Madison, CT Homes

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  /28

  $579,900

  • 3 Beds
  • 1 Bath
  • 1,077 Sq Ft

  6 Bower Rd, Madison, CT 06443

  Escape to the Connecticut shoreline with this beautifully styled Cape, ideally situated in desirable Madison. Offering 3 bedrooms and 1 full bath, this charming home features inviting indoor and outdoor living spaces designed for comfortable everyday living and relaxed coastal living. Set on a private, lightly wooded corner lot, the property offers a peaceful sense of privacy while remaining

  Calla Lord Tier 1 Real Estate

  6 Bower 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 $569,940

  Last Listing Agent Luke Florian SSG Real Estate LLC

  9 Old Farms Rd, Madison, CT 06443
• 

  Est $985,308

  Not Listed For Sale

  22 Northwood Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 3,765 Sq Ft
  • Built 1994

  22 Northwood Rd, Madison, CT 06443

  Last Sold Summary

  • 124 Days On Market

  Last Listing Agent Rhonda Mesenbourg Alpern and Mesenbourg LLC
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  /39

  $795,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,572 Sq Ft

  3 Little Hollow Rd, Madison, CT 06443

  Welcome home to this classic four-bedroom Colonial offering timeless charm, modern updates, and an ideal layout for everyday living, complete with gorgeous wide plank flooring throughout. Freshly updated, the home features stylish new light fixtures and major mechanical upgrades, including a new roof (2022) and a new Carrier HVAC system for the second floor (2026). At the heart of the main level

  Sue Woods William Pitt Sotheby's Int'l

  3 Little Hollow Rd, Madison, CT 06443
• 

  $1,750,000

  Sold Aug 31, 2026

  33 River Edge Farms Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,416 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Above List Price
  • $724/SF
  • 4 Days On Market

  Current Estimated Value $1,252,185

  Last Listing Agent Kelly Whiteman William Raveis Real Estate

  33 River Edge Farms Rd, Madison, CT 06443
• 

  Est $531,480

  Not Listed For Sale

  289 Old Toll Rd, Madison, CT 06443

  • 10 Beds
  • 3 Baths
  • 3,039 Sq Ft
  • Built 1938

  289 Old Toll Rd, Madison, CT 06443

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Lauren Freedman Coldwell Banker Realty
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  /36

  $499,900

  $24K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  35 Aileen Dr, Madison, CT 06443

  First Time Offered In 25 Years. This contemporary raised ranch, set on 2.36 secluded acres, is located in a quiet cul-de-sac neighborhood just minutes to town. The living room with hardwood floors features a cathedral ceiling with beams, a wood burning fireplace, floor to ceiling windows with double sliders to a deck with built in bench, perfect for morning coffee or evening enjoyment. The

  Leslie Richo William Raveis Real Estate

  35 Aileen Dr, Madison, CT 06443
• 

  $437,000

  Sold Feb 26, 2026

  1543 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 3,711 Sq Ft
  • Built 1930

  Last Sold Summary

  • 3% Above List Price
  • $118/SF
  • 31 Days On Market

  Current Estimated Value $448,327

  Last Listing Agent Rob McConville RE/MAX Heritage

  1543 Durham Rd, Madison, CT 06443
• 

  Est $632,998

  Not Listed For Sale

  316 Race Hill Rd, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 2,481 Sq Ft
  • Built 1964

  316 Race Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Sheila Tinn-Murphy Berkshire Hathaway NE Prop.
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  /34

  $3,200,000

  New Construction

  • 5 Beds
  • 3.5 Baths
  • 4,937 Sq Ft

  22 Stone Rd, Madison, CT 06443

  Experience coastal Madison living with beach rights in this to be built 5-bedroom, 3.5-bathroom home featuring 4,937 square feet of high-end craftsmanship. Designed with an airy, open layout, the main level boasts 9'+ ceilings, Red Oak hardwood floors, and a chef's kitchen equipped with white Shaker cabinetry, quartz countertops, a butler's pantry, and premium Sub-Zero, Wolf, and Bosch

