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      Osterville Luxury Homes

      Search for the latest luxury homes for sale in Osterville, MA. Look through a variety of scenic listings including waterfront and beachfront properties. Buyer Brokers of Cape Cod is your real estate resource for the Cape.

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      Contact Buyer Brokers of Cape Cod - our team can help answer any questions, set up private showings and provide additional information for any listing below.

      10,20,21 Scallop Barnstable MA 02655

      Barnstable, MA10,20,21 Scallop Path

      Price$19,800,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22103487

      • Single Family
      • Garage Spaces 4
      • MLS Status Active
      • Village Osterville
      • Year Built 1770

      Located on the private island of Oyster Harbors, and overlooking Nantucket Sound and Martha's Vineyard, one of Cape Cod's original homes presides over its location as vestige of a bygone era. Complete privacy is assured with almost 7. 5 acres on an elevated bluff. The water view encompasses 270 degrees. The site includes multiple buildings on three separate buildable lots. ''Scallop Path'', as the property is known, is now available for sale for the first time in almost 50 years. The main house, with 7 bedrooms and 5 full baths, is believed to have been moved across Cotuit Bay from the mainland to Oyster Harbors in the 18th century. The core of the home may date to as early as 1680 and some features certainly reflect that history. The sizable central chimney houses a passageway where the occupants could safely hide, perhaps during King Phillip's War. In all the buildings have 8 fireplaces.Restored by a well-known family in the 1970's the home and guest house were modernized to include central air conditioning and other modern features. Perhaps the property's most renowned feature are the gardens. Flower gardens, herb and vegetable gardens were all designed by one of country's most famous horticulturalists. This same individual actually redesigned the White House gardens in the 1960's. A guest house from the 1970's contains two separate bedrooms, bathrooms, kitchen and laundry. Other buildings on the site include classic architectural features. A woodshed is a point of focus while functioning as a working shed. The boathouse and garage are connected to each other by a breezeway overlooking a secluded cove. While the property currently contains 5,894 square feet of living space, architect Patrick Ahearn has filmed a video to discuss what the future may hold for the site. New owners will be able to create a sanctuary of their own in what many view as a picturesque paradise from another time.

      Listed by Zenas Crocker of Berkshire Hathaway HomeServices Robert Paul Properties

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

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      Price Down Payment Interest Rate Years
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      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      198 & 227 Bridge Barnstable MA 02655

      Barnstable, MA198 & 227 Bridge Street

      Price$16,900,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21904886

      • Single Family
      • Garage Spaces 2
      • MLS Status Active
      • Village Osterville
      • Year Built 1900

      Imagine the splendor of a life lived as a steward of the harbor. For the last 40 years, that's exactly what the owners of this timeless estate on Little Island in Osterville have done. From their vantage point at the head of the inlet, they have watched as thousands of boats of varying shapes and sizes have paraded their passengers in and out of West Bay. They have welcomed many of these seafarers to their docks to tie up while they awaited the rise of the drawbridge into North Bay and have shared refreshments with them at their refurbished antique shanty or private sand beach while they passed the time. With four distinctive dwellings on their privately set 3.73 acres, they have hosted many a get together both formal and informal and more often than not have enjoyed the quiet serenity and immeasurable beauty of their unique waterfront oasis. This is your once in a lifetime opportunity to embrace this captivating lifestyle.

      Listed by Reciprocal Agent of Reciprocal Office

      {$office->Name}

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

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      Price Down Payment Interest Rate Years
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      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      47 Sea View Barnstable MA 02655

      Barnstable, MA47 Sea View Avenue

      Price$12,250,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22004301

      • Single Family
      • Garage Spaces 2
      • MLS Status Pending
      • Village Osterville
      • Year Built 1900

