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$6,495,888
4 Beds 4 Baths ML82059150 MLS
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.

5 Winding Oaks Drive, Pleasanton

Listing courtesy of Mona Lisa Weise from Compass. 408-221-0627

$2,469,000
4 Beds 4 Baths 41138914 MLS
Lined with beautifully preserved historic homes and mature trees, this coveted Downtown Pleasanton street embodies the charm and character that make the area so special. This 1934 historic home seamlessly blends timeless architecture with modern convenience. Its distinctive stone façade, steeply pitched roofline, and arched entry create a memorable first impression rarely found today. Inside, an open floor plan flows from the foyer through the kitchen into a sunlit family room with hardwood floors, arched doorways, and a gas fireplace. A built-in bar with exposed brick makes entertaining effortless, while an oversized sliding door opens directly to the backyard for seamless indoor-outdoor living. The kitchen features quartz counters, stainless steel appliances, gas cooktop, double oven, and a garden window. The first-floor primary suite offers a private bath and dedicated laundry just off the bedroom, while a junior suite upstairs adds flexibility. Out back, a fully covered outdoor living room with vaulted ceiling, stone fireplace, and ceiling fan creates a space that feels like an extension of the home itself. String lights and uplighting make it just as inviting after dark. A detached guest unit with exposed beam ceiling, en suite bath, and private entrance offers space for family, a home office, or income potential. Steps to a thriving restaurant scene, boutique shops, the Farmers Market, Concert in the Park, and everything this storied neighborhood has to offer. Come experience it for yourself.

4687 Second Street, Pleasanton

Listing courtesy of Gina Manos from GMC Properties. 925-200-0592

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