Orleans MA Waterfront Properties

MLS Number 22404581

• Residential
• Bedrooms 5
• Bathroom 8
• Square Feet 7,539

Extraordinary new construction on sought-after Pleasant Bay. This rare opportunity features a stunning five-bedroom residence with a swimming pool, boathouse, deeded beach access, and rights to a private mooring. Showcasing unsurpassed quality and craftsmanship, the open concept floor plan caters to modern living with a spacious living and dining area with coffered ceilings, a gas fireplace, and sweeping water views through sliding glass doors that line the waterside of the home. The adjacent gourmet kitchen is a chef's dream with a Wolf range, Sub-Zero refrigerator, granite countertops, and a butler's pantry. Just outside, the pool and spa area provides a resort-like setting, complete with a cabana featuring a kitchenette, bathroom, and outdoor shower. A secluded first-floor primary suite offers total comfort and convenience, boasting a large walk-in closet and luxurious bathroom. On the second level, three well-appointed bedroom suites all enjoy bay views. The walkout lower level is perfect for relaxing after a day on the water, finished with an entertainment area, kitchenette, and full bathroom. Ideal for boating and fishing enthusiasts, the newly renovated boathouse on Pleasant Bay includes a kitchenette, living room, bathroom, and large deck with stairs to the water. Additional highlights include a three-car garage with a guest apartment above. Ready to be enjoyed, this one-of-a-kind estate delivers Cape Cod living at its finest, located minutes from Wequassett Resort, Eastward Ho!, and everything else the area has to offer. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

Listed by Paul E Grover and Matthew de Groot of Berkshire Hathaway HomeServices Robert Paul Properties

Buyers Brokers of Cape Cod, McKenna Associates
116 Route 6A
Sandwich MA, 02563
Office: 774-994-1900

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MLS Number 22403397

• Residential
• Bedrooms 5
• Bathroom 7
• Square Feet 7,372

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.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

Buyers Brokers of Cape Cod, McKenna Associates
116 Route 6A
Sandwich MA, 02563
Office: 774-994-1900

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MLS Number 22405726

• Residential
• Bedrooms 5
• Bathroom 8
• Square Feet 5,800

Mayflower Point, Orleans. This extraordinary waterfront estate on Little Pleasant Bay is now under construction. 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 dedicated to gathering and enjoyment. The coffered ceiling great room features walls of windows and access to the classic screened porch. The hand-crafted luxury kitchen is replete with features including a butler's pantry and a 14' custom island that seats eight. Extensive fenestration ushers in light and captures deep views. Ornate millwork and custom finishes adorn every room. The 2nd floor, accessible by stairs or an elevator, offers three guest suites plus an elegant primary bedroom wing and a fireplaced family room, both with dramatic views. The lower level provides media, exercise and additional sleeping space. The waterside outdoor area includes a saltwater gunnite pool, gas firepit, expansive granite patio and stairs to water's edge for swimming, kayaking and mooring access.

Listed by Jeffrey E Cusack of Cove Road Real Estate

Buyers Brokers of Cape Cod, McKenna Associates
116 Route 6A
Sandwich MA, 02563
Office: 774-994-1900

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Your Questions & Comments I have a question about the property at 64 Pershing Lane Orleans MA 02653 (#22405726).

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MLS Number 22501789

• Residential
• Bedrooms 4
• Bathroom 4
• Square Feet 2,413

A rare opportunity to own a piece of Cape Cod history in the coveted Barley Neck area of East Orleans. Available for the first time in nearly 80 years, ''Sargent Point'', affectionately named after the former governor of Massachusetts, is one of the most spectacular generational waterfront properties on all of Cape Cod. This 5+ acre private retreat enjoys unparalleled panoramic views of Little Pleasant Bay and the natural beauty of land trust protected Sampson and Hog Islands, with Nauset Beach behind. Enjoy access to your own private point, with 500 feet of direct waterfront, 150 feet of private sandy beaches and deep water mooring capacity. Located down a wooded private road, this classic year round home comes with 6 bedrooms, original wood floors, fireplaces, and a separate studio. Updated site plan and engineering now available. A legacy property with endless potential, Sargent Point is a pleasure to show, by appointment only.

Listed by Brian W Dougherty and Jack Tobin of Corcoran Property Advisors

Buyers Brokers of Cape Cod, McKenna Associates
116 Route 6A
Sandwich MA, 02563
Office: 774-994-1900

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Your Questions & Comments I have a question about the property at 63 Old Field Road Orleans MA 02653 (#22501789).