      Architecturally stunning and masterfully restored, this multigenerational waterfront residence known as ''Sea Goddess'' overlooks the beautiful waters of Nantucket Sound with a private sandy beach. Circa 1900, this historically significant home, with incomparable oceans views, was refurbished in 2018 to the highest standards to create a peaceful and private luxury estate. Through the collaborative efforts of owner, architect and builder, the three-level home with over 5,500 square feet of living space and seven bedrooms, was a 2020 Bullfinch Award winner by the Institute of Classical Architecture and Art. The formal living and dining areas along with a stunning chef's kitchen, family room, Sun room and enclosed porch combine to offer the perfect setting for family, friends and large social gatherings. Appointments include significant millwork, four fireplaces, custom built-ins, coffered ceilings, Lutron Lighting system, recreation room, multiple outdoor seating areas, pool, hot tub, and cabana. The center drive is bordered by two new carriage houses and the professionally landscaped grounds are magnificent. Located just minutes from the restaurants and boutiques of Osterville village, this unparalleled lifestyle overlooking one of Cape Cod's most beautiful beaches is truly a one of a kind offering for the most discriminating buyer. Information herein is not guaranteed or warranted and should be verified by any person who is looking at this property to purchase.

      Listed by Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

      {$office->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      333 Seapuit Barnstable MA 02655

      Barnstable, MA333 Seapuit Road

      Price$7,950,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22100361

      • Single Family
      • Garage Spaces 3
      • MLS Status Active
      • Village Osterville
      • Year Built 1914

      Prominently sited on a protected cove with direct access to North Bay and beyond to Nantucket Sound, this storied heritage estate is set on over 3.5 acres creating an unmatched setting for extraordinary living. Surrounded by captivating water views, this remarkable property offers a rare opportunity for complete seclusion in the heart of Osterville. Built in 1914, the five-bedroom main house is a time-honored lodge with magnificent water views and handsome period detail. The guest house is simply perfect for waterside entertaining and relaxed getaways. Located in one of Osterville's finest estate neighborhoods, this property boasts dual frontage on two pristine bodies of salt and freshwater, rolling lawns, lush gardens, and swimming pool. This exquisite offering presents a unique opportunity to create an unrivaled generational compound with effortless proximity to renowned village shops, restaurants, marinas, and Wianno and Oyster Harbors clubs. Please note that an adjoining 4.01 acre parcel with deep water dock is available for purchase.

      Listed by Paul E Grover and Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

      {$office->Name}

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

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      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      183 Bay Barnstable MA 02655

      Barnstable, MA183 Bay Street

      Price$6,995,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22005399

      • Single Family
      • Garage Spaces 2
      • MLS Status Active
      • Village Osterville
      • Year Built 2016

      Magnificent seaside estate boasts exquisite architectural finishes, commanding views of North Bay, lush meadows, and private dock. Masterfully built in 2016 by Peter Boyle, this gracious residence has been meticulously designed by Ivan Bereznicki to capture sensational water and golf course views while effortlessly blending the finest craftsmanship with luxurious amenities to create an idyllic seaside retreat. Highlights include state-of-the art kitchen with superb finishes, waterside fireplaced living room, paneled library with built-ins, splendid master suite, three handsome guest bedrooms with en suite baths, and serene vistas from nearly every richly appointed room. Tucked away yet close to village amenities, this one-of-a-kind masterpiece is the pinnacle of refined coastal living.

      Listed by Paul E Grover of Berkshire Hathaway HomeServices Robert Paul Properties

      {$office->Name}

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

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      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      92 North Bay Barnstable MA 02655

      Barnstable, MA92 North Bay Road

      Price$6,250,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22000918

      • Single Family
      • Garage Spaces 2
      • MLS Status Pending
      • Village Osterville
      • Year Built 1981

      Fabulous waterfront residence overlooking the beautiful waters of North Bay in the private gated community of Oyster Harbors. Sweeping water views greet you as you enter this stunning 6,482 square foot home featuring 6 bedrooms including 2 spacious first floor master suites, a beautifully designed kitchen, generous living and dining rooms and a stunning great room with expansive walls of windows and elevated ceilings blending indoor and outdoor living. This special property has had many upgrades and features exceptional attention to detail throughout. The lower level is finished with an entertainment room, home theater and spacious office with custom built-ins. Panoramic water and golf course views, an in-ground pool with pool house and private and substantial deep water dock combine to create the finest elements in seaside living. Information contained herein is believed to be accurate but should be independently verified by prospective buyers.

