luxury houses for sale Eastham, United States

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

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.

Welcome to this classic Cape-style home,ideally located just around the bend from Bakers Pond.Now offered at a new price,this is an excellent opportunity to make your move and enjoy the remainder of summer in a desirable setting.Designed with a flexible and functional layout,the main residence offers 2,092 sq ft of versatile living space.The first floor features a spacious primary en suite bedroom,a second bedroom,a 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 flexible space,perfect for a home office,recreation area,gym,or storage.A standout feature is the attached two-car garage with a one-bedroom apartment above,offering excellent potential for multigenerational living,guest accommodations,a private office,or possible rental income.Move-in ready with opportunities to personalize and build equity,this property combines space, flexibility and value in a sought-after location. Lot 69 is combined with 67.Buyers/agents to verify all information.Some photos virtually staged

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.

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!

Just in time for Summer 2026! Desirable north of Rte 6A location and easy stroll to 3 Bay Beaches - Paine's Creek, Mant's & Saint's Landing. This cozy cottage, with an open floor plan, offers easy living and the perfect Cape Escape with two beds/one bath. Bonus shaded patio area outside with dining space to enjoy morning coffee or a grill and chill summer BBQ. Everyone's favorite outdoor Cape Cod shower and a shed for storage, round out this property. Many updates include: newly shingled exterior siding and trim, mini splits for cooling and heat, vapor barrier installed in basement crawl space and kitchen appliances. Passing Title V. Also, available for sale: a mini mobile office. Owner will remove, if buyer not interested. Do not miss this opportunity! Brewster's beautiful summer sunsets on the bay, await the next owner.

Nestled in Chatham's highly sought-after RiverBay neighborhood, this beautifully updated Cape-style home offers the perfect blend of classic charm and modern comfort. Featuring 3 bedrooms and 2.5 baths, the home is thoughtfully designed for both everyday living and effortless entertaining.A first-floor primary suite provides a private retreat, complete with a generous walk-in closet and a cozy wood-burning fireplace. The updated kitchen opens seamlessly to inviting living spaces, including a sun-drenched family room with a gas fireplace and direct access to a private patio overlooking professionally landscaped grounds. Wide pine floors flow throughout the first level, enhancing the home's warm and welcoming character. An additional living room with a wood-burning fireplace offers yet another comfortable gathering space. The open floor plan creates an easy flow between rooms.Upstairs, you'll find two spacious bedrooms, a full bath, and an additional large walk-in closet. The finished lower-level room offers flexible space ideal for a home office, game room, or exercise area. Other features include a 2 car garage with storage overhead and close proximity to Pleasant Bay.

Tucked away in a private North Chatham setting with deeded rights to Lovers Lake just a short distance away, this extensively renovated 2,000 sq. ft. home offers the ideal blend of comfort, style, and turnkey ease. Thoughtfully updated throughout, the home features a renovated kitchen and bathrooms, air conditioning, and inviting living spaces designed for year-round enjoyment. The main level showcases beautiful wood floors, cathedral ceilings, exposed post-and-beam details and a powder room. The primary suite is located on the second floor with its own private bath and walk in closet, while the walkout lower level offers two additional bedrooms, a full bathroom, and flexible finished space for family, guests, or a home office. Outdoors, the spacious back deck is large enough for both dining and lounging, making it perfect for summer entertaining or quiet mornings surrounded by nature. With its private setting, extensive renovations, and deeded access to one of Chatham's beloved freshwater ponds, this home is ready to enjoy from day one.

Located in the sought after neighborhood of Countryside Estates. Sitting on a knoll this home offers gleaming hardwood floors throughout and open concept. The soaring cathedral ceilings in the kitchen and family room makes this home light and bright ! All stainless appliances are almost brand new and the oil tank has just been upgraded to double wall meeting today's regulation. There is natural gas and town water in the road, The wood burning fireplace creates ambiance when sitting in the family while relaxing with a good book or watching TV.The yard is filled with beautiful perennials that explode throughout spring and summer. The seller will install a new septic and hook up to town water.

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.

Chatham By The Sea. Rare 50-year offering where LOCATION presents a premier opportunity in Chatham. Coveted location 2 blocks to downtown Chatham Village. Chatham Fish Pier, Oyster Pond, Veterans Field, Cow Yard Landing, shopping, groceries, tennis, golf, 1/2 mile away. Spacious one-floor living with room to expand. Ranch home is 1531 square feet and includes 3 bedrooms, large formal living room with fireplace, large kitchen, dining area. The en-suite primary bedroom features a full bathroom with large walk-in shower. There is also a full family bathroom. Poured concrete foundation. 2019 roof, 2017 boiler, and attached oversized 2-bay garage. Central air conditioning, recessed lighting, 4 zone heating system, hardwood flooring. Basement is semi-finished and includes a fireplace, workshop and utility room. Sited beautifully on 3/4 of an acre delivering south, southwest sun exposure. Public water, private sewer. Engineering completed 5/14/26 for a new 3 bedroom traditional Title V septic. Design is also completed 6/30/2026. An in-ground pool is possible of interest.

