Yucaipa/Calimesa/Oak Glen (269) Homes with Canyon View

Welcome to the enchanting region of Yucaipa, Calimesa, and Oak Glen, where the beauty of Southern California meets serene, suburban living. Nestled in the San Bernardino Mountains, this picturesque area is renowned for its stunning canyon views, rolling hills, and a vibrant community that feels like home.

Yucaipa is celebrated for its charming downtown area, featuring unique shops, delightful eateries, and a welcoming atmosphere. The city boasts a rich history, with numerous parks and recreational facilities, making it an ideal location for families and outdoor enthusiasts. Just a stone's throw away, Calimesa offers a quieter suburban vibe, complemented by its beautiful golf courses and scenic landscapes. Oak Glen, known for its apple orchards and breathtaking natural surroundings, provides a perfect escape for those seeking a connection with nature.

For homebuyers looking for properties with breathtaking canyon views, this region has an array of options. Imagine waking up to the soft glow of sunrise illuminating the canyon, or enjoying evening sunsets that paint the sky in hues of orange and pink. Homes in Yucaipa, Calimesa, and Oak Glen often feature expansive windows and outdoor spaces designed to take advantage of the stunning vistas. Whether you’re seeking a cozy cottage or a sprawling estate, you’ll find properties that cater to diverse tastes and lifestyles.

Discover the magic of Yucaipa, Calimesa, and Oak Glen, where every day feels like a retreat. Experience the warmth of a close-knit community, the beauty of nature, and the joy of calling this remarkable region home. Your dream home with a canyon view awaits!

Newest Yucaipa/Calimesa/Oak Glen (269) Homes with Canyon View

$894,000

5 Beds ⋅ 3 Baths ⋅ IV26204970 MLS ⋅ Active Under Contract Status

Sharon Way — Ranch Living Near Wildwood Park, Yucaipa RARE PROPERTY ALERT!! — An extraordinary ranch opportunity in Yucaipa that truly doesn’t come around often. If you’ve dreamed of planting your own orchard, cultivating a vineyard, raising horses, goats, and chickens, or even running a business, steps from your front door with coffee in hand, this property delivers the space and freedom to make it real. Set on 3.5 acres of usable land, this ranch is paired with a beautifully updated 3,000 sq ft single story home overlooking your own private canyon. The acreage is a blank canvas ready for your vision — agricultural, equestrian, recreational, or entrepreneurial. A bounty of mature fruit trees already thrives here, including Lime, Lemon (two varieties), Orange, Grapefruit, Pomegranate, Plum, Apple, Peach, Asian Pear, Fig, and Grapes. A major 2022 renovation and expansion added a stunning new primary suite, spa style bathroom, and a multipurpose room with canyon views (easily convertible to a 5th bedroom). Additional upgrades include a new roof, new HVAC, new windows, and beautifully refreshed kitchen and bathroom spaces. Four bedrooms are conveniently located on one level, offering true single story ranch living. The location is exceptional — just a short walk, bike ride, or horseback ride to Wildwood Canyon State Park, and minutes from Oak Glen, Bogart Regional Park, Yucaipa Regional Park, Old Town Yucaipa, and the 10 freeway for commuters. Major employment centers in Loma Linda and Redlands are within easy reach. Wildwood Elementary School is also a quick and convenient walk from your front door. This is more than a home — it’s a lifestyle, a legacy property, and a rare chance to own acreage in one of Yucaipa’s most desirable ranch corridors. **Please note that the house has been virtually staged in the photos**

