Homes with a Guest House

MLS Number 22200343

• Single Family
• Garage Spaces 4
• Full Bath 6
• Half Baths 1
• MlsStatus Active

A spectacular, sprawling custom home in The Glen at Willowbend, 16 North Glen Drive personifies luxury living. Built in 2001 as a builder's personal residence, this stately home has tremendous curb appeal due to an impressive architectural facade and perfect placement on a corner lot with acres of conservation behind. Impressive woodworking, gourmet kitchen, custom built-ins and privacy galore are just a few highlights of this one-of-a-kind home. Fabulous living spaces, a large finished lower level and a guest house/in-law apartment provide plenty of space for entertaining family and friends. This property has a 4 car garage and a golf cart garage as well as room for a pool! Make your appointment today to tour this exceptional property!Willowbend is a warm and welcoming private club community offering championship golf, superlative tennis on har-tru hydro courts, state of the art fitness center, olympic size pool and social pools as well as 5 star dining venues and endless social events for all ages! Furnishings (excluding art and personal items) are available for sale separately.

Listed by Team Willowbend of Southworth Willowbend RE,LLC

MLS Number 72937483

• Single Family Detached
• Square Feet 3780
• Bathroom 3
• Rooms 12
• Bedrooms 5

Welcome to # 21 Brierbrook and welcome home! Open and airy with room to roam, you will sure to be impressed with this expansive property in desirable cul-de-sac neighborhood. Sun splashed rooms, generous bedroom space and a versatile layout . All set on manicured grounds with space to throw the ball around, BBQ on the new tree deck or simply enjoy relaxing and taking in the beauty that surrounds you. A covered walkway shelters your entry from the main house to the bonus attached guest house with direct entry .Perfect for private office , work out area and more...Conveniently located in the Scotts Woods enclave and easy access to recreation in the Blue Hills, multiple commuter rail stations .. come take a look #21 this home has it all value, condition and location... Hurry to this one!

Listed by Susan Lewis-Grant of Coldwell Banker Realty - Milton

MLS Number 170463566

• Single Family
• Square Feet 5,686
• Year Built 1957
• Bathroom 7
• Bedrooms 5

GREAT OPPORTUNITY!!! This home is set on 2.1 acres, offering 5 bedrooms and 6 1/2 bathrooms. Formal living room + dining room, spacious kitchen with dining space, and spacious master bedroom suite + 4 additional bedrooms. Bonus rooms for home office, and family room. An elegant, classic home ideal for the savvy buyer with a vision to improve and create their dream home. Home is completed with a large inground pool, and an overnight guest house (per zoning not to be used as a rental ) with 2 bedrooms, living room, 2 bathrooms and 2 car garage.

Listed by Ed Villeda of William Pitt Sotheby's Int'l

MLS Number 1518593

• Residential
• MlsStatus Active
• Location Neighborhood, Rural
• Address 2089 U.S. Route One
• Bedrooms 4

Perched on a hill overlooking Little Island Cove and Little Island in Frenchman Bay, this house is a custom cape with cathedral ceilings in the living room, dining area and kitchen, lovely breakfast room, screened porch, and office all with views of the cove and island. There are two, first-floor bedrooms, a full bath and laundry. Two bedrooms on the second floor and a full bath. To top it off, the property has an enchanting, year 'round guest house with one bedroom, living room, dining area, kitchenette and full bath and is an incredible rental. The grounds are lovely with simple gardens, sweeping lawn to a few steps down to the beach, and stately trees lining the circular driveway. A minute away from the town harbor with launching ramp and a tennis court. Twenty minutes to Acadia National Park on the Schoodic Peninsula and half an hour from bar Harbor. A charming property.

Listed by Better Homes & Gardens Real Estate/The Masiello Group

MLS Number 1518482

• Residential
• MlsStatus Active
• Location Rural
• Address 178 Rancourt Lane
• Site Features Level,Wooded

Are you ready to start living life on water's edge? Literally. This property offers you just that and so much more! Let's start outside - This property is at the end of a dead-end road, talk about quiet! You'll have plenty of space to store your water toys in the 2-car, detached garage with storage above. You'll want to bring your boat, too, because what a rarity it is to own your very OWN BOAT LAUNCH! And yes, you'll be able to tie it up at your dock! The screened gazebo offers you those bug-free evenings to enjoy the sounds and sights of the lake. Completing the tour of the outside is a 1 bedroom, 1/2 bath Guest House with water views. Let's head inside - Walking through the main side door, you'll enter through the kitchen, complete with all appliances, dishes, and cookware. The kitchen opens up to the dining room and living room areas, which of course have water views. Dining room offers a gas wall heater while the living room provides heat by the electric fireplace. This electric fireplace can be replaced with a wood stove (as it once was) or any other heat option you prefer. Just off the living room is a stunning, 4-season glassed sunroom, which gives you a full view of the lake from all three walls, including a walk-out. This was once used as a bedroom, so you've got options! Completing the first floor is a utility room and a full bath with laundry. In my opinion, the second floor is a real treat! Another full bath, office or sleeping space, and another stunning room facing the water! Again, this room offers views from all three sides; you'll love waking up to this sight! To wrap it all up, this incredible property comes furnished and a list of other inclusions is available. Ready to start making memories in 2022? Don't wait, come take a look today!

