Madison, CT Homes

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  /35

  $995,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 4,015 Sq Ft

  351 Bartlett Dr, Madison, CT 06443

  Beautifully sited on a fabulous private lot in the highly sought-after Neck River Farms Neighborhood, this stunning Colonial offers over 4,000 square feet of exceptional living space with 4-5 bedrooms and 3.5 baths. A welcoming foyer showcases a handsome staircase & sets the tone for the naturally light-filled interior. Entertain with ease in the banquet-sized dining room & expansive

  Susan Santoro William Pitt Sotheby's Int'l

  351 Bartlett Dr, Madison, CT 06443
• 

  

  

  /10

  $2,400 Per Month

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

  68 Kelsey Place, Madison, CT 06443

  BEACH ! Adorable beach association ranch home available for Academic rental starting first week of Sept through May. Pets considered with additional rent. Large 3 season front porch extends living space. 2 BR plus an additional fold down futon in den. Eat in kitchen. Full shower bath was totally renovated 3 years ago. Stackable washer and dryer is 3 years old. Paved driveway can accommodate 3

  Deborah Rowe William Raveis Real Estate

  68 Kelsey Place, Madison, CT 06443
• 

  $960,000

  Sold Jun 30, 2025

  218 Neck Rd, Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 2,047 Sq Ft
  • Built 1967

  Last Sold Summary

  • 4% Above List Price
  • $469/SF
  • 6 Days On Market

  Current Estimated Value $1,025,105

  Last Listing Agent Michelle Drobot Coldwell Banker Realty

  218 Neck Rd, Madison, CT 06443
• 

  Est $524,996

  Not Listed For Sale

  1928 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft
  • Built 1747

  1928 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 56 Days On Market
• 

  

  /2

  $350,000

  $100K PRICE DROP

  • Land
  • 2.05 Acres
  • $170,732 per Acre

  92 Scotland Rd Unit Lot. 3, Madison, CT 06443

  Build your dream home in the upscale shoreline community of Madison CT! Featured in Yankee Magazine as "Best Beach Towns" in Connecticut and not many land opportunities like this. Centrally located this approved lot is a very large 2.05 acre lot that is level, wooded, and private in a well established upscale neighborhood ONLY 1.2 miles from downtown and approximately 2 miles from Hammonasset

  Stacy Bucci Coldwell Banker Realty

  92 Scotland Rd Unit Lot. 3, Madison, CT 06443
• 

  

  /14

  $7,000 Per Month

  • 2 Beds
  • 1 Bath
  • 608 Sq Ft
  • Apartment for Rent

  165 Middle Beach Rd, Madison, CT 06443

  AVAILABLE FOR THE MONTH OF AUGUST. Live the ultimate shoreline lifestyle on Middle Beach Road, Madison's most prestigious and sought-after coastal street. This delightful 2-bedroom, 1-bathroom garage apartment (on the 2nd floor) offers a rare opportunity to enjoy stunning dual views, capturing the sparkling waters of the Long Island Sound from one side and the serene, ever-changing landscape of

  Kirsten Adams William Pitt Sotheby's Int'l

  165 Middle Beach Rd, Madison, CT 06443
• 

  $860,000

  Sold Mar 02, 2026

  100 Concord Dr, Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 3,517 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Above List Price
  • $245/SF
  • 40 Days On Market

  Current Estimated Value $859,149

  Last Listing Agent Amanda Popplewell-Sanson Coldwell Banker Realty

  100 Concord Dr, Madison, CT 06443
• 

  Est $581,949

  Not Listed For Sale

  1956 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 1,928 Sq Ft
  • Built 1998

  1956 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 23 Days On Market
• 

  

  /40

  $998,000

  Open Wed 4:30PM - 6:30PM

  • 3 Beds
  • 3.5 Baths
  • 3,536 Sq Ft

  10 Isabell Dr, Madison, CT 06443

  Built in 2001, this expansive Custom Cape with its charming front covered porch offers a one-of-a-kind setting in North Madison, ideally located at the end of a cul-de-sac on 2.64 acres and surrounded by open space. The square footage is deceptive with 3536 sf (this DOES NOT include the 3-season room +452 sf) plus the huge basement offering another 1880 sf. Designed with intention and exceptional

