109 photos · MLS data verified October 8, 2026 · Updated every 15 min
$6,495,888
ActiveUnderContract
4 Beds·4 Baths·5,761 sqft·145,737 sqft lot·Built 2021
5 Winding Oaks Dr, Pleasanton, CA 94566
Listed 42 days ago · | MLS# ML82059150
$1,127/sqft
5 Winding Oaks Dr is a single-level, 4-bedroom, 4-bath single family home in Pleasanton 94566 with 5,761 square feet of living space, built in 2021. It is listed at $6,495,888, or $1,127 per square foot. The three most recent 4-bedroom sales in 94566 closed between $1,290,000 and $1,850,000 ($780 to $906 per square foot).
Est. $40,734/moP&I $33,706 · Tax $6,767 · Insurance $262 · HOA $0Assumes 20% down ($1,299,178) 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 a 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
$1.4M$3.1M
18Active in Pleasanton
10Active Single Family Homes
3.6 moInventory
Why This Home Stands Out
🏠
Single Level, 4 Bed / 4 Bath, 5,761 sqft
Everything on one floor. Built in 2021, attached 3-car garage.
Best fit forActive BuyersPleasanton SearchersMove-Up / Move-In
About 5 Winding Oaks Dr
Gated Estate community! 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 private 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 includes a formal living room with a fireplace, a private office, and four spacious bedrooms, including two en-suite bedrooms. The 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 a setting for year-round entertaining.
MLS ID #ML82059150, Mona Lisa Weise. Listing provided by Compass · MLSListings Inc.
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Property Details for 5 Winding Oaks Dr
Overview
- Property Type
- Single Family Residence
- Year Built
- 2021
- Stories
- 1
- Bedrooms
- 4
- Bathrooms
- 3 Full, 1 Half
- Living Area
- 5,761 sqft
- Lot Size
- 145,737 sqft (3.35 acres)
- Price/sqft
- $1,127
- Status
- ActiveUnderContract
Interior
- Primary Bedroom
- Primary suite retreat, Walkin closet
- Kitchen
- Island, Islandwith sink, Pantry
- Appliances
- Garbage disposal, Hood over range, Microwave, Oven built in, Oven double, Oven self cleaning, Oven range gas, Refrigerator, Wine refrigerator, Washer dryer
- Fireplace
- Family room, Primary bedroom
- Heating
- Central forced air
- Cooling
- Central AC, Multi, zone
- Flooring
- Hardwood, Other, Tile
- Laundry
- Hookup, gas dryer, In garage, Inside, In utility room
- Family Room
- Separate family room
- Interior Features
- High ceiling, One or more skylights, Vaulted ceiling, Wet bar, Walkin closet
Exterior and Parking
- Garage
- Attached, 3 spaces
- Roof
- Tile
- Foundation
- Concrete perimeter
- Pool
- Heated, solar, In ground
- View
- Valley
- Lot Features
- Flag lot
- Fencing
- Fenced back
- Zoning
- .
Community and HOA
- Utilities
- Public, Water public, Solar
- County
- Alameda
- City
- Pleasanton
Schools
- School District
- Pleasanton Unified
- Pleasanton Schools
- View Pleasanton schools
Listing
- MLS Number
- ML82059150
- Listed
- August 27, 2026
- Days on Market
- 42
- Listing Agent
- Mona Lisa Weise
- Listing Brokerage
- Compass
- Data Verified
- October 8, 2026
Source: MLSListings Inc. School attendance boundaries are set by the district and can change; verify directly with the district.
Free from Aegis · Updated for October 2026
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Location
5 Winding Oaks Dr, Pleasanton, CA 94566 · Alameda County
Market Context
Price Positioning
🏠 Inventory: 2 4-bedroom homes and 10 single family homes currently active in Pleasanton.
Source: MLSListings Inc. Timothy Alston, Broker, DRE# 01328224.
Want to know what this home will actually sell for? Get a data-backed offer range based on recent comparable sales.
Get My Offer Range →Frequently Asked Questions
Listed at $6,495,888 ($1,127/sqft). The three most recent 4-bedroom sales in 94566 closed at $780 to $906 per sqft.
Listed August 27, 2026. That is 42 days on market as of October 8, 2026.
Est. $40,734/mo with 20% down ($1,299,178) at 6.75%. That is principal and interest $33,706, property tax $6,767 and insurance $262. The assumptions and lender disclosure are with the payment estimate at the top of this page.
There are 18 active listings in Pleasanton: 2 are 4-bedroom and 10 are single family homes.
The three most recent 4-bedroom sales in Pleasanton 94566 closed at $1,290,000, $1,800,000 and $1,850,000, or $780 to $906 per sqft.
Yes. As of October 8, 2026, 5 Winding Oaks Dr is an active listing at $6,495,888. It is a 4-bedroom, 4-bath single family home.
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Buyers
See 5 Winding Oaks Dr before the weekend
Listed 42 days ago.
Questions
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Timothy Alston, Broker, DRE# 01328224. Over 23 years in Silicon Valley real estate.
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