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.

835 Sea View Barnstable MA 02655

Barnstable, MA835 Sea View Avenue

Price$30,000,000

Est. Mortgage: $/month

MLS Number 22200155

  • Single Family
  • Garage Spaces 7
  • Full Bath 9
  • Half Baths 5
  • MLS Status Active

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

58 Oyster Pond Falmouth MA 02540

Falmouth, MA58 Oyster Pond Road

Price$825,000

Est. Mortgage: $/month

Pending

MLS Number 22200017

  • Single Family
  • Full Bath 1
  • Half Baths 1
  • MLS Status Pending
  • Village Falmouth

This unique property features a main house, a guest house and a tree house for fun. It is in a great location in Quissett, near the bike path, beach, Spohr Gardens and the Knob. Take a quick bike ride on the Shining Sea Bike Path to Woods Hole for lunch or to Falmouth village to shop. Stroll to the beach and relax for the day. The house location entitles membership to the private Quissett Beach. The main house appears to be a Cape, but the interior has a more contemporary feel with an open floor plan, beamed ceilings and sky lights. The first floor consists of a kitchen and dining area open to the main living area, 2 bedrooms and a full bath. Another bedroom is on the second floor with a loft sitting area or office area. There is a full walk-out basement that could also be finished for additional living space,]. Enjoy outdoor living on the oversized deck. A walkway from the deck leads to the guest house that consists of a living area, 2 rooms, a loft, and half bath. There is also an outdoor shower, which is a must on the Cape The wooded lot lends privacy to the property. The square footage does not include the guest house or walk-out basement. A must see!

Listed by Sue G Gregory of Kinlin Grover Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

87 Beach Orleans MA 02653

Orleans, MA87 Beach Road

Price$12,000,000

Est. Mortgage: $/month

MLS Number 22107060

  • Single Family
  • Garage Spaces 4
  • Full Bath 9
  • Half Baths 1
  • MLS Status Active

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

128 Starboard Barnstable MA 02655

Barnstable, MA128 Starboard Lane

Price$3,850,000

Est. Mortgage: $/month

MLS Number 22107063

  • Single Family
  • Garage Spaces 2
  • Full Bath 5
  • Half Baths 1
  • MLS Status Active

This is a rare opportunity to purchase an Osterville waterfront compound that ambles along the river and is gently nestled into one of the most beautiful natural settings on Cape Cod. Watch swans nest, ducks swim and herons fly while enjoying indoor /outdoor living on over 2.5 acres. This Osterville home enjoys gracious rooms with beautiful views all on one level. The one bedroom guest house (480 sq. ft.) called 'The Crow's Nest', is its own charming get-away with a private bath, a mini kitchen and beautiful water views. The post & beam barn, known as, 'The Perch' was built as a separate office/gym on the grounds. It includes a great room with a wood burning stove and on the lower level a full bath, exercise room and service bar.128 Starboard Lane is a gardener's dream when it comes to life in the spring. The Meadow in bloom is breathtaking and the Rhododendrons lining the driveway are ablaze with color.The apple orchard is amazing along with the courtyard and outdoor spaces all with their own special gardens.Don't miss this special, one-of-a-kind opportunity to buy the perfect legacy property in Osterville!

Listed by Gene Orloff of Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

7 Academy Sandwich MA 02563

Sandwich, MA7 Academy Road

Price$1,795,000

Est. Mortgage: $/month

MLS Number 22106743

  • Single Family
  • Garage Spaces 2
  • Full Bath 2
  • Half Baths 1
  • Village Sandwich

Referred to as 'Grove Hill' this nearly 4 acre estate lot offers privacy while being located in Historic Sandwich Village. The 2,798 square foot 3 bedroom 2-1/2 bath home has an attached 3 bay garage with 1,000 square foot unfinished bonus room above with 18-1/2 foot cathedral ceiling. There is currently a building permit for a one bedroom accessory guest house and a second primary dwelling on the property. The grounds are nicely landscaped with a variety of plantings in addition to the native black locust, honey locust, and Norway Maples. Greeting you on the way to the main house is the original ticket booth from the Dexter Grist Mill built in 1959. Other outdoor features include a brick farmers porch in front, a large brick patio in the rear yard, a 9' diameter hand carved granite fire pit and an illuminated remote seating area. A brick wood burning fireplace is centrally located in the open concept first floor. First floor laundry, mud room, pantry, and Primary bedroom suite. 2x6 construction, 3/4" Advantech subfloors with reclaimed 1x8 nail grade heart pine flooring throughout. Mahogany four panel doors with Oil rubbed bronze hardware on first floor and solid 4 panel doors with ORB hardware on second floor. Andersen A Series windows and doors Long leaf pine beams Cataumet Sawmill custom 9'x 4' x2"wood island countertop Led lighting All exterior trim is Azek which will not rot crack, split, or allow paint to blister or crack. Copper flashing on exterior Granite steps Genuine Sandwich Lantern Onion lights Leaf Guard gutters and downspouts Porcelain tile in mud room laundry and bathrooms. Honed Jet Mist granite tops in kitchen and laundry and marble tops in Primary bath and pantry. Kohler 6' x 42" Airbath soaking tub with chroma-therapy in primary bath. One piece Kohler vanity tops in half and second floor bathrooms. 30 yr. Certainteed Landmark roof shingles Maibec Select Predipped 2 Coat Seacoast 204 white cedar shingle siding. Custom size Lucigold forever Aluminum powder coated forever bulkhead with hydraulic assist. 22.5kw natural gas whole house generator

