5 Winding Oaks DR, Pleasanton, CA 94566

$6,799,000 Active

4 Beds·4 Baths·5,761 sqft·145,738 sqft lot·Built 2021

5 Winding Oaks DR, Pleasanton, CA 94566

Listed 36 days ago · June 28, 2026 | MLS# ML82052124

$1,180/sqft +50% vs Pleasanton avg

What this means: Priced above the Pleasanton per-sqft average. Compare to recent sales below for context.

Est. $42,623/moP&I $35,279 · Tax $7,082 · Insurance $262 · HOA $0Assumes 20% down ($1,359,800) at 6.75% · Contact Timothy for a lender referralAegis Luxury Real Estate is a licensed California real estate brokerage (DRE# 01328224) and is not a mortgage lender, mortgage broker, or loan originator. The figures shown are estimates for general reference only and do not constitute a loan offer, pre-approval, pre-qualification, or commitment to lend. Estimates use the applicable county average property tax rate of 1.25% of home price annually. Actual rates, payments, taxes, and insurance vary by lender and borrower qualifications. Contact Timothy for a referral to one of our preferred lending partners.

Single Family Price Position in Pleasanton

Average $1.9M

Above typical range

$1.4M$3.1M

Why This Home Stands Out

📍

Pleasanton Location

Active listing in Pleasanton, Santa Clara County. Convenient access to schools, parks, and Bay Area employment centers.

🏠

4 Bed / 4 Bath / 5,761 sqft on 145,738 sqft Lot

Spec sheet at a glance. See full details below for interior, exterior, and lot features.

💰

Listed at $6.8M vs City Average $1.8M

$1,180/sqft compared to Pleasanton avg $785/sqft (+50.3%).

Best fit forActive BuyersPleasanton SearchersMove-Up / Move-In

About This Home

Newer construction! A rare gem this exceptional property is a must see. Situated on one of Pleasanton's most exclusive streets, this newly built Mediterranean Modern estate, completed in December 2021. This property rests atop a 3.35 acre oak studded lot with sweeping panoramic views of the valley. The formal entry opens to an expansive family room with soaring ceilings, seamlessly connecting to the chef's kitchen, which features a freestanding island, top of the line Thermador appliances, and a striking combination of white quartz and black granite countertops. A grand formal dining room showcases an impressive view of the valley an 800-bottle wine closet, ideal for collectors and entertainers. Down the main hallway are the formal living room with fireplace, a private office, and four bedrooms, including two ensuites. The magnificent primary suite offers two separate walk-in closets, and a spa inspired bathroom with dual vanities, a free-standing soaking tub, and an oversized walk-in shower. The resort style backyard includes an expansive pool with spa and a fully equipped outdoor kitchen and firepit perfect for year-round indoor-outdoor living. Newer construction 3.35-acre lot Single-story floor plan Panoramic views Custom luxury finishes Breathtaking Views!

MLS ID #ML82052124, Mona Lisa Weise. Listing provided by Compass · MLSListings Inc.

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Property Details

Property Type

Single Family Residence

Year Built

2021

Bedrooms

Bathrooms

3 Full, 1 Half

Living Area

5,761 sqft

Lot Size

145,738 sqft

Garage

3 Spaces

Price/sqft

$1,180

County

Alameda

MLS Number

ML82052124

Status

Active

Stories

N/A

HOA

None

Interior Features

CentralForcedAir

Exterior & Lot

Tile Roof3-Car Garage3.35 AcresPool

Location

This HomeActive ListingNew (3 days or less)Price ReducedOpen HouseSold

5 Winding Oaks DR, Pleasanton, CA 94566 · Alameda County

Market Context

Price Positioning

$ Price context: Listed at $1,180/sqft vs Pleasanton avg $785/sqft (+50.3% above).

$ Sale-to-list: Pleasanton homes selling at 98.6% of asking.

⏲ Velocity: City avg 35 days. This home: 36 days.

🏠 Inventory: 9 4-bedroom homes currently available in Pleasanton.

