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$6,495,888 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 5,761 Sq. Ft.
  • 3 Car Garage
  • Updated 14 hours ago

Next open house:

Open House: 1:00 PM - 4:00 PM

Saturday 8/29 1:00 PM - 4:00 PM

5 Winding Oaks Dr,Pleasanton, CA 94566

5 Winding Oaks DrPleasantonCA94566

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Join us at 5 Winding Oaks Dr on:

  • Open House: 12:30 PM - 3:00 PM

    Sunday 8/30 12:30 PM - 3:00 PM

    5 Winding Oaks Dr,Pleasanton, CA 94566
    5 Winding Oaks DrPleasantonCA94566
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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.

Full Property Details for 5 Winding Oaks Dr

General

  • Price: $6,495,888
  • Status: Active
  • Type: Single Family
  • Source: RE_Infolink
  • MLS ID: ML82059150
  • Updated: 8/27/2026
  • Added to Site: Today

Interior

  • Rooms/Areas: Office Area, Wine Cellar / Storage, Formal Entry, Laundry Room
  • Interior Features: High Ceiling , Skylight, Vaulted Ceiling , Walk-In Closet, Wet Bar
  • Fireplace(s): Family Room, Primary Bedroom
  • Flooring: Hardwood, Tile, Other

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Bathroom Features: Double Sinks, Stall Shower, Tile, Oversized Tub, Showers over Tubs (2 or More), Primary - Stall Shower(s)

Bedrooms

  • Total Bedrooms: 4
  • Bedroom Features: Primary Suite / Retreat, Walk-In Closet

Other Rooms

  • Family Room: Separate Family Room
  • Kitchen: Island with Sink, Garbage Disposal, Hood over Range, Island, Microwave, Built-In Oven, Double Oven, Self-Cleaning Oven, Pantry, Gas Oven/Range, Wine Refrigerator, Refrigerator
  • Laundry: Gas Hookup, In Garage, Electricity Hookup (220V), Washer / Dryer, In Utility Room, Inside

Additional Information

  • Pool: Yes
  • Pool Description: Pool - In Ground, Solar-Heated
  • Extras: Not Applicable

Parking

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

Location

  • Area: Pleasanton
  • County: Alameda
  • Cross Streets: Thiesen

Heating & Cooling

  • Cooling Type: Central AC, Multi-Zone
  • Heating Type: Central Air (Forced Air)

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Public Utilities

Structural Information

  • Architectural Style: Mediterranean
  • Construction: Detached, Stucco
  • Foundation: Concrete Perimeter
  • Roof: Tile
  • Square Feet: 5,761
  • Year Built: 2021

Lot Features

  • Property View: Valley
  • Lot Size (Acres): 3.3457
  • Minimum Lot Size: 145737
  • Lot Size (Sq. Ft.): 145,737
  • Grounds/Landscape: Back Yard, Fenced, Firepit, BBQ Area
  • Zoning: .
  • Lot Description: Views, Flag-Shaped Lot, Private / Secluded
  • Fencing (Description): Fenced Back

Green Features

  • Energy Efficient: Solar-Heated Pool, Solar Power, Skylight, Energy Star Appliances

Listed by Compass, Mona Lisa Weise

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Listing agent

— 5 Winding Oaks Dr —

  • Mona Lisa Weise

    Compass

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5 Winding Oaks Dr

School District:Pleasanton Unified School District
NameGradesDistance
Vintage Hills Elementary School
1125 Concord Street, Pleasanton, CA 94566
K-51.2 mi
Harvest Park Preschool Center
4900 Valley Avenue, Pleasanton, CA 94566
PK-3.1 mi
Pleasanton Middle School
5001 Case Avenue, Pleasanton, CA 94566
6-82.9 mi
Amador Valley High School
1155 Santa Rita Road, Pleasanton, CA 94566
9-122.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5 Winding Oaks Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/27/2026
Listed
$6,495,888
145.17%
MLS
10/20/2022
Sold
$2,649,500
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5 Winding Oaks Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$70,264
—
$6,120,000
2%
2025
$70,264
-4%
$6,000,000
-4%
2024
$72,835
10%
$6,221,592
11%
2023
$66,233
77%
$5,609,600
71%
2022
$37,373
89%
$3,273,610
88%
2021
$19,808
53%
$1,742,227
53%
2020
$12,936
-1%
$1,142,400
2%
2019
$13,096
11%
$1,120,000
11%
2018
$11,842
3%
$1,013,045
2%
2017
$11,538
8%
$993,188
2%
2016
$10,652
2%
$973,717
2%
2015
$10,452
-2%
$959,100
2%
2014
$10,642
-2%
$940,317
—
2013
$10,826
—
$936,076
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 5 Winding Oaks Dr

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NMLS#: 1598647

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Listed by Compass, Mona Lisa Weise

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5 Winding Oaks Dr, Pleasanton, CA 94566 (MLS# ML82059150) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 5 Winding Oaks Dr is currently listed for $6,495,888 and was received on August 27, 2026. Want to learn more about 5 Winding Oaks Dr? Do you have questions about finding other Single Family real estate for sale in Pleasanton? You can browse all Pleasanton real estate or contact a Coldwell Banker agent to request more information.

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