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Cape Cod Homes with a Guest House

Browse listings for homes with a guest house on the Cape. You may also be interested in viewing multigenerational homes.

Find Cape Cod Homes for Sale with a Guest House

Call Beach Realty at 508-888-4998 or contact us online with any questions or to schedule a private tour. 

227 Bridge Street Barnstable MA 02655

MLS Number 73088912

  • Residential
  • Bathrooms 5
  • Bedrooms 8
  • Square Feet 4,033

From its unparalleled location on Little Island in Osterville, this special waterfront estate overlooks the waters of West Bay and offers breathtaking water vistas from its private, elevated setting. This 2.45-acre lot features a substantial deep water dock, private sandy beach and an expansive yard. The 3,315 square foot main house is abundant in space with six bedrooms and a substantial multilevel deck. The first floor features grand living and family rooms with impressive fireplaces and water views on three sides, cook’s kitchen, dining area and a primary suite with two walk-in closets, luxurious bathroom and incredible water views. The second floor features five bedrooms, two full bathrooms and a water view balcony. The outdoor living spaces are equally impressive, with a sprawling backyard and patio areas with ample space for relaxation. A two-bedroom guest house with deck is available for overflow guests. Truly a once-in-a-lifetime opportunity to enjoy your own piece of paradise

Listed by Robert Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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227 Bridge Street Barnstable MA 02655

Barnstable, MA227 Bridge Street

Price$12,500,000

Est. Mortgage: $/month

MLS Number 22300899

  • Residential
  • Bathrooms 5
  • Bedrooms 8
  • Square Feet 4,033
  • Parking Spaces 5

From its unparalleled location on Little Island in Osterville, this special waterfront estate overlooks the sparkling waters of West Bay and offers breathtaking water vistas from its private and elevated setting. This 2.45-acre lot features a substantial deep water dock, private sandy beach and an expansive yard perfect for entertaining. Classic in design, the 3,315 square foot main house, filled with natural light, is abundant in space with six bedrooms and a substantial multilevel deck. The first floor features grand living and family rooms both with impressive fireplaces and gorgeous water views on three sides, a spacious cook's kitchen, dining area and a primary suite with two walk-in closets, luxurious bathroom and incredible water views. The second floor features five bedrooms, two full bathrooms and a water view balcony. The outdoor living spaces are equally impressive, with a sprawling backyard and patio areas providing ample space for relaxation. A two-bedroom guest house with deck is available for overflow guests. With its incomparable location, fabulous amenities, and stunning water views, this waterfront estate on Cape Cod is truly a once-in-a-lifetime opportunity to enjoy your own piece of paradise. Osterville offers beautiful beaches and landmark oceanfront estates and with its peninsular location and ample waterways, it's a boater's dream. Home to the exclusive Oyster Harbors Club and Wianno Golf Club, it's also ideal for the dedicated golfer. Spend the day sunning and swimming at Dowses Beach, then explore Osterville's quaint yet sophisticated downtown, full of great shops and charming restaurants.

Listed by Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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55 Winterset Drive Chatham MA 02633

Chatham, MA55 Winterset Drive

Price$1,795,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 22300802

  • Residential
  • Bathrooms 4
  • Bedrooms 4
  • Square Feet 4,072

Come view this special property. Deeded rights to Lovers Lake with incredible privacy with 2 adjoining lots. Perfect for a guest house and pool. Spacious living room and family room with cathedral ceilings, hardwood floors and 4 fireplaces make this home warm and inviting. 4 bedrooms 3 1/2 baths with a primary bedroom on the first and second floor. Light bright updated kitchen. Jetted tub in bath on the second floor. New boiler and hot water heater. Laundry in the lower level and one in the first floor primary bedroom. Buyers and their agent responsible for their own due diligence. Don't miss this fabulous property.

