Madison, CT Homes

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  /22

  $749,000

  • Land
  • 8,276 Sq Ft
  • $3,942,105 per Acre

  885 Boston Post Rd, Madison, CT 06443

  Fully approved and ready to go, this exceptional commercial lot is situated in the heart of vibrant downtown Madison. Boasting approvals for a 5,000 square foot building the property includes a brand-new septic system, 13 designated parking spaces with additional parking options, and unbeatable proximity to restaurants, shopping, the train station, and I-95. Imagine welcoming clients or customers

  Michael Hvizdo Coldwell Banker Realty

  885 Boston Post Rd, Madison, CT 06443
• 

  $725,000 Sold Dec 01, 2025

  129 Acorn Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,698 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $269/SF
  • 103 Days On Market

  Current Estimated Value $749,037

  Last Listing Agent Ann Stewart William Pitt Sotheby's Int'l

  129 Acorn Rd, Madison, CT 06443
• 

  Est $605,552 Not Listed For Sale

  53 Heatherwood Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,129 Sq Ft
  • Built 1977

  53 Heatherwood Dr, Madison, CT 06443

  Last Sold Summary

  • 8% Above List Price
  • $264/SF
  • 33 Days On Market

  • Last Sold Price $561,000
  • Mar 01, 2024

  Last Listing Agent Cathy Lynch Coldwell Banker Realty
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  /2

  $159,900 Under Contract

  • Land
  • 1.43 Acres
  • $111,818 per Acre

  0 Skytop Dr, Madison, CT 06443

  Great opportunity to build in an established neighborhood in the beautiful shoreline community of Madison, CT! Large 1.43 acre rear lot is extremely private and ready for your dream home. Located just a short 1.5mi / 5 minute drive to downtown with easy access to I-95 and a short drive to Hammonasset Beach. Per town will need an updated perc test for final approval. Agent/owner

  Luke Florian SSG Real Estate LLC

  0 Skytop Dr, Madison, CT 06443
• 

  $625,000 Sold Sep 17, 2025

  181 Ridge Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 1,921 Sq Ft
  • Built 1973

  Last Sold Summary

  • 9% Above List Price
  • $325/SF
  • 32 Days On Market

  Current Estimated Value $627,409

  Last Listing Agent Renee Autorino Coldwell Banker Realty

  181 Ridge Rd, Madison, CT 06443
• 

  Est $488,503 Not Listed For Sale

  309 Summer Hill Rd, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Built 1968

  309 Summer Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 18% Above List Price
  • $272/SF
  • 69 Days On Market

  • Last Sold Price $415,000
  • Oct 25, 2024

  Last Listing Agent Allison Bonito William Pitt
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  /35

  $615,000 Coming Soon

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

  15 Hampshire Rd Unit 15, Madison, CT 06443

  One-level living at its best. A pristine two-bedroom residence situated directly across from beautiful Hummer's Pond in one of Madison's most conveniently located communities. Just moments from the beach, town center, and all town amenities, this peaceful home is ideal as a full-time residence or a weekend retreat. Freshly painted throughout, the home features an updated kitchen that opens to the

  Susan Malan William Pitt Sotheby's Int'l

  15 Hampshire Rd Unit 15, Madison, CT 06443
• 

  $693,000 Sold Jun 03, 2025

  68 White Cedar Dr, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,030 Sq Ft
  • Built 1983

  Last Sold Summary

  • 11% Above List Price
  • $341/SF
  • 24 Days On Market

  Current Estimated Value $710,395

  Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty

  68 White Cedar Dr, Madison, CT 06443
• 

  Est $589,415 Not Listed For Sale

  307 Summer Hill Rd, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 3,261 Sq Ft
  • Built 1980

  307 Summer Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 7% Above List Price
  • $169/SF
  • 34 Days On Market

  • Last Sold Price $550,000
  • Jun 05, 2024

  Last Listing Agent Jennifer Trautman Turton William Pitt
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  /40

  $1,699,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,661 Sq Ft

  7 Linden Ln, Madison, CT 06443

  Beautiful waterfront post-and-beam home offering breathtaking views of the tidal marsh, osprey nest, and beyond. Set on a peaceful corner lot along a quiet one-way lane, this property borders conservation land and is just a short walk to East Wharf Beach. The open-concept living and dining areas are filled with natural light and designed to capture the scenery, with large windows and direct

