Cape Cod Homes with a Guest House

Here you'll find all Cape Cod homes for sale with a guest house.

Contact Cape Coastal Sotheby's International Realty at 508.477.6688 or online for more information or to schedule a private tour.

373 Bridge Chatham MA 02633

Chatham, MA373 Bridge Street

Price$6,995,000

Est. Mortgage: $/month

MLS Number 22000133

  • Single Family
  • Village Chatham
  • Year Built 2019
  • Bathroom 9
  • Full Bathrooms 8

Boasting one of Chatham's most sought-after Light House Beach locations, this stunning estate set on 1.54 acres is a true family compound. The brand new 5 BR main house is masterfully designed with a relaxed open layout combining elegance and sophistication. The first floor has a central kitchen, dining room, multiple living spaces with an en-suite bedroom. The upper floor offers a sumptuous master bedroom-suite with a family room and three additional en-suite bedrooms. The lower level has an entertainment room, family room, wine storage and full bath. The guest house built in 2003 offers striking spaces, three fireplaces, a first and second floor master suite, and an indoor lap pool. The estate is enhanced with lushly landscaped grounds, a pool, and a detached garage. (Note: Furniture Photos in Listing sheet are a combo of virtually and past staging efforts)

Listed by Chris Rhinesmith of Compass

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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11 Library Chatham MA 02633

Chatham, MA11 Library Lane

Price$2,995,000

Est. Mortgage: $/month

MLS Number 22000127

  • Single Family
  • Village Chatham
  • Year Built 1881
  • Bathroom 8
  • Full Bathrooms 5

This extraordinary in-town residence sits graciously above Chatham Village offering 4,238 square feet of generously proportioned living space with six bedrooms. Winner of the 2008 Chatham Preservation Awards, this Victorian residence was originally built in 1881 by Daniel Webster Nickerson and completely renovated in 2007 maintaining traditional period features and custom woodwork throughout. The main level features a chef's kitchen with top of the line appliances, family room, dining room, living room, office/ en-suite bedroom and two half baths. There are three more bedrooms on the second floor plus a third-floor bedroom with views of the Oyster Pond. Above the two-car garage is a private guest suite. The lower level offers a family room, bath and wine cellar. 10K/ wk rental history.

Listed by Chris Rhinesmith of Compass

$
$
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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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155 & 157 Bridge Chatham MA 02633

Chatham, MA155 & 157 Bridge Street

Price$4,595,000

Est. Mortgage: $/month

MLS Number 22000128

  • 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 Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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333-359 Seapuit Barnstable MA 02655

Barnstable, MA333-359 Seapuit Road

Price$14,995,000

Est. Mortgage: $/month

MLS Number 21908511

  • Single Family
  • Village Osterville
  • Year Built 1914
  • Bathroom 4
  • Full Bathrooms 3

Prominently sited on Bog Pond with direct access to North Bay and beyond to Nantucket Sound, this storied heritage estate is set on over eight pristine acres creating an unmatched setting for extraordinary living. Surrounded by captivating water views, this remarkable property offers a rare opportunity for complete seclusion while in the heart of Osterville. Built in 1914, the five-bedroom main house is a time-honored lodge with magnificent water views and handsome period detail. The guest house is simply perfect for waterside entertaining and relaxed getaways. Located in one of Osterville's finest estate neighborhoods, this property boasts dual frontage on two pristine bodies of salt and freshwater, protected deep water dock, rolling lawns, lush gardens, and swimming pool. This exquisite offering presents a unique opportunity to create an unrivaled generational compound with effortless proximity to renowned village shops, restaurants, marinas and Wianno and Oyster Harbors clubs. Please note that this property is available as a compound or two individual waterfront home sites.

