luxury houses with pool for sale Chatham, United States

A distinctive Cape Cod residence awaits in Harwich, less than two miles from the beach. Offering approximately 3,100 square feet of beautifully finished living space, this impressive home delivers exceptional accommodations across multiple levels. The main living area spans approximately 1,600 square feet with three bedrooms, refinished hardwood floors and a beautifully renovated kitchen highlighted by soaring vaulted ceilings, two-tone cabinetry, stone countertops, an oversized center island and newer appliances. Beautifully finished baths elevate the interior, including a spa-inspired primary retreat with stone surfaces, an expansive double vanity and an oversized glass-enclosed shower. An approximately 700-square foot finished lower level adds another bedroom and generous living space. Connected through the garage, an approximately 800 square foot additional living area offers two bedrooms and separate accommodations, creating wonderful flexibility for extended family or guests. Newer windows and skylights, siding, updated plumbing and electrical, and newer HVAC systems add to the extensive improvements. Outdoors, an expansive deck, private outdoor shower and generous yard create a wonderful Cape setting, all just minutes from the beach.

LEGACY COMPOUND WITH EXTRAORDINARY VIEWS // Pleasant Dreams is a spectacular one-of-a-kind family compound on perhaps one of the most desirable pieces of property on Cape Cod. This 2.5 acre estate boasts approximately 345 feet of saltwater frontage directly on Pleasant Bay with access to the Atlantic Ocean and showcases 180-degree breathtaking views of Pleasant Bay and beyond. This compound features 3 unique buildings. An approximately 7000 square foot main house, a guest cottage with pool and a boat house. This home contains the finest in craftsmanship and impeccable attention to detail. The large, open professional kitchen complete with top-of-the-line appliances, an oversized island and generous windows that overlook the bay makes this the natural centerpiece of the main house. Designed and professionally manicured landscaping with multi-level stone walls and gardens makes this property look magazine worthy. A truly unique family compound where memories will be created for a lifetime.

Your Turnkey Cape Cod Oasis and Income Generator has Arrived. Why wait for a ''dream home'' to be built when you can walk into one today? Set on a private acre, this isn't just a house--it's a high-end lifestyle package. Whether you're looking for a serene primary residence or a powerhouse investment, this 4 bedroom, 4.5 bath, new construction masterpiece comes fully furnished and ready to perform from Day One. Double the Luxury: This layout features two massive primary ensuites, each boasting spacious walk-in closets--perfect for multi-generational living or high-end rental appeal. Elevate your culinary game with a professional-grade Thermador range and oven, the centerpiece of a sun-drenched, open-concept heart of the home. Skip the furniture lead times; every inch of this home has been styled for comfort and coastal elegance. A shimmering pool is included, transforming your oversized lot into a private summer resort. With a rental permit in place, you can tap into the Cape's lucrative short-term rental market immediately. Tucked away in a tranquil, peaceful setting, you are just minutes from easy access to the walking trails of Thompsons Field and Cape Cod Rail Trail.

Welcome to 'Summer Salt', a stunning retreat where elegant coastal living meets timeless Cape Cod charm. Thoughtfully renovated, this exquisite home combines sophistication and ease, perfect for family gatherings or entertaining guests in style inside and out. Sweeping views of Arey's Pond and you own private deep water dock with easy access to Pleasant Bay. Beautiful grounds with a saltwater pool, hot tub, and large deck for gatherings or peaceful enjoyment. A must see if you are a boater, looking for a great investment, or want to enjoy summers on the Cape with your family and friends.