  Heather Smith Our Home Realty Advisors

  7 Linden Ln, Madison, CT 06443
• 

  $415,000 Sold Sep 26, 2025

  15D Yankee Glen Rd Unit 15D, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 1,434 Sq Ft
  • Built 1979

  Last Sold Summary

  • 10% Above List Price
  • $289/SF
  • 16 Days On Market

  Current Estimated Value $459,948

  Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC

  15D Yankee Glen Rd Unit 15D, Madison, CT 06443
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  Est $551,586 Not Listed For Sale

  1065 Durham Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 1,764 Sq Ft
  • Built 1973

  1065 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 10% Above List Price
  • $285/SF
  • 17 Days On Market

  • Last Sold Price $503,000
  • Oct 11, 2023

  Last Listing Agent Donald Schilder Houlihan Lawrence WD
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  /9

  $1,235,000

  • Land
  • 1.02 Acres
  • $1,210,784 per Acre

  8 Old Route 79, Madison, CT 06443

  Great commercial lot - signalize corner, level and cleared. A rare opportunity for Developers and Investors. Located at the strategic Junction of Old route 79 and Durham Road . One minute to I-95. The property boasts exceptional visibility an accessibility from both north and southbound traffic. Short distance to downtown MADISON, this site is ideal for a variety of commercial ventures, including

  Thomas Simjian Keller Williams Coastal

  8 Old Route 79, Madison, CT 06443
• 

  $530,000 Sold Jul 15, 2025

  49 Wilshire Rd, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 1,879 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Below List Price
  • $282/SF
  • 126 Days On Market

  Current Estimated Value $532,456

  Last Listing Agent Doris Fallon William Raveis Real Estate

  49 Wilshire Rd, Madison, CT 06443
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  Est $525,434 Not Listed For Sale

  32 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 2 Baths
  • 1,877 Sq Ft
  • Built 1985

  32 Legend Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 4% Below List Price
  • $290/SF
  • 28 Days On Market

  • Last Sold Price $545,000
  • Feb 28, 2025

  Last Listing Agent Jane Cardarelli William Raveis Real Estate
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  /36

  $549,000 Under Contract

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

  6 Sandgate Cir, Madison, CT 06443

  Welcome to Windemere East. Located in Madison Ct this condo offers ranch style living with open floor plan. Hardwood floors throughout the unit. Unit offers 1,476 sq feet of living space. Two Bedrooms and 2 full bathrooms having primary with roll in en-suite. Sunroom with ever changing views of the Hammonasset River. A short drive to Hammonasset State Park and downtown Madison. Main Street offer

  Paula Stuart Berkshire Hathaway NE Prop.

  6 Sandgate Cir, Madison, CT 06443
• 

  $550,000 Sold Jun 12, 2025

  46 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 2 Baths
  • 1,374 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $400/SF
  • 18 Days On Market

  Current Estimated Value $572,924

  Last Listing Agent Meg Farmer RE/MAX Heritage

  46 Legend Hill Rd, Madison, CT 06443
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  Est $634,742 Not Listed For Sale

  263 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1987

  263 Legend Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 4% Below List Price
  • $264/SF
  • 15 Days On Market

  • Last Sold Price $660,000
  • Apr 22, 2024

  Last Listing Agent Jennifer Trautman Turton William Pitt
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  /40

  $2,195,000

  • 5 Beds
  • 3 Baths
  • 3,172 Sq Ft

  15 Highland Terrace, Madison, CT 06443

  COME SEE THIS ONE OF KIND FULLY RENOVATED MADISON HOME WITH PRIVATE BEACH RIGHTS!!! Just 300 feet from the sand, this home was once a traditional raised ranch and now has been brilliantly redesigned into a spacious 'elevated ranch' with an open-concept floor plan that feels airy, bright, and made for entertaining! Step into coastal luxury with this fully reimagined Madison home, where every

  John Cronin Century 21 AllPoints Realty

  15 Highland Terrace, Madison, CT 06443
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  $1,600,000 Sold May 12, 2025

