$1,290,000
39292 Oak Glen RD
Oak Glen, CA, 92399
This custom mountain style chalet sits privately amongst big Sycamore and Oak trees. The beautiful lawns and the large rock formations surround the home with a natural fenced meadow beyond. A gated front entrance with a long driveway and a full circle at the home entry and garage. A lower entrance provides access to the two RV garages and the shop. This home offers 3430 square feet, with four bedrooms and three bath, beautiful open beam cathedral, ceilings, large stone fireplace, natural wood accents and large windows to enjoy the beautiful surroundings. The primary suite and one other bedroom, which is currently being used as a game room, are both on the first level. The second level has two bedrooms and a full bath. The living spaces are large and open, warm and inviting. The rear deck goes the entire span of the house and is a very tranquil place to relax. The RV garages are approximately 40 foot and 32 foot deep. There is a guest cottage with a kitchen over one of the garages and an additional single garage workshop that stands alone. The deck and patios are beautifully designed with gardens and gathering areas that are easily accessible and are often enjoyed. This tranquil setting enjoys the four seasons, the slightly cooler temperatures and the mountain feel without the mountain drive. The 2 acres of land provides space for additional uses, orchard, vineyard, hobbies and more. Easy to enjoy this home and the possibilities of room to personalize the use of the land. More photos coming.
Property Details
Price:
$1,290,000
MLS #:
IG25257775
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
269yucaipacalimesaoakglen
Listed Date:
Nov 12, 2025
Finished Sq Ft:
3,430
Lot Size:
90,605 sqft / 2.08 acres (approx)
Year Built:
1977
Schools
School District:
Yucaipa/Calimesa Unified
High School:
Yucaipa
Interior
Appliances
DW, GD, MW, ES, EO, WHC
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
CA
Flooring
TILE, WOOD, CARP
Heating
CF
Laundry Features
ELC, IR
Exterior
Community Features
RUR, HIKI
Exterior Features
RG
Other Structures
GHD
Parking Spots
3
Roof
TLE
Financial
Get Out There, A Simply Outgoing Approach to Life. James Outland Jr. is one of those rare people who simply has an outgoing approach to life. No matter the activity… from dune buggy riding to skydiving to motorcycling to riding the local Pismo Beach waves… James Outland Jr. approaches life with a “just get out there and do it” kind of attitude. A zest for Life. James’ zest for life is obviously apparent in his many exciting hobbies. In his spare time, he loves riding dune buggies or hi…
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Map
Current real estate data for Single Family in Oak Glen as of Feb 14, 2026
5
Single Family Listed
95
Avg DOM
3,162
Avg $ / SqFt
$6,567,800
Avg List Price
Community
- Address39292 Oak Glen RD Oak Glen CA
- CityOak Glen
- CountySan Bernardino
- Zip Code92399
Similar Listings Nearby
Property Summary
- 39292 Oak Glen RD Oak Glen CA is a Single Family for sale in Oak Glen, CA, 92399. It is listed for $1,290,000 and features 4 beds, 4 baths, and has approximately 3,430 square feet of living space, and was originally constructed in 1977. The current price per square foot is $376. The average price per square foot for Single Family listings in Oak Glen is $3,162. The average listing price for Single Family in Oak Glen is $6,567,800. To schedule a showing of MLS#ig25257775 at 39292 Oak Glen RD in Oak Glen, CA, contact your James Outland agent at 8057482262.
Courtesy of RE/MAX ADVANTAGE. 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 James Outland include the name of the listing broker. Neither the listing company nor James Outland 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. 39292 Oak Glen RD
Oak Glen, CA


















