      Listed by Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

      {$office->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      46 Little Island Barnstable MA 02655

      Barnstable, MA46 Little Island Drive

      Price$4,795,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 21905860

      • Single Family
      • Garage Spaces 3
      • MLS Status Pending
      • Village Osterville
      • Year Built 1998

      Little Island in Osterville provides a picturesque setting for what has long been a family-loved estate overlooking West Bay. This spacious, custom-built residence is situated on a little less than 3 acres of meticulously manicured grounds, all tended to by a certified Master Gardener.Spanning 5,680 square feet this exceptional home provides the perfect balance between open living space and private quarters for family and guests alike. Beautifully appointed with gleaming hardwood floors and an open floor plan, the main level will leave you speechless. A grand, two story family room, just off the large eat-in kitchen, opens seamlessly onto the water via floor-to-ceiling windows and doors. A sizable living room, dining room and pantry complete the first floor. The ultimate home retreat, the impressive master suite comes outfitted with French doors that lead to a private salon. Beyond the walls, family and friends will find serenity on the spacious bluestone patio, all surrounded by verdant gardens and breathtaking water views. A shared dock and beach on the water of West Bay complete this very special and beloved Little Island property.

      Listed by Jack Tobin of Berkshire Hathaway HomeServices Robert Paul Properties

      {$office->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      533 Wianno Barnstable MA 02655

      Barnstable, MA533 Wianno Avenue

      Price$3,995,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22102619

      • Single Family
      • MLS Status Pending
      • Village Osterville
      • Year Built 1930
      • Bathroom 4

      Landmark. A descriptive phrase that is quite casually even thoughtlessly tossed about. A real Osterville Village Landmark, 533 Wianno Avenue meets any definition of the word you can conjure. Welcome to 533 Wianno Avenue, a property you will recognize either from actually driving by or from past dreams where you imagined the perfect seaside village shingle style retreat. From the signature blue hydrangea ellipse in the front yard and the expansive greensward framed cedar shingled gambrel presence; it captures all that we cherish about Village Style. Lovingly restored, this five bedroom 4,100 square foot masterpiece beckons you to come in, relax, restore, refresh and recreate memories that will become landmarks in a life well lived. If you choose to be found, its easy: tell your visitors to start down Wianno Avenue and look for the hydrangea house about five seconds before the beach. Like a true landmark, it can't be missed. We look forward to finding you here. Please verify all information contained herein.

      Listed by John B Cotton, Jr of Sotheby's International Realty

      {$office->Name}

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

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      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      95 Eel River Barnstable MA 02655

      Barnstable, MA95 Eel River Road

      Price$3,950,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22004995

      • Single Family
      • Garage Spaces 2
      • MLS Status Pending
      • Village Osterville
      • Year Built 1988

      Breathtaking views over Osterville's West Bay with ever changing scenes of beautiful boats, wildlife and stunning sunsets provide endless enjoyment in this private and tranquil setting. This gracious, well-constructed home, with classic architecture designed by Royal Barry Wills, is impeccably maintained, and has sprawling peaceful grounds leading to the private beachfront and sailboat dock. A beautiful stone terrace connects to the first floor living areas and kitchen, and connects to an expansive deck with direct access to the privately sited first floor master suite. The well-designed floor plan provides comfortable transition throughout the gracious first floor entertaining rooms, and the sleeping areas provide plenty of privacy for both family and guests. The recently finished lower level provides an additional bedroom, media room and storage. Lovely grounds feature well-established flowering shrubs and mature trees, along with beautiful vistas to the water. A nice balance of sun and shade allows for maximum outdoor enjoyment, and the terrace is the perfect place to enjoy the spectacular sunsets overlooking the water.