Listed by Paul E Grover of Robert Paul Properties, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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230 Seapuit River Barnstable MA 02655

Barnstable, MA230 Seapuit River Road

Price$3,495,000

Est. Mortgage: $/month

MLS Number 21908486

  • Single Family
  • Village Osterville
  • Year Built 1925
  • Bathroom 8
  • Full Bathrooms 6

This sophisticated and charming shingle-style Cape set on a beautifully landscaped private 2+ acre lot awaits your arrival. Built in 1925 and fully renovated, this home is located in the private community of Oyster Harbors. The residence is the epitome of Cape Cod living with 5 plus bedrooms and a gunite pool. The location is a short distance from Osterville village and all the village has to offer and is close to Hyannis and the Barnstable airport. An elegant first floor master suite includes multiple closets and a stunning bath with access to the pool and outside shower. Enjoy the chef's kitchen when entertaining either pool side or in the elegant dining room. Spend time relaxing in the spacious living room with a wood burning fireplace or in the cozy den. Each bedroom features its own private bath. A custom boat storage barn, a separate parking garage and a spacious guest suite are just steps from the pool and tennis court. The exceptional stonework, rose garden, perennials and the stately Cooper Beech trees make this truly an estate to enjoy. Please verify all information herein.

Listed by Bonnie Zappala Britt of Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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189 Main Orleans MA 02653

Orleans, MA189 Main Street

Price$729,900

Est. Mortgage: $/month

MLS Number 21908464

  • Single Family
  • Village Orleans
  • Year Built 1984
  • Bathroom 5
  • Full Bathrooms 5

INVESTOR'S DREAM!! Amazing value!! 2 HOUSES !!Large acre plus lot minutes to Nauset Beach in East Orleans. Huge Post & Beam(1984)3 BR 2 BA on PRIVATE WAY-(Loomis Ln) is situated well behind 3 Br 3 Bath newer Cape(2005) Each has private title V septics and lot can be condo'ed ! Price is amazing for this location! Build a dream home and rehab guest house~ the possibilities here are endless!!

Listed by Nancy Morris of Kinlin Grover Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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41 Pond View Mashpee MA 02649

Mashpee, MA41 Pond View Drive

Price$299,900

Est. Mortgage: $/month

Pending

MLS Number 21908395

  • Single Family
  • Village Mashpee
  • Year Built 1994
  • Bathroom 3
  • Full Bathrooms 3

Lots of potential in this priced to sell property located in Winslow Farms. Needs work but well worth the effort for the value in this neighborhood. New roof within the last 5 years. Interior has a spacious open floor plan, 1st floor bedroom, laundry area and full bath, 2nd floor has 2 bedrooms which includes a master w/ private bath & balcony. Lower level is semi finished with a full bath and 3 rooms, kitchenette and private entrance, would make a great guest suite or home office but definitely needs work!! Enclosed back porch provides even more potential for additional living space. Property has a nice level fenced back yard, with combination shed and chicken coop.Buyer and or their agent should do their own due diligence as Information deemed reliable but not guaranteed.

Listed by Cynthia B Eisen of EXIT Cape Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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308 Shore Falmouth MA 02540

Falmouth, MA308 Shore Street

Price$1,100,000

Est. Mortgage: $/month

MLS Number 21908246

  • Single Family
  • Village Falmouth
  • Year Built 1822
  • Bathroom 4
  • Full Bathrooms 3

Smell the salty air and listen to the sounds of the ocean from this charming antique home located just 2 homes away from Surf Drive Beach. This historic colonial features 5+ bedrooms, 3 1/2 baths, including a first floor en-suite bedroom, beautiful wood flooring and lovely ocean views from 2 second floor bedrooms. The oversized dining area is perfect for entertaining and the 4 season sunroom offers a fantastic place to relax in those summer evenings. Two new boilers were installed in 2018, and kitchen has been updated with stainless steel appliances. The guest suite over the garage offers even more living space for your overflow company. With easy access to the bike path, ferries and Falmouth Village, this home is the perfect blend of Cape Cod today and the past.

Listed by Karen M Burton of Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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229 Main Chatham MA 02633

Chatham, MA229 Main Street

Price$1,795,000

Est. Mortgage: $/month

MLS Number 21908195

  • Single Family
  • Village Chatham
  • Year Built 1880
  • Bathroom 5
  • Full Bathrooms 3

Steps from the sand of famed Lighthouse Beach, via a public access point across the street, this 5BR, 3 BA home offers first and 2nd floor views of the Atlantic. Separate 2BR, 1 BA guest house located on the property. Located on desirable Main Street in Chatham. Lots of space for family and friends. Excellent rental history. New 7BR Title V septic installed in 2017. Walk to restaurants, shops and beaches. Can't beat the location. Please verify all information contained herein.

