Madison, CT Homes

• 

  Est $670,364 Not Listed For Sale

  15 Bentwater Ln, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,248 Sq Ft
  • Built 1994

  15 Bentwater Ln, Madison, CT 06443

  Last Sold Summary

  • 3% Above List Price
  • $290/SF
  • 18 Days On Market

  • Last Sold Price $651,000
  • Jun 13, 2024

  Last Listing Agent Pam Kadamus William Pitt
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  /29

  $519,000

  • 2 Beds
  • 2 Baths
  • 1,476 Sq Ft

  4 Currycross Rd Unit 4, Madison, CT 06443

  Welcome to highly desirable Windermere East. Windermere is nestled in a private picture perfect setting along the Madison Shoreline. 4 Currycross Road is a charming free standing home with 2 spacious bedrooms, a pretty backyard, and one detached garage just steps to your front door. Home has been freshly painted and boast a lovely open floor plan with a wood burning fireplace, cathedral ceiling,

  Terry Morgan CT Realty Exchange, LLC

  4 Currycross Rd Unit 4, 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 $538,564

  Last Listing Agent Renee Salafia William Raveis Real Estate

  Unlisted Address
• 

  Est $751,071 Not Listed For Sale

  67 Devonshire Ln, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 3,726 Sq Ft
  • Built 1997

  67 Devonshire Ln, Madison, CT 06443

  Last Sold Summary

  • 8% Above List Price
  • $186/SF
  • 37 Days On Market

  • Last Sold Price $692,500
  • Sep 24, 2024

  Last Listing Agent Jessica Kimball William Raveis Real Estate
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  /33

  $595,000

  • 2 Beds
  • 2 Baths
  • 2,560 Sq Ft

  10 Runnymede Ln, Madison, CT 06443

  Nestled in the highly sought-after Windermere East community, this rare free-standing condo offers the perfect blend of privacy, comfort, and coastal charm in beautiful Madison. Enjoy serene river views and a peaceful setting just moments from the shoreline. This well-maintained home features 2 bedrooms and 2 full baths, a spacious fireplaced living room, and a bright kitchen ideal for everyday

  Laura Cariati William Raveis Real Estate

  10 Runnymede 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 $657,192

  Last Listing Agent Camille Ackermann Berkshire Hathaway NE Prop.

  94 Boston Post Rd, Madison, CT 06443
• 

  Est $564,235 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

  • 3% Above List Price
  • $284/SF
  • 23 Days On Market

  • Last Sold Price $548,000
  • Aug 02, 2024

  Last Listing Agent Amy Kirst William Pitt
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  /16

  $199,000

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft

  63GG Dudley Ln, Madison, CT 06443

  Discover the ultimate summer retreat at 63GG Dudley Lane, a completely remodeled two-bedroom cottage located in the desirable and private DeSabato's Camp community. This turn-key home is offered fully furnished and features a bright, open interior with upgraded cabinetry and modern finishes throughout that maximize space and style. The outdoor living space is exceptional, boasting a massive rear

  Laura Ronghi Napoli Realty LLC

  63GG Dudley Ln, 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 $883,287

  Last Listing Agent Cathy Lynch Coldwell Banker Realty

  15 Buttonball Ln, Madison, CT 06443
• 

  Est $715,817 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

  • 16% Above List Price
  • $265/SF
  • 1 Day On Market

  • Last Sold Price $616,000
  • Jun 26, 2023

  Last Listing Agent Phoebe Schreiner William Pitt
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  /38

  $424,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 864 Sq Ft

  107 Horse Pond Rd, Madison, CT 06443

  Set on 1.75 private acres in the heart of Madison, this inviting ranch offers a unique blend of comfort, versatility, and opportunity. Tucked away with a sense of privacy yet just moments from town, the property features a charming main residence along with a fully equipped detached cottage-ideal for today's flexible lifestyles. The main home is filled with natural light and showcases hardwood

  Victoria Tavares William Raveis Real Estate

  107 Horse Pond Rd, 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 $1,084,722

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

  148 Country Way, Madison, CT 06443
• 

  Est $764,115 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

  • 19% Above List Price
  • $245/SF
  • 2 Days On Market

  • Last Sold Price $640,000
  • Oct 06, 2023

  Last Listing Agent Linda Toscano Coldwell Banker Realty
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  /2

  $350,000

  • 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
• 

  $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 $386,255

  Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC

  2 Esterly Farms Rd, Madison, CT 06443
• 

  Est $670,854 Not Listed For Sale

  31 Lakewood Dr, Madison, CT 06443

  • 3 Beds
  • 3 Baths
  • 2,954 Sq Ft
  • Built 1998

  31 Lakewood Dr, Madison, CT 06443

  Last Sold Summary

  • 12% Above List Price
  • $203/SF
  • 19 Days On Market

  • Last Sold Price $600,000
  • Jun 09, 2023

  Last Listing Agent Nikki Travaglino William Pitt
• 

  

  /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
• 

  $1,600,000 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 $1,584,289

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

  28 Riverside Ln, Madison, CT 06443
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  Est $746,171 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

  • 19% Above List Price
  • $199/SF
  • 80 Days On Market

  • Last Sold Price $625,000
  • Mar 15, 2024

  Last Listing Agent Alicia Mahon William Pitt
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  /36

  $519,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,296 Sq Ft

  1 Wilshire Rd Unit B, Madison, CT 06443

  Kensington Acres South! Here is your opportunity to live in a great community of well cared for condominiums located just a short distance from downtown Madison and Hammonasset State Park. Unit 1B is an exceptional, refreshed property with a well appointed kitchen, spacious & open living-dining area on the main level. Two large bedrooms and two full baths are on the second level. Hardwood floors

