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.

63 Commercial Street Provincetown MA 02657

Provincetown, MA63 Commercial Street

Price$7,900,000

Est. Mortgage: $/month

MLS Number 22204367

  • Residential
  • Bedrooms 7
  • Bathroom 7
  • Square Feet 4,049
  • Parking Spaces 1

With its signature corner bay turret overlooking the harbor, the Viewpoint is among the more prominent West End waterfront homes in Provincetown. Total living area of 4,000 sq. ft. 4 BR/3.5 bath main house extends from the waterfront to the attached 3 BR/3 bath guest house on the street side with a rooftop deck. The home was completely reconstructed and redesigned during the 33 years of the current ownership. All three floors have decks which provide stunning views,, particularly from the third floor master bedroom's five full-window turret with views of the historic Captain Jack's Wharf and extending from Wood End to Long Point, Truro and beyond. The first floor living area features two fireplaces, cherry floors, wainscoting, paneled walls, plaster walls and finials, custom stairway, kitchen with custom cabinetry, farmer's sink, subzero refrigerator and double oven Wolf stove. Limestone counters. Multiple possibilities exist for this compound including owner's residence with guest or caretaker's quarters or excellent rental generation. Chapter 91 license. Town sewer. Whole house generator. All utilities are separate for each unit. Listing broker is the owner

Listed by Bill P Dougal and Robert A O'Malley of Beachfront Realty

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$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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99 Uncle Albert's Circle Chatham MA 02633

Chatham, MA99 Uncle Albert's Circle

Price$9,995,000

Est. Mortgage: $/month

MLS Number 22204168

  • Residential
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,786
  • Town Chatham

Waterfront property on the Oyster Pond with an existing 2 bedroom home and the potential to add an additional 4 bedroom structure on this spectacular 1.4 acre parcel that has been in the family for over 70 years and it is the site of the last working farm in Chatham. The perfect Main House and Guest house scenario awaits your imagination and architectural creativity. As you enter the property down a winding lane you will be amazed at the expansive water views of the coveted Oyster Pond. The existing year round home was built in 2004 and it has an open floor plan with a wonderful kitchen, living room and dining room. There is a first and a second floor bedroom and also a office/den on the second floor. There is a finished basement and also a two car garage on this lower level. There is also a separate barn that has an additional one car garage and workshop and was built in 2021. Enjoy your sunsets from the beautiful wrap around deck and enjoy all of the extreme privacy this property has to offer.

Listed by Rick Smith of Gibson Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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626 River Road Barnstable MA 02648

Barnstable, MA626 River Road

Price$699,000

Est. Mortgage: $/month

MLS Number 22203995

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,568
  • Parking Spaces 4

New Price! This charming 4 bedrm, 2 bath contemporary Cape sits on a beautiful wooded 1.07 acre lot. It offers the potential for a pool, studio or guest house. As you step inside you are immediately aware of the high quality of workmanship and the materials used. There are hardwood floors and tile throughout the 1st floor. It has a wonderful open floor plan that leads you from the spacious living room with gas fireplace into the well appointed kitchen and dining area which opens onto a fabulous four season sun room. Through the sliding doors you step out onto a large deck where you can enjoy your natural sanctuary with mature plantings, raised bed and handsome stone garden wall. Also on the first floor is a guest or primary bedroom with an en suite bathroom. Upstairs you will find a large front to back master bedroom with plenty of storage, sitting area and gleaming hard wood floors. It has direct access to the upstairs bath. Two other bedrooms are on the 2nd floor, one offering egress by way of an exterior staircase. In 2021 a Bosch energy efficient heating system was installed. The heated 2 car garage offers plenty of space for a workshop. This home is an excellent value!

Listed by Maureen C Carven of Kinlin Grover Compass

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$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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3401 Main Street Barnstable MA 02630

Barnstable, MA3401 Main Street

Price$1,600,000

Est. Mortgage: $/month

MLS Number 22202802

  • Residential
  • Bedrooms 8
  • Bathroom 8
  • Square Feet 5,011
  • Town Barnstable

One of the true gems of Route 6A/Old Kings Highway. This 17 rooms beauty features hardwood floors, 4 fireplaces some with ornate marble work, fenced area and meditation garden. Relax on the farmer's porch as guests did for years when this home was used at a guest house. A short stroll to Barnstable Harbor, beach and restaurants. A 2 bedroom in-law allows privacy from the main part of the house.

