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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.

      186 Windswept Barnstable MA 02655

      Barnstable, MA186 Windswept Way

      Price$18,800,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22104798

      • Single Family
      • MLS Status Active
      • Village Osterville
      • Year Built 1933
      • Bathroom 8

      Waterfront Legacy Property on Oyster Harbors! Perched on an elevated four-acre lot overlooking Cotuit Bay sits this striking example of a Tudor style residence designed by renowned Architect Clifford Allbright in 1933 and since beautifully maintained and updated in harmony with the original design. Refined architectural details set the tone in this grand home with over 10,000 sq. ft. of living space, an inground pool, a boathouse with extraordinary views, fireplace, sitting area and changing rooms, 437 linear feet of water frontage and a substantial deep-water dock, all combining to create an exceptionally rare offering in arguably one of the finest locations of Oyster Harbors. As you enter this home you will find yourself in a timeless and enchanting foyer that is equally refined with an impressive custom spiral staircase. Gracious formal living and dining rooms feature well-proportioned and spacious areas with soaring ceilings and wood and slate flooring, custom arched windows and doors and multiple fireplaces. Floor to ceiling walls of windows flood the rooms with natural light and beautiful water views are found throughout. A spacious great room anchors the home and provides the ideal meeting place. This home offers eight bedrooms including a spacious primary suite featuring fabulous water views, fireplace, and adjoining office/library. This lovingly preserved estate boasts perfectly landscaped park-like grounds with multiple garden beds, breathtaking in their array of colors flanking the property on all sides, rolling green lawns, and a wraparound patio overlooking the gardens and water creating an ideal backdrop for entertaining family, friends, and large social gatherings. The exceptional architectural design of this home and its magnificent one-of-a-kind waterfront setting, create an opportunity that will surely captivate the most discerning buyer. There really is no comparison! 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.

      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

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

      Federal 30-year interest rate: 3.05% last updated on 2021-10-14

      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$15,900,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 21904886

      • Single Family
      • Garage Spaces 2
      • MLS Status Active
      • Village Osterville
      • Bedrooms 9

      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: 3.05% last updated on 2021-10-14

      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$13,200,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22100361

      • Single Family
      • Garage Spaces 3
      • MLS Status Pending
      • 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 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.

      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

      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: 3.05% last updated on 2021-10-14

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

      771 Sea View Barnstable MA 02655

      Barnstable, MA771 Sea View Avenue

      Price$12,900,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22106083

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

      The lure of breathtaking ocean views and the appeal of a private white sand beach are the highlights found in this beautiful waterfront residence overlooking Nantucket Sound. Accessed by a long driveway, and encompassing 1.82 acres, this classically designed home, crafted with elegance and grace, has been beautifully maintained and enjoys desirable southern exposure, well-proportioned rooms, and ample natural light. Offering 4600 square feet of interior space, all principal rooms open onto backside decks with sweeping vistas over the lawn and water. Features include formal living, dining, and family rooms, all with fireplaces, a well-equipped kitchen with dining area, spacious sunroom and library. The principal bedroom features an adjacent study with fireplace and private balcony and three additional bedrooms make up the second level. This splendid property has been beautifully landscaped opting for privacy but also aiming for a look that is peaceful and blends into the symmetry of the house. A tennis court, rolling green lawns, brick patios and multiple decks overlooking the water entice you to visit these outdoor spaces. A path from lawn's end leads you to your private white sand beach with over 120 feet of water frontage. Also offered is a detached two car garage with adjacent finished living space. Located just minutes from the restaurants and boutiques of Osterville village, this stunning location presents a wonderful opportunity to create the ideal family estate. 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 and 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

      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: 3.05% last updated on 2021-10-14

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

      48 Oyster Barnstable MA 02655

      Barnstable, MA48 Oyster Way

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

      Est. Mortgage: $/month

      MLS Number 22105240

      • Single Family
      • Garage Spaces 5
      • MLS Status Active
      • Village Osterville
      • Year Built 2005

      Tucked away on a private drive is this stunning contemporary residence located in the renowned gated community of Oyster Harbors. A grand foyer leads to the beautifully designed interior spaces showcased with soaring ceilings, gleaming hardwood floors and rich architectural detailing. With 9,859 sq. ft. the main residence offers a total of 5 bedrooms and 5 full and 2 half bathrooms and a Savant smart home system. The principal rooms are adorned with columns providing the ideal backdrop for formal entertaining. There is a spectacular and centrally located gourmet kitchen, fabulous great room with custom stone fireplace, luxurious 1st floor master suite with adjacent office and a light filled garden room. Other highlights include formal living and dining rooms, breakfast nook, butler's pantry as well as on the second floor four bedrooms, a large office/playroom and spacious media room. This magnificent residence sited on 1.52 acres features a lavish outdoor environment complete with in-ground salt water pool, outdoor fireplace, gardens, green lawns, ample patio spaces, an attached 2 car garage and detached 3 car garage with bonus room and full bathroom above.

