Oak Glen Real Estate

Oak Glen Real Estate

Welcome to Oak Glen, a picturesque gem nestled in the heart of San Bernardino County, California. Known for its stunning natural beauty and vibrant community spirit, Oak Glen offers a unique blend of rural charm and modern convenience, making it an ideal destination for families, retirees, and nature enthusiasts alike.

Surrounded by the majestic San Bernardino Mountains, Oak Glen is celebrated for its breathtaking landscapes, including rolling hills, lush orchards, and serene hiking trails. The area is particularly famous for its apple orchards, where visitors can indulge in seasonal apple picking and savor homemade cider and delicious pies. The crisp, clean air and stunning views create a perfect backdrop for outdoor activities, from hiking and biking to picnicking in one of the many scenic parks.

In addition to its natural allure, Oak Glen boasts a close-knit community with a rich cultural heritage. Local shops and restaurants offer a warm, welcoming atmosphere, where you can enjoy farm-to-table dining experiences and browse unique artisanal products. The annual events, such as harvest festivals and craft fairs, bring residents together, fostering a sense of belonging and community pride.

With its tranquil environment, excellent schools, and easy access to nearby urban amenities, Oak Glen is not just a place to live; it’s a lifestyle choice. Whether you’re seeking a peaceful retreat or an active community, Oak Glen invites you to discover all the charm and beauty it has to offer. Come explore this enchanting enclave and find your dream home in this idyllic California setting!

Newest Listings in Oak Glen

$1,000,000
OC26183814 MLS
DEVELOPMENT LAND The subject property includes two combined parcels totaling approximately 59.90 acres: • Mile-High Ranch Road: ±38.94 Acres • 13557 Mile-High Ranch Road: ±20.96 Acres

13557 Mile High Ranch, Oak Glen

Listing courtesy of Listing Agent: Nathan Holthouser (NATHAN@coastalcommercial.com) from Listing Office: COASTAL COMMERCIAL.
$3,870,000
3 Beds ⋅ 3 Baths ⋅ IG26080819 MLS
This 60-acre estate is a rare Southern California sanctuary where nature meets luxury. On scenic Oak Glen Road, gateway to Oak Glen, at 3,600 ft elevation, the property enjoys 4 distinct seasons, crisp mountain air, and a profound sense of peace, less than an hour from ONT. From the moment you pass through the gate, the outside world fades and a private, self-contained oasis-serene, secure, and breathtakingly beautiful unfolds. Varied terrain, mature trees, open skies, and abundant wildlife create a setting that feels worlds away yet fully connected to modern convenience. A 2,600 sq ft single-story ranch residence is designed for seamless indoor-outdoor living. Expansive windows frame views from every room—capturing sunrises, sunsets, and distant city lights. Stone and wood finishes complement an open, flowing layout, creating a refined yet relaxed living experience rooted in authenticity. Water is the defining luxury of this property. Two flowing creeks wind through the land, and beneath 2 bridges. A private half acre lake, stocked with fish and visited by migratory birds, is ideal for fishing, swimming, paddle recreation, or simply unwinding on the beach. Located within the Yucaipa Valley AVA, it offers potential for vineyards, winery, or a wedding venue. Ag amenities are in place, including a classic 24’x100’ four-stall barn with an attached bunkhouse with reclaimed barn doors, granite countertops, a sleeping loft, and full bath that provides guest or staff accommodation. Additional amenities: a 30’x100’ open pole barn, 30’x80’ hay barn, pipe and cable perimeter fencing, a 24’x70’ historic shop building with a storied past. and a 70-foot-round pen. Graded roads wind throughout the property, invite exploration by horseback, vehicle, or quiet walks through nature. 3 private water wells provide natural water for residential and ag use—an increasingly valuable asset. Ag Preserve zoning with Williamson Act benefits provides lower taxes, while the absence of HOA restrictions allows for flexibility, privacy, and control. With panoramic views in every direction and endless possibilities, this property offers a rare opportunity to create a true legacy estate, whether as a private retreat, multi-generational compound, working ranch, vineyard estate, or an inspired escape from the pace of city life. This is more than a property—it is a private world, a sanctuary of water and land, and one of Southern California’s most compelling opportunities.

