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211 Winding Way, Woodside, CA 94062, US
Copied

$25,000,000

For Sale - Active
211 Winding Way, Woodside, CA 94062
6 Beds
8 Baths
7,930 Square Feet
4.40 Acres Lot
Built in 1997
For Sale - Active
Units n/a
Checked: 13 hours ago
Updated: Sep 27, 2025 at 10:02AM

Investment Summary


Potential Missing Expenses

We noticed that property taxes are missing—this is a standard expense and should be considered in your estimate.

Monthly Cash Flow
-$110,649
Cap Rate
0.4%
Cash-on-Cash Return
-23.1%
Debt Coverage Ratio
0.06
Internal Rate of Return (5 years)
-18.3%

Property Description


4.40 Acres Lot
Built in 1997
For Sale - Active
Units n/a

A rare offering on one of Central Woodsides most prestigious streets, just off Mountain Home Road, this extraordinary estate showcases architectural excellence, vineyard beauty, & a luminous natural setting. Spanning almost 4.4 acres with an optional adjacent 3-acre parcel also available, the grounds have been thoughtfully opened to invite abundant sunlight, enhancing both the ambiance and the usability of the land. Designed by Ugo Sap and built by Van Acker Construction, the main residence is defined by dramatic scale, elegant curved forms, and exceptional materials. An elevator connects the two levels, which include six en suite bedrooms including a show stopping primary suite with terrace and spa bath beneath a retractable skylight. The library has walnut paneling and custom wood cabinetry with custom inset lighting. Outdoor living is equally impressive, featuring a thriving Pinot Noir vineyard, olive orchard, and multiple destinations for entertaining. A spacious poolside guest house includes a bedroom, full kitchen, sauna, and bath, while a separate structure with bath and kitchenette is ideal for a fitness center or executive office. Plus a building which has temperature controlled wine storage. A truly world-class property with access to acclaimed Woodside School.

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Location


Property Details


Parking

  • Description: Electric Vehicle Charging Station(s), Gated, Guest
  • Details: Attached, Guest, Garage
  • Garage Spaces: 3
  • Spaces Total: 0

Bedroom Information

  • # of Bedrooms: 6

Bathroom Information

  • # of Baths (Full): 6
  • # of Baths (Partial): 2
  • # of Baths (Total): 8.0

Interior Features

  • # of Stories: 2
  • Fireplace: Yes

Exterior Features

  • Exterior Walls Materials: Stucco
  • Pool: Yes

Land Information

  • Land Use: Residential
  • Land Use Subtype: Single Family Residential

Lot Information

  • Parcel ID: 072203120
  • Lot Size: 191612 sqft

Property Information

  • Property Type: Single Family Residence
  • Year Built: 1997

Tax Information

  • Annual Tax: $0

Utilities

  • Heating: Forced Air, Zoned
  • Cooling: Central Air

Location

  • County: San Mateo

Listing Details


Listed by:
Compass
(650) 888-0860

Source:
bridgeMLS
MLS#: ML82012031
bridgeMLS

Investment Summary


Potential Missing Expenses

We noticed that property taxes are missing—this is a standard expense and should be considered in your estimate.

Monthly Cash Flow
-$110,649
Cap Rate
0.4%
Cash-on-Cash Return
-23.1%
Debt Coverage Ratio
0.06
Internal Rate of Return (5 years)
-18.3%

Purchase Details

Find an Agent

Purchase price:
$25,000,000
Amount financed:
-$20,000,000
Down payment:
$5,000,000
Closing costs:
$750,000
Rehab costs:
$0
Initial cash invested:
$5,750,000
Square feet:
7,930
Cost per square foot:
$3,153
Monthly rent per square foot:
$1.40

Financing Details

Find a Lender

Loan amount:
$20,000,000
Loan to value ratio:
80.0%
Loan type:
Amortizing
Term:
30 years
Interest rate:
5.875%
Principal & interest:
$118,308
Property tax:
$0
Insurance:
$777
Private mortgage insurance (PMI):
$0
Monthly payment:
$119,085

Operating Income

Find a Property Manager

% Rent Monthly Yearly
Gross rent:
$11,100 $133,200
Vacancy loss: (6%)
6% -$666 -$7,992
Operating income:
$10,434 $125,208

Operating Expenses


% Rent Monthly Yearly
Property taxes: (n/a)
n/an/an/a
Insurance: (7%)
7%-$777-$9,324
Property management: (8%)
8%-$888-$10,656
Repairs & maintenance: (5%)
5%-$555-$6,660
Capital expenditures: (5%)
5%-$555-$6,660
HOA fees: (n/a)
n/an/an/a
Total operating expenses: (25%)
25%-$2,775-$33,300

Cash Flow


Monthly Yearly
Net operating income:
$7,659 $91,908
Mortgage payments:
-$118,308 -$1,419,696
Cash flow:
-$110,649 -$1,327,788