8,613

Madison, CT Homes

Section Image Section Image
  • /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

    Agent Photo

    Dana Weinstein

    Coldwell Banker Realty

    33 Madison Ave, Madison, CT 06443
  • /17

    $3,600 Per Month

    • 3 Beds
    • 2 Baths
    • 1,150 Sq Ft
    • House for Rent

    1091 Boston Post Rd, Madison, CT 06443

    ANNUAL UNFURNISHED RENTAL, AVAILABLE AUGUST 1. Located between downtown Madison and the Hammonasset State Park Beach, this 3 bedroom renovated ranch offers a comfortable life style. The house offers a deck to enjoy the outdoors, large yard, easy access to the Shoreline Greenway Trail and beach access at the end of Webster Point Road. The primary bedroom has a full bath, the other two bedrooms

    Kirsten Adams William Pitt Sotheby's Int'l

    1091 Boston Post Rd, Madison, CT 06443
  • 696 Green Hill Rd, Madison, CT 06443

    $888,000

    Sold Apr 24, 2026

    696 Green Hill Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,857 Sq Ft
    • Built 1996

    Last Sold Summary

    • $311/SF
    • 14 Days On Market

    Current Estimated Value $893,736

    Last Listing Agent Brianne Decio RE/MAX on the Bay

    696 Green Hill Rd, Madison, CT 06443
    • 11 Alexandra Ln, Madison, CT 06443

      Est $2,234,897

      Not Listed For Sale

      11 Alexandra Ln, Madison, CT 06443

      • 4 Beds
      • 5.5 Baths
      • 4,077 Sq Ft
      • Built 2015
      11 Alexandra Ln, Madison, CT 06443

      Last Sold Summary

      • 158 Days On Market

      Last Listing Agent Bob Yostos Coldwell Banker Realty

  • /24

    $1,199,000

    • 2 Beds
    • 2 Baths
    • 1,010 Sq Ft

    44 Pent Rd, Madison, CT 06443

    Discover the charm of shoreline living at this beautifully maintained cottage tucked away in one of Madison's most desirable beachside neighborhoods. Just steps from Long Island Sound and moments from Madison's vibrant town center, this unique home offers the perfect blend of coastal character, privacy, and convenience. Featuring approximately 1,010 square feet of thoughtfully designed living

    Agent Photo

    Cathy Lynch

    Coldwell Banker Realty

    44 Pent Rd, Madison, CT 06443
  • /28

    $3,500

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • House for Rent

    32 Sheep Pasture Rd, Madison, CT 06443

    ACADEMIC RENTAL. Welcome to 32 Sheep Pasture Road - a three bedroom, two bath ranch conveniently located close to everything and offering privacy in a wooded setting. Recently renovated, the open floor plan flows nicely from the foyer into the living room, dining area and kitchen. The sun room leads to the patio and private backyard. The bedrooms are nicely sized and share a hall bath with

    32 Sheep Pasture Rd, Madison, CT 06443
  • 258 Opening Hill Rd, Madison, CT 06443

    $805,500

    Sold Jun 10, 2026

    258 Opening Hill Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,627 Sq Ft
    • Built 1979

    Last Sold Summary

    • 15% Above List Price
    • $307/SF
    • 1 Day On Market

    Current Estimated Value $777,843

    Last Listing Agent Gillian Conlin Seabury Hill REALTORS

    258 Opening Hill Rd, Madison, CT 06443
    • 52 Allison Dr, Madison, CT 06443

      Est $1,469,157

      Not Listed For Sale

      52 Allison Dr, Madison, CT 06443

      • 4 Beds
      • 5 Baths
      • 4,295 Sq Ft
      • Built 2009
      52 Allison Dr, Madison, CT 06443

      Last Sold Summary

      • 179 Days On Market

      Last Listing Agent Vincent Engingro William Raveis Real Estate

  • /40

    $1,395,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 4,806 Sq Ft

    34 Beekman Place, Madison, CT 06443

    Impressive custom home in a private cul-de-Sac setting offering over 4,800 square feet of beautifully designed living space, this 4-bedroom, 3.5-bath home is set on a meticulously landscaped lot with a heated in-ground pool-perfect for both everyday living and entertaining. At the heart of the home is a stunning chef's kitchen featuring an oversized island, Viking 6-burner gas cooktop, Sub-Zero

