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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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      198 & 227 Bridge Barnstable MA 02655

      Barnstable, MA198 & 227 Bridge Street

      Price$19,500,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21904886

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 1900
      • Bathroom 7

      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

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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: 3.24% last updated on 2020-05-21

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

      51 Sunset Barnstable MA 02655

      Barnstable, MA51 Sunset Point

      Price$16,500,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22002445

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 1918
      • Bathroom 6

      Perched upon an elevated almost ten-acre bay front parcel sits an exceptionally rare offering in arguably the finest location of Oyster Harbors. ''Faraway,'' as it is known, evokes the elegance of a bygone era and features commanding vistas of Cotuit Bay, Sampson's Island, Nantucket Sound, and on the horizon, Martha's Vineyard. Stately manicured grounds include sweeping lawns on all sides, a rose garden, gated swimming pool, and a wooden staircase along the breakwater down to a deep-water dock large enough for a substantial yacht.Tastefully updated over the course of 40+ years of single-family ownership, the main home has been meticulously maintained and almost all rooms enjoy a water view. In the entry hall you are greeted with sweeping views through floor-to-ceiling windows.Step-down into the formal loggia for entertaining; a wood-burning fireplace provides warmth and cheer. In the east-wing of the house is a stately living room with lovely built-ins and a Dutch door opening onto a cozy sun room overlooking the bay, lawn, and swimming pool.

      Listed by Robert B Kinlin of Robert Paul Properties, Inc.

      {$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:

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      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.24% last updated on 2020-05-21

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

      333-359 Seapuit Barnstable MA 02655

      Barnstable, MA333-359 Seapuit Road

      Price$14,995,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21908511

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 1914
      • Bathroom 4

      Prominently sited on Bog Pond with direct access to North Bay and beyond to Nantucket Sound, this storied heritage estate is set on over eight pristine acres creating an unmatched setting for extraordinary living. Surrounded by captivating water views, this remarkable property offers a rare opportunity for complete seclusion while 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, protected deep water dock, 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 this property is available as a compound or two individual waterfront home sites.

      Listed by Paul E Grover of Robert Paul Properties, Inc.

      {$office->Name}

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

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      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.24% last updated on 2020-05-21

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

      255 Eel River Barnstable MA 02655

      Barnstable, MA255 Eel River Road

      Price$11,900,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21900851

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 2005
      • Bathroom 8

      There are three possible benefits to living beside the sea: Views, beach and boating. Most properties offer one of these and most offer no more than two. This extraordinary residence offers ALL the benefits of living on the water and takes it even further. A private location within close proximity to the village center, west-facing views, pool and a painstakingly designed, built and maintained estate residence. Enjoy this extraordinary opportunity to experience the best of Osterville sea side living. Please verify all information contained her

      Listed by John A Largay, 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:

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      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.24% last updated on 2020-05-21

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

      134 Great Bay Barnstable MA 02655

      Barnstable, MA134 Great Bay Road

      Price$7,800,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21906484

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 2002
      • Bathroom 8

      This stunning Osterville residence is prominently situated overlooking North Bay at the end of a quiet lane. Architecturally significant, this waterfront home features impressive curb appeal, extraordinary craftsmanship and superb finishes throughout. Situated on 1.23 acres, this property offers panoramic water views, an inground pool with a beautiful bluestone patio, a sandy beach and a private dock with access to Nantucket Sound. The design of the home and its timeless craftsmanship contribute to its warm and comfortable atmosphere offering 8,500 square feet of living space with five bedrooms and seven bathrooms. Highlights include stunning millwork, custom ceilings and windows, a gourmet kitchen, butler's pantry, billiard room and spacious master suite with lavish bath to name just a few. Each outdoor feature adds to the home's overall ambience. From the back patios to the pool and sandy beach, to the cobbled drive and beautiful landscaping, the entire property exudes a mixture of prestige and elegance. A very special offering that you won't want to miss.

      Listed by Robert B Kinlin of Robert Paul Properties, Inc.

      {$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: 3.24% last updated on 2020-05-21

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

      979 Sea View Barnstable MA 02655

      Barnstable, MA979 Sea View Avenue

      Price$7,495,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21609913

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 1928
      • Bathroom 8

      Land's End, is a classic Old World Estate situated on 4.15 acres where the waters and shores of Nantucket Sound meet Osterville's West Bay. Grand, yet unpretentious, the home provides three floors of gracious entertaining and living spaces for family and guests, and offers unsurpassed panoramic water views spanning Nantucket Sound and down the Seapuit River to the West. A classic beach cabana with an expansive deck overlooking the private 500+ feet of white sand beach, brings you back to an era of easy summer living. The boat house provides storage for numerous boats and allows for easy launching from the beach. A private tennis court adds to the resort lifestyle and fits nicely into the natural landscape of the estate. Restore or Rebuild in this fabulous location! A life time opportunity to capture this spectacular and rare location with frontage on both Nantucket Sound and West Bay, and create your own memories for generations. Buyers to verify all information.