36098 Sharon, Yucaipa

$599,900

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

$1,249,000

5 Beds ⋅ 4 Baths ⋅ CV26189602 MLS ⋅ Active Status

37191 Wildwood View, Yucaipa

$550,000

IG26177600 MLS ⋅ Active Status

Pristine 42-Acre Panoramic View Property in Oak Glen’s Premier Agricultural & Winery Region Imagine owning 42 sun-drenched acres with breathtaking 360-degree vistas—a panoramic masterpiece set on a coveted Southwest-facing slope ideal for premium viticulture, boutique agriculture, luxury living, or visionary development. Rich, fertile soil makes this property a standout for vineyards, orchards, or specialty crops. With established commercial vineyards and agricultural operations flourishing nearby, Oak Glen has become a sanctuary for discerning growers, vintners, and entrepreneurs looking to craft their own success in one of Southern California’s most naturally beautiful and productive regions. Positioned between two major municipal wells and conveniently close to electric utilities, the land offers both natural advantages and essential infrastructure. Its expansive size and topography also allow for potential splitting, unlocking multiple development paths—boutique agricultural parcels, investment holdings, or a multi-estate layout designed to maximize views and privacy. For those dreaming of a custom residence, this property provides an extraordinary canvas. The elevated terrain and sweeping vistas create the perfect setting for a luxury dream home, a mountain estate compound, or a private retreat surrounded by nature, open sky, and unmatched tranquility. Developers will appreciate the flexibility to design high-end homes, agri-tourism experiences, or destination-style vineyard estates that complement Oak Glen’s growing prestige. Oak Glen’s rural charm continues to draw visitors and connoisseurs with farm-to-table experiences, boutique inns, seasonal festivals, and an expansive trail system that winds through the breathtaking mountain landscape. Thoughtful local development policies preserve sensitive habitat areas, further enhancing the natural beauty and long-term value of this unique region. A rare offering—42 acres of panoramic beauty, fertile soil, Oak Glen prestige, and limitless potential for agriculture, luxury living, or visionary development.

12100 Pisgah Peak, Yucaipa

$1,089,000

4 Beds ⋅ 3 Baths ⋅ IG26169038 MLS ⋅ Active Status

Tucked among beautiful mature trees and lush landscaping, this spacious single-story home offers privacy, flexibility, and incredible indoor-outdoor living just minutes from Oak Glen. The home features generously sized rooms, abundant storage, and a versatile bonus living area with its own bar, bedroom, bathroom, and additional space—ideal for extended family, guests, a mother-in-law suite, game room, or entertaining area. Step outside and enjoy a backyard that truly feels like a private retreat. The sparkling pool, dedicated BBQ area, outdoor chimney, and breathtaking views create the perfect setting for relaxing or entertaining. A sunroom provides a peaceful place to enjoy the sunrise, while the full-size tennis court offers recreation right at home. Additional highlights include multiple storage buildings, a three-car garage, RV parking, and plenty of room for all your hobbies, vehicles, and equipment. With its secluded setting, impressive amenities, and convenient location, this one-of-a-kind property offers space, comfort, and endless possibilities.

36268 Highland Ave, Yucaipa

$916,000

5 Beds ⋅ 5 Baths ⋅ CV26164138 MLS ⋅ Active Status

Perched atop one of the most desirable view lots in the exclusive gated community of Oak Hills, this extraordinary custom-built estate delivers an unparalleled combination of luxury, privacy, and breathtaking panoramic views stretching across the valley, city lights, and surrounding mountains. Set on approximately 4.56 acres, this impressive residence offers over 4,100 square feet of thoughtfully designed living space with 5 bedrooms and 5 bathrooms, including a private guest suite with its own entrance—ideal for multi-generational living, extended family, or long-term guests. From the moment you step through the grand double-door entry, soaring ceilings, abundant natural light, and expansive picture windows showcase the home's spectacular setting. The open-concept layout is designed for effortless entertaining, while the gourmet kitchen features granite countertops, generous workspace, and seamless flow into the main living and dining areas. The luxurious primary suite is a private retreat complete with a spa-inspired bathroom and stunning views, while an additional upstairs primary suite provides exceptional flexibility. Several bedrooms offer walk-in closets and private balconies where you can enjoy unforgettable sunrises, sunsets, and sparkling evening city lights. Step outside and experience true Southern California resort-style living. With acres of usable land, the possibilities are endless—create your dream pool, build an ADU, add a workshop, design an equestrian retreat, vineyard, or simply enjoy the unmatched peace and privacy that only a property of this caliber can provide. Additional highlights include a 4-car attached garage, gated driveway, mature landscaping, and ample parking for guests, and recreational vehicles. Rarely does a property combine luxury, acreage, breathtaking views, and endless potential in one exceptional offering. Conveniently located just minutes from I-10, shopping, dining, golf courses, and Yucaipa Regional Park, this is more than a home—it's a lifestyle destination

