Cape Cod Homes with a Guest House

Homes for Sale with Guest House on Cape CodHere you'll find all Cape Cod homes for sale with a guest house.

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7 Cobblestone Plymouth MA 02360

Plymouth, MA7 Cobblestone, Pinehills

Price$1,000,000

Est. Mortgage: $/month

Open House

MLS Number 73344523

  • Residential
  • Next Open House: Sat 03/15 11:45 am. to 12:45 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,769

OPEN HOUSE SATURDAY 11:45am - 12:45pm. This custom home is truly unique in every way and every detail, and the homeowners have spent well over $150,000 on improvements over the past 7 years, since moving into the home. This place is simply perfect, and you will realize that the moment you walk through the front door. The "Fish Shack" floor plan is nestled in the quaint Sconset, Nantucket-inspired Cobblestone neighborhood. Beautifully dark stained wide plank pine floors throughout the home. The gourmet kitchen has "beehive" backsplash, upgraded stainless appliances and bead board ceiling. Large family room with French doors to private deck. 2nd level has primary suite and guest suite with plenty of privacy. Lower level boasts a great room and 3rd private bedroom. Great room with French doors leads out to covered patio. Situated in a cul-de-sac set back with a long driveway and beautiful plantings. Close proximity to all Pinehills amenities. Please see attached IMPROVEMENTS DOCUMENT!

Listed by Pinehills Resale team and Jesse Greenstein of Pinehills Brokerage Services LLC

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$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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16 Stonefield Drive Sandwich MA 02537
Open House

MLS Number 73344202

  • Residential
  • Next Open House: Sat 03/15 11:00 am. to 1:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,636

Coastal living with breathtaking water views. Own a slice of paradise in this three-bedroom home with tons of bonus space, offering 2.5 bathrooms and panoramic views of the tidal marsh, Spring Hill River, and Cape Cod Bay. Relax on the large inviting farmer’s porch and multilevel decks while taking in the coastal breezes, sounds of the waterfall from the koi pond and distant crashing waves on Spring Hill Beach. Inside, an open and airy layout welcomes you with sun-drenched living spaces, perfect for entertaining or quiet retreats. The well-appointed kitchen flows seamlessly into the dining and living areas, all designed to maximize the stunning waterfront environment. Upstairs, spacious bedrooms provide peaceful sanctuaries, while a bonus space offers endless possibilities—home office, playroom, or guest quarters. Don’t miss this rare opportunity to own your farmhouse by the sea.

Listed by Derouen Levinson Group and Paul Caucci of Keller Williams Realty

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$
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$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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16 Stonefield Drive Sandwich MA 02537

Sandwich, MA16 Stonefield Drive

Price$1,175,000

Est. Mortgage: $/month

Open House

MLS Number 22500934

  • Residential
  • Next Open House: Sat 03/15 11:00 am. to 1:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,036

Coastal living with breathtaking water views. Own a slice of paradise in this three-bedroom home with tons of bonus space offering 2.5 bathrooms and panoramic views of the tidal marsh, Spring Hill River, and Cape Cod Bay. Relax on the large and inviting farmer's porch, or multilevel decks while taking in the coastal breezes, sounds of the waterfall from the Koi pond and distant crashing waves on Spring Hill Beach. Inside, an open and airy layout welcomes you with sun-drenched living spaces, perfect for entertaining or quiet retreats. The well-appointed kitchen flows seamlessly into the dining and living areas, all designed to maximize the stunning waterfront scenery. Upstairs, spacious bedrooms provide peaceful sanctuaries, while the bonus space on the top floor offers endless possibilities: home office, playroom, or guest quarters. Don't miss this rare opportunity to own this farmhouse by the sea.

Listed by Derouen Levinson Group and Paul Caucci of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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15 Bay Road Chatham MA 02663

Chatham, MA15 Bay Road

Price$4,950,000

Est. Mortgage: $/month

MLS Number 73343719

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,110

Perched above Chatham Seaside Links, this architectural masterpiece blends classic coastal elegance with modern luxury. Just steps from pristine beaches and the Village’s renowned restaurants, it offers a private oasis framed by exquisite stonework, open-air living spaces, and lush native plantings.Inside, meticulous millwork, custom Kochman Reidt+Haigh cabinetry, and fine architectural details showcase exceptional craftsmanship. The living room with fireplace flows into an intimate sitting area, partitioned by a custom-built cabinet containing a motorize TV lift. Smart home technology enhances comfort throughout.The chef’s kitchen, with a copper sink island, connects to the formal dining room via a butler’s pantry. Thoughtfully designed indoor-outdoor spaces maximize year-round enjoyment. With four bedrooms, including a first-floor guest suite and serene primary suite, privacy is paramount. A billiard room, wine cellar, and entertainment space complete the refined lower level.