Listed by Kevin J Ryan of J. O'Loughlin Realty

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$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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43 Morris Island Road Chatham MA 02633

Chatham, MA43 Morris Island Road

Price$12,600,000

Est. Mortgage: $/month

MLS Number 22202441

  • Residential
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 5,861
  • Parking Spaces 2

Just a 1/2 mile from charming downtown Chatham lies a spectacular estate at 43 Morris Island Rd. Overlooking the Atlantic Ocean, this compound sits 23 feet above sea level with commanding, unobstructed views of the Atlantic Ocean. There are over 1.6 acres of manicured lawn and landscaping plus acres of sand dunes making this the best of Cape Cod beachfront living. The main house has over 5,100 square feet and was designed by renowned architect Kent Duckham. There are expansive views of Lighthouse Beach, North Beach, and the ocean from every room on the first and second levels. Upstairs there is a special sitting room and balcony to enjoy the ever-changing landscapes. The second level also includes a 440 sq. ft. light-filled art/studio with great views of Chatham Light to the north and Monomoy island to the south. In the lower level, there is a 1,000 bottle wine cellar, a theater, and a gym. In addition, there is a sweet gem of a guest house, just steps from the main residence. Please see Clark Engineering's report and Boxbrownie's rendering for an inground pool looking out over the dunes.

Listed by Jeffrey S Marcus of Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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108 Cotchpinicut Road Chatham MA 02650

Chatham, MA108 Cotchpinicut Road

Price$16,500,000

Est. Mortgage: $/month

Pending

MLS Number 22200926

  • Residential
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 7,200
  • Parking Spaces 20

Few properties along the New England coast are as special and as significant as High Scatteree, the classic North Chatham summer home perched high above Pleasant Bay with breathtaking Atlantic Ocean views. Sited behind tall and established hedges for the ultimate in privacy, a gracious winding drive welcomes guests to the 7 bedroom Main House, which is surrounded by several acres of lush lawns and gardens. Pathways meander past a clay tennis court and through a private arboretum of specimen trees to the 2 bedroom Guest House, which overlooks a stunning seaside rose garden. The deep water dock, boathouse and private beach complement the property's many resort-like amenities. Thoughtfully updated and expanded several times by top builders and craftsmen, High Scatteree blends timeless architecture with modern systems. Ideal for large gatherings or intimate weekends away, time spent at this once-in-a-lifetime opportunity will rejuvenate and inspire. A pleasure to show, by appointment.

Listed by Brian W Dougherty of Compass Massachusetts,LLC

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$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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134 Shore Drive West Mashpee MA 02649

Mashpee, MA134 Shore Drive West

Price$7,900,000

Est. Mortgage: $/month

Pending

MLS Number 22200817

  • Residential
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 4,569
  • Parking Spaces 6

GLITTERING blues and emerald greens as far as the eye can see. An oceanfront gem with sweeping views of Nantucket Sound from Hyannis Port to Martha's Vineyard, and overlooking the magnificent greens of New Seabury's Ocean Course--the ''Pebble Beach of the East.'' Privately set at southerly tip of exclusive Seaside village, this coastal home is dramatic and luxurious yet comfortable and relaxed. Walls of glass offer vast vistas of azure ocean, verdant greens and technicolor sunsets. The spectacular open floor plan provides a perfect setting for family living and high-end entertaining, while a fully equipped guest house offers private quarters for friends and family. The heated gunite pool and spa are perfection after a day on the links or at your private beach on Nantucket Sound. A short walk to the Country Club at New Seabury and close to highways, shopping, restaurants, and world-class destinations, this beachfront estate is resort living at its best and a legacy home for the generations.

Listed by Paul E Grover and Fran I Schofield of Berkshire Hathaway HomeServices Robert Paul Properties

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$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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835 Sea View Avenue Barnstable MA 02655

Barnstable, MA835 Sea View Avenue

Price$30,000,000

Est. Mortgage: $/month

MLS Number 22200155

  • Residential
  • Bedrooms 7
  • Bathroom 14
  • Square Feet 15,500
  • Town Barnstable

Set on Osterville's exclusive Sea View Avenue with commanding views over Nantucket Sound and an unprecedented 280 feet of private sandy beach, a once-in-a-lifetime coastal oasis awaits. Magnificent landscaping sets the stage, with specimen trees and lush plantings that offer total privacy across 3.66 acres. Designed in perfect harmony with its surroundings, virtually every room has ocean views and direct access to the outdoors. A thoughtful layout divides the residence into a main house and attached guest house with a total of 7 en suite bedrooms. Outdoor living is highlighted by a resort-style swimming pool, summer kitchen, and expansive terrace for sunbathing and al fresco dining. Additional amenities include a 5,000-bottle wine cellar, golf simulator, gym, massage room, 7 garage spaces, and a separate staff house. Located in one of New England's most sought-after waterfront communities, this grand estate is minutes away from everything Osterville has to offer, yet a world apart.