  31 Governors Way, Madison, CT 06443

  • 5 Beds
  • 5 Baths
  • 4,350 Sq Ft
  • Built 2006

  Last Sold Summary

  • 7% Above List Price
  • $368/SF
  • 40 Days On Market

  Current Estimated Value $1,674,706

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

  31 Governors Way, Madison, CT 06443
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  Est $548,722 Not Listed For Sale

  279 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 4 Baths
  • 2,476 Sq Ft
  • Built 1985

  279 Legend Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 8% Above List Price
  • $204/SF
  • 81 Days On Market

  • Last Sold Price $506,000
  • Apr 15, 2024

  Last Listing Agent Margaret Muir William Pitt
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  /38

  $4,000,000

  • 5 Beds
  • 6 Baths
  • 5,657 Sq Ft

  45 Island Ave, Madison, CT 06443

  Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight

  Meig Walz Newcomb Coldwell Banker Realty

  45 Island Ave, Madison, CT 06443
• 

  $2,500,000 Sold Apr 24, 2026

  0 River Rd, Madison, CT 06443

  • Land
  • 5.56 Acres
  • $449,640 per Acre

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Todd Gould William Pitt Sotheby's Int'l

  0 River Rd, Madison, CT 06443
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  Est $551,897 Not Listed For Sale

  75 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 3 Baths
  • 2,140 Sq Ft
  • Built 1985

  75 Legend Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 10% Above List Price
  • $234/SF
  • 3 Days On Market

  • Last Sold Price $500,000
  • Oct 03, 2023

  Last Listing Agent Laurie Mazzeo William Pitt
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  /39

  $1,195,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,587 Sq Ft

  21 Evarts Ln Unit 21, Madison, CT 06443

  The beloved Mews - This in town luxury townhouse condominium will not disappoint. Quality built, you can enjoy the quiet or take advantage of everything the vibrant downtown area has to offer, including theatre, restaurants & a world class bookstore. On the ground level, relax in an attractive & private bluestone patio area, just off the expansive eat in kitchen. If entertaining is your passion,

  Margaret Muir William Pitt Sotheby's Int'l

  21 Evarts Ln Unit 21, Madison, CT 06443
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  $1,200,000 Sold Oct 09, 2025

  110 E Wharf Rd, Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 1930

  Last Sold Summary

  • 7% Below List Price
  • $759/SF
  • 11 Days On Market

  Current Estimated Value $1,245,291

  Last Listing Agent Lisa Daniele William Raveis Real Estate

  110 E Wharf Rd, Madison, CT 06443
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  Est $553,557 Not Listed For Sale

  22 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • Built 1984

  22 Legend Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 11% Above List Price
  • $257/SF
  • 2 Days On Market

  • Last Sold Price $500,000
  • Aug 08, 2023

  Last Listing Agent Laurie Mazzeo William Pitt
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  /39

  $545,000

  • 2 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  23 Hampshire Rd Unit 23, Madison, CT 06443

  Welcome to Kensington North, a highly desirable condo community in the heart of Madison. This well-located unit offers a wonderful opportunity to create your ideal home in a sought-after setting. The main level features a spacious living and dining area, perfect for everyday living and entertaining. The eat-in kitchen offers great potential with sliders to the sunroom and patio as well as being

  Laurie Mazzeo William Pitt Sotheby's Int'l

  23 Hampshire Rd Unit 23, Madison, CT 06443
• 

  $705,000 Sold Aug 22, 2025

  310 Opening Hill Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,424 Sq Ft
  • Built 1968

  Last Sold Summary

  • 1% Above List Price
  • $291/SF
  • 5 Days On Market

  Current Estimated Value $720,363

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

  310 Opening Hill Rd, Madison, CT 06443
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  Est $493,588 Not Listed For Sale

  105 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 1,676 Sq Ft
  • Built 1985

  105 Legend Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 23% Above List Price
  • $239/SF
  • 47 Days On Market

  • Last Sold Price $400,000
  • Oct 31, 2024

  Last Listing Agent Bonnie Fillion Berkshire Hathaway Home Services
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  /12

  $325,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  42 Wildcat Rd, Madison, CT 06443

  Ranch-style single-family home situated on 1 acre, just 5 minutes from Hammonasset State Beach. The property features classic New England stone walls surrounding much of the land, along with a detached two-car garage. Inside, has nice looking exposed beams! Then living room, kitchen, three bedrooms, and one bathroom-all on the main floor. Full unfinished basement with an exterior hatch. The

  Ethan Maddalena Berkshire Hathaway NE Prop.

