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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. 

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13 Kingsbury, Orleans, MA 02653

Price$7,995,000

Est. Mortgage: $/month

MLS Number 21602722

  • Single Family
  • Village Orleans
  • Year Built 2012
  • Bathroom 6
  • Full Bathrooms 4

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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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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10 Sipson Island, Orleans, MA 02653

Price$7,985,000

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.

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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10-54 Sipson Island, Orleans, MA 02653

Price$7,985,000

Est. Mortgage: $/month

MLS Number 21716591

  • Single Family
  • Village Orleans
  • Year Built 1979
  • Bathroom 4
  • Full Bathrooms 4

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.

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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114 Cranberry, Chatham, MA 02650

Price$4,995,000

Est. Mortgage: $/month

MLS Number 21802938

  • Single Family
  • Village North Chatham
  • Year Built 2017
  • Bathroom 9
  • Full Bathrooms 8

''Cranberry Manor'' is the epitome of luxury living on Cape Cod. This exquisite estate is privately situated down a winding lane in North Chatham. From the minute you enter the dramatic front foyer you will be impressed by the quality and attention to detail thru out. From the furniture quality trim, doors and windows to the 8''white oak flooring with natural finish thru out. Open kitchen with Fantasy Brown marble counter tops and Wolf, Subzero and Asko appliances. In addition there is a home theater, game room and gym in the lower level which opens up to the custom expansive pool area including outdoor kitchen, hot tub, outdoor theater and path to a sandy beach on Pleasant Bay. Adjacent to the home and pool is a guest home of similar quality for overflow or guests. Central a/c and gas hea of course and a 400 amp electrical service. There is also a 22kw Generac back up power system if ever needed. Under "other documents" is an extensive specification sheet for the property. Over 1.4 acres for professionally landscaped property with irrigation and stunning stone walls. The pool is surrounded by wrought iron fencing.

Listed by William Raveis RE & Home Serv.

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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141 Cotchpinicut, Chatham, MA 02633

Price$4,900,000

Est. Mortgage: $/month

MLS Number 21713971

  • Single Family
  • Village Chatham
  • Year Built 1739
  • Bathroom 7
  • Full Bathrooms 7

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.

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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40 Toms Hollow, Orleans, MA 02662

Price$4,300,000

Est. Mortgage: $/month

MLS Number 21717283

  • Single Family
  • Village South Orleans
  • Year Built 1999
  • Bathroom 7
  • Full Bathrooms 6

Cape Cod Cosmopolitan! A sandy lane winds through woods and fields to this remarkable waterfront estate on magnificent Little Pleasant Bay. With 4 acres of rolling woodland, boathouse/cabana and 170'-long private sandy beach frontage on Cape Cod's largest estuary, the property combines urban sophistication with Cape Cod character.A circular seashell drive curves before the gray-shingled center-entrance Colonial. A two-story foyer announces the cathedraled great room beyond whose vivid views and chic surroundings form the home's centerpiece. Flanking the great room is a sleek, state-of-the art kitchen accented with natural brass hardware, custom cabinetry, and cool quartz countertops. An adjoining dining area with wood-burning hearth affords beautiful bay views, and opens to an enclosed porch and wrap-around deck. Gray-and-white-washed oak plank floors unite the rooms with contemporary flair. A private first floor master suite occupies the opposite wing, with generous bedroom, sharp bath, private deck and beautiful views. The second level hosts three ensuite bedrooms, a loft for reading or media, and private deck with excellent bay views. The finished walkout lower level provides extensive bonus space for recreation, exercise, guest quarters, and other uses. A three-car garage, angled off the main house, is the understory for a private guest suite hosting two-bedrooms, full bath, kitchenette, dining area, living area, and spacious deck overlooking the bay. The natural, 4-acre setting offers myriad sites for an inground pool, coastal walks, play areas. The beachside cabana, with water and power, enhances beachside recreation and entertaining. With up-to-the-minute style, exceptional privacy, beautiful bay front location, and excellent rental history, 40 Tom's Hollow perfectly blends cosmopolitan, contemporary and coastal living.