Listed by Jessica A King of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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312 Bridge Barnstable MA 02655

Barnstable, MA312 Bridge Street

Price$2,550,000

Est. Mortgage: $/month

MLS Number 21908162

  • Single Family
  • Village Osterville
  • Year Built 1952
  • Bathroom 5
  • Full Bathrooms 4

Located in the Little Island neighborhood of Osterville is this traditional Cape style home perfectly sited on a 1.09 acre parcel with beautiful water views over North Bay. This well-maintained residence offers 4,692 sq. ft. of living space with five bedrooms. Formal living spaces combine with an updated, light filled great room and custom kitchen to create the ideal blend of comfort and formality. The home also features a formal living room, spacious dining room, cozy family room and master bedroom suite all with access to the back deck and the tranquil water views. A second master suite with attached office, two additional bedrooms, stunning sunroom and office or bonus room complete the first floor. The finished space above the garage offers a private guest suite. Special features include beautiful wood floors, custom built-ins, over-sized windows and two fireplaces. Enjoy a tranquil setting with beautiful gardens, mature plantings, rolling lawns, an in-ground pool and deeded beach rights. Information contained herein is believed to be accurate but should be independently verified by prospective buyers.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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300 Stage Neck Chatham MA 02633

Chatham, MA300 Stage Neck Road

Price$14,900,000

Est. Mortgage: $/month

MLS Number 21908121

  • Single Family
  • Village Chatham
  • Year Built 2001
  • Bathroom 9
  • Full Bathrooms 5

Seaside sophistication in a world class setting!The lure of breathtaking water vistas and the appeal of luxurious appointments can be found in this grand waterfront property known as ''Viewpoint Estate.'' An unparalleled location, the secluded 5.2-acre setting offers panoramic water vistas of Oyster Pond River, Hardings Beach and Nantucket Sound. Set atop an elevated bluff surrounded by 1,130 feet of shoreline, the owners painstakingly created this spectacular estate where privacy was paramount, and design incorporated the ideal balance of comfort and elegance. The 10,350 sq. ft. main residence offers sophisticated, striking design, generous yet comfortable living spaces, beautiful architectural detailing, richly variegated water views and flawless craftsmanship. Interior spaces include a welcoming foyer, stunning great room and formal dining room along with a fabulous chef's kitchen with top of the line appliances and a large breakfast area, and a mahogany clad private bar and office. The upper level features five bedrooms including the stunning master suite and a bunkroom over the garage. The lower level offers a custom designed theater room with billiards area and sixth en suite bedroom. An infinity-edge pool, multiple outdoor seating areas and path to the water's edge are havens for entertaining or relaxing and soaking in the sweeping views. Also included is a beautifully designed 1,673 square foot guest house featuring two separate apartments ideal for extended family and friends. 'Viewpoint Estate' offering an unparalleled lifestyle is a legacy property for generations to come.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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101 Gibson Orleans MA 02653

Orleans, MA101 Gibson Road

Price$2,100,000

Est. Mortgage: $/month

MLS Number 21908066

  • Single Family
  • Village Orleans
  • Year Built 2020
  • Bathroom 6
  • Full Bathrooms 4

Two beautiful homes by Eastward Companies comprise this unique East Orleans compound on an estate-sized corner lot with easy saltwater access via nearby Asa's Landing. The main residence is a brand new 3700 sq ft classic center chimney cape with an outstanding interior layout plus all of the appointments and amenities you would expect from this esteemed local builder. Four bedroom suites including a first floor master with fireplace and a dedicated second floor guest suite with private entrance. The fireplaced great room offers multiple gathering spaces, the kitchen features a 10' center island and butler's pantry. Fine custom details and finish work throughout, gas utilities. At the far end of the level acre+ grounds you will find the charming, remodeled, 720 sq ft year-round guest cottage. It enjoys a lovely setting and is perfect for long term guests or as a true in-law house. There are myriad options for a pool,fire pit and outdoor enjoyment areas at this bona fide family compound in the heart of East Orleans. Expected completion is Spring 2020. Note: Listing details pertain to the main house. Guest house square footage and details are not reflected in the MLS listing

Listed by Jeffrey E Cusack of Cove Road Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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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 Coastal Sotheby's International Realty are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Cape Coastal Sotheby's International Realty shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated January 29, 2020. All properties are subject to prior sale, changes, or withdrawal.

Cape Coastal Sotheby's International 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.