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Homes for Sale in 06443

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  • /34

    $825,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,665 Sq Ft

    51 Country Way, Madison, CT 06443

    Tucked away in a serene, private setting surrounded by scenic trails and protected conservation land, this exceptional home showcases a sophisticated designer aesthetic, where timeless New England character meets thoughtfully curated modern living. Classic stone walls, refined finishes, and beautifully appointed spaces create a residence that feels both elegant and effortlessly welcoming. At the

    Melanie Scull William Pitt Sotheby's Int'l

    51 Country Way, Madison, CT 06443
  • /29

    $1,299,000

    Open Sun 1PM - 4PM
    • 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
  • /29

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 2,024 Sq Ft

    53 Summer Hill Rd, Madison, CT 06443

    Wake up to pure tranquility in this stunning 4-bedroom, 2.5-bath contemporary home. Perfectly positioned across from the Hammonasset River, the setting is nothing short of amazing-complete with mature trees, bird song, and beautiful multi-tiered stone landscaping. Boasting modern lines and an incredible connection to its natural surroundings, this home offers a private retreat like no other.

    Pam Kadamus William Pitt Sotheby's Int'l

    53 Summer Hill Rd, Madison, CT 06443
  • /28

    $639,000

    Open Sat 10AM - 1PM Coming Soon
    • 4 Beds
    • 2 Baths
    • 2,137 Sq Ft

    94 Warpas Rd, Madison, CT 06443

    Welcome to 94 Warpas Road, a carefully maintained Cape-style home on a picturesque 1-acre lot in one of Madison's most desirable locations. This 4-bedroom home blends classic New England charm with modern updates. Situated directly across from protected land trust property with hiking trails, you'll enjoy peaceful views and the assurance that no homes will ever be built across the street. The

    Abbey Nakano Houlihan Lawrence WD

    94 Warpas Rd, Madison, CT 06443
  • /39

    $789,000

    Open Sat 1PM - 3PM Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,647 Sq Ft

    89 Summer Hill Rd, Madison, CT 06443

    Set on a beautiful, private 1.25-acre lot in one of Madison's sought-after neighborhoods, this spacious, well maintained Colonial offers exceptional flexibility and comfort with nine rooms plus an additional sunroom. The kitchen is updated with granite countertops and newer appliances. Bathrooms have all been updated with tile and granite. The floors are hardwood throughout the home. Thoughtfully

    Susan Wagner Berkshire Hathaway NE Prop.

    89 Summer Hill Rd, Madison, CT 06443
  • /40

    $650,000

    • 4 Beds
    • 2.5 Baths
    • 2,057 Sq Ft

    476 Summer Hill Rd, Madison, CT 06443

    This turnkey, sun-filled Colonial situated south of Route 80 in Madison perfectly blends meticulous maintenance with smart, modern updates. The gracious main level features elegant French doors opening to a bright living room, a generous formal dining room- a perfect place for family gatherings and a cozy family room centered around a classic wood-burning fireplace. The heart of the home is the

    Amy Kirst William Pitt Sotheby's Int'l

    476 Summer Hill Rd, Madison, CT 06443
  • /30

    $485,900

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

    34 Canborne Way, Madison, CT 06443

    Nestled quietly at the rear of the Windemere Complex, this freestanding ranch-style unit delivers seamless, one-level living in a highly desirable location. Minutes from Hammonasset State Park, Madison's charming town center, and pristine town beaches, this home perfectly balances convenience and tranquility. Inside, newly installed flooring stretches across an inviting open floor plan. The

    Amy Kirst William Pitt Sotheby's Int'l

    34 Canborne Way, Madison, CT 06443
  • /40

    $1,300,000

    • 5 Beds
    • 2.5 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,

    Agent Photo

    Cathy Lynch

    Coldwell Banker Realty

    (475) 252-4751

    77 Silo Hill, 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
  • /27

    $850,000

    Open Fri 3PM - 5PM
    • 2 Beds
    • 1 Bath
    • 852 Sq Ft

    17 Linden Ln, Madison, CT 06443

    Coastal Paradise in the Heart of Madison! Welcome to one of Madison's most desirable shoreline beach communities, where coastal charm, breathtaking views, and endless outdoor recreation come together to create the perfect seaside retreat. This delightful cottage offers spectacular views of Fence Creek Salt Marsh and a glimpse of Long Island Sound. Kayak or paddleboard from the beach one block

    Lisa Aranci Berkshire Hathaway NE Prop.