Source: MLSListings Inc. Timothy Alston, Broker, DRE# 01328224.

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Market Snapshot

$1,784,370Average Price-3.1% vs Last Year

35Avg DOM+29.6 days vs Last Year

24Active Listings+500.0% vs Last Year

98.6%Sale-to-List+0.7% vs Last Year

Full Market Snapshot →

Timothy Alston

Broker · DRE# 01328224

Aegis Luxury Real Estate

(408) 207-4593 [email protected]

For Homeowners

What would your Pleasanton home sell for today?

Homes in Pleasanton are selling at 98.6% of asking in 35 days.

98.6%Sale-to-List

35Avg Days

Get My Home's Value

Free. No obligation. Takes 30 seconds.

More in Pleasanton

4428 Del Valle PKWY$819,0003bd/2.5ba/1,280sf

444 Amaral CIR$1,699,8884bd/3ba/1,680sf

4428 Del Valle PKWY$829,8883bd/2.5ba/1,280sf

View All Listings →

Buyers and sellers researching Pleasanton_1 in Pleasanton will find 5 Winding Oaks DR to be a strong reference point. Listed at $6,799,000, this 4-bed, 4-bath home sits in a market where comparable properties average $785 per square foot. Homes in Pleasanton (94566) are currently averaging 35 days on market.

4-Bedroom Homes for Sale in Pleasanton 94566

Browse 4-bedroom single-family home listings in the Pleasanton_1 area of Pleasanton. Properties in 94566 are currently averaging $785 per square foot with 35 days on market.

What to Expect When Buying in Pleasanton_1

The Pleasanton_1 market in Pleasanton features a mix of single-family home properties ranging from starter homes to luxury estates. Current inventory levels suggest moderate conditions for buyers in this area.

Explore Pleasanton real estate

Pleasanton real estate listings List your home with Aegis Pleasanton real estate blog Pleasanton buyer guide Market analysis for Pleasanton

Recently Sold in Pleasanton

Closed within 6 months · 4 bed / similar sqft · Pleasanton 94566

7795 Olive DR

Sold $1,532,000

4 bd · 2.5 ba · 1,953 sqft
$784/sqft · 4.1% below list

Closed Jul 17, 2026 · 26 days on market

MLS ID #ML82045154, Samuel Spinella II. Listing provided by Real Brokerage Technologies · MLSListings Inc.

8158 Canyon Creek CIR

Sold $1,495,000

4 bd · 2.5 ba · 2,279 sqft
$655/sqft · +0.0% above list

Closed Jul 17, 2026 · 49 days on market

MLS ID #ML82051399, Serena Liu. Listing provided by Gaea Realty · MLSListings Inc.

3370 Morgan CT

Sold $1,580,000

4 bd · 2 ba · 2,029 sqft
$778/sqft · 1.2% below list

Closed Jul 01, 2026 · 34 days on market

MLS ID #ML82046371, Susan Berry. Listing provided by KW Advisors · MLSListings Inc.

Source: MLSListings Inc. Closed sales data.

For Homeowners

Your neighbors are selling. Should you?

In the last 3 months, 9 homes sold in Pleasanton at an average of $1,558,467. The average sale closed at 98.6% of asking price.

9Sold (Last 3 Months)

$1,558,467Average Sale Price

98.6%Sale-to-List

What is my home worth?Talk to Timothy

What happens when the right home lists and nobody knows you are looking for it?

In Pleasanton, Data pending new listings hit the MLS this week. By the time most search sites update, the window has already narrowed.

Get Alerts for Pleasanton Homes Like This →

Nearby Pleasanton Homes for Sale View All 20 →

New

$819,000

4428 Del Valle PKWY, Pleasanton

3 bed2.5 bath1,280 sqft

MLS ID #ML82052573, Gurjeet Rai. Listing provided by Doorlight Inc · MLSListings Inc.

