High-End Hospitality: 5 Properties with Inviting Guesthouses

One of the benefits of owning an estate is being able to offer guests their own truly private space. Whether in California’s wine country, on the banks of a Long Island lake, or on a historic street in Santa Fe, these welcoming guesthouses encourage visitors to relax in comfort and seclusion.

Elegant Wine Country Escape

Sonoma, California | Carol SebastianiSotheby’s International Realty – Wine Country – East Napa Street Brokerage

Quiet, private, and consummately peaceful, this 2.88-acre estate is a quintessential wine country getaway featuring a three-bedroom main residence, an inviting pool, a guesthouse, a sports court, and—naturally—a vineyard. Constructed in 2018, the 840-square-foot guesthouse offers a light-filled great room encompassing a full kitchen, a breakfast nook, and a stylish living and dining area; one or two bedrooms; and a relaxing covered deck with a fireplace. Views stretch out across the verdant, impeccably landscaped grounds and century-old olive trees toward Arrowhead Mountain.

Welcoming Waterfront Retreat

Watermill, New York | Pat Petrillo & Dawn PetrilloSotheby’s International Realty – Southampton Brokerage

This five-bedroom Shingle-style home and its charming guesthouse are nestled amid tall colorful trees on three acres offering an oversized two-car garage, gardens, a swimming pool, and two private docks on Mill Pond. Separated from the main residence by a swath of lush lawn, the delightful guesthouse boasts a great room with living and dining space, a kitchen, one restful bedroom with a bath, and a full basement. The “pond” is an 85-acre lake perfect for sailing, kayaking, canoeing, and fishing.

Classic Greenwich Getaway

Greenwich, Connecticut | Leslie McElwreathSotheby’s International Realty – Greenwich Brokerage

In the heart of midcountry Greenwich, this estate combines warm classical style with modern amenities. The five-bedroom main residence features a chef’s kitchen, pine-paneled living and dining rooms, a family room, a library, an office, a game room, a gym, a three-season porch, and a terrace perfect for alfresco living and dining beside the idyllic grounds. Overlooking the lovely heated pool is a carriage house with one bedroom and bath, a cabana with a half bath and a wet bar, and a one-car garage.

Historic Adobe Estate in Santa Fe

Santa Fe, New Mexico | Caroline RussellSotheby’s International Realty – Santa Fe – 326 Grant Avenue Brokerage

On a lovely thoroughfare on Santa Fe’s historic Eastside, this elegant adobe residence has been lovingly restored with careful attention to authentic style and craftsmanship. The main home is filled with light and boasts grand entertaining spaces, a gourmet kitchen, an owner’s wing, and a guest suite. Across the gardens lies a two-bedroom guesthouse with a living room, a kitchen and two bedrooms with en suite baths. The property also offers a one-bedroom studio and a stone structure that serves as a wine grotto.

Charming Centerville Colonial

Centerville, Massachusetts | Colleen RileySotheby’s International Realty – Osterville Brokerage

Walking distance from the attractions of Centerville, this property includes a home filled with classic style and an enchanting guesthouse. The main residence features living and dining rooms; a remodeled kitchen with granite countertops, an island, a pantry, and a bar; a sunroom; five fireplaces; a finished lower level; a deck; and a swimming pool enveloped by colorful landscaping. The cheerful, light-filled guest cottage offers a living area with French doors opening to the pool, a charming kitchen, and a breezy bedroom loft.

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