Newest Homes for Sale in Madison, CT

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  /33

  $524,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  35 Aileen Dr, Madison, CT 06443

  First Time Offered In 25 Years. This contemporary raised ranch, set on 2.36 secluded acres, is located in a quiet cul-de-sac neighborhood just minutes to town. The living room with hardwood floors features a cathedral ceiling with beams, a wood burning fireplace, floor to ceiling windows with double sliders to a deck with built in bench, perfect for morning coffee or evening enjoyment. The

  Leslie Richo William Raveis Real Estate

  35 Aileen Dr, Madison, CT 06443
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  /40

  $4,499,000

  Coming Soon

  • 6 Beds
  • 6.5 Baths
  • 5,817 Sq Ft

  14 Middle Beach Rd W, Madison, CT 06443

  A rare opportunity at one of Madison's most storied shoreline addresses. Set back from the water on a lush, professionally landscaped acre, this sophisticated four-level residence offers resort-like living with deeded private beach rights directly across the street, a distinctive touch on the Connecticut shoreline. Nearly 6,000 square feet of impeccably designed living space unfolds across six

  Tara Hawley Coldwell Banker Realty

  14 Middle Beach Rd W, Madison, CT 06443
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  /7

  $350,000

  • 4 Beds
  • 2.5 Baths
  • 2,004 Sq Ft

  22 Pine Ridge Dr, Madison, CT 06443

  Super opportunity to buy a home in Madison at a reasonable price! Needs work but well worth the effort. Owner suspects mold may be present in the basement but has received quotes for remediation and contents have been removed. The attached release and indemnification form must be signed prior to access being granted. This is a very rare and special property just waiting for you to make your own!

  Rick Allen William Raveis Real Estate

  22 Pine Ridge Dr, Madison, CT 06443
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  /40

  $1,700,000

  Coming Soon

  • 3 Beds
  • 3 Baths
  • 2,674 Sq Ft

  50 Webster Point Rd, Madison, CT 06443

  AN exceptional BEACH HOME in an UNBEATABLE LOCATION! Situated in a highly desirable beach neighborhood south of Route 1, this exquisite home is completely move-in ready with no work needed and talk about location. In one direction you have a short distance to TWO beaches AND in the other, The Shoreline Greenway Trail into Hamonnasset State Park with it's 2 miles stretch of sandy beach. Inside

  Todd Gould William Pitt Sotheby's Int'l

  50 Webster Point Rd, Madison, CT 06443
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  /40

  $561,000

  • 3 Beds
  • 1 Bath
  • 1,023 Sq Ft

  1466 Durham Rd, Madison, CT 06443

  Privately tucked away on 4.13 acres, this well maintained log cabin sanctuary offers a rare blend of serene homestead living and investment potential in a premier shoreline community. An inviting covered porch welcomes you into a updated interior highlighted by a cathedral ceiling, wide-plank flooring, a cozy fireplace, and a remodeled kitchen equipped with quartz countertops, seamlessly

  Julia King William Raveis Real Estate

  1466 Durham Rd, Madison, CT 06443
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  /10

  $900,000

  • Land
  • 1.24 Acres
  • $725,806 per Acre

  78 Lantern Hill Rd, Madison, CT 06443

  Build Your Dream Home on Prestigious Lantern Hill Road Discover an exceptional opportunity to own a 1.2acre parcel tucked away on one of Madison's most coveted and private culdesacs. Located at 78 Lantern Hill Road, this hidden gem offers the perfect balance of tranquility and convenience-less than a mile from Madison's beautiful beaches, vibrant town center, boutique shopping, dining, golf, and

  Tom Clancy William Pitt Sotheby's Int'l

  78 Lantern Hill Rd, Madison, CT 06443
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  /24

  $500,000

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

  22 Thelbridge St Unit 22, Madison, CT 06443

  Step out of the 3 season, enclosed porch to the private park-like grounds of this ranch-style condo in Windermere East. This home has been tenderly cared for and is ready to welcome its next owners to enjoy. The main living areas offers a nice open floor plan, combining the living and dining areas. Both bedrooms are large enough to accommodate a king-size bed or two twin beds. There are two full

