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

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

Welcome to the enchanting region of Yucaipa, Calimesa, and Oak Glen, nestled in the heart of Southern California’s San Bernardino County. This picturesque area is renowned for its stunning landscapes, featuring rolling hills, lush orchards, and breathtaking mountain views that create a serene backdrop for everyday living.

Yucaipa, with its charming small-town atmosphere, offers a delightful mix of modern amenities and rich history. Explore its vibrant downtown, where local boutiques and eateries invite you to experience the community’s warm hospitality. Just a stone's throw away, Calimesa boasts a tranquil vibe, perfect for those seeking a quieter lifestyle while still enjoying easy access to urban conveniences.

Oak Glen is a hidden gem famous for its apple orchards and seasonal festivals, making it a favorite destination for families and nature enthusiasts alike. This area is a haven for outdoor lovers, with numerous hiking trails, parks, and scenic picnic spots that showcase the breathtaking beauty of the San Bernardino Mountains.

For those seeking a home with a view, the properties in Yucaipa, Calimesa, and Oak Glen are truly captivating. Many homes here feature stunning hilltop vistas, allowing residents to enjoy panoramic views of the surrounding landscape right from their own backyard. Imagine sipping your morning coffee while soaking in the sunrise over the hills or hosting a sunset gathering with friends against a backdrop of rolling greens.

Whether you’re looking for a cozy cottage or a spacious family home, this region offers a variety of real estate options that cater to diverse lifestyles. Discover the charm of Yucaipa, Calimesa, and Oak Glen, where breathtaking views and a welcoming community await you!

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

$689,000
4 Beds ⋅ 3 Baths ⋅ IG26202594 MLS ⋅ Active Status
Welcome Home! If you are looking for an immaculate, impeccably maintained home in vibrant Yucaipa, look no further. This one is truly move-in ready! Step inside to find generous living spaces filled with natural light, soaring ceilings, and newer flooring that flows seamlessly throughout. The heart of the home is the spectacular chef’s kitchen, fully remodeled in 2025 featuring contemporary wood cabinetry, premium high-end appliances, and an expansive center island perfect for gathering and entertaining. This spacious layout offers 4 bedrooms, 2.5 baths, plus a dedicated first-floor workout room or office space to suit your lifestyle needs. Enjoy peace of mind knowing the property has been recently painted inside and out, with major big-ticket updates already taken care of including a new HVAC system installed in 2025 and a new water heater replaced in 2026. Unwind in your private backyard sanctuary while taking in scenic views of the surrounding hills. This move-in-ready gem truly combines luxury, comfort, and exceptional care! Situated in the neighborhood of upper Chapman Heights, you are close to parks, hiking, recreation areas, golfing, apple picking and the popular Uptown Yucaipa business district.

34532 Fawn Ridge Place, Yucaipa
$699,900
4 Beds ⋅ 3 Baths ⋅ PW26203129 MLS ⋅ Coming Soon Status
Professional photos will be added 9/17 - Beautiful Chapman Heights 2200+ sq/ft pool home on a large 8,844 sq ft lot located on a quiet cul-de-sac! This 4-bedroom, 3-bath home features a bright, open floor plan with soaring ceilings, plenty of natural light and newer paint throughout. The kitchen and family room with fireplace overlook the private backyard featuring a covered patio, sparkling pool and spa—perfect for entertaining. Downstairs offers a bedroom and full bath with walk-in shower, ideal for guests or extended family. Upstairs you’ll find three additional bedrooms, two baths and a spacious loft perfect for an office, game room or second living area. The primary suite features a private balcony overlooking the backyard with beautiful sunrise views. Large 3-car garage, leased solar and plenty of storage complete this great Chapman Heights home!

