905 Charter Oak Ave

St. Helena CA 94574

3290 sq. ft.

22534 sq. ft.

Single-Family

Last sold for $3,600,000

Joshua Dempsey, last sold this property on 21 July 2026 after 71 days on market.

Overview

A rare offering in the heart of St. Helena. An expansive .52-acre in-town property combining single-level living, a five-bedroom compound layout, and exceptional proximity to downtown. Located on one of St. Helena's most historic and picturesque streets, just moments from the town's renowned dining, tasting rooms, and shops, this thoughtfully rebuilt residence offers a rare blend of scale, privacy, and flexibility within the city limits. Set across a generous and uncommon parcel, the property features a three-bedroom, two-and-a-half-bath main residence designed for entirely single-level living, complemented by a fully detached two-bedroom, two-bath ADU and oversized 2-car garage. Originally rebuilt from the ground up in 2006, the home presents a classic Craftsman exterior that opens to a warm, design-forward interior. Vaulted wood-beamed ceilings, abundant natural light, and curated finishes create a sense of quiet sophistication throughout. The home has been thoughtfully refreshed under the direction of renowned interior designer Jay Jeffers, resulting in a refined and cohesive aesthetic throughout. The spacious kitchen anchors the home and flows seamlessly into inviting living and dining areas, while the primary suite and guest bedrooms offer comfort and separation. The grounds unfold into a private backyard retreat, where manicured garden spaces, several thriving citrus trees and multiple outdoor gathering areas create a setting that feels both expansive and intimate. A generous pool and spa serve as the focal point, complemented by a pool house and thoughtfully designed spaces for entertaining and relaxation. Private and serene, yet exceptionally close to the best of St. Helena, this is a rare opportunity to own a fully realized Napa Valley compound offering scale, versatility, and enduring appeal.

Features

5 bedrooms

6 bathrooms

6 carspaces

2 garage spaces

3290 sq. ft. floor area

22534 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in St. Helena over the last 12 months, the estimated median property value of 905 Charter Oak Ave is $7.1m.

Median value

$7.1m

Estimated value range

$2.3m - $18.5m

Median days on market

136

Estimated value trend

110%

increase over the last 12 months

Average days on market is based on recent, comparable sales in St. Helena. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 905 Charter Oak Ave

2026

Sold

$3,600,000

21 Jul 2026 by Joshua Dempsey, of Vanguard Properties

2018

Sold

$2,850,000

31 May 2018 by Tim Hayden

2017

Sold

$2,590,000

04 Dec 2017 by Joel Toller, of Coldwell Banker Brokers of the Valley - St. Helena

Happy sellers in St. Helena

We have insufficient information to provide an overview of customer satisfaction for St. Helena. Viewing the agent profiles, reviews and sales for St. Helena can provide insights for this location.