      Listed by Peggy Rowland and Sam B Wilson of Sotheby's International Realty

      {$office->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      83 Bunker Hill Barnstable MA 02655

      Barnstable, MA83 Bunker Hill Road

      Price$3,650,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22101858

      • Single Family
      • Garage Spaces 3
      • MLS Status Active
      • Village Osterville
      • Year Built 1983

      This stunning, 5 bed, 6 & 1/2 bath 5700+ sq ft home sits on 3 acres with a dazzling pool in the desirable Seapuit area lending easy access to historic Osterville. Greeted by a beautiful staircase, glowing oak floors, and elegant wainscoting the tall windows pour natural light into the spacious living spaces with gorgeous coffered ceilings. The stunning brand new kitchen boasts marble countertops, bright white cabinetry, and stainless steel gourmet appliances, which includes 2 dishwashers & 2 subzero refrigerators, and a wine cooler. Conveniently placed on the 1st floor the primary bedroom features two beautifully updated his and her bathrooms. The remaining bedrooms are open and generous while the bathrooms have been beautifully updated. Outside, a vast deck, the pool house with kitchenette and bar, with the water rights to Dam Pond (access to Nantucket Sound) mean there is always plenty to do. Extra features include a whole house generator, a heated three-car garage, outdoor shower, two laundry rooms and more. Enjoy elegant Cape Cod living in this striking home, come view today!

      Listed by Danny M Griffin of Griffin Realty Group

      {$office->Name}

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

      Do not fill in this field:

      Do not fill in this field:

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      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      405 Bridge Barnstable MA 02655

      Barnstable, MA405 Bridge Street

      Price$3,500,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22102855

      • Single Family
      • Garage Spaces 3
      • MLS Status Active
      • Village Osterville
      • Year Built 2000

      ''Coming Home,'' two words that when paired create powerful feelings, emotions and expectations. Coming Home, where we are welcomed, we are safe, we are embraced. I could write endless paragraphs about this phenomenal 6,700 Square Foot five Bedroom shingle style masterpiece set on 1.13 Acres of Park Like grounds. I could even write about the two and a half story ceilings, superb workmanship and glimpses of West Bay. You can learn all that and more from the fact sheet. I would rather talk about Coming Home... because even though I don't live here, it's exactly how I feel each time I visit here. Hard to explain: It's the feeling of a great home, one that is solid, one results from a feast for the eye... yes, one that embraces you when you enter. You should experience this. 405 Bridge Street. Come visit, experience and fall in love. Come home. Please verify all information contained herein.

      Listed by John B Cotton, Jr of Sotheby's International Realty

      {$office->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      473 Grand Island Barnstable MA 02655

      Barnstable, MA473 Grand Island Drive

      Price$3,495,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22006277

      • Single Family
      • Garage Spaces 3
      • MLS Status Active
      • Village Osterville
      • Year Built 1991

      Beautifully sited on a corner lot in the desirable Oyster Harbors gated community, this impressive home offers a seamless integration of formal spaces with casual living areas perfect for today's lifestyle. A grand 2-story foyer with gracious curved staircase welcomes you to the home and the formal living and dining rooms. The heart of the home is the luxury custom gourmet kitchen with center eating island, work island, granite counters, top brand appliances, glass/ceramic tile back-splash and entertainment area with wine cooler. Casual spaces include a sun-splashed great room, cherry paneled library and bright sunroom overlooking the in-ground pool and outdoor decks. A separate wing 1st floor master suite with access to the outdoors provides privacy while an ample size guest suite allows family & friends to stay for extended periods of time if needed. Deeded beach and docking rights included.

      Listed by Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

      {$office->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.78% last updated on 2021-07-22

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      broker reciprocity The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Buyer Brokers of Cape Cod are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Buyer Brokers of Cape Cod shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

      This site was last updated July 29, 2021. All properties are subject to prior sale, changes, or withdrawal.

      Buyer Brokers of Cape Cod has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.

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