    17 Linden Ln, Madison, CT 06443
  • /40

    $935,000

    • 4 Beds
    • 3.5 Baths
    • 4,250 Sq Ft

    86 Nursery Ln, Madison, CT 06443

    ABSOLUTELY STUNNING is the only way to describe this immaculate 4+ bedroom Colonial, perfectly situated in one of Madison's most desirable and convenient neighborhoods. From the moment you step inside, the incredible sunlit, open-concept floor plan captivates you. Designed for effortless entertaining & everyday living. The spacious living room that features a cozy gas fireplace flows seamlessly

    Alicia Mahon William Pitt Sotheby's Int'l

    86 Nursery Ln, Madison, CT 06443
  • /36

    $1,325,000

    • 3 Beds
    • 2.5 Baths
    • 1,293 Sq Ft

    97 E Wharf Rd, Madison, CT 06443

    If you've ever strolled down East Wharf, you've likely noticed this charming home. Just a few houses from the beach, this thoughtfully renovated 3 bedroom, 2.5 bath gem blends timeless coastal Connecticut style with custom craftsmanship and modern convenience. The curb appeal is undeniable, with a pristinely manicured yard, paver driveway and Belgian block apron. Inside, the living room features

    Phoebe Schreiner William Pitt Sotheby's Int'l

    97 E Wharf Rd, Madison, CT 06443
  • /37

    $605,000

    • 2 Beds
    • 3 Baths
    • 2,135 Sq Ft

    5 Thelbridge St Unit 5, Madison, CT 06443

    One person's loss is another one's gain! You have a second chance to make this this lovely property yours. It is more than a home --it's a lifestyle. Tucked into one of Madison's most sought-after communities at Windermere East, you'll feel at home the moment you enter the front door. The bright, open floor plan provides casual, coastline living at its best. The remodeled kitchen with granite

    Joanne Breen ERA Hart Sargis-Breen

    5 Thelbridge St Unit 5, 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
  • /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
  • /40

    $998,000

    • 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
  • /35

    $2,650,000

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

    24 Indigo Trail, Madison, CT 06443

    Luxury Property Auction: 11-25 June. Current High Bid: $1,300,000. Estimated Sale Price: $2,200,000 - $2,800,000. 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

    Lee Leslie Concierge Auctions, LLC

    24 Indigo Trail, Madison, CT 06443
  • /40

    $1,899,900

    • 4 Beds
    • 2.5 Baths
    • 2,957 Sq Ft

    99 Garnet Park Rd, Madison, CT 06443

    Stunning waterfront home with water views on both sides, offering a rare coastal setting in an upscale neighborhood surrounded by multimillion-dollar properties. Enjoy breathtaking views from the rear of the home and expansive backyard, along with shared waterfront access across the street where a kayak or small boat may be launched at high tide. Designed with flexibility in mind, this home

    Heather Smith Our Home Realty Advisors

    99 Garnet Park Rd, 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
  • /26

    $200,000

    • 2 Beds
    • 1 Bath
    • 480 Sq Ft

    50 East St, Madison, CT 06443

    LOCATION ~ LOCATION ~ It matters !! Situated in the Coastal Charm of Madison, this Seasonal Cottage is your Escape you can plan on Every Summer !! Enjoy all that Madison has to offer w/ Concert's on the Green, Farmers Markets, Restaurants and Beaches. It's a Long Summer too ~ Residence can stay from April 1st all the way through October 31st., a Full 7-Months. Home is perfectly set at the End of

    Tom Clancy William Pitt Sotheby's Int'l

    50 East St, Madison, CT 06443
  • /39

    $2,495,000

    Open Sat 2PM - 4PM $255K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,321 Sq Ft

