luxury real estate for sale Eastham, United States

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.

Now's your chance to own one of East Orleans' most iconic properties!Once home to the beloved Kadee's Lobster & Clam Bar, a bustling fish market, a welcoming gift shop, and the ever-popular Apple Grove Mini Golf, this unforgettable property is ready for its next chapter. At the heart of it all is the original family home, which later became Kadee's Gray Elephant Inn, offering classic Cape charm with a storybook past. Spanning 1.79 acres across three parcels--212, 214, and 216 Main Street--the property currently features a main building divided into seven apartments. Any plans to maintain the apartments will require town approval. Town sewer is at the street and expected to be ready for tie-in by January 2026.Whether you're looking to revive a treasured local landmark or bring a fresh new vision to life--think hospitality, housing, or something wonderfully unexpected--this prime East Orleans location offers high visibility, ample on-site parking (a rare gem!).Opportunities like this don't come around often!Please reference commercial listing MLS#22500108 that complements this listing. Seller open to Buyer concessions

Enjoy the best of Orleans from this beautifully remodeled third-floor condo, featuring a stunning new kitchen with quartz countertops and all new appliances, along with a newly renovated bathroom. The bright, open floor plan creates an inviting space, while newly installed air conditioning adds comfort. Accessible by elevator or stairs, this turnkey property is ready to enjoy. Just steps from restaurants, boutiques, gyms, shopping, and the farmers market, with nearby access to the Cape Cod Rail Trail and close proximity to Skaket and Rock Harbor beaches.

Welcome to 28 Greymoor Way in the heart of East Orleans, Ideally situated on a quiet cul-de-sac just a 1/2 mile from Nauset Beach. Whether you are looking to spend your days relaxing on one of Cape Cod's most iconic beaches or exploring the dunes with your ORV this location offers the very best of coastal living. Set on .46 acre lot this 3 bedroom 2 bath 1,730 sq foot home provides convenient access to shopping, restaurants, golf and highway access while maintaining the privacy and tranquility that makes East Orleans so desirable. A standout feature is the detached barn, complete with artists studio and additional storage offering endless possibilities. Preserve it as a creative retreat, transform it into a yoga studio or fitness studio, or explore as a potential (ADU), subject to local approvals. This property is being offered ''as is'' , presents and exceptional opportunity for the next owner to reimagine and personalize a special Cape Cod retreat. Bring your vision and create a home that will be enjoyed for generations. Septic inspection has failed and buyer is to assume ...

Enjoy carefree living close to all Orleans has to offer in this elegant, 62+ independent living community. This 3rd Floor corner end unit features a bright open and spacious floor plan with 2 bedrooms and 2 full baths, full size kitchen, dining room with extra windows, living room with large outdoor balcony. Primary bedroom has 2 closets & a private bath with walk-in shower. Guest bedroom or family room features 2 walls of custom built-in shelving/cabinets. Brand new carpeting throughout. Monthly fee includes: 24/7 concierge, security, utilities-including gas heat, A/C, basic cable, electric, water; trash removal, repair & maintenance of the unit including major appliances & windows, exterior maintenance, garage parking & interior storage unit. Optional gourmet meals prepared by a private chef & served in the formal dining room; or order meals brought to your door. Common areas: kitchen & sunny solarium where residents enjoy gathering for morning coffee, a library, large living room w/fireplace, exercise room & visitor's suite for extra overnight guests.

Tucked away on a quiet Wellfleet cul-de-sac, this 3BR/4BA Cape offers prime access to Marconi Beach, the Cape Cod Rail Trail, and Mass Audubon Wellfleet Bay Wildlife Sanctuary. With 2,441 sq ft (approx. ± sq ft), the layout opens from an updated kitchen into bright living and dining spaces enhanced by skylights and a pellet stove. Extensive upgrades include new windows and insulated siding, updated plumbing, new heating and AC systems, a newer hot water heater, renovated lower level, refreshed kitchen and baths (including partial second-floor updates), and a new front deck. The finished lower level adds flexible space for work or recreation, while a detached outbuilding with a kitchenette, bath, and loft offers added versatility. Ideal for year-round living or a seasonal retreat, set in a peaceful, established neighborhood near the National Seashore.

Located on a beautiful cul-de-sac surrounded by quintessential Cape Cod homes, this rare panhandle lot sits waiting for your Cape Cod dream home. Lot is offered with engineering, bulding plans and permits in place. Skymeadow Drive is a wonderful, lovingly maintained neighborhood just minutes away from Skaket Beach and Cape Cod Bay. Walking, biking, close to Orleans village center-this area provides everything you need. Easy access into lot. More details upon request.

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.