37547 Oak Glen Road, Oak Glen

Listing courtesy of Listing Agent: Lavonne Webb (LaVonneCWebb@gmail.com) from Listing Office: RE/MAX ADVANTAGE.
$1,225,000
4 Beds ⋅ 3 Baths ⋅ IG26061388 MLS
Over two acres in Oak Glen with a single story 2013 build, an attached four car garage, stables, and a separate guest home.  Welcome to Snow Line Ranch! Located on a private street in the picturesque town of Oak Glen, this custom built home sits directly across from the protected Wildlands Conservancy. You approach the property and are greeted by stunning mountain views. This land was previously owned by Kevin Costner. Enter the home past the large front porch, or directly from the oversized four car garage (est. over 1200 sq ft) , which features even more storage space in a dedicated loft overhead. The great room in the center is the heart of the home.  A sizable living area features a rock wall with a wood burning stove. This opens up to a foyer, dining, and a large kitchen.  All of these rooms are filled with natural light from large double pane windows. High end touches included a conventional double oven, a walk in pantry, excellent counter space, and the farmhouse sink.  You may actually enjoy dishes with this view! The spacious primary suite is off of the kitchen, with it's own walk-in closet and a sizable bath.  There is a large shower and a soaking tub.  There are three additional bedrooms opposite the family room, all with sizable closet space.  One features French doors, and is currently in use as a home office. This home even has a basement (estimated at 432 square feet, and not included in the online square footage).  Heading outside, there is a 2023 Park Model manufactured home with two additional bedrooms, kitchen, living space, and even laundry hookups (estimated at 392 square feet, and not included in the online square footage). With it's own permanent water, power and septic hookups, this is perfect for a home office, guest space, or extended live-in family.  This private location on Raspberry means serene country living without the inconveniences of being too far off the grid.  We are only 15 minutes from Stater Brothers Market in Upper Yucaipa, and just around the corner from local Oak Glen dining. There is a paid solar system - owners total Edison power bill in 2025 was less that $100. Sellers use Starlink for internet. The Generac propane generator and the Oak Glen Domestic Water Company Shares are also included in the sale.

11821 Raspberry, Oak Glen

Listing courtesy of Listing Agent: JOSEPH SHAW (joseph@ritashaw.net) from Listing Office: Shaw Real Estate Brokers.
$1,850,000
IG26020916 MLS ⋅ Peddler's Pack BLDG.
These two commercial parcels totaling 4.2 acres are located across from the Oak Tree Mountain shops, in the heart of the quaint apple community of Oak Glen CA . The seasonal traffic pulls in high numbers and several eateries and ranches are now open year round for a consistent weekend customer. Formally known as the Peddlers Pack, the retail space has been known to many over the years as a place to purchase special treasures from all over the world. Situated on a beautiful knoll with big majestic trees and gated in/out entrance with a paved 16 car parking lot. The Retail space is approx. 980 sf with a handicap bathroom. The original homestead is situated nicely and was once partially used as additional retail space. The way the kitchen is situated it would make a nice eatery with large inside and out dining space. This original homestead has large open rooms at both ends with open beam ceilings and three separate front entrances. The front property entrance has covered stalls where alpacas where once raised and stalls in the back are currently used a chicken coop. There is nice storage building with electrical and also has three entrances. ( possible additional retail space.) A small cabin sits at the upper section of the parcel with open space for gathering around the firepit and log seating for presentations. This section of the property is 3 acres and has many uses. Retail, food, winery, orchard, vineyard, gardens, animal activities, camping, outdoor activities and many other options. The adjoining 1.2 acres has a modern built 2136 sf single story home with a loft. This lot has maintained it's commercial zoning with a small retail open shed for selling local goods. These two properties are currently being used as two homes, approx. 980 sf of retail space, a small cabin and out buildings. Oak Glen has long been the day trip, country getaway for the Los Angeles and Inland empire areas. The Oak Glen Botanical Gardens, Riley's Historical Reenactments, the many orchards and farms that offer hayrides, cider making and other family activities keeps "The Glen" full of excitement and fun. Bring your plans for a family business, an investment property or the idea that pulls at your heart strings and put the dream in motion.

39065 Oak Glen Road, Oak Glen

Listing courtesy of Listing Agent: Lavonne Webb (LaVonneCWebb@gmail.com) from Listing Office: RE/MAX ADVANTAGE.
$14,500,000
3 Beds ⋅ 5 Baths ⋅ 25615027 MLS
Step into a storybook setting... an extraordinary One-of-a-Kind Castle nestled in the beautiful mountain community of Oak Glen, California. This magical Estate is tucked away in a forest yet conveniently located, offering easy access and feeling worlds apart from the city. Just 11 minutes from Yucaipa, about an hour from Lake Arrowhead and only 90 minutes from Los Angeles, it's a rare find that blends convenience with absolute privacy. Designed as a true Castle showplace, the property features an impressive grand entertaining lounge... perfect to accommodate large gatherings, celebrations or quiet evenings in regal style. With its timeless design and beautiful natural setting, this remarkable property offers a rare blend of nostalgia, unique character and privacy. One of a Kind!! Oh, So Magical!! Attention Actors, Producers, and Writers... Your Dream Come True Property!!