    81A Middle Beach Rd, Madison, CT 06443

    NEW PRICE. 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

    Margaret Muir William Pitt Sotheby's Int'l

    81A Middle Beach Rd, Madison, CT 06443
  • /31

    $460,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 2 Baths
    • 1,865 Sq Ft

    10 Salem Rd, Madison, CT 06443

    Welcome to this well-maintained home offering a flexible layout and thoughtful updates throughout. Step into a welcoming foyer that opens into a bright living room filled with natural light from multiple windows. From here, the layout flows seamlessly into the dining area, where a partial wall creates separation while maintaining an open, airy feel. Just beyond, the kitchen has been tastefully

    Leigh Whiteman William Raveis Real Estate

    10 Salem Rd, Madison, CT 06443
  • /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

    Agent Photo

    Cathy Lynch

    Coldwell Banker Realty

    (475) 244-1665

    30 Meeting House Ln, Madison, CT 06443
  • /40

    $2,295,000

    $180K PRICE DROP
    • 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, has come 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
  • /40

    $1,399,000

    $276K PRICE DROP
    • 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
  • /20

    $164,900

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 592 Sq Ft

    32 North St, Madison, CT 06443

    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 not forget the new floors in

    Melanie Abbott William Pitt Sotheby's Int'l

    32 North St, Madison, CT 06443
  • /40

    $2,800,000

    • 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
  • /40

    $2,300,000

    • 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
  • /18

    $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
  • /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
  • /40

    $164,900

    • 1 Bed
    • 1 Bath
    • 441 Sq Ft

    7 3rd St, Madison, CT 06443

    Tucked away like a hidden jewel at the shoreline, this storybook beach cottage captures the charm of coastal living.Approached by a classic brick landing, this cottage welcomes you with beachy curb appeal and a sense of relaxed living. Bathed in natural light and thoughtfully updated, this delightful retreat offers a warm and inviting interior designed for effortless living. Every detail reflects

    Karen Bruno Roos Williams Real Estate

    7 3rd St, Madison, CT 06443
  • /38

    $3,750,000

    $250K 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
  • /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
  • /27

    $499,000

    $41K 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

    $154,000

    Open Sat 11AM - 1PM
    • 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
  • /35

    $225,000

    $24K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 647 Sq Ft

    26 North St, Madison, CT 06443

    Experience the best of shoreline living in Madison, just about a mile from the sandy beaches of Hammonasset. This charming seasonal cottage offers a bright, airy feel with vaulted wood-beamed ceilings and natural light throughout-perfect for easy summer living by the water. With 647 square feet, the home includes two bedrooms (one ideal as a den or flex space), a sun-filled kitchen with stone

    Karen Floriano William Raveis Real Estate

    26 North St, Madison, CT 06443
  • /5

    $900,000

    • Land
    • 2.42 Acres
    • $371,901 per Acre

    0 Mill Rd, Madison, CT 06443

    A RARE & VERSATILE REAL ESTATE OPPORTUNITY! For a limited time, discover this truly unique 2.42 acre corner parcel that perfectly balances natural beauty with massive investment potential. Featuring a picturesque mix of mature trees & diverse topography, the land offers a slight, wooded hill on one end (ideal for an elevated, private homesite) and a sweeping flat open area on the other. A classic

    Todd Gould William Pitt Sotheby's Int'l

    0 Mill Rd, Madison, CT 06443
  • /33

    $595,000

    • 2 Beds
    • 2 Baths
    • 2,560 Sq Ft

    10 Runnymede Ln, Madison, CT 06443

    Nestled in the highly sought-after Windermere East community, this rare free-standing condo offers the perfect blend of privacy, comfort, and coastal charm in beautiful Madison. Enjoy serene river views and a peaceful setting just moments from the shoreline. This well-maintained home features 2 bedrooms and 2 full baths, a spacious fireplaced living room, and a bright kitchen ideal for everyday

    Laura Cariati William Raveis Real Estate

    10 Runnymede Ln, Madison, CT 06443

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