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      Osterville MA Homes for Sale

      Find the latest homes for sale in Osterville, MA with Buyer Brokers of Cape Cod. Save your favorite listings to your account. If you don't have an account with us, you can register here. You'll be able to keep track of your saved listings and when new properties match your search criteria.

      Be sure to contact us to schedule a showing for any listing below or if you have any questions about the Cape Cod real estate marker.

      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

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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: 2.88% last updated on 2021-09-23

      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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      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: 2.88% last updated on 2021-09-23

      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: 2.88% last updated on 2021-09-23

      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
      • Bathroom 4

      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: 2.88% last updated on 2021-09-23

      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:

      Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.88% last updated on 2021-09-23

      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: 2.88% last updated on 2021-09-23

      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: 2.88% last updated on 2021-09-23

      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: 2.88% last updated on 2021-09-23

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

      65 Starboard Barnstable MA 02655

      Barnstable, MA65 Starboard Lane

      Price$2,599,900The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22105550

      • Single Family
      • Garage Spaces 2
      • MLS Status Active
      • Village Osterville
      • Year Built 1982

      This waterfront remodeled contemporary is located in a desirable area of Osterville. Located on North Pond with your own private dock enjoy fishing and kayaking. Home has a large first floor master with walk-in closet and private bath overlooking the in ground pool. Recent improvements include new kitchen and remodeled baths, siding and new heating system. New in ground pool area with outdoor kitchen, fire pit, and Jacuzzi. This home is used as a year round vacation rental with income for 2021 approaching $200,000.

      Listed by Shane Pacheco of SMP Realty Development Co. 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:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 2.88% last updated on 2021-09-23

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

      174 Wianno Barnstable MA 02655

      Barnstable, MA174 Wianno Avenue

      Price$1,999,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22104731

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

      Corner lot and lovely Cape Cod home on stately Wianno Avenue in the quintessential village of Osterville. Walk to the post office, library, restaurants and shops. Walk or bike ride to Dowses Beach. This property offers a floorplan with some flexibility and plenty of space, boasting 4 spacious bedrooms, 3.5 baths and an oversized living room with a fireplace, built-ins and a gleaming hardwood floor. The kitchen features a dining area with a fireplace and there is an adjacent room with optional uses, including a dining room or family room. There is a screened in porch and level backyard with mature plantings for privacy. With some updates and finishes to make it your own, this is a perfect place to call home!

      Listed by Lynda M Day and Diane D Boudreau 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: 2.88% last updated on 2021-09-23

      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 September 27, 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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      “We recently bought a home in West Barnstable and through the recommendation of a dear friend, who used Ed McKenna of Buyer Brokers of Cape Cod, we contacted Ed. What a breath of fresh air to actually have a real estate broker working on your behalf and advocating for you throughout the process. Ed found us a lovely home in West Barnstable and negotiated a number of [...]

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