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Orleans, MA

As the year-round commercial and retail hub for most Outer Cape communities, Orleans, Massachusetts is the past outpost of bustling activity as the journey to the end of this peninsula begins.

Nestled between spectacular Nauset Beach on the Atlantic and tranquil Skaket Beach on Cape Cod Bay, Orleans offers something for everyone. In the quaint town center, enjoy shopping and gallery hopping, and dine on fresh local seafood. In our historic district explore museums and take in live theater performances. And in the natural beauty of its shores and forests, discover the perfect spot for a wide range of outdoor sports including fishing, boating, swimming, biking and just plain relaxing in the clean, fresh air!

For more info on Orleans MA real estate, contact Shoreland Realty Group.  Register with our site to stay up-to-date on your favorite Orleans Massachusetts home listings.  

13 Kingsbury, Orleans, MA 02653

Price$7,995,000The price has recently decreased

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 B Kinlin of Robert Paul Properties, Inc.

Shoreland Realty - Hyannis Office
1220 Route 132 Suite 8
Hyannis MA, 02601
Office: 508-771-2008

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.57% last updated on 2018-06-21

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$7,985,000The price has recently decreased

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 Paul E Grover of Robert Paul Properties, Inc.

Shoreland Realty - Hyannis Office
1220 Route 132 Suite 8
Hyannis MA, 02601
Office: 508-771-2008

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.57% last updated on 2018-06-21

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$7,985,000The 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 Paul E Grover of Robert Paul Properties, Inc.

Shoreland Realty - Hyannis Office
1220 Route 132 Suite 8
Hyannis MA, 02601
Office: 508-771-2008

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.57% last updated on 2018-06-21

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

108 Freeman, Orleans, MA 02653

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

Est. Mortgage: $/month

MLS Number 21712145

  • Single Family
  • Village Orleans
  • Year Built 2017
  • Bathroom 6
  • Full Bathrooms 4

Custom home built for sale by Cape Cod-based integrated architecture and construction firm, Polhemus Savery DaSilva (PSD). The new 4,659 sf home now under construction features an open living concept, 1st and 2nd floor master suites, and all the timeless details you'd expect in a PSD home. The acre waterfront site offers direct saltwater access, commanding water views, fabulous outdoor living, and a pool. (Disclosure: Agent has an interest in the property.)

Listed by Trainor & Ehnstrom Team of oldCape Sotheby's International Realty

Shoreland Realty - Hyannis Office
1220 Route 132 Suite 8
Hyannis MA, 02601
Office: 508-771-2008

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.57% last updated on 2018-06-21

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

40 Toms Hollow, Orleans, MA 02662

Price$4,300,000The price has recently decreased

Est. Mortgage: $/month

Open House

MLS Number 21717283

  • Single Family
  • Next Open House: Sat 30th 10:00 am - 12:00 pm
  • Village South Orleans
  • Year Built 1999
  • Bathroom 7

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 Fran I Schofield of Robert Paul Properties, Inc.

Shoreland Realty - Hyannis Office
1220 Route 132 Suite 8
Hyannis MA, 02601
Office: 508-771-2008

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.57% last updated on 2018-06-21

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

14-29-35 Twitchknot Farm - Uncle Marks, Orleans, MA 02653

Price$4,070,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21803524

  • Lots and Land
  • Village Orleans
  • Acreage 7.91
  • Miles to Beach .1 - .3
  • Special List Cond None

14 Twitchknot Farm Way and 29 & 35 Uncle Marks Way in East Orleans encompass 6.65 acres and offer an almost unheard of opportunity to create your Cape Cod legacy. Also included in the sale is a sandy beach known as 19 Smugglers Path which is accessed by a charming footpath. The gorgeous grounds provide terrific privacy. All told there are four dwellings on two parcels plus an additional buildable lot. The properties are also being offered individually: 29 Uncle Marks Way (MLS # 21803520), 35 Uncle Marks Way (MLS # 21803521), and 14 Twitchknot Farm Way (MLS # 21803522).

