Madison, CT Homes

• 

  $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 $688,921

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

  30 Church Ln, Madison, CT 06443
• 

  Est $584,387 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

  • 89% Above List Price
  • $102/SF
  • 3 Days On Market

  • Last Sold Price $310,000
  • Mar 15, 2024

  Last Listing Agent Lauren Freedman Coldwell Banker Realty
• 

  

  

  /38

  $2,875,000

  • 5 Beds
  • 5.5 Baths
  • 7,139 Sq Ft

  37 Lantern Hill Rd, Madison, CT 06443

  An unbeatable location, 37 Lantern Hill is set in one of Madison's most desirable in-town neighborhoods. Close to sandy beaches, charming town center and the Madison Country Club, recreation and everyday conveniences are right at your doorstep. Traditional by design with ten foot ceilings, abundant natural light and generously scaled rooms that create an airy feel, ideal for relaxing or

  Margaret Muir William Pitt Sotheby's Int'l

  37 Lantern Hill 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 $498,391

  Last Listing Agent Remi Tremblay William Raveis Real Estate

  24 Railroad Ave, Madison, CT 06443
• 

  Est $594,061 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

  • 3% Above List Price
  • $233/SF
  • 35 Days On Market

  • Last Sold Price $577,500
  • Sep 27, 2024

  Last Listing Agent Sheila Tinn-Murphy Berkshire Hathaway Home Services
• 

  

  /27

  $625,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,073 Sq Ft

  370 Opening Hill Rd, Madison, CT 06443

  This charming, meticulously maintained 3-bedroom, 2.5-bath home offers exceptional quality and pride of ownership throughout. Features include central air and a walk-out basement that backs up to beautiful open space, providing both privacy and scenic views. While some finishes reflect a classic style, the home is in outstanding condition-spotlessly clean and truly move-in ready. Beneath the

  Meig Walz Newcomb Coldwell Banker Realty

  370 Opening Hill 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 $1,272,685

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

  41 Allison Dr, Madison, CT 06443
• 

  Est $522,608 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

  • 3% Below List Price
  • $289/SF
  • 28 Days On Market

  • Last Sold Price $540,000
  • Aug 09, 2024

  Last Listing Agent Samantha Celentano Coldwell Banker Realty
• 

  

  /22

  $339,600 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,692 Sq Ft

  2304 Durham Rd, Madison, CT 06443

  ***All interested parties must qualify pursuant to CT General Statutes, Deed Restrictions, and Income Limits. Eligible Gross Household Income for household is: *$88,792 1person,*$101,476-2 people, *$14,161-3 people, *$126,845-4people & for more request full list. ***Nature Lovers take note! Well maintained updated home located directly across from Madison's "Rockland Preserve" in the Twin Pine

  Diane Beckwith Popolizio William Raveis Real Estate

  2304 Durham 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 $267,247

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

  268 Durham Rd, Madison, CT 06443
• 

  Est $1,000,185 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

  • 6% Above List Price
  • $315/SF
  • 1 Day On Market

  • Last Sold Price $947,000
  • Jul 21, 2023

  Last Listing Agent Julie Bedell Compass Connecticut, LLC
• 

  

  /39

  $799,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,568 Sq Ft

  114 Rolling Meadow Rd, Madison, CT 06443

  Beautiful 5 bedroom, 3.5 bath Colonial set in a highly desirable neighborhood just minutes from town, schools, and the beach. Situated on a level, 1+ acre lot, this home offers an expansive backyard ideal for outdoor entertaining and everyday fun. Hardwood floors run throughout the home, enhancing its classic appeal. The spacious kitchen is thoughtfully designed and features a SubZero

  Susan Clifford Coldwell Banker Realty

  114 Rolling Meadow Rd, 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 $880,357

  Last Listing Agent Kayla Chasse Compass Connecticut, LLC

  198 Green Hill Rd, Madison, CT 06443
• 

  Est $770,177 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

  • 3% Above List Price
  • $244/SF
  • 46 Days On Market

  • Last Sold Price $750,000
  • Mar 04, 2025

  Last Listing Agent Kirsten Adams William Pitt
• 

  

  /28

  $589,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,849 Sq Ft

  12 Rustic Ln, Madison, CT 06443

  Nestled on a picturesque 1.94 acre lot in the desirable shoreline community of Madison, 12 Rustic Lane offers the perfect blend of comfort, style, and move in ready convenience. Framed by a stunning stone wall, this beautifully renovated home welcomes you with a bright, open floor plan. The home features 4 spacious bedrooms and 2 beautifully renovated bathrooms, thoughtfully updated with new