  Doris Fallon William Raveis Real Estate

  22 Thelbridge St Unit 22, Madison, CT 06443
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  /38

  $3,000,000

  • 4 Beds
  • 6 Baths
  • 4,833 Sq Ft

  17 Barberry Ln, Madison, CT 06443

  RARE OPPORTUNITY in the highly sought-after Barberry Farms Association! With only 2 MLS sales since 2021, homes in this premier beach community seldom become available. Enjoy private access to a wonderfully wide & deep sandy beach that has storage bins & an area for kayaks & small sailboats to make life easier. BIG home, BIG rooms. Spanning 4,833 sq ft, this 10 room Colonial features hardwood

  Todd Gould William Pitt Sotheby's Int'l

  17 Barberry Ln, Madison, CT 06443
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  /28

  $210,000

  $25K PRICE DROP

  • 1 Bed
  • 0.5 Baths
  • 732 Sq Ft

  40 East St, Madison, CT 06443

  Enjoy the best the shoreline has to offer in this charming seasonal summer cottage. Bring your swimsuits, sunscreen, and a book... and move right into this furnished, turnkey summer house. One of the largest cottages, this home has central air, 2-3 parking spaces, and a lovely lot. Sun-filled, airy, and spacious, with a large kitchen and dining room, a generous living room, and 2 additional

  Marissa McCue William Pitt Sotheby's Int'l

  40 East St, Madison, CT 06443
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  /15

  $260,000

  • 1 Bed
  • 1 Bath
  • 806 Sq Ft

  10 Brantwood Dr Unit 10, Madison, CT 06443

  Ideal ground floor one-bedroom end unit in desirable Brantwood. Eat-in kitchen with sliders leading to an oversized private patio space ideal for out-door living. New refrigerator and dishwasher being installed this week. Newer thermal windows, carpeting, and vinyl flooring, ac wall unit, baseboard heat, hot water heater, custom window treatments and full sized Speed Queen washer/dryer, all in

  Bette Zollshan William Pitt Sotheby's Int'l

  10 Brantwood Dr Unit 10, Madison, CT 06443
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  /35

  $569,000

  $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,944 Sq Ft

  25 Samantha Ln, Madison, CT 06443

  Nicely maintained 3-bedroom, 3-full-bath home nestled in a quaint cul-de-sac setting. The home is in very good condition and offers comfortable living space both inside and out. The spacious kitchen features granite countertops, plenty of cabinet space, and a center island-perfect for everyday living and entertaining. Primary Bedroom has its own private full bath. Living Room-Dining combination

  Dee Hasuly KW Legacy Partners

  25 Samantha Ln, Madison, CT 06443
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  /13

  $349,900

  • 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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  /13

  $450,000

  $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,592 Sq Ft

  27 Pine Ridge Dr, Madison, CT 06443

  Opportunity to make sweat equity, this home needs work. Kitchen, living room, dining room, 4 bedrooms, 2 baths, 2 car garage make up this expanded ranch on a lovely level lot on cul-de-sac. The dining room could be a second family room. Open flow for entertaining. Just minutes to downtown Madison and beaches. Top schools. Owner is not in position to make repairs. Perfect home to update to your

  Judy Libby Berkshire Hathaway NE Prop.

