2875 Woolsey Road, Windsor, CA 95492, Windsor, 95492 - 5 bed, 4 bath
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Windsor, CA 95492
This historic 1888 Victorian Vineyard Estate is a Strong Value Opportunity, listed at $3,495,000—positioned well below the $3,692,618 Fair Market Value by 5%. This valuation gap offers $197,618 in Instant Equity. Featuring a Condition Rating of 3, the estate includes 17.5 acres, 8 acres of Chardonnay vineyards, and a restored 5,000 sqft barn. This rare compound is ideal for Buy-and-Hold Investors or Owner-Occupants seeking a luxurious, income-producing wine country sanctuary.
Comparables within 1 miles sold in recently
| Address | Sold Price | Beds | Baths | Sq Ft | $/Sqft | Distance |
|---|---|---|---|---|---|---|
★ 2875 Woolsey Road Subject | $3,495,000* List Price | 5 | 4 | 4,747 | $778 | - |
A 2875 Woolsey Road Active | $3,900,000 List Price | 5 | 4 | 4,747 | $822 | 0.0 mi |
* Subject property listed price vs sold prices of comps.
Property is move-in ready.
Despite being built in 1888, this historic estate has been meticulously maintained with high-end renovations. The custom kitchen features modern stainless steel appliances, and the bathrooms have been updated with premium cabinetry and fixtures. The property shows no signs of deferred maintenance and offers modern amenities, placing it in the 5-15 year renovation category.
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.
Oakmead Ranch is a rare 1888 Victorian estate featuring 17.5 acres of land with 8 acres of income-producing Chardonnay vineyards in the prestigious Russian River Valley.
The property includes a 5,000 sqft restored barn, a separate 2-bedroom guesthouse, and an art/exercise studio, providing exceptional space for guests, hobbies, or multi-generational living.
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.
Given the 1888 construction date and the scale of the 17.5-acre grounds and multiple outbuildings, the property will demand significant ongoing maintenance and preservation efforts.
The second floor contains four bedrooms served by only one full bath, which may be considered a functional limitation for modern luxury buyers at this price point.
Incredible Russian River Valley Vineyard Estate. Built in 1888, Oakmead Ranch is a historic Sonoma County property overlooking 17.5 acres with approximately 8 acres of picturesque Chardonnay vineyards. 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 & a separate 2bed/1bath cottage/guesthouse with with a full kitchen. 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 | 3.0 | 89% |
| Baths | 4.0 | 3.0 | 85% |
| Square foot | 4,747 | 2,031 | 98% |
| Lot Size | 762,300 | 6,970 | 98% |
| Price | $3.50M | $800.0K | 95% |
| Price per sq ft | $736 | $421 | 95% |
| Built year | 1888 | 1990 | 2% |
| HOA | $0 | $0 | 50% |
| Days on market | 6 | 196 | 2% |
May 31, 2026
$3,495,000
Initial Listing