  Claudia O'Connell William Raveis Real Estate

  10 Isabell Dr, Madison, CT 06443
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  /34

  $12,000 Per Month

  • 3 Beds
  • 3 Baths
  • 2,382 Sq Ft
  • House for Rent

  509 Boston Post Rd, Madison, CT 06443

  Sneak away from the hustle and bustle and spend the month of August at Captain Eber Judd House (circa 1740). This historical gem, reminiscent of Nantucket and Essex Whaling Captain's homes, oozes charm with its stunning wide plank floors, beams, and original fireplaces. Located in the heart of downtown Madison, it's just steps from the gorgeous beach, the quintessential downtown, and the Friday

  Phoebe Schreiner William Pitt Sotheby's Int'l

  509 Boston Post Rd, Madison, CT 06443
• 

  $550,000

  Sold Nov 05, 2025

  Unlisted Address

  • 1 Bed
  • 2 Baths
  • 1,569 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Above List Price
  • $351/SF
  • 19 Days On Market

  Current Estimated Value $544,618

  Last Listing Agent Renee Salafia William Raveis Real Estate

  Unlisted Address
• 

  Est $712,815

  Not Listed For Sale

  25 Summit Ln, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,323 Sq Ft
  • Built 1996

  25 Summit Ln, Madison, CT 06443

  Last Sold Summary

  • 1 Day On Market
• 

  

  /11

  $1,450,000

  New Construction 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
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  /33

  $5,700 Per Month

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • House for Rent

  146 Chittenden Field Ln, Madison, CT 06443

  Available from September 15, 2026, through May 15, 2027, this stunning direct-waterfront academic rental offers an unparalleled coastal lifestyle with breathtaking, panoramic views from almost every room. The bright, sunny interior features an open-concept main level, highlighting a gourmet kitchen with quartz countertops and stainless steel appliances, alongside a generous living and dining area

  Sue Knapp William Pitt Sotheby's Int'l

  146 Chittenden Field Ln, Madison, CT 06443
• 

  $648,500

  Sold Aug 08, 2025

  94 Boston Post Rd, Madison, CT 06443

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

  Last Sold Summary

  • 1% Below List Price
  • $389/SF
  • 60 Days On Market

  Current Estimated Value $662,322

  Last Listing Agent Camille Ackermann Berkshire Hathaway NE Prop.

  94 Boston Post Rd, Madison, CT 06443
• 

  Est $764,575

  Not Listed For Sale

  272 County Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,614 Sq Ft
  • Built 2000

  272 County Rd, Madison, CT 06443

  Last Sold Summary

  • 2 Days On Market
• 

  

  /35

  $225,000

  $24K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 647 Sq Ft

  26 North St, Madison, CT 06443

  Experience the best of shoreline living in Madison, just about a mile from the sandy beaches of Hammonasset. This charming seasonal cottage offers a bright, airy feel with vaulted wood-beamed ceilings and natural light throughout-perfect for easy summer living by the water. With 647 square feet, the home includes two bedrooms (one ideal as a den or flex space), a sun-filled kitchen with stone

  Karen Floriano William Raveis Real Estate

  26 North St, Madison, CT 06443
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  /17

  $2,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • House for Rent

  55 Overshores W, Madison, CT 06443

  AVAILABLE THIS SEPTEMBER 1 TO JUNE 30, 2027. PARTIALLY FURNISHED. PAINTED ALL WHITE. NEWER REFINISHED HARDWOOD FLOORS! NEWER BATHROOM! This open concept 2 bedroom home, hardwood floors, and located in one of the best beach Associations off Neck Road, is perfect for 1-2 people. Fabulous deck off the back of the home provides a perfect place to enjoy a book or glass of wine. Absolutely NO pets, no

  Kirsten Adams William Pitt Sotheby's Int'l

  55 Overshores W, Madison, CT 06443
• 

  $900,000

  Sold Nov 17, 2025

  15 Buttonball Ln, Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 2,576 Sq Ft
  • Built 1969

  Last Sold Summary

  • 6% Above List Price
  • $349/SF
  • 55 Days On Market

  Current Estimated Value $887,831

  Last Listing Agent Cathy Lynch Coldwell Banker Realty

  15 Buttonball Ln, Madison, CT 06443
• 

  Est $771,501

  Not Listed For Sale

  35 Lakewood Dr, Madison, CT 06443

  • 6 Beds
  • 3.5 Baths
  • 3,146 Sq Ft
  • Built 2001

  35 Lakewood Dr, Madison, CT 06443

  Last Sold Summary

  • 80 Days On Market
• 

  

