Whether the goal is swimming or stargazing, each of these vast, stylish estates—from Florida to California wine country with the mountain town of Taos in between—is ideal for creating a private community.

Rancho San Carlos

This irreplaceable 237.82-acre estate is perched atop a hill at a secluded address in Montecito. At its heart is a historic manor—designed in the early 20th century by esteemed Reginald Davis Johnson—offering an impressive 29,483 square feet and including more than 30 rooms, all filled with an Old World sophistication and serenity. The property—which consists of 30 legal parcels—also encompasses 10 guest cottages, extensive equestrian facilities, and roughly 100 acres of citrus and avocado orchards, affording nearly unprecedented flexibility and opportunity.

Sag Harbor Getaway

Beside a private beach overlooking a ferry crossing, this enviable gated 3.5-acre two-home compound is secluded in the esteemed North Haven Point enclave, minutes from Sag Harbor Village and Shelter Island. Each of the two residences—an elegant five-bedroom primary home with ample space for entertaining and a light-filled five-bedroom guesthouse with water and sunset views—enjoys its own refreshing gunite swimming pool and lush manicured lawn.

Ranch Colony Retreat

This tranquil parklike 50-acre estate in the gated Ranch Colony community is one of southern Florida’s most exceptional properties. It features a five-bedroom Mediterranean-inspired main residence with views of its own four-acre lake, a glass-enclosed saltwater pool, a guesthouse, and extensive equestrian facilities. The property can be divided into two lots, allowing for great versatility, and can accommodate a variety of activities and pursuits, offering space for tennis courts and space for art, music, or an auto enthusiast’s garage.

Green Valley Ranch

This idyllic 950-acre ranch is a rare retreat of incomparable privacy protected from development by the Napa Land Trust. Just 15 minutes from Napa in a hidden valley, it includes five residences sited amid meadows, rolling golden hills, award-winning vineyards, stalwart oaks, dramatic rock outcroppings, and two dazzling lakes. This one-of-a-kind property enjoys sweeping views in every direction and is an ideal backdrop for unprecedented entertainment, relaxation, gardening, hobbies, and leisurely sports activities, including hiking and horseback riding.

Sophisticated Southwestern Oasis

This incomparable custom-designed home and guesthouse sit amid professionally landscaped grounds in the picturesque Taos Valley, reveling in true relaxation and spectacular mountain views. The single-level adobe main residence spans 3,429 square feet, and the 768-square-foot guest quarters are tucked above the garage and feature a full kitchen, a Murphy queen bed, a full bath, walnut flooring, a gas stove, and two portales. Enveloping the structures are mature trees, outdoor living spaces, and raised-bed gardens maintained by two wells and surface irrigation rights.

Originally published in June 16, 2020 by sothebysrealty