Madison, CT Homes

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  /40

  $2,250,000

  $50K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 3,822 Sq Ft

  101 Garnet Park Rd, Madison, CT 06443

  It's the stillness of the marsh..calm, quiet and ever-changing. This home captures nearly 270 degrees of protected landscape and water views, making the setting feel peaceful, immersive and incredibly rare. Inside, every detail feels thoughtful and intentional. Sunlight pours in and each space was designed to stay connected to the beauty beyond. The main living area rises to an 18-foot cathedral

  Nicole White William Raveis Real Estate

  101 Garnet Park Rd, Madison, CT 06443
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  /33

  $5,250 Per Month

  • 4 Beds
  • 3 Baths
  • 3,495 Sq Ft
  • House for Rent

  16 Shorelands Dr, Madison, CT 06443

  Year-round rental in desirable beach community. This spacious, sunny 4+ bedroom, 3 full bath home has been entirely repainted inside, has had some updates, and kitchen has been upgraded. Large, oversized rooms both upstairs and down. Hardwood floors thoughout the first floor. Basement has new laminate floors. This property has deeded beach rights to one of Madison's loviest sandy beaches, huge

  Alison Gould Gould Group LLC

  16 Shorelands Dr, Madison, CT 06443
• 

  $715,000

  Sold Jun 04, 2026

  96 Winterhill Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,950 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $242/SF
  • 58 Days On Market

  Current Estimated Value $711,830

  Last Listing Agent Bonnie Fillion Berkshire Hathaway NE Prop.

  96 Winterhill Rd, Madison, CT 06443
• 

  Est $1,290,129

  Not Listed For Sale

  217 Devonshire Ln, Madison, CT 06443

  • 4 Beds
  • 6 Baths
  • 5,865 Sq Ft
  • Built 2001

  217 Devonshire Ln, Madison, CT 06443

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Phoebe Schreiner William Pitt Sotheby's Int'l
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  /40

  $875,000

  Pending

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

  23 Aylesbury Cir Unit 23, Madison, CT 06443

  Rare opportunity to own an exceptionally beautiful, turnkey Windermere home overlooking the salt marshes of the Hammonasset River. The 3 BR, 3 bath residence is fully remodeled and upgraded and includes an expansive wrap around stone patio with built-in fire table & entertaining areas. The outside space creates a full outside living room! Views of the marshes are ever-changing from dawn until

  Margaret Muir William Pitt Sotheby's Int'l

  23 Aylesbury Cir Unit 23, Madison, CT 06443
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  /23

  $35,000 Per Month

  • 5 Beds
  • 4.5 Baths
  • 3,697 Sq Ft
  • House for Rent

  19 Middle Beach Rd, Madison, CT 06443

  This beautiful waterfront home has unobstructed views of Long Island Sound.This gorgeous home was built in 2012 with all the bells and whistles. Available for academic rent September 7th 2026 through mid June 2027 at 7K per month. JULY and AUGUST of 2027 is $35,000 PER MONTH. Ask about pets. 5 bedrooms/4 baths, City Water, Natural Gas and Central Air. Lots of parking.

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  19 Middle Beach Rd, Madison, CT 06443
• 

  $2,310,000

  Sold Jul 15, 2026

  36 Cedar Ln, Madison, CT 06443

  • 4 Beds
  • 4 Baths
  • 3,926 Sq Ft
  • Built 1976

  Last Sold Summary

  • 28% Above List Price
  • $588/SF
  • 2 Days On Market

  Current Estimated Value $1,808,675

  Last Listing Agent Rose Ciardiello William Raveis Real Estate

  36 Cedar Ln, Madison, CT 06443
• 

  Est $907,138

  Not Listed For Sale

  23 Blueberry Hill Dr, Madison, CT 06443

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

  23 Blueberry Hill Dr, Madison, CT 06443

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Cortney Emshwiller-Swokla Coldwell Banker Realty
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  /40

  $1,985,000

  Pending

  • 5 Beds
  • 3 Baths
  • 2,920 Sq Ft

  52 E Wharf Rd, Madison, CT 06443

  Welcome to the highly desirable East Wharf area, where this Shingle-Style residence is surrounded by high-value properties. Sited on a generous 3/4-acre lot with a private rear yard and patio, this home offers 2,920 square feet of flexible living space. Step onto the welcoming front porch and into a home designed for comfortable, multi-generational living. The main level is home to a spacious and

  Margaret Muir William Pitt Sotheby's Int'l

  52 E Wharf Rd, Madison, CT 06443
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  /15

  $3,750 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,484 Sq Ft
  • House for Rent