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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87 Beach Road Orleans MA 02653

Orleans, MA87 Beach Road

Price$9,999,500

Est. Mortgage: $/month

MLS Number 22107060

  • Residential
  • Bedrooms 9
  • Bathroom 10
  • Square Feet 11,657
  • Town Orleans

Located just over the hill from world renowned Nauset Beach in the village of East Orleans, Cape Cod, Massachusetts, USA is ''87 Beach Road '' A true Cape Cod Estate with over 10 acres of manicured grounds. The main residence - 11,657 square feet of living space, 21 rooms, 9 bedrooms, 9 full baths, and one-half bath. No cost was spared in the design and construction of ''87 Beach Road ''with only the finest of materials and craftsmen used. The residence offers numerous amenities - in-home office with hide-away secret closet, wine cellar, sauna, 2 lane bowling alley, home theater, gym, music room, study, wet bars, custom kitchens, multi fireplaces, numerous custom built-ins. The estate has a 4-car garage with loft, art studio, pool house and custom pool, greenhouse, 4 stall barn with loft, 1 bedroom guest house, scenic pond, tennis courts, basketball court, volleyball court, horseshoe pit, walking trails and gated entry. A completely self-contained estate located in East Orleans, Cape Cod, Massachusetts, USA

Listed by Pothier/Leonard LUXRECapeCod of Gibson Sotheby's International Realty

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%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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34 & 52 Caillouet Lane Barnstable MA 02655

Barnstable, MA34 & 52 Caillouet Lane

Price$13,500,000

Est. Mortgage: $/month

Pending

MLS Number 22106688

  • Residential
  • Bedrooms 8
  • Bathroom 9
  • Square Feet 8,230
  • Parking Spaces 6

Spectacular waterfront estate, with sweeping views of East Bay and Nantucket Sound, is distinguished by masterful design, meticulous attention to detail and a magnificent setting. This sophisticated property, nestled within 3.09 acres with 200 feet of water frontage, features main and guest houses, an in-ground gunite pool with pool house and a private dock with direct access to the Sound. The stunning five-bedroom main house, completely renovated in 2020, offers over 5,700 square feet of living space with water views from most rooms. Infused with natural light and the beautiful vistas, the interior of the house has a floor plan ideally suited for entertaining, both grand and intimate. Beyond the welcoming foyer, generously proportioned spaces have a graceful flow blending modern and traditional styles. Granite countertops, custom cabinetry, and top-of-the-line appliances fill the gourmet kitchen which opens into a fabulous family room. The open floor plan continues into formal living and dining rooms, connecting the main level to the outside patios, pool and meticulously landscaped grounds. A superb primary suite on the first floor offers an adjacent office with exterior access, and the second floor offers a charming sitting area, spacious media/game room and four bedrooms with stunning water views. The separate guest house with 2,500 square feet, three bedrooms and a finished walk out basement completes this incredible offering. This seaside estate affords the utmost privacy yet offers proximity to the village of Osterville with its boutique shops and fine dining. Experience an exceptional lifestyle from this one-of-a kind waterfront estate! The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

Listed by Robert B Kinlin and Tom P Foley of Berkshire Hathaway HomeServices Robert Paul Properties

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$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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251 Green Dunes Drive Barnstable MA 02647

Barnstable, MA251 Green Dunes Drive

Price$17,000,000

Est. Mortgage: $/month

MLS Number 22106436

  • Residential
  • Bedrooms 8
  • Bathroom 11
  • Square Feet 9,678
  • Parking Spaces 10

This is the ultimate Cape Cod luxurious private gated compound. Vibrant rolling lawns contrast with rare Cape Cod heathlands. An unprecedented 2600ft of sandy beach frontage on Nantucket sound and tidal pools of Halls Creek. This Bertman designed home with porte-cochere, rotunda and 4-story tower portend exceptional construction, attention to detail and opulent interior. The focal point is the great room w 20' wall of windows, southern exposure and unending views. Adjacent is the dining room and chefs kitchen with glistening water views, blue granite & impressive oval waterfront breakfast area. Off the kitchen is the secluded family room. The west wing has 2 large ensuite bedrooms w walls of glass. Next is your Private Luxury Waterfront Spa with three walls of glass, huge pool, sauna, full bath and private gym. Up the grand staircase are 2 more ensuite bedrooms w private balconies. The primary bedroom wing has open sitting area and office. A pair of doors access the private inner sanctuary with opulent mesmerizing Waterfront View's from an oval wall of glass. Huge closets, built-ins and a lavish bath. Continued... Opposite the cobblestone courtyard is the original 1920s secluded waterfront carriage house with huge private backyard. Originally for horses it has been thoughtfully converted to 6 car garage with 3 bedroom 2 bath guest house and caretakers quarters. All with amazing waterfront views. This lovingly maintained estate represents a unique opportunity to acquire a truly inspirational generational home. Information deemed to be accurate, buyers/buyers agents to confirm all information hearin.

Listed by Jonathan A Matel of William Raveis RE & Home Serv.

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$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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 Lane Orleans MA 02653

Orleans, MA86 & 90 Freeman Lane

Price$3,995,000

Est. Mortgage: $/month

MLS Number 22101951

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3,379
  • Town Orleans

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. Consistent with Article V, Cooperating Broker Compensation is for MLS members only.

Listed by Alberti Team of Gibson Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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 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 August 20, 2022. 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.