8,661

Madison, CT Homes

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  • 4 Boston Post Rd, Madison, CT 06443
    4 Boston Post Rd, Madison, CT 06443
    4 Boston Post Rd, Madison, CT 06443
    /31

    $850,000

    $250K PRICE DROP
    • Land
    • 3.67 Acres
    • $231,608 per Acre

    4 Boston Post Rd, Madison, CT 06443

    Rarely does a Legacy Property, with a "Shovel-Ready" vision, arrive with the hardest yards of coastal development already complete. East River Landing is a fully de-risked, 3.67-acre asset at the Madison/Guilford gateway, combining an extensive marina income opportunity with unprecedented residential scalability. Approved Maritime Asset. Forget proposed plans-this is a fully built, 46-slip marina

    Michael Barnes Silver and Oak Realty

    4 Boston Post Rd, Madison, CT 06443
  • 11 Middle Beach Rd, Madison, CT 06443

    $1,825,000

    Sold Jun 01, 2026

    11 Middle Beach Rd, Madison, CT 06443

    • 3 Beds
    • 3 Baths
    • 1,976 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Above List Price
    • $924/SF
    • 2 Days On Market

    Current Estimated Value $3,808,638

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

    11 Middle Beach Rd, Madison, CT 06443
  • 85 Garnet Park Rd, Madison, CT 06443
    85 Garnet Park Rd, Madison, CT 06443
    85 Garnet Park Rd, Madison, CT 06443
    /40

    $2,800,000

    Pending
    • 4 Beds
    • 6 Baths
    • 4,854 Sq Ft

    85 Garnet Park Rd, Madison, CT 06443

    A home that captures you-and doesn't let go. Nestled along the quiet edge of the Neck River, this is one of those rare offerings where design, setting and detail immediately leave an impression. From the moment you arrive, the front porch sets the tone for what unfolds beyond it. Inside, every space feels considered. A true designer's home where nothing is overlooked and nothing is left to

    Nicole White William Raveis Real Estate

    85 Garnet Park Rd, Madison, CT 06443
  • 43 Fort Path Rd, Madison, CT 06443

    $503,000

    Sold Jan 30, 2026

    43 Fort Path Rd, Madison, CT 06443

    • 3 Beds
    • 1.5 Baths
    • 1,346 Sq Ft
    • Built 1960

    Last Sold Summary

    • 7% Below List Price
    • $374/SF
    • 40 Days On Market

    Current Estimated Value $513,909

    Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC

    43 Fort Path Rd, Madison, CT 06443
  • 17 Yankee Glen Rd Unit 17-D, Madison, CT 06443
    17 Yankee Glen Rd Unit 17-D, Madison, CT 06443
    17 Yankee Glen Rd Unit 17-D, Madison, CT 06443
    /12

    $475,000

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

    17 Yankee Glen Rd Unit 17-D, Madison, CT 06443

    MOVE IN READY! Welcome home to 17 Yankee Glen Drive, a beautifully maintained and thoughtfully updated free standing townhouse nestled in the highly desirable Madison Center neighborhood. Spanning 1,434 square feet of bright, inviting living space, this 2-bedroom, 2.5-bathroom gem is the perfect blend of coastal charm and modern convenience. Step inside to a spacious, open-concept main level

    Steven Koleno Beycome of Connecticut

    17 Yankee Glen Rd Unit 17-D, Madison, CT 06443
  • 129 Acorn 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 $739,692

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

    129 Acorn Rd, Madison, CT 06443
  • 15 Cambridge Dr, Madison, CT 06443
    15 Cambridge Dr, Madison, CT 06443
    15 Cambridge Dr, Madison, CT 06443
    /34

    $1,125,000

    $25K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,208 Sq Ft

    15 Cambridge Dr, Madison, CT 06443

    Nestled in one of Madison's most desirable communities (off Island Ave), this exceptional residence offers upscale downsizing at its finest - just a 5-minute stroll to the Madison Town Green or a 10-minute walk to the beach. Thoughtfully redesigned, upgraded and meticulously maintained, the home combines elegant architectural details with modern comfort and convenience. The custom remodeled

    Meig Walz Newcomb Coldwell Banker Realty

    15 Cambridge Dr, Madison, CT 06443
  • 40 Hull Rd, Madison, CT 06443

    $825,000

    Sold May 14, 2026

    40 Hull Rd, Madison, CT 06443

    • 4 Beds
    • 3 Baths
    • 3,462 Sq Ft
    • Built 1963

    Last Sold Summary

    • $238/SF
    • 62 Days On Market

    Current Estimated Value $817,669

    Last Listing Agent Sue Woods William Pitt Sotheby's Int'l

    40 Hull Rd, Madison, CT 06443
  • 26 Bassett Ln, Madison, CT 06443
    26 Bassett Ln, Madison, CT 06443
    26 Bassett Ln, Madison, CT 06443
    /40

    $2,149,000

    $101K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,160 Sq Ft

    26 Bassett Ln, Madison, CT 06443

    Completely rebuilt and expanded in 2026, this custom coastal home with deeded beach rights is located in Madison's charming Seafields Association. Thoughtfully designed with designer details throughout, the home provides elevated shoreline living with glimpses of Long Island Sound, state-of-the-art appliances, high-end finishes, a bright, open layout, mudroom, butler's pantry with laundry, and a

    Steven Koleno Beycome of Connecticut

    26 Bassett Ln, Madison, CT 06443
  • 181 Ridge Rd, 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 $620,679

    Last Listing Agent Renee Autorino Coldwell Banker Realty

    181 Ridge Rd, Madison, CT 06443
  • 885 Boston Post Rd, Madison, CT 06443
    885 Boston Post Rd, Madison, CT 06443
    885 Boston Post Rd, Madison, CT 06443
    /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
  • 15D Yankee Glen Rd Unit 15D, 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 $466,588

    Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC

    15D Yankee Glen Rd Unit 15D, Madison, CT 06443
  • 221 Duck Hole Rd, Madison, CT 06443
    221 Duck Hole Rd, Madison, CT 06443
    221 Duck Hole Rd, Madison, CT 06443
    /37

    $565,000

    Pending
    • 3 Beds
    • 3 Baths
    • 2,068 Sq Ft

    221 Duck Hole Rd, Madison, CT 06443

    **PLEASE SUBMIT ANY OFFERS BY 12PM TUESDAY 6/16** Nestled in a serene woodland setting, this charming raised ranch offers the perfect blend of classic shoreline character and modern upgrades throughout over 2,000 square feet of finished living space. The home immediately impresses with its warm cedar shingle exterior and brick facade, gorgeously framing a home that is as sturdy as it is stylish.

    Bailey Mannix Sunset Creek Realty, LLC

    221 Duck Hole Rd, Madison, CT 06443
  • 49 Wilshire Rd, 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 $570,810

    Last Listing Agent Doris Fallon William Raveis Real Estate

    49 Wilshire Rd, Madison, CT 06443
  • 0 Skytop Dr, Madison, CT 06443
    0 Skytop Dr, Madison, CT 06443
    /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
  • 0 River Rd, 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
  • 28 Downing Way Unit 28, Madison, CT 06443
    28 Downing Way Unit 28, Madison, CT 06443
    28 Downing Way Unit 28, Madison, CT 06443
    /33

    $595,000

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

    28 Downing Way Unit 28, Madison, CT 06443

    Nicely updated 1476 sf condo with family room, plus sunporch and full basement. Largest style at Windermere. Living room and dining room are open and have nice hardwood floors. Newer kitchen with maple cabinetry. Cozy family room with fireplace opens to a 3 season porch. Off the sunporch is a private patio. There are 2 good sized bedrooms and 2 lovely newer baths. There is an attic and a detached

    Judy Libby Berkshire Hathaway NE Prop.

    28 Downing Way Unit 28, Madison, CT 06443
  • 110 E Wharf Rd, Madison, CT 06443

    $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 $1,250,579

    Last Listing Agent Lisa Daniele William Raveis Real Estate

    110 E Wharf Rd, Madison, CT 06443
  • 15 Hampshire Rd Unit 15, Madison, CT 06443
    15 Hampshire Rd Unit 15, Madison, CT 06443
    15 Hampshire Rd Unit 15, Madison, CT 06443
    /35

    $615,000

    Pending
    • 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
  • 310 Opening Hill Rd, 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 $725,672

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

    310 Opening Hill Rd, Madison, CT 06443
  • 153 Middle Beach Rd, Madison, CT 06443
    153 Middle Beach Rd, Madison, CT 06443
    153 Middle Beach Rd, Madison, CT 06443
    /40

    $2,150,000

    • 4 Beds
    • 2 Baths
    • 2,251 Sq Ft

    153 Middle Beach Rd, Madison, CT 06443

    Rare opportunity to own a Nantucket-style coastal retreat on coveted Middle Beach Road in Madison. Just moments from East Wharf Beach and downtown, this distinctive property offers timeless shoreline charm, a huge porch, breathtaking tidal marsh views, and glimpses of Long Island Sound from the second floor. Filled with character and reminiscent of a 1920s seaside cottage, the sun-filled main

    Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

    153 Middle Beach Rd, Madison, CT 06443
  • 983 Boston Post Rd, Madison, CT 06443

    $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 $190,015

    Last Listing Agent Jennifer Gurnell William Raveis Real Estate

    983 Boston Post Rd, Madison, CT 06443
  • 7 Pent Rd, Madison, CT 06443
    7 Pent Rd, Madison, CT 06443
    7 Pent Rd, Madison, CT 06443
    /39

    $775,000

    $25K PRICE DROP Pending
    • 2 Beds
    • 1.5 Baths
    • 1,142 Sq Ft

    7 Pent Rd, Madison, CT 06443

    Discover a hidden treasure in one of Madison's finest neighborhoods, featuring vintage bungalow charm. A bright and welcoming sun room, enhanced with baseboard heating, offers a serene space to relax in every season. The main floor includes a large combined living and dining room with stunning wood floors and a wood burning fireplace. Off of the bright and functional kitchen you will find a full

    Julie Ovian William Pitt Sotheby's Int'l

    7 Pent Rd, Madison, CT 06443
  • 38 Skytop Dr, Madison, CT 06443

    $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 $887,140

    Last Listing Agent Luke Florian SSG Real Estate LLC

    38 Skytop Dr, Madison, CT 06443
  • 8 Old Route 79, Madison, CT 06443
    8 Old Route 79, Madison, CT 06443
    8 Old Route 79, Madison, CT 06443
    /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
  • 12 Rustic Ln, Madison, CT 06443

    $300,000

    Sold Oct 30, 2025

    12 Rustic Ln, Madison, CT 06443

    • 4 Beds
    • 1.5 Baths
    • 1,912 Sq Ft
    • Built 1971

    Last Sold Summary

    • 6% Below List Price
    • $157/SF
    • 4 Days On Market

    Current Estimated Value $564,189

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

    12 Rustic Ln, Madison, CT 06443
  • 15 Highland Terrace, Madison, CT 06443
    15 Highland Terrace, Madison, CT 06443
    15 Highland Terrace, Madison, CT 06443
    /40

    $2,195,000

    Open Sat 1PM - 4PM
    • 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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