14 Chuckwagon Road, Rolling Hills: a remodeled ranch on 1.1 acres with stables turned ADU, sold over asking

Sold

Rolling Hills is bought by the acre and lived in by the room, and 14 Chuckwagon Road was priced for both. The house is a 1960 ranch of 3,061 square feet, remodeled through, on a fully usable 1.16 acre lot behind the city’s gates, with a pool, a motor court laid in Idaho schist, a kitchen built around a La Cornue range and two islands, and the property’s old stables converted into an accessory dwelling unit with a kitchenette and bath, the paddock turned into an outdoor lounge and the corral into raised garden beds, all with direct access to the Bowie Trail. We listed it at $3,899,000 in the spring of 2025 and closed at $3,950,000 on July 22, 28 days later, $51,000 over the asking price. The reason it cleared the ask is that the lot was usable.

What was the house?

A single-level ranch organized around the yard. The formal living room, with floor-to-ceiling bookcases and a fireplace, looks at the pool; the kitchen has custom cabinetry, the La Cornue range, a prep island and a seating island, and opens to a family room and dining area with built-ins for wine, coffee and the audio equipment. From the garage, sized for a car collector, a hall passes a fourth bedroom that served as an office or mudroom, a three-quarter bath and a large pantry on the way to the kitchen. The bedroom wing holds two en suite bedrooms with marble baths and garden views, a laundry room, and the primary suite with a stone fireplace, a walk-in closet and a spa-style bath. Central air and a backup generator were in place. Outside, the manicured grounds run to a distant Queen’s Necklace view, a stone path leads to the former stables, now an ADU, and the corral gardens sit at the trail.

What was the goal?

To sell a remodeled house in Rolling Hills to a buyer who would value the finish and the lot together, and to do it before the summer. The stakes in Rolling Hills are the acre: the city’s lots are large but many are hillside, and a flat, usable acre is the scarcest thing on the Peninsula; the risk for a seller is that a buyer prices the house as a house and misses the land. The strategy was to lead with the ground, the usable 1.16 acres, the trail access, the converted stables, the gardens, and to present the house as the finished way to live on it. The price of $3,899,000 was set at the top of the comparable range for remodeled single-level houses in the city, with the lot as the argument for it.

The sale closed at $3,950,000, 1.3 percent over the ask, on July 22, 2025, after 28 days. At $1,290 per square foot of house, or roughly $3.4 million per acre, the number reads correctly only when both are considered together, which is the point of a Rolling Hills price.

What does the sale say about Rolling Hills?

That usable land behind the gates commands a premium over the city’s hillside acreage that is larger than most owners expect, and that a finished house with the equestrian improvements converted to modern use, an ADU where the stables were, reaches buyers who would not have looked at a horse property and buyers who would. See Rolling Hills for the city and its association, Homes by Type for the Peninsula’s horse properties; the value of a converted outbuilding is a question we answer lot by lot.

Update: sold

If you own a usable acre in Rolling Hills, the land is the price and the house is the argument for it. Send Neil the address and we will tell you what the acre is worth against the last year of sales behind the gates. The Sellers page describes how we prepare a Rolling Hills listing.

Sources

• California Regional MLS listing record, SB25088872; closing figures as reported to the MLS
• Rolling Hills; Homes by Type

Written May 2025; updated July 22, 2025. Property facts, list price and days on market are from the California Regional MLS listing record (SB25088872); the sale price and closing date are public record. Represented by Neil Chhabria, Chhabria Real Estate Company. This article is general real estate information about one sale, not tax, legal, lending or investment advice, and not a statement about the value of any other property.

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