Osterville, Massachusetts listings for sale

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$12,295,000 - Osterville, MA
741 Sea View Avenue Osterville, MA - Experience the epitome of coastal luxury on a sun-drenched day, where shimmering waters create an enchanting ambiance. Nestled on over 2.3 acres along prestigious Sea View Avenue, this extraordinary Osterville estate, built in 1929, is steeped in history and charm. Step inside to discover expansive windows that showcase breathtaking views of Nantucket Sound. Step outside to enjoy 170 feet of pristine, sandy beach, and a serene Gunite pool equipped with a hot tub and pool house with a full bathroom. The first floor features a spacious living area and a flexible den/dining room, both with wood-burning fireplaces. A first-floor bedroom adds convenience and versatility. The kitchen, complete with a butler's pantry and bar area, leads to a mudroom providing additional storage. The second floor offers five bedrooms, including two en-suites, and two additional full bathrooms, ensuring plenty of space for family and guests. Thoughtfully designed with multiple staircases, this home offers convenience and seamless flow between levels. Additional highlights include wide pine floors throughout, detached carriage house with a finished room, walkout basement, and 7-bedroom septic system. Located just minutes from Osterville village, this iconic home is the perfect property for anyone seeking an oceanfront sanctuary.
1929 | 6 | 6 | 4,470 sqft.
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$12,250,000 - Osterville, MA
71 Sand Point Osterville, MA - 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.
1951 | 5 | 5 | 5,747 sqft.
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$10,995,000 - Osterville, MA
168 Garrison Lane Osterville, MA - Set on highly sought-after Garrison Lane, this extraordinary residence boasts one of the most desirable locations in Osterville with panoramic views of West Bay and Eel River. The property is a boater's paradise with a protected deep-water dock offering easy access to Nantucket Sound. Beautifully constructed with exquisite finishes, the five-bedroom home is positioned to provide stunning water views from nearly every room with multiple outdoor living areas. A large great room with double-height ceilings sits at the center of the home, with an adjacent eat-in kitchen that opens to a waterside terrace. Comfort and convenience are afforded with expansive primary suites on both the first and second floors. Three additional guest bedrooms are located on the second floor, while the finished walkout basement provides flexible bonus space with a kitchenette and wet bar. Set amidst rolling lawns and manicured gardens, this magnificent estate is minutes from everything Osterville has to offer.
1993 | 5 | 6 | 7,565 sqft.
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$10,800,000 - Osterville, MA
545 Sea View Avenue Osterville, MA - Set on Osterville's prestigious Sea View Avenue, this exquisite waterfront estate boasts an unparalleled combination of privacy, presence, and natural beauty. Sweeping views of Nantucket Sound and a pristine private sandy beach highlight this one-of-a-kind offering, located just minutes from everything Osterville has to offer. Accessed via a long, tree-lined driveway, coastal gardens and rolling lawns set the stage as one approaches the classic Cape Cod residence. Immediately upon entering, breathtaking views are on full display and continue throughout, with large windows and glass doors that seamlessly connect to multiple outdoor living spaces. At the heart of the home, a generously proportioned living room with three exposures is flooded with natural light, opening to a den on one side and a dining room on the other. Fit for any occasion, the dining room connects to the adjacent kitchen featuring an eat-in breakfast bar and water views. A guest bedroom completes the first level, offering convenience and flexibility. On the second floor, five additional bedrooms - including a spacious primary suite with mesmerizing vistas over Nantucket Sound - ensure ample accommodations for family and friends. Outside, the expansive lawn and terraces are ideal for embracing the outdoor lifestyle, while a staircase at the edge of the yard leads to one of Cape Cod's finest private sandy beaches. Just moments from The Wianno Club, Oyster Harbors, and the shops and restaurants of Osterville's Main Street, this rare and extraordinary property is ready to be enjoyed.
1947 | 6 | 6 | 3,859 sqft.
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$10,500,000 - Osterville, MA
501 Eel River Road Osterville, MA - 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 ensuite 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.
2017 | 6 | 8 | 8,203 sqft.