Set on two private acres in one of East Orleans' most coveted Barley Neck neighborhoods, 30 Chestnut Road is an exceptional Cape Cod retreat where refined interiors, resort-style outdoor living, and deeded beach access come together beautifully. Designed for both effortless everyday living and memorable gatherings, the home features four bedrooms and 3.5 baths, including a luxurious first-floor primary suite. The open-concept floor plan is anchored by a beautifully appointed kitchen with a generous center island, high-end appliances, and a butler's pantry. The adjoining living room, with custom built-ins, a charming window seat, and wood-burning fireplace, offers a warm and inviting place to gather, while the four-season sunroom brings the outdoors in throughout the year. A spacious bonus room above the garage provides wonderful flexibility for overflow guests, a home office, or additional recreation space. Outside, the property is truly extraordinary. The pool area feels like a five-star private oasis, surrounded by mature landscaping and generous space for lounging, dining, and entertaining. A private path leads to the neighborhood's deeded beach, making days on the water an effortless part of life here. Adding even more possibility is a separate cottage with electricity and a full foundation, offering exciting potential for conversion to an accessory dwelling unit, subject to Town approvals. Private yet close to the beaches, boating, and village amenities that make East Orleans so special, 30 Chestnut Road offers the space, setting, amenities, and lifestyle today's discerning buyers seek. This is Cape Cod living at its finest..

A strategic coastal acquisition opportunity for developers, hospitality groups and commercial investors in Dennis Port's established resort district. Situated across the street from the beach, this nearly one-acre property combines significant site area, approximately 50 existing parking spaces, a substantial commercial building previously operated as a 180-seat restaurant with a transferable liquor license and multiple residential structures. Located within the Chase Avenue Hotel Resort Area, the property benefits from a zoning framework designed to accommodate significant hospitality investment. Qualifying hotel development may reach up to 4½ stories or 50 feet. Chase Avenue is an active hospitality corridor surrounded by oceanfront resorts, vacation properties, beaches and established dining destinations. This concentration provides a built-in visitor base and places the property within one of Cape Cod's most recognizable resort settings. Whether envisioned as a boutique resort, hotel-condominium development, signature hospitality concept, restaurant revival, or adaptive-reuse project, this site offers substantial potential in a proven coastal destination.

Nestled on a spectacular 1.63-acre waterfront lot overlooking the serene waters of Rachel Cove, this exceptional property offers a rare combination of privacy, natural beauty, & extraordinary expansion potential. The beautifully sunlit custom home is situated in one of Orleans' most sought-after areas & is complemented by previously approved plans for a pool & guest house, which have since expired but may be resubmitted subject to current approvals & building requirements. Adding to its remarkable appeal, the sale includes an adjoining 1.78-acre waterfront parcel featuring approximately 335 ft of water frontage, creating a breathtaking estate setting with endless possibilities. Expand the existing residence to add additional bedrooms & living space, create a luxurious outdoor entertainment oasis w/ an expansive pool & patio area, & construct a substantial guest house to accommodate family & friends. Kayak directly from your property through Rachel's Cove to Nauset Harbor & the Outer Beach, dig a bucket of clams or simply relax & enjoy your own waterfront paradise. . The property's natural landscape presents an exciting opportunity to collaborate with Conservation on the removal of invasive species, potentiallyopening up even more magnificent views across Rachel's Cove. With nearly 3.4 acres of combined waterfront land, this is a rare and truly unique opportunity.

