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Cape Cod MA Homes with Guest House

Scroll down to find current homes with a guest house for sale in the Greater Cape Cod, MA area. Discover a variety of beautiful properties in towns like Truro, Eastham, Wellfleet, and many others.

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97 Tilipi, Chatham, MA 02633

Price$19,995,000

Est. Mortgage: $/month

MLS Number 21306159

  • Single Family
  • Acreage 1.9
  • Village Chatham
  • Lot Size Square Feet 82764
  • Bedrooms 6

Boasting one of the most spectacular properties on the Cape Cod shoreline, this shingle-clad home is poised on 1.9 acres and majestically resides over the Atlantic Ocean, Monomoy Islands and Nantucket Sound. With 10,974 square feet of living space spanning three levels, the six bedroom estate has simply breathtaking views, manicured grounds and a glorious stone pool pavilion. The enchanting home is designed with a circular motif and gleams of pure elegance and includes multiple family gathering rooms, a banquet size dining room, chef's kitchen, 11 seat theater, an opulent wine cave and a circular one bedroom carriage house for guests or staff. A Creston smart home system controls security, electronic gate, lighting, audio, and driveway and pool heat with a touch of a button. idyllic property is incomparable on Cape Cod.

Listed by Chris Rhinesmith of Pine Acres Realty

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Provincetown Office
405 Commercial Street
Provincetown MA, 02567
Office: 508.487.6111

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.46% last updated on Mar 1, 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
  • 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 Team Guthrie - Mabile of Robert Paul Properties, Inc.

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Provincetown Office
405 Commercial Street
Provincetown MA, 02567
Office: 508.487.6111

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.46% last updated on Mar 1, 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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17 Bayview, Harwich, MA 02645

Price$4,600,000

Est. Mortgage: $/month

MLS Number 21715121

  • Single Family
  • Acreage 1.57
  • Village Harwich
  • Lot Size Square Feet 68389
  • Bedrooms 3

17 Bayview Rd being sold with 49 Snow Inn Rd for a total asking price of 4.6 Million. Here is a rare opportunity to invest in over an acre and a half of property that is close to town, near the beach, has deep water frontage and access with a dock; and is also secluded and private and peaceful. 17 Bayview is over an acre and a half with a guest/caretaker cottage already there for updating and plenty of extra space to add your harbor view dream home. 49 Snow Inn is a harbor front gem that cannot be duplicated. 2 beds and one and one half baths directly on the water with a deep water dock. The best Cape Cod has to offer is here. Come and take a look.

Listed by Eric Scott Hellstrom of Peterson Realty Inc.

{$agent->Name}

Provincetown Office
405 Commercial Street
Provincetown MA, 02567
Office: 508.487.6111

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.46% last updated on Mar 1, 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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161 Uncle Barneys, Dennis, MA 02670

Price$4,500,000

Est. Mortgage: $/month

MLS Number 21800903

  • Single Family
  • Acreage 0.54
  • Village West Dennis
  • Lot Size Square Feet 23522
  • Bedrooms 4

Spectacular Wrinkle Point waterfront crafted home on Bass River. Sensational sunset views. Custom architecture home has 5685 sq ft in main house with 4 Bedrooms and 4.5 bathrooms.Private accessible Guest suite over 2 car garage. First floor Master bedroom with potential for handicapped access, elegant bath and ample closet space.Home features include Coffered ceilings, warm hardwood floors, high end Anderson ''A series'' windows. Ideal kitchen open to gazebo style room. Floor plan offers 3 crafted stairway cases to second floor. Additional 720 sq ft finished attic bunk area capable of sleeping 6-8.Lower level has 1420 sq ft living area for your gym or additional family room.Two home theaters with surround sound as well as an audio system throughout the house. Well maintained grounds that that leads to your 105 ft deep water dock. 30 foot flagpole with exterior landscaping and lighting.

Listed by Jamie Regan of Robert Paul Properties, Inc.

{$agent->Name}

Provincetown Office
405 Commercial Street
Provincetown MA, 02567
Office: 508.487.6111

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.46% last updated on Mar 1, 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
  • Acreage 3.84
  • Village South Orleans
  • Lot Size Square Feet 167270
  • Bedrooms 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 Fran I Schofield of Robert Paul Properties, Inc.

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Provincetown Office
405 Commercial Street
Provincetown MA, 02567
Office: 508.487.6111

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.46% last updated on Mar 1, 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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210 South, Yarmouth, MA 02664

Price$3,995,000

Est. Mortgage: $/month

MLS Number 21717128

  • Single Family
  • Acreage 2.02
  • Village Bass River
  • Lot Size Square Feet 87991
  • Bedrooms 5

Beautifully sited at the mouth of the Bass River with spectacular panoramic views of Nantucket Sound and West Dennis Beach is this stunning custom built 5-bedroom home with views from every room. This gracious residence incorporates a top of the line kitchen with adjoining family room using extensive wood moldings, elegant coffered ceilings, architectural columns and broad use of windows to enjoy the ocean views. Stunning Brazilian Cherry floors throughout, spacious first floor master suite, 2nd floor den with fireplace and guest quarters above detached 2 car garage are additional highlights of this unique and outstanding ocean front home. For the serious mariner this property offers an outstanding shared deep-water dock with the open ocean less than 1/10 of a nautical mile away.