  Rob McConville RE/MAX Heritage

  22 Stone Rd, Madison, CT 06443
• 

  $1,200,000

  Sold Mar 13, 2026

  5 Evarts Ln, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 2,418 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Above List Price
  • $496/SF
  • 33 Days On Market

  Current Estimated Value $1,220,572

  Last Listing Agent Cathy Lynch Coldwell Banker Realty

  5 Evarts Ln, Madison, CT 06443
• 

  Est $794,215

  Not Listed For Sale

  79 Dream Lake Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,294 Sq Ft
  • Built 1986

  79 Dream Lake Dr, Madison, CT 06443

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Ryan Casey William Raveis Real Estate
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  /6

  $1,250,000

  New Construction Pending

  • 2 Beds
  • 3.5 Baths
  • 2,000 Sq Ft

  0 Bushnell Ln, Madison, CT 06443

  Location, location, location! Build your home in the shoreline town of Madison! This proposed 2000sf modern farmhouse style home has a first floor primary bedroom, 3 full baths with additional space for an office, a rec room and an open floor plan. Vaulted ceilings, lots of natural light and energy efficiency make this build stand out. The proposed design can be modified to meet your needs.

  Justin Bradley Coldwell Banker Realty

  0 Bushnell Ln, Madison, CT 06443
• 

  $561,500

  Sold Mar 09, 2026

  21 Apple Way, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 1,414 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Above List Price
  • $397/SF
  • 2 Days On Market

  Current Estimated Value $609,801

  Last Listing Agent Rachel Welch William Raveis Real Estate

  21 Apple Way, Madison, CT 06443
• 

  Est $543,562

  Not Listed For Sale

  71 Old Toll Rd, Madison, CT 06443

  • 3 Beds
  • 3 Baths
  • 2,092 Sq Ft
  • Built 1810

  71 Old Toll Rd, Madison, CT 06443

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Tom Clancy William Pitt Sotheby's Int'l
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  /27

  $450,000

  $20K PRICE DROP Pending

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

  12 W Sussex Place Unit 12, Madison, CT 06443

  Welcome to effortless, low-maintenance living in this beautifully maintained 2-bedroom, 1.5-bath condominium, built in 2006. Offering 1,296 square feet of thoughtfully designed living space, plus approximately 608 square feet of finished lower-level space, this home provides exceptional flexibility for today's lifestyle. The bright, open floor plan features hardwood floors, a spacious kitchen

  Mark McElrath William Pitt Sotheby's Int'l

  12 W Sussex Place Unit 12, Madison, CT 06443
• 

  $1,250,000

  Sold Apr 21, 2026

  908 Boston Post Rd Unit 908, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,368 Sq Ft
  • Built 2021

  Last Sold Summary

  • 7% Below List Price
  • $528/SF
  • 110 Days On Market

  Last Listing Agent Cathy Lynch Coldwell Banker Realty

  908 Boston Post Rd Unit 908, Madison, CT 06443
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  Est $1,046,693

  Not Listed For Sale

  17 Buck Hill Rd, Madison, CT 06443

  • 5 Beds
  • 4 Baths
  • 5,069 Sq Ft
  • Built 1994

  17 Buck Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Linda Toscano Coldwell Banker Realty
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  /40

  $574,000

  $5K PRICE DROP Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  250 Legend Hill Rd, Madison, CT 06443

  Welcome to 250 Legend Hill Road, a beautifully maintained townhouse condominium in Madison's sought-after Legend Hill community with a tennis/pickleball courts, a Gunite pool, and a clubhouse housed in the original cobblestone mansion. This particular home is positioned to capture both morning and afternoon light, and distant views of Long Island Sound. Inside, the first floor features a gracious

  Kelly Whiteman William Raveis Real Estate

  250 Legend Hill Rd, Madison, CT 06443
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  $693,000

  Sold Jan 30, 2026

  29 Circle Beach Rd, Madison, CT 06443

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1935

  Last Sold Summary

  • 1% Below List Price
  • $962/SF
  • 5 Days On Market

  Current Estimated Value $720,498

  Last Listing Agent Gary Piccirillo RE/MAX Right Choice

  29 Circle Beach Rd, Madison, CT 06443
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  Est $639,063

  Not Listed For Sale

  1225 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 1,747 Sq Ft
  • Built 1952