    Agent Photo

    Cathy Lynch

    Coldwell Banker Realty

    34 Beekman Place, Madison, CT 06443
  • /19

    $3,750 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,296 Sq Ft
    • House for Rent

    66 Oak Ave, Madison, CT 06443

    Classic Farm house colonial sits directly on the waterfront! The home embodies peace and tranquility with a nod to simpler times when nature was the forefront of relaxation. Enjoy your private beach and yard and take in those glorious sunsets that Madison is known for. Enjoy a classic floor plan with a galley style kitchen, dining room, living room and a sunny closed in back porch that lets the

    Mary Edeen Berkshire Hathaway NE Prop.

    66 Oak Ave, Madison, CT 06443
  • 11 Longview Terrace, Madison, CT 06443

    $1,050,000

    Sold May 01, 2026

    11 Longview Terrace, Madison, CT 06443

    • 3 Beds
    • 3.5 Baths
    • 3,545 Sq Ft
    • Built 1993

    Last Sold Summary

    • 13% Below List Price
    • $296/SF
    • 53 Days On Market

    Current Estimated Value $1,059,624

    Last Listing Agent Bonnie Foster William Pitt Sotheby's Int'l

    11 Longview Terrace, Madison, CT 06443
    • 30 Governors Way, Madison, CT 06443

      Est $1,205,577

      Not Listed For Sale

      30 Governors Way, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 3,197 Sq Ft
      • Built 2009
      30 Governors Way, Madison, CT 06443

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Sue Woods William Pitt Sotheby's Int'l

  • /39

    $925,000

    • 3 Beds
    • 3.5 Baths
    • 3,734 Sq Ft

    3 Longview Terrace, Madison, CT 06443

    Set on a peaceful cul-de-sac in Madison's highly desirable Strathmore Farms community, 3 Longview Terrace is an exceptional stand-alone condominium home that captures the essence of luxurious coastal living. This thoughtful 3-bedroom Colonial seamlessly blends elegance and comfort, offering a flowing first-floor layout that includes a formal dining room, a living room, an eat-in kitchen that

    Agent Photo

    Betsy Anderson

    William Pitt Sotheby's Int'l

    3 Longview Terrace, Madison, CT 06443
  • /31

    $7,500 Per Month

    • 4 Beds
    • 3 Baths
    • 1,959 Sq Ft
    • House for Rent

    43 Soundview Ave, Madison, CT 06443

    Fabulous academic rental available Sept 1st through May 31st 2027. This direct waterfront four bedroom home set on a one of kind property with access to a private beach. Enjoy fabulous views from your deck, large yard and tidal pool. Plenty of space for everyone with a bedroom with full bath on the main level, Primary en suite on the second floor with private balcony and two additional bedrooms

    Sue Knapp William Pitt Sotheby's Int'l

    43 Soundview Ave, Madison, CT 06443
  • 735 Opening Hill Rd, Madison, CT 06443

    $664,600

    Sold Jan 30, 2026

    735 Opening Hill Rd, Madison, CT 06443

    • 4 Beds
    • 2 Baths
    • 2,028 Sq Ft
    • Built 1945

    Last Sold Summary

    • 8% Below List Price
    • $328/SF
    • 76 Days On Market

    Current Estimated Value $676,968

    Last Listing Agent Melanie Scull William Pitt Sotheby's Int'l

    735 Opening Hill Rd, Madison, CT 06443
    • 62 Lenore Dr, Madison, CT 06443

      Est $1,098,653

      Not Listed For Sale

      62 Lenore Dr, Madison, CT 06443

      • 4 Beds
      • 3.5 Baths
      • 3,787 Sq Ft
      • Built 2008
      62 Lenore Dr, Madison, CT 06443