  Natalie Zoef Vanguard Private Client Grp

  12 Rustic Ln, 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 $587,901

  Last Listing Agent Dana Weinstein Coldwell Banker Realty

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

  Est $806,270 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

  • 2% Below List Price
  • $302/SF
  • 22 Days On Market

  • Last Sold Price $820,000
  • Oct 16, 2024

  Last Listing Agent Dana Weinstein Coldwell Banker Realty
• 

  

  /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
• 

  $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 $834,239

  Last Listing Agent Leigh Whiteman William Raveis Real Estate

  27 Hammonassett Meadows Rd, Madison, CT 06443
• 

  Est $1,653,777 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

  • 3% Above List Price
  • $320/SF
  • 263 Days On Market

  • Last Sold Price $1,600,000
  • Jun 28, 2024

  Last Listing Agent Margaret Muir William Pitt
• 

  

  /31

  $575,000 Coming Soon

  • 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
• 

  $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 $922,584 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

  • $207/SF
  • 76 Days On Market

  • Last Sold Price $920,000
  • Aug 29, 2024

  Last Listing Agent Linda Toscano Coldwell Banker Realty
• 

  

  /19

  $149,900

  • 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
• 

  $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 $468,900

  Last Listing Agent Emily Lovejoy William Raveis Real Estate

  22 Centre Village Dr, Madison, CT 06443
• 

  Est $711,197 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

  • 16% Above List Price
  • $217/SF
  • 131 Days On Market

  • Last Sold Price $615,000
  • Jan 05, 2024

  Last Listing Agent Stephanie Jacobs Sunset Creek Realty, LLC
• 

  

  /30

  $769,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,108 Sq Ft

  104 Scotland Rd, Madison, CT 06443

  Set on what is arguably the most beautiful lot in downtown Madison. This enchanting 5-bedroom farmhouse perfectly blends timeless charm with modern convenience. The nearly one-acre, meticulously manicured property makes a lasting impression. Complete with majestic stone walls & a stunning brick patio. Inside, the home welcomes you with a thoughtfully designed mudroom, creating a private and

  Susan Santoro William Pitt Sotheby's Int'l

  104 Scotland 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 $630,513

  Last Listing Agent Lauren Freedman Coldwell Banker Realty

  81 Bartlett Dr, Madison, CT 06443
• 

  Est $941,740 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

  • 11% Above List Price
  • $245/SF
  • 3 Days On Market

  • Last Sold Price $850,000
  • Jun 29, 2023

  Last Listing Agent Sue Woods William Pitt
• 

  

  /40

  $1,675,000

  • 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
• 

  $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 $741,077

  Last Listing Agent James Didato Berkshire Hathaway NE Prop.

  76 Horse Pond Rd, Madison, CT 06443
• 

  Est $995,801 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

  • 11% Above List Price
  • $176/SF
  • 80 Days On Market

  • Last Sold Price $900,000
  • Feb 20, 2024

  Last Listing Agent Toni Iandoli William Pitt
• 

  

  /39

  $2,750,000 Coming Soon

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

  81A Middle Beach Rd, Madison, CT 06443

  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 equipped

  Margaret Muir William Pitt Sotheby's Int'l

  81A Middle Beach 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 $574,524

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

  531 Green Hill Rd, Madison, CT 06443
• 

  Est $608,791 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

  • 2% Above List Price
  • $398/SF
  • 54 Days On Market

  • Last Sold Price $595,000
  • Mar 25, 2024

  Last Listing Agent Debra Pardales William Pitt
• 

  

  /25

  $1,950,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,574 Sq Ft

  24 Ridgewood Ave, Madison, CT 06443

  Perched high above the flood plains, this pristine coastal retreat captures sweeping views of the Neck River as it opens into the Long Island Sound. Thoughtfully designed to embrace its stunning setting, the home's open floor plan is filled with natural light and seamless indoor-outdoor flow. At the heart of the home, a chef-inspired kitchen blends beauty and function-perfectly for entertaining

  Meig Walz Newcomb Coldwell Banker Realty

  24 Ridgewood Ave, Madison, CT 06443
• 

  $850,000 Sold May 16, 2025

  23 Blueberry Hill Dr, Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 3,692 Sq Ft
  • Built 2001

  Last Sold Summary

  • $230/SF
  • 61 Days On Market

  Current Estimated Value $888,146

  Last Listing Agent Cortney Emshwiller-Swokla Coldwell Banker Realty

  23 Blueberry Hill Dr, Madison, CT 06443
• 

  Est $1,374,645 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

  • 2% Above List Price
  • $309/SF
  • 22 Days On Market

  • Last Sold Price $1,350,000
  • Aug 30, 2024

  Last Listing Agent Pam Kadamus William Pitt
• 

  

  /40

  $625,000

  • 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 $511,936

  Last Listing Agent Cathy Lynch Coldwell Banker Realty

  32 Nutmeg Ln, Madison, CT 06443

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