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MLS Number 22501030

• Residential
• Bedrooms 5
• Bathroom 7
• Square Feet 6,021

Stunning Salt Waterfront Estate on the Mill Pond with panoramic views to Roberts Cove & Nauset Harbor to the Light House & beyond!Superior quality throughout this 5 bedroom 5 1/2 bath home. Great privacy & beautiful easy to care for landscaping. Wonderful open sunny rooms & great flow. Large gourmet kitchen & formal dining room. Beautiful Great Room with a fireplace wall, sliders & a French door to the deck! Super first floor office. Great family room with a beamed ceiling, & it is adjacent to the screened in porch. Lovely first floor primary bedroom en suite with 2 walk in closets & adjacent office. Large sun filled guest rooms with fabulous views. Artistically beautiful inside & out! Short distance to Nauset Beach around the bend, swim in your pool or at the association private beach & sail from you private mooring to Nantucket!

Listed by Nikki Carter of William Raveis Real Estate & Home Services

Buyers Brokers of Cape Cod, McKenna Associates
116 Route 6A
Sandwich MA, 02563
Office: 774-994-1900

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Your Questions & Comments I have a question about the property at 30 Deer Run Orleans MA 02653 (#22501030).

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MLS Number 22501262

• Residential
• Bedrooms 6
• Bathroom 7
• Square Feet 4,000

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 cathedral-ceilinged great room, with pass-through hearth, forms the heart of the home--flanked by a custom kitchen and gracious dining area, perfectly positioned to capture the beauty beyond. A first-floor primary suite offers privacy and comfort, while separate guest quarters provide flexibility for extended stays. The finished walkout lower level adds space for recreation, gatherings, or overflow guests--all opening to a lawn that invites entertaining and the potential for a pool. Outside, a wide stretch of shoreline allows for private beach access, and mooring rights open the door to water-sport adventures. The historic boathouse, brimming with potential, anchors the property in authentic Cape Cod tradition. This is a rare legacy estate where nature and coastal elegance live in quiet harmony.

Listed by Guthrie Schofield Group of Berkshire Hathaway HomeServices Robert Paul Properties

Buyers Brokers of Cape Cod, McKenna Associates
116 Route 6A
Sandwich MA, 02563
Office: 774-994-1900

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Your Questions & Comments I have a question about the property at 40 Toms Hollow Lane Orleans MA 02653 (#22501262).

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MLS Number 22404490

• Residential
• Bedrooms 4
• Bathroom 7
• Square Feet 5,170
• Parking Spaces 8

Experience the pinnacle of sophistication with this exquisite new build by Eastward Companies which will be ready for spring occupancy. Tucked off Tonset Road and with frontage on Main Street, this elevated home boasts lovely marsh and Town Cove views as well as swimming, fishing, and boating. This superbly designed residence features an open floor plan ideal for entertaining. The upscale kitchen flows into a spacious living area with a gas fireplace, built-in bookcases, and a light-filled dining room. The principal suite offers serenity and calming vistas, while the second floor includes three bedrooms with private baths and a cozy family room with a fireplace. The walk-out lower level provides additional finished space and a full bath. Outdoors, a heated salt water gunite pool and elegant hardscaping create a luxurious retreat. With preferred gas heat, central AC, and an attached two-car garage, this nearly 2-acre property is a rare gem in coveted East Orleans. Tax assessment is for the lot only.

Listed by Peg LoPresto of William Raveis Real Estate & Home Services

Buyers Brokers of Cape Cod, McKenna Associates
116 Route 6A
Sandwich MA, 02563
Office: 774-994-1900

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Your Questions & Comments I have a question about the property at 44 Tonset Road Orleans MA 02653 (#22404490).

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MLS Number 22500360

• Residential
• Bedrooms 4
• Bathroom 3
• Square Feet 3,250

Welcome to 6 Snow Way, a stunning private waterfront estate in East Orleans, where sophisticated coastal living harmonizes with the serene beauty of Rachel's Cove. This exquisite home, perched majestically on a hill, offers breathtaking water views, extensive waterfront, is strategically positioned outside the flood zone, and features a gently rolling landscape that gracefully descends to the water's edge. This four-bedroom, three-bathroom residence presents an inviting living space designed to embrace the tranquility of its surroundings. The charming kitchen, perfect for culinary adventures, seamlessly blends into the dining and living areas, creating an ideal environment for entertaining. Step outside to savor the porch or enjoy a peaceful stroll along the winding path through the wooded landscape to the waterfront, offering a true escape into nature. Beyond its picturesque setting, the property includes 12 Snow Way, a 1.85-acre lot, providing opportunities for potential expansion, whether for a guest house, pool house, or the creation of a family estate. With a 2 car garage, ample parking, and a design that pairs convenience with timeless coastal elegance, this exceptional Orleans estate offers both privacy and tranquility in an unparalleled setting.

