905 Charter Oak Avenue

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.

Days on Market

1 day

Current Status

Active

Original Price

$4,395,000

List Price

$4,395,000

On Market Date

Apr 7, 2026

Property Type

Single Family Residence

Area

St. Helena

Zip Code

94574

MLS ID

326021787

APN

009-112-013-000

Year Built

2006

Stories in Building

Unavailable

Possession

Close Of Escrow

Data Source

BAREIS

Origin MLS System

Bed

5

Bath

6 (4/2)

Double Sinks, Shower Stall(s), Stone, Tile, Walk-In Closet

Parking

6

Detached, EV Charging, Garage Door Opener, Garage Facing Front

SQ FT

3,290

SQ FT Source

Graphic Artist

Lot SQ FT

22,534.0

Lot Acres

0.5173 Acres

Pool Info

Built-In, Gas Heat, Pool Sweep, Pool/Spa Combo

Kitchen

Breakfast Area, Granite Counter, Island w/Sink, Pantry Cabinet

Cooling

Central

Dining Room

Formal Area

Living Room

Cathedral/Vaulted

Flooring

Tile, Wood

Foundation

Concrete Perimeter

Fire Place

Gas Log, Stone

Heating

Central, Fireplace(s)

Laundry

Cabinets, Dryer Included, Inside Room, Sink, Washer Included

Main Level

Bedroom(s), Dining Room, Full Bath(s), Kitchen, Living Room, Primary Bedroom, Partial Bath(s)

Views

Vineyard

Possession

Close Of Escrow

Basement

None

Architectural Style

Contemporary, Farmhouse

Fee

$0

MLS and other Information regarding properties for sale as shown in Theo have been obtained from various sources such as sellers, public records, agents and other third parties. This information may relate to the condition of the property, permitted or unpermitted uses, zoning, square footage, lot size/acreage or other matters affecting value or desirability. Unless otherwise indicated in writing, neither brokers, agents nor Theo have verified, or will verify, such information. If any such information is important to buyer in determining whether to buy, the price to pay or intended use of the property, buyer is urged to conduct their own investigation with qualified professionals, satisfy themselves with respect to that information, and to rely solely on the results of that investigation.

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