  Suzanne McConville William Raveis Real Estate

  1 Wilshire Rd Unit B, 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 $768,306 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

  • 4% Above List Price
  • $189/SF
  • 97 Days On Market

  • Last Sold Price $740,000
  • Jan 10, 2025

  Last Listing Agent Cheryl Bertini Berkshire Hathaway Home Services
• 

  

  /35

  $225,000

  • 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
• 

  $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 $984,536

  Last Listing Agent Jack Hill Seabury Hill REALTORS

  109 Boston Post Rd, Madison, CT 06443
• 

  Est $861,074 Not Listed For Sale

  235 Devonshire Ln, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 3,025 Sq Ft
  • Built 2002

  235 Devonshire Ln, Madison, CT 06443

  Last Sold Summary

  • 28% Above List Price
  • $223/SF
  • 2 Days On Market

  • Last Sold Price $675,000
  • May 19, 2023

  Last Listing Agent Susan Santoro William Pitt
• 

  

  /31

  $1,775,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,976 Sq Ft

  11 Middle Beach Rd, Madison, CT 06443

  WOW water views! Vintage shingle style. The charm of old Madison with modern comforts. This Sound facing getaway offers three bedrooms and three full baths. The main level is versatile with a separate den/family room and a living room with fireplace. The Gedney-designed kitchen with beautiful Tiger Maple cabinetry is open to the dining area and leads to a private rear patio and deep landscaped

  Margaret Muir William Pitt Sotheby's Int'l

  11 Middle Beach Rd, Madison, CT 06443
• 

  $225,000 Sold Jun 12, 2025

  0 Bishop Ln Unit Lot. 2, Madison, CT 06443

  • Land
  • 1.2 Acres
  • $187,500 per Acre

  Last Sold Summary

  • 40% Below List Price
  • 280 Days On Market

  Last Listing Agent Stacy Bucci Coldwell Banker Realty

  0 Bishop Ln Unit Lot. 2, Madison, CT 06443
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  Est $578,951 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

  • 2% Above List Price
  • $260/SF
  • 20 Days On Market

  • Last Sold Price $565,000
  • Nov 27, 2024

  Last Listing Agent Greg robbins Houlihan Lawrence WD
• 

  

  /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
• 

  $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 $1,357,210

  Last Listing Agent Heather Clinton Berkshire Hathaway NE Prop.

  50 Oak Ave, Madison, CT 06443
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  Est $629,549 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

  • 20% Above List Price
  • $218/SF
  • 4 Days On Market

  • Last Sold Price $525,000
  • Jun 23, 2023

  Last Listing Agent Emily Lovejoy William Raveis Real Estate
• 

  

  /40

  $825,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,462 Sq Ft

  40 Hull Rd, Madison, CT 06443

  Seldom-available offering in one of Madison's premier neighborhoods. This versatile split-level home sits on a double lot spanning over 2 acres, offering exceptional privacy and room to grow. Set back from the street with a circular driveway, the property unfolds to reveal 4+ bedrooms, 3 full baths, and flexible living spaces designed for how you live today. The kitchen, which is the heart of the

  Sue Woods William Pitt Sotheby's Int'l

  40 Hull Rd, Madison, CT 06443
• 

  $551,000 Sold Jan 20, 2026

  9 Old Farms Rd, Madison, CT 06443

  • 4 Beds
  • 1.5 Baths
  • 1,828 Sq Ft
  • Built 1973

  Last Sold Summary

  • 4% Below List Price
  • $301/SF
  • 82 Days On Market

  Current Estimated Value $558,456

  Last Listing Agent Luke Florian SSG Real Estate LLC

  9 Old Farms Rd, Madison, CT 06443
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  Est $571,785 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

  • 7% Above List Price
  • $261/SF
  • 57 Days On Market

  • Last Sold Price $535,000
  • Jul 15, 2024

  Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty
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  /40

  $699,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,477 Sq Ft

  58 Neck Rd, Madison, CT 06443

  **OFFERS DUE MONDAY 3/30 AT NOON*** LOCATION! LOCATION!! LOCATION!! Ideally situated south of Route 1 in one of Madison's most desirable beach communities, this move in ready 3 bedroom, 2 bath Cape offers a perfect blend of coastal charm, modern updates, and exceptional convenience. Just a short stroll to the Madison Surf Club and minutes from downtown Madison, this 1,477 sq ft home sits on a

  Joe Scarpellino Coldwell Banker Realty

  58 Neck Rd, Madison, CT 06443
• 

  $1,225,000 Sold Jun 19, 2025

  16 Rockledge Dr, Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 2,340 Sq Ft
  • Built 1957

  Last Sold Summary

  • 6% Below List Price
  • $524/SF
  • 46 Days On Market

  Current Estimated Value $1,246,020

  Last Listing Agent Bob Yostos Coldwell Banker Realty

  16 Rockledge Dr, Madison, CT 06443
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  Est $645,099 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

  • 5% Above List Price
  • $232/SF
  • 62 Days On Market

  • Last Sold Price $615,000
  • Aug 23, 2024

  Last Listing Agent Emily Lovejoy William Raveis Real Estate
• 

  

  /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
• 

  $835,000 Sold Sep 15, 2025

  35 Bishop Ln, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,568 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Above List Price
  • $325/SF
  • 19 Days On Market

  Current Estimated Value $854,115

  Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC

  35 Bishop Ln, Madison, CT 06443
• 

  Est $591,446 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

  • 9% Above List Price
  • $199/SF
  • 66 Days On Market

  • Last Sold Price $545,000
  • Mar 01, 2024

  Last Listing Agent Alicia Mahon William Pitt

Showing Results 121 - 160, Page 4 of 18