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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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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

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.59% last updated on Aug 9, 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: 4.59% last updated on Aug 9, 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 02650

Price$4,500,000

Est. Mortgage: $/month

MLS Number 21805829

  • Single Family
  • Village North Chatham
  • Year Built 1734
  • Bathroom 8
  • Full Bathrooms 7

If you are looking for spectacular views you will not want to miss this exceptional estate that sits high on a hill overlooking Pleasant Bay on coveted Cotchpinicut Road. With plenty of room for guests, you will be charmed by the ambiance of this circa 1740 home with all of the updates required for today's stylish living. It features eight bedrooms including an opulent master suite and seven baths , wide pine floor boards, original paneling in the older sections, a large chef's kitchen, gas fireplaces in the den and kitchen, three wood burning fireplaces, a finished basement for the kids, separate apartment, office and man cave by the garage. With a heated inground pool, beach, two decks for entertaining, there is plenty of privacy but also great gathering places for all.

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: 4.59% last updated on Aug 9, 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: 4.59% last updated on Aug 9, 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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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: 4.59% last updated on Aug 9, 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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68 Shell, Chatham, MA 02650

Price$3,199,000

Est. Mortgage: $/month

MLS Number 21805502

  • Single Family
  • Village North Chatham
  • Year Built 1880
  • Bathroom 5
  • Full Bathrooms 4

This magnificent property boasts close to 3 acres of breathtaking, expansive views with deed beach rights directing abutting. The house is a rich history with he original cottage built for William Nickerson in 1700, main house added on in 1800 by Solomon Howes, and added onto and updated over the last 2 centuries. Completely comfortable living as all main systems updated in 2003. Unparalleled views of Pleasant Bay with Strong Island in the horizon. This is an ideal family compound opportunity with endless potential for something even more special.Now offered BELOW assessment

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: 4.59% last updated on Aug 9, 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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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

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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: 4.59% last updated on Aug 9, 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

66 Towhee, Orleans, MA 02653

Price$2,395,000

Est. Mortgage: $/month

Open House

MLS Number 21712208

  • Single Family
  • Next Open House: Sat 18th 2:00 pm - 4:00 pm
  • Village Orleans
  • Complex Other
  • Year Built 2005

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: 4.59% last updated on Aug 9, 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 & 792' of frontage 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: 4.59% last updated on Aug 9, 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

12 Ewing, Orleans, MA 02653

Price$1,650,000

Est. Mortgage: $/month

MLS Number 21801168

  • Lots and Land
  • Village Orleans
  • Acreage 1.68
  • Miles to Beach 0 - .1
  • Special List Cond None

This is a beautiful large lot on Pleasant Bay! Such a rare opportunity to build a wonderful home with salt water frontage. A high point set back from the water allows for a perfect building site. There is 153 +/- water frontage with a beach, easily accessed by way of a well worn path. Location of panhandle driveway has been mowed to see where it is located.

Listed by Orleans Village Properties, LLC

{$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: 4.59% last updated on Aug 9, 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

65 Lake, Orleans, MA 02653

Price$1,375,000

Est. Mortgage: $/month

MLS Number 21716228

  • Single Family
  • Village Orleans
  • Year Built 1979
  • Bathroom 4
  • Full Bathrooms 3

This home has it all, Prestigious Location, private assoc. sandy beach, dock & assured mooring on Pleasant Bay. Stunning home recently renovated with the finest craftsmanship, including custom built-ins, wainscoting, reconstructed kitchen with vaulted ceiling and mudroom/pantry and awaits buyer's choice of cabinets, counter tops and appliances. Newly added additional large sunlit master bedroom suite with spa bath overlooking beautiful gardens. Living room has custom built-ins, fireplace, gleaming hardwood floors and sliders out to new mahogany deck. This home has deeded access to one of South Orleans best private beaches. For the discriminating buyer wanting the very best craftsmanship in one of Orleans most prestigious locations

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: 4.59% last updated on Aug 9, 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

17 Whidah, Chatham, MA 02650

Price$1,349,000

Est. Mortgage: $/month

MLS Number 21804609

  • Single Family
  • Village North Chatham
  • Year Built 1968
  • Bathroom 5
  • Full Bathrooms 4

Are you looking for a renovated Cape Cod home with deeded rights to Pleasant Bay? Is rental income of $50,000 a year (2017) attractive to you? This lovely Cannon Hill Estates home is the answer. Sited on 1.02 acres of rolling lawns and easy maintenance grounds, this expansive Cape offers 5BRs, 4 BAs and 3500 sq ft of living space on 3 levels. Open floor plan includes renovated kitchen, great room, with vaulted ceilings and fireplace and wet bar. The walk out lower level, with full bath is perfect for teenagers or overflow. Deeded rights to sandy beach on Pleasant Bay. Possible mooring of boat.

Listed by Pine Acres 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: 4.59% last updated on Aug 9, 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

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 August 15, 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.