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5 Winding Oaks DrivePleasanton, CA 94566

For Sale

$6,495,888

Smart Buyer Rebate $64,959

Newer Construction-Luxury Single-Story Estate-3.35 Acres-Panoramic Views. A rare gem, this exceptional Mediterranean Modern estate was completed in December 2021. Situated on one of Pleasanton's most exclusive streets, offering breathtaking panoramic valley views, the grand formal entry opens to an expansive great room with soaring ceilings, seamlessly flowing into the chef's kitchen. Designed for everyday entertaining, the kitchen features a large freestanding island, top-of-the-line Thermador appliances, and a striking blend of white quartz and black granite countertops. The formal dining room showcases spectacular views and is complemented by an impressive 800-bottle wine cellar, perfect for collectors and entertainers alike. The thoughtfully designed single-story floor plan also includes a formal living room with a fireplace, a private office, and four spacious bedrooms, including two en-suite bedrooms. The luxurious primary suite serves as a private retreat, offering dual walk-in closets and a spa-inspired bath with dual vanities, a freestanding soaking tub, and an oversized walk-in shower. Step outside to the resort-style backyard, where an expansive pool and spa, fully equipped outdoor kitchen and a fire pit to create the perfect setting for year-round entertaining.

Listed by Mona Lisa Weise

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License #01408750

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Compass

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408-221-0627

Last updated August 27, 2026

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Source: MLSListings #ML82059150

Listing Facts

  • TypeSingle-family
  • NeighborhoodEast Vineyard Avenue
  • Bedrooms4
  • Days on Prevu19
  • Size5,761 sqft
  • Price per sqft$1,128

Amenities

  • Private Outdoor Space
  • Pets Allowed
  • Parking
  • Swimming Pool

Location

Mortgage Calculator

Listing History

08/27/2026
Listed by Compass
$6,495,888
  1. 08/27/2026$6,495,888
    Listed by Compass

Property Details for 5 Winding Oaks Drive

Exterior

Construction

  • Roof: Tile
  • Stories: 1
  • Year Built: 2021
  • Year Built Details: 2
  • Architectural Style: Mediterranean

Features

  • Fencing: Fenced Back
  • Patio And Porch Features: Back Yard, Barbecue Area, Fenced, Fire Pit
  • Pool Features: Heated - Solar, In Ground
  • View: Valley

Measurements

  • Building Area Total: 5,761
  • Lot Features: Flag Lot
  • Lot Size Acres: 3.34
  • Lot Size Area: 145,737
  • Lot Size Source: Assessor
  • Lot Size Square Feet: 145,737
  • Lot Size Units: Square Feet

Financial

Taxes

  • Parcel Number: 946-4611-006

Interior

Features

  • Appliances: Garbage Disposal, Hood Over Range, Microwave, Oven - Built-In, Oven - Double, Oven - Self Cleaning, Oven Range - Gas, Refrigerator, Wine Refrigerator, Washer/Dryer
  • Fireplace Features: Family Room, Primary Bedroom
  • Fireplaces Total: 2
  • Flooring: Hardwood, Other, Tile
  • Interior Features: High Ceiling, Skylight(s), Vaulted Ceiling, Wet Bar, Walk-in Closet

Measurements

  • Living Area: 5,761

Rooms

  • Bathrooms Full: 3
  • Bathrooms Half: 1
  • Bedrooms Total: 4

Parking

Parking

  • Attached Garage: Yes
  • Garage Spaces: 3
  • Garage: Yes
  • Parking Features: Attached Garage, Off-Site Parking, Other

Schools

Elementary School

  • Elementary School District: Pleasanton Unified

High School

  • High School District: Pleasanton Unified

Utilities

Equipment

  • Cooling: Central Forced Air, Multi-Zone
  • Heating: Central Forced Air
  • Laundry Features: Hookup - Gas Dryer, In Garage, Inside, In Utility Room
  • Sewer: Public Sewer
  • Utilities: Public Utilities, Water - Public, Solar
  • Water Source: Public

Frequently Asked Questions

How many bedrooms does this single-family home have?

There are 4 bedrooms in this single-family home at 5 Winding Oaks Drive.

Does this single-family home have parking?

Yes, there are 3 parking spaces available for 5 Winding Oaks Drive.

How does 5 Winding Oaks Drive compare to other single-family homes in East Vineyard Avenue?

This single-family home is listed 33% above the average price for single-family homes in East Vineyard Avenue and has been on the market for 48 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 5,761 sqft.

5 Winding Oaks Drive is a 4-bedroom single-family home for sale in Pleasanton CA 94566. Listed on Prevu for 19 days at $6,495,888. This home features 5,761 square feet of living space, located in Pleasanton. The median listing price for single-family homes in this area is $4,887,000. Additional amenities include private outdoor space, pets allowed, parking, and swimming pool. Explore more single-family home listings in Pleasanton.

The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListings™️ MLS system. Real estate listings held by brokerage firms other than Prevu Real Estate are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents. Based on information from the MLSListings MLS) as of 08/27/2026. All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Data Services by Constellation Data Labs. IDX display powered by Prevu Real Estate. Copyright 2026 MLSListings Inc. All rights reserved.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.