34354 Sherwood, Yucaipa
$575,000
3 Beds ⋅ 2 Baths ⋅ IG26202619 MLS ⋅ Active Status
Charming Single-Story Home in Upper Yucaipa! Welcome to this beautifully maintained single-story home offering nearly 1,500 square feet of comfortable living space in a well-established Upper Yucaipa neighborhood. This 3-bedroom, 2-bathroom home is move-in ready and full of thoughtful touches throughout. Step inside to a beautiful living room featuring a cozy fireplace and large windows overlooking the front yard, filling the space with natural light. The open dining area flows seamlessly into the kitchen, which boasts ample cabinetry space, a convenient center island, and a charming garden window with views of the side yard—perfect for both everyday living and entertaining. The spacious primary suite is a true retreat, complete with two walk-in closets, dual sinks, and windows overlooking the backyard. The home has been freshly painted throughout the interior and features brand-new carpet, offering a clean, modern feel from the moment you walk in. An upgraded HVAC system provides added comfort and efficiency year-round. A two-car garage and extra-wide driveway offer plenty of parking and storage space. Situated on a generously sized lot with plenty of room to enjoy, this home is centrally located near shopping centers, schools, restaurants, and everything Yucaipa has to offer. Don't miss this fantastic opportunity in a highly desirable location! **Scroll down under features to checkout the video tour!**

11810 Avalon, Yucaipa
$665,000
5 Beds ⋅ 3 Baths ⋅ IG26201885 MLS ⋅ Active Status
11525 Deerfield Drive, Yucaipa, CA — Upper Yucaipa's Chapman Heights Welcome home to this stunning 2,700-square-foot residence nestled in the highly sought-after Upper Yucaipa community of Chapman Heights. Situated on a generously sized lot, this five-bedroom, three-bathroom home offers the perfect blend of space, style, and functionality for today's buyer. Step inside to a bright, open living room that flows seamlessly into the kitchen and secondary dining area — ideal for everyday living and entertaining alike. The kitchen is a showstopper, featuring rich wood cabinetry, elegant granite countertops, stainless steel appliances, and sliding glass doors that open to the backyard for effortless indoor-outdoor living. A formal dining room adds an extra touch of sophistication for hosting family and friends. Downstairs, you'll find a spacious guest bedroom complete with its own cozy fireplace — perfect as a private retreat, guest suite, or a stylish home office. Upstairs, three additional guest bedrooms and a full guest bathroom provide plenty of room for family or visitors. The primary suite is a true sanctuary, boasting a walk-in closet, dual sinks, a soaking tub, a walk-in shower, and private access to an upper deck showcasing breathtaking city views. Additional highlights include a three-car tandem garage, tile roof, upgraded water heater, central heating and air conditioning, upgraded carpeting, tile flooring, beautiful landscaping, and a large driveway offering ample parking. Don't miss your chance to own this exceptional home in one of Yucaipa's most desirable neighborhoods — schedule your private tour of 11525 Deerfield Drive today!

11525 Deerfield, Yucaipa
$599,000
3 Beds ⋅ 2 Baths ⋅ IG26201825 MLS ⋅ Active Status
STOP SCROLLING—THIS NORTH BENCH BEAUTY HAS THE LOCATION, THE UPGRADES, AND THE MOUNTAIN VIEWS! Mountain views, beautiful upgrades, and a prime North Bench location come together at 10960 Larkspur Ln.! Tucked away on a quiet cul-de-sac and situated on a desirable corner lot, this beautifully maintained home offers over 1,700 square feet of living space with 3 bedrooms, 2 bathrooms, and a comfortable, inviting floor plan. Step inside to a bright interior featuring a neutral color palette, tile flooring, carpeting, and two separate living spaces. The updated kitchen is a standout with crisp white cabinetry, quartz countertops, stainless steel appliances, and a clean, timeless design. A formal living room welcomes you into the home, while the spacious rear living room features a cozy fireplace and plenty of room for relaxing or entertaining. Outside, enjoy a covered patio and backyard with beautiful mountain views, creating a great setting for outdoor dining or simply taking in the scenery. Vinyl fencing provides a clean, finished look, while charming brick steps leading to the front entry add to the home's curb appeal. Additional features include a tile roof and central heating and air. Located on Yucaipa's highly desirable North Bench, near local elementary and middle schools, this home offers a hard-to-find combination of location, upgrades, views, and a cul-de-sac setting. Beautifully cared for and ready for its next chapter, 10960 Larkspur Ln. is one you won't want to miss! **Scroll down under features to checkout the video tour!**