  42 Wildcat Rd, Madison, CT 06443
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  $185,000 Sold Feb 02, 2026

  983 Boston Post Rd, Madison, CT 06443

  • Land
  • 2.87 Acres
  • $64,460 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 959 Days On Market

  Current Estimated Value $189,361

  Last Listing Agent Jennifer Gurnell William Raveis Real Estate

  983 Boston Post Rd, Madison, CT 06443
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  Est $597,035 Not Listed For Sale

  1086 Durham Rd, Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 1,977 Sq Ft
  • Built 1789

  1086 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 4% Above List Price
  • $291/SF
  • 26 Days On Market

  • Last Sold Price $575,000
  • Apr 17, 2025

  Last Listing Agent Kimberly O'Donnell William Raveis Real Estate
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  /33

  $645,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,352 Sq Ft

  79 Acorn Rd, Madison, CT 06443

  Bike to town from this pristine Colonial, ideally set on a level lot with over an acre of beautifully manicured grounds. This meticulously maintained 3-bedroom home offers natural gas, public water, and generous living space for today's lifestyle. Enjoy a spacious front-to-back living room, a cozy family room with a gas fireplace, and a sun-filled three-season porch featuring vaulted ceilings and

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  79 Acorn Rd, Madison, CT 06443
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  $878,000 Sold Jun 27, 2025

  38 Skytop Dr, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,204 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Above List Price
  • $398/SF
  • 25 Days On Market

  Current Estimated Value $889,849

  Last Listing Agent Luke Florian SSG Real Estate LLC

  38 Skytop Dr, Madison, CT 06443
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  Est $546,192 Not Listed For Sale

  39 Beechwood Dr, Madison, CT 06443

  • 3 Beds
  • 1.5 Baths
  • 1,768 Sq Ft
  • Built 1962

  39 Beechwood Dr, Madison, CT 06443

  Last Sold Summary

  • 27% Above List Price
  • $243/SF
  • 3 Days On Market

  • Last Sold Price $430,000
  • Jun 02, 2023

  Last Listing Agent Jane Cardarelli William Raveis Real Estate
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  /36

  $499,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,688 Sq Ft

  660 Opening Hill Rd, Madison, CT 06443

  Rare Investment opportunity in Madison under 10 minutes to charming downtown and Madison Beach! Own a freshly painted 3-bedroom home plus a separate accessory apartment over a 3-car garage attached by a breezeway, all set on level 2.57 private acres. Live in one and rent the other-or maximize income by renting both. This setup is also ideal for multi-generational living. The 1,048 main ranch home

  Allison Hughes William Raveis Real Estate

  660 Opening Hill Rd, Madison, CT 06443
• 

  $665,000 Sold Nov 14, 2025

  18 Kelsey Place, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1960

  Last Sold Summary

  • $528/SF
  • 44 Days On Market

  Current Estimated Value $667,349

  Last Listing Agent Betsy Anderson William Pitt Sotheby's Int'l

  18 Kelsey Place, Madison, CT 06443
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  Est $1,240,527 Not Listed For Sale

  90 Joshua Trail, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 3,879 Sq Ft
  • Built 1986

  90 Joshua Trail, Madison, CT 06443

  Last Sold Summary

  • 14% Above List Price
  • $280/SF
  • 46 Days On Market

  • Last Sold Price $1,085,000
  • Sep 07, 2023

  Last Listing Agent Bob Yostos Coldwell Banker Realty
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  /40

  $2,475,000

  • 4 Beds
  • 3.5 Baths
  • 3,697 Sq Ft

  880 Boston Post Rd, Madison, CT 06443

  The historic c. 1904 Scranton Homestead, described as a Colonial Revival gem, is coming to the market! This much admired 3700 sf in town landmark offers an estate feel on a large, beautifully landscaped lot providing both privacy and convenience, moments from the village center and East Wharf Beach. With four bedrooms, this residence borrows from classic forms, with window styles, columns and

  Margaret Muir William Pitt Sotheby's Int'l

  880 Boston Post Rd, Madison, CT 06443

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