      Last Sold Summary

      • 56 Days On Market

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

  • /31

    $595,000

    Under Contract
    • 1 Bed
    • 2 Baths
    • 1,569 Sq Ft

    9 Centre Village Dr, Madison, CT 06443

    Welcome to 9 Centre Village Drive, a beautifully renovated condominium offering the perfect blend of style, comfort, and convenience in one of Madison's most desirable locations. Originally built in 1985 and extensively updated in 2018, this move-in ready home features an open, light-filled floor plan designed for today's lifestyle. The spacious kitchen is the heart of the home, showcasing quartz

    Agent Photo

    Dana Weinstein

    Coldwell Banker Realty

    9 Centre Village Dr, Madison, CT 06443
  • /37

    $4,200 Per Month

    • 5 Beds
    • 4 Baths
    • 2,692 Sq Ft
    • House for Rent

    33 Ridgewood Ave, Madison, CT 06443

    Available for the Sept 10th 2026 through June 10th 2027. This sun- filled colonial has been lovingly restored for easy comfortable living. Open views of the Long Island Sound throughout this home offers room for all. Screened in wrap around porch to enjoy the warm days and nights. Updated kitchen with stainless appliances and large dining nook, mud room, office and dedicated laundry room and half

    Sue Knapp William Pitt Sotheby's Int'l

    33 Ridgewood Ave, Madison, CT 06443
  • 125 Wildcat Rd, Madison, CT 06443

    $1,000,000

    Sold Jul 07, 2026

    125 Wildcat Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 3,909 Sq Ft
    • Built 1970

    Last Sold Summary

    • $256/SF
    • 91 Days On Market

    Current Estimated Value $996,270

    Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty

    125 Wildcat Rd, Madison, CT 06443
    • 31 Samantha Ln, Madison, CT 06443

      Est $470,861

      Not Listed For Sale

      31 Samantha Ln, Madison, CT 06443

      • 3 Beds
      • 2.5 Baths
      • 2,055 Sq Ft
      • Built 1998
      31 Samantha Ln, Madison, CT 06443

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent John Campbell Compass Connecticut, LLC

  • /40

    $649,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,876 Sq Ft

    496 Green Hill Rd, Madison, CT 06443

    Charming Colonial in a central location just minutes from downtown, beautiful town beaches, schools, and with easy access to major highways. Brimming with character and timeless appeal, this home offers a wonderful layout for both everyday living and entertaining. The welcoming family room, featuring a gas fireplace and vaulted ceiling, serves as the heart of the home and flows seamlessly into

    Agent Photo

    Cathy Lynch

    Coldwell Banker Realty

    496 Green Hill Rd, Madison, CT 06443
  • /33

    $3,000 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,286 Sq Ft
    • House for Rent

    43 Neck Rd, Madison, CT 06443

    Annual Furnished Rental. Nestled in the heart of one of Madison's most sought-after beach communities, this charming and meticulously maintained home offers an effortless coastal lifestyle just moments from Overshores Beach. Thoughtfully furnished and move-in ready, the home features a welcoming floor plan with a sunny kitchen, comfortable family room, classic living room, home office, powder

    Phoebe Schreiner William Pitt Sotheby's Int'l

    43 Neck Rd, Madison, CT 06443
  • 198 Summer Hill Rd, Madison, CT 06443

    $960,000

    Sold Jul 17, 2026

    198 Summer Hill Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 3,316 Sq Ft
    • Built 1992

    Last Sold Summary

    • 7% Above List Price
    • $290/SF
    • 34 Days On Market

    Current Estimated Value $907,951

    Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty

    198 Summer Hill Rd, Madison, CT 06443
    • 4 Stephanie Ct, Madison, CT 06443

      Est $422,646

      Not Listed For Sale

      4 Stephanie Ct, Madison, CT 06443

      • 3 Beds
      • 2 Baths
      • 1,320 Sq Ft
      • Built 1996
      4 Stephanie Ct, Madison, CT 06443

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Shoreline Homes Team William Raveis Real Estate

  • /36

    $1,975,000

    $224K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,850 Sq Ft

    81 Strawberry Hill Rd, Madison, CT 06443

    Modern luxury meets sustainable living in a premier location. Set on more than two private acres in one of the area's most sought-after neighborhoods, this brand-new contemporary home offers a bright, open-concept design that blends sophisticated style with everyday comfort. At the heart of the home, the chef's kitchen impresses with a Sub-Zero refrigerator, Wolf appliances, custom cabinetry, and

