A private south-Pleasanton enclave of about a dozen custom homes on Romeo Court, on ¾-to-1-acre lots — with a one-of-a-kind history tracing back to the Studebakers and racehorse Man o' War.
Some of Pleasanton's most special places are also its smallest, and Heather Hill is a perfect example — a private enclave of just about a dozen custom homes on Romeo Court, tucked into the south side of town. With so few homes, it rarely comes to market, and even longtime Pleasanton residents sometimes confuse it with neighboring Carriage Gardens. But Heather Hill is very much its own place, with a history that's genuinely one of a kind.
This is one of my favorite Pleasanton backstories. The original twenty acres belonged to the Studebaker family and once operated as a horse-boarding stable — and as neighborhood lore has it, the legendary racehorse Man o' War once stayed on the property. In 1980, ten of those acres were sold to Dan and Donna Gamache, who subdivided the land into individual lots. The private court at the center took the name Romeo Court, after Dan's grandfather Romeo Gamache, and the subdivision itself was named Heather Hill for the Gamaches' daughter, Heather. The Spanish-style home crowning the top of the hill is still owned by the Gamache family today. It's the kind of provenance you simply don't find in a typical subdivision.
Heather Hill is a true custom-home neighborhood. The roughly dozen lots — generously sized at about three-quarters of an acre to a full acre each — were sold to individual owners who then built their own homes, so there's no repeating builder floor plan here. Every house is distinct, set on a large, private parcel with the room that acre-scale lots allow. Because the homes were built over time by different owners, they vary in age and architecture, and that's part of the appeal: this is a neighborhood of one-of-a-kind homes rather than a uniform tract. Add in the rarity — barely a dozen homes total — and it's easy to see why Heather Hill holds its character and its value.
Heather Hill enjoys one of the quiet advantages of south Pleasanton: the neighborhoods on this side of town sit in the lee of the Pleasanton Ridge, which means notably less wind than other parts of the valley. You're about a half-mile from the Callippe Preserve Golf Course and roughly a twenty-minute walk to the Oak Hill shopping center, with its Raley's, restaurants, and everyday errands close at hand. Downtown Pleasanton's dining and shopping are a short drive away, and you've got solid access to the commute routes when you need them. It's a setting that feels tucked-away and private while keeping the essentials within easy reach.
Heather Hill is served by the highly regarded Pleasanton Unified School District. Homes here have generally been associated with Phoebe Hearst Elementary, Pleasanton Middle School, and Foothill High School — but assignments in Pleasanton can come down to the specific parcel, so I always verify the designated elementary, middle, and high school for any individual home with PUSD before a client makes a decision.
A neighborhood of only about a dozen custom homes doesn't generate many sales in a given year, so when one does come up, it's an event — and the right buyer is usually someone who already knew to watch for it. Whether you're drawn to the privacy, the acre-scale lots, or simply the chance to own a piece of a neighborhood with this much character and history, I'd love to help you understand what's selling here and what it's worth.
Because Heather Hill is so small and so often confused with the neighborhoods around it, having someone who knows exactly where it begins and ends — and what makes it different — matters. That kind of street-level detail is where I can genuinely help.
— Rebecca Rook, Living Tri-Valley | Compass
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