Upper Cape Homes with a Guest House

Find homes for sale with a guest house in the Upper Cape towns of Bourne, Falmouth, Mashpee & Sandwich MA. 

Cape Cod Homes with a Guest House

Give Ermine Lovell Real Estate a call at 508-548-0703 or contact us online with any questions or if you'd like to see any of these properties in person.

72 Oceanview Barnstable MA 02635

Barnstable, MA72 Oceanview Avenue

Price$2,475,000

Est. Mortgage: $/month

Pending

MLS Number 22101991

  • Single Family
  • Garage Spaces 2
  • MLS Status Pending
  • Village Cotuit
  • Year Built 1830

This pristine Colonial features amenities that everyone will adore! A newly renovated kitchen with custom cabinetry, built-in TV, pot filler, granite counters, seating for 8 & top of the line appliances. The dining room features a gas fireplace, and bay window. With four living spaces; living room, family room, den, and sunroom, the first floor is perfect for entertaining. The family room & den boast beautiful custom-built ins. The living room has a gas fireplace, making this house comfortable year-round. Enjoy the breeze in the three seasons sunroom overlooking the beautifully landscaped and lush backyard. A bedroom w/ an ensuite completes the first floor. 3 bedrooms on the 2nd floor each w/ full bath. The Master bedroom has a custom walk-in closet, steam shower and access to a 2nd floor deck.The fully heated and air conditioned 2 story guest house (2 bed septic) was rebuilt in 2016. The Guest House has one large bedroom (sleeps 10), large screen TV, surround sound & ceiling fan. The bathroom has a double vanity, 2 toilets & shower/changing area. A 2nd exterior door leads to 1 of 2 outdoor showers. A large 2 car garage w/ utility room & built-in storage completes this building.

Listed by Greg Coutu of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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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45 Hardings Chatham MA 02633

Chatham, MA45 Hardings Lane

Price$2,500,000

Est. Mortgage: $/month

Open House

MLS Number 22102020

  • Single Family
  • Next Open House: Sat 05/8 12:00 pm. to 2:00 pm.
  • Garage Spaces 2
  • MLS Status Active
  • Village Chatham

This idyllic property is in a coveted Chatham location with deeded saltwater access. The main house and separate guest house encompass 3/4 of an acre on a quiet cul-de-sac just off the Loop. With five bedrooms and room for a pool, this light-filled home will be a backdrop for countless gatherings and memories. So close to downtown, yet you feel like you're a million miles away. With deeded rights to Mill Pond (and a potential mooring), you can spend the day on the water kayaking, paddle-boarding, or heading off to Nantucket Sound. Stage Harbor is also nearby. The expansive ranch features an open kitchen and dining room, fireplaced living room, family room with built-in cabinets, office, three bedrooms, including a luxe master suite, and a finished basement. The separate guest house includes two bedrooms, two baths, living room, kitchenette, outdoor shower, and two-car garage. In the same family since it was built, this first-time offering has been well-maintained, including many updates. From enjoying quiet afternoons reading a book or lounging on the deck, to festive celebrations, this is truly a quintessential Cape Cod home.

Listed by Harry M Cutts and Sarah Keith of William Raveis RE & Home Serv.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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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86 & 90 Freeman Orleans MA 02653

Orleans, MA86 & 90 Freeman Lane

Price$3,995,000

Est. Mortgage: $/month

MLS Number 22101951

  • Single Family
  • Garage Spaces 2
  • MLS Status Active
  • Village Orleans
  • Year Built 1986

Spectacular Snow Point Location. One of the most breathtaking parcels of waterfront land left on Cape Cod. Rare offering encompassing a charming 4 br 4 1/2 bath home with a large bonus space in a finished walkout lower level. 180 degree unobstructed views from most rooms. Property includes abutting lot (90 Freeman) totaling 1.8 acres with 460 feet of salt water frontage. 90 Freeman has already been perc tested and has a buildable envelope. One can renovate existing house at 86 Freeman and build a pool, guest house, etc. on 90 Freeman per conservation & health dept. approvals or rebuild a larger compound including 90 Freeman lot. The options are many! Steps down to the water's edge where you can moor your boat with access to Nauset Harbor and Nauset Beach. Also you can Kayak or paddle board and explore the Cove and Harbor. Deeded rights to pristine Snow Point Assoc. private beach. Please note abutting lots (10 & 12 Causeway) are also for sale. Buyer or Buyer's agent to confirm any or all information. No Drive-bys. Owner in residence.

