luxury real estate for sale Chatham, United States

Set on a quiet street just a short distance from Red River Beach, this six-bedroom residence offers an exceptional setting for Cape Cod living. Surrounded by mature plantings and natural privacy, the property feels peaceful and inviting while remaining close to the area's beaches, villages and coastal amenities.Designed for effortless summer living and entertaining, the spacious backyard features a large deck, storage shed and generous lawn. A private path providing direct access to the Cape Cod Rail Trail is perfect for morning bike rides, scenic walks, or exploring the Cape. The first-floor primary suite opens directly to the deck and outdoor shower, creating a seamless connection between indoor comfort and the relaxed outdoor lifestyle. Whether enjoyed as a cherished summer retreat, a year-round residence, or an investment opportunity, this property presents an ideal way to experience the very best of life on Cape Cod.

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.

Tucked away in one of Harwich's most desirable areas, this exceptional four-bedroom home offers a rare blend of privacy, space, and quintessential Cape Cod living. Set on a beautifully secluded lot, the property invites you to relax and entertain with ease.The expansive interior features two generous living rooms, providing flexible spaces for gathering, unwinding, or hosting guests. A full dining room flows seamlessly into an inviting, well-appointed kitchen designed for cooking and entertaining. Convenience is key, with laundry on both the first and second floors, ensuring everyday ease for households of any size.Outdoor living is just as impressive, featuring a large, sun-filled deck ideal for dining or summer entertaining, along with an outdoor shower to rinse off after a day at the beach. A two-car garage with additional storage space adds practicality to this thoughtfully designed home. Located just a short distance from Thompson's Field, Red River Beach, and the shops and restaurants of Harwich Port.

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.

Charming and incredibly cozy, this home feels like a true retreat. Outdoor space is fenced in and has mature perennials and an inviting pergola. The perfect place to unwind and entertain. Inside, find comfort and style. The huge basement offers amazing potential. Bring your imagination - this vast space can easily be converted into your dream hobby room, workshop, or additional living area. See it today!

Overlooking a tranquil pond, 22 Winslow Drive offers a peaceful setting with a strong sense of privacy. Birds move easily through the surrounding landscape, and the quiet setting creates a calm and natural atmosphere. This gracious Cape Cod home has been cherished by four generations. Thoughtfully expanded over the years while preserving its warmth and character. Inside, more than 4,000 square feet of living space unfolds with a comfortable and natural flow. Hardwood floors, exposed beams, fireplaces, and generous gathering spaces create a welcoming environment for everyday living. A flexible fifth room within the home can be privately sectioned off and features its own exterior entrance, full bathroom, and kitchenette. The home has been carefully maintained and thoughtfully updated, including a generator for year-round living. Finished space above the carriage house provides additional options for work or hobbies. Located just moments from Pleasant Bay. This property offers convenient access to many of the Lower Cape's most loved destinations while maintaining a peaceful residential setting.

Exceptional craftsmanship, forward-thinking efficiency, & a premier Orleans location come together just 1/2 mile from Pleasant Bay. Built by renowned Cape Associates, this beautifully maintained 3-bedroom, 3-bath home offers approximately 2,432 sq. ft. across three thoughtfully designed levels. The open main living area features a spacious living room, dining area, & well-appointed kitchen that flows to an expansive deck overlooking the private yard. Upstairs, the primary suite includes a walk-in closet, private balcony, & en suite bath, with two additional bedrooms and a full bath nearby. The lower level adds flexible space for a media room, office, gym, or guests. Set on over 3/4 acre with professional landscaping, a stone patio, and multiple outdoor living areas, the home is ideal for entertaining or relaxing after a day by the bay. A 5-kW solar array, solar hot water, spray foam insulation, HRV ventilation, MERV 16 filtration, Energy Star lighting, sustainable materials, & a HERS Index of 28 deliver exceptional comfort and remarkably low operating costs. Gold-certified and in excellent condition, this is a rare Orleans offering where quality, location, & efficiency align.

