Madison, CT Homes

• 

  Est $610,049

  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
• 

  

  

  /23

  $519,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,666 Sq Ft

  21 Pierce Ln, Madison, CT 06443

  Welcome to 21 Pierce Lane-an exceptional opportunity to own in one of Madison's most desirable in-town locations. Tucked away on a quiet dead-end cul-de-sac, this 3-bedroom home offers privacy, community, and incredible potential. Set on a level lot backing to Land Trust property with nearby hiking trails, this home combines peaceful surroundings with everyday convenience just minutes to

  Steve Jones Jr KW Legacy Partners

  21 Pierce Ln, 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 $421,367

  Last Listing Agent Victoria Tavares William Raveis Real Estate

  107 Horse Pond Rd, Madison, CT 06443
• 

  Est $971,977

  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
• 

  

  

  /28

  $579,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 3,184 Sq Ft

  187 Old Toll Rd, Madison, CT 06443

  Originally built in the 1970's, this home has been thoughtfully transformed over time with extensive additions and updates that make it hard to imagine it's the same house. Newer mechanicals, Anderson windows, new interior doors and beautifully renovated kitchen & baths ensure a truly turnkey experience. Set well back from the road on 2.34 landscaped acres, this property offers privacy with

  Judy Dannemann William Raveis Real Estate

  187 Old Toll Rd, Madison, CT 06443
• 

  $465,000

  Sold Mar 05, 2026

  24 Railroad Ave, Madison, CT 06443

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Built 1940

  Last Sold Summary

  • 2% Below List Price
  • $465/SF
  • 75 Days On Market

  Current Estimated Value $464,196

  Last Listing Agent Remi Tremblay William Raveis Real Estate

  24 Railroad Ave, Madison, CT 06443
• 

  Est $540,269

  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
• 

  

  /35

  $469,900

  Pending

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

  18 Saint Francis Woods Rd, Madison, CT 06443

  Spacious Split-level home with deck, open porch and patio overlooking large, level lot. Three levels of living space plus unfinished basement and partial attic for storage. Main level includes Living room, Dining room w/sliders to deck and Kitchen with all newer appliances. Upper level with 3 bedrooms and 2 full baths. Third level has Family room with fireplace and access to garage, patio and

  Christine Fappiano Shoreline Real Estate Company

  18 Saint Francis Woods Rd, Madison, CT 06443
• 

  $1,225,000

  Sold Feb 18, 2026

  41 Allison Dr, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 3,609 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $339/SF
  • 66 Days On Market

  Current Estimated Value $1,232,974

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

  41 Allison Dr, Madison, CT 06443
• 

  Est $1,028,393

  Not Listed For Sale

  35 Georgetown Cir, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 3,004 Sq Ft
  • Built 1978

  35 Georgetown Cir, Madison, CT 06443

  Last Sold Summary

  • 1 Day On Market
• 

  

  /31

  $575,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,490 Sq Ft

  111 Scotland Rd, Madison, CT 06443

  Located close to the center of town, beaches and both I95 and train station this home is in an ideal location. There are three spacious bedrooms, two bathrooms and hardwood throughout. The kitchen features granite countertops, tile backsplash, and opens into a spacious dining room. The sun filled living room stretches across the front of the house. The back yard is spacious and level. This home

  Rob McConville RE/MAX Heritage

  111 Scotland Rd, Madison, CT 06443
• 

  $265,000

  Sold Feb 19, 2026

  268 Durham Rd, Madison, CT 06443

  • Land
  • 2.29 Acres
  • $115,721 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 24 Days On Market

  Current Estimated Value $267,545

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

  268 Durham Rd, Madison, CT 06443
• 

  Est $797,248

  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
• 

  

  /35

  $2,650,000

  • 4 Beds
  • 4.5 Baths
  • 6,194 Sq Ft

  24 Indigo Trail, Madison, CT 06443

  Luxury Property Auction: 11-25 June. Current High Bid: $1,400,000. Estimated Sale Price: $2,200,000 - $2,800,000. Set on 5.65 secluded acres in the heart of Madison, this exceptional English Georgian custom home offers a rare blend of timeless architecture, refined craftsmanship, and natural beauty. Surrounded by mature woodlands, the property is a private retreat, complete with a gently winding

