luxury properties with pool for sale Madison, United States

A true once in a lifetime opportunity! As you wind through picturesque Sachem's Head onto Walden Hill Road, a circular driveway will lead you to an unparalleled waterview estate on almost two acres. The coastal home sits above Long Island Sound on one of the highest points in Sachem's Head and spans 5,185 square feet. The main level features walls of windows that provide unforgettable views of Long Island Sound and Faulkner's Island. The open kitchen/family room will satisfy any gourmet chef. It's a perfect space for indoor entertaining where guests can enjoy a crackling fire or step outside to an incredible bluestone patio with a fire pit for cool evening bonfires. Take in the 270 degree view of the Sound and enjoy both the sunrise and sunset. Outside entertaining is easy with a heated Pebble Tech Gunite pool, sound system, an outdoor shower, and ocean breezes. The coveted Sachem's Head Association offers amenities that include: beach access, tennis and paddle courts (approx. 600 ft from the house), kayak rack, boat launch, and possible deep water mooring. This coastal home has public water, a whole house generator, an irrigation system, security, and surveillance system, an Invisible Fence, the potential to subdivide, newer septic system (2010), an oversized 2 car garage, and no need for flood insurance. Nothing Compares.

Discover 9 Sunset Ridge Drive, an elegant colonial residence constructed in 2015 and updated throughout 2024-2025. From the grand foyer with detailed millwork to the bright, open layout, every inch of this home has been meticulously refined. The stunning kitchen anchors the home with marble countertops, stainless steel appliances, a gas cooktop, and a spacious pantry-flowing effortlessly into the inviting living room with a gas fireplace, window seating, and sliders to the backyard, as well as the dramatic family room with vaulted ceilings and Palladian windows. A formal dining room, private office, laundry room, and powder room complete the main level. Upstairs, four spacious bedrooms offer comfort and flexibility, highlighted by a serene primary suite featuring a brand-new custom closet system and a luxurious bathroom with a double marble vanity and shower. The recent updates truly set this property apart, including refinished hardwood floors, fresh paint, stylish new light fixtures, a newly completed great room above the garage, refreshed bathrooms with modern fixtures and accents, and a fully finished garage with insulation and refinished floors. The exterior has been transformed into a private oasis with an in-ground pool, professional landscaping, full PVC fencing, a new stone patio, and a freshly installed driveway. Set on a quiet cul-de-sac just minutes from commuter routes and the town green, this move-in-ready home delivers the perfect blend of style and value.

Where gardens flourish and privacy surrounds you, this Moose Hill retreat offers a lifestyle rooted in beauty, nature, and quiet sophistication. Light-filled interior features oversized and bow windows, Hardie cement siding, and Marvin windows throughout. Extraordinary gardens showcase three-season blooms, perennial herbs, berry plantings, fruit trees, irrigation, and a fenced vegetable garden with raised beds. For the green thumb, lower-level grow lights extend the gardening season for early planting. Chef's kitchen with Caesarstone countertops, Wolf appliances, Sub-Zero refrigeration, and built-in dining. Separate family room addition designed as a destination space with wet bar, propane fireplace, and dramatic floor-to-ceiling stone chimney. French doors open to outdoor living areas. Brazilian Tigerwood decking, three-season porch, pool with diving board, and built-in Wolf grill center-ideal for entertaining in a private natural setting with distant skyline views. Primary suite with heated floors and Jacuzzi tub, finished lower-level recreation space, three-bay garage, solar system, and whole-house Generac generator.

Two hours from New York City. Two hours from Boston. A world away from both. Privacy is the ultimate luxury. This masterfully re-imagined 5,234 sq. ft. compound located in historic Ivoryton, a village within the town of Essex, sits behind newly established hedges on nearly two flat, manicured acres - completely turn-key, completely private. The grounds are designed for outdoor living. A 20 X 40 gunite pool flows into a hydrangea-framed landscape. Three bluestone patios for entertaining, dining, and quiet retreat. A newly built two-car garage, wired with new electrical and EV charger-ready. Inside, the transformation is total. A chef's kitchen built around a custom black cherry island with Sub-Zero refrigerator, new double wall oven, and cooktop. A butler's pantry adds a second refrigerator and dedicated wine fridge. Four bedrooms with private en suite bathrooms, including a reimagined primary suite with spa-level finishes. Two home offices. And the sunroom - a fully restored 1920s porch with original terra cotta floors and sweeping estate views. Every room is professionally curated with bespoke wallcoverings and custom light fixtures. Steps from the Ivoryton Playhouse, The Copper Beech, and Prive Swiss. Minutes to Connecticut River marinas. Long Island Sound 15 minutes beyond. A truly unique property located in what Yankee Magazine ranks as the #1 small town in New England.

