Cape Cod Homes with a Guest House

MLS Number 73160498

• Residential
• Bedrooms 13
• Bathroom 6
• Square Feet 2,416

Nestled away along one of the enchanting footpaths of Provincetown's historic Commercial Street, The Captain's House Guest House is a remarkable opportunity awaiting its next chapter. This stately Federal Style home has been a cherished bed and breakfast for generations, embodying the very essence of Cape Cod hospitality. Steeped in history, this property is licensed for 13 rooms, accommodating up to 26 guests at a time. With its spacious layout and versatile floor plan, it offers an array of possibilities, including the potential for generous owner's quarters. The Captain's House is perfectly poised to continue its legacy as a thriving B&B, providing guests with an authentic Provincetown experience. For those seeking a more personal touch, the property's 13 bedrooms and 6 full baths make it a prime candidate for conversion into a magnificent single-family residence. The spacious rooms and elegant architecture await your creative vision to transform this property into your dream home.

Listed by Team Rick & Devin of Gibson Sotheby's International Realty

MLS Number 73155012

• Residential
• Bedrooms 7
• Bathroom 7
• Square Feet 6,549
• High School Barnstable

“I saved you a seat.” Welcome words when showing up late for a performance in a crowded venue. As Cape Cod becomes more crowded, it’s a near impossible challenge to secure your spot in the “front row” next to the view and away from the throngs. Worry not, the “seat” we have for you is on nearly seven acres of pristine land between Hamblin and Middle Ponds, part of the triumvirate that comprise the famed Indian Ponds. This estate features a 4,447 square foot main residence modernized to the highest level, two carriage houses, a resort style pool with outdoor kitchen, bar and beach-side guest house. The dining room can accommodate generations of diners at a single table in front of the fireplace. The seasonal dock extends from the sandy shoreline and is the base to launch small craft. Do you know how much fun you can have on a pontoon boat? Puttering, drifting, diving, grilling or just enjoying a morning brew. The show unfolds daily and hourly, including both sunrise and sunsets.

Listed by Jack Cotton of Sotheby's International Realty

MLS Number 73142704

• Residential
• Bedrooms 6
• Bathroom 6
• Square Feet 4,656

Situated on a tranquil cul-de-sac a short drive to multiple beaches, the country club, wildlife, and historic main street of Falmouth this 6 bed, 6 bath, 6100+ sq ft is an idyllic retreat! An exquisite colonial surrounded by an in-ground pool, tennis courts, grape-draped pergolas, wooden deck, and a stone patio. The fun continues with a walk-out basement including a kitchen, bar, wine cellar, and so on. The home boasts glowing hardwood floors, a brick fireplace and classic wood stove, with sunlight pouring through the french doors and windows emphasizing it's airy spaciousness. A chef's dream, the kitchen gleams with Italian marble countertops, a massive black cherry island, and high-end gourmet stainless steel appliances. Each bedroom is a vast sun-lit haven while each bathroom is an elegant and spa-like sanctuary. Guests are sure to enjoy their time in the guest house with full bath and a separate gym overlooking the pool. Make this blissful playground your personal resort, come view

Listed by Danny Griffin and Laura Crowe of Griffin Realty Group

MLS Number 73124636

• Residential
• Bedrooms 6
• Bathroom 8
• Square Feet 7,700

Absolute perfection at this stunning in-town compound featuring commanding water views over Oyster Pond! The result of a multi-year collaboration by top architects, designers and builders, this sophisticated and turn-key coastal offering seamlessly blends classic and contemporary elements to create a one-of-a-kind retreat. Walls of glass overlook expansive lawns and gardens, while sun-drenched living spaces set the stage for large scale entertaining, or relaxed everyday living, alike. Top of the line systems and amenities are found throughout the thoughtfully designed 5 bedroom main house, while a 3 story guest house provides additional accommodations overlooking the beautiful pool and spa. Immediate access to the beach, with a private association dock, and just steps to the restaurants, shops and galleries of Chatham’s quintessential Main Street, this exclusive offering is a must see, by appointment only.

Listed by Maggie Gold Seelig of MGS Group Real Estate LTD

MLS Number 73113144

• Residential
• Bedrooms 5
• Bathroom 7
• Square Feet 4,190

A sublime transformation of a landmark property on coveted Tonset Rd. in East Orleans. Classic Cape Cod charm combines with modern amenities in this resort-like compound. The main house and companion guest house offer 5 bedrooms, 7 bathrooms, and 4190sf of extraordinary living space filled with custom details. A saltwater, gunite pool unites the two across the private, 1.25 acre pastoral landscape. From the minute you enter the circular driveway, this lovely house captivates, with its crisp white shingles, copper gutters, and elegant plantings. The main house features a designer kitchen, marble-clad gas fireplace, a first-floor primary with walk-in closet, along with two additional second floor ensuites - one of which includes a wet room with built-in soaking tub. The home's walkout lower level includes a lounge with wet bar that leads to a firepit overlooking the pool. The stunning guest cottage has cathedral ceilings, a well-appointed kitchen & living room and another 2 beds/baths.

