Timothy Levesque

White Sands Beach Club is a rare beachfront redevelopment opportunity located on 2.30 acres at Beach Point, immediately south of the Provincetown town line.The property is being offered under two separate purchase options:Buildings 2, 3 and 4 may be purchased together for $22,999,000. This offering includes 42 fee-simple condominium units totaling approximately 20,285 square feet.Buildings 3 and 4 may be purchased without Building 2 for $14,999,000. This offering includes 25 fee-simple condominium units totaling approximately 12,885 square feet.Building 1, containing the owner’s residence and staff apartment, is retained by the Seller and is excluded from both purchase options.The campus already operates under an established condominium structure. Approximately 40% of the units have been rebuilt from the ground up since 2019, with additional units substantially renovated. Building 4 remains largely original and represents the principal value-add component of the property. Potential strategies include phased condominium redevelopment, multifamily use or continued seasonal lodging, subject to all required approvals.

706 Shore Rd Unit 706, Truro

Listing courtesy of Listing Agent: Kevin A. Pepe from Listing Office: Commercial Realty Advisors, Inc..

$22,500,000

4 Beds ⋅ 4 Baths ⋅ 73582414 MLS

An exceptional East Dennis estate spanning nearly 22 private acres, this extraordinary waterfront property offers a rare combination of scale, seclusion, and breathtaking coastal beauty. Beyond a gated entrance, a long, bucolic drive unfolds to a magnificent setting, bordered by protected conservation land and overlooking sweeping vistas of Cape Cod Bay. With 200 feet of private beach, the property enjoys a level of privacy and direct waterfront access rarely found on Cape Cod. The four-bedroom main residence captures the beauty of its surroundings with stunning water views, while a detached barn adds versatility and character to the estate. Perhaps most remarkable is the potential for an additional substantial residence, offering the rare ability to create a true multigenerational compound. With nearly 22 acres of private waterfront land virtually impossible to replicate in East Dennis, this is a finite opportunity to own one of Cape Cod's most impressive coastal estates.

102 Sesuit Neck Rd, Dennis

Listing courtesy of Listing Agent: Paul McCormick from Listing Office: Gibson Sotheby's International Realty.

$18,500,000

7 Beds ⋅ 11 Baths ⋅ 73563501 MLS

Exquisite waterfront estate in the gated enclave of Oyster Harbors, one of Cape Cod's most sought-after communities. Located minutes from everything Osterville has to offer, yet a world apart, the property represents a rare and extraordinary opportunity to own a generational compound in an inimitable setting. Ideally positioned to capture dramatic sunsets over Cotuit Bay and Nantucket Sound beyond, the estate features a stunning main residence, a two-bedroom guest cottage, a swimming pool, private dock, and beach. A wooded drive gives way to manicured grounds of nearly two acres, transporting one to a private seaside resort as the ocean comes into view. Inside, an open layout caters to modern living with an eat-in chef's kitchen equipped with professional-grade appliances, seamlessly blending with a fireplaced living area. Oversized windows and glass doors line the waterside of the home, framing spectacular vistas and effortlessly connecting to the outdoors where a covered wooden deck invites al fresco dining and entertaining. Elevated quality and craftsmanship are found throughout, from rich hardwood floors to custom built-ins and crown moldings.The expansive primary suite encompasses an entire wing of the home with a private balcony overlooking the water, a sumptuous bathroom with a built-in soaking tub, and two walk-in closets. Four well-appointed en suite bedrooms complete the second level, offering refined accommodations for family and friends. Designed to embrace outdoor living, the resort-inspired pool and terrace are the perfect gathering place for summer days, complete with an outdoor kitchen and cabana. A rolling lawn leads to the water, where the private dock offers endless possibilities for days spent on the ocean. Additional highlights include a sports court and a car barn that's sure to please the discerning automotive enthusiast. A rare combination of luxury, privacy, and natural beauty, this one-of-a-kind estate is ready to be enjoyed.

47 Sunset Point, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$17,500,000

3 Beds ⋅ 2 Baths ⋅ 73559053 MLS

This remarkable 5+ acre waterfront estate is one of the most extraordinary coastal offerings to come to market in generations. Perched on the southwest tip of an exclusive community, it is Cape Cod's southernmost private residential land. The property commands panoramic, unobstructed views across Buzzards Bay to Naushon and the Elizabeth Islands, and then onto Vineyard Sound and Martha's Vineyard. The estate features more than 611 feet of shoreline, anchored by a substantial protective seawall that ensures both privacy and structural permanence, as well as a private, pristine sandy beach. A charming three-bedroom cottage currently rests on the grounds, offering immediate enjoyment while serving as an unparalleled canvas for a world-class waterfront masterpiece. Future development allows for a two-story residence designed to capture expanded views toward Great Harbor, subject to local approvals.