  1225 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Carol Farmer William Raveis Real Estate
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  /31

  $489,000

  • 2 Beds
  • 2.5 Baths
  • 1,606 Sq Ft

  23 Esterly Farms Rd, Madison, CT 06443

  Welcome to 23 Esterly Farms, an exceptional end-unit townhouse offering the perfect blend of style, comfort, and turnkey convenience in one of Madison's most sought-after condominium communities. This meticulously maintained 2-bedroom, 2.5-bath home has been thoughtfully updated throughout, allowing you to move right in and enjoy worry-free living. The sun-filled interior showcases fresh paint,

  Joe Scarpellino Coldwell Banker Realty

  23 Esterly Farms Rd, Madison, CT 06443
• 

  $775,000

  Sold Jan 16, 2026

  48 Shepherds Trail, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 4,879 Sq Ft
  • Built 1991

  Last Sold Summary

  • 9% Below List Price
  • $159/SF
  • 170 Days On Market

  Current Estimated Value $855,868

  Last Listing Agent Erin Connelly Coldwell Banker Realty

  48 Shepherds Trail, Madison, CT 06443
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  Est $586,985

  Not Listed For Sale

  138 Squires Rd, Madison, CT 06443

  • 4 Beds
  • 1.5 Baths
  • 1,868 Sq Ft
  • Built 1972

  138 Squires Rd, Madison, CT 06443

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Samantha Celentano Coldwell Banker Realty
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  /39

  $739,900

  Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,368 Sq Ft

  393 Copse Rd, Madison, CT 06443

  Move-in ready and located in a desirable Madison neighborhood near schools and Bauer Park, this expanded Cape offers space, flexibility, and modern updates throughout. Recent improvements include updated kitchens, all 3.5 renovated bathrooms, and new flooring, creating a fresh and welcoming feel. The main level features an eat-in kitchen, formal dining room, and a family room with vaulted

  Tania Melo Coldwell Banker Realty

  393 Copse Rd, Madison, CT 06443
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  $799,000

  Sold Nov 25, 2025

  52 Copse Rd, Madison, CT 06443

  • 3 Beds
  • 1 Bath
  • 1,382 Sq Ft
  • Built 1850

  Last Sold Summary

  • $578/SF
  • 11 Days On Market

  Current Estimated Value $811,696

  Last Listing Agent Laureen Kennedy Coldwell Banker Realty

  52 Copse Rd, Madison, CT 06443
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  Est $853,453

  Not Listed For Sale

  191 Concord Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 3,075 Sq Ft
  • Built 1978

  191 Concord Dr, Madison, CT 06443

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Kirsten Adams William Pitt Sotheby's Int'l
• 

  

  /20

  $500,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  18 Saint Francis Woods Rd, Madison, CT 06443

  A Fantastic Opportunity in an Adorable Neighborhood Welcome to a home that offers incredible potential, a great location, and peace of mind with many of the major systems already updated. While this property needs work and updating, the big-ticket items have been taken care of, making this an exciting opportunity for someone looking to build equity and create a home that truly reflects their

  Meig Walz Newcomb Coldwell Banker Realty

  18 Saint Francis Woods Rd, Madison, CT 06443
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  $700,000

  Sold May 01, 2026

  30 Church Ln, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,908 Sq Ft
  • Built 1972

  Last Sold Summary

  • 17% Above List Price
  • $241/SF
  • 28 Days On Market

  Current Estimated Value $701,261

  Last Listing Agent Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  30 Church Ln, Madison, CT 06443
• 

  Est $917,146

  Not Listed For Sale

  21 Heatherwood Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,712 Sq Ft
  • Built 1976

  21 Heatherwood Dr, Madison, CT 06443

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Dana Weinstein Coldwell Banker Realty
• 

  

  /39

  $1,295,000

  Open Sun 11AM - 1PM $55K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 4,022 Sq Ft

