2875 Woolsey Road, Windsor, CA 95492, Windsor, 95492 - 5 bed, 4 bath
2875 Woolsey Road
Windsor, CA 95492
Property Price
SUMMARY
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.
Condition Analysis
OVERALL CONDITION SCORE
Property is move-in ready.
Despite its 1888 build date, this historic estate is in move-in ready condition and has been meticulously maintained for over 40 years. The property features a custom kitchen with a large pantry, a grand primary bathroom, and modern amenities that seamlessly blend with its original Victorian charm. With a restored 5,000 sqft barn, updated outdoor entertaining areas, and high-end finishes throughout, the home shows minimal wear and tear and functions at a high standard, though it lacks the 'newly built' status required for an excellent rating.
PROSSTRENGTHS & OPPORTUNITIES
- High Available Lot Utilization
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.
- Income-Generating Vineyards
The estate includes nearly 10 acres of premium Pinot Noir and Chardonnay vineyards contracted with esteemed wineries, providing immediate agricultural value and income potential.
- Historic Architectural Integrity
Built in 1888, the 'Oakmead' estate is a meticulously preserved Victorian masterpiece that seamlessly blends 19th-century charm with modern luxury across a spacious 4,747 sqft floor plan.
CONSRISKS & DEFICIENCIES
- MLS Listing Discrepancy
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.
- High Maintenance Demands
Managing 17.5 acres of manicured gardens, ponds, and multiple historic structures requires significant ongoing labor and financial investment for proper upkeep.
- Vintage Infrastructure Risks
Despite being well-maintained, the 1888 construction date implies potential challenges with older systems or structural elements that may require specialized care and higher insurance costs compared to modern builds.
About 2875 Woolsey Road
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.
Property Details
Public Facts
- Property Type
- Single Family Residence
- Year Built
- 1888
- Lot Size
- 762,300 Sq. Ft.
Interior
- Total Bedrooms
- 5
- Total Bathrooms
- 4 (4 Full, 0 Half)
Exterior & Parking
No exterior & parking available.
Utilities & Misc
- HOA Fee
- $0 / Month
Neighborhood Insights
Sensitive Facilities
No sensitive facilities data found.
Neighborhood Comparison
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 5.0 | 4.0 | 93% |
| Baths | 4.0 | 3.0 | 90% |
| Square foot | 4,747 | 1,966 | 99% |
| Lot Size | 762,300 | 6,599 | 99% |
| Price | $3.90M | $850.0K | 99% |
| Price per sq ft | $822 | $441 | 97% |
| Built year | 1888 | 1991 | 1% |
| HOA | $0 | $0 | 50% |
| Days on market | 35 | 185 | 3% |
Pricing History
Listed for Sale
Jan 31, 2026
$3,900,000
Initial Listing