187 Penzance Rd Unit Lot 1C, Falmouth

Listing courtesy of Listing Agent: Kerrie Marzot from Listing Office: Sotheby's International Realty.

$16,500,000

8 Beds ⋅ 11 Baths ⋅ 73586293 MLS

Set along the soothing waters of West Bay, this exceptional waterfront estate, with approx. 400' of waterfront, captures magnificent western exposure, offering ever-changing views of boats navigating to and from the harbor and spectacular evening sunsets dancing across the water. This 'Wianno Head' area is one of the most coveted areas of Osterville with large, private estate settings. This property also benefits from protected conservation 'Land Trust' land directly across from its gated entrance to the property. The main residence encompasses warm, luxurious living spaces, distinguished by extensive custom millwork, custom stone, tile and brick work, and refined architectural details throughout. The gourmet kitchen and butler's pantry are designed to delight, while the grand living room and adjoining dining room provide an elegant setting for entertaining. A sunroom overlooks the water, while the inviting family room and adjacent dining area create comfortable spaces for everyday living. The residence offers a 1st floor bedroom suite, and the 2nd floor provides three bedroom suites and a glorious master suite with his-and-her bathrooms and dressing rooms, a private sitting room, and a deck with exceptional water views. The third floor features an additional bedroom and bath, a family room, and a charming widow's walk overlooking the surrounding landscape and bay. A finished lower level provides additional flexible living and recreational space. A separate two-bedroom, two-bath carriage house offers a full kitchen and living room, providing an ideal private retreat for guests and extended family. Encompassing three acres of beautifully landscaped, park-like grounds, that are irrigated by a private well, the property offers an extraordinary sense of privacy. Manicured lawns and gracious mature trees frame an inviting PebbleTech-finish pool, an expansive terrace, perfectly suited for outdoor entertaining and enjoying unforgettable sunsets. Steps lead down to the water's edge, where a private sitting area provides a peaceful place to take in the views. A permanent deep-water dock on West Bay complete this remarkable waterfront setting. The prestigious Wianno Club and Oyster Harbors Club, as well as Nauticus Yacht Club, Crosby Boatyard, and the numerous shops and restaurants in the village, are only minutes away. All information stated here in or verbally stated, should be verified by the Buyer(s) and their representatives.

143 Bayberry Way, Barnstable

Listing courtesy of Listing Agent: John Hopkins from Listing Office: Frank Sullivan Real Estate, LLC.

$16,000,000

7 Beds ⋅ 13 Baths ⋅ 73584008 MLS

Privately set behind a gated drive on two acres along Eel River, this remarkable Osterville waterfront estate commands a rare vantage point overlooking the river and Nantucket Sound. The architecture is designed around the setting, with broad expanses of glass, soaring coffered ceilings, fine millwork, and a succession of light-filled spaces oriented toward the water. The main level brings together a gracious chef’s kitchen, a dramatic great room overlooking the water, and a luxurious primary suite with its own media room. The residence unfolds across three levels, with a graceful stairway connecting each floor. The second level offers three additional bedroom suites, while the third floor creates a more intimate retreat, with a spacious waterfront sitting room opening to a private balcony, and a fifth bedroom along with two bonus rooms. The finished lower level is dedicated to recreation, with a theater accommodating 20 and a substantial game and media room. Beyond the main residence, the property takes on the character of a private coastal compound. A separate two-bedroom guest house with three-car garage and pool house overlooks the expansive pool and surrounding grounds. Multiple terraces and outdoor rooms lead toward the water, where a private sandy beach and substantial deep-water dock provide direct access to Eel River and Nantucket Sound. The setting is quintessentially Osterville: private, deeply connected to the water, and minutes from the village, its beaches, harbor, shops, and restaurants. With its scale, architectural pedigree, guest accommodations, and exceptional boating access, this is a distinctive waterfront offering in one of Cape Cod’s most sought-after enclaves. 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.

74 Garrison Ln, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$15,850,000

8 Beds ⋅ 9 Baths ⋅ 73585729 MLS

Set on 2.35 beautifully landscaped acres along Eel River, this exceptional Osterville waterfront estate enjoys western exposure, sweeping water views, and a substantial deep-water dock with direct access to Nantucket Sound. The setting is defined by an extraordinary combination of privacy, scale, and waterfront amenities, creating a rare sense of arrival and an exceptional connection to the water. The six-bedroom main residence offers approximately 7,000 square feet of living space, with a gracious floor plan designed to take full advantage of the setting. From the grand foyer, panoramic water views immediately draw the eye through the home and toward the expansive grounds and waterfront beyond. The main level offers generous living and entertaining spaces, while the second floor features a spacious primary suite with fireplace, walk-in closet, and private bath, along with five additional bedrooms. The lower level includes a recreation room, exercise room, and abundant storage, with an attached two-car garage. The waterfront grounds are the centerpiece of the property. An expansive pool, glass-enclosed pool house, and substantial deep-water dock create an exceptional setting for summer living, boating, and entertaining. The western exposure brings beautiful afternoon and evening light across the water, while the location provides direct access to Nantucket Sound. A separate two-bedroom carriage house with attached two-car garage and private patio provides comfortable accommodations for guests and extended family. Osterville Village, with its high-end shops and refined dining, is close at hand, as are the area’s renowned golf clubs. With its extraordinary acreage, western water views, deep-water access, pool, guest accommodations, and exceptional privacy, this is a waterfront estate of uncommon scale and presence. 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.