      Listed by Peggy Rowland 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: 3.24% last updated on 2020-05-21

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

      81 & 73 Oyster Barnstable MA 02655

      Barnstable, MA81 & 73 Oyster Way

      Price$6,750,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21610144

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 1999
      • Bathroom 8

      Exceptional waterfront estate located within the premier gated community of Oyster Harbors featuring breathtaking views of West Bay and Nantucket Sound, an in ground pool, private deep water dock and a separate one acre buildable lot. This stunning five bedroom residence with lush landscaping and light filled interior spaces has been thoughtfully designed and offers expansive windows with beautiful water views. Anchoring the home is a well-equipped kitchen with a spacious dining area opening into a great room with vaulted ceilings and fireplace. There's a handsome study/den and spacious and elegant first floor master bedroom. Custom columns, built-ins and beautiful wood floors enhance these spaces. Additional bedrooms on the 2nd level along with a private bedroom suite with sitting room, kitchen and bath all combine to create the ideal setting for family gatherings or large scale entertaining.

      Listed by Robert B Kinlin of Robert Paul Properties, Inc.

      {$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: 3.24% last updated on 2020-05-21

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

      250 Windswept Barnstable MA 02655

      Barnstable, MA250 Windswept Way

      Price$6,295,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21907235

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 1925
      • Bathroom 5

      Captivating Oyster Harbors estate, ''Windswept'' is an architectural masterpiece with sensational views of Cotuit Bay and Nantucket Sound. Sited on 4.5+ secluded acres with meandering private drive, the six-bedroom landmark residence has been meticulously restored with the finest of finishes and craftsmanship. Highlights include a chef's kitchen with top-of-the-line appliance suite, fireplaced waterside living room, charming den, inviting sun porch, and handcrafted millwork and period detail throughout this exceptional home. Perfectly set against the backdrop of glorious water views, the manicured grounds feature lush gardens, pool, tennis court, deep water dock, and private beach. With unmatched elegance and location, this masterful estate is destined to become a legend for the generations.

      Listed by Paul E Grover of Robert Paul Properties, Inc.

      {$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: 3.24% last updated on 2020-05-21

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

      150 Carriage Barnstable MA 02655

      Barnstable, MA150 Carriage Road

      Price$5,800,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21805370

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 1935
      • Bathroom 7

      Pics 1-9 depict architect's renderings of possible renovations that require no additional square footage - SEE SUPPLEMENT for more info.The second floor master bedroom includes both an en-suite bath with double sinks, shower, and whirlpool tub and a raised southeast-facing outdoor deck. There are two additional bedrooms on the second floor, one with an en-suite bath and the other with a bath down the hall. On the third floor there are two more bedrooms with a shared bath. Architect's suggested renovations depicted in Pics 1-9 (renderings) are at the buyer's sole discretion and expense.150 Carriage Road is a magnificent waterfront parcel with sweeping views of West Bay, a private setting, and an existing home with a full basement, and modern utilities anxiously awaiting a fresh update/remodel. These architect's renderings represent some relatively easy and timely remodels of the existing home by eliminating interior walls to create a more modern, open-concept interior living space while changes to the exterior would serve to create a more classic design and style fitting for the neighborhood and Cape Cod region. The main goal of these remodels is to highlight the importance of the main home while minimizing the appearance of the north wing by the reduction of the currently over-sized dormers. This property provides the rare opportunity for a fabulous, modern vacation home with a minimal commitment of time and expense; please note the remodels that these renderings depict would require no addition to the existing home. Multiple sites are possible for a pool if desired. The sale of the property includes title insurance.

      Listed by Herb Pheeney of Oyster Real Estate

      {$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: 3.24% last updated on 2020-05-21

      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$5,500,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22000918

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 1981
      • Bathroom 7

      Luxury living in the private gated community of Oyster Harbors! Fabulous waterfront residence overlooking the beautiful waters of North Bay offers the finest in seaside living. This special property has had many upgrades and features exceptional attention to detail. The 6,482 square foot home offers 6 bedrooms with 2 first floor master suites, a beautifully designed kitchen, comfortable family room and great room with floor to ceiling walls of windows to take advantage of the stunning views. The lower level is complete with a home theater, entertainment room 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 an ideal setting for large scale entertaining and peaceful family living. Information contained herein is believed to be accurate but should be independently verified by prospective buyers.

      Listed by Robert B Kinlin of Robert Paul Properties, Inc.

      {$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: 3.24% last updated on 2020-05-21

      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$4,995,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21905860

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 1998
      • Bathroom 6

      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 Robert Paul Properties, Inc.

      {$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: 3.24% last updated on 2020-05-21

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

      153 Sea View Barnstable MA 02655

      Barnstable, MA153 Sea View Avenue

      Price$4,950,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21900676

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 1906
      • Bathroom 5

      Beachfront Estate with 160+' of sandy beach!! This estate is situated on a bluff overlooking the soothing waters of Nantucket Sound. Enjoy magnificent sunrises & expansive southern exposure as you watch the sun dancing & sparkling off of the water. Listen to the waves lapping up on shore as you relax in the expansive sun rooms. Play yard games on the lawn overlooking the Sound. This classic wood shingle style residence is adjacent to the well acclaimed Wianno Club!! The residence provides an abundant amount of living area for family & friends and features large impressive rooms, custom millwork, 7 bedrooms, 4.5-baths, two fireplaces, and two magnificent sun rooms w/sweeping views of Nantucket Sound. Enjoy a refreshing swim in Nantucket Sound then relax on your own private beach. Property being sold 'as-is', Buyer responsible for any septic upgrades. All information contained herein should be verified by a potential Buyer(s) and their representatives.

      Listed by John J Hopkins of Frank A Sullivan Real Estate

      {$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: 3.24% last updated on 2020-05-21

      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 May 25, 2020. 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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