Be on the Water by Summer 2026--Experience premier luxury lakefront living on coveted Long Pond with a private sandy beach, dock, and endless boating, waterskiing, kayaking, and swimming right from your backyard. Designed by renowned architects Polhemus Savery DaSilva, this custom waterfront retreat blends timeless coastal design with modern comfort and exceptional craftsmanship. Enjoy sweeping pond views from the open-concept living, dining, and kitchen areas designed for effortless entertaining and relaxed waterfront living. The chef's kitchen features high-end finishes and a sun-filled breakfast nook with gas fireplace overlooking the water. Offering 4 spacious bedrooms, a water-facing den, and a private office with custom built-ins, the home is designed for both relaxation and everyday living. The walk-out lower level includes a wine cellar and flexible recreation space ideal for entertaining. Outside, the backyard leads directly to your private sandy beach and dock for the ultimate Cape Cod waterfront lifestyle.

Harwich Port! The Melrose! Inviting first floor condominium with 1288 square feet of well planned living space. 2 BRs, 2 full baths, center kitchen and spacious living/dining areas leading to a private screened porch which opens to the beautiful courtyard. Kitchen with wood cabinets, range, dishwasher and refrigerator. Guest bedroom wing with closet, full bath and bonus room-perhaps an office, game room or television/music room. Spacious primary bedroom wing with double closet, full bath and closet with washer/dryer. The HOA fees cover utilities, cable tv and internet, landscaping, trash removal, snow removal, window and appliance repair or replacement. Front desk service!Enjoy the lovely common areas: solarium, library, puzzle room, exercise room, dining room. Near Bank Street Beach, shopping and many fine restaurants. A Very Special Property!

Rare offering on picturesque Paw Wah Pond. A 3/4 acre salt waterfront parcel with direct access to Paw Wah and onto Little Pleasant Bay and the Atlantic beyond. A wonderful area of Orleans full of conservation and walking trails. Also, convenient to all the amenities. Engineer plans attached to listing.

The Grey House presents an exceptional opportunity to own property in the heart of downtown Harwich Port and in one of the most sought-after locations on the corner of Ayer Lane. Immerse yourself in this vibrant seaside community, where charming shops, excellent restaurants, and outdoor venues are right at your doorstep. Enjoy strolls through town or head to the beach to watch the sunset before dining and enjoying live music. Currently, the property serves as a beautiful interior shop, offering sunlit spaces with ample glass frontage for street exposure and plenty of parking. It includes large showroom spaces, dressing room, storage room, office, and a bathroom. Upstairs, you'll find a delightful one-bedroom apartment featuring a kitchen, living room, bathroom, and bedroom, perfect for owner use or as a rental investment. This prime location allows you to live and work in the heart of Harwich Port or explore the potential of transforming the property into a stunning single-family residential home. Whether you're looking to invest in a business, embrace the coastal lifestyle, or both, this property offers endless possibilities for creating lasting memories.

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.

Beautifully maintained four-bedroom, two-bath Cape with deeded rights to Long Pond. This inviting home features an open-concept floor plan with a seamless flow between the living, dining, and kitchen areas, creating a comfortable space for everyday living and entertaining. Thoughtful updates throughout enhance the home's appeal, while a slider off the dining area leads to a patio and fenced backyard, perfect for outdoor gatherings and relaxing after a day at the pond. The first floor offers two spacious bedrooms, an updated full bath, and convenient first-floor laundry. Upstairs, you'll find two additional bedrooms and a renovated full bath. Additional features include a lawn irrigation system, generator, outdoor shower, and attached one-car garage. Ideally located near Long Pond and the Cape Cod Rail Trail, with easy access to swimming, boating, kayaking, biking, and other outdoor activities. Whether you're looking for a year-round home, vacation retreat, or investment property, this property offers an excellent rental history and is rented for the summer season.