Listed by Jerry V Chambers and Paula Chambers of Sand Dollar Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

34 & 52 Caillouet Barnstable MA 02655

Barnstable, MA34 & 52 Caillouet Lane

Price$14,500,000

Est. Mortgage: $/month

MLS Number 22106688

  • Single Family
  • Garage Spaces 4
  • Full Bath 7
  • Half Baths 2
  • MLS Status Active

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

251 Green Dunes Barnstable MA 02647

Barnstable, MA251 Green Dunes Drive

Price$18,300,000

Est. Mortgage: $/month

MLS Number 22106436

  • Single Family
  • Garage Spaces 6
  • Full Bath 9
  • Half Baths 2
  • MLS Status Active

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

115 Cove Wellfleet MA 02667

Wellfleet, MA115 Cove Road

Price$827,220

Est. Mortgage: $/month

Pending

MLS Number 22106197

  • Single Family
  • Garage Spaces 1
  • Half Baths 2
  • MLS Status Pending
  • Village Wellfleet

This late 18th c. home stands as a unique and rare time capsule. A purist's delight and one of the few historic half dwelling houses in Wellfleet, the Chipman House sports fine molding, wide board wainscoting, boxed corner posts, original doors, hardware, wide pine floors and its' early 19th c. set kettle for boiling water. This generational home has been used as a summer retreat and is heated by a cozy gas stove in the kitchen and wood burning stove in the front parlor. The 1940's detached guesthouse has been recently remodeled and is packed with charm. In addition to the guest house, the property includes a garage, barn, shower building with inside and outside shower, and a 2-seater outhouse. All of this on 6 acres of gently sloping land with gardens and woods. A mere 3-tenths of a mile to Chipman's Cove, named after the original owner of this house.Own an important part of Wellfleet's history in this delightful property.

Listed by Lisa R Hassler of Kinlin Grover Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

47 & 53 Little Beach Chatham MA 02633

Chatham, MA47 & 53 Little Beach Road

Price$4,790,000

Est. Mortgage: $/month

MLS Number 22106088

  • Single Family
  • Full Bath 3
  • MLS Status Active
  • Village Chatham
  • Year Built 1941

Prominently sited in the sought-after beach enclave of Morris Island, this iconic compound includes two 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. This rare offering provides an incredible setting to kick off your shoes and bask in the simple yet stunning beauty of Chatham. 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 Paul E Grover and Team Guthrie - Mabile of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

5 Black Fish lane Nantucket MA 02554

Nantucket, MA5 Black Fish lane

Price$6,495,000

Est. Mortgage: $/month

MLS Number 22104740

  • Single Family
  • Garage Spaces 1
  • Full Bath 7
  • Half Baths 1
  • Village Siasconset

Welcome to the most magnetic place on Nantucket Island. From dramatic cliffs to its sandy beaches, and picturesque lighthouses, Siasconset is a scenic sanctuary full of historic charm. A new luxurious construction opportunity is now being offered. This new home boasts an exceptional architectural design with high-end finishes, an open concept, and approximately 4,920 sq. ft of finished space. Details include six spacious bedrooms of which five are en-suites with vaulted ceilings. A separate guest house with pool cabana will allow for many memorable family and friend gatherings. An expansive living room and dining area leading to a designer kitchen with top-of-the-line appliances will take your breath away. The second floor Master Suite offers its own private deck overlooking the lush, manicured grounds and salt water pool with jacuzzi. A Pristine location, situated on 0.43 acres, this luxurious estate has beautiful views and is in a convenient and highly desirable location. All this and more within close proximity to the beach and the renowned Sconset Village.

Listed by Natalia Xavier of Coastal Point Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

371 Route 6A Sandwich MA 02537

Sandwich, MA371 Route 6A

Price$625,000

Est. Mortgage: $/month

Pending

MLS Number 22102817

  • Single Family
  • Full Bath 3
  • MLS Status Pending
  • Village East Sandwich
  • Year Built 1780

Price adjustment! Here is a wonderful opportunity to own a charming antique home on historic 6A in East Sandwich. This unique home features, a country kitchen with beamed ceiling and built-ins, a family room which leads to a screened porch overlooking the lovely grounds, dining room with fireplace, living room with fireplace, home office, den, wide pine floors throughout, four bedrooms, three full baths, two story barn currently used as a retail shop, chicken coop, workshop, in-ground pool, and a two bedroom detached guest house. New electric panel, newer boiler,newer oil tank in main house. Close proximity to beaches, marinas, bike trails, hiking trails, schools, and shops. Information herein deemed reliable but not guaranteed. Buyers/Agents to verify.

Listed by Michele Hopkins of Kinlin Grover Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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
  • Full Bath 4
  • Half Baths 1
  • MLS Status Active

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: 3.45% last updated on Jan 13, 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.

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 January 19, 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.