Experience the perfect blend of timeless character and contemporary convenience in this stunning colonial. The residence welcomes you with an open-concept floor plan and an expertly updated chef's kitchen, featuring premium Sub-Zero refrigeration for an upscale culinary experience. Designed for both relaxation and entertaining, the home offers four bedrooms and three full baths, including a cozy family room ideal for intimate gatherings. The upper level is anchored by a generous primary suite, complete with a private home office and expansive closets accented with stylish barn doors. The lifestyle continues outdoors in a private, fenced-in backyard oasis featuring a pool, a cabana and lush green space. The town center, schools, library and beaches are just a walk from this gorgeous home offering a pleasant walkable lifestyle. At 24 Cottage Place, you can enjoy the soul of the past with every modern creature comfort at your fingertips. Disclaimer: Field card states 3 bedrooms but there are 4 bedrooms in this home.

Introducing The Marsh House...a remarkable waterfront Village estate that incorporates a Main residence, sited at 1 Neck Road...originally a sheep barn constructed entirely of stone in 1912, and subsequently renovated with stunning architectural detail including massive floor to ceiling, multi-paned arched windows, beautiful slate roofing and lush, professionally landscaped grounds punctuated by mature gardens and specimen trees, a tennis court and sparkling pool surrounded by naturalistic plantings. Each room of this incredible residence has its own personality, both formal and informal, incorporating soaring ceilings and filled with natural light. Across the generous lower motor court, the unique and charming Boathouse serves as separate guest quarters, complete with a fully updated kitchen, Great Room and upper level bedroom and bath. The third residence C1900, designated as 3 Neck Road and appropriately called the Gate House, is a two bedroom home, sited on its own .96 acre parcel of land with separate access, perfect as additional guest or caretaker quarters. There is also the potential for a separate building lot set away from the Main house. All structures merge seamlessly on the expansive 14.6 acre property that fronts directly on the Lieutenant River...and incredibly all this in the heart of Old Lyme Village. Simply irresistible!

Orient – Set high above the Long Island Sound in the storied enclave known as The Hill, this rare offering captures the essence of classic Orient living. Authentic, timeless, and grand in scale, the home showcases architectural details including five fireplaces, elegant 16-over-1 windows, and a front entry framed by original sidelights. The 1.3-acre grounds unfold across rolling terrain with mature landscaping, stonework, and meandering garden paths. A sparkling swimming pool sits tucked into the landscape, creating a private retreat. Inside, generous rooms and a waterside screened porch invite gatherings large and small, all set against the backdrop of unforgettable sunsets. The home offers space, character, and endless potential. Cherished by the same family for 65 years, it now awaits its next steward. Properties of this caliber and in this location are exceedingly rare. It doesn’t get more quintessentially North Fork than this. A truly special Orient opportunity.

This 4-bedroom Colonial offers the perfect combination of space, comfort & location. Ideally situated in a subdivision close to shopping, restaurants and major highways. The main level welcomes you with a spacious eat-in kitchen featuring abundant cabinetry, perfect for cooking & gathering. Sliders from the kitchen lead out to an oversized deck, creating a seamless indoor-outdoor flow for hosting. The kitchen opens directly to a large family room with built-ins & fireplace, making it the perfect spot to unwind. A formal dining room for special occasions and a bright living room that offers additional flexible living space. The second floor features four generously sized bedrooms and two full bathrooms. The spacious primary suite includes its own private full bath and an impressive walk-in closet. The additional bedrooms are well-proportioned and ideal for family members, guests, or home office space. The finished walk-out lower level adds over 1,100 square feet of additional living space & includes another full bathroom. This versatile area is perfect for a guest suite, gym, office, media room, or playroom. With sliders to the private backyard, you have easy access to the above ground pool. Additional highlights include a two-car garage, central air, & a beautifully landscaped lot. Plus...City water & sewers and economical solar panels to keep your electric bill way down. With its generous layout and excellent location, this home truly offers the best of comfortable living.