  /25

  $154,000

  • 1 Bed
  • 1 Bath
  • 476 Sq Ft

  16 North St, Madison, CT 06443

  Escape to the Connecticut shoreline with this beautifully maintained seasonal cottage in Dud's Village in Madison-the perfect summer retreat just minutes from the beach. Located less than one mile from Hammonasset Beach State Park, Connecticut's largest shoreline park, this charming getaway offers effortless access to two miles of sandy beaches, scenic walking and biking trails, and endless

  Tricia Farin Real Broker CT, LLC

  16 North St, Madison, CT 06443
• 

  

  /25

  $6,000 Per Month

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

  156 Kelsey Place, Madison, CT 06443

  SEPT '26 - MAY '27 ACADEMIC WATERFRONT RENT 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 this special home is

  Todd Gould William Pitt Sotheby's Int'l

  156 Kelsey Place, Madison, CT 06443
• 

  $1,077,000

  Sold Dec 05, 2025

  148 Country Way, Madison, CT 06443

  • 5 Beds
  • 2.5 Baths
  • 3,136 Sq Ft
  • Built 1996

  Last Sold Summary

  • 5% Above List Price
  • $343/SF
  • 62 Days On Market

  Current Estimated Value $1,079,262

  Last Listing Agent Janet Peckinpaugh William Pitt Sotheby's Int'l

  148 Country Way, Madison, CT 06443
• 

  Est $785,678

  Not Listed For Sale

  32 Lakewood Dr, Madison, CT 06443

  • 3 Beds
  • 4 Baths
  • 3,918 Sq Ft
  • Built 1987

  32 Lakewood Dr, Madison, CT 06443

  Last Sold Summary

  • 97 Days On Market
• 

  

  /40

  $725,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,908 Sq Ft

  45 Milano Pond Dr, Madison, CT 06443

  Perfectly situated on a quiet cul-de-sac with serene views of Milano Pond, this meticulously maintained 1,908 sq. ft. Colonial offers 3 bedrooms, 2.5 baths, and complete modern updates throughout. The heart of the home is a stunning, expanded kitchen featuring brand-new appliances, a massive center island, and elegant leathered granite countertops. An airy family room with vaulted ceilings

  Rob McConville RE/MAX Heritage

  45 Milano Pond Dr, Madison, CT 06443
• 

  $400,000

  Sold Mar 27, 2026

  2 Esterly Farms Rd, Madison, CT 06443

  • 1 Bed
  • 1.5 Baths
  • 1,344 Sq Ft
  • Built 1985

  Last Sold Summary

  • $298/SF
  • 52 Days On Market

  Current Estimated Value $398,037

  Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC

  2 Esterly Farms Rd, Madison, CT 06443
• 

  Est $600,219

  Not Listed For Sale

  1659 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,177 Sq Ft
  • Built 1989

  1659 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 20 Days On Market
• 

  

  /40

  $1,495,000

  Pending

  • 5 Beds
  • 5.5 Baths
  • 5,380 Sq Ft

  34 Wildcat Springs Dr, Madison, CT 06443

  Modern Charm Meets Effortless Comfort in Desirable Neighborhood Step into a bright, beautifully updated 5 bedroom, 5.5 bath home where every detail was designed for easy living and effortless entertaining. The open-concept layout flows from a sun-filled living area into a stunning chef's kitchen featuring quartz countertops, custom cabinetry, and stainless-steel appliances. Wake up to morning

  Rebecca Ellsley Higgins Group Bedford Square

  34 Wildcat Springs Dr, Madison, CT 06443
• 

  $1,600,000

  Sold Jan 23, 2026

  28 Riverside Ln, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,398 Sq Ft
  • Built 2003

  Last Sold Summary

  • $667/SF
  • 14 Days On Market

  Current Estimated Value $1,565,869

  Last Listing Agent Diana Hartman William Pitt Sotheby's Int'l

  28 Riverside Ln, Madison, CT 06443
• 

  Est $644,011

  Not Listed For Sale

  640 Summer Hill Rd, Madison, CT 06443

  • 5 Beds
  • 2.5 Baths
  • 2,404 Sq Ft
  • Built 1836

  640 Summer Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 4 Days On Market
• 

  

