Yucaipa/Calimesa/Oak Glen (269) Homes with Multi Level Stories

Welcome to the enchanting region of Yucaipa, Calimesa, and Oak Glen, nestled in the heart of San Bernardino County, California. This picturesque area is a hidden gem known for its stunning landscapes, vibrant community, and a delightful blend of rural charm and modern conveniences. From the rolling hills of Oak Glen, famous for its apple orchards and breathtaking mountain views, to the quaint streets of Yucaipa and the serene atmosphere of Calimesa, this region offers a lifestyle that many dream of.

One of the standout features of homes in this area is the availability of multi-level story residences. These homes are not just structures; they are sanctuaries that provide ample space for families to grow and thrive. With thoughtful designs that maximize both functionality and aesthetic appeal, multi-level homes in Yucaipa, Calimesa, and Oak Glen often boast spacious living areas, stunning views, and private outdoor spaces perfect for entertaining or enjoying a peaceful evening.

Imagine waking up in a master suite on the upper level, sipping your morning coffee while gazing out at the majestic San Bernardino Mountains. The lower levels offer versatile spaces that can be transformed into home offices, guest suites, or cozy entertainment areas. Whether you are seeking a home with a sprawling layout or a quaint retreat, the multi-level homes in this region cater to a variety of lifestyles