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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.

      835 Sea View Avenue Barnstable MA 02655

      Barnstable, MA835 Sea View Avenue

      Price$30,000,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22200155

      • Residential
      • Bedrooms 7
      • Bathroom 14
      • Square Feet 15,500

      Set on Osterville's exclusive Sea View Avenue with commanding views over Nantucket Sound and an unprecedented 280 feet of private sandy beach, a once-in-a-lifetime coastal oasis awaits. Magnificent landscaping sets the stage, with specimen trees and lush plantings that offer total privacy across 3.66 acres. Designed in perfect harmony with its surroundings, virtually every room has ocean views and direct access to the outdoors. A thoughtful layout divides the residence into a main house and attached guest house with a total of 7 en suite bedrooms. Outdoor living is highlighted by a resort-style swimming pool, summer kitchen, and expansive terrace for sunbathing and al fresco dining. Additional amenities include a 5,000-bottle wine cellar, golf simulator, gym, massage room, 7 garage spaces, and a separate staff house. Located in one of New England's most sought-after waterfront communities, this grand estate is minutes away from everything Osterville has to offer, yet a world apart.

      Listed by Paul E Grover 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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      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: 5.3% last updated on 2022-05-12

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

      159 Main Street Barnstable MA 02655

      Barnstable, MA159 Main Street

      Price$18,500,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22200221

      • Residential
      • Bedrooms 8
      • Bathroom 12
      • Square Feet 10,027
      • Parking Spaces 10

      The lure of breathtaking water vistas and the appeal of luxurious appointments compliment the superb setting in this grand waterfront estate in the heart of Osterville. Overlooking the glistening waters of Nantucket Sound, this spectacular property offers an impressive 4 acres of beautifully manicured grounds, approximately 400 feet of water frontage, an infinity edge, heated pool with hot tub and fully equipped cabana, a private dock with a boathouse and 650 square foot waterside deck. Beyond the gated entry, down a winding drive, a beautiful courtyard sets the tone for this architecturally stunning residence filled with natural light, where only the highest quality materials and artisanship are displayed throughout. Built in 2017, this one-of-a-kind residence features 10,000 square feet of living space, dramatic vaulted ceilings, expansive windows, Elan Smart Home system, multiple fireplaces and eight en-suite bedrooms including a spacious primary suite on the first floor featuring fabulous water views, a sitting area overlooking the water, custom Travertine marble flooring in the luxurious master bathroom, and a bonus room/office. A gracious dining room overlooks the water and

      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:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

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

      186 Windswept Way Barnstable MA 02655

      Barnstable, MA186 Windswept Way

      Price$16,800,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22104798

      • Residential
      • Bedrooms 8
      • Bathroom 8
      • Square Feet 10,063
      • Parking Spaces 5

      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

      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: 5.3% last updated on 2022-05-12

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

      34 & 52 Caillouet Lane Barnstable MA 02655

      Barnstable, MA34 & 52 Caillouet Lane

      Price$13,500,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22106688

      • Residential
      • Bedrooms 8
      • Bathroom 9
      • Square Feet 8,230
      • Parking Spaces 6

      Spectacular waterfront estate, with sweeping views of East Bay and Nantucket Sound, is distinguished by masterful design, meticulous attention to detail and a magnificent setting. This sophisticated property, nestled within 3.09 acres with 200 feet of water frontage, features main and guest houses, an in-ground gunite pool with pool house and a private dock with direct access to the Sound. The stunning five-bedroom main house, completely renovated in 2020, offers over 5,700 square feet of living space with water views from most rooms. Infused with natural light and the beautiful vistas, the interior of the house has a floor plan ideally suited for entertaining, both grand and intimate. Beyond the welcoming foyer, generously proportioned spaces have a graceful flow blending modern and traditional styles. Granite countertops, custom cabinetry, and top-of-the-line appliances fill the gourmet kitchen which opens into a fabulous family room. The open floor plan continues into formal living and dining rooms, connecting the main level to the outside patios, pool and meticulously landscaped grounds. A superb primary suite on the first floor offers an adjacent office with exterior access,