Listed by Alberti Team of Gibson Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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$14,800,000

Est. Mortgage: $/month

MLS Number 22101792

  • Single Family
  • Garage Spaces 3
  • MLS Status Active
  • Village Chatham
  • Year Built 2001

Welcome to Viewpoint - one of the most significant waterfront estates in all of New England. Sited high atop a dramatic bluff to enjoy spectacular and commanding views over Nantucket Sound, Viewpoint is the result of a multi-year collaboration with top architects, builders and landscape designers. With over 1200 feet of direct access shoreline, this legacy property boasts nearly 6 acres of unprecedented privacy as a long gated driveway winds past a guest house and arrives in the cobblestone motor court, where the stunning main house is first revealed. The classic shingle style residence was thoughtfully designed for both grand entertaining and casual everyday family living alike. Modern systems and amenities blend with timeless architectural details. The resort-like grounds include expansive lawns, a spectacular infinity-edge pool, cabana, fire pit, meandering trails and an incredible mahogany boardwalk leading to the water's edge. Viewpoint is a pleasure to show, by appointment only.

Listed by Brian W Dougherty of Compass Massachusetts, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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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3799 Main Brewster MA 02631

Brewster, MA3799 Main Street

Price$1,395,000

Est. Mortgage: $/month

Pending

MLS Number 22101662

  • Single Family
  • Garage Spaces 3
  • MLS Status Pending
  • Village Brewster
  • Year Built 1760

This Cape Cod landmark in historic Brewster has been totally renovated and expanded while maintaining all its historic charm and distinction. Original moldings, beams and fireplaces have been carefully preserved. The home contains classic Cape Cod architecture, newly constructed overtones, is in move-incondition and located close to the bay and ocean beaches. In addition to the main house, there was a noted small antique shop and early American art gallery, which has been redesigned for use as additionalprivate living space, guest house or professional home office with garage. This special property is centrally located on a private site with space for a pool, set back off Old King's Highway Historic District; a designated road of historic homes found winding along several Cape Cod towns. It provides easy access to great year-round local amenities and is a short distance to Nickerson State Park. The original home was once featured in Old House Interiors magazine for its charm and beauty; now gracefully enhanced formodern living.

Listed by Derek J Greene of The Greene Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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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46, 47, 53 Little Beach Chatham MA 02633

MLS Number 22101407

  • Single Family
  • MLS Status Active
  • Village Chatham
  • Year Built 1941
  • Bathroom 4

Prominently sited in the sought-after beach enclave of Morris Island, this iconic compound includes three beachfront cottages with glorious ocean views and direct beach access. Evoking relaxed summers of yesteryear, these quintessential Cape cottages can be enjoyed as offered or can be the ultimate setting for a new home and guest house offering magnificent water views in a serene setting. Take a short stroll to town or simply relax while enjoying breathtaking sunrises and sunsets from the waterside decks. #53 is configured as a three-bedroom cottage with an enormous loft. #47 is configured as a two-bedroom cottage with a spacious loft for guests. #46 is configured as a one-bedroom cottage that has approved building plans for a new two-bedroom home. This rare offering provides an incredible setting to kick off your shoes and bask in the simple yet stunning beauty of Chatham.

Listed by Paul E Grover and Team Guthrie - Mabile of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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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46 Little Beach Chatham MA 02633

Chatham, MA46 Little Beach Road

Price$995,000

Est. Mortgage: $/month

MLS Number 22101215

  • Single Family
  • MLS Status Active
  • Village Chatham
  • Year Built 1941
  • Bathroom 1

Bask in sweeping ocean views and salty sea breezes from this quintessential beachside one bedroom cottage with loft. Located in the private, sought-after beach enclave of Morris Island, this property can be enjoyed as offered or be the ultimate setting for a new home with glorious water views and beach access. Take a short stroll to town or simply relax while enjoying breathtaking sunrises and sunsets from the waterside deck. This offering can be the perfect guest house for #47 or #53 Little Beach Road or purchase all three properties to create an unrivaled seaside compound. Approved architectural plans to convey with sale.