38838 Birch Creek Lane, Oak Glen

Listing courtesy of Listing Agent: Lynne Wilson (lynne@lynneonthego.com) from Listing Office: Lynne B. Wilson & Associates.
$14,500,000
3 Beds ⋅ 5 Baths ⋅ IV25253989 MLS
Step into a storybook setting... an extraordinary One-of-a-Kind Castle nestled in the beautiful mountain community of Oak Glen California. This magical Estate is tucked away in a forest yet conveniently located, offering easy access and feeling worlds apart from the city. Just 11 minutes from Yucaipa, about an hour from Lake Arrowhead and only 90 minutes from Los Angeles, it is a rare find that blends convenience with absolute privacy. Designed as a true Castle showplace, the property features an impressive grand entertaining Lounge... perfect for large gatherings, celebrations, or quiet evenings in regal style. With its timeless design and beautiful natural setting, this remarkable property offers a rare blend of nostalgia, unique character, and privacy. One of a Kind! Oh So Magical!! Attention Actors, Producers, Writers...Your Dream Come True Property. Approximately 6.73 Acres.

38838 Birch Creek, Oak Glen

Listing courtesy of Listing Agent: LYNNE WILSON (lynne@lynneonthego.com) from Listing Office: LYNNE B WILSON & ASSOCIATES.
$1,850,000
4 Beds ⋅ 6 Baths ⋅ IG25201041 MLS
Nestled on a knoll across from the Oak Tree Mountain shops, in the heart of the quaint apple community of Oak Glen, you will find The Peddlers Pack. This is two multi use commercial zoned properties with two homes, retail space, out buildings, a guest cabin and an outside activity area all privately situated on 4.2 Acres. The sign at the road brings the happy tourists up a tree lined drive to a retail shop, or shops of approximately 980 ft.². The original 1923 Homestead has been updated and improved over the years but the charm and rustic character has been maintained. The layout boasts beautiful open beam ceilings, large living and family rooms, an open kitchen with commercial grade stove, two bedrooms and a big bonus room that is an easy additional bedroom. The character and charm of this home would tie in well as additional commercial space of 1685 ft.². This sale includes two parcels, the retail space and home on 3 acres with a large storage building and a guest cabin with a kitchenette and a three-quarter bath. Outdoor events can take place on the mostly level acreage with an encircling graded drive way. The adjoining 1.2 acre lot 39001 Harris Rd, has a 2136 sf home built in 1997. This home is single story with a loft, two bedrooms and an office, high ceilings and viewing decks. The combined 4.2 acreage is zoned commercial with residential use. This is a terrific spot for a business, a family compound or both. Each property has its own separate systems and both have their own well with holding tanks. This property is charming and private, yet in the heart of the Oak Glen tourist community. The opportunities are endless., Retail, outdoor venue, wine tasting, lodging and so much more. Oak Glen is rich in history, it enjoys four seasons, clean air and the mountain feel without the drive. Just 45 minutes to the Palm Springs International Airport and the Ontario International Airport. Bring your creativity and your entrepreneurial spirit and see what "The Glen has to offer."

39065 Oak Glen Road, Oak Glen

Listing courtesy of Listing Agent: Lavonne Webb (LaVonneCWebb@gmail.com) from Listing Office: RE/MAX ADVANTAGE.
$485,000
EV23119958 MLS
This 24 acre lot is located in one of the most highly sought after locations in Oak Glen. A gated entrance and tree lined country road leads to this hillside lot. The topography is sloping with several bench areas to build a spectacular home with an endless view. City lights, rolling hills and even Lake Perris seem close enough to touch. There is a share of water from a community well and a stone pillar and pipe fence on the property. Build your dream home, mountain retreat or seasonal home with easy access. Enjoy mountain wildlife, mild winter snow, the colorful four seasons and the convenience of well maintained access roads, with full lot frontage on Pine bench Road. The Oak Glen Fire burned the trees on this lot. The building areas are now easily viewed.

Pine Bench Road, Oak Glen

Listing courtesy of Listing Agent: Lavonne Webb (LaVonneCWebb@gmail.com) from Listing Office: RE/MAX ADVANTAGE.
$315,000
EV22227209 MLS
Price reduced!! Beautiful Oak Glen zoned OG/RL-5 property just under 10 Acres! This property is catercorner to National Forest land. It has several potential building sites on the property. Owner may carry with acceptable down payment. Check with San Bernardino County for possible uses.

Ivy, Oak Glen

Listing courtesy of Listing Agent: Benjamin Hartnell (BEN@YVRE.COM) from Listing Office: YUCAIPA VALLEY REAL ESTATE.
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