2875 Woolsey Road, Windsor, CA 95492, Windsor, 95492 - 5 bed, 4 bath
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Windsor, CA 95492
Analysis of 2875 Woolsey Road, Windsor, CA 95492 is currently available with a list price of $3,900,000. The property maintains a Good Condition Rating (78/100), reflecting solid structural condition with well-maintained systems. The property presents an attractive opportunity for buyers seeking a move-in ready home. Located in a high-demand neighborhood within the Windsor Unified School District, this asset is categorized as a low-risk, high-reward acquisition suitable for both Buy-and-Hold Investors and Owner-Occupants willing to undertake light renovation work.
Property is move-in ready.
This 1888 Victorian estate, known as Oakmead, is in exceptional condition and appears move-in ready. The property has been meticulously maintained, featuring a custom kitchen with high-end stainless steel appliances (including a Jenn-Air refrigerator), stone countertops, and updated cabinetry. The interior showcases well-preserved historic details like original woodwork and hardwood flooring, complemented by modern light fixtures and five functional fireplaces. The exterior and grounds are equally well-kept, including a fully restored 5,000 sqft barn and manicured gardens. While the home is historic, its systems and finishes have been updated to meet modern standards, fitting the 'Good' criteria for a property that is well-maintained with no immediate renovation required.
The property has a large lot size, which is more than 4 times of its living area. lot size in square feet = 762300, living area = 4747.
The estate features nearly 10 acres of premium Pinot Noir and Chardonnay vineyards already contracted with esteemed wineries, providing immediate agricultural value and income potential.
In addition to the main 1888 Victorian, the property includes a 5,000 sqft restored barn, a detached guest cottage, and an art/exercise studio, offering exceptional flexibility for guests or creative pursuits.
Lot size discrepancy between mls listing and other public or private record. mls listing lot size in square feet =762300, other record lot size in square feet = 760557. Bedroom count discrepancy between mls listing and other public or private record. mls listing bedroom count = 5, other record bedroom count = 3.
The scale of the 17.5-acre lot, combined with multiple historic structures and active vineyards, necessitates significant ongoing labor and financial investment for proper upkeep.
As an 1888 build, the main residence may present challenges regarding energy efficiency and modern utility standards that are common in century-old Victorian estates.
Experience Oakmead, an exquisitely preserved estate in Russian River Valley. Built in 1888, this historic Sonoma County property overlooks 17.5 acres with 9.68 acres of picturesque Pinot Noir & Chardonnay vineyards contracted with esteemed wineries. Lovingly maintained for over 40 years by the same family, Oakmead seamlessly blends its original Victorian charm with modern amenities. Explore winding pathways through rose gardens, ponds, fountains, & manicured lawns, leading to a restored 5,000 sqft barn, art/exercise studio w/ half bath & an independent 2bed/1bath cottage. Additional features include wine cellar, multiple outbuildings & a detached two-car garage. The main residence, nestled amidst lush gardens, offers an outdoor kitchen, fire-pit & expansive patio for entertaining. The first floor showcases an elegant primary suite with walk in closet & grand bathroom, custom kitchen with large pantry & breakfast nook open to a cozy family room with one of five fireplaces. Rounding out the main floor is the sunroom, library, formal dining & living room with adjacent music room & a versatile office suite with full bath. Upstairs includes four bedrooms, a full bath & expansive views. Immerse yourself in the rich history & luxurious amenities of Oakmead, a rare wine country gem.
No exterior & parking available.
No sensitive facilities data found.
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 5.0 | 3.5 | 89% |
| Baths | 4.0 | 3.0 | 87% |
| Square foot | 4,747 | 1,990 | 99% |
| Lot Size | 762,300 | 6,784.5 | 99% |
| Price | $3.90M | $815.0K | 99% |
| Price per sq ft | $822 | $424 | 96% |
| Built year | 1888 | 1991 | 1% |
| HOA | $0 | $0 | 50% |
| Days on market | 81 | 206 | 21% |
Jan 31, 2026
$3,900,000
Initial Listing