  Lee Leslie Concierge Auctions, LLC

  24 Indigo Trail, Madison, CT 06443
• 

  $885,000

  Sold Mar 19, 2026

  198 Green Hill Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,663 Sq Ft
  • Built 2013

  Last Sold Summary

  • 1% Above List Price
  • $332/SF
  • 19 Days On Market

  Current Estimated Value $885,537

  Last Listing Agent Kayla Chasse Compass Connecticut, LLC

  198 Green Hill Rd, Madison, CT 06443
• 

  Est $866,610

  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
• 

  

  /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
• 

  $587,500

  Sold Mar 31, 2026

  67 Boston Post Rd Unit 8, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 1,816 Sq Ft
  • Built 2018

  Last Sold Summary

  • 1% Below List Price
  • $324/SF
  • 56 Days On Market

  Current Estimated Value $586,112

  Last Listing Agent Dana Weinstein Coldwell Banker Realty

  67 Boston Post Rd Unit 8, Madison, CT 06443
• 

  Est $1,632,824

  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
• 

  

  /36

  $625,000

  • 2 Beds
  • 2.5 Baths
  • 1,498 Sq Ft

  21 Centre Village Dr, Madison, CT 06443

  Beautifully updated two-bedroom townhouse in Centre Village. One of only four 2-bedroom units in complex. Walkable and bikeable to town green, restaurants, cinema, shops and all three town beaches! Centre Village is a private, modestly sized complex (22 units), nicely landscaped with individual patios and yards, ample parking, city water and natural gas off street. Seller has renovated inside and

  Pam Kadamus William Pitt Sotheby's Int'l

  21 Centre Village Dr, Madison, CT 06443
• 

  $815,000

  Sold Jul 11, 2025

  27 Hammonassett Meadows Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,276 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Above List Price
  • $358/SF
  • 3 Days On Market

  Current Estimated Value $827,102

  Last Listing Agent Leigh Whiteman William Raveis Real Estate

  27 Hammonassett Meadows Rd, Madison, CT 06443
• 

  Est $983,719

  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
• 

  

  /40

  $1,399,000

  $276K PRICE DROP

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

  420 Summer Hill Rd, Madison, CT 06443

  Privately positioned on nearly two acres in one of Madison's most desirable areas, this expansive Colonial offers a rare combination of privacy, scale, and convenience. Surrounded by natural beauty, the property feels secluded while remaining just minutes from the shoreline and Madison's charming town center, known for its dining, boutique shops, and coastal New England character. A true

  Adriana Radu Coldwell Banker Realty

  420 Summer Hill Rd, Madison, CT 06443
• 

  $779,000

  Sold Feb 03, 2026

  13 Longview Terrace, Madison, CT 06443

  • 3 Beds
  • 3.5 Baths
  • 3,772 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Below List Price
  • $207/SF
  • 69 Days On Market

  Current Estimated Value $794,258

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

  13 Longview Terrace, Madison, CT 06443
• 

  Est $758,350

  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
• 

  

  /37

  $1,150,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 4,019 Sq Ft

  86 Quail Run, Madison, CT 06443

  Mark your calendars! Showings begin on Thursday, May 7th. Welcome home to this beautifully designed 4-bedroom Colonial offering space, style, and an exceptional floor plan! Step into the impressive two-story foyer with elegant marble tile floors that set the tone for what's to come. The formal living room flows seamlessly into a sun-filled family room featuring a charming bay window, vaulted

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  86 Quail Run, Madison, CT 06443
• 

  $470,000

  Sold Oct 01, 2025

  22 Centre Village Dr, Madison, CT 06443

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

  Last Sold Summary

  • 10% Below List Price
  • $300/SF
  • 126 Days On Market

  Current Estimated Value $471,516

  Last Listing Agent Emily Lovejoy William Raveis Real Estate

  22 Centre Village Dr, Madison, CT 06443
• 

  Est $964,378

  Not Listed For Sale

  398 Summer Hill Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 3,470 Sq Ft
  • Built 1988

  398 Summer Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 3 Days On Market
• 

  

  /39

  $2,495,000

  $255K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,321 Sq Ft

  81A Middle Beach Rd, Madison, CT 06443

  NEW PRICE. Set back from Middle Beach Rd and sited 25' above sea level (so no flood insurance needed!) with deeded beach rights and views of Long Island Sound is a like-new (completed in 2023) charming 4 bedroom, Cape Cod style home on an unusually large 1.12 acre lot. The open plan's first floor has a cathedral ceiling in the living room with a gas-lit stone fireplace, a dining area, and a fully