Listed by Trainor & Ehnstrom Team of oldCape Sotheby's International Realty

Shoreland Realty - Hyannis Office
1220 Route 132 Suite 8
Hyannis MA, 02601
Office: 508-771-2008

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.57% last updated on 2018-06-21

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

14-29-35 Twitchknot Farm - Uncle Marks, Orleans, MA 02653

Price$4,070,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21803523

  • Single Family
  • Village Orleans
  • Year Built 1920
  • Bathroom 7
  • Full Bathrooms 6

14 Twitchknot Farm Way and 29 & 35 Uncle Marks Way in East Orleans encompass 7.91 acres and offer an almost unheard of opportunity to create your Cape Cod legacy. Also included in the sale is a sandy beach known as 19 Smugglers Path which is accessed by a charming footpath. The gorgeous grounds provide terrific privacy. All told there are four dwellings on two parcels plus an additional buildable lot. The properties are also being offered individually: 29 Uncle Marks Way (MLS # 21803520), 35 Uncle Marks Way (MLS # 21803521), and 14 Twitchknot Farm Way (MLS # 21803522).

Listed by Trainor & Ehnstrom Team of oldCape Sotheby's International Realty

Shoreland Realty - Hyannis Office
1220 Route 132 Suite 8
Hyannis MA, 02601
Office: 508-771-2008

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: 4.57% last updated on 2018-06-21

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

374 Tonset, Orleans, MA 02653

Price$3,650,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21803057

  • Single Family
  • Village Orleans
  • Year Built 1916
  • Bathroom 3
  • Full Bathrooms 3

ELEVATED site provides unobstructed sweeping views of Nauset Harbor & the Outer Beach with approximately 250' frontage along the shoreline. Rambling 5 bedroom coastal home flanked by rolling lawns enjoys a commanding position to take the breezes. Open first floor layout allows easy flow from entertaining spaces out to the expansive deck. Cozy sunroom invites an afternoon nap. Great Rooms on each level can accommodate your crowd. Separate entry in-law apartment. House needs extensive renovation or buyer may consider razing. Oversized 2 car attached garage. Generator. Post & beam cottage on pilings enjoys the catbird's seat right at the water's edge. Property offered below assessed value. A choice offering. Information provided herein is considered reliable. Buyer & Buyer's agent are encouraged to verify details

Listed by Hardman-Liberles Team of oldCape Sotheby's International Realty

Shoreland Realty - Hyannis Office
1220 Route 132 Suite 8
Hyannis MA, 02601
Office: 508-771-2008

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.57% last updated on 2018-06-21

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

17 Overlook, Orleans, MA 02643

Price$3,295,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21711542

  • Single Family
  • Village East Orleans
  • Year Built 2017
  • Bathroom 6
  • Full Bathrooms 4

Debuting to the market, an exceptional 4BD/6BA home currently under construction. Thoughtfully inspired in design by the outstanding water views and location in Grandview Estates. Attention to detail will be evident through out the home, strategically combining character with impressive finishes and state-of-the-art amenities. Open main living level with gas fire place and superb views, gleaming hardwood floors, spectacular kitchen to meet any chef's needs, over-sized living room and den, grand master suites on both 1st and 2nd living levels, two additional bedrooms all en suite, stately 322 sq.ft. lounge on the 3rd level with mesmerizing saltwater views, 1st & 2nd level laundry, 3 car garage, studio & more! Association mooring, deep water access.Walk to Nauset Beach from this dream home!

Listed by Jack Bohman/ Jo-Ellen Erickson of oldCape Sotheby's International Realty

Shoreland Realty - Hyannis Office
1220 Route 132 Suite 8
Hyannis MA, 02601
Office: 508-771-2008

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.57% last updated on 2018-06-21

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

16 Thayer, Orleans, MA 02653

Price$3,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 21802750

  • Single Family
  • Village Orleans
  • Year Built 1998
  • Bathroom 6
  • Full Bathrooms 5

Spacious, salt waterfront home with open architecture overlooking Namequoit River and association DOCK. Highest quality materials used and meticulously maintained. Main house features interconnected entry hall, living room, kitchen,dining room, screened porch, and full length deck - all with water views. Second floor contains spacious master bedroom suite and two other bedrooms. Lower level has walk-out game room. Attached guest wing has kitchenette, separate first floor laundry, den, and five more bedrooms. In addition to dock with boating access to Pleasant Bay and the Atlantic, association membership includes two tennis courts and a small beachfront on Pilgrim Lake, bocce court, and tether ball. Great gathering place for friends and relatives. Pristine, move-in condition.

Listed by Chester Crabtree, III of Wilkinson & Associates R E

Shoreland Realty - Hyannis Office
1220 Route 132 Suite 8
Hyannis MA, 02601
Office: 508-771-2008

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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: 4.57% last updated on 2018-06-21

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

This site was last updated June 22, 2018. All properties are subject to prior sale, changes, or withdrawal.

Shoreland Realty 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.