39922 Pine Bench Road, Oak Glen 92399

$599,900

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2

Beds

2

Baths

925

Square feet

113,256

Lot Size

Listing Agent
Tricia Wirth Gregory - COLDWELL BANKER KIVETT-TEETERS

About 39922 Pine Bench Road

A Rare Opportunity in the Heart of Majestic Oak Glen. Some properties simply give you a place to live. Others give you a story, a setting and possibilities that are difficult to recreate. Tucked away among the towering trees and natural beauty of Oak Glen, this extraordinary property offers approximately 2.6 acres and two uniquely charming units, creating an opportunity unlike almost anything else you will find in this treasured mountain community. From the moment you enter, there is a feeling that this property is special. Mature oak trees create a breathtaking canopy, the peaceful setting feels worlds away from the city below, and the two distinctive units blend naturally into their surroundings. Whether envisioned as a private family compound, multigenerational retreat, guest accommodations, artist's getaway, investment opportunity or something entirely different, the possibilities here are remarkable. And then there is the history. Oak Glen has been a special part of Southern California since the 1800s, known for its orchards, ranches, mountain landscape and generations of families who have worked to preserve its rural character. This property seems to capture that same spirit one-of-a-kind, rooted in the land and impossible to duplicate. Among its most fascinating features is an enormous heritage oak tree that the seller states has been identified as the largest oak tree in San Bernardino County, creating a natural centerpiece that must truly be experienced in person. Water is another extraordinary feature. The seller reports the private well is considered one of the strongest-producing wells in Oak Glen, an impressive feature for a mountain property and one buyers will certainly want to explore further. The property also offers a shared septic system, propane, additional storage and areas of usable land that invite you to imagine what could come next. There appears to be additional space toward the upper portion of the property that may offer future possibilities, subject of course to county requirements and buyer investigation. This isn't a property that can be fully appreciated by reading about it, you need to walk the land, hear the quiet, stand beneath the magnificent oak and experience Oak Glen for yourself. For the buyer looking for something truly different, this may be one of those rare properties that only comes along once.

Features of 39922 Pine Bench Road

MLS® # IG26194625
Price $599,900
Bedrooms 2
Bathrooms 2.00
Full Baths 2
Square Footage 925
Lot Size 113,256
Year Built 1946
Type Residential
Sub-Type Single Family Residence
Status Active
# Of Units 2

Community Information

Address 39922 Pine Bench Road
Area 269 - Yucaipa/Calimesa/Oak Glen
City Oak Glen
County San Bernardino
Zip Code 92399

Amenities

Amenities Security
Utilities Electricity Connected, Propane
View City Lights, Canyon, Hills, Mountain(s), Neighborhood, Panoramic
Is Waterfront No
Has Pool No
Pool None

Interior

Interior Features Open Floorplan, All Bedrooms Down, Workshop
Cooling None
Has Basement No
Fireplace Yes
Fireplaces Family Room, Wood Burning
# of Stories 1
Stories One

Exterior

Lot Description TwoToFiveUnitsAcre, Lot Over 40000 Sqft
Foundation Slab

School Information

District Yucaipa/Calimesa Unified

Additional Information

Date Listed September 3rd, 2026
Days on Market 5
Foreclosure No
Short Sale No
RE / Bank Owned No
HOA Fees 400
HOA Fees Freq. Annually

Listing Details

AgentTricia Wirth Gregory
OfficeCOLDWELL BANKER KIVETT-TEETERS

Listing Map

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