141 Eel River Rd, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$13,900,000

7 Beds ⋅ 10 Baths ⋅ 73580848 MLS

Set along the shores of historic Bass River, this extraordinary waterfront estate captures the rare combination of deep-water boating, exceptional privacy, and sweeping views toward Nantucket Sound. Set on .84 acres, the property offers 134 feet of private deep-water dockage, a private sandy beach, and direct access to one of Cape Cod's most distinctive waterways, where the river opens to Nantucket Sound. In addition to its own private beach and deep-water dock, the property also enjoys access to an association beach and secondary deep-water dock. An inground Gunite pool, oversized hot tub, and three-car attached garage complete an exceptional waterfront setting. Designed to embrace its spectacular waterfront setting, the residence is distinguished by beautiful architectural details, refined finishes, and exceptional craftsmanship throughout. The open floor plan features coffered ceilings and an abundance of waterside doors with transom windows, bringing natural light and the beauty of the river into the living spaces. The main level centers around an exceptional chef's kitchen with generous seating and top-of-the-line appliances, while elegant formal and informal spaces flow naturally to the waterside pool and entertaining areas. A luxurious first floor primary suite with a walk-in closet and beautifully appointed bathroom embrace the water views, while a second bedroom suite and home office complete the first floor. The second-floor features three waterside suites with private balconies and beautiful water views, along with two additional en-suite bedrooms and a generous media/game room. The third floor is designed for entertaining, with two bonus rooms and a full bar uniquely crafted in the style of a classic boat. Outside, the waterfront setting is designed for effortless summer living, with a Gunite pool, oversized hot tub, built-in grill, gas fire pits, and multiple seating areas overlooking the river. The grounds are beautifully landscaped and thoughtfully designed to create a sense of privacy, with mature natural screening surrounding the property. With its deep-water dock and boat lift, private beach, expansive river views, and easy access to Nantucket Sound, this remarkable estate offers a rare opportunity to experience Bass River at its finest—where Cape Cod's rich maritime heritage meets sophisticated contemporary waterfront living.

28 Aunt Ediths Rd, Yarmouth

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$12,900,000

6 Beds ⋅ 10 Baths ⋅ 73560074 MLS

12 Foxcroft Lane | East SandwichA once-in-a-generation waterfront estate, 12 Foxcroft Lane represents the pinnacle of Cape Cod coastal luxury. Set on beautifully manicured grounds with sweeping lawns, a pristine private sandy beach, and panoramic views of Cape Cod Bay from Plymouth to Provincetown, this extraordinary 16,000± sq. ft. residence offers six bedrooms and ten baths designed for generations to enjoy.Light-filled living spaces flow seamlessly to exceptional outdoor entertaining areas, while the chef's kitchen opens to an inviting family room anchored by a magnificent stone fireplace - the heart of the home, where stories are shared, celebrations unfold, and a lifetime of memories begin. The luxurious first-floor primary suite is a private retreat with breathtaking views. World-class amenities include a private theater, professional fitness center, resort-style infinity pool, poolside cabana, putting green, and a private boardwalk leading directly to the beach.More than a home,12 Foxcroft Lane is a legacy estate--an irreplaceable waterfront sanctuary offering unmatched privacy, extraordinary craftsmanship, and one of the finest beachfront settings on the Eastern Seaboard

12 Foxcroft Ln, Sandwich

Listing courtesy of Listing Agent: Michael Harney from Listing Office: Sotheby's International Realty.

$12,250,000

7 Beds ⋅ 9 Baths ⋅ 73551533 MLS

Perched within ''The Cliffs''--West Falmouth's most coveted private seaside enclave--this custom shingle-style estate offers over 11,000 square feet of exquisitely finished living space in pristine condition with multiple family suites. From its elevated vantage overlooking Buzzards Bay, the residence commands panoramic water views toward the Elizabeth Islands and Vineyard Sound--permanently protected by a perpetual view easement, ensuring unobstructed western sunsets for generations. An opulent foyer with sweeping curved staircase opens to soaring volumes, rich hardwoods, and custom millwork throughout. Seven bedrooms, eight full and one half baths are arranged for privacy, while a formal dining room and multiple living areas open through French doors to landscaped grounds and four expansive decks. Recent improvements include a new roof and whole-house generator. Residents enjoy The Cliffs' private sandy association beach, minutes from West Falmouth Harbor, yacht clubs, golf, and the Shining Sea Bikeway.