Listed by Diana S Lucivero and Patricia M Pierce of Compass Massachusetts,LLC

Buyers Brokers of Cape Cod, McKenna Associates
116 Route 6A
Sandwich MA, 02563
Office: 774-994-1900

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MLS Number 22500354

• Residential
• Bedrooms 4
• Bathroom 4
• Square Feet 3,630
• Parking Spaces 8

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. Upon entering, you'll be instantly impressed by the welcoming foyer, its raised-panel wainscoting, and the warm, maple flooring which continues throughout the main living area. Transom windows maximize the natural light and add a touch of historic architectural charm, as do the cedar shake roof shingles, built-ins, and colonial brick fireplaces found in both the living room and home office. The four generously sized bedrooms and three full baths offer flexible configurations to accommodate a variety of living needs, including a first-floor en-suite, choice of two second-floor en-suites, and separate entrance and staircase access to one en-suite if desired. This home is PERFECT for outdoor entertaining with its two low-maintenance decks overlooking the large, private backyard which slopes gently down to the water, where you can launch your kayak or paddleboard. Other features include a 2-car garage, irrigation, outdoor shower, ... invisible fence, first-floor laundry room with sink, and storage galore, including a walk-in cedar closet. Bring your designer and imagine how your updates can make this quality-built waterfront home your Cape Cod dream oasis!

Listed by Sarah E Gammons - Ciampa and Marie Kelly of Berkshire Hathaway HomeServices Robert Paul Properties

Buyers Brokers of Cape Cod, McKenna Associates
116 Route 6A
Sandwich MA, 02563
Office: 774-994-1900

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Your Questions & Comments I have a question about the property at 46 Freeman Lane Orleans MA 02653 (#22500354).

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MLS Number 22403514

• Residential
• Bedrooms 4
• Bathroom 5
• Square Feet 3,706

This classic salt-waterfront cape directly overlooking Town Cove enjoys its own private sandy beach and boating access to Nauset Spit and beyond. West-facing on an elevated acre with room for a pool, this architecturally traditional home with a modern floorplan provides a singular blend of spectacular sunset views, casually elegant comfort and privacy. Superb water views from nearly every room, the large waterside lawn and the first and second floor decks that span the entire rear of the house. The main floor encompasses the fireplaced living room, sitting area, updated kitchen, dining space, laundry and the stylish primary bedroom suite with dressing room and luxury bath. Upstairs are a family room and three bedroom suites, all with updated baths. Numerous upgrades to the home's major systems. A recent gas conversion includes the kitchen, HVAC, a new generator and gas grill. The walkout basement is great for transporting kayaks and beach chairs down the gently sloping path to the private, sandy beach. Swim or clam, fish or sunbathe or take the boat from your mooring to the resident's side of Nauset Beach. A generational family home for the consummate Orleans seaside experience.

Listed by Jeffrey E Cusack of Cove Road Real Estate

Buyers Brokers of Cape Cod, McKenna Associates
116 Route 6A
Sandwich MA, 02563
Office: 774-994-1900

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Your Questions & Comments I have a question about the property at 15 Salt Works Circle Orleans MA 02653 (#22403514).

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MLS Number 22501827

• Residential
• Bedrooms 3
• Bathroom 3
• Square Feet 2,756
• Parking Spaces 6

Elevated above the serene waters of Town Cove and adjacent to Asa's Landing, this Orleans property presents the opportunity to create a legacy estate in one of the Cape's most coveted neighborhoods with a home and additional land on Gibson Rd. The gracious 3-bedroom home is thoughtfully sited to offer unobstructed water views from every room, providing a backdrop of unparalleled natural beauty. Complemented by a boat house, two-car garage, and a barn, this property exudes charm and character, with ample space for storage or transformation. Accompanying the sale is a separate buildable waterfront lot at 60 Gibson Road, offering endless possibilities. Whether you envision a luxurious guest home, a private family retreat, or a multi-generational compound, this unique property allows you to craft a vision that meets your dreams.This is a rare and truly one of a kind offering--designed for those who seek elegance, privacy, and the timeless beauty of waterfront living. Moorings are available in front with approval from the harbormaster.

Listed by Dawn Lee of Gibson Sotheby's International Realty

Buyers Brokers of Cape Cod, McKenna Associates
116 Route 6A
Sandwich MA, 02563
Office: 774-994-1900

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Your Questions & Comments I have a question about the property at 4 Asas Landing Orleans MA 02653 (#22501827).

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