Listed by Chris Rhinesmith of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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15 Bay Lane Chatham MA 02633

Chatham, MA15 Bay Lane

Price$4,950,000

Est. Mortgage: $/month

MLS Number 22500915

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,371
  • Parking Spaces 3

Nestled in an elevated position overlooking Chatham Seaside Links, this architectural masterpiece embodies classic coastal elegance. Just a stone's throw to Chatham's pristine beaches and the Village's renowned restaurants, the residence offers a private oasis. It is framed by masterful stonework, open-air living spaces, and artisanal native plantings--setting a captivating tone before you even step inside. The foyer sets the stage for the exceptional design that unfolds within. Built by Steven Nickerson, meticulous millwork, custom Kochman Reidt+Haigh cabinetry accentuating many spaces, and intricate architectural details are found throughout the home. The house boasts an extraordinary level of artistry and craftmanship. The main living room with fireplace is refined yet comfortable and flows seamlessly into an intimate sitting area, partitioned by a custom-built cabinet containing a motorized TV lift, creating multi-use spaces. Smart home technology enhances both functionality and ambiance throughout. (Cont.) The stunning chef's kitchen, anchored by a central island with a striking copper sink, connects to a formal dining room through a butler's pantry, creating a seamless space for entertaining. The home's thoughtful design embraces seamless indoor-outdoor living, with multiple open-air patio spaces designed for enjoyment throughout the day. With four beautifully appointed bedrooms, three on the upper level connected by a reading room, privacy is paramount. The first-floor guest suite offers a serene retreat, while the primary suite above boasts a breathtaking, light-filled bath with luxurious finishes. Two additional bedrooms share a well-appointed bath. One bedroom features custom-built trundle beds, an ideal children's hideaway. The one-of-a-kind lower level is an extension of the home's refined aesthetic and offers entertainment and productivity. This level is anchored by an entertainment room that seamlessly connects to an elegant home office, a billiards room, a multi-use wine and bar room, and a half bath. Custom built-ins, seamless wood floors, a serene color palette, and ambient lighting define this floor and the entire home. A rare opportunity to own a coastal sanctuary, where thoughtful design, craftsmanship, and an unparalleled location converge in perfect harmony.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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8 Chilton Street Plymouth MA 02360

Plymouth, MA8 Chilton Street, Downtown

Price$1,995,000

Est. Mortgage: $/month

MLS Number 73343115

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 4,126

Chilton St.~ Stately Intown Colonial located in prime location just steps from the Historical Plymouth Waterfront. This rare find home with over 4100 sq ft of versatile living space has been completely renovated inside and out and is the perfect combination of maintaining old world character and charm with every modern feature. The curb appeal is unparalleled with walls of roses, gated driveway , granite walls / black iron fencing, Features include ~ Original beamed ceilings, State of the art Chef's kitchen with grand center island completely opens to outdoor living room through a 12' accordion door with cobblestone entertainment center with fireplace and pergola to bring the outdoors in. Harbor views from the Owners suite with indoor / outdoor shower. In home office, covered porches, High ceilings, Wet bar with custom built ins, 4 fireplace ( 3 wood /1 gas ) private guest suite potential , 4 car garage with A/C and heat. 10 exclusive parking spaces on property. Legacy property

Listed by Lynne Morey of Coldwell Banker Realty - Plymouth

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$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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38 Whiton Avenue Hingham MA 02043

MLS Number 73337458

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,584
  • High School Hingham High

Wonderful Crow Point home beautifully updated. This unique property has a rare double lot with potential for an inground pool. Updated gourmet kitchen with large center island, stainless appliances, eating area with custom banquet & turret ceiling. Sunny family room with skylights, custom built-ins, fireplace & French doors that lead out to a private backyard with covered patio area, fireplace, firepit & outdoor kitchen. Gracious dining room with butler's pantry.. Living room with fireplace, period details & loads of charm. Convenient 1st floor office with a view of the water. Updated primary suite with walk in closet & full bath.. 3 additional guest bedrooms on the 2nd floor with double sink full bath. Spacious finished 3rd floor exercise room (could be used as additional sleeping area). 3 car garage with finished 2nd floor heated & a/c game room/ guest suite with full bath. Steps to North Beach.. Close to train, commuter boat, restaurants, shopping, Hingham square & Yacht club.

Listed by Joanne Conway of William Raveis R.E. & Home Services

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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113 Seapine Chatham MA 02635

Chatham, MA113 Seapine

Price$9,950,000

Est. Mortgage: $/month

MLS Number 73341713

  • Residential
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 3,504

Designed by the award-winning architectural firm Polhemus Savery DaSilva, this waterfront masterpiece has been refined with elevated finishes by renowned designer Lisa Tharp. Set on Crows Pond, the open-concept main level showcases breathtaking water views from the stunning chef's kitchen and great room with open dining area, all seamlessly flowing to a screened porch, expansive stone patio, infinity pool, and deck—a front-row seat to 4th of July fireworks, Coffered ceilings, custom built-ins, monochrome palettes, and striking light fixtures add to the home's sophisticated aesthetic. A private first-floor guest suite offers a serene retreat with its own patio and spa-like bath, while the upper level features a primary suite, a water-view bedroom, a charming children's room, and a central loft. The lower level is designed for entertaining, complete with a bunk room, full bath, game room, media area, and direct access to the outdoor shower. Showings start Sunday, March 9th.

