Just when you think a home can’t possibly get any better, that’s when you spot the guest house—a unique feature that adds an immense appeal to an already magnificent property. With spacious, amenity-filled environments, some of which even include full live-in capabilities, there’s little reason for any pampered visitor to ever want to leave.
It’s time to focus on what lies beyond the main house! Here are six incredible guest homes that deserve to be in the spotlight.
175 Brookside Road—Darien, CT
This stately residence, which is one of Darien’s earliest homes, constructed in the year 1820 when the town was first established, lies on an expanse of sweeping grounds that is rare for its central location in town. The home was originally built on over 14 acres of land, but 10 acres of its initial plot was eventually sold to a builder, comprising what is now Stonewall Lane, a cul de sac off Brookside Road. On its current 4.5-acre property, individuals will find numerous amenities including an in-ground swimming pool and spa, outdoor cabana with a shower and sauna as well as a large, three-bedroom, two-bath guest house complete with two separate entrances. The fully habitable space is located in a beautiful setting, amid fine landscaping and adjacent to a patio and the property’s many appealing summertime amenities. Looks like it’s time for a visit—this is definitely the place to stay!
2 Clifton Place—Irvington, NY
How would you like to frequent the guest home of a historic architectural masterpiece on the Hudson? Once home to American financier and philanthropist John Jacob Astor III, the nearly five-acre plot of land, with idyllic water views in all directions, contains everything you could ever dream of and more. Beside the property’s 3-level Italianate villa-style mansion lies an 1,800 square-foot carriage house, which boasts three bedrooms and a terraced patio in a private setting. With views of the Hudson River and an elegant, fully functional atmosphere, this guest house is truly one-of-a-kind.
88 Humiston Drive—Bethany, CT
Perhaps the most unique feature included on this remarkable park-like estate located on nearly six acres of land in Bethany, CT, is its large carriage house, which boasts a finished, second-story apartment. This fully functional, livable space, which lies just 350 feet from the property’s main house, includes all-underground electrical utilities. The house contains full heating and air conditioning, as well as a separate septic system. Its lower level is comprised of an attached three-car, heated garage and additional carriage house garage space complete with a large workshop for various potential uses.
163/164 Middle Beach Road—Madison, CT
This vintage yet fully modernized Victorian residence includes two parcels of beautiful land in the town of Madison, CT. The year-round main house is set upon one acre of land with direct waterfront views, and the second plot is located across the way, complete with a seasonal guest house on Fence Creek. The space offers inhabitants two bedrooms and two baths, in addition to an open staircase and overall great style. Set up an office or easel in the guest home’s loft, which overlooks stunning vistas of the creek and neighborhood’s breathtaking coastal environment.
514 Rannapo Road—Sheffield, MA
On nearly 15 acres of lush grounds and sweeping orchards in the beautiful Berkshires rests a lovingly restored 1785 Colonial farmhouse complemented by a fully renovated post and beam guest house. This impressive bonus space offers additional living opportunities with numerous amenities as well as a comfortable sleeping loft. Individuals staying here can also enjoy its neighboring stone loggia and brick patio, which are surrounded by the property’s serene wonderland of pure natural beauty.
67 Squire Road—Roxbury, CT
Quietly situated on a 10-acre plot of land overlooking Jack’s Brook and bordering a 50-acre land trust in the town of Roxbury, CT, a stylish country home resides. The property offers professionally designed gardens, an apple orchard and plentiful outdoor living areas including a deck that looks out onto the brook as well as a private stone patio. Also embracing this scenic setting is the separate one-bedroom guest house, which includes a fully equipped kitchen, living room and full bath. A deck with views of the property’s brook side completes this one-of-a-kind guest space.