and narrow your search. If you have fewer than 200 results, you can save your search.

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.

Remember to register with us to save your favorite listings and for email notifications when similar properties are posted. Already have an account with us? Log in!

Contact us for more information & to schedule a showing.

97 Tilipi, Chatham, MA 02633

Price$17,500,000

Est. Mortgage: $/month

MLS Number 21306159

  • Single Family
  • Village Chatham
  • Year Built 2010
  • Bathroom 10
  • Full Bathrooms 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

{$office->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: 4.52% last updated on Jul 19, 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

18 Snow Inn, Harwich, MA 02646

Price$9,995,000

Est. Mortgage: $/month

MLS Number 21804506

  • Single Family
  • Village Harwich Port
  • Year Built 2018
  • Bathroom 9
  • Full Bathrooms 7

An extraordinarily elegant, yet casual home defined by an impressive array of amenities, conveniences and thoughtful luxuries. Enjoy sweeping Nantucket Sound views from high atop the bluff of this 1.65 acre estate. The centerpiece of this 5 bedroom, 6.5 bath, 6,041 sq foot ''smart'' house is a spectacular gourmet kitchen. Shiplap cathedral ceilings adorn the great room where guests can relax by the fireplace to enjoy the mesmerizing ocean views. Each bedroom has its own luxurious private bath including the two master suites on both living levels. The expansive finished lower level includes a private gym, full bath, and a great room with a custom bar. A large yard, salt water pool, outdoor fireplace, grill and a custom pool cabana put an exclamation point on this coastal living masterpiece. These views include the ever changing views of Nantucket Sound or the serene in-ground saltwater pool and outdoor living patio area. Custom LED lighting enhances the stone wall by the outdoor fireplace while the pool provides its own brilliant show of lighting effects when the sun begins to set. Each of the five bedrooms have been uniquely designed with luxurious private baths. This includes two grand master suites on both living levels each with expansive walk-in closets and magnificent master baths. The expansive lower level has been finished to include a private gym, full bath, great room with custom bar ideal for game or media room. There is a unique outdoor area, off the great room, designed for practicing yoga, meditation, massage, etc. To experience residing at 18 Snow Inn Road is to live the quintessential luxury lifestyle on Cape Cod ... a lifestyle and home which would easily transform from a casual family day around the pool to a black tie evening affair.

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

{$office->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: 4.52% last updated on Jul 19, 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

47 Commercial, Provincetown, MA 02657

Price$6,495,000

Est. Mortgage: $/month

MLS Number 21805054

  • Single Family
  • Village Provincetown
  • Year Built 1800
  • Bathroom 5
  • Full Bathrooms 5

Located in the heart of the West End, Labrador Landing is an exceptional waterfront compound with expansive views of Provincetown Harbor, Long Point and beyond. Quality craftsmanship is evident in the distinctive 4br/3ba 3-story Residence, floated from Long Point, which includes a chef's kitchen, 3 fireplaces, and an office area with water views. The wisteria trimmed 1br/1ba 2-story Cottage is fully equipped and has water views from each level. The cantilevered 1br/1ba Boathouse enjoys unobstructed water views and combines vintage architectural details with modern amenities, plus a sleeping loft. All surrounded by mature plantings, brick patios and a waterfront deck with private beachfront staircase. Onsite parking. This one of a kind property is backed by an unparalleled rental history.

Listed by Brett E Holmes of Kinlin Grover Real Estate

{$office->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: 4.52% last updated on Jul 19, 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

155 & 157 Bridge, Chatham, MA 02633

Price$4,995,000

Est. Mortgage: $/month

MLS Number 21803466

  • Single Family
  • Village Chatham
  • Year Built 1980
  • Bathroom 9
  • Full Bathrooms 7

This remarkable waterfront location overlooks the Mitchell River and Mill Pond and presents a multitude of possibilities for development or renovation. Privately situated within mature landscaping on 2.8 acres with 900 feet of waterfront footage, this current family compound comprises a five bedroom, four and a half bath main house with an inground swimming pool. On a separate parcel resides a three bedroom, two and a half bath, spacious guest house with a tennis court. This is a perfect venue to create a family retreat for generations to come, yet there is also the possibility to subdivide the two lots and develop two brand new waterfront homes in one of Chatham's most picturesque settings.