Listed by Chris Rhinesmith and Pam Wise of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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113 Seapine Road Chatham MA 02650

Chatham, MA113 Seapine Road

Price$9,950,000

Est. Mortgage: $/month

MLS Number 22500816

  • Residential
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 5,850

Designed by the award-winning architectural firm Polhemus Savery DaSilva, this waterfront masterpiece has been refined with elevated finishes by renowned designer Lisa Tharp. Set on Crows Pond, the open-concept main level showcases breathtaking water views from the stunning chef's kitchen and great room with open dining area, all seamlessly flowing to a screened porch, expansive stone patio, infinity pool, and deck--a front-row seat to 4th of July fireworks, Coffered ceilings, custom built-ins, monochrome palettes, and striking light fixtures add to the home's sophisticated aesthetic. A private first-floor guest suite offers a serene retreat with its own patio and spa-like bath, while the upper level features a primary suite, a water-view bedroom, a charming children's room, and a central loft. The lower level is designed for entertaining, complete with a bunk room, full bath, game room, media area, and direct access to the outdoor shower. This turnkey resort-style retreat offers the best of coastal luxury, with thoughtfully designed indoor and outdoor spaces, ample room for guests, and unparalleled amenities for effortless entertaining.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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 Harvard Street Boston MA 02129

MLS Number 73340274

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,080

Extraordinary opportunity to own an iconic, corner residence overlooking picturesque Harvard Mall. Expansive 4,080 home offers grand proportions & exceptional light throughout w/3.5 upper level BR's, 4.5 baths, 3 living rooms/dens, a spacious patio and 2 parking spaces. Parlor level provides an open floor plan w/large eat-in kitchen, center island & dining room. Exceptionally wide double parlor on the second level is designed for grand entertaining w/ dramatic 11 ft. ceilings, multiple exposures & exquisite period details. Beautifully preserved crown moldings, marble fireplaces & custom woodwork retain a timeless elegance. Third level offers 2 generously sized bedrooms as well as a front-facing office/nursery space. A large floor-thru primary suite w/walk-in closet, ensuite bath, den and fireplace occupies the top level. The finished lower level featuring a mudroom, office/guest suite, full bath & storage area w/direct access to the patio & driveway complete this rare offering.

Listed by Elizabeth Damon and Charlotte Polk of Donnelly + Co.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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5 & 9 Strandway West Harwich MA 02671

MLS Number 73339426

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 2,517

From its wraparound spectacular views to its private sandy oceanfront beach, from its exceptional 30-foot deep-water dock (THREE boat slips!) on Herring River to its peninsula-tip location, The Windmill is a gem set in an exclusive enclave. The Windmill House itself, a classic icon depicted in countless paintings and postcards, is replete with wide pine floors, hand-hewn beams, fireplaces, and windows framing breathtaking water views. Guarding against erosion, frontage on Nantucket sound is foliated by indigenous plants; a natural barrier. On the riverside, two long jetties protect the beach from prevailing southwest winds. And a series of small jetties originally designed to build up the beach exert a constructive force against erosion. All this, plus a buildable oceanfront lot and a guest house with kitchenette and bath overlooking Herring River add up to an unrivaled opportunity that truly captures the timeless spirit of Cape Cod.

Listed by The Powissett Group and Stephanie Sugden of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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79 Neshobe Road Mashpee MA 02649

Mashpee, MA79 Neshobe Road

Price$2,499,999

Est. Mortgage: $/month

MLS Number 73340129

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3,238

Welcome to a breathtaking waterfront community, featuring a deep water dock, kayak storage racks, a children's play area, and a beautiful beach area. This stunning compound is nestled on a private cul-de-sac and consists of a custom-built farmhouse and a guest house, seamlessly blending luxury and comfort. The main house boasts 3 bedrooms, 3.5 bathrooms, and wide plank hardwood floors. The gourmet kitchen is equipped with top-of-the-line appliances and offers a delightful surprise with a hidden access to a walk-in butler pantry.The primary suite includes walk-in closets, a soaking tub, & a walk-in shower w/ custom tile. Enjoy indoor-outdoor living w/ a dual-sided fireplace & a wrap-around porch. The home has three-zone heating & air conditioning. A separate bungalow provides space for guests, w/ 1 bedroom, bath, & kitchen. Surrounded by stone wall & river rock patios, the property offers tranquility. In addition, the home includes a 2nd-floor laundry room & 4 garages.

Listed by Cynthia Crawford of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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This site was last updated March 14, 2025 11:51 PM EDT. 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.