Back on the market! Lovingly maintained and thoughtfully enjoyed over the years, this classic Chatham ranch reflects true pride of ownership. A traditional layout offers three bedrooms, including a primary with en suite bath, and easy, comfortable living throughout. Recently refreshed with a full interior paint update and beautifully staged, the home feels bright, welcoming, and ready for its next chapter.Set on a generous lot, the property benefits from adjacent green space that enhances both privacy and a sense of openness. The backyard extends toward a peaceful conservation area, creating a quiet, natural setting ideal for relaxing or entertaining.A detached two-car garage adds exceptional versatility with beautifully finished space above, complete with a full bath, private entrance, and its own deck overlooking the conservation land. Ideal for a home office, studio, guest overflow, or recreation space (buyers/agents to verify use).Additional potential can be found in the walkout basement lower level, offering opportunity for expanded living space over time. A special property in a beloved Chatham location, ready to be enjoyed for years to come.

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.

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.

Location,Location, Location ! 409 Main Street in the heart of downtown Chatham Village offers a rare and highly desirable combination: a mixed use building with first floor commercial space with showcase windows, maximum retail exposure and heavy foot traffic along with a fully renovated spacious separate second floor of residential living. There are 5 private in-town parking spaces behind the building and is located in the coveted GB-1 zoning district that has the most versatile business-use options available. The first floor commercial space features an open floor plan with 3 large areas and 4 oversized showcase windows putting your business directly in front of passing pedestrian traffic. The second floor apartment was fully renovated in 2019 and includes one bedroom, a full bath and laundry, and an open concept kitchen and a living area with vaulted ceilings. A large mahogany deck provides excellent outdoor living space. Both floors are independent of one another with separate A/C and heat. Don't miss this opportunity to own a versatile property that offers both exceptional business potential and strong investment value. Seller is the Owner/Broker.

Perfectly positioned to capture breathtaking sunsets over Bucks Creek, this meticulously updated 2,700-square-foot residence features 4 bedrooms and 3.5 bathrooms. Just a short distance from Nantucket Sound and Hardings Beach, this craftsman-renovated home offers a spacious open floor plan highlighted by vaulted, beamed ceilings and expansive windows that showcase ever-shifting views of the tidal marsh. Designed to host guests, the first floor includes a stunning professional-grade kitchen with an oversized quartz island that opens to an elegant dining area, two fireplaces, and two primary bedroom suites. The property is rounded out by a large wrap-around deck, two additional second-floor bedrooms, a one-car garage, and a full basement with heat and air conditioning. The house is .7 mi from Harding's Beach and 1.9 miles from downtown Chatham's shops and restaurants. Pull up a chair and savor Mother Nature's ever-changing show.

Perfectly positioned in the heart of Chatham's Old Village, this 4-bed, 2-bath home offers the rare combination of historic charm, water views of Chatham Harbor, and an exceptional in-town location. Just moments to Lighthouse Beach, Main Street shops, restaurants, and golf, this circa-1850 Greek Revival is filled with warmth and character. featuring a sunny eat-in family room with beamed ceiling and sliders opening to the deck, an adjacent cozy kitchen, and a welcoming front living room with gas fireplace and antique wood floors. The convenient first-floor primary bedroom is located near a full bath with laundry, while the second floor offers three additional bedrooms, a bath with shower, and extra closet space. For year-round comfort and peace of mind, improvements include a gas furnace (2025), roof (2013), updated windows, vinyl siding, and generator. Outside, the wraparound deck with awning overlooks the private backyard, an inviting setting for outdoor entertaining, lawn games, or simply relaxing after a day at the beach. An unusually large storage shed provides ample space for boating and recreational gear, gardening tools, or possible studio.

Welcome to Cape Cod living in this beautifully updated three-bedroom, first-floor living home. Clean and coastal, this inviting property is ideal for seasonal summer retreats or comfortable year-round living. The renovated kitchen features custom cabinetry, quality finishes, and a functional layout designed for everyday living and entertaining. Thoughtful updates throughout the home create a bright, fresh, and move-in-ready atmosphere. Outside, meticulously landscaped grounds showcase beautiful seasonal plantings, lush lawn, and a full irrigation system, providing exceptional curb appeal and effortless maintenance. Enjoy the convenience of being just a short distance to the Cape Cod Rail Trail, shopping, Harwich Center, and the restaurants, beaches, and charm of downtown Harwich Port. Whether you're seeking a vacation getaway, investment opportunity, or primary residence, this exceptional property offers the perfect blend of comfort, convenience, and coastal charm.

LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, this residence beautifully blends elegance and comfort. The open floor plan showcases oversized windows and soaring ceilings, allowing natural light to pour in and illuminating the stunning views of the swimming pool, spa, outdoor kitchen, patio, gas fire-pit, outdoor shower, and irrigated fenced-in lawn. Ownership includes deeded neighborhood access to Lighthouse Beach. The gourmet kitchen and oversized island seamlessly integrate with the dining room, custom bar, pantry, and wine storage. The inviting living room features a cozy gas fireplace. The fifth bedroom has been thoughtfully transformed into an inspiring study. Ascending to the second floor, you'll discover four wonderfully proportioned bedrooms, each offering distant Atlantic Ocean views, and three stylish full baths. The primary suite is a true retreat, boasting glorious views, a spacious walk-in closet, a dressing room, and an exquisite bathroom and shower. Around the corner is the Outermost Harbor Marina, and the nearby Old Village is the gateway to the start of Chatham's Main Street.

There are certain neighborhoods on Cape Cod that people discover and immediately understand why so few homes are ever available.The kind of places where homes are thoughtfully sited on generous lots, mature landscaping softens the view from the road, and a quiet sense of permanence is immediately apparent. Places where ownership is often measured in decades rather than years, and where homes rarely come to market because they are quietly passed along through neighbors, friends, and family connections before the rest of the world ever knows they are available.Windward is one of those places.This coveted East Dennis enclave of custom McPhee-built homes has long been regarded as one of the area's best-kept secrets. Tucked away just minutes from some of the Cape's best beaches, Windward offers something increasingly difficult to find: privacy, space, and a level of understated elegance that never asks for attention yet quietly commands it.There are no gates here. None are needed.The winding roads, generous setbacks, meticulously maintained homes, and extraordinary pride of ownership create a feeling of exclusivity that is difficult to define but impossible to miss. It is a neighborhood for those who appreciate breathing room, who value quality over flash, and who understand that true luxury is often found in what isn't crowded, hurried, or easily replicated. Perhaps that is why so few homes ever become available. Once people find Windward, they tend to stay. Set near the end of a gentle curve in the road, 9 Baker's Pond enjoys one of Windward's most desirable settings. A sweeping circular driveway welcomes you to this custom Cape, thoughtfully designed to embrace both privacy and natural light. Inside, warm and inviting spaces include an eat-in kitchen with rich cherry cabinetry, a formal dining room ready for holidays and celebrations, and a comfortable living room centered around a handsome fireplace. The first-floor primary suite offers cathedral ceilings and a sense of retreat, while additional bedrooms and flexible living spaces provide room for family and guests. And then comes the surprise. Added by the current owners, the spectacular year-round sunroom was designed to do exactly what it does so beautifully--draw your eyes outward and showcase the extraordinary setting beyond. With soaring cathedral ceilings, shiplap detail overhead, and floor-to-ceiling windows that flood the space with natural light, it serves as both the heart of the home and a window into the remarkable oasis beyond. From here, the entire scene unfolds. What was completely hidden upon arrival reveals itself all at once--a private backyard oasis that feels more boutique resort than private residence. A heated saltwater pool with a cascading waterfall and graceful arcing water jets creates a resort-like experience, while an expansive bluestone patio, colorful plantings, and impeccably maintained grounds provide the perfect backdrop for both grand entertaining and quiet relaxation. The tiki hut cabana--with bar, refrigeration, television, and plenty of room for family and friends--invites spontaneous summer afternoons that effortlessly drift into evening. As landscape lighting begins to glow and the gardens settle into the soft light of dusk, it becomes easy to understand why so many treasured memories have been created here. Perhaps the greatest luxury is that it is all just steps from your back door. A private retreat designed to be enjoyed whenever the mood strikes. Some of the best moments of summer happen not at a destination, but at home. https://media.nausetmedia.com/sites/rgbdabmy/unbranded

Situated on Chatham's exclusive Stage Island, this 4 BR, 5.5 bath, shingle-style residence is designed for seamless indoor and outdoor entertaining. The bright, airy first floor is anchored by a great room with a Rumford fireplace, custom cabinets, 10' ceilings, and towering windows. The professional-grade kitchen features premier appliances, a pantry, a wet bar, and a large center island. Primary suites are on both floors, each with a large walk-in closet and a luxurious bath. The fenced-in yard offers two exceptional options for installing a large swimming pool and spa to complement the bluestone patio and built-in gas grill. The second story features an inviting family room with custom-built-ins and a gas fireplace, opening onto a broad deck with views of the Atlantic Ocean and the Outer Beach. The second-floor primary is complemented by two well-appointed guest suites. A private staircase leads to the bonus room with a full bath, located above the two-car garage and ideal for a gym, office, or guest accommodations. A whole-house generator and an in-ground irrigation system supplied by a private well add to what is an unparalleled value in the Chatham real estate market.