Listed by Judith L Smith of John C Ricotta & Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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468 Wianno Barnstable MA 02655

Barnstable, MA468 Wianno, Osterville

Price$10,000,000

Est. Mortgage: $/month

MLS Number 73081843

  • Residential
  • Bathrooms 8
  • Bedrooms 6
  • Square Feet 6,492

The Grand Dame of Wianno is available....this signature property has been lovingly restored to even better than in its Glory Days. The perfect home for entertaining with 6 plus bedrooms, a grand ballroom that features the largest window on Cape Cod, formal living room and dining room, an exquisite gourmet kitchen, an additional family room, home office and more. The interior elevator makes for easy access to the upstairs bedrooms. The exterior grounds are gorgeous with an exceptional in ground pool, many decks and patios and the potential for a guest house as well. Did I mention water views of East Bay, close proximity to Dowses' Beach and a short stroll to Osterville Village. A one of a kind offering!!

Listed by Witter & Witter Boston / Cape Cod Connection and Joan Witter of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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468 Wianno Avenue Barnstable MA 02655

Barnstable, MA468 Wianno Avenue

Price$10,000,000

Est. Mortgage: $/month

MLS Number 22300596

  • Residential
  • Bathrooms 8
  • Bedrooms 6
  • Square Feet 6,492
  • Parking Spaces 4

The Grand Dame of Wianno is available....this signature property has been lovingly restored to even better than in its Glory Days. The perfect home for entertaining with 6 plus bedrooms, a grand ballroom that features the largest window on Cape Cod, formal living room and dining room, an exquisite gourmet kitchen, an additional family room, home office and more. The interior elevator makes for easy access to the upstairs bedrooms. The exterior grounds are gorgeous with an exceptional in ground pool, many decks and patios and the potential for a guest house and Sport's Court. Did I mention water views of East Bay, close proximity to Dowses' Beach and a short stroll to Osterville Village. A one of a kind offering!!

Listed by W&W Boston/Cape Cod Connection and Joan Witter of Compass Massachusetts,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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23 Malabar Road Chatham MA 02633

Chatham, MA23 Malabar Road

Price$949,000

Est. Mortgage: $/month

MLS Number 73080302

  • Residential
  • Bathrooms 2
  • Bedrooms 4
  • Square Feet 2,212

Wonderfully unique opportunity in Chatham to purchase a virtually turn-key four-bedroom, two-bath home. The 8 room house totals 2,212 sq ft of finished living space with 1,547 sq ft on the first two floors and 665 sq ft of finished basement. Highlights include a lovely updated kitchen, primary bedroom on the first floor along with a guest room and two large bedrooms and a full bath on the second floor. The house has town water and natural gas fueled forced hot air and air conditioning. The bright and cheery finished basement includes a media room, a recreation room with a pool table, laundry area and storage. Outside features include a beautifully manicured lawn with in-ground irrigation, outdoor shower, storage shed and ample parking. The home would make for a terrific summer getaway or investment property. Also, please note there is an adjacent 13,920 sq ft level lot available for purchase. It is perfect for a modest one-bedroom guest house, garage/barn or pool and pool house.

Listed by The Bohman Hartung Group of Gibson Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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 TourAsk A QuestionMore Details

23 Malabar Road Chatham MA 02633

Chatham, MA23 Malabar Road

Price$949,000

Est. Mortgage: $/month

MLS Number 22300320

  • Residential
  • Bathrooms 2
  • Bedrooms 4
  • Square Feet 2,212

Wonderfully unique opportunity in Chatham to purchase a virtually turn-key four-bedroom, two-bath home. The 8 room house totals 2,212 sq ft of finished living space with 1,547 sq ft on the first two floors and 665 sq ft of finished basement. Highlights include a lovely updated kitchen, primary bedroom on the first floor along with a guest room and two large bedrooms and a full bath on the second floor. The house has town water and natural gas fueled forced hot air and air conditioning. The bright and cheery finished basement includes a media room, a recreation room with a pool table, laundry area and storage. Outside features include a beautifully manicured lawn with in-ground irrigation, outdoor shower, storage shed and ample parking. The home would make for a terrific summer getaway or investment property. Also, please note there is an adjacent 13,920 sq ft level lot available for purchase. It is perfect for a modest one-bedroom guest house, garage/barn or pool and pool house. The location in a low key established neighborhood is a short walk to the bustling West Chatham corridor of restaurants and shops and only 2 miles to downtown Chatham.