    Agent Photo

    Cathy Lynch

    Coldwell Banker Realty

    81 Strawberry Hill Rd, Madison, CT 06443
  • /40

    $6,800 Per Month

    • 4 Beds
    • 5 Baths
    • 5,147 Sq Ft
    • House for Rent

    11 Silo Hill, Madison, CT 06443

    Welcome to this stately Colonial home set on 1.11 acres in Madison's coveted Bartlett neighborhood. Meticulously maintained, the interior features beautiful hardwood flooring throughout. A formal dining room sits adjacent to a private, spacious study outfitted with built-in bookshelves. The home's open-concept design revolves around an updated family room with a cozy fireplace and French doors

    Michael Hvizdo Coldwell Banker Realty

    11 Silo Hill, Madison, CT 06443
  • 534 Horse Pond Rd, Madison, CT 06443

    $440,000

    Sold May 04, 2026

    534 Horse Pond Rd, Madison, CT 06443

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Above List Price
    • $509/SF
    • 5 Days On Market

    Current Estimated Value $436,336

    Last Listing Agent Mary Polchaninoff Berkshire Hathaway NE Prop.

    534 Horse Pond Rd, Madison, CT 06443
    • 2270 Durham Rd, Madison, CT 06443

      Est $482,610

      Not Listed For Sale

      2270 Durham Rd, Madison, CT 06443

      • 3 Beds
      • 2 Baths
      • 1,916 Sq Ft
      • Built 2000
      2270 Durham Rd, Madison, CT 06443

      Last Sold Summary

      • 63 Days On Market

      Last Listing Agent Linda Toscano Coldwell Banker Realty

  • /4

    $1,890,000

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    31 Stony Lane Lot 2 Rd, Madison, CT 06443

    Indulge in refined living at our Barberry Farm Open Space subdivision with Waterside Building and Development. Your bespoke home, spanning 3,000 to 4,000+ sq ft, promises not just spacious elegance but high-end finishes and meticulous craftsmanship. Situated within walking distance to Madison beaches and a golf course, this enclave blends luxury with convenience. Revel in the exquisite details of

    Agent Photo

    Lindsay Greenberg

    William Raveis Real Estate

    31 Stony Lane Lot 2 Rd, Madison, CT 06443
  • /20

    $10,000 Per Month

    • 4 Beds
    • 4 Baths
    • 2,886 Sq Ft
    • House for Rent

    71 Beach Ave, Madison, CT 06443

    Summer furnished rental is available August 1-30th at $10,000 per month. It is also available from July 25-August 30 for $12,500. This is a wonderful opportunity for a summer vacation rental just 1 home away from a sandy, private beach on Long Island Sound in Madison. A well-built ranch located on a sweet beach lane; it offers 3 bedrooms, 2 full baths, a well-equipped modern kitchen, a large

    Carol Farmer William Raveis Real Estate

    71 Beach Ave, Madison, CT 06443
  • 86B E Wharf Rd, Madison, CT 06443

    $2,505,000

    Sold Oct 27, 2025

    86B E Wharf Rd, Madison, CT 06443

    • 4 Beds
    • 3.5 Baths
    • 3,160 Sq Ft
    • Built 2017

    Last Sold Summary

    • 5% Above List Price
    • $793/SF
    • 59 Days On Market

    Current Estimated Value $2,530,451

    Last Listing Agent Dean Mitchell William Pitt Sotheby's Int'l

    86B E Wharf Rd, Madison, CT 06443
    • 26 Tibbals Bridge Rd, Madison, CT 06443

      Est $494,838

      Not Listed For Sale

      26 Tibbals Bridge Rd, Madison, CT 06443

      • 2 Beds
      • 2 Baths
      • 1,256 Sq Ft
      • Built 1997
      26 Tibbals Bridge Rd, Madison, CT 06443

      Last Sold Summary

      • 63 Days On Market

      Last Listing Agent David Cretella Coldwell Banker Realty

  • /4

    $1,790,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    31 Stony Lane Lot 1 Rd, Madison, CT 06443