Listed by Sarah Keith of eXp Realty

MLS Number 73101719

• Residential
• Bedrooms 5
• Bathroom 4
• Square Feet 2,907

In this idyllic setting in the village of Cotuit, you will have the best of both worlds for the ultimate Cape Cod lifestyle. The historic Main House, built in 1870 is restored and charming with four bedrooms and the separate, modern Guest House as bright and open to all your possibilities with a spacious living room, kitchen and bedroom suite. These companion gems are nestled between Riley's Beach (Cross Street) and Loop Beach which reside on Cotuit Bay sitting barely .1 and .3 miles respectively to the water! This turnkey property is ready for your enjoyment with immaculate grounds giving you privacy and solitude as you shuttle between the Guest House and Main house. The residence originally known as the Captain Handy Homestead is a four bedroom Greek Revival home with exquisite details, wood floors and easy flow. The separate Guest House settles above the garage and possesses a private balcony for your tranquil relaxation, was built in 2004.

Listed by Peter Lomenzo of Gibson Sotheby's International Realty

MLS Number 73088912

• Residential
• Bedrooms 8
• Bathroom 5
• Square Feet 4,033

From its unparalleled location on Little Island in Osterville, this special waterfront estate overlooks the waters of West Bay and offers breathtaking water vistas from its private, elevated setting. This 2.45-acre lot features a substantial deep water dock, private sandy beach and an expansive yard. The 3,315 square foot main house is abundant in space with six bedrooms and a substantial multilevel deck. The first floor features grand living and family rooms with impressive fireplaces and water views on three sides, cook’s kitchen, dining area and a primary suite with two walk-in closets, luxurious bathroom and incredible water views. The second floor features five bedrooms, two full bathrooms and a water view balcony. The outdoor living spaces are equally impressive, with a sprawling backyard and patio areas with ample space for relaxation. A two-bedroom guest house with deck is available for overflow guests. Truly a once-in-a-lifetime opportunity to enjoy your own piece of paradise

Listed by Robert Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

MLS Number 73070365

• Residential
• Bedrooms 8
• Bathroom 6
• Square Feet 4,859

Magnificent eight bedroom mansion from days gone by, designed by famous architect Edward Sears Read. Perched on a hill overlooking Chatham Harbor, North Beach, and the Atlantic Ocean beyond. Almost 300 feet of sandy private beach described by an article in CNN as "one of the top 9 secret beaches in NORTH AMERICA". Three acres of land has room for expansion, a guest house, a pool, and/or a tennis court. A true forever, family compound within an easy walk to downtown Chatham or Chatham Bars Inn. Must see the whole property, inside and out, to fully appreciate the surroundings, the privacy of the three acres, the 300 feet of beach, the eight bedrooms, the six fireplaces, and the miles of views to the north, south, and east. And what a spectacular, one of a kind property owned by the same family since the 1940's.....Opinion of some people in town is that this is the nicest property in Chatham......You decide......

Listed by John Burke and Waldo Brown of William Raveis Chatham

MLS Number 73053158

• Residential
• Bedrooms 7
• Bathroom 8
• Square Feet 7,413

This extraordinary waterfront estate with magnificent water views over Centerville River and Nantucket Sound features 200 linear feet of water frontage, a private deep-water dock, and waterside boathouse. This unique offering, with its elevated coastal setting and ocean views, is enhanced with stunning landscaping and manicured lawns that wrap the .99-acre site. The 5-bedroom main residence, with 5,600 sq ft of living space, features a multi-level floor plan that is both bright and spacious and offers a living room, family room and well-equipped kitchen with dining area, breakfast nook and sitting area all providing access to the multi-tiered decks overlooking the water. Complementing the main home is a beautiful guest house with 1,794 sq ft, a large bonus room and private balcony overlooking the water. Complete with a 3-car garage and separate .38-acre parcel featuring a private, white sand beach on Nantucket Sound, this unique offering has captured the essence of seaside living.

Listed by Robert Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

MLS Number 72950704

• Residential
• Bedrooms 9
• Bathroom 9
• Square Feet 7,200

One of the finest oceanfront properties to exist in all of New England, "High Scatteree" sits proudly on nearly 3.7 acres and is sited to enjoy absolutely commanding water views. Behind tall and established hedges for the ultimate in privacy, a winding gravel drive welcomes guests to the classic shingle style Main House which offers 7 bedrooms, 7 fireplaces and a thoughtful floor plan ideal for comfortable family living or grand entertaining alike. Surrounded by meticulous lawns and gardens, a clay tennis court is found nestled on the park like grounds which include a personal arboretum of specimen trees. A 2 bedroom Guest House overlooks an award winning seaside rose garden, while steps to a private beach, deep water dock, and boathouse complement the property's many resort-like amenities. Updated and expanded several times by top builders and craftsmen, this once-in-a-lifetime property blends timeless architecture and current finishes with modern systems and infrastructure.

Listed by Brian Dougherty and Nicholas Robert of Compass

MLS Number 72933462

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

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