      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: 3.05% last updated on 2021-10-14

      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: 3.05% last updated on 2021-10-14

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

      38 Bay Barnstable MA 02655

      Barnstable, MA38 Bay Street

      Price$3,850,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22105797

      • Single Family
      • Garage Spaces 3
      • MLS Status Active
      • Village Osterville
      • Year Built 1724

      A unique property nestled in the quaint village of Osterville..a historic renovation tastefully restored by Scott Crosby Builder with all today's modern amenities including a wonderful addition that houses a chef's kitchen, 4 season sunroom, primary suite with office, walk in closet, bathroom & bedroom. Over the 3 car attached garage addition, you will find another living area with 2 bedrooms, bathroom, wet bar separate from other living areas for a private guest retreat.In the historic front section there is a bedroom, full bath & living area with original beams & reproduction windows, hardware & back to back gas fireplaces . This section of the house was raised & a full basement was added.In the addition part of the house the basement contains a wonderful game room/den & ample storage. Exit from lower level is a double door with storm shutters on all windows & double door.The original carriage house was relocated to the lower portion of the property with ground level storage & guest quarters on 2nd level.This property has it all! Perfect for multi-generational living convenient to the village for shopping, restaurants, beaches, golf ,farmer's markets,etc. Not to be missed!

      Listed by Janet A Gosselin and Kevin P Cosgrove of Kinlin Grover 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: 3.05% last updated on 2021-10-14

      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. Property is being offered fully furnished. 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: 3.05% last updated on 2021-10-14

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

      313 Bridge Barnstable MA 02655

      Barnstable, MA313 Bridge Street

      Price$3,450,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22104229

      • Single Family
      • Garage Spaces 3
      • MLS Status Pending
      • Village Osterville
      • Year Built 1940

      Pristine Little Island Estate! This exquisitely maintained property features a quintessential main residence with tremendous Cape Cod Charm, approx. 3,600sf of living area w/ 5-bedrooms (1 of which is a gracious 1st flr master suite), 4.5-baths, a beautiful kitchen that is open to the dining area & family rm w/ a gas fireplace, an expansive 3-season porch, a lg. formal dining rm. that overlooks the yard & pool, a formal living rm, an office, laundry, & rooftop deck. The 3-car carriage house has a beautiful, wide open finished 2nd floor which would be perfect for a home gym or movie theater, and it has a full bath. The stunning pool house has a full bathroom, kitchenette, laundry and is adjacent to the outdoor grilling area with its stone surround grill. The warm and inviting heated pool has a pebble tech finish and a retractable pool cover. The 2nd floor of the pool house is perfect for guests with its own kitchenette and full bath. The manicured professionally landscaped yard features mature plantings, various specimen trees, extensive flower beds which add great colors, an irrigation system, monitoring cameras, an outdoor shower, & generator.

      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: 3.05% last updated on 2021-10-14

      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$3,295,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22102855

      • Single Family
      • Garage Spaces 3
      • MLS Status Active
      • Village Osterville
      • Bedrooms 5

      ''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: 3.05% last updated on 2021-10-14

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

      10 Starboard Lane Barnstable MA 02655

      Barnstable, MA10 Starboard Lane

      Price$2,999,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22100897

      • Single Family
      • Garage Spaces 3
      • MLS Status Pending
      • Village Osterville
      • Year Built 2006

      A remarkable three-story seaside estate, this oasis promotes a lifestyle of luxe-comfort. With its superb Osterville location, some of the Cape's most beautiful beaches are only moments away. Sun, swim or sail on East Bay, Centerville Harbor, Bumps River, Joshua Pond or Nantucket Sound. After a day on the water, return home where 14 elegant rooms provide ample spaces to live, work or play. Enjoy time together in the stunning chef's kitchen, dining room or solarium before retiring to one of the 5 bedroom suites to recharge. Learn more about this unique property by scheduling a showing.

      Listed by W&W Boston/Cape Cod Connection and Estelle Colgan of Compass Massachusetts,LLC

      {$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: 3.05% last updated on 2021-10-14

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

      131 Garrison Barnstable MA 02655

      Barnstable, MA131 Garrison Lane

      Price$2,950,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22104425

      • Single Family
      • Garage Spaces 2
      • MLS Status Active
      • Village Osterville
      • Bathroom 4

      Privately set on 1.6 acres adjacent to conservation land, this handsome Cape is located in an exclusive estate neighborhood located off of Sea View Avenue. This sprawling property has been wonderfully maintained and offers stunning curb appeal with mature landscaping and rolling lawns. Designed for effortless entertaining, the classic home features an inviting fireplaced family room, formal dining room, chef's kitchen with breakfast nook, and beautiful patio. Other notable features include a glorious sunroom, library, first-floor primary bedroom suite, three nicely appointed guest bedrooms, upper level sitting rooms, and two-car garage with separate guest quarters. Tucked away yet close to the Wianno Club and village amenities, this spectacular residence offers the very best of coastal living.

      Listed by Paul E Grover and Matthew de Groot 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: 3.05% last updated on 2021-10-14

      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 October 21, 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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