    Indulge in refined living at our Barberry Farm Open Space subdivision with Waterside Building and Development. Your bespoke home, spanning 3,000 to 4,000+ sq ft, promises not just spacious elegance but high-end finishes and meticulous craftsmanship. Situated within walking distance to Madison beaches and a golf course, this enclave blends luxury with convenience. Revel in the exquisite details of

    Agent Photo

    Lindsay Greenberg

    William Raveis Real Estate

    31 Stony Lane Lot 1 Rd, Madison, CT 06443
  • /28

    $3,500 Per Month

    • 3 Beds
    • 1 Bath
    • 1,077 Sq Ft
    • House for Rent

    6 Bower Rd, Madison, CT 06443

    Escape to the Connecticut shoreline in this beautifully furnished and tastefully styled Cape, available as an academic rental in desirable Madison. Offering 3 bedrooms and 1 full bath, the home has inviting indoor and outdoor living spaces designed for comfort throughout the academic year. Nestled on a private, lightly wooded corner lot, this charming coastal retreat offers the perfect balance of

    Calla Lord Tier 1 Real Estate

    6 Bower Rd, Madison, CT 06443
  • 53 Wellsweep Dr, Madison, CT 06443

    $778,000

    Sold Jul 10, 2026

    53 Wellsweep Dr, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,230 Sq Ft
    • Built 1970

    Last Sold Summary

    • 2% Below List Price
    • $349/SF
    • 61 Days On Market

    Current Estimated Value $789,163

    Last Listing Agent Cory Tyler Berkshire Hathaway NE Prop.

    53 Wellsweep Dr, Madison, CT 06443
    • 2364 Durham Rd, Madison, CT 06443

      Est $470,343

      Not Listed For Sale

      2364 Durham Rd, Madison, CT 06443

      • 3 Beds
      • 3 Baths
      • 2,060 Sq Ft
      • Built 1980
      2364 Durham Rd, Madison, CT 06443

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Kristopher Tramont Real Broker CT, LLC

  • /37

    $400,000

    Pending
    • 1 Bed
    • 1.5 Baths
    • 1,372 Sq Ft

    3 Esterly Farms Rd, Madison, CT 06443

    Welcome to 3 Esterly Farms Rd. Best value in Madison! Tucked away in the sought-after Esterly Farms community, this 1,372-s.f. townhouse offers a seamless blend of comfort & shoreline charm. The thoughtfully designed layout is anchored by stunning Brazilian cherry wood floors that flow throughout the main level, adding a rich, polished warmth to the home. The inviting living area features a

    Lisa Rollins Team Compass Connecticut, LLC

    3 Esterly Farms Rd, Madison, CT 06443
  • /12

    $5,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,918 Sq Ft
    • House for Rent

    30 Lawson Dr, Madison, CT 06443

    Term is 9/1/2026-6/31/2027. Price is per month. 24 hour notice to show. Beautifully furnished 3 bed, 2.1 baths house a short walk from East Wharf Beach. Rebuilt from top to bottom in 2018-19 with an open floor plan. A fenced back yard has a bluestone terrace. The living room features a gas fireplace, a well equipped kitchen has a large pantry and a vaulted ceiling family room provides ample room

    Margaret Muir William Pitt Sotheby's Int'l

    30 Lawson Dr, Madison, CT 06443
  • 338 Opening Hill Rd, Madison, CT 06443

    $628,000

    Sold Oct 24, 2025

    338 Opening Hill Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 1,792 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Above List Price
    • $350/SF
    • 34 Days On Market

    Current Estimated Value $644,710

    Last Listing Agent Barbara Goetsch William Pitt Sotheby's Int'l

    338 Opening Hill Rd, Madison, CT 06443
    • 17 Jasper Ln, Madison, CT 06443

      Est $488,304

      Not Listed For Sale

      17 Jasper Ln, Madison, CT 06443

      • 2 Beds
      • 2 Baths
      • 2,177 Sq Ft
      • Built 1993
      17 Jasper Ln, Madison, CT 06443

      Last Sold Summary

      • 151 Days On Market

      Last Listing Agent Jules Gaughran - Etes William Pitt Sotheby's Int'l

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home