Listed by Robert Paul Properties, Inc.

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

24 Andrew Mitchell Ln, Chatham, MA 02650

Price$3,990,000

Est. Mortgage: $/month

MLS Number 21802245

  • Single Family
  • Village North Chatham
  • Year Built 2003
  • Bathroom 8
  • Full Bathrooms 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

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

32 Old Salt Works, Chatham, MA 02633

Price$2,999,000

Est. Mortgage: $/month

MLS Number 21711273

  • Single Family
  • Village Chatham
  • Year Built 1957
  • Bathroom 1
  • Full Bathrooms 1

While this property has much history* behind it, it currently offers an acre of land, a small cottage, plus space for a sizable home. It's not in the flood plain & is situated higher than most lots on the waterfront in the association. There is some shoreline erosion and the possibility of a suitable revetment as the property meets three specific requirements. In the meantime, the seller has continuous approval for renourishment of the bank.* In 1917, with our entry into the war, the US Navy constructed several coastal patrol air stations along the eastern seaboard to counter the threat posed by Germany's submarine fleet - one was this area along the coastline of Eastward Pt. Cement landing pads for Blimps used to track subs are still visible on property. Assoc Dock, Beach and Picnic are

Listed by Pine Acres Realty

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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66 Towhee, Orleans, MA 02653

Price$2,495,000

Est. Mortgage: $/month

MLS Number 21712208

  • Single Family
  • Village Orleans
  • Complex Other
  • Year Built 2005
  • Bathroom 5

This property has it all, Lifestyle, Luxury and Location in this stunning home steps from Pleasant bay beach. An association mooring is available for boating & fishing. Entertain family and friends like a 5* resort. 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. This property has all the benefits of a beach property without the erosion or flood problems. For the discriminating buyer looking for the best the Cape has to offer. Photos do not do justice to this amazing home. Please view the video

Listed by oldCape Sotheby's International Realty

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

279 Woodland, Chatham, MA 02650

Price$2,495,000

Est. Mortgage: $/month

MLS Number 21710034

  • Single Family
  • Village North Chatham
  • Year Built 2005
  • Bathroom 6
  • Full Bathrooms 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

{$office->Name}

Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

137-135 Portanimicut, Orleans, MA 02653

Price$2,188,000

Est. Mortgage: $/month

MLS Number 21802725

  • Single Family
  • Village Orleans
  • Year Built 2010
  • Bathroom 7
  • Full Bathrooms 6

Waterfront family compound on Pleasant Bay. Two houses, pool, and sandy beach. The main house constructed in 2010 has lovely waterviews and awaits your finishing touches. The updated guest house also has beautiful waterviews plus an inviting screened porch. Five bedrooms and six and one-half bathrooms in all provide ample room for friends and family. Easy access to town landing with boat launch. Numerous conservation trails nearby. Hop, skip, and a jump to downtown Chatham and Orleans for restaurants and shopping. Wake up to gorgeous sunrises and delight in the amazing natural surroundings. See attached video walk-through. (Disclosure: Owner is a licensed Massachusetts broker.)

Listed by oldCape Sotheby's International Realty

{$office->Name}

Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

77 Keziahs, Orleans, MA 02653

Price$1,950,000

Est. Mortgage: $/month

MLS Number 21802863

  • Single Family
  • Village Orleans
  • Year Built 1926
  • Bathroom 2
  • Full Bathrooms 1

Fabulous 2 acre waterfront family property known as ''The Point'' with a delightful 4 bedroom ''Cottage'' with its original interior woodworking!Incredible privacy & fabulous forever views from ''The River'' to Pleasant Bay!Boaters will love the original Boat House & Private Dock with deep water access to Nauset Beach & the Ocean!This very special one of a kind property has been in the same family for generations!

Listed by William Raveis RE & Home Serv.

{$office->Name}

Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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 June 20, 2018. 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.