Listed by The Bohman Hartung Group of Gibson Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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 TourAsk A QuestionMore Details

504 Old Harbor Road Chatham MA 02650

MLS Number 73070365

  • Residential
  • Bathrooms 6
  • Bedrooms 8
  • Square Feet 4,859

Magnificent eight bedroom mansion from days gone by, designed by famous architect Edward Sears Read. Perched on a hill overlooking Chatham Harbor, North Beach, and the Atlantic Ocean beyond. Almost 300 feet of private sandy private beach described by an article in CNN as "one of the top 9 secret beaches in NORTH AMERICA". Three acres of land has room for expansion, a guest house, a pool, and/or a tennis court. A true forever, family compound within an easy walk to downtown Chatham or Chatham Bars Inn. Must see the whole property, inside and out, to fully appreciate the surroundings, the privacy of the three acres, the 300 feet of beach, the eight bedrooms, the six fireplaces, and the miles of views to the north, south, and east. And what a spectacular, one of a kind property owned by the same family since the 1940's.....Opinion of some people in town is that this is the nicest property in Chatham......You decide......

Listed by John Burke and Waldo Brown of William Raveis Chatham

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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 TourAsk A QuestionMore Details

504 Old Harbor Road Chatham MA 02650

Chatham, MA504 Old Harbor Road

Price$16,500,000

Est. Mortgage: $/month

MLS Number 22300106

  • Residential
  • Bathrooms 6
  • Bedrooms 8
  • Square Feet 4,859
  • Parking Spaces 15

Magnificent eight bedroom mansion from days gone by designed by Architect Edward Sears Read. Perched on a hill overlooking Chatham Harbor, North Beach, and the Atlantic Ocean beyond. Almost 300 feet of sandy private beach described by an article on CNN as ''one of the top 9 secret beaches in NORTH AMERICA''. Three acres of land has room for expansion, a guest house, a pool, and/or a tennis court. A true forever, family compound within an easy walk to downtown Chatham or Chatham Bars Inn. Must see the whole property, inside and out, to fully appreciate the surroundings, the privacy of the three acres, the 300 feet of beach, the eight bedrooms, the six fireplaces, and the miles of views to the north, south, and east. And what a spectacular, one of a kind property owned by the same family since the 1940's. Opinion of some people in town is that this is the nicest property in Chatham......You decide......

Listed by John B Burke and Ward H Brown,III of William Raveis Real Estate & Home Services

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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 TourAsk A QuestionMore Details

789 S Main Street Barnstable MA 02632

MLS Number 73053158

  • Residential
  • Bathrooms 8
  • Bedrooms 7
  • Square Feet 7,413

This extraordinary waterfront estate with magnificent water views over Centerville River and Nantucket Sound features 200 linear feet of water frontage, a private deep-water dock, and waterside boathouse. This unique offering, with its elevated coastal setting and ocean views, is enhanced with stunning landscaping and manicured lawns that wrap the .99-acre site. The 5-bedroom main residence, with 5,600 sq ft of living space, features a multi-level floor plan that is both bright and spacious and offers a living room, family room and well-equipped kitchen with dining area, breakfast nook and sitting area all providing access to the multi-tiered decks overlooking the water. Complementing the main home is a beautiful guest house with 1,794 sq ft, a large bonus room and private balcony overlooking the water. Complete with a 3-car garage and separate .38-acre parcel featuring a private, white sand beach on Nantucket Sound, this unique offering has captured the essence of seaside living.

Listed by Robert Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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 TourAsk A QuestionMore Details

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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

This site was last updated March 22, 2023 5:51 AM EDT. All properties are subject to prior sale, changes, or withdrawal.

Beach Realty Cape Cod 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.

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