  Margaret Muir William Pitt Sotheby's Int'l

  81A Middle Beach Rd, Madison, CT 06443
• 

  $630,000

  Sold Dec 12, 2025

  81 Bartlett Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,088 Sq Ft
  • Built 1971

  Last Sold Summary

  • 3% Below List Price
  • $302/SF
  • 119 Days On Market

  Current Estimated Value $634,929

  Last Listing Agent Lauren Freedman Coldwell Banker Realty

  81 Bartlett Dr, Madison, CT 06443
• 

  Est $1,081,847

  Not Listed For Sale

  48 Lenore Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 5,125 Sq Ft
  • Built 2004

  48 Lenore Dr, Madison, CT 06443

  Last Sold Summary

  • 80 Days On Market
• 

  

  /37

  $605,000

  Under Contract

  • 2 Beds
  • 3 Baths
  • 2,135 Sq Ft

  5 Thelbridge St Unit 5, Madison, CT 06443

  One person's loss is another one's gain! You have a second chance to make this this lovely property yours. It is more than a home --it's a lifestyle. Tucked into one of Madison's most sought-after communities at Windermere East, you'll feel at home the moment you enter the front door. The bright, open floor plan provides casual, coastline living at its best. The remodeled kitchen with granite

  Joanne Breen ERA Hart Sargis-Breen

  5 Thelbridge St Unit 5, Madison, CT 06443
• 

  $680,000

  Sold Jul 18, 2025

  76 Horse Pond Rd, Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 3,037 Sq Ft
  • Built 1998

  Last Sold Summary

  • 11% Below List Price
  • $224/SF
  • 27 Days On Market

  Current Estimated Value $741,488

  Last Listing Agent James Didato Berkshire Hathaway NE Prop.

  76 Horse Pond Rd, Madison, CT 06443
• 

  Est $621,642

  Not Listed For Sale

  1197 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft
  • Built 1976

  1197 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 54 Days On Market
• 

  

  /33

  $569,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,022 Sq Ft

  1353 Durham Rd, Madison, CT 06443

  Welcome to 1353 Durham Road in beautiful Madison - a private 2.15-acre interior lot offering peaceful country living with convenient access to Madison's beaches, Chatfield Hollow, and commuter routes. This meticulously maintained raised ranch features 3 bedrooms and 2.5 baths with an open floor plan designed for comfortable everyday living. Hardwood floors flow throughout the home, and the

  Susan Wagner Berkshire Hathaway NE Prop.

  1353 Durham Rd, Madison, CT 06443
• 

  $565,000

  Sold Sep 29, 2025

  531 Green Hill Rd, Madison, CT 06443

  • 3 Beds
  • 1.5 Baths
  • 1,905 Sq Ft
  • Built 1964

  Last Sold Summary

  • 3% Above List Price
  • $297/SF
  • 3 Days On Market

  Current Estimated Value $566,361

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

  531 Green Hill Rd, Madison, CT 06443
• 

  Est $1,362,441

  Not Listed For Sale

  50 Copperfield Dr, Madison, CT 06443

  • 5 Beds
  • 3.5 Baths
  • 4,374 Sq Ft
  • Built 1988

  50 Copperfield Dr, Madison, CT 06443

  Last Sold Summary

  • 22 Days On Market
• 

  

  /40

  $625,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  15 Cornfield Ln, Madison, CT 06443

  Welcome to 15 Cornfield Lane, a charming Colonial style home nestled on a quiet cul-de-sac, offering both privacy and convenience on over 1.5 acres of land. This well-maintained home features a spacious and functional floor plan, perfect for everyday living and entertaining. The main level includes a bright kitchen, formal dining room, and two inviting living spaces, along with a convenient half

  Miranda Micarelli Coldwell Banker Realty

  15 Cornfield Ln, Madison, CT 06443
• 

  $479,000

  Sold Jun 27, 2025

  32 Nutmeg Ln, Madison, CT 06443

  • 4 Beds
  • 1.5 Baths
  • 1,632 Sq Ft
  • Built 1964

  Last Sold Summary

  • $294/SF
  • 24 Days On Market

  Current Estimated Value $519,008

  Last Listing Agent Cathy Lynch Coldwell Banker Realty

  32 Nutmeg Ln, Madison, CT 06443
• 

  Est $1,117,446

  Not Listed For Sale

  5 Michele Ln, Madison, CT 06443

  • 4 Beds
  • 6 Baths
  • 5,220 Sq Ft
  • Built 1987

  5 Michele Ln, Madison, CT 06443

  Last Sold Summary

  • 34 Days On Market

Showing Results 201 - 240, Page 6 of 18