Listed by Chris Rhinesmith of Pine Acres Realty

{$office->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: 4.52% last updated on Jul 19, 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

114 Cranberry, Chatham, MA 02650

Price$4,995,000

Est. Mortgage: $/month

Pending

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 Ward H Brown, III of William Raveis RE & Home Serv.

{$office->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: 4.52% last updated on Jul 19, 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

369 Old Harbor, Chatham, MA 02633

Price$4,950,000

Est. Mortgage: $/month

MLS Number 21803306

  • Single Family
  • Village Chatham
  • Year Built 1839
  • Bathroom 22
  • Full Bathrooms 20

The ultimate Chatham, Cape Cod experience. This private 1.77 acre compound with multiple historic buildings and lovely manicured grounds and pool could be your family retreat. Includes a modern home adjacent to 369 Old Harbor, located at 36 Manamock Rd. A short stroll to Chatham's Main Street famous for shops, galleries and fine and fun dining. Near sandy ocean beaches, golf, theater, island ferries and everything wonderful to do on the Cape. Your family and guests will enjoy luxury accommodations. Elegant sunny dining room is the perfect sunny spot to entertain. The experience here is all about this amazing location and all that Cape Cod offers. Ample off street parking, furnished. Currently licensed and operating as a B&B Inn. Many possibilities. Business Financials available.

Listed by Carol M Edmondson of Cape Cod Village Realty

{$office->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: 4.52% last updated on Jul 19, 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 Bayview, Harwich, MA 02645

Price$4,600,000

Est. Mortgage: $/month

MLS Number 21715121

  • Single Family
  • Village Harwich
  • Year Built 1952
  • Bathroom 3
  • Full Bathrooms 2

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.

{$office->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: 4.52% last updated on Jul 19, 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

161 Uncle Barneys, Dennis, MA 02670

Price$4,500,000

Est. Mortgage: $/month

MLS Number 21800903

  • Single Family
  • Village West Dennis
  • Year Built 2013
  • Bathroom 6
  • Full Bathrooms 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.

{$office->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: 4.52% last updated on Jul 19, 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

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 Fran I Schofield of Robert Paul Properties, Inc.

{$office->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: 4.52% last updated on Jul 19, 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

7 Harbour, Provincetown, MA 02657

Price$4,300,000

Est. Mortgage: $/month

MLS Number 21804567

  • Single Family
  • Village Provincetown
  • Year Built 2010
  • Bathroom 6
  • Full Bathrooms 5

The legend and light of Cape Cod fill this stunning five bedroom beachfront home with uninterrupted views from Lieutenant's Island to the tip of Provincetown, giving unequalled privacy and a kind of casual elegance that cannot be found elsewhere. Situated on nearly an acre of land, this custom home boasts superior construction and quality finishes. The landscaping has been thoughtfully designed by award winning Landscape Architect Keith LeBlanc to create magnificent outdoor spaces featuring a large private bluestone patio and native plants that enhance the breathtaking views of Cape Cod Bay with mature dunes dappled by Rosa Rugosa. The traditional design of the home offers grand living spaces that bring in the stunning views and that magical Cape Cod light through two levels of windows and French doors. A custom interior by an Elle Decor A-List Interior Designer features a stone foyer that leads to a large dining room open on one side to an eat-in chef's kitchen with a private garden, and on the other to a spacious, view filled living room with a large stone wood-burning fireplace and coffered ceiling. The French doors open from the living room to a beachfront deck with panoramic views and a retractable awning. The kitchen features a Wolf six burner range, Sub-Zero refrigerator and a butler's pantry. A door from the kitchen provides access to the bluestone patio for easy and gracious entertaining. A first floor guest room with a spa like en-suite bath and walk in closet also has French doors to a private beachfront deck. The upstairs master suite epitomizes luxury. The room has a private deck with breathtaking views of Cape Cod Bay, gas fireplace, beautiful bath with bay window overlooking the Bay, and large walk in closet. Also off the ample second floor center hall are three additional bedrooms and two additional baths. Other property features include: cedar shingle roof, fine moldings, beautiful finish carpentry, custom lighting fixtures, one car garage with a finished room and bathroom above, full basement for storage, outside shower, security system, central air, central sound system, generator, and mature landscaping.

Listed by Emily Flax of Atlantic Bay Sotheby's Int'l R

{$office->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: 4.52% last updated on Jul 19, 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 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 July 21, 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.