  15 Willard Ave, Madison, CT 06443

  Spend the academic year in this charming Colonial located in the desirable Seaview Beach Association. Begin your mornings with a peaceful stroll along the waterfront, or enjoy an easy walk to the shops, restaurants, and amenities in town. With multiple bedrooms and inviting, open living spaces, this home offers plenty of room to relax, gather, and make lasting memories throughout the academic

  Meig Walz Newcomb Coldwell Banker Realty

  15 Willard Ave, Madison, CT 06443
• 

  $3,775,000

  Sold May 19, 2026

  10 Middle Beach Rd W, Madison, CT 06443

  • 6 Beds
  • 7 Baths
  • 6,074 Sq Ft
  • Built 1986

  Last Sold Summary

  • 10% Below List Price
  • $622/SF
  • 268 Days On Market

  Current Estimated Value $3,672,017

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

  10 Middle Beach Rd W, Madison, CT 06443
• 

  Est $777,215

  Not Listed For Sale

  98 Dorset Ln, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 3,607 Sq Ft
  • Built 1994

  98 Dorset Ln, Madison, CT 06443

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent Antonio Stella eXp Realty
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  /40

  $1,650,000

  Pending

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

  33 River Edge Farms Rd, Madison, CT 06443

  An exceptional home designed for effortless luxury and unforgettable entertaining, where every detail has been thoughtfully imagined, expertly crafted, and beautifully executed. At the heart of the home is an award-winning kitchen that has been featured in multiple publications and earned the 2023 HBRA Parade of Homes Best Kitchen Award. Striking Cambria Southport quartz countertops and a

  Kelly Whiteman William Raveis Real Estate

  33 River Edge Farms Rd, Madison, CT 06443
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  /35

  $9,000 Per Month

  • 7 Beds
  • 7 Baths
  • 5,075 Sq Ft
  • House for Rent

  118 Middle Beach Rd, Madison, CT 06443

  ACADEMIC RENTAL! The iconic, water-front 118 Middle Beach Road is available for rent for the academic year beginning October 1, 2026. This sensational property offers comfortable occupancy for up to fourteen people with 7 bedrooms, 5 full baths, and 2 half baths. The main level is an entertainer's dream featuring an oversized, eat-in kitchen, formal dining area, living room with water views from

  Melanie Abbott William Pitt Sotheby's Int'l

  118 Middle Beach Rd, Madison, CT 06443
• 

  $725,000

  Sold Aug 25, 2025

  23 Paper Mill Dr, Madison, CT 06443

  • 5 Beds
  • 2.5 Baths
  • 2,323 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Above List Price
  • $312/SF
  • 61 Days On Market

  Current Estimated Value $760,474

  Last Listing Agent Dana Weinstein Coldwell Banker Realty

  23 Paper Mill Dr, Madison, CT 06443
• 

  Est $737,540

  Not Listed For Sale

  14 Martleshamheath Ln, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,762 Sq Ft
  • Built 1991

  14 Martleshamheath Ln, Madison, CT 06443

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Karen Martin Century 21 AllPoints Realty
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  /40

  $1,200,000

  • 4 Beds
  • 4 Baths
  • 2,338 Sq Ft

  148 Mungertown Rd, Madison, CT 06443

  Step into a story nearly three centuries in the making. Tucked away on a total of 3 enchanting acres along Connecticut's picturesque shoreline, this extraordinary circa-1752 former Helen Foster Snow homestead is a place where history whispers through every room and timeless beauty meets modern living. Ideally located just minutes from the area's scenic shoreline destinations, including

  Allison Ciarcia William Raveis Real Estate

  148 Mungertown Rd, Madison, CT 06443
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  /23

  $2,900 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,684 Sq Ft
  • House for Rent

  52 Overshores E, Madison, CT 06443

  FURNISHED RENTAL AVAILABLE - September 1, 2026 to May 31, 2027. Comfortable and nicely decorated, this home has 2 bedrooms upstairs that share a newer renovated full bath. This home is located in a private association with access to the Overshores Beach, one of the nicest association beaches on Neck Road. Recently renovated kitchen, newer mud room, newer first floor full bath, laundry room on 1st

  Kirsten Adams William Pitt Sotheby's Int'l

  52 Overshores E, Madison, CT 06443
• 

  $475,000

  Sold Sep 03, 2025

  24 Deepwood Dr, Madison, CT 06443

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1962

  Last Sold Summary

  • 2% Above List Price
  • $396/SF
  • 27 Days On Market

  Current Estimated Value $484,699

  Last Listing Agent Carol Mancini William Pitt Sotheby's Int'l

  24 Deepwood Dr, Madison, CT 06443
• 

  Est $751,959

  Not Listed For Sale

  201 Dorset Ln, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 3,156 Sq Ft
  • Built 1994

  201 Dorset Ln, Madison, CT 06443

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Christina King Connecticut Real Estate Group LLC
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  /2