39 Naushon S, Falmouth

Listing courtesy of Listing Agent: Diana Lucivero from Listing Office: Compass.

$12,000,000

73526763 MLS

Beach Point Development Site — first time offered for development on the shores of Cape Cod Bay. This rare waterfront opportunity currently operates as a 26-unit motel and presents exceptional potential for redevelopment into a luxury Beach Club, resort destination, or condominium conversion.The property benefits from significant beach accretion, expanding to approximately 3.37 acres and enhancing both value and future development possibilities. With direct bayfront appeal, sweeping coastal surroundings, and strong investment upside, this is a premier opportunity to create a landmark destination on Cape Cod.Bring your vision to life with the support of an experienced owner and Realtor team ready to assist in transforming this profitable property into its next chapter.

654 Shore Road, Truro

Listing courtesy of Listing Agent: Team Brown from Listing Office: Thomas D. Brown RE Associates.

$11,500,000

6 Beds ⋅ 8 Baths ⋅ 73531287 MLS

Newly constructed and ready to enjoy, this exceptional waterfront estate on the Bumps River represents the finest of Cape Cod living. Combining an unrivaled setting with state-of-the-art luxury, the property features a resort-like swimming pool and cabana, a boathouse with a float for non-motorized crafts, and a deeded beach lot on Long Beach. The open floor plan seamlessly flows from a fireplaced living room with coffered ceilings to a gourmet kitchen with a Sub-Zero refrigerator, Wolf range, and Danby natural stone counters. Glass doors line the waterside of the home, opening to an expansive Phoenician Buff stone terrace surrounding a Pebble Tec pool and spa. The first-floor primary boasts 2 walk-in closets and a luxurious bath with a freestanding soaking tub. Four en suite bedrooms, a family room, and an ipe deck occupy the second level, with bonus space above. A bedroom suite over the garage accommodates guests or staff. Located minutes from everything Osterville has to offer.

48 Starboard Lane, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$11,495,000

5 Beds ⋅ 4 Baths ⋅ 73537406 MLS

Tracing its roots to a classic Cape house and fishing shack in Provincetown's historic West End, this remarkable waterfront residence was elevated and transformed through an extensive restoration that preserved its authentic architectural character while reimagining the property for a new generation. Structural pilings and timbers salvaged from Boston's famed Jimmy's Harborside Restaurant were masterfully incorporated into the staircase and ceiling details. Rich pine floors, a rugged fieldstone fireplace, a custom Vermont marble kitchen with a soapstone island, a generous pantry, a waterfront dining room, and a harbor-facing sitting room define the interior layout. A rare and defining feature is the property's extraordinary private dock--the largest associated with any single-family residence in Provincetown--extending approximately 70 feet into the harbor and providing an unparalleled connection to the waterfront.

71 Commercial Street, Provincetown

Listing courtesy of Listing Agent: Iskren Georgiev from Listing Office: Gibson Sotheby's International Realty.

$10,300,000

4 Beds ⋅ 5 Baths ⋅ 73586679 MLS

Spectacular new construction on Buzzards Bay in coveted West Falmouth. Privately set on 4.5 acres at the end of a long drive, this exceptional waterfront residence offers 350’ of private, soft white sandy beach and breathtaking 180° west-facing views with unforgettable sunsets. Quality built by a respected local builder, the home is elevated and constructed to today’s flood standards. Featuring 4 bedrooms, 4.5 baths, elevator and 2-car garage. A gorgeous chef’s kitchen with generous island opens to a dramatic great room with soaring ceilings. Expansive windows capture stunning water views from nearly every room. The beach is protected by jetties and adjacent to Little Island Beach and preserve. An extraordinary private coastal setting close to West Falmouth Harbor, Shining Sea Bikeway and West Falmouth Tennis Club. A rare combination of new construction, acreage, privacy and exceptional beachfront.

114 Quaker Rd, Falmouth

Listing courtesy of Listing Agent: O'Neill Group from Listing Office: .

$9,850,000

5 Beds ⋅ 5 Baths ⋅ 73395925 MLS

Legacy, Lifestyle & Opportunity - A discreet treasure in one of Cape Cod's most prestigious enclaves, this exceptional waterfront property offers rare access to legacy, lifestyle, and limitless potential. Originally part of a historic compound long held by the Mellon family and now by noted philanthropist and collector William Koch, the property stands as a rare opportunity to own a slice of coastal legacy. This waterfront estate offers 1.78 acres of private grounds, a beautifully preserved five-bedroom residence, and a substantial deep-water dock with direct access to Nantucket Sound—accommodating six or more vessels with ease. Inside, the home exudes understated charm with a seamless connection to outdoor living—screened porch, expansive deck, and water views from most rooms. A welcoming main-level primary suite with adjoining study anchors the floor plan, while the heart of the home features a stone fireplace, an open-concept kitchen, and a screened porch that opens to an expansive deck—perfect for entertaining or quiet reflection. Upstairs, guest bedrooms are enhanced by gracious proportions and stunning vistas. With additional buildable parcels from the same legacy estate also available, this is a rare opportunity to establish a private compound in one of New England's most exclusive waterfront enclaves. A sanctuary of coastal beauty and historic significance, all within the beloved village of Osterville - home to world-class golf, protected waters, and the timeless allure of Cape Cod. 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.

