5-Bedroom Homes for Sale in Orleans, MA

Discover the perfect blend of historic charm and contemporary comfort in this deceptively spacious 5-bedroom 4.5 bath post and beam Cape just 1⁄2 mile from Orleans iconic Rock Harbor known for breathtaking sunsets, tidal flats, and coastal charm. Built in 1867 and relocated in the 70s, it blends timeless Cape Cod style with modern amenities, split HVAC, 6- heating zones, insulated windows, and

Deborah Salvatore Berkshire Hathaway Home Service New England Properties

This spacious 5-bedroom, 3-bath home is tucked away at the end of a quiet cul-de-sac, offering privacy and direct access to Harvey's Pond. Designed for both comfort and versatility, the property combines traditional Cape Cod charm with modern updates.Inside, you'll find gleaming hardwood floors, a welcoming fireplace, and a bright, open floor plan with architectural details that invite natural

Denise Kopasz Next Home Saltwinds Realty

An enchanting coastal retreat! Set alongside the Pleasant Bay estuary in one of Orleans' most private & naturally beautiful enclaves, this striking 5BR/5BA custom home blends relaxed coastal living with creative design & impeccable craftsmanship.Nestled among pines, rhododendrons, and roses, the residence offers expansive water views and exceptional privacy, while just minutes from world-class

Fran Schofield Berkshire Hathaway HomeServices Robert Paul Properties

For the first time in generations, this extraordinary Pleasant Bay compound--featuring the iconic ''Topside'' main residence and the charming two-bedroom ''Boathouse''--is offered as a rare, legacy waterfront estate. With a deep-water dock, moorings, and direct access to the bay, the property delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation potential. Both homes

Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

Ideally located in the vibrant commercial district of Orleans and overlooking scenic Town Cove, this 4,400+ square foot mixed-use building presents a rare opportunity for investors, developers, or business owners seeking a high-visibility location with tremendous potential. Built in 1840, this property features over 1,500 SF of street-level retail space, two residential apartments, and generous

Andrew Grattan Christie's International Real Estate Atlantic Brokerage

A rare offering on the shores of Little Pleasant Bay, 40 Tom's Hollow is a generational waterfront estate encompassing nearly four acres of bucolic landscape with an expansive shoreline, private sandy beach, and iconic boathouse. A winding drive leads through a serene coastal setting to a timeless center-entrance Colonial, where soaring ceilings and panoramic bay views set the tone. The

Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

WATERFRONT with deepwater access from Rachel Cove - a protected and picturesque bay off Town Cove. This lovely, expansive Cape was built in 1995 on a private, bucolic 1.23 acre lot and has been lovingly maintained ever since by the original family. Large, welcoming foyer features raised-panel wainscoting, and warm, maple flooring which continues throughout the main living area. Transom windows

Sarah Gammons - Ciampa Berkshire Hathaway HomeServices Robert Paul Properties

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

Jen Whitaker Gibson Sotheby's International Realty

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

Chris Rhinesmith Compass Massachusetts, LLC

Mayflower Point, Orleans. This extraordinary waterfront estate on Little Pleasant Bay is now complete for Summer 2025. Eastward Companies, synonymous with Lower Cape luxury homebuilding, has exquisitely designed this 5800 sq ft shingle-style masterpiece to showcase their coastal aesthetic in a fantastic saltwater setting. The covered entry porch beckons to the main floor which is entirely

Jeff Cusack Cove Road Real Estate