New

$1,699,888

444 Amaral CIR, Pleasanton

4 bed3 bath1,680 sqft

MLS ID #ML82054227, Lex Orosco. Listing provided by Real Brokerage Technologies · MLSListings Inc.

New

$829,888

4428 Del Valle PKWY, Pleasanton

3 bed2.5 bath1,280 sqft

MLS ID #ML82045339, Gurjeet Rai. Listing provided by Doorlight Inc · MLSListings Inc.

Nearby Open Houses See All →

7750 Canyon Meadow CIR G, Pleasanton 94588

OPEN SAT, 1:30PM TO 4:30PM

$388,888

7750 Canyon Meadow CIR G, Pleasanton

2 bd · 2 ba · 1,043 sqft

MLS ID #ML82052276, Daniel Moskowitz. Listing provided by Coldwell Banker Realty · MLSListings Inc.

See All Open Houses This Weekend →

Pleasanton Market Overview Full Stats →

$1,558,467Avg Sale Price-3.1% vs Last Year

35Avg DOM+29.6% vs Last Year

24Active Listings

98.6%Sale-to-List

$785Price/sqft

8.0Months Inventory

9Closed (Last Mo)

Data pendingNew Listings/Mo

Source: MLSListings Inc. · August 2026

Frequently Asked Questions

Listed at $6,799,000 ($1,180/sqft). Pleasanton avg is $785/sqft, placing this +50.3% above. Comparable recent sales help frame the value.

Listed 36 days (as of June 28, 2026). Pleasanton average is 35 days.

Est. $42,623/mo with 20% down ($1,359,800) at 6.75%. Includes principal & interest ($35,279), property tax ($7,082), and insurance ($262). HOA: None. Aegis Luxury Real Estate is a licensed California real estate brokerage (DRE# 01328224) and is not a mortgage lender, mortgage broker, or loan originator. The figures shown are estimates for general reference only and do not constitute a loan offer, pre-approval, pre-qualification, or commitment to lend. Estimates use the applicable county average property tax rate of 1.25% of home price annually. Actual rates, payments, taxes, and insurance vary by lender and borrower qualifications. Contact Timothy for a referral to one of our preferred lending partners.

There are 24 active listings in Pleasanton (9 are 4-bedroom). At $6,799,000 this is positioned against the city average of $1,784,370. Similar homes have sold at 98.6% of asking.

4-bedroom homes in Pleasanton (94566) are currently averaging $785 per square foot. Market activity shows homes spending an average of 35 days on market in this area.

5 Winding Oaks DR in Pleasanton is currently listed at $6,799,000. This 4-bedroom, 4-bathroom single-family home is located in the Pleasanton_1 area.

Property Information © 2026 MLSListings Inc. All rights reserved. Certain information contained herein is derived from information which is the licensed property of, and copyrighted by, MLSListings Inc.

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 Aegis Luxury Real Estate are marked with the Internet Data Exchange icon (a stylized house) and detailed information about them includes the names of the listing brokers and listing agents.

Based on information from the MLSListings MLS as of Aug 3, 2026 10:30 PM PT. 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.

These statistics are generated using information from the MLSListings Inc. multiple listing service, but have not been verified and are not guaranteed. MLSListings Inc. disclaims any responsibility for the accuracy and reliability of these statistics. This information should not be relied upon for real estate transaction decisions.

Data updated every 15 minutes. Visit www.MLSListings.com for more information.

Information provided is for general informational purposes only. Equal Housing Opportunity. If you are currently working with a real estate agent, this is not intended as a solicitation.

Timothy Alston, Broker, DRE# 01328224, Aegis Luxury Real Estate, 10080 N. Wolfe Rd Ste SW3-200, Cupertino CA 95014. (408) 207-4593.

Last updated: Aug 3, 2026 10:30 PM PT | Source: MLSListings Inc.

All content on this page is the property of Aegis Luxury Real Estate (DRE# 01328224). Automated scraping, downloading, or republication is strictly prohibited.

Why This Home Stands Out

About This Home

Property Details

Interior Features

Exterior & Lot

Location

Market Context