14 Indian Trail, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$9,495,000

3 Beds ⋅ 3 Baths ⋅ 73594589 MLS

Sparkling harbor views, afternoons by the pool, and expansive, private grounds on coveted Shore Road. Offered for the first time since 1987, "Offshore" encompasses more than an acre - a rare opportunity to enjoy a remarkably private estate-like setting in the heart of Chatham. Beyond the house, a surprising expanse of lawn and gardens unfolds, its scale and privacy revealed only when you explore the grounds. Inside, gracious, generously proportioned rooms and timeless Cape Cod character create an inviting setting for entertaining, gathering with friends, or savoring a quiet afternoon. Views of Chatham Harbor, North Beach, and the Atlantic provide a lovely backdrop from the main living areas, while upstairs windows frame picture-perfect coastal scenes. A spacious first-floor primary suite offers comfort and ease. A carriage-style garage completes the property, just moments from Chatham Bars Inn, the Fish Pier, Lighthouse Beach, and Main Street. Whether enjoyed as it is today or thoughtfully reimagined, this special property invites its next owner to create a lasting legacy along one of Chatham's most iconic streets.

153 Shore Rd, Chatham

Listing courtesy of Listing Agent: Sarah Keith from Listing Office: eXp Realty LLC.

$8,995,000

6 Beds ⋅ 9 Baths ⋅ 73581579 MLS

Presiding over West Bay, this extraordinary waterfront estate spans 2.35 pristine acres with breathtaking views in an unrivaled location. A park-like driveway winds through manicured grounds with sculpted boxwood hedges and vibrant hydrangeas, creating a sense of privacy and grandeur as you approach the residence. A private dock provides immediate access to West Bay and Nantucket Sound, while the waterside swimming pool and pool house create a resort-like atmosphere. Inside, the residence showcases fine architectural millwork, soaring ceilings, limestone flooring, and six fireplaces across its gracious living spaces. The intuitive layout centers around an impressive main living room where French doors trace the water side of the home, allowing natural light to pour inside while framing panoramic views. Cooking and daily living center around the gourmet kitchen, which features a custom wood center island with seating, professional-grade appliances, and natural stone countertops. Exceptional quality and attention to detail are evidenced throughout, from the oval wood-paneled library with built-in bookshelves to the industrial-grade HVAC system ensuring the utmost comfort. Six well-appointed en suite bedrooms provide exceptional accommodations for all, including a luxurious primary suite with two full bathrooms, two dressing rooms, and serene views of the water. Outside, an expansive stone patio surrounds the swimming pool and spa, providing an effortless setting for al fresco dining and entertaining amidst a stunning backdrop. Combining refined craftsmanship and modern luxury in one of Cape Cod's most coveted neighborhoods, this inimitable waterfront estate is located minutes from Wianno, Oyster Harbors, Main Street, and everything Osterville has to offer.

204 Garrison Lane, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$8,950,000

6 Beds ⋅ 9 Baths ⋅ 73285680 MLS

Discover the epitome of luxury living in this custom-designed waterfront estate, featuring breathtaking views of Eel River and Nantucket Sound. Located in the village of Osterville and set on an expansive and beautifully landscaped 2.4-acre lot, this stunning residence features over 8,000 square feet of meticulously crafted living space with rich details, modern comforts and extraordinary views. The grand interiors seamlessly blend with the exquisitely landscaped outdoor spaces, featuring an inground pool, hot tub, spacious pool house, and a substantial private deep-water dock. Upon entering the home, the grand foyer leads you into the magnificent great room with a two-story custom fireplace, where panoramic vistas of the water and breathtaking sunsets set the scene for unforgettable family gatherings as well as effortless entertaining. The generous floor plan also features a refined library, formal dining room, a gourmet kitchen with center island, custom cabinetry and top-of-the-line appliances and a state-of-the-art home theatre. The six en-suite bedrooms include a first-floor suite with French doors leading to the back yard and a lavish primary suite with a luxurious bathroom, two walk-in closets and a private deck overlooking the water. Enhanced with modern conveniences such as a Sonos whole-house sound system and a 9-zone Hydro air system, every detail has been carefully planned and implemented. Additional highlights include a private guest suite above the attached 3-car garage and a sprawling entertainment room with a balcony on the third level highlighted by western exposure to experience breathtaking sunsets. Located just minutes from the upscale boutiques and renowned dining of Osterville village, this extraordinary property offers a lifestyle of unparalleled elegance and tranquility by the sea. 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.

