Our mobile site is optimized for smaller screens.

TRY IT NO THANKS
MORE SEARCH OPTIONS

      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.

      835 Sea View Barnstable MA 02655

      Barnstable, MA835 Sea View Avenue

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

      Est. Mortgage: $/month

      MLS Number 22200155

      • Single Family
      • Garage Spaces 7
      • Full Bath 9
      • Half Baths 5
      • MLS Status Active

      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

      {$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: 3.45% last updated on 2022-01-13

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

      159 Main Barnstable MA 02655

      Barnstable, MA159 Main Street

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

      Est. Mortgage: $/month

      MLS Number 22200221

      • Single Family
      • Garage Spaces 3
      • Full Bath 8
      • Half Baths 4
      • MLS Status Active

      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 features a gas fireplace, with a butler's pantry discreetly accessed through pocket doors. The family room defines comfort with water views, a gas fireplace and a beamed ceiling, and the stunning home office is enhanced by handsome finishwork and a television hidden beneath a padded bench. The kitchen is truly the heart of the home, with the best of high-end appliances, numerous seating areas for entertaining, a built-in coffee bar, pantry with Liebherr 160-bottle wine refrigerator and adjoining three season sunroom. The second level offers seven en-suite bedrooms with spacious closets and custom tiled bathrooms, most with water views. An additional 2.11-acre Long Beach parcel with a sandy beach and secondary dock enhances the main property. This rare blend of classic charm, outstanding architectural details and modern appointments is truly the last word in gracious waterfront living.

      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: 3.45% last updated on 2022-01-13

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

      186 Windswept Barnstable MA 02655

      Barnstable, MA186 Windswept Way

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

      Est. Mortgage: $/month

      MLS Number 22104798

      • Single Family
      • Full Bath 6
      • Half Baths 2
      • MLS Status Active
      • Village Osterville

      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

      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: 3.45% last updated on 2022-01-13

      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
      • Full Bath 6
      • Half Baths 1
      • MLS Status Active

      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

      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: 3.45% last updated on 2022-01-13

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

      34 & 52 Caillouet Barnstable MA 02655

      Barnstable, MA34 & 52 Caillouet Lane

      Price$14,500,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22106688

      • Single Family
      • Garage Spaces 4
      • Full Bath 7
      • Half Baths 2
      • MLS Status Active

      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, and the second floor offers a charming sitting area, spacious media/game room and four bedrooms with stunning water views. The separate guest house with 2,500 square feet, three bedrooms and a finished walk out basement completes this incredible offering. This seaside estate affords the utmost privacy yet offers proximity to the village of Osterville with its boutique shops and fine dining. Experience an exceptional lifestyle from this one-of-a kind waterfront estate! 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 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: 3.45% last updated on 2022-01-13

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

      128 Starboard Barnstable MA 02655

      Barnstable, MA128 Starboard Lane

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

      Est. Mortgage: $/month

      MLS Number 22107063

      • Single Family
      • Garage Spaces 2
      • Full Bath 5
      • Half Baths 1
      • MLS Status Active

      This is a rare opportunity to purchase an Osterville waterfront compound that ambles along the river and is gently nestled into one of the most beautiful natural settings on Cape Cod. Watch swans nest, ducks swim and herons fly while enjoying indoor /outdoor living on over 2.5 acres. This Osterville home enjoys gracious rooms with beautiful views all on one level. The one bedroom guest house (480 sq. ft.) called 'The Crow's Nest', is its own charming get-away with a private bath, a mini kitchen and beautiful water views. The post & beam barn, known as, 'The Perch' was built as a separate office/gym on the grounds. It includes a great room with a wood burning stove and on the lower level a full bath, exercise room and service bar.128 Starboard Lane is a gardener's dream when it comes to life in the spring. The Meadow in bloom is breathtaking and the Rhododendrons lining the driveway are ablaze with color.The apple orchard is amazing along with the courtyard and outdoor spaces all with their own special gardens.Don't miss this special, one-of-a-kind opportunity to buy the perfect legacy property in Osterville!

      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: 3.45% last updated on 2022-01-13

      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
      • Full Bath 5
      • Half Baths 1
      • MLS Status Active

      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: 3.45% last updated on 2022-01-13

      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$3,195,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22105797

      • Single Family
      • Garage Spaces 3
      • Full Bath 4
      • MLS Status Active
      • Village Osterville

      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 Compass

      {$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: 3.45% last updated on 2022-01-13

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

      26 Donna Barnstable MA 02655

      Barnstable, MA26 Donna Avenue

      Price$1,595,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22106670

      • Single Family
      • Full Bath 2
      • Half Baths 1
      • MLS Status Active
      • Village Osterville

      If you are looking for a turnkey Colonial home within walking distance to Osterville Village, look no further! Ideally located in a quiet neighborhood offering 3 beds, 2.5 baths and extra bonus room for sleeping or office. The kitchen offers white cabinetry, Thermador appliances, beverage fridge and double thick quartz countertops with large island and plenty of room for a large dining table. Flooded with natural light, the adjacent family room with vaulted ceilings leads out to a large Azek deck. An additional first floor front-to-back living room has a gas fireplace & built-in cabinetry with window seat overlooking the yard. Extensively renovated in 2017, updates include hardwood floors, Andersen windows, recessed lights, custom closets, 2-zone HVAC with gas heating, tankless Navien, NEST thermostats/smoke detectors, irrigation & WiFi Kohler generator. All baths are updated with a Carrara marble primary bath with steam shower. Enjoy outdoor living in the large level yard with lush grass and plantings, oversized outdoor shower, wide driveway and exquisite hardscaping with striking curb appeal. Impeccably maintained, the list of upgrades is extensive and too numerous to list.

      Listed by Jennifer A McCartin 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: 3.45% last updated on 2022-01-13

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

      42 Pond Barnstable MA 02655

      Barnstable, MA42 Pond Street

      Price$1,050,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22107214

      • Single Family
      • Garage Spaces 2
      • Full Bath 2
      • Half Baths 1
      • MLS Status Active

      Serenely tucked away in peaceful woods this 3 bed 3 bath 2000+ sqft home is a perfect invitation to peaceful living in Cape Cod, ideally located less than a ten-minute walk to fun and food on Main Street Osterville, and less than a 5-minute drive to the beach. Step into this home and into the stunning Living room with warm hardwood floors reflected in the soaring ceilings punctuated by gorgeous skylights and brimming with natural light. The elegant double-sided fireplace guides one into the Dining room and kitchen with a beautiful brick face to the now cozy home hearth. The kitchen is large and features an indoor grill with a massive hood and extractor fan. Easy access to the elevated deck with expansive views of the open yard and wooded backlot is the perfect place to entertain. Space abounds with three bedrooms and three full baths, and if storage is what you need the large basement and two-car garage will not disappoint. Accept this home's warm invitation, 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: 3.45% last updated on 2022-01-13

      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 January 20, 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.

      Testimonials

      "The top Buyers Broker on the Cape. Knows the market and the value of property better than anyone. Very ethical. Tough negotiator on behalf of his clients. Has represented me on both home and land purchases. Also have sold a property to a customer he represented, and definitely prefer having him on my side of the negotiation. Spends your money like it was his own. Cannot recommend him [...]

      Open Houses

      TIME TO TAKE A LOOK

      Browse the open house schedule today.

      View
      Blog

      STAY CURRENT

      Read about local area info.

      View