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Pleasant Bay

Dreaming of cool summer breezes and sunshine? Discover homes near Pleasant Bay, a beautiful protected water body with access to the ocean and shoreline in Harwich, Chatham and Orleans.  Whether for a summer getaway or a permanent home, you are sure to find what you've been looking for. 

Save your favorites when you register with us today, and get notifications when similar properties are posted. Contact us for more information and to set up a showing for any listing below.

13 Kingsbury, Orleans, MA 02653

Price$9,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21602722

  • Single Family
  • Acreage 4.4
  • Village Orleans
  • Lot Size Square Feet 191664
  • Bedrooms 5

A lustrous gem in a world-class setting! Secluded 4.4-acre waterfront estate on peninsula overlooking Pleasant Bay--one of the jewels of the Eastern Seaboard. Luminous new 8,500 sf residence offers magnificent views of a bay studded with islands, cut by winding rivers, and bordered by the Outer Beach and Atlantic Ocean. Set atop an elevated bluff surrounded by 900' of private sandy beach, the residence offers sophisticated, striking design; generous yet comfortable living spaces; beautiful architectural detailing; richly variegated water views; & flawless craftsmanship. Waterside Gunite pool, spa & outdoor kitchen, accented by granite terraces & gardens, are havens for entertaining and relaxing. Boathouse and moorings offer deep water access to world-class beaches, boating & fishing on the Atlantic. Cape Cod's 5-star resort is a 5-minute boat ride away; Chatham and Orleans fine dining & shopping destinations just 7 minutes by car. Utter brilliance in an exquisite setting.

Listed by Robert Paul Properties, Inc.

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Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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

10-54 Sipson Island, Orleans, MA 02653

Price$9,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21716591

  • Single Family
  • Acreage 24.31
  • Village Orleans
  • Lot Size Square Feet 1058944
  • Bedrooms 7

HISTORIC offering! Sipson Island--a ~25-acre landmark on the eastern coast of Cape Cod--is presented for sale in its entirety for the 1st time in generations. Located on Pleasant Bay, one of Cape Cod's most beautiful embayments & an international boating & sport fishing destination, the island includes several year-round, seasonal dwellings & outbuildings; 2 boathouses; 2 docks, rolling, lightly vegetated upland; coastal bluff; & extensive private sandy beach. Peerless privacy, acreage, water views, development potential & deep water boating access to the Atlantic. Less than 90 miles & under 2-hour drive from Boston, the property is short drive to municipal airports in Hyannis, Chatham, & Provincetown on Cape Cod. A 3-minute's calm boat ride from a private dockage on the South Orleans mainland across a channel known as The Narrows, the property includes 9 island parcels & private mainland dock & parking. The ultimate in coastal cache, privacy & lifestyle opportunity.

Listed by Robert Paul Properties, Inc.

{$agent->Name}

Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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

10 Sipson Island, Orleans, MA 02653

Price$9,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21607146

  • Lots and Land
  • Village Orleans
  • Acreage 24.31
  • Miles to Beach 0 - .1
  • Special List Cond Standard

HISTORIC offering! Sipson Island--a ~25-acre landmark on the eastern coast of Cape Cod--is presented for sale in its entirety for the 1st time in generations. Located on Pleasant Bay, one of Cape Cod's most beautiful embayments & an international boating & sport fishing destination, the island includes several year-round, seasonal dwellings & outbuildings; 2 boathouses; 2 docks, rolling, lightly vegetated upland; coastal bluff; & extensive private sandy beach. Peerless privacy, acreage, water views, development potential & deep water boating access to the Atlantic. Less than 90 miles & under 2-hour drive from Boston, the property is short drive to municipal airports in Hyannis, Chatham, & Provincetown on Cape Cod. A 3-minute's calm boat ride from a private dockage on the South Orleans mainland across a channel known as The Narrows, the property includes 9 island parcels & private mainland dock & parking. The ultimate in coastal cache, privacy & lifestyle opportunity. www.sipsonisland.com

Listed by Robert Paul Properties, Inc.

{$agent->Name}

Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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

114 Cranberry, Chatham, MA 02650

Price$4,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21713699

  • Single Family
  • Acreage 1.42
  • Village North Chatham
  • Lot Size Square Feet 61855
  • Bedrooms 5

Recently completed in North Chatham on Cranberry Lane is this exceptional one of a kind luxury estate on 1.42 acres of land. Included is the Main house consisting of 6,000 s.f. on three levels, a 1,600 s.f. Guest house, an oversized gunite pool with automatic retractable cover and hot tub including an outdoor Summer kitchen and firepit. There is also a deeded path to a private sandy beach on Pleasant Bay. Property is being offered furnished and turn key. The Gambrel style Main home can sleep 14 in beds and in addition to the custom kitchen with Wolf dual fuel 6 burner stove and grill , 48'' Subzero refrigerator and Asko dishwasher there are white oak floors thruout and a theater and game room in the lower level. The Guest house sleeps 6 and has gas fireplace and vaulted ceilings.