  $350,000

  $100K PRICE DROP

  • Land
  • 2.05 Acres
  • $170,732 per Acre

  92 Scotland Rd Unit Lot. 3, Madison, CT 06443

  Build your dream home in the upscale shoreline community of Madison CT! Featured in Yankee Magazine as "Best Beach Towns" in Connecticut and not many land opportunities like this. Centrally located this approved lot is a very large 2.05 acre lot that is level, wooded, and private in a well established upscale neighborhood ONLY 1.2 miles from downtown and approximately 2 miles from Hammonasset

  Stacy Bucci Coldwell Banker Realty

  92 Scotland Rd Unit Lot. 3, Madison, CT 06443
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  /38

  $1,200 Per Month

  • 1 Bed
  • 1 Bath
  • 448 Sq Ft
  • House for Rent

  1023 Boston Post Rd, Madison, CT 06443

  *LIST PRICE IS PER WEEK* Inquire about available dates. Are you traveling for business or pleasure or need a temporary place to stay while work is done on your own home? If so, then this cottage - 1 mile from Town and beaches - might be just the ticket! FULLY RENOVATED in 2021, this furnished, open concept cottage combines the living room, kitchen and dining area and has a separate bedroom and

  Irene Keene Coldwell Banker Realty

  1023 Boston Post Rd, Madison, CT 06443
• 

  $900,000

  Sold Jul 30, 2026

  11 Soundview Ave, Madison, CT 06443

  • 2 Beds
  • 1 Bath
  • 1,122 Sq Ft
  • Built 1930

  Last Sold Summary

  • 6% Above List Price
  • $802/SF
  • 48 Days On Market

  Current Estimated Value $835,236

  Last Listing Agent Jessica Hoover William Raveis Real Estate

  11 Soundview Ave, Madison, CT 06443
• 

  Est $737,496

  Not Listed For Sale

  15 Bentwater Ln, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,248 Sq Ft
  • Built 1994

  15 Bentwater Ln, Madison, CT 06443

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Pam Kadamus William Pitt Sotheby's Int'l
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  /39

  $949,000

  $49K PRICE DROP Under Contract

  • 3 Beds
  • 3.5 Baths
  • 3,536 Sq Ft

  10 Isabell Dr, Madison, CT 06443

  Built in 2001, this expansive Custom Cape with its charming front covered porch offers a one-of-a-kind setting in North Madison, ideally located at the end of a cul-de-sac on 2.64 acres and surrounded by open space. The square footage is deceptive with 3536 sf (this DOES NOT include the 3-season room +452 sf) plus the huge basement offering another 1880 sf. Designed with intention and exceptional

  Claudia O'Connell William Raveis Real Estate

  10 Isabell Dr, Madison, CT 06443
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  /24

  $3,300 Per Month

  • 4 Beds
  • 3 Baths
  • 2,065 Sq Ft
  • House for Rent

  33 Grove Ave, Madison, CT 06443

  FULLY FURNISHED ACADEMIC RENTAL. Available from 9/1 - 5/31. Four bedroom colonial just steps from Seaview Beach, a private association beach! Fully furnished, internet is available, TV in 3 rooms. Hardwood floors throughout. Sunroom at back of house, along with a wraparound porch with views of Long Island Sound. Kayak in the photos is available for tenants to use during their stay as well as

  Robert Curry Pearce Real Estate

  33 Grove Ave, Madison, CT 06443
• 

  $1,585,000

  Sold Aug 22, 2025

  61 Governors Way, Madison, CT 06443

  • 4 Beds
  • 5 Baths
  • 6,010 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Above List Price
  • $264/SF
  • 73 Days On Market

  Current Estimated Value $1,676,633

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

  61 Governors Way, Madison, CT 06443
• 

  Est $819,338

  Not Listed For Sale

  67 Devonshire Ln, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 3,726 Sq Ft
  • Built 1997

  67 Devonshire Ln, Madison, CT 06443

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Jessica Kimball William Raveis Real Estate
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  /13

  $349,900

  Coming Soon

  • 2 Beds
  • 1 Bath
  • 625 Sq Ft

  66 Wildcat Rd, Madison, CT 06443

  Nestled in picturesque Madison, Connecticut, this cottage is your private sanctuary, tucked away from the city's hustle and bustle. Enjoy serene surroundings, lush trees, and the beauty of nature. Blissful Outdoor Living: Step outside to savor the fresh country air in your spacious yard. Perfect for gardening, outdoor dining, or lounging in the sun. The loft is a versatile space - use it as a

