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$599,900

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.

2 Beds ⋅ 2 Baths ⋅ IG26194625 MLS ⋅ Active Status

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.

39922 Pine Bench Road, Oak Glen

$1,690,000

Tucked away on 3.5 acres of serene Oak Glen paradise, this private sanctuary offers a rare retreat where towering Cedar, Redwood, Oak, and Aspen trees embrace a home that masterfully bridges the gap between rugged mountain charm and contemporary sophistication. Accessed by a long, private gated driveway that promises total seclusion, the residence welcomes you with an awe-inspiring 31-foot-high ceiling, where rustic beams and an intricate Herringbone pattern create an unforgettable architectural statement. Inside, the home honors its unique heritage while incorporating thoughtful modern enhancements, including brand-new flooring, contemporary fixtures, updated baths, new roof, decks and stucco with attention to detail that elevates the comfort and design of its 3735 square feet of living space. At the heart of the home, a massive stone fireplace anchors the living area, creating an inviting gathering spot, while a wood stove on the main floor ensures cozy efficiency during chilly mountain evenings. Culinary enthusiasts will adore the European-style kitchen, complete with custom cabinetry, granite countertops, and top-tier appliances from Miele, Bosch, and Sub-Zero, all framed by a wall of windows that pulls the vibrant landscape inside. The lower level offers a sprawling 26x30 game room featuring its own entrance and a second floating hearth fireplace, providing the perfect venue for entertainment. The primary suite enjoys large windows for viewing, built-in storage and an updated bath with a new walk-in shower. Outside, wraparound viewing decks invite you to savor the breathtaking panoramas of city lights, tranquil meadows, and rugged mountains. Off the kitchen patio is a large detached room that could be a great office or gym. The garage has new epoxy flooring and a bath, along with a tall garage door. The covered entry parking is convenient for all seasons. Fruit trees dot the property, and the usable land invites you to bring your big ideas and future plans to live the good life in "The Glen."

3 Beds ⋅ 4 Baths ⋅ IG26189600 MLS ⋅ Active Status

Tucked away on 3.5 acres of serene Oak Glen paradise, this private sanctuary offers a rare retreat where towering Cedar, Redwood, Oak, and Aspen trees embrace a home that masterfully bridges the gap between rugged mountain charm and contemporary sophistication. Accessed by a long, private gated driveway that promises total seclusion, the residence welcomes you with an awe-inspiring 31-foot-high ceiling, where rustic beams and an intricate Herringbone pattern create an unforgettable architectural statement. Inside, the home honors its unique heritage while incorporating thoughtful modern enhancements, including brand-new flooring, contemporary fixtures, updated baths, new roof, decks and stucco with attention to detail that elevates the comfort and design of its 3735 square feet of living space. At the heart of the home, a massive stone fireplace anchors the living area, creating an inviting gathering spot, while a wood stove on the main floor ensures cozy efficiency during chilly mountain evenings. Culinary enthusiasts will adore the European-style kitchen, complete with custom cabinetry, granite countertops, and top-tier appliances from Miele, Bosch, and Sub-Zero, all framed by a wall of windows that pulls the vibrant landscape inside. The lower level offers a sprawling 26x30 game room featuring its own entrance and a second floating hearth fireplace, providing the perfect venue for entertainment. The primary suite enjoys large windows for viewing, built-in storage and an updated bath with a new walk-in shower. Outside, wraparound viewing decks invite you to savor the breathtaking panoramas of city lights, tranquil meadows, and rugged mountains. Off the kitchen patio is a large detached room that could be a great office or gym. The garage has new epoxy flooring and a bath, along with a tall garage door. The covered entry parking is convenient for all seasons. Fruit trees dot the property, and the usable land invites you to bring your big ideas and future plans to live the good life in "The Glen."

39155 Harris, Oak Glen

$3,870,000

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.

3 Beds ⋅ 3 Baths ⋅ IG26080819 MLS ⋅ Active Status

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

$485,000

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.

EV23119958 MLS ⋅ Active Status

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

$315,000

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.

EV22227209 MLS ⋅ Active Status

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