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$4,499,000
8 Beds ⋅ 9 Baths ⋅ 73377530 MLS
Nestled in the heart of the West End, this historic 1847 Greek Revival Captain's Home is now available for purchase after 29 years under the same ownership. As one of the largest buildings in the neighborhood, the West End Inn serves primarily as a private residence but is also licensed as a B&B. The first floor was completely renovated in 2019. The property features three kitchens, a kitchenette, and four separate living quarters, each with private entrances. The light-filled, three-family layout offers potential to be converted into a substantial single-family home. There are nine bathrooms, eight bedrooms, two dens, two decks, two private garden spaces, and a beautifully appointed front yard. The top floor, with its large deck, provides water views and unobstructed vistas of Telegraph Hill and stunning sunsets. Parking is available for five or more cars, and beach access is directly across the street. Betterment paid in full.

44 Commercial Street, Provincetown

Listing courtesy of Listing Agent: Iskren Georgiev from Listing Office: Gibson Sotheby's International Realty.
$2,700,000
7 Beds ⋅ 7 Baths ⋅ 73373131 MLS
For the first time in generations, this landmark Pleasant Bay compound—anchored by the iconic "Topside" main residence and the charming two-bedroom "Boathouse"—is offered as a rare, generational waterfront estate, a site long cherished by those who have called it home. 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. Both homes enjoy sweeping 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. Thoughtfully sited by its original architect to capture the light and water at every turn, "Topside" offers 5 bedrooms and 4.5 baths with timeless coastal character and spaces designed for gathering, while the "Boathouse" sits just above the shoreline, featuring 2 bedrooms, 1 bathroom, and its own deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn offer a blend of intimacy and scale. With a strong rental history and potential for expansion or personalization, this is a lifestyle property that invites multigenerational living, savvy investment, or a private retreat. A once-in-a-lifetime opportunity to own one of Cape Cod's most storied, landmark waterfront settings.

645 S Orleans, Orleans

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$12,250,000
5 Beds ⋅ 6 Baths ⋅ 73342640 MLS
Exquisite Waterfront Estate in Exclusive Oyster Harbors: Experience the pinnacle of coastal luxury with this magnificent Cape Cod waterfront estate, nestled in the prestigious gated community of Oyster Harbors. Boasting 450 feet of pristine water frontage with a private beach and breathtaking views over Cotuit Bay and North Bay, this property offers spectacular sunsets, an elegant coastal lifestyle, and unparalleled privacy. Stepping into the grand foyer, you are greeted by vaulted ceilings and expansive windows that showcase panoramic water views, seamlessly blending the outdoors with the refined interiors. The open-concept living spaces include a gracious living room, a fireplace-warmed dining room with custom built-ins, and a sophisticated sitting area, all designed for effortless entertaining. A private home library, accessed by a spiral staircase, overlooks both the main level and the serene waters of North Bay. The gourmet chef's kitchen is a masterpiece, featuring a granite center island, custom built-ins, and a charming breakfast nook with wraparound picture windows framing the breathtaking waterfront vistas. The sumptuous first-floor primary suite is a sanctuary of relaxation, offering private patio access, a spacious walk-in closet, and a spa-inspired en-suite with dual vanities, a luxurious soaking tub, and a glassless double-headed rain shower. The sun-drenched sunroom complete with a full wet bar and sliders on three sides opens directly to the meticulously designed outdoor living areas. The second level hosts four additional spacious bedrooms, a generous family room, and a bonus room with a private balcony, designed for both comfort and relaxation. This exceptional residence also features a partially finished lower level, thoughtfully designed to enhance both convenience and functionality with direct outdoor access perfect for accommodating small boats, golf carts and other recreational essentials. Set on 1.37 acres of pristine coastal land, this estate is an outdoor enthusiast's paradise. The meticulously landscaped grounds feature a built-in fire pit, an outdoor shower, a waterside in-ground pool, a sandy beach, and a private dock. A rare opportunity to own a world-class waterfront residence, this home delivers unparalleled elegance, modern luxuries, and the very best of Cape Cod's coastal living.

71 Sand Pt, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .
$3,999,000
5 Beds ⋅ 9 Baths ⋅ 73322653 MLS
Discover the epitome of luxury at this exquisite waterfront estate, a haven of tranquility and elegance. Built in 2002 and meticulously renovated, this stunning home offers unmatched comfort and privacy on 4.32 acres. With prime waterfront access and breathtaking views, this expansive 16-room residence features 5 spacious bedrooms and 9 baths including steam shower. The interior boasts two elegant primary suites with gas fireplaces, expansive walk-in closets, and deep hydro-massaging tubs. The masterfully crafted kitchen is equipped with top-line appliances, custom cabinets and granite countertops. The lower level includes hobby and pool table rooms, a kitchenette, an entertainment center and substantial storage. Outdoors, enjoy a stunning heated saltwater pool, oversized hot tub, waterfalls, multilevel stone terrace, outdoor shower, cabana with full bath and a built-in cooking area.This waterfront estate is more than just a home; it's a lifestyle.

26 Walkerwoods Dr, Harwich

Listing courtesy of Listing Agent: Karen Lopez from Listing Office: Great Estates Realty, Inc..
$9,950,000
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: .

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