Our mobile site is optimized for smaller screens.

TRY IT NO THANKS
MORE SEARCH OPTIONS

      Osterville MA Waterfront Properties

      Find the latest waterfront properties 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

      {$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.

      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

      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.

      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 22100348

      • Lots and Land
      • MLS Status Pending
      • Village Osterville
      • Topography Lot Description View
      • Acreage 8.06

      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: 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.

      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: 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.

      183 Bay Barnstable MA 02655

      Barnstable, MA183 Bay Street

      Price$6,995,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22005399

      • Single Family
      • Garage Spaces 2
      • MLS Status Pending
      • Village Osterville
      • Year Built 2016

      Magnificent seaside estate boasts exquisite architectural finishes, commanding views of North Bay, lush meadows, and private dock. Masterfully built in 2016 by Peter Boyle, this gracious residence has been meticulously designed by Ivan Bereznicki to capture sensational water and golf course views while effortlessly blending the finest craftsmanship with luxurious amenities to create an idyllic seaside retreat. Highlights include state-of-the art kitchen with superb finishes, waterside fireplaced living room, paneled library with built-ins, splendid master suite, three handsome guest bedrooms with en suite baths, and serene vistas from nearly every richly appointed room. Tucked away yet close to village amenities, this one-of-a-kind masterpiece is the pinnacle of refined coastal living.

      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: 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.

      183 Bay Barnstable MA 02655

      Barnstable, MA183 Bay Street

      Price$6,995,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22105039

      • Single Family
      • Garage Spaces 2
      • Village Osterville
      • Year Built 2016
      • Bathroom 5

      Architect designed and Custom-built Lifestyle Property. An exceptionally beautiful waterfront home located on scenic North and West Bays. Picturesque South and West facing views feature dramatic sunsets and scenic vistas. Nauticus Marina, Little Island and Oyster Harbors. Private beach and Dock. Close to the village center for a short walk to Dinner, Galleries and Shopping. Plenty of room for expansion, possibility of Pool, tennis court or a guest house.

      Listed by Debra M Caney 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:

      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.

      92 North Bay Barnstable MA 02655

      Barnstable, MA92 North Bay Road

      Price$6,250,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22000918

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

      Fabulous waterfront residence overlooking the beautiful waters of North Bay in the private gated community of Oyster Harbors. Sweeping water views greet you as you enter this stunning 6,482 square foot home featuring 6 bedrooms including 2 spacious first floor master suites, a beautifully designed kitchen, generous living and dining rooms and a stunning great room with expansive walls of windows and elevated ceilings blending indoor and outdoor living. This special property has had many upgrades and features exceptional attention to detail throughout. The lower level is finished with an entertainment room, home theater 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 the finest elements in seaside living. Information contained herein is believed to be accurate but should be independently verified by prospective buyers.

      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.

      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: 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.

      299 Eel River Barnstable MA 02655

      Barnstable, MA299 Eel River Road

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

      Est. Mortgage: $/month

      MLS Number 22102623

      • Lots and Land
      • Village Osterville
      • Acreage 1.06
      • Miles to Beach 0.1
      • Special List Cond None

      Not since Captain Kidd plied these waters off Osterville during the eighteenth century has such treasure been found. A treasure more dear you won't find these days: the smell of the ocean-infused breezes; the softness of a sandy shoreline against bare feet and the views of the sun setting over West Bay in a riotous cacophony of color. Yes, this one acre west facing fully permitted building site is a rare treasure. Create your waterfront residence and treasure the lifestyle that is so highly sought after and hard to find. The fully permitted dock for a motorized center console boat is a treasure. The house you design and build at this site is a treasure; and most importantly, the memories you create here will be treasures. Come to 299 Eel River Road to learn more. Site plan available. 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.

      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.

      25 Pine Barnstable MA 02655

      Barnstable, MA25 Pine Lane

      Price$1,100,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22104464

      • Single Family
      • MLS Status Pending
      • Village Osterville
      • Year Built 1955
      • Bathroom 2

      Mid-century Modern architecture meets Cape Cod charm! Come see this direct waterfront, one of a kind gem on Sam's Pond, only steps to Joshua's Pond. Built in 1955, this thoughtfully designed and much-loved home boasts an open floor plan, 3 bedrooms, a grand fire-placed living room, high, beamed ceilings, clerestory windows allowing for great sun exposure and connection with the outdoors, built-ins and storage space galore; a large dining room open to the vintage kitchen with a gas stovetop, double wall ovens, cork floors, lower level studio walk-out including a separate entrance, with large deck and a sprawling, private yard with direct access to the pond. This home has wonderful space and potential: restore to period splendor or update to your own taste. Perfect for year round and summer use. Stroll to the village and beaches, and enjoy all Osterville has to offer. Septic was installed in 2016 and is a 4 bedroom system. Square footage includes lower level.

      Listed by Kathy D Craig 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.

      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.

      Testimonials

      “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 [...]

      Open Houses

      TIME TO TAKE A LOOK

      Browse the open house schedule today.

      View
      Blog

      STAY CURRENT

      Read about local area info.

      View