Orleans, MA Real Estate Search

Orleans, MA 5 Bedroom Homes for Sale

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Newest Orleans, MA 5 Bedroom Homes for Sale

$4,200,000
5 Beds ⋅ 5 Baths ⋅ 73570743 MLS
SET DIRECTLY on the Pleasant Bay estuary, 5 Kidd Way offers expansive water views, immediate deepwater boating access, and exceptional privacy on nearly 1.5 acres. This distinctive 5BR/5BA home spans three finished levels, with flexible living spaces designed to accommodate family and guests. The light-filled main level features open living and dining areas overlooking the water, a wood-burning fireplace, updated kitchen with quartz countertops and new appliances, and a spacious primary suite. Multi-level mahogany decks extend the living outdoors and provide an ideal setting for dining and entertaining. Additional bedroom suites and flexible spaces are located on the upper and lower levels, including private exterior access from the lower level. A separate heated and cooled guest cottage with full bath offers excellent possibilities for guests, a studio or home office, or potential ADU use. The 1.4+ acre setting provides room for a pool or additional accessory structure, subject to approvals. Enjoy private shoreline access for kayaking, paddleboarding, swimming, sailing, and boating. The existing deepwater mooring is available subject to Harbormaster approval.With a proven peak-season rental history approaching $100,000 per year, 5 Kidd Way offers an unusual combination of waterfront lifestyle, flexibility, and income potential—all just minutes from Orleans and Chatham. NOTE: A substantial addition and renovations have been completed at the property. These alterations are not yet reflected in public records, assessments, or estimated valuations.

5 Kidd Way, Orleans

Listing courtesy of Listing Agent: Frances Schofield from Listing Office: .
$2,999,999
5 Beds ⋅ 5 Baths ⋅ 73560573 MLS
Let your Cape Cod story begin at ''Fields Cove'' - an extraordinary waterfront retreat where sweeping views of Frost Fish Cove, surrounding conservation land, ever-changing tidal waters, abundant wildlife, and spectacular light create one of Orleans' most captivating settings. Tucked away on nearly two private acres, Fields Cove offers a rare opportunity to own a destination estate - yet moments from the best of Cape Cod. Fields Cove is a resort-like setting for your special Cape Cod experience. Lose track of time luxuriating in the waterfront heated pool and launching kayaks and paddle boards from your own private water access. Watch ospreys and herons glide overhead, see otters surface in the cove, and hear only birdsong from the property's many decks, patios, and landscaped gardens. As the tide ebbs and flows, enjoy views of boats sailing to Pleasant Bay. Each season paints a new coastal masterpiece outside your windows. Designed for large gatherings while still providing privacy, this home features multiple living areas, three primary suites, two kitchens, five full baths, and thoughtfully designed spaces where family and guests can celebrate together--or slip away with a favorite book and a view. Extensively renovated and improved, the residence blends Cape Cod charm with modern comfort and exceptional craftsmanship throughout.Whether envisioned as a multi-generational retreat, luxury vacation home, year-round residence, or investment property with an established rental history, Fields Cove offers a lifestyle rarely found on Cape Cod. Its unique blend of privacy, beauty, and tranquility has attracted admirers from around the world--including a Hollywood mega-star who chose Fields Cove for a private stay and left raving about the experience.If you venture beyond your sanctuary, you'll appreciate walkable access to Kent's Point Conservation Area, Namequoit Sailing Association, Crystal Lake, and Pleasant Bay, with beaches and landings for swimming, kayaking, paddle boarding, and boating in some of the Cape's most treasured natural landscapes. Fields Cove is where cherished memories are made and your Cape Cod dream can begin.

58 Keziahs Ln, Orleans

Listing courtesy of Listing Agent: Cape Island Estates Group from Listing Office: Christie's International Real Estate Atlantic Brokerage.
$1,699,000
5 Beds ⋅ 4 Baths ⋅ 73560125 MLS
Beautifully renovated inside and out! This home is the epitome of Cape Cod pride. Boasting five large bedrooms, three and a half baths, and the essential first-floor living. An extensive home renovation including, remodeling all bathrooms down to the studs, custom cabinetry throughout, all new windows and exterior doors, refinished hardwood floors, tastefully designed kitchen with quartzite countertops and stainless steel appliances. This house is also equipped with a new hot water heating system, central A/C, elegant front and back hardscaping, and hooked up to town water! A versatile location close to Sunken Meadow Beach, yet also an easy drive to Nauset Light Beach, one of Cape Cod's most famous ocean side beaches. A short distance to shopping, restaurants, the Cape Cod Rail Trail, the Wellfleet Drive-In Theatre, and more. So much value has been added to this property making it a top contender for those looking for a new Cape Cod residence, vacation home, or rental investment. The most valuable asset is peace-of-mind, come fall in love with this home and move right in!

160 Quail Cover Lane, Orleans

Listing courtesy of Listing Agent: Matthew Burger from Listing Office: Kinlin Grover Compass.
$4,295,000
5 Beds ⋅ 6 Baths ⋅ 73494776 MLS
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 your own private deep water dock with easy access to Pleasant Bay. Beautiful grounds with a saltwater pool, a hot tub, and a 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.

36 Areys Lane, Orleans

Listing courtesy of Listing Agent: The Eva Scott Group from Listing Office: Gibson Sotheby's International Realty.
$7,995,000
5 Beds ⋅ 7 Baths ⋅ 73493011 MLS
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.

77 Towhee Lane, Orleans

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$1,099,000
5 Beds ⋅ 4 Baths ⋅ 73483696 MLS
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.

67-69 Bakers Pond Rd, Orleans

Listing courtesy of Listing Agent: Kirsten Johnston from Listing Office: Gibson Sotheby's International Realty.
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