      Listed by Robert B Kinlin and Tom P Foley 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: 5.3% last updated on 2022-05-12

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

      320 Parker Road Barnstable MA 02655

      Barnstable, MA320 Parker Road

      Price$4,125,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22200265

      • Residential
      • Bedrooms 5
      • Bathroom 6
      • Square Feet 5,421

      Located a short stroll from Osterville Village, this shingle-style home showcases stunning architectural details and scenic views over Wianno Golf Course and Parker Pond. Exquisite craftsmanship is on full display throughout, from a spacious covered porch that greets visitors to a gourmet kitchen with honed granite countertops and cherry cabinetry. The first-floor primary suite includes a luxurious marble bathroom and secluded home office. On the second floor, an open family room is seamlessly connected to the outdoors with front and back decks, while offering the utmost convenience with a thoughtfully designed kitchenette. Two bedrooms and two bathrooms complete the second floor. Additional highlights include a four-car garage with a self-contained apartment above, a lush backyard, and a large bluestone patio. Mere minutes from everything Osterville has to offer, this extraordinary residence delivers the quintessential Cape Cod lifestyle.

      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

      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: 5.3% last updated on 2022-05-12

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

      473 Grand Island Drive Barnstable MA 02655

      Barnstable, MA473 Grand Island Drive

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

      Est. Mortgage: $/month

      Pending

      MLS Number 22006277

      • Residential
      • Bedrooms 5
      • Bathroom 6
      • Square Feet 7,126
      • Parking Spaces 5

      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: 5.3% last updated on 2022-05-12

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

      27 Parker Road Barnstable MA 02655

      Barnstable, MA27 Parker Road

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

      Est. Mortgage: $/month

      Pending

      MLS Number 22101898

      • Residential
      • Bedrooms 4
      • Bathroom 5
      • Square Feet 4,190
      • Parking Spaces 4

      NEW CONSTRUCTION! This TO BE BUILT home has been designed and will be built by well known Osterville builders, Kendall & Welch Construction Co. This spacious 4190+/- square foot home will consist of 4 bedrooms, 4.5 baths and is located in the center of Osterville, where you can walk or ride to everything this lovely seaside village has to offer. Amenities include hardwood floors, state of the art kitchen, butler's pantry, ensuite bedrooms and welcoming out door living spaces. Generous rooms, open space and exceptional detail will be the hallmarks of this special property. Pool & Pool House upgrade is available separately. If you are looking for a brand new home, in the perfect location, you will want to take advantage of this remarkable opportunity!.

      Listed by Gene Orloff 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: 5.3% last updated on 2022-05-12

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

      54 Cinnamon Lane Barnstable MA 02655

      Barnstable, MA54 Cinnamon Lane

      Price$1,275,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22201134

      • Residential
      • Bedrooms 3
      • Bathroom 3
      • Square Feet 2,500
      • Parking Spaces 5

      Come visit this Oyster Hills Charming and Quintessential cape that has been completely remodeled inside and out. Open floor plan provides bright and sunny rooms all day, making this a very ''happy home''. Renovations started in 2018 with a new roof just 1 month ago. High-end custom kitchen cabinets with marble quartz countertops. Sterio-ready sound system inside and out with a large private deck that's great for watching the Sox games on your outdoor tv. Huge landscaping remodel with new front stone walkway and patio to greet neighbors as they walk by. Shiplap throughout; beachy vibe with an outdoor shower that has you dreaming of riding the waves. Stunning gardens that will take your breath away!! Fabulous neighborhood and wonderful neighbors. No work needed here; just grab your beach towel and chair and head to the beach. What are you waiting for?? I look forward to meeting you soon.

      Listed by Julie Hopkins - White of William Raveis RE & Home Serv.

      {$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: 5.3% last updated on 2022-05-12

      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 19, 2022. 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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