501 Eel River Rd, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$8,800,000

5 Beds ⋅ 6 Baths ⋅ 73544944 MLS

Set behind the gates of Oyster Harbors, Cape Cod's most exclusive private golf and waterfront community, this extraordinary waterfront estate offers an exceptional blend of architectural elegance, privacy, and coastal luxury. Perfectly sited on 1.65 acres along the water's edge, the property enjoys sweeping water views, a deep-water dock, an in-ground pool, and meticulously landscaped grounds designed for both grand entertaining and quiet moments of retreat. Inspired by the timeless character of a European country estate, the residence encompasses 7,157 square feet of thoughtfully designed living space where sophisticated craftsmanship meets effortless comfort. A dramatic foyer introduces the home's remarkable interior, opening to an impressive great room with soaring vaulted ceilings, architectural columns, a custom fireplace, and expansive walls of glass that frame the ever-changing waterfront. Designed for both everyday living and elegant entertaining, the sun-filled dining room captures tranquil water views and flows seamlessly into a beautifully appointed chef's kitchen featuring a coffered ceiling, granite countertops, an oversized center island, and direct access to a spacious waterside terrace. The first-floor primary suite offers a luxurious private retreat, while four additional bedrooms--including a gracious guest suite above the attached three-car garage--provide exceptional accommodations for family and guests. Outdoor living is equally compelling. Expansive terraces and inviting gathering spaces overlook the pool, manicured gardens, and deep-water dock, creating an idyllic setting for waterfront entertaining or peaceful afternoons by the shore. Set within one of Cape Cod's most coveted private enclaves, where golf, boating, and an unmatched sense of privacy define the lifestyle, this exceptional estate represents a rare opportunity to own a legacy property in Oyster Harbors. 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.

25 Oyster Way, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$8,625,000

7 Beds ⋅ 8 Baths ⋅ 73543017 MLS

Legacy estate set prominently on one of the highest Osterville bluffs delivers classic waterfront expectations with a superior dock and substantial dynamic views from the Vineyard to Hyannisport. The grand yesteryear home constructed in 1920 conveys the qualities of that oceanfront era, with higher ceilings, multiple great rooms, and the character of hidden porches, exclusive balconies, and romantic patios. Curving stone walls, terraced rock feature gardens, and stone patios complement the entire grounds. Across the river from your 200 feet of waterfront is Long Beach, a pristine barrier stretch of powdery white sand and privacy. The dock enjoys some of the deepest water of any house on this stretch, allowing for multiple boats and other recreational craft. The quaint conclusion to this fairytale setting is a larger detached apartment over the garage. The square footage of 9,011, seven bedrooms and seven-and-a-half bathrooms speak for themselves. This treasure is waiting for you.

63 Main Street, Barnstable

Listing courtesy of Listing Agent: Christa Zevitas from Listing Office: .

$7,995,000

9 Beds ⋅ 8 Baths ⋅ 73590614 MLS

Privately set on 1.95 beautifully landscaped acres in the coveted Gansett neighborhood of Woods Hole, this distinguished 1930 Colonial estate captures the essence of refined Cape Cod living. Days unfold between the heated saltwater pool, expansive lawns, private association beach overlooking Quissett Harbor, and deeded access to Little Gansett Beach, while the restaurants, cafés, waterfront, and village life of Woods Hole are nearby. Rich in architectural character and thoughtfully expanded over time, the property offers an exceptional combination of privacy, gracious entertaining spaces, and effortless access to the water. Offering more than 8,500 square feet of living space, nine bedrooms, seven full baths, and one half bath, the residence provides remarkable flexibility for family and guests. At the heart of the main house is a chef's kitchen appointed with a Wolf range and Sub-Zero appliances, complemented by a charming breakfast nook, formal dining room with fireplace, laundry room, and mudroom. A first-floor primary suite provides gracious single-level living, while a handsome den, fire placed living room, and sunroom offer beautifully proportioned spaces for intimate gatherings and larger-scale entertaining. Upstairs, a second primary suite enjoys water views, a walk-in closet, and private bath. A second-floor library, two additional bedrooms sharing a full bath, three smaller bedrooms with another shared bath, and an original telephone closet preserve the home's distinctive character and 1930s heritage. A substantial addition creates an exceptional second living environment, anchored by a dramatic cathedral-ceiling great room with fireplace and an adjoining sitting room. A galley kitchen appointed with Gaggenau appliances, one bedroom, two baths, and a lower-level office provide exceptional flexibility for extended family and guests. This wing also includes a generous bonus family room-ideal for game nights, movie evenings, or memorable gatherings-as well as an additional room accessed from the exterior patio, offering even more versatile guest space. French doors open to a private patio and firepit, seamlessly extending the living and entertaining areas outdoors. The grounds are equally impressive, with mature professional landscaping framing the heated saltwater pool, koi pond, sweeping lawns, and multiple areas for outdoor entertaining and relaxation. Ownership includes access to a private association beach overlooking picturesque Quissett

80 Gansett Rd, Falmouth

Listing courtesy of Listing Agent: Kerrie Marzot from Listing Office: 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.

