39922 Pine Bench RD Oak Glen CA 92399 | MLS #IG26194625
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.
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.
Property Details
Price:
$599,900
MLS #:
IG26194625
Status:
Active
Beds:
2
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
269yucaipacalimesaoakglen
Listed Date:
Sep 5, 2026
Finished Sq Ft:
925
Lot Size:
113,256 sqft / 2.60 acres (approx)
Year Built:
1946
See this Listing
Schools
School District:
Yucaipa/Calimesa Unified
Interior
Bathrooms
2 Full Bathrooms
Cooling
NO
Interior Features
OFP
Laundry Features
NO
Levels
A
Main Level Bathrooms
2
Main Level Bedrooms
2
Exterior
Common Walls
NCW
Community Features
URB
Direction Faces
NE
Fencing
NO
Other Structures
SHP, SBL, TL
Patio And Porch Features
CON
Security Features
AG
Spa Features
NO
View
CN, CI, HI, MT, PA, NE
Financial
HOA Fee
$400
HOA Fee Frequency
ANU
Map
Community
- Address39922 Pine Bench RD Oak Glen CA
- CityOak Glen
- CountySan Bernardino
- Zip Code92399
Market Summary
Current real estate data for Single Family in Oak Glen as of Sep 07, 2026
6
Single Family Listed
159
Avg DOM
2,939
Avg $ / SqFt
$6,168,317
Avg List Price
Property Summary
- 39922 Pine Bench RD Oak Glen CA is a Single Family for sale in Oak Glen, CA, 92399. It is listed for $599,900 and features 2 beds, 2 baths, and has approximately 925 square feet of living space, and was originally constructed in 1946. The current price per square foot is $649. The average price per square foot for Single Family listings in Oak Glen is $2,939. The average listing price for Single Family in Oak Glen is $6,168,317. To schedule a showing of MLS#ig26194625 at 39922 Pine Bench RD in Oak Glen, CA, contact your The Knight Group LA agent at 310.409.7242.
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Courtesy of COLDWELL BANKER KIVETT-TEETERS. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the California Regional Multiple Listing Service. Detailed information about real estate listings held by brokerage firms other than The Knight Group LA include the name of the listing broker. Neither the listing company nor The Knight Group LA shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. California Regional Multiple Listing Service. All rights reserved.39922 Pine Bench RD
Oak Glen, CA
