5 California Trophy Homes and Acreage from San Francisco to Napa

Originally built in 1885, 250 Douglass Street stands as a rare heritage trophy property in the heart of Eureka Valley, designated a San Francisco Landmark (#80) in 1975. Once a grand private residence, the Baroque Queen Anne main building now comprises 14 individually designed, tenant-occupied apartment units, each separately metered for PG&E and defined by its own layout and architectural character. A grand entry hall with stained glass windows, detailed woodwork, and a central staircase sets the tone on arrival, echoed outside by a commanding façade, shingled roof, and distinctive towers. Practical amenities include two sets of coin-operated washers and dryers and a single-car garage leased separately. The offering also includes an adjacent RH-2 zoned buildable lot with a rentable studio cottage, plus a two-room office space with bathroom access and reconfiguration potential, subject to approvals—all moments from transit, the Castro District, Kite Hill, and Dolores Park.

Price: Contact for pricing

Set on 70.3 acres along Monticello Road in Napa, 2846 Monticello Rd offers a rare sense of space and quiet in wine country. The residence spans 2,996 square feet with three bedrooms and two bathrooms, providing a comfortable footprint for everyday living and unhurried weekends alike. With so much land to call your own, the experience here is defined as much by what surrounds the house as what’s inside—room to roam, time outdoors, and the simple luxury of distance from the bustle. Tucked within the Napa, CA 94558 area, this is a property that invites a slower rhythm, where mornings can begin with wide-open acreage and evenings can settle into the calm that only a large holding can provide.

Size: 70.00 acres

Along the San Francisco Bay’s sweeping horizon in the heart of Carneros, this storied Stornetta Dairy holding spans lush meadows and open land with far-reaching views to the Bay and beyond. The landscape lends itself to a range of rural pursuits—horse ranching, cattle grazing, or planting grapes—supported by analysis from Paul Anamosa indicating approximately 70 acres of plantable vineyard land. Gentle breezes cool the site, creating conditions suited to Chardonnay, Sauvignon Blanc, or Pinot Noir. Practical infrastructure is already in place, including one well and a 10 acre-foot pond. Offered as vacant land, the property is a canvas for shaping a dream home, horse ranch, or winery, with the Carneros setting as a constant backdrop for daily life outdoors.

Size: 187 acres

Behind the gates of Monterra—one of the Monterey Peninsula’s most sought-after private communities—this beautifully crafted 2017 custom-built residence is designed for single-level California Coastal living. Premium finishes set a refined tone throughout, while indoor-outdoor flow shapes the day-to-day experience, from quiet mornings to easy evenings with friends. A glass-wrapped dining alcove brings in light and creates a distinctive place to gather, framed by the home’s thoughtful, contemporary craftsmanship. Outside, an outdoor fire pit extends the living space and invites long conversations after sunset. Two separate two-car garages add flexibility for storage and daily arrivals. Positioned just moments from Pebble Beach, the Club at Tehama, Laguna Seca, and the best of the Monterey Peninsula, life here balances privacy with effortless access to the region’s signature destinations.

Steps from San Francisco’s waterfront, this voluminous South Beach residence channels the city’s maritime history through a distinctly modern industrial lens. A massive wall of floor-to-ceiling glass washes the interior in light, emphasizing timber beams, industrial steel accents, and walnut floors—scale that easily accommodates large-format art and sophisticated living. Set within a 19th-century warehouse, the space balances a rugged backdrop with high-end finishes throughout. The remodeled chef’s kitchen is conceived for both utility and hosting, with exposed concrete walls, heavy timber, and a 9-foot social island that anchors culinary prep and dining. Outside, a private gated patio creates a tranquil urban oasis. Daily life stays effortlessly connected, with tech shuttles, Caltrain, and the Ferry Building close at hand, plus rare side-by-side two-car parking.