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$10,450,000 - Osterville, MA
25 Oyster Way Osterville, MA - Located within the private, gated golf community of Oyster Harbors, in the village of Osterville, is this magnificent five-bedroom waterfront residence with an in-ground pool and deep-water dock. This beautiful residence has the look and feel of a European estate with an open floor plan design and beautiful water vistas. Refined architectural details set the tone in this grand home with 7,157 sq. ft. of living space. Interior spaces begin with a spacious foyer opening into an extraordinary great room with vaulted ceiling, walls of windows, dramatic columns and custom fireplace. A light filled dining room overlooks the water with custom arched windows leading into a stunning chef's kitchen with coffered ceiling, granite countertops with large center island and access to a waterside patio. A lavish first floor primary suite and four additional bedrooms, including a full suite over the garage, offer ample room for family and friends. This unique and inspirational home is set on a private 1.65 acre parcel with beautiful outdoor seating areas overlooking the water, the pool, gardens and deep-water dock creating an ideal backdrop for entertaining family and friends. There is an attached three car garage, and this property provides plenty of extra parking. This one-of-a-kind property will appeal to the most discerning buyer.
1999 | 5 | 4 | 7,157 sqft.
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$8,950,000 - Osterville, MA
255 Bayberry Way Osterville, MA - Welcome to ''Point House'' a spectacular 5.98-acre waterfront estate on a peninsula overlooking the glistening waters of West Bay. In a setting of unsurpassed beauty, the 4,896 square foot residence offers truly exceptional water vistas, beautiful gardens, an expansive private sandy beach, and a substantial deep-water dock from which you can sail into the waters of Nantucket Sound. The 6-bedroom home features generous yet comfortable living spaces, beautiful architectural detailing, custom wood flooring and 5 fireplaces. The entry foyer welcomes you to the beautiful views and impressive deck that runs the length of the home and beckons you to step outside to take in the panoramic views. Highlights include a light filled, two story great room with a beautiful floor-to-ceiling brick fireplace, a well-equipped kitchen opening into the dining area and a family room accented by a fireplace all opening to the outside living spaces making this flow ideal for quiet family enjoyment or larger scale entertaining. Two bedrooms and a sitting room with fireplace can also be found on the 1st level. The primary bedroom features beautiful water views, a spacious bath, walk in closet and a large sitting room with fireplace, and three additional bedrooms and a sitting room finish the 2nd level. A third-floor walkup to a tower provides the perfect vantage point to watch the incredible sunsets you'll experience from this property. Also offered is a detached two car garage which includes living space above for extended family and guests. This seaside estate affords the utmost privacy yet offers proximity to the village of Osterville with its boutique shops and fine dining. Experience an exceptional lifestyle from this one-of-a kind waterfront estate!
1988 | 7 | 6 | 4,896 sqft.
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$8,000,000 - Osterville, MA
440 Grand Island Drive Osterville, MA - 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.
2013 | 7 | 10 | 11,546 sqft.
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$6,480,000 - Osterville, MA
44 Seapuit Road Osterville, MA - Osterville Oasis. Sitting on 3.4 acres and abutting 2.88 acres of additional protected land, this exceptional estate offers a family retreat like no other. The home—recently spotlighted by The Wall Street Journal—boasts over 8,000 square feet of thoughtfully designed living space with fully updated systems in pristine condition. The outdoor amenities are unparalleled, featuring a sparkling pool with a charming pool house that offers two bedrooms and a kitchenette, a top tier pickleball court, and a bocce court. Perfect for both intimate gatherings and grand-scale entertaining, the home's interior features two elegant living rooms, an inviting eat-in kitchen, and seamless access to the patio—complete with a hot tub for year-round relaxation. The main floor also hosts the luxurious primary suite, offering a serene retreat. Upstairs, four additional bedrooms, a fully equipped gym, and a recreation room provide endless options for family fun and fitness. With the added convenience of a short distance to Osterville village for shopping and dining.
2001 | 5 | 5 | 8,345 sqft.
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$6,285,000 - Osterville, MA
245 Bay Road N Osterville, MA - An elevated site offers the finest golf course views on Oyster Harbors. Gil Hanse recently completed a restoration of this Donald Ross gem, and now, as a championship course it will certainly rank among the finest in the state and on the east coast. Built by the areas premier builder and designed by Royal Barry Wills, the home features a first-floor primary suite and four additional bedrooms. Two of the bedrooms are in the connected apartment with its own kitchenette and living room. A butler's pantry, laundry and full bath are adjacent to the original Smallbone kitchen which has been thoughtfully updated. Five working fireplaces, a custom wine cellar, designer closets and endless storage will provide year-round access for your extended family. The pool and hot tub are sited to provide privacy and tranquility. We are certain that you will never tire of the movie set views which will simply take your breath away!
1988 | 5 | 6 | 4,637 sqft.