  27 Pine Ridge Dr, Madison, CT 06443
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  /27

  $450,000

  $20K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,296 Sq Ft

  12 W Sussex Place Unit 12, Madison, CT 06443

  Welcome to effortless, low-maintenance living in this beautifully maintained 2-bedroom, 1.5-bath condominium, built in 2006. Offering 1,296 square feet of thoughtfully designed living space, plus approximately 608 square feet of finished lower-level space, this home provides exceptional flexibility for today's lifestyle. The bright, open floor plan features hardwood floors, a spacious kitchen

  Mark McElrath William Pitt Sotheby's Int'l

  12 W Sussex Place Unit 12, Madison, CT 06443
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  /34

  $335,000

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 764 Sq Ft

  89 Cottage Rd, Madison, CT 06443

  Highly sought after and rarely available-until now! 89-2 Cottage Road is the seasonal Madison cottage you'll want to run toward. Proudly part of the historic Little Colony community settled by veterans just after World War II, this lovely abode offers two bedrooms and a thoughtfully renovated full bath. The heart of the home is a generous, open-concept living space featuring a beautifully updated

  Melanie Abbott William Pitt Sotheby's Int'l

  89 Cottage Rd, Madison, CT 06443
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  /39

  $2,190,000

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

  15 Highland Terrace, Madison, CT 06443

  COME EXPERIENCE THIS ONE-OF-A-KIND, FULLY RENOVATED MADISON HOME ON A RARE DOUBLE LOT WITH PRIVATE BEACH RIGHTS! Just 300 feet from the sandy shoreline, this exceptional home has been completely reimagined from a traditional raised ranch into a stunning elevated ranch with a bright, open-concept floor plan designed for modern living and effortless entertaining. Every detail has been thoughtfully

  John Cronin Century 21 AllPoints Realty

  15 Highland Terrace, Madison, CT 06443
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  /23

  $1,750,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,913 Sq Ft

  262 Mungertown Rd, Madison, CT 06443

  Build your custom dream home in South Madison! Welcome to this incredible opportunity in a prime location! Set on a level, treed, 2.32-acre lot on the hidden, more secluded end of Mungertown Road, offering PRIVACY and GREAT CONVENIENCE. Just THREE MILES to town and beaches, ONE MILE to Hand and Polson schools, and .25 MILES to the state-of-the-art Neck River Elementary, opened in 2025. Enjoy

  Lisa Rollins Team Compass Connecticut, LLC

  262 Mungertown Rd, Madison, CT 06443
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  /24

  $565,000

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

  29 Wilshire Rd Unit 29, Madison, CT 06443

  Experience true WIDE OPEN SPACES in highly sought-after Kensington Acres South! With condos, it is all about LOCATION. This desirable completely detached standalone Ranch is not attached along the corners like some other units. Flooded w/ bright natural light, the home boasts peaceful, expansive lawn views from your private enclosed Sun Room, a perfect spot for morning coffee. A flat, level &

  Todd Gould William Pitt Sotheby's Int'l

  29 Wilshire Rd Unit 29, Madison, CT 06443
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  /39

  $925,000

  • 3 Beds
  • 3.5 Baths
  • 3,734 Sq Ft

  3 Longview Terrace, Madison, CT 06443

  Set on a peaceful cul-de-sac in Madison's highly desirable Strathmore Farms community, 3 Longview Terrace is an exceptional stand-alone condominium home that captures the essence of luxurious coastal living. This thoughtful 3-bedroom Colonial seamlessly blends elegance and comfort, offering a flowing first-floor layout that includes a formal dining room, a living room, an eat-in kitchen that

  

  Betsy Anderson

  William Pitt Sotheby's Int'l

  3 Longview Terrace, Madison, CT 06443
• 

  

  /40

  $574,000

  $5K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  250 Legend Hill Rd, Madison, CT 06443

  Welcome to 250 Legend Hill Road, a beautifully maintained townhouse condominium in Madison's sought-after Legend Hill community with a tennis/pickleball courts, a Gunite pool, and a clubhouse housed in the original cobblestone mansion. This particular home is positioned to capture both morning and afternoon light, and distant views of Long Island Sound. Inside, the first floor features a gracious