Listed by Bean Group

MLS Number 1301648

• Residential
• MlsStatus Active
• Bathroom 5.2
• Square Feet 6485
• Bedrooms 5

This is the escape to privacy, serenity, and beauty with this fantastic offering encompassing 17.6 ACRES on TUCKER POND. Upon entry to the property you will be enamored with this piece of paradise. The home was built in 1990 and enjoys 5 bedrooms and 5 full baths with 2 half baths. Natural light flows throughout with lovely vistas of the water. Enjoy your morning coffee on your deck off your first-floor master. The floor plan is wonderful for entertaining with French doors leading to a wonderful deck for family fun and barbeques. The land is enchanting and offers plenty of possibilities for a pool and perhaps a guest house. There are 7 homes on this pond and each relishes in sheer privacy. Tucker Pond is an 86-acre freshwater pond where you can kayak, paddleboard and fish (great trout!) putter around on a small boat (10HP MAX) with loads of islands and coves to explore. So much fun to be had on this piece of heaven!

Listed by Lori Joyal of Lila Delman Compass

MLS Number 22200155

• Single Family
• Garage Spaces 7
• Full Bath 9
• Half Baths 5
• MlsStatus 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

MLS Number 72933462

• Single Family Attached
• Village Osterville
• Rooms 18
• Square Feet 15500
• Bathroom 14

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

MLS Number 170460263

• Single Family
• Square Feet 5,057
• Year Built 2013
• Bedrooms 5
• Bathroom 6

Set in the desirable Byram Point private assoc. in an exclusive water community along the Greenwich Coastline. Boat lovers take note to your own private dock on Byram river! Take your boat to the private islands, swim or Kayak at the private Hawthorne beach just steps away, exclusive to only 18 homes. Take a peaceful walk or a bike ride on the ultra private beautiful Byram shore road. Feel like you're on a vacation all year round! Custom Built shore col w/exquisite architectural details, sophisticated modern-day technology for today's ''Smart home capabilities''. Serene peaceful Waterview's from most rooms. Complete open concept w/stunning Gourmet kitchen that has it all. Property has your very own Guest House! Easy access onto highway, only 35 minutes from NYC.

Listed by Danielle Malloy and Jessica L Alsina of NestSeekers International

MLS Number 72932216

• Single Family Detached
• Square Feet 1,500
• Bedrooms 2
• Bathroom 2
• Rooms 5

Renovated charming Captains house in the tiny town of Monroe MA. 2 Bedrooms/2 baths. The house has been completely renovated with all new baths, kitchen etc. Unfurnished. Great vacation or full time house. If you decide to build another house perfect guest house. The house is on 220 Acres. Property has been cleared and many possible uses, private county estate, horse farm, solar farm, battery farm, sub division, etc. Many spectacular sites for building. Close to skiing, one hour Tanglewood, two hours Boston, three hours New York. North Adams is 15 minutes with upscale shopping, Mass Moca, restaurants, etc. This is a beautiful piece of flat land. Impossible to find this size property in MA. Miles of old stone walls that are worth over $200,000. Hi Speed Internet really fast!!!! Special one of a kind place.

Listed by Dave White of OwnerEntry.com

MLS Number 1517536

• Residential
• MlsStatus Active
• Bathroom 8
• Bedrooms 6
• Rooms 19

Escape to serenity at BOLDWATER, a unique deep-water oceanfront estate nestled on 38.6 lush acres in Brooklin. Here you'll enjoy stunning scenery and distant views of Arcadia, exceptional resort-style living afforded by 1,400 feet of shoreline along Blue Hill Bay, a private beach, 2-boat mooring/docking permit, elevator, heated oceanfront pool, a pool house with a kitchenette and bathroom. This fabulous offering has many possibilities, featuring an expansive main home, a buildable lot, gatehouse, and a guest house that can be used for company, or for income-production. In addition,17 acres can also be part of the sale to create an ultimate retreat! Built-in 1980, updated with a new roof (2021), the property sits amidst gorgeous woods and greenery, with its own tranquil lake, beautiful gardens, lovely fountain, and an apple orchard! The 3-level main house, at 14,375 sq/ft, is exquisite with 6 bedrooms, 6 full baths, and 3 half baths. Elegant interiors are enriched by incredible finishes such as hardwood and tile floors, 9 fireplaces, hand-painted murals, generous windows, thoughtful built-ins, and extensive millwork. This oasis is a perfect backdrop for entertaining and privacy, marked by a grand entryway with turned staircase, and graciously proportioned rooms for every lifestyle purpose. Adding to the allure is a paneled library, an enormous solarium for plant lovers, a chef's kitchen with granite counters, a huge island, stainless steel appliances, and a breakfast room. Six bedrooms, 3 with en-suite baths, are highlighted by the primary retreat with a spa-inspired bath and breathtaking ocean views. The enjoyment continues to the ground-level basement presenting an entertainment room, fabulous dry sauna, Jacuzzi bath, and more sleeping quarters. Both guest houses provide inviting accommodations with a living area, full kitchen, 4 bedrooms,3 baths, and 3 fire places. A generator assures backup power in the event of an outage for seamless living and peace of mind

Listed by Coldwell Banker Realty