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.

10 Ackermuck Nantucket MA 02554

Nantucket, MA10 Ackermuck Way

Price$7,495,000

Est. Mortgage: $/month

MLS Number 22104177

  • Single Family
  • Garage Spaces 1
  • MLS Status Active
  • Village Nantucket
  • Year Built 2022

Hidden at the end of a private way, this half-acre haven provides unmatched privacy with edge-of-town convenience. This development project offers the opportunity for a buyer to realize their Nantucket dream estate, while having the unique opportunity to chose their owner finish details. The property will include a five-bedroom, six-bathroom (five full, one half) above-grade main house & a two-bedroom, two-bathroom (two full) guest house/garage. An open-air gym with large barn doors adds to the property's unique character. The landscape design allows for effortless indoor-outdoor living, thanks to an oversized lawn and bluestone patio with 18' x 36' pool w/ 9x9 baja shelf, pool pavilion, outdoor fireplace, and multiple outdoor seating and dining areas. Main: 4,640 sq. ft. + 2,300 sq. ft. of unfinished basement | Cottage: 1,310 sq. ft. Garage w/Gym + Studio / 7 bedrooms / 8 Bathrooms. Includes oversized pool, pool pavilion, large lawn, and outdoor entertainment areas. First Floor The rising approach to the front entry will offer look through views to the back yard, the foyer space opens to multiple living areas both inside and out of the home. To the right the open living/kitchen/dining areas enjoy vaulted ceilings views, through glass doors opening to the blue stone patio and pool area. A mudroom entrance, laundry, pantry and half bath are all found or the kitchen area. Returning to the foyer you look upon a formal living room, complete with gas fireplace and another set of full panel glass doors that open to deck over looking yard area. Hall to stairs for both access to the second floor and lower level, and two first floor bedroom suites. Second Floor Landing arrives to a wide hall with abundance of natural light, two guest suites anchor one wing of the second floor. From the landing arrive to the primary suite foyer, chose your direction with choices for large walk in closet, five fixture primary bath, or bedroom area with vaulted ceiling, and French doors to 2nd floor deck overlooking the yard, pool and gardens. Basement Main House basement is full unfinished 2,300 sq.ft. Will be delivered with plumbing in slab for three additional bathrooms, and two sets of window wells to provide lower level rooms with natural light. Other Structures The landscape design allows for effortless indoor-outdoor living, thanks to an oversized lawn and bluestone patio with 18' x 36' pool w/ 9x9 baja shelf, pool pavilion, outdoor fireplace, and multiple outdoor seating and dining areas. Cottage: is complete with a an open-air gym with large barn doors, 1st floor bedroom, 1 car garage, on the second floor there is a large living area supported with a wet bar, and a second bedroom with full bath.

Listed by Brian Sullivan of Fisher Real Estate

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 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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116 Old Wharf Chatham MA 02650

Chatham, MA116 Old Wharf Road

Price$10,500,000

Est. Mortgage: $/month

MLS Number 22103713

  • Single Family
  • Garage Spaces 3
  • MLS Status Active
  • Village North Chatham
  • Year Built 1780

North Chatham Estate with Private sandy beach. The Red Tavern (c. 1780), a landmark North Chatham waterfront estate, is now available for purchase for just the 12th time in 240+ years.Since the end of the Revolutionary War, this property has been an enduring sentinel since it was first built overlooking North Chatham's Old Harbor, the town's first and most important port.Meticulously restored and maintained, the five bedroom, three and a half bath Federal style home has successfully melded its many historic elements with the expected amenities of today.The detached horse barn has been restored and converted into a warm and most charming three bedroom, two bath Guest house, ideal for family and friends.With seaside landscaping providing exceptional privacy, the elevated panoramic views of Chatham Harbor, North Beach and the Atlantic Ocean are breathtaking. A raised wooden boardwalk leads to your private sandy beach.Offered basically furnished, this important and historic property awaits the stewardship of the next discerning owner.

Listed by David H Doherty of Kinlin Grover Real Estate

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 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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353 Bridge Chatham MA 02633

Chatham, MA353 Bridge Street

Price$2,200,000

Est. Mortgage: $/month

MLS Number 22103609

  • Single Family
  • Garage Spaces 2
  • MLS Status Active
  • Village Chatham
  • Year Built 1860

Legendary location! Three houses down from Lighthouse Beach and the famous Chatham Light sits this family compound that boasts a renovated home with a beautiful guest house. The gracious and welcoming front house has an open concept main floor, updated kitchen and baths and a first floor primary bedroom.The rear guest house is a large living room bedroom combo with a full bath. Both homes look out on a pastoral view of conservation land. Walk to town or Lighthouse Beach. Plenty of room for guests with ample parking for multiple cars. There is a total of 4 bedrooms, 4.5 baths and a bonus office.This house has been renovated, lovingly cared for and has newer mechanicals and AC. New roof and a new oversized shed. All you have to do is move in. Being sold furnished with a few exclusions. Beautiful yard with possible room for a pool.