Listed by Robert B Kinlin of Robert Paul Properties, Inc.

{$agent->Name}

Provincetown Office
405 Commercial Street
Provincetown MA, 02567
Office: 508.487.6111

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.46% last updated on Mar 1, 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
  • Lot Size Square Feet 1
  • Bedrooms 6
  • Bathroom 8

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 Shane K Masaschi of Kinlin Grover Real Estate

{$agent->Name}

Provincetown Office
405 Commercial Street
Provincetown MA, 02567
Office: 508.487.6111

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.46% last updated on Mar 1, 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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535 Stage Harbor, Chatham, MA 02633

Price$3,750,000

Est. Mortgage: $/month

MLS Number 21714909

  • Single Family
  • Acreage 2.07
  • Village Chatham
  • Lot Size Square Feet 90169
  • Bedrooms 6

Location is everything...Iconic family estate overlooking Stage Harbor and on the loop to town and Lighthouse Beach. A welcoming wide front porch with lovely vistas of the sailboats in the Harbor and sweeping green lawns and coastal gardens sets the tone for casual Cape Cod elegance inside. Renovated over the years, the Main house boasts spacious rooms, updated kitchen, formal dining and over sized living room with fireplace. A newly renovated guest house offers two baths, two sleeping areas, full kitchen and private deck. Additional outer building includes a home office/artist studio. The property includes waterfront accessed via a path. The house easily expands for large family gatherings or can feel intimate in the off season. A special place.

Listed by Lori L Fanning Smith of Pine Acres Realty

{$agent->Name}

Provincetown Office
405 Commercial Street
Provincetown MA, 02567
Office: 508.487.6111

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.46% last updated on Mar 1, 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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1 Bluff, Truro, MA 02652

Price$3,595,000

Est. Mortgage: $/month

MLS Number 21716972

  • Single Family
  • Acreage 1.08
  • Village North Truro
  • Lot Size Square Feet 47045
  • Bedrooms 4

Overlooking the beautiful ocean on a sandy bluff sits this sophisticated waterfront home. Collaborative efforts have transformed this residence into a stunning modern oasis with 5000 sq. ft. and beautifully balanced living areas all oriented toward the water. A magnificent kitchen, dining, and great room anchor the home and access the wrap around deck. There is a mud room, home office, butlers pantry, laundry room and 2 story foyer that complete the main floor. The first floor master suite with a spa like bath showcase water vistas of the sea and beyond. The second floor features 2 bedrooms with ensuite baths, family room with private deck and den. There is a guest suite over the garage, inground pool and a private stairway to your own white sandy beach...the ultimate waterfront home.

Listed by Cindy Houlihan of Robert Paul Properties, Inc.

{$agent->Name}

Provincetown Office
405 Commercial Street
Provincetown MA, 02567
Office: 508.487.6111

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.46% last updated on Mar 1, 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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84 Hiram Pond, Dennis, MA 02638

Price$3,500,000

Est. Mortgage: $/month

Pending

MLS Number 21715522

  • Single Family
  • Acreage 0.46
  • Village Dennis
  • Lot Size Square Feet 20038
  • Bedrooms 4

STUNNING does not fully describe this spectacular waterfront on glorious Cape Cod Bay! Magnificent views abound in every direction. Completely renovated, features include the relaxing sunken living room with fireplace and walls of glass to capture this incredible setting; a new chefs kitchen offers every convenience with splashy decor, appliances, lighting, and drop dead gorgeous views from everywhere; a huge master suite with a beautifully finished private bath and sun deck overlooking the Bay; three additional bedrooms, 2 with private baths; a fun loft area which kids and guests will love; a cozy den; garage; and THE BEST PRIVATE BEACH IN DENNIS! Absolutely nothing to be done but move in and enjoy. Coming fully furnished and equipped. This is a magnificent offering not to be missed!

Listed by Betsy & Gerry Ciarcia of Home*Land Realty

{$agent->Name}

Provincetown Office
405 Commercial Street
Provincetown MA, 02567
Office: 508.487.6111

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.46% last updated on Mar 1, 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 SeasCape Realty, Inc. are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor SeasCape Realty, Inc. shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated April 24, 2018. All properties are subject to prior sale, changes, or withdrawal.

SeasCape Realty, Inc. 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.