$7,499,999

4 Beds ⋅ 5 Baths ⋅ 73566967 MLS

Experience the vibrant energy of maritime life paired with the serenity of coastal living. Set within the coveted enclave of Saquatucket Bluffs with private association beach rights, this sophisticated residence has been meticulously renovated to strike a flawless balance between architectural elegance and coastal warmth. A classic front porch provides a graceful welcome, leading into a vaulted living room bathed in natural light. The layout emphasizes effortless indoor-outdoor living, with water views from nearly every room and direct access to the exterior. The main level features a dedicated office and a versatile ensuite, while the second floor serves as a sanctuary featuring dual balconies and two additional guest ensuites. The heart of the home is the chef's kitchen, outfitted with a center island, spacious pantry, and a breakfast nook designed to frame panoramic views of boats navigating the harbor. Entertaining is elevated by a dedicated bar with a wine fridge and a seamless flow to the large deck. Outside, professionally landscaped grounds host a harbor-view pool. Moments from downtown Harwich Port, this home offers a refined lifestyle and a premier waterfront connection.

18 Saquatucket Point, Harwich

Listing courtesy of Listing Agent: Sandra Tanco from Listing Office: Kinlin Grover Compass.

$7,250,000

6 Beds ⋅ 6 Baths ⋅ 73520863 MLS

This exquisite New Seabury home blends natural beauty with modern luxury. Perched to capture stunning Nantucket Sound views with a pristine sandy beach right outside, the property offers Cape Cod living at its finest. The open layout includes a gourmet kitchen with premium appliances, a quartz island, and custom cabinetry. A sunlit living room boasts soaring ceilings, a stone fireplace, and glass doors leading to an outdoor oasis. The serene primary suite features a spa-like marble bath, walk-in closet, and private deck with ocean views. The finished lower level provides flexible space for a media room, gym, or guests. Outdoors, enjoy a heated pool, bluestone patio, and lush landscaping—perfect for entertaining or unwinding. Approved permits are in place for an 1,800 sq. ft. guest house. With breathtaking views and direct beach access, this property epitomizes Cape Cod luxury.

50 Coastline Drive, Mashpee

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$7,250,000

7 Beds ⋅ 11 Baths ⋅ 73383981 MLS

Privately sited within the prestigious Oyster Harbors golf enclave, this extraordinary estate is a masterclass in architectural sophistication and resort-style living. Encompassing a 10,000-square-foot main residence, a stunning two-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. A gracious covered front porch welcomes you into a dramatic foyer, setting the tone for the refined interiors that follow. The main living spaces unfold in a thoughtfully designed layout that flows from formal living and family rooms to an elegant dining area with each space inviting connection, comfort, and celebration. At the heart of the home, the chef's kitchen is both striking and functional, anchored by dual oversized islands clad in premium granite, and accompanied by a fireside sitting room that beckons lingering conversation. Adjacent, the spectacular sunroom redefines indoor-outdoor living with a custom crafted bar and casual seating area at one end and a full second kitchen with custom built-in grill and dining area at the other, all enclosed by retractable screens for effortless seasonal enjoyment. Tucked away on the main level, the primary suite offers a private sanctuary, with its own fireplace, luxurious spa-like bath, and refined home office. The comfort and sophistication continue on the second level with four generously proportioned en-suite bedrooms and an inviting sitting room. Designed for comfort and connection, the finished lower level offers a wine cellar, media room, game room, and fitness space. This lavish interior flows effortlessly to an equally impressive exterior, where lush landscaping surrounds a resort-style pool framed by expansive lounging areas-perfect for everything from quiet afternoons to grand entertaining. Completing this offering is a beautiful two-bedroom guest house providing privacy and comfort for visiting guests. Set within a prestigious gated enclave with coveted beach and dock rights, this remarkable estate is the perfect fusion of architectural sophistication and everyday warmth - an extraordinary offering in one of Cape Cod's most prestigious settings. 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.

440 Grand Island Dr, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$7,150,000

5 Beds ⋅ 6 Baths ⋅ 73442362 MLS

At the tip of a private peninsula, this exceptional Cape Cod estate embodies the essence of elegant coastal living. Set on 1.07 acres with sweeping views of Buzzards Bay, the residence combines timeless architecture, refined craftsmanship, and every amenity for a luxurious seaside lifestyle. Built by renowned Osterville builder Polhemus Savery, the home offers five en suite bedrooms, including a first-floor primary suite and three additional bedrooms upstairs, plus a separate guest or nanny suite above the garage—ideal for extended stays. A comfortable second-floor family room provides a casual space for gathering.The light-filled, south-facing living areas are designed to capture the beauty of Buzzards Bay. With roughly 250 feet of water frontage it is ideal for swimming, launching paddle boards and kayaks. Not to be missed!