From the road, you would never know what is waiting out back. Tucked privately toward the rear of the lot is the kind of backyard where Cape Cod summer memories are made: a large in-ground pool, hydrangeas in bloom, plenty of lawn, and just enough of a basketball court for spirited games between swims. This is the house that becomes the gathering place—the one where everyone arrives with towels over their shoulders, the grill is going, music drifts across the yard and children and grandchildren beg for just one more swim before dinner. There is room for a crowd, yet the setting feels wonderfully sheltered and private. Loved by one family for many years, this sunny East Dennis ranch was designed for exactly that kind of life. With 1,919 square feet of interior living space, plus a 352-square-foot screened porch/sunroom, its unusual floor plan provides room to be together without requiring everyone to be in the same place. The fireplaced family room opens to the porch and backyard, creating a natural path between the house and the pool. The cheerful eat-in kitchen includes a sunny breakfast nook overlooking the yard, along with a pantry and conveniently placed laundry that make one-floor living remarkably easy. A traditional living room and formal dining room offer additional places for conversation, holidays, puzzles, card games or a quiet moment away from the activity. There are two comfortable guest bedrooms, two full baths and an exceptionally spacious primary bedroom addition positioned to look out across the lawn, gardens and pool—a peaceful retreat at the end of a full summer day. The interior is timeless, bright and welcoming. Portions of the exterior are ready for refreshing, but the bones are here, the setting is special and the possibilities are easy to see. More importantly, this is a home that already understands how people want to live: together when they choose, apart when they need, and outside as much as Cape Cod weather will allow. Homes seldom change hands in this coveted neighborhood, where pride of ownership is evident everywhere you look. Set between the beaches of Cape Cod Bay and Sesuit Harbor, it is close to Route 6A, neighborhood coffee shops and dining, and an easy walk for ice cream. Boating, water sports, lobster-roll cruises and the beloved Sesuit Harbor Café are only minutes away. One family has filled this home and backyard with years of pool parties, cookouts, celebrations and ordinary days that became treasured memories. Now it is ready for its next family to join this spectacular East Dennis neighborhood—and become the house where everyone gathers once again.

Presenting an offering of rare distinction. Refined coastal living, classic architecture and impeccable craftsmanship blend to create a unique sense of privacy, elegance, and pleasure. Nestled upon the shores of iconic Bass River, bask in waterfront living in this exclusive legacy estate replete with a deep water dock, private beach, and spectacular pool and spa. Beyond the auto gates, this private enclave encompasses a main house, carriage house, guest house and boathouse. The estate is set among lush plantings, exquisite gardens, curated vistas, and secluded courtyards. The sun-drenched interiors boast a peaceful balance of function and modern refinement. Custom appointments, outstanding finishes and bespoke details provide exceptional continuity. A deep-water dock and elaborately designed pier, capable of welcoming a substantial yacht with additional space for two vessels, offers direct access to Nantucket Sound and the Atlantic. This highlights the estate's stature as an ultimate residence for those seeking leisure and adventure. The setting, extraordinary amenities and elegance celebrate the unparalleled rhythm of a timeless, Cape Cod lifestyle.

Backing directly to the Cape Cod Rail Trail and the National Seashore, this custom 3 BR, 3.5 BA cape ranch offers 3,638 SF of finished living space, and on a quiet day the sound of the surf reaches the yard. Marconi Beach is about a mile away, no Route 6 required. This is a seriously well-built home, crafted with some of the finest materials and finishes available and laid out for the way people actually gather. A cathedral-ceilinged kitchen and dining area anchors the main level, with Medallion cabinetry, Silestone counters, a custom tile backsplash, premium appliances, and an oversized island, opening seamlessly to the outdoor living areas. All three bedrooms are en-suite, with the primary on the main floor. The lower level soars with 10 foot ceilings, a professional-grade bar (custom lighting, under-counter wine cooler, sink, bespoke built-ins), a family room with wood burning stove, and a private en-suite bedroom with its own entry. Outside, the private rear yard is a true retreat: heated saltwater pool, expansive hardscaping, outdoor shower, firepit, and gas grill. The landscaping is professionally designed, irrigated, and further elevated by the current owners. The systems tell a story of eco-minded self-sufficiency. Seller-owned solar panels keep energy costs and the home's footprint low, and a Level 2 EV-ready outlet in the 2-car garage awaits the charger of your choice. When the unexpected New England nor'easter rolls through, the 20KW Generac whole-house generator on a 1,000 gallon underground propane tank keeps every light on, and with the wood stove glowing, this home carries on comfortably when the grid cannot. Three-zone heat and central air round it out. Recently installed is an Advanced Whole-House Water Treatment System which includes sediment, reverse osmosis, and UV purification. The owners have documented every system, feature, and improvement in a handbook containing everything a new owner needs to move in with confidence from day one. It is a rare gift, and it tells you everything you need to know about how well cared for the home you are buying truly is.