Listed by William Raveis RE & Home Serv.

{$agent->Name}

Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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

141 Cotchpinicut, Chatham, MA 02633

Price$4,900,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21713971

  • Single Family
  • Acreage 1.03
  • Village Chatham
  • Lot Size Square Feet 44867
  • Bedrooms 8

This multi generational landmark, legacy compound is perfectly situated on one of Chatham's most sought after streets. Main house with gorgeous raised wood paneling, over sized kitchen and great room opens to lush gardens and in ground pool area perfect for entertaining family and friends. The master suite features stunning ocean views and private oversized deck. Guest house offers a spacious billiards/game room and loft area and two bedrooms. There is also an additional separate one bedroom apartment attached. This is a once in a lifetime offering at the end of a very special street. The estate is steps to a private sandy neighborhood beach. Watch the video tour to get a better perspective!

Listed by Robert Paul Properties, Inc.

{$agent->Name}

Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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

68 Shell, Chatham, MA 02650

Price$4,100,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21714176

  • Single Family
  • Acreage 2.76
  • Village North Chatham
  • Lot Size Square Feet 120226
  • Bedrooms 6

The possibilities are endless with this 1800's historic beachfront home privately set in Cannon Hills. This idyllic property sited on nearly three acres with 500 feet of beachfront offers extraordinary grounds and views of Strong island and Pleasant Bay. Renovated over the years, the home retains the charm and character of the past with original moldings, mantels, wide pine floors, beams, and original fireplaces. Updated for today's living, the property comprises a main house, attached guest suite, cabana, and multiple picturesque barns. With six bedrooms, ample indoor and outdoor living space, the home is a spectacular opportunity as is or to create a Chatham seaside retreat for generations to come.

Listed by Pine Acres Realty

{$agent->Name}

Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

Do not fill in this field:

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Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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

24 Andrew Mitchell, Chatham, MA 02650

Price$3,990,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21712569

  • Single Family
  • Acreage 1.54
  • Village North Chatham
  • Lot Size Square Feet 67082
  • Bedrooms 6

This stunning North Chatham estate was built by James Gable of Gable Building Corp. Sited on 1.54 acres of private grounds, this luxurious residence offers a stately 5,700 square foot main house, heated 2-car garage, beautifully appointed detached guest house over an additional 3-car garage, an in-ground heated pool with pool house, patio, multiple decks and deeded access to an association beach. The open concept first floor features multiple living & dining spaces, a cook's kitchen w/maple cabinets, granite counters & high-end stainless appliances, and a master suite w/private deck, master bath w/dressing room. The walk-out lower level offers a media room, gym, 1,000 bottle wine cellar w/tasting room & beautiful stonework. The mature landscape abounds with gardens & an apple orchard.

Listed by Kinlin Grover Real Estate

{$agent->Name}

Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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

328 Whidah, Chatham, MA 02633

Price$3,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21711749

  • Single Family
  • Acreage 1.18
  • Village Chatham
  • Lot Size Square Feet 51400
  • Bedrooms 5

Presiding over Bassing Harbor in Pleasant Bay this rare beachfront offering is sited on 1.18 acres in North Chatham's Cannon Hill Association. Ideally located at the end of a cul-de-sac, down a lushly landscaped driveway, the property boasts privacy and spectacular views with a private association beach accessed on the property. Immaculately presented, this five bedroom home built in 1962 and renewed over time, displays attention to detail and uncompromising views. The spacious living room with dining area and fireplace adjoins an open kitchen. A family room with cathedral ceilings and projection TV system accentuate the home's comforts. A separate wing comprises three bedrooms and two baths. The updated master suite is a sanctuary streaming with light and beautiful views. Above is an office space with a multi-use bonus space. In addition there is a whole house Natural Gas backup generator. This is a very special property and opportunity.