40 Point Rd, Falmouth

Listing courtesy of Listing Agent: Kerrie Marzot from Listing Office: Sotheby's International Realty.

$6,950,000

4 Beds ⋅ 7 Baths ⋅ 73594118 MLS

Set within the coveted Baxters Neck enclave, this exceptional waterfront estate home has been reimagined by architects and leading designers, with a thoughtful floorplan suited to both family living and grand entertaining. A dramatic two-story living room with a double-sided gas fireplace flows into a beautifully appointed chef’s kitchen and an expansive breakfast room with seating for 20. Walls of glass open to a private outdoor retreat featuring a heated pool, hot tub, stone patios, lush lawns and sweeping water views. A private dock on Prince Cove provides direct boating access to North Bay and Nantucket Sound beyond. Additional amenities include a luxury game room with access to outdoor decks, a media room, bunk room, indoor pool, spacious bedrooms, a dedicated home office and a three-car garage. This exceptional property is a pleasure to show, by appointment only.

396 Baxters Neck Rd, Barnstable

Listing courtesy of Listing Agent: Brian Dougherty from Listing Office: Corcoran Property Advisors.

$6,950,000

6 Beds ⋅ 8 Baths ⋅ 73571737 MLS

Situated on a bluff overlooking Prince Cove, this exceptional waterfront estate presents a rare combination of natural beauty, modern luxury, and total privacy in an unmatched setting. Meticulously designed and cared for, the property delivers Cape Cod living at its finest with a private dock, resort-style swimming pool, and extensive outdoor living spaces surrounded by water views and lush plantings. Upon approach, a winding drive gives way to manicured grounds as the stately residence comes into view. Inside, the home offers a light-filled open layout showcasing detailed millwork, custom trim, and high-end finishes throughout. The main living spaces emphasize indoor-outdoor living with floor-to-ceiling glass doors that capture breathtaking views and seamlessly open to an expansive deck overlooking the water that spans the length of the home. The eat-in chef's kitchen is ideal for entertaining on any scale with professional-grade appliances, granite countertops, and custom cabinetry. Ensuring the utmost comfort and convenience, the first-floor primary suite comprises an entire wing, complete with a wood-paneled office, two walk-in closets, a sumptuous bathroom, and direct access to the waterside deck. On the second level, three en suite bedrooms provide well-appointed accommodations for all. The walkout lower level features two additional en suite bedrooms, as well as a recreation area and fitness room. Whether spending sun-splashed days relaxing by the pool or boating from the protected waters of Prince Cove to Nantucket Sound, this exquisitely designed estate delivers an unsurpassed lifestyle in one of Cape Cod's most sought-after communities.

16 Cove Point Lane, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$6,875,000

4 Beds ⋅ 5 Baths ⋅ 73582098 MLS

Few homes command Oyster Pond like 12 Pond Street. Three soaring peaks, the center crowned in sculptural rounded copper, announce a custom Eastward Companies build of rare craftsmanship, with immediate proximity to Main Street and the beach. Inside, every room turns toward the water. The open first floor is anchored by a kitchen perched above stunning views, its custom cabinetry and large island opening to a fireplaced living and dining area that flows to the waterfront patio. Just beyond, the primary suite offers built-ins, a gas fireplace, a walk-in closet, and a spa-like bath. Hardwood, high ceilings, and exceptional millwork carry throughout. Upstairs, a vaulted family room with wet bar opens to a porch set above the water, joined by three bedrooms and two full baths. Below, a fully equipped gym and entertaining space. Outside, a full paver driveway, retaining walls, and terraced bluestone patios frame hydrangeas and lush native plantings, with a gas firepit, outdoor shower, and generator. A deeded association dock and mooring field deliver some of the finest boating and recreation on the Cape. A show house, purpose-built for entertaining and for a life lived on the water.

12 Pond St, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$6,850,000

5 Beds ⋅ 6 Baths ⋅ 73487652 MLS

Set high on a scenic bluff in New Seabury, this contemporary oceanfront estate pairs dramatic Nantucket Sound views with resort-style living. Expansive walls of glass frame the water from vaulted great rooms and intimate sitting areas alike. A sunlit gourmet kitchen opens to multiple dining spaces, while the ocean-view primary suite offers a private balcony. Highlights include a home theater, fitness room, and lower-level entertaining space with direct patio access. Outside, tiered ocean view decks, manicured lawns, and a private path with steps to the water create a seamless connection to the coast. Crafted with exceptional quality, this rare property is designed for both grand gatherings and casual living. Located minutes from New Seabury's five-star amenities, Mashpee Commons, and everything else the area has to offer!

40 Triton Way, Mashpee

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

Timothy Levesque

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