37550 Marondi, Calimesa

$999,000

5 Beds ⋅ 3 Baths ⋅ 219150163DA MLS ⋅ Active Status

Welcome to 13435 Canyon Crest Road, a beautifully updated estate offering over 3,200 square feet of living space with 5 bedrooms, 3 bathrooms. Nestled behind a private driveway, this exceptional property combines spacious living, thoughtful upgrades, and incredible indoor-outdoor entertaining.Step inside to discover an inviting formal living and dining room featuring elegant travertine flooring, custom finishes, and freshly painted interiors. The gourmet kitchen has been refreshed with professionally painted cabinetry, granite countertops, abundant storage, and opens seamlessly to the spacious family room--creating the perfect setting for everyday living and entertaining. Adjacent to the kitchen is a dedicated office or library complete with custom built-in cabinetry.The main level also features an oversized laundry room, a full bathroom, and a guest bedroom, ideal for visitors or multigenerational living.Upstairs, an open staircase leads to a versatile loft, perfect as a media room, game room, or additional office space. The expansive primary suite offers a private balcony, creating the perfect place to enjoy your morning coffee or evening sunsets. The luxurious primary bathroom has been beautifully remodeled with a newly designed walk-in shower, while three additional generously sized bedrooms provide plenty of space for family and guests.The outdoor living spaces are truly exceptional. The backyard has been extensively enhanced with newly upgraded landscaping, creating a private resort-like setting. The sparkling pool has been completely refinished with premium PebbleTec, providing lasting beauty and durability. Multiple entertaining areas include a covered patio, an impressive oversized spa accommodating approximately 15 people, and abundant space for hosting gatherings of any size.Additional improvements include fresh interior and exterior paint, updated landscaping, refinished pool, remodeled primary shower, and refreshed kitchen cabinetry. Completing the property is an oversized three-car garage and ample outdoor space rarely found in today's market.This remarkable home offers the perfect blend of luxury, comfort, privacy, and resort-style living--all in one exceptional property.

13435 Canyon Crest Road, Yucaipa

$650,000

4 Beds ⋅ 3 Baths ⋅ IG26139694 MLS ⋅ Active Status

AGENTS...This Home offers the buyer the opportunity to assume a 2.5% FHA Loan. Welcome to 264 Tanglewood Drive to an immaculate and move in ready beautiful home in JP Ranch. This home provides refined living in the prestigious gated community of JP Ranch in scenic Calimesa surrounded by breathtaking mountain views. Residents of JP Ranch enjoy a gated community with Club House, Pool, Spa, BBQ Area, Playground and much more. This exceptional home offers the perfect blend of elegance, functionality and location. From the moment you enter the home you feel impressed by its informal wide entry way and the spaciousness which welcomes you The home features 4 bedrooms and 3 full bathrooms. The thoughtfully designed floorpan includes 1 down stairs bedroom with full bathroom ideal for guests, multigenerational living or a home office setup. The layout flows naturally from the main living area into the kitchen which highlights granite counter tops, an island with raised breakfast bar, stainless appliances, ample white cabinetry and counter space along with a pantry. There is upgraded laminate flooring in the living areas downstairs, tile in all the bathrooms and laundry room with carpet in the bedrooms. From the kitchen area as you step outside the slider you notice the beautiful mountains and hills surrounding JP Ranch. There is a full size patio and alumawood raised patio cover for your enjoyment and comfort. The patio includes 3 specially selected fans for your relaxation. As you proceed upstairs you enter the oversized loft/great room which offers plenty of outside lighting and views. The primary suite is generously sized and features magnificent views of the mountains from the windows. The upgraded master bathroom features a walk in shower, dual vanities, and a walk in closet. There are two additional bedrooms upstairs offering privacy for everyone. The Laundry is off the loft/great room and includes a washer and dryer already hooked up and ready to go. As a bonus there is an additional room for storage off of the laundry room. The front and backyards were designed for minimal maintenance so you can spend time enjoying the home. The irrigation system is on a timer as an added feature. Do not miss this opportunity to secure one of the best values in JP Ranch.