Listed by Pine Acres Realty

{$agent->Name}

Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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

340 Whidah, Chatham, MA 02633

Price$3,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21715530

  • Single Family
  • Acreage 1.21
  • Village Chatham
  • Lot Size Square Feet 52664
  • Bedrooms 5

''ARGONAUT''.Named for a band of heroes in Greek mythology from the ancient ship ARGO who in the years before the Trojan War helped shape the modern world, this unique WATERFRONT, 5 bedroom on two floors, 5 bathroom home is perched on a 1.2 acre lot overlooking the Atlantic Ocean, Chatham Harbor, Pleasant Bay, and Ryder's Cove. Imagine having your morning coffee on one of two large decks overlooking all of this past the manicured, professionally landscaped lawn and yard. Enjoy your own private beach with over 200 feet of water frontage protected by a Chapter 95 Waterways licensed revetment.Boating from your front yard for deep water fishing or just joy riding as moorings are available here. Numerous upgrades over the years on this one owner 3817 sq ft home in this extraordinary setting..

Listed by William Raveis RE & Home Serv.

{$agent->Name}

Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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

66 Towhee, Orleans, MA 02653

Price$2,495,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21712208

  • Single Family
  • Acreage 0.62
  • Village Orleans
  • Lot Size Square Feet 27185
  • Bedrooms 4

This property is like living in a 5 star resort. Prestigious location with deeded access to a sandy stretch of beach on Pleasant Bay. Meticulously designed with unprecedented craftsmanship and amenities. Lower Ground level features a professional bar set-up with beer on tap, state of the art wine cooler, pool room, and large media area. Outside includes an in-ground saltwater pool, surrounding stone patio, outside kitchen with industrial sized pizza oven & putting green. For the discriminating buyer looking for the best the Cape has to offer. Photos do not do justice to this amazing home. Please look at video.

Listed by oldCape Sotheby's International Realty

{$agent->Name}

Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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

279 Woodland, Chatham, MA 02650

Price$2,495,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21710034

  • Single Family
  • Acreage 0.59
  • Village North Chatham
  • Lot Size Square Feet 25700
  • Bedrooms 3

Waterfront home on Ryder's Cove with deep water access for boating, fishing clamming, beautiful sunsets and the mooring area is right in front. Walk via the private path to the assoc. beach. This luxury home is truly elegant offering the perfect balance between formality and livability. The interior is enhanced with Brazilian cherry floors, custom cabinetry and beautiful mill-work. This amazing home features a first floor master suite and the living room is spacious and beautiful with a coffered ceiling, built-ins, wet bar and multiple sliders to the deck great for entertaining overlooking the water. Sunny finished lower level is just as glamorous with lots of glass to enjoy the views. Family room, exercise room, bath with steam shower and game room.Exterior is enhanced with a custom Japanese water fall, patios, gardens, heated driveway. Buyers agent to verify all information . Please take a moment to view the virtual tour.

Listed by Kinlin Grover Real Estate

{$agent->Name}

Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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

293 Whidah, Chatham, MA 02650

Price$1,695,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21711631

  • Single Family
  • Acreage 0.96
  • Village North Chatham
  • Lot Size Square Feet 41818
  • Bedrooms 4

Price just reduced $100,000 for this Impeccably maintained home with 4 bedrooms & 5 bath is perfect as a primary or seasonal residence, comfortably providing multiple living areas for family & friends. This well-designed home has a 1st-floor en-suite master bedroom w/tray ceiling, a Cooks Kitchen opens to two distinct living areas all having French Doors to access the deck with views of Ryders Cove and Bassing Harbor. In addition, it has a sunroom w/shiplap ceiling, den, 3 fireplaces, first-floor laundry & 2-car attached garage with unfinished attic. The walkout lower level has two finished rooms with built-ins. As a bonus, you have 2 outdoor showers, irrigation on its own well, & central A/C. Deeded rights to a private beach only .1 mi from home. Rental $6,500/wk & room for a pool. Pride of ownership is reflected in the thoughtfully landscaped and well-maintained residence makes this a Must See Home! Please take the 3D self-guided tour for additional informatiomn and floor plans.

Listed by Kinlin Grover Real Estate

{$agent->Name}

Cape Cod Chatelains
525 South Street
Hyannis MA, 02601
Office: 508.737.4080

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-07-13

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 Cape Cod Chatelains are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Cape Cod Chatelains shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated March 7, 2017. All properties are subject to prior sale, changes, or withdrawal.

Cape Cod Chatelains 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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Client Testimonials

  Agnes helped us find a house when we lived out of state. Not easy! She handled that so well and worked so hard that we never considered anyone else when looking for our new Cape home. She and Ed (and Ned ) are true professionals. We HIGHLY recommend the Chatelains for any Cape real estate needs.

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