  /26

  $200,000

  Under Contract

  • 2 Beds
  • 1 Bath
  • 480 Sq Ft

  50 East St, Madison, CT 06443

  LOCATION ~ LOCATION ~ It matters !! 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

  Tom Clancy William Pitt Sotheby's Int'l

  50 East St, Madison, CT 06443
• 

  $935,570

  Sold Aug 14, 2025

  109 Boston Post Rd, Madison, CT 06443

  • 3 Beds
  • 3 Baths
  • 2,728 Sq Ft
  • Built 1854

  Last Sold Summary

  • 6% Below List Price
  • $343/SF
  • 42 Days On Market

  Current Estimated Value $987,004

  Last Listing Agent Jack Hill Seabury Hill REALTORS

  109 Boston Post Rd, Madison, CT 06443
• 

  Est $590,687

  Not Listed For Sale

  69 Mendingwall Cir, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,052 Sq Ft
  • Built 1977

  69 Mendingwall Cir, Madison, CT 06443

  Last Sold Summary

  • 57 Days On Market
• 

  

  /40

  $725,000

  $50K PRICE DROP Under Contract

  • 5 Beds
  • 4 Baths
  • 3,224 Sq Ft

  238 Scotland Rd, Madison, CT 06443

  Welcome to 238 Scotland Road, a rare 5-bedroom home with private in-law accommodations, pool, situated on nearly an acre of privacy. A lovingly cared-for home offering exceptional space, comfort, and versatility. Features include hardwood floors throughout, central air conditioning, and a beautiful new primary suite designed for relaxation and convenience. The heart of the home is the updated

  Debra Pardales William Pitt Sotheby's Int'l

  238 Scotland Rd, Madison, CT 06443
• 

  $220,000

  Sold Mar 25, 2026

  247 C Old Toll Rd, Madison, CT 06443

  • Land
  • 26.2 Acres
  • $8,397 per Acre

  Last Sold Summary

  • 43% Below List Price
  • 106 Days On Market

  Last Listing Agent Allyson Cotton William Pitt Sotheby's Int'l

  247 C Old Toll Rd, Madison, CT 06443
• 

  Est $671,492

  Not Listed For Sale

  7 Twilight Dr, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,646 Sq Ft
  • Built 1973

  7 Twilight Dr, Madison, CT 06443

  Last Sold Summary

  • 62 Days On Market
• 

  

  /40

  $1,350,000

  Under Contract

  • 4 Beds
  • 5 Baths
  • 5,147 Sq Ft

  11 Silo Hill, Madison, CT 06443

  Elegant Living in the coveted Bartlett neighborhood. Discover this majestic and stately colonial set on 1.11 acres in one of the town's most sought-after neighborhoods. Built in 1994 and meticulously maintained with thoughtful renovations and improvements throughout, this 4,237-square-foot residence with another 910SF of finished basement space, offers 4 bedrooms with the versatility to function

  Kirsten Adams William Pitt Sotheby's Int'l

  11 Silo Hill, Madison, CT 06443
• 

  $1,325,000

  Sold Jun 27, 2025

  50 Oak Ave, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,310 Sq Ft
  • Built 1970

  Last Sold Summary

  • 6% Above List Price
  • $574/SF
  • 10 Days On Market

  Current Estimated Value $1,383,061

  Last Listing Agent Heather Clinton Berkshire Hathaway NE Prop.

  50 Oak Ave, Madison, CT 06443
• 

  Est $601,550

  Not Listed For Sale

  1474 Durham Rd, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 2,740 Sq Ft
  • Built 1984

  1474 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 66 Days On Market
• 

  

  /38

  $735,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,657 Sq Ft

  40 Harkness Dr, Madison, CT 06443

  Discover the perfect blend of modern luxury & classic charm at 40 Harkness Drive. This beautifully renovated colonial, set on a 1.23-acre lot, offers 2,657 sq ft of thoughtfully designed living space w/ 4 bedrooms & 2.5 bathrooms. Step through the double front doors into a stunning open-concept layout. The spacious dining room seamlessly flows into a brand-new kitchen, featuring custom cabinetry,

  Lauren Freedman Coldwell Banker Realty

  40 Harkness Dr, Madison, CT 06443

Showing Results 121 - 160, Page 4 of 18