Listed by Paul E Grover and Team Guthrie - Mabile of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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

5 Monument Bourne MA 02553

Bourne, MA5 Monument Avenue

Price$850,000

Est. Mortgage: $/month

Pending

MLS Number 22101174

  • Single Family
  • MLS Status Pending
  • Village Monument Beach
  • Year Built 1886
  • Bathroom 4

Waterviews abound in this gorgeous 7 bedroom home overlooking Chester Park and Phinneys Harbor. Nostalgia is defined as a sentimental longing or wistful affection for the past, typically for a period or place with happy personal associations. This home will surely evoke those feelings. Lovingly maintained by the current owners for the last 30 years, perhaps it is now time for your family to enjoy the spacious rooms and amazing sun porch where you'll watch the kids and grandkids play tennis or run around the park on the town amenities. Kayak...swim...sunsets...this home is a treasure. The first floor features a kitchen, dining room, library, office, living room with wood burning fireplace, half bath and the sun porch with unbelievable views. There are 4 bedrooms and a bath on the second floor. The third floor has 3 more bedrooms and bath. Full basement with laundry and half bath plus storage for the kayaks & beach toys. Roof new 2020. New septic will be installed before closing. So many special features: wood floors, decorative fireplace, the dining room window...I could go on and on. Once known as the Bay Breeze Guest House on the Water. Come and wander!

Listed by Colleen C Kilfoil of A Cape House.com

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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

306 Old Comers Chatham MA 02633

Chatham, MA306 Old Comers Road

Price$1,340,000

Est. Mortgage: $/month

MLS Number 22100799

  • Single Family
  • Garage Spaces 1
  • MLS Status Active
  • Village Chatham
  • Year Built 1976

Room for a pool and a guest house! (1.25 acres) Enjoy watching the wild life on a fresh water pond! This well built home offers a sunny southern exposure and large windows with an ever changing view. The house is roomy and the floor plan invites open plan living. A large wrap around deck encourages outdoor living. There is a home office in the basement. Three bedrooms include a first floor master suite and two additional over sized bedrooms upstairs. The lot is private and landscaped with flowering trees and shrubs including a nice selection of perennials. The location of this home is a quarter mile to Ryders Cove. The quality of this local builders own home will impress. It is meticulously maintained with updated mechanicals and air conditioning. Come make it yours!

Listed by Kathleen Phelan of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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

300 Stage Neck Chatham MA 02633

Chatham, MA300 Stage Neck Road

Price$16,800,000

Est. Mortgage: $/month

MLS Number 22100597

  • Single Family
  • Garage Spaces 3
  • MLS Status Active
  • Village Chatham
  • Year Built 2001

Welcome to Viewpoint - one of the most significant waterfront estates in all of New England. Sited high atop a dramatic bluff to enjoy spectacular and commanding views over Nantucket Sound, Viewpoint is the result of a multi-year collaboration with top architects, builders and landscape designers. With over 1200 feet of direct access shoreline, this legacy property boasts nearly 7 acres of unprecedented privacy as a long gated driveway winds past a guest house and arrives in the cobblestone motor court, where the stunning main house is first revealed. The classic shingle style residence was thoughtfully designed for both grand entertaining and casual everyday family living alike. Modern systems and amenities blend with timeless architectural details. The resort-like grounds include expansive lawns, a spectacular infinity-edge pool, cabana, fire pit, meandering trails and an incredible mahogany boardwalk leading to the water's edge. Viewpoint is a pleasure to show, by appointment only.

Listed by Brian W Dougherty of Compass Massachusetts, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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

333 Seapuit Barnstable MA 02655

Barnstable, MA333 Seapuit Road

Price$7,950,000

Est. Mortgage: $/month

MLS Number 22100361

  • Single Family
  • Garage Spaces 3
  • MLS Status Active
  • Village Osterville
  • Year Built 1914

Prominently sited on a protected cove with direct access to North Bay and beyond to Nantucket Sound, this storied heritage estate is set on over 3.5 acres creating an unmatched setting for extraordinary living. Surrounded by captivating water views, this remarkable property offers a rare opportunity for complete seclusion 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, 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 an adjoining 4.01 acre parcel with deep water dock is available for purchase.

Listed by Paul E Grover and Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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

122 Pinquickset Cove Barnstable MA 02635

MLS Number 22100050

  • Single Family
  • Garage Spaces 3
  • MLS Status Active
  • Village Cotuit
  • Year Built 2005

Custom-built in 2008, this magnificent 7.6 acre landmark estate overlooks the beautiful waters of Pinquickset Cove. Located in the quintessential seaside village of Cotuit, the elegant main house features distinctive architectural details including soaring ceilings, hand-painted tiles, etched glass doors, European hardwood, barnboard floors, and custom millwork throughout. Interior spaces are oriented toward the stunning water views and filled with abundant natural light, creating a sophisticated yet comfortable home. The property offers a separate guest house/studio, infinity pool, formal gardens, lush landscaping, and detached three-car garage with guest quarters.

Listed by Paul E Grover of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 2021
* 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

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

This site was last updated May 7, 2021. All properties are subject to prior sale, changes, or withdrawal.

Ermine Lovell Real Estate, LLC 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.