  Kelly Whiteman William Raveis Real Estate

  250 Legend Hill Rd, Madison, CT 06443
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  /40

  $635,000

  $30K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,604 Sq Ft

  81 Legend Hill Rd Unit 81, Madison, CT 06443

  Rarely available, this unit is the largest size Townhouse ("Model D") at Legend Hill. It benefits from a quiet location in the complex away from the main road. This unit has been well maintained with excellent natural light and updated neutral decor. Since purchasing, these owners have installed all new flooring throughout first level, in addition to new carpets on second level. Also recently

  Carol Mancini William Pitt Sotheby's Int'l

  81 Legend Hill Rd Unit 81, Madison, CT 06443
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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
• 

  

  /20

  $500,000

  Open Mon 11AM - 2PM $37K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,236 Sq Ft

  371 Race Hill Rd, Madison, CT 06443

  This home is located in the desirable shoreline town of Madison! Nestled on a peaceful 1.12-acre lot, this charming 3-bedroom, 1.5-bath ranch offers the perfect blend of privacy, comfort, and opportunity. Step inside to find a functional, light-filled layout designed for easy one-level living. The spacious living area flows into the kitchen and dining space, creating an inviting atmosphere for

  Tanisha Bundy Fathom Realty CT LLC

  371 Race Hill Rd, Madison, CT 06443
• 

  

  /40

  $564,900

  Open Sat 11AM - 1PM

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

  6 Essex Ln, Madison, CT 06443

  Welcome home to 6 Essex Lane! Elegant and inviting, this meticulously maintained ranch style condo is set in a quiet corner of Kensington Acres North. With a beautiful back patio, you can relax in a peaceful oasis, surrounded by nature. Inside, the expansive living room flows into the dining room, all with lots of light. The gracious kitchen offers quality cabinetry and a granite countertop

  Lisa Edgerton William Raveis Real Estate

  6 Essex Ln, Madison, CT 06443
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  /38

  $1,200,000

  • 5 Beds
  • 5.5 Baths
  • 3,832 Sq Ft

  1209 Durham Rd, Madison, CT 06443

  Private.Pastoral.Purposeful. Available for the first time in decades. This rare 4-acre compound offers a Farmhouse style home, a guest house, 3-car garage with additional storage, and attached in-home gym, office equipped with bathroom, and artist's studio. This legacy property delivers both on location and acreage offering a one-of-a-kind sequestered compound that simply cannot be replicated.

  Heather Clinton Berkshire Hathaway NE Prop.

  1209 Durham Rd, Madison, CT 06443
• 

  

  /40

  $875,000

  • 2 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 2 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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  /40

  $1,378,800

  • 3 Beds
  • 2.5 Baths
  • 2,767 Sq Ft

  1308 Durham Rd, Madison, CT 06443

  Originally built in 1825, this residence has been thoughtfully updated to preserve its historic essence while incorporating modern conveniences. Nestled on a generous 4.38-acre lot, this extraordinary home boasts 3 spacious bedrooms and 2.5 beautifully appointed bathrooms within its expansive 3,500 square feet of living space. As you step inside, you'll be captivated by the elegant oak hardwood

  

  Nick Prevost

  William Raveis Real Estate

  1308 Durham Rd, Madison, CT 06443
• 

  

  /29

  $1,299,000

  • 3 Beds
  • 3 Baths
  • 1,188 Sq Ft

  32 Liberty St, Madison, CT 06443

  Rare coastal compound opportunity in Madison's highly desirable Seaview Beach area. Situated on approximately one-half acre just moments from the shoreline, this unique property features a main residence and a newer detached accessory dwelling unit, offering flexibility rarely found in one of Connecticut's premier shoreline communities. The main home is clean, functional, and ready for a new

  Karina Ukhnitska Real Broker CT, LLC

  32 Liberty St, Madison, CT 06443
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  /38

  $880,000

  $70K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,795 Sq Ft

  2415 Durham Rd, Madison, CT 06443

  Turn down a long, picturesque driveway to a stunning mid-century cape, unseen from the roadway. Note, the spectacular fieldstone chimney on the large addition of the gable-end plus the closed in screened porch to the west. Ahead you'll find a large, detached 2-car garage and off to the south a small barn with great potential for an equestrian opportunity. From the screened in porch, enter the