10960 Larkspur, Yucaipa
$1,890,000
IV26200715 MLS ⋅ Active Status
DEVELOPER'S DREAM — RARE YUCAIPA LAND ASSEMBLAGE | 7+ Acres | 70+ SFRs or 100+ Apartments! The market is moving and this is your window — four contiguous parcels totaling approximately 7 acres in booming Yucaipa, California. Four lots combined primed for large-scale residential development. Anchor parcel APN 0301-101-18 offers 3.85 acres zoned RM-10 joined by three RS-10 lots (Lots B, C & D — APNs 0301-111-24, 25 & 26) at 1.1 acres each. Blended pricing well under $337k per acre for higher density 3.85 acre lot. The adjoining 1.1 acre lots priced to sell at $200k each. Major development coming to the area validating demand in this very corridor. A potential fifth parcel at 12419 13th Street brings existing sewer infrastructure to the table — eliminating one of the biggest cost and timeline hurdles in raw land development. With city-confirmed lot merger eligibility, flexible density zoning, infrastructure in place, and a motivated direct seller ready to move. This assemblage checks every box a serious developer is looking for. Opportunities like this don't wait. Conceptual designs in supplements.

32797 Avenue D, Yucaipa
$1,199,999
5 Beds ⋅ 4 Baths ⋅ IG26200238 MLS ⋅ Active Status
Mountain views. Poolside sunsets. Dinner by the fire. Weekends in Oak Glen just up the road. This is Hidden Meadows living. Tucked into one of Yucaipa’s most sought-after neighborhoods, this beautifully remodeled single-story home pairs nearly 3,000 square feet of flexible living space with dramatic architecture, sweeping foothill views, and a backyard designed for year-round entertaining. Soaring vaulted ceilings, skylights, and walls of windows flood the main living spaces with natural light while framing the surrounding foothills. A sunken formal living room and adjoining dining space are anchored by two dramatic raised-hearth tiled fireplaces, while a built-in wet bar creates a natural gathering point. Expansive glass doors blur the line between indoors and out, opening the living spaces to the pool deck and surrounding views. The modernized kitchen combines two-tone cabinetry, stone countertops, breakfast bar, abundant storage, and an oversized walk-in pantry, with an easy flow between indoor and outdoor gathering spaces. The single-story layout offers five bedrooms and four bathrooms, highlighted by an impressive primary retreat with a generous sitting area and direct backyard access. Its remodeled en suite bath feels like a private spa, with a freestanding soaking tub, oversized glass shower, dual vanity, and serene finishes. On the opposite side of the home, a separate bedroom and adjacent bath beyond the kitchen create a flexible setup for guests, extended family, a private office, or multigenerational living. And then there’s the backyard: an expansive pool deck wraps around a sparkling pool and raised spa, with multiple places to lounge, dine, gather, and take in the mountain views. A covered outdoor kitchen and built-in seating make outdoor meals easy, while the oversized deck leaves plenty of room for quiet evenings or full-scale summer pool parties. Beyond the pool, low-maintenance turf, garden space, a chicken coop and small-animal enclosures bring a little of Yucaipa’s semi-rural character home, while a dedicated RV or boat parking pad adds hard-to-find flexibility. And when it’s time to leave home, the orchards, trails, restaurants, cider, and seasonal traditions of Oak Glen are just minutes up the road — close enough to make apple picking, mountain hikes, and cool fall afternoons part of an ordinary weekend.

13582 Oak Hill Court, Yucaipa
$130,000
2 Beds ⋅ 2 Baths ⋅ CV26198058 MLS ⋅ Active Status
2 Bed | 2 Bath | 55+ Community Light, space, and room to make it yours. This 2-bedroom, 2-bath home features an open kitchen overlooking the dining area and windows that keep things bright all day. The spacious side yard includes a shed — a nice bonus for storage or a weekend project. Life in this 55+ community means a pool and indoor spa, a clubhouse with billiards and a game room, a sauna, shuffleboard, a library, and RV storage. Golf is less than a mile away. Shopping and restaurants along Calimesa Boulevard are close by, and I-10 access makes commuting and weekend getaways easy.

