Everyone loves company, but boundaries are essential even with the most beloved of visitors. The finesse to entertaining overnight guests lies in balancing generous hospitality with comfortable enough distance to keep living life with minimal disruption. These unique guest houses at our listings north of New York City provide both sumptuous accommodations and plentiful privacy for host and guest, an essential factor whether for short stays and extended sojourns.
GREENWICH | 2 Conyers Farm Drive | $6,995,000
Who ever said putting guests up in the barn had to be a bad thing? At this Conyers Farm enclave, friends and family will feel as though they've won an all-inclusive at a rustic Adirondack resort. The timber-framed structure blends beautifully into the lush 10 acre retreat, which includes an outdoor kitchen and gracious stone terraces to support entertaining. An open floor plan in the main home adds additional non-intrusive common areas, with an open showcase kitchen, loft and living space with soaring ceilings.
See more of 2 Conyers Farm Drive
CHAPPAQUA | 1110 Hardscrabble Road | $2,275,000
Behold, everything we could have hoped and dreamed upon spotting "carriage house" in the listing copy. On 7.5 acres of prime suburban real estate, this Chappaqua country compound is a portal into the past, with this mortared stone structure built as the gilded-age garage to service residents of the estate's 1875 antique farmhouse. There's a log cabin elsewhere on the property, and when vacant from visitors, the eclectic interiors can easily double as an artist's studio.
See more of 1110 Hardscrabble Road
PAWLING | 747 North Quaker Hill Road | $3,400,000
Like a life-sized Lincoln Logs set, this absolutely #adorbs timber cabin is a classified one-bedroom accessory cottage on a magnificently restored Colonial estate. Beaver Pond Farm boasts over 110 acres of open meadow, natural woodlands, a stocked pond and even its own extensive trail system. Steps from the 1770 main house, there's an additional three bedroom guest house, offering a compelling refutation to the Ben Franklin aphorism that "guests, like fish, begin to smell after three days."
See more of 747 North Quaker Hill Road
BEDFORD | 270 Hook Road | $1,160,000
We'll call this one the boutique model. In Bedford, this Gatsby-era gentleman's farm boasts three small cottages, affording the rather miraculous privilege of entertaining multiple disparate groups of visitors simultaneously—so be warned, you might have a hard time getting out of hosting the family reunion. A pool and tennis court also share the almost 40 acre grounds with its main attraction: a gambrel-roofed stone and shingle main house.
MILTON | 7 Sands Dock Road | $1,160,000
Is "poetically-sited" an acceptable real estate copywriting term? Last but certainly not least, this pondside Hudson Valley guest cottage is about as cute as they come, with two floors, a back deck and helplessly inviting rocking chair porch for bike storage. The surrounding 4.5 acres overlook the Hudson River's West Shore, beckoning views best enjoyed from the 6,200+ square foot main house and adjacent poolside patio—a shingled carriage house offers additional detached quarters. We won't be held responsible if your visitors never want to leave.