A rare opportunity to own an ocean view home in the exclusive Pochet Association.This quality-built post-and-beam home features soaring ceilings & expansive walls of glass that fill the home with natural light. Designed for comfortable coastal living, the spacious six-bedroom residence features an open floor plan, thoughtfully positioned decks, and views of the Atlantic. Private access to Nauset Beach (one of Cape Cod's finest ocean beaches) is a 10-minute walk from the property via the association bridge and boardwalk -- perfect for swimming, surfing, walking, surfcasting, or simply enjoying a day by the sea. A town landing on Pochet Inlet is located minutes away in the association for boating in Pleasant Bay. Situated on a large, private lot, the beautifully landscaped grounds are enhanced by specimen trees, shrubs, and gardens, creating a private and tranquil setting. A detached garage with ample bonus space & full bath above offers exceptional flexibility with overflow space for guests, home office, or creative pursuits. With some updates & town approvals, it could potentially become a rental or ADU. Ideally located near the charming village of East Orleans with its acclaimed restaurants, galleries, & shops, this exceptional property offers an opportunity to live the Cape Cod lifestyle at its very best.

Welcome to this classic Cape-style home featuring a full 1-bedroom apartment above the garage—perfect for overflow guests, extended family, or rental income. The main residence offers 2,092 sq ft of flexible living space. The first floor includes a spacious primary en-suite bedroom, second bedroom, full bath with laundry, and bright kitchen, dining, and living areas ideal for everyday living and entertaining. Upstairs are two additional bedrooms and a shared full bath, providing plenty of room for family and guests. The walk-out lower level adds 758 sq ft of versatile space, perfect for a home office, recreation room, gym, or storage. Move-in ready with opportunities to personalize and build equity, this home combines space, flexibility, and value in a sought-after location just around the bend from Bakers Pond. Lot 69 is combined with Lot 67. Buyers/agents to verify all information. Some photos virtually staged.

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..

Exceptional Orleans opportunity for builders, developers or buyers seeking a property with significant potential. Set on a private, beautifully wooded 1.28-acre parcel, this property offers an existing 3-bedroom, 2-bath residence of approximately 2,005 square feet, a two-car garage and a spacious, level setting with mature trees. The existing Cape-style home offers considerable character, including wood floors throughout, exposed beams, a brick-surround wood-burning fireplace, soapstone kitchen sink and built-in shelving in the primary bedroom. A deck, fenced-in backyard and existing outdoor structure further enhance the property. The existing residence could be renovated, expanded or replaced, subject to Town of Orleans approvals, with potential for a 5-bedroom residence. The property's generous acreage, privacy and favorable setting provide an excellent foundation for creating a substantial new Cape Cod home or thoughtfully reimagining the existing property. Conveniently located near Nauset Beach, Crystal Lake, Kenrick Woods conservation trails and Arey's Pond, with the shops and restaurants of downtown Orleans nearby!

I WANT A CAPE HOUSE THAT FEELS A WORLD AWAY. I want the driveway to wind through the trees, leave the road behind, and then there it is-our beautiful escape overlooking the water. I want to wake up to amazing views, head down to our own dock, and sail out along the river to Pleasant Bay. I want lazy afternoons on the deck, long summer dinners in a screened porch... and a massive outdoor fireplace for cool nights. And enough room for everyone to be together but without feeling crowded. And here it is. Set high on nearly an acre above saltwater Arey's Pond, this shingle-style home has the feel of a fine yacht, with dazzling views, open gathering spaces, cozy nooks, fir floors, four fireplaces, and a bridge-like upper-level walkway. Great for entertaining, the wet bar in the living room is the mainstay while a delicious meal comes together in the timeless chef's kitchen. Outside, bask in the freedom of your private dock, play some croquet on the back lawn, pick some blueberries for a home-made pie, and spend the evening on the screened porch. Three bedroom suites feel like their own retreats when the day is done. Once you're here, there's really nowhere else you need to be.

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.

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.

Tucked at the end of a quiet Brewster cul-de-sac, this beautifully renovated and expanded residence offers exceptional privacy on 1.38 acres of thoughtfully landscaped grounds. Equally suited as a sophisticated year-round home or an inviting Cape Cod summer retreat, the property is ideally located near the Cape Cod Rail Trail, Nickerson State Park, and the bay beaches at Linnell Landing and Crosby Landing. Inside, a light-filled open floor plan creates an effortless flow for everyday living and entertaining. The beautifully appointed chef’s kitchen anchors the main living space and features Sub-Zero refrigeration, wine cooler and freezer drawers, a generous marble island, and custom Boos block cutting board. Hardwood floors, refined finishes and carefully considered details create interiors that feel both polished and comfortable. The desirable first-floor primary suite provides a private retreat with a walk-in California Closet and en-suite bath featuring radiant-heated tile flooring. Two additional bedrooms offer comfortable accommodations for family and guests, while the finished walk-out lower level provides flexible additional space for recreation, fitness, media, guests or other lifestyle needs. Designed to embrace Cape Cod’s indoor-outdoor lifestyle, the home features a heated three-season room with Infratech heaters, expansive deck, outdoor shower, fire pit, raised planting beds and beautifully maintained gardens and grounds. Whether gathering around the fire on a summer evening, gardening, entertaining or simply enjoying the peaceful setting, the outdoor spaces are an integral part of the property’s appeal. A detached office provides an ideal setting for remote work or creative pursuits. Central air and extensive updates complete this distinctive Brewster property, where privacy, gracious open living spaces and proximity to some of the Lower Cape’s most treasured beaches and outdoor destinations come together for effortless Cape Cod living.