Listed by Kathleen Phelan of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 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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10,20,21 Scallop Barnstable MA 02655

Barnstable, MA10,20,21 Scallop Path

Price$19,800,000

Est. Mortgage: $/month

MLS Number 22103487

  • Single Family
  • Garage Spaces 4
  • MLS Status Active
  • Village Osterville
  • Year Built 1770

Located on the private island of Oyster Harbors, and overlooking Nantucket Sound and Martha's Vineyard, one of Cape Cod's original homes presides over its location as vestige of a bygone era. Complete privacy is assured with almost 7. 5 acres on an elevated bluff. The water view encompasses 270 degrees. The site includes multiple buildings on three separate buildable lots. ''Scallop Path'', as the property is known, is now available for sale for the first time in almost 50 years. The main house, with 7 bedrooms and 5 full baths, is believed to have been moved across Cotuit Bay from the mainland to Oyster Harbors in the 18th century. The core of the home may date to as early as 1680 and some features certainly reflect that history. The sizable central chimney houses a passageway where the occupants could safely hide, perhaps during King Phillip's War. In all the buildings have 8 fireplaces.Restored by a well-known family in the 1970's the home and guest house were modernized to include central air conditioning and other modern features. Perhaps the property's most renowned feature are the gardens. Flower gardens, herb and vegetable gardens were all designed by one of country's most famous horticulturalists. This same individual actually redesigned the White House gardens in the 1960's. A guest house from the 1970's contains two separate bedrooms, bathrooms, kitchen and laundry. Other buildings on the site include classic architectural features. A woodshed is a point of focus while functioning as a working shed. The boathouse and garage are connected to each other by a breezeway overlooking a secluded cove. While the property currently contains 5,894 square feet of living space, architect Patrick Ahearn has filmed a video to discuss what the future may hold for the site. New owners will be able to create a sanctuary of their own in what many view as a picturesque paradise from another time.

Listed by Zenas Crocker of Berkshire Hathaway HomeServices Robert Paul Properties

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 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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371 Route 6A Sandwich MA 02537

Sandwich, MA371 Route 6A

Price$720,000

Est. Mortgage: $/month

MLS Number 22102817

  • Single Family
  • MLS Status Active
  • Village East Sandwich
  • Year Built 1780
  • Bathroom 3

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 Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 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

Pending

MLS Number 22102020

  • Single Family
  • Garage Spaces 2
  • MLS Status Pending
  • Village Chatham
  • Year Built 1949

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. 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.

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 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: 2.8% last updated on Jul 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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Stage Neck Chatham MA 02633

Chatham, MAStage Neck Road

Price$14,800,000

Est. Mortgage: $/month

Pending

MLS Number 22101792

  • Single Family
  • Garage Spaces 3
  • MLS Status Pending
  • 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: 2.8% last updated on Jul 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

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 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$849,000

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: 2.8% last updated on Jul 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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9 Meadow Spring Sandwich MA 02563

Sandwich, MA9 Meadow Spring Drive

Price$665,000

Est. Mortgage: $/month

Pending

MLS Number 22101133

  • Single Family
  • Garage Spaces 3
  • MLS Status Pending
  • Village Sandwich
  • Year Built 1776

Estate Setting waiting for you! Carriage House offers beautiful living spaces on both floors, with Bonus Rooms, modern Kitchens, and open floor plans. Rental income now $38,000/year (under market), or convert the Carriage House to your Family Home. Additional Post and Beam Barn overlooks the Marsh at Scorton Creek, and would make an outstanding Guest House, built but never used as a 4-stall horse stable. Surrounded by pasture land, 4-6 contiguous acres available for your Dream House, upland with commanding southern-exposure views of the Marsh at Scorton Creek.

Listed by Chuck Tuttle of William Raveis RE & Home Serv.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 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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306 Old Comers Chatham MA 02633

Chatham, MA306 Old Comers Road

Price$1,295,000

Est. Mortgage: $/month

Pending

MLS Number 22100799

  • Single Family
  • Garage Spaces 1
  • MLS Status Pending
  • 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 home is in excellent condition and only requires white paint on the wood work and cabinetry if a buyer prefers that look. A bit of decorating could make this home a show stopper. Very well built, the home offers a sunny southern exposure and large windows with an ever changing view. Included in the design is an over sized family room which is open to the large kitchen and living room perfect for entertaining a crowd. All the bedrooms are all oversized including a primary ensuite bedroom on the first floor. A large wrap around deck encourages outdoor living. There is a home office and gym space in the bonus space in the lower walk out level. 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: 2.8% last updated on Jul 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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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 July 30, 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.