madison, CT 06443
• 

  Est $848,178

  Not Listed For Sale

  875 Boston Post Rd Unit 3, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 1,513 Sq Ft
  • Built 1900

  875 Boston Post Rd Unit 3, Madison, CT 06443

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Cathy Lynch Coldwell Banker Realty
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  /32

  $569,000

  Under Contract

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

  40 Hampshire Rd Unit 40, Madison, CT 06443

  Beautifully maintained 2-bedroom condominium in desirable Kensington North, just minutes from Madison's charming town center and beautiful beaches. The bright, inviting kitchen opens to the living and dining areas, where a gas fireplace creates a warm and welcoming atmosphere. A delightful sunroom overlooks the private patio and beautifully landscaped garden, offering a peaceful retreat for

  

  Cathy Lynch

  Coldwell Banker Realty

  40 Hampshire Rd Unit 40, Madison, CT 06443
• 

  

  /5

  $4,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 1,925 Sq Ft
  • House for Rent

  125 Island Ave, Madison, CT 06443

  Spend your winter is this absolutely charming a pristine home just steps from the beach. The open floor plan allows room for everyone, the spacious bedrooms allows for comfortable guests. Come see this charming home.

  Meig Walz Newcomb Coldwell Banker Realty

  125 Island Ave, Madison, CT 06443
• 

  $630,000

  Sold Feb 19, 2026

  300 Mungertown Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,224 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $283/SF
  • 10 Days On Market

  Current Estimated Value $643,604

  Last Listing Agent Tom Clancy William Pitt Sotheby's Int'l

  300 Mungertown Rd, Madison, CT 06443
• 

  Est $201,049

  Not Listed For Sale

  2117 Durham Rd, Madison, CT 06443

  2117 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 101 Days On Market

  Last Listing Agent Lisa Toczko Home Valley Realty, LLC
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  /37

  $1,395,000

  Pending

  • 2 Beds
  • 3 Baths
  • 2,378 Sq Ft

  33 Madison Ave, Madison, CT 06443

  Built in 1998, this distinctive shingle-style contemporary is ideally located within walking distance of East Wharf Beach, downtown Madison, and its charming shops and restaurants. Exceptional stonework, lush gardens, and a tranquil pond create a private outdoor oasis that you enjoy as you enter from Pheasant Drive. The main level features a beautifully appointed kitchen with mahogany

  

  Dana Weinstein

  Coldwell Banker Realty

  33 Madison Ave, Madison, CT 06443
• 

  

  /18

  $3,750

  Total Monthly Price

  • 4 Beds
  • 2 Baths
  • 2,192 Sq Ft
  • House for Rent

  1281 Durham Rd, Madison, CT 06443

  For Rent or PurchaseCharming Large Madison Mother/Daughter Home!This delightful 4-bedroom Home features a large modern chef's kitchen, a cozy living room with a fireplace, 2 bedrooms on the first floor, a spacious bathroom, laundry area, and a bonus room that adds extra width to the house.Upstairs, you'll find a brand-new large living room, kitchen, bathroom, and 2

  1281 Durham Rd, Madison, CT 06443
• 

  $730,000

  Sold Dec 23, 2025

  677 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • Built 2022

  Last Sold Summary

  • 9% Below List Price
  • $346/SF
  • 145 Days On Market

  Current Estimated Value $765,776

  Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty

  677 Durham Rd, Madison, CT 06443
• 

  Est $719,904

  Not Listed For Sale

  67 Boston Post Rd Unit 7, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 2,252 Sq Ft
  • Built 2016

  67 Boston Post Rd Unit 7, Madison, CT 06443

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Kathleen Moniello Coldwell Banker Realty

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