  Debra Thomas Sette Real Estate LLC

  2415 Durham Rd, Madison, CT 06443
• 

  

  /40

  $1,300,000

  • 5 Beds
  • 3.5 Baths
  • 4,783 Sq Ft

  77 Silo Hill, Madison, CT 06443

  Welcome to this fabulous one-owner custom home in sought-after Neck River Farms. A gracious, spacious foyer warmly welcomes you inside, setting the tone for the beautifully maintained interior filled with abundant natural light. A dedicated home office with elegant French doors offers the perfect space for working remotely or quiet study. The inviting living room is ideal for entertaining,

  

  Cathy Lynch

  Coldwell Banker Realty

  77 Silo Hill, Madison, CT 06443
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  /40

  $1,950,000

  $300K 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
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  /38

  $1,695,000

  • 5 Beds
  • 3.5 Baths
  • 3,912 Sq Ft

  30 Meeting House Ln, Madison, CT 06443

  Historic gem on the Madison Village Green. Once known as "Hartsbourne," this storied Madison residence is celebrated for its premier location overlooking the town green and its timeless architectural presence. A true local landmark, the home is distinguished by its striking curved eaved roofline, reminiscent of a pagoda with a unique flat seamed copper roof center. Beautifully aligned with the

  

  Cathy Lynch

  Coldwell Banker Realty

  30 Meeting House Ln, Madison, CT 06443
• 

  

  /20

  $149,900

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 592 Sq Ft

  32 North St, Madison, CT 06443

  With a new roof in process, 32 North Street is calling you home! Set on one of the largest lots in Dud's Village, this lovely cottage is the idyllic seasonal abode. Equipped with 2 bedrooms, 1 full bath, and an outdoor shower, you will surely enjoy your summers along the Madison shoreline here. The recently refreshed kitchen and fresh coat of paint throughout will undoubtedly delight. And let's

  Melanie Abbott William Pitt Sotheby's Int'l

  32 North St, Madison, CT 06443
• 

  

  /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
• 

  

  /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
• 

  

  /38

  $3,495,000

  $505K PRICE DROP

  • 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
• 

  

  /33

  $1,975,000

  • 4 Beds
  • 2 Baths
  • 3,882 Sq Ft

  441 Opening Hill Rd, Madison, CT 06443

  Updated 4 bedroom 2 Full bath Cape on 15+ Acres of rolling Meadows and woods bordering State Forest and over 800 feet of frontage on Opening Hill. Extensive updating includes new windows and doors, original wide-board refinishing in the original building. A new kitchen in the cathedral ceilinged family room addition with deck that commands beautiful views of two spring fed, stocked ponds below

  Steve Adkins Berkshire Hathaway NE Prop.

  441 Opening Hill Rd, Madison, CT 06443
• 

  

  /27

  $455,000

  $85K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft

  6 Ladshaw Dr, Madison, CT 06443

  Privacy & convenience are both found within this updated detached stand-alone Ranch home in sought after Kensington Acres. Enjoy this 'tucked away' home yet a short walk to historic downtown Madison with its famed bookstore, shopping, restaurants & retail stores. This home has been beautifully maintained and shows pride of ownership throughout. Enjoy single floor living in your 2 bedroom, 2 bath

  Greg robbins Houlihan Lawrence WD

  6 Ladshaw Dr, Madison, CT 06443
• 

  

  /25

  $138,000

  $16K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 476 Sq Ft

  16 North St, Madison, CT 06443

  Escape to the Connecticut shoreline with this beautifully maintained seasonal cottage in Dud's Village in Madison-the perfect summer retreat just minutes from the beach. Located less than one mile from Hammonasset Beach State Park, Connecticut's largest shoreline park, this charming getaway offers effortless access to two miles of sandy beaches, scenic walking and biking trails, and endless

  Tricia Farin Real Broker CT, LLC

  16 North St, 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

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