264 Tanglewood Drive, Calimesa

$849,900

4 Beds ⋅ 3 Baths ⋅ IG26122820 MLS ⋅ Active Status

Welcome to 35102 Persimmon Ave in Upper North Yucaipa, where a distinctive single story floor plan delivers flexibility for a wide range of living arrangements. Offering 4 bedrooms, 3 bathrooms, and approximately 3,077 sq ft, this home features TWO private primary suites, each with its own bathroom, the main primary suite having two walk in closets. A versatile 4th bedroom, accessed directly through the main suite, serves as a flexible space that can adapt to your needs—as a private retreat, office, nursery, or a 4th bedroom. Set on an approximately 0.37 acre lot, the property provides gated RV parking on BOTH sides—one side with full hookups and the other with partial hookups. The expansive covered patio creates an inviting outdoor space to relax, entertain, and enjoy spectacular mountain and sunset views. Inside, the spacious great room centers around a fireplace, while the kitchen offers a gas cooktop, built in appliances, and a walk in pantry. Wide hallways, no interior thresholds, and a roll in shower enhance the home’s thoughtful single level design. The area just off the great room can function as a den, office, or indoor gym, complemented by built in laundry for added convenience. Additional highlights include a two car attached garage, zoned heating and cooling, a whole house fan, and no HOA. Located in desirable North Yucaipa near Oak Glen, regional parks, shopping, and dining. If you’ve been searching for generous single story living, two private bedroom suites, and substantial RV accommodations, this property deserves a closer look. Schedule your private showing and explore the possibilities at 35102 Persimmon.

35102 Persimmon, Yucaipa

$908,000

3 Beds ⋅ 3 Baths ⋅ IG26061656 MLS ⋅ Active Status

A RARE HILLSIDE RETREAT BACKING TO WILDWOOD CANYON where privacy, views, and design come together in a one-of-a-kind setting. This home offers unmatched privacy, breathtaking natural surroundings, and no rear neighbors. Enjoy daily encounters with nature, where deer, and native wildlife create a peaceful, ever-changing backdrop and experience. This upgraded home has undergone over $250,000 in improvements, blending modern comfort with custom upgrades. The inviting living room with expansive windows that frame breathtaking canyon views creates a stunning backdrop of natural beauty. Jaw dropping focal points are the floor to ceiling stone fireplace with thermostat control, and floating shelves with custom built-in storage with pull-out shelving. The updated kitchen was tastefully designed with blue cabinetry, iced with gold hardware, custom backsplash, and pull-out shelving. A stunning casual dining space wrapped in windows located in the kitchen, where every meal is accompanied by serene views, seamlessly bringing the beauty of the outdoors in. The circular formal dining room is a standout feature, surrounded by windows that capture the beauty of the outdoors from every angle with ample space for entertaining. Downstairs offers two guest bedrooms, and a full bathroom. As you enter the home from the garage, conveniently located is the indoor laundry room with ample storage, and an additional guest bath. Upstairs, the elevated loft style primary suite creates a semi-private retreat with unique touches including a pop-up TV hidden within custom cabinetry, city light views and additional space ideal for a lounge area. A spacious walk-in closet includes a walk-out attic for downstairs and pull-down attic access for upstairs. The updated primary bath features a vanity with dual sinks and a walk-in shower. Step outside to enjoy a landscaped backyard designed for relaxation and entertaining. While a large portion of the rear yard extends down the steep slope beyond the flat grassy area, the property provides stunning canyon views that enhances the sense of space, privacy, and connection to nature. The backyard fountain stays with the property and provides a relaxing setting as you enjoy the canyon views. Additional highlights include PAID SOLAR, an OWNED PROPANE TANK, NEWER HEAT PUMP with zones, a septic system, and an oversized 2-car garage. This is more than a home—it’s a private retreat with character and an unmatched setting.

13046 Oak Crest, Yucaipa

$267,500

IV24182348 MLS ⋅ Active Status

4.83 peaceful acres in San Bernardino County, elevation 4100ft with 270-degree endless sunset views. Community well with 7000-gallon buffer tank and fire hydrant riser. 15 minutes from Stater Bros, Zoned for SFR, Ideal for off-grid living in the Yucaipa Valley American Viticultural Area.

37342 Pisgah Peak Road, Yucaipa

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Based on information from California Regional Multiple Listing Service, Inc. as of . This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.