10320 Calimesa Boulevard Unit 260, Calimesa
$450,000
3 Beds ⋅ 3 Baths ⋅ IG26198062 MLS ⋅ Active Status
HUGE INVESTOR OPPORTUNITY OR THE PERFECT CHANCE TO CREATE EQUITY! Sitting on a massive lot with incredible potential, this Yucaipa property is packed with possibilities for the buyer with vision. Whether you're looking for a renovation project, additional living space, possible ADU potential, rental income opportunities or simply room to create your dream property, there is so much to work with here. The main home features 2 permitted bedrooms and 1 bathroom, a family room with a brick fireplace, kitchen and indoor laundry, plus a huge additional bedroom with its own bathroom and walk-in closet. Even more opportunity awaits outside! The property offers pull-through access on BOTH sides of the home, leading to an expansive backyard with a detached 2 car garage, RV pad, large garden area, tons of storage and an abundance of open space ready to be transformed. There is also a detached unit with a room and bathroom, creating even more possibilities for flexible use. With its oversized lot, multiple structures, extensive access and room to reimagine nearly every corner, this is the kind of property where the possibilities truly are endless. Bring your vision, your tools and your creativity and unlock the potential of this Yucaipa gem! Buyer to verify permits, square footage, ADU possibilities, rental potential and intended uses.

11651 Vista, Yucaipa
$1,050,000
4 Beds ⋅ 4 Baths ⋅ IG26195990 MLS ⋅ Active Status
Nestled in the highly desirable Hidden Meadows neighborhood of Yucaipa, this stunning custom single-story residence offers space, quality, and thoughtful design throughout. Situated on over half an acre, the property features 4 bedrooms, 2 full bathrooms and 2 half bathrooms (One half bath located in the garage), and approximately 2,819 square feet of living space. The spacious floor plan includes a formal living room, formal dining room, and an expansive family room ideal for both everyday living and entertaining. The large kitchen is appointed with a center island, stainless steel appliances, custom white cabinetry, recessed lighting, and a picture window looking out to the backyard. The primary suite offers a private retreat complete with a fireplace and seating area. The upgraded primary bathroom features dual vanities, a soaking tub, and a large walk-in shower with windows providing natural light and backyard views. Interior finishes include custom tile work, laminate wood flooring, large baseboards, and window shutters. Outdoor amenities include a full-length covered patio across the rear of the home, a detached patio area with fireplace, an additional detached gazebo, mature landscaping, block walls, and wrought-iron fencing. Car enthusiasts and hobbyists will appreciate the oversized garage offering approximately 1,440 square feet of space, providing exceptional parking, workshop potential, and storage capacity. Plus the RV parking behind the wrought iron gate! A rare opportunity to own a spacious custom home on a large lot in one of Yucaipa’s most sought-after communities. Don't wait, this one isn't expected to last long!

37420 Wildwood View, Yucaipa
$549,900
2 Beds ⋅ 1 Baths ⋅ IG26194714 MLS ⋅ Coming Soon Status
A large, versatile bonus room with a built-in fireplace steals the spotlight in this darling ranch-style home. With 2 bedrooms, 1 bathroom, generously sized rooms throughout, and a spacious kitchen, this home offers plenty of room to live, work, and grow. Beautiful landscaping and a gated yard provide privacy and curb appeal, while the backyard offers low-maintenance turf, a shed, and plenty of room to make it your own. The 2-car garage offers plenty of cabinetry, a workshop bench, and overhead storage. A large, fenced RV parking adds even more versatility. Ideally located near Uptown Yucaipa—close to everything, yet tucked away from the hustle and parking challenges. A wonderful home for any season of life! Additional photos to come.

12001 2nd Street, 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
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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.