  420 Summer Hill Rd, Madison, CT 06443

  Set on nearly two private acres in a quiet, peaceful setting, this beautifully maintained home offers more than 4,000 square feet of spacious, light-filled living. Built in 1999 and presented in excellent condition, the home features an inviting open floor plan, generously sized rooms, four large bedrooms, and two fireplaces that add warmth and character. Abundant natural light highlights the

  Mark McElrath William Pitt Sotheby's Int'l

  420 Summer Hill Rd, Madison, CT 06443
• 

  $1,397,000

  Sold Sep 23, 2026

  35 Neptune Ave, Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 2,052 Sq Ft
  • Built 1950

  Last Sold Summary

  • 27% Above List Price
  • $681/SF
  • 2 Days On Market

  Current Estimated Value $1,175,200

  Last Listing Agent Kirsten Adams William Pitt Sotheby's Int'l

  35 Neptune Ave, Madison, CT 06443
• 

  Est $1,767,673

  Not Listed For Sale

  51 Buck Hill Rd, Madison, CT 06443

  • 5 Beds
  • 7 Baths
  • 4,994 Sq Ft
  • Built 2006

  51 Buck Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 263 Days On Market

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

  

  /19

  $142,900

  $7K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 396 Sq Ft

  92 4th St, Madison, CT 06443

  Nestled in the heart of picturesque Madison, this charming 2-bedroom, 1-bathroom seasonal cottage offers a serene sanctuary for enjoying summers along the shoreline. With a cozy living space, this quaint abode is perfectly designed for those seeking a peaceful beachside getaway. As you step inside, you're greeted by a warm and inviting atmosphere that captures the essence of coastal living. The

  Melanie Abbott William Pitt Sotheby's Int'l

  92 4th St, Madison, CT 06443
• 

  $1,070,000

  Sold Jul 23, 2026

  351 Bartlett Dr, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 4,015 Sq Ft
  • Built 1994

  Last Sold Summary

  • 8% Above List Price
  • $267/SF
  • 4 Days On Market

  Current Estimated Value $1,053,361

  Last Listing Agent Susan Santoro William Pitt Sotheby's Int'l

  351 Bartlett Dr, Madison, CT 06443
• 

  Est $1,052,869

  Not Listed For Sale

  44 Buck Hill Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 4,448 Sq Ft
  • Built 1994

  44 Buck Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 76 Days On Market

  Last Listing Agent Linda Toscano Coldwell Banker Realty
• 

  

  /40

  $749,900

  $20K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,056 Sq Ft

  2125 Durham Rd, Madison, CT 06443

  Tucked away on a sweet cul-de-sac at the end of a private road, well off of Route 79, this spacious 4-bedroom Colonial welcomes you with a wonderful sense of privacy and tranquility. Enjoy plenty of room to gather, relax, and make yourself at home, including a full finished walk out basement with endless possibilities. This low maintenance home features a new roof, hardwood floors throughout, a

  Jane Cardarelli William Raveis Real Estate

  2125 Durham Rd, Madison, CT 06443
• 

  $430,000

  Sold Jun 12, 2026

  107 Horse Pond Rd, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1948

  Last Sold Summary

  • 1% Above List Price
  • $498/SF
  • 63 Days On Market

  Current Estimated Value $429,458

  Last Listing Agent Victoria Tavares William Raveis Real Estate

  107 Horse Pond Rd, Madison, CT 06443
• 

  Est $816,654

  Not Listed For Sale

  426 Summer Hill Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,830 Sq Ft
  • Built 1989

  426 Summer Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 131 Days On Market

  Last Listing Agent Stephanie Jacobs Sunset Creek Realty, LLC
• 

  

  /18

  $500,000

  Under Contract

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

  14 Hampshire Rd, Madison, CT 06443

  Charming two-bedroom ranch in the desirable North Kensington community. Enjoy central air conditioning, gas heat, and a beautiful screened-in porch overlooking the pond-an inviting space to relax and unwind. The home features generously sized bedrooms and two full bathrooms, offering comfort and convenience for guests and everyday living. Cozy up by the gas fireplace, which is easy to turn on and

  Meig Walz Newcomb Coldwell Banker Realty

  14 Hampshire Rd, Madison, CT 06443

Showing Results 161 - 200, Page 5 of 18