  Eric Engdall Coldwell Banker Realty

  66 Wildcat Rd, Madison, CT 06443
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  /34

  $5,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,861 Sq Ft
  • House for Rent

  8 Lawson Dr, Madison, CT 06443

  Spend the academic year in this pristine cape right around the corner from East Wharf beach. Walk or ride bikes to the beach, and along the Long Island Sound coastline. Enjoy evenings outside on the spacious patio with stone fire pit, outdoor furniture, dining table, and built-in grilling station. Ride bikes or walk to town and nearby restaurants. Entertain family and guests in the beautifully

  Meig Walz Newcomb Coldwell Banker Realty

  8 Lawson Dr, Madison, CT 06443
• 

  $530,000

  Sold Oct 17, 2025

  9 Madrina Ln, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 2,159 Sq Ft
  • Built 1975

  Last Sold Summary

  • 8% Below List Price
  • $245/SF
  • 83 Days On Market

  Current Estimated Value $558,573

  Last Listing Agent Rose Ciardiello William Raveis Real Estate

  9 Madrina Ln, Madison, CT 06443
• 

  Est $538,879

  Not Listed For Sale

  1928 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft
  • Built 1747

  1928 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Tom Vanacore Century 21 AllPoints Realty
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  /40

  $2,650,000

  Under Contract

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

  24 Indigo Trail, Madison, CT 06443

  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 stream and the preserved stone remnants of a historic mill-an evocative nod to the land's rich past. Inside, the

  Mark McElrath William Pitt Sotheby's Int'l

  24 Indigo Trail, Madison, CT 06443
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  /14

  $7,000 Per Month

  • 2 Beds
  • 1 Bath
  • 608 Sq Ft
  • Apartment for Rent

  165 Middle Beach Rd, Madison, CT 06443

  AVAILABLE FOR THE MONTH OF AUGUST. Live the ultimate shoreline lifestyle on Middle Beach Road, Madison's most prestigious and sought-after coastal street. This delightful 2-bedroom, 1-bathroom garage apartment (on the 2nd floor) offers a rare opportunity to enjoy stunning dual views, capturing the sparkling waters of the Long Island Sound from one side and the serene, ever-changing landscape of

  Kirsten Adams William Pitt Sotheby's Int'l

  165 Middle Beach Rd, Madison, CT 06443
• 

  $475,000

  Sold Sep 05, 2025

  108 Sandlewood Dr, Madison, CT 06443

  • 3 Beds
  • 3 Baths
  • 2,640 Sq Ft
  • Built 1968

  Last Sold Summary

  • 14% Below List Price
  • $180/SF
  • 72 Days On Market

  Current Estimated Value $528,587

  Last Listing Agent Jennifer Bordonaro William Pitt Sotheby's Int'l

  108 Sandlewood Dr, Madison, CT 06443
• 

  Est $616,045

  Not Listed For Sale

  1956 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 1,928 Sq Ft
  • Built 1998

  1956 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Amy Kirst William Pitt Sotheby's Int'l
• 

  

  /22

  $550,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  141 Duck Hole Rd, Madison, CT 06443

  A rare investment opportunity with unmatched storage and garage space! Tucked away on a private 2-acre lot just minutes from I-95 and everything Madison has to offer, this unique property combines immediate rental income with an incredible opportunity for the next owner. The 3-bedroom home is currently tenant-occupied, generating $2,500 per month in rental income, while the expansive detached

  Meig Walz Newcomb Coldwell Banker Realty

  141 Duck Hole Rd, Madison, CT 06443
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  /34

  $12,000 Per Month

  • 3 Beds
  • 3 Baths
  • 2,382 Sq Ft
  • House for Rent

  509 Boston Post Rd, Madison, CT 06443

  Sneak away from the hustle and bustle and spend the month of August at Captain Eber Judd House (circa 1740). This historical gem, reminiscent of Nantucket and Essex Whaling Captain's homes, oozes charm with its stunning wide plank floors, beams, and original fireplaces. Located in the heart of downtown Madison, it's just steps from the gorgeous beach, the quintessential downtown, and the Friday

  Phoebe Schreiner William Pitt Sotheby's Int'l

  509 Boston Post Rd, Madison, CT 06443
• 

  $530,000

  Sold Aug 07, 2026

  101 Sandelwood Dr, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,196 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $241/SF
  • 26 Days On Market

  Last Listing Agent Cathy Lynch Coldwell Banker Realty

  101 Sandelwood Dr, Madison, CT 06443
• 

  Est $793,759

  Not Listed For Sale

  272 County Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,614 Sq Ft
  • Built 2000

  272 County Rd, Madison, CT 06443

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Linda Toscano Coldwell Banker Realty

Showing Results 81 - 120, Page 3 of 18