luxury properties for sale Monterey County, United States

Rare opportunity in Old Town Monterey! Two charming Spanish-style homes on one parcel, just blocks from the heart of downtown Monterey. So many possibilities. Perfect for an investor, or live in one and rent out the other. The front residence at 355 Monroe features 3 bedrooms, 1 bathroom, and approximately 850 square feet of living space, while 357 Monroe offers 2 bedrooms, 1.5 bathrooms, and approximately 1,092 square feet, with convenient access from Eddie Burns Lane and an attached garage. A fenced yard separates the two residences, creating privacy and distinct outdoor spaces for each home. Full of character, the property features charming architectural details, hardwood floors, a fireplace, inviting outdoor areas, and a peek of the Monterey Bay from the deck at 357. Enjoy the flexibility of two detached residences while being moments from downtown Montereys restaurants, shops, waterfront, and all that the highly desirable Old Town neighborhood has to offer.

Some properties can be seen; a few can be felt, so come experience the difference. Tucked into the rolling hills of the San Antonio Valley AVA and the Jolon Road Wine Corridor, this 10+ acre California retreat offers a rare blend of rural charm, wine country lifestyle, and everyday livability, just far enough from it all to feel like an escape and close enough to make it your everyday. At the heart of the property is a thoughtfully built 2,185± square-foot home, completed in 2001 with Tuscany-like views, smooth stucco exterior, and interior soundproofing. The open layout includes 3 bedrooms and 2 bathrooms plus a family room, allowing space to host, unwind, or work remotely while looking out over your own vines. The 4.5± acres of Cabernet Sauvignon vines are twenty-two years old now, enough to have deep roots and a story of their own, farmed without chemicals, shaped by hot days, cool nights, and calcareous soil. A half acre of Sagrantino, a celebrated Italian varietal rarely found in this region, bordered by a neighboring Malbec vineyard, adds to the sense of an established wine-growing enclave. The turnkey, fully permitted (ABC) winery includes a tank room, crush pad, and case and bottle storage, with an open-air tasting room patio made for sharing a glass while the sun sets over the vines. The property's history of hosting a wine club and Harvest Host guests points to built-in potential for a new owner to launch similar income streams from day one, with room to grow production further. Sustainability runs throughout the property, with 36 solar panels and 2 Tesla Powerwall 3 batteries keeping the home and winery running efficiently, plus a reliable well, irrigation, and new backflow system supporting the vines. For future flexibility, the property also offers enough space for ADU potential, opening the door to additional living space, a guest suite, or hosting quarters. This is more than a hobby vineyard; it's an invitation to a slower pace, wider skies, and the daily rhythm of tending vines and making wine on your own land. Set within reach of Paso Robles and the greater Monterey wine region, it's a lifestyle property built for those who want to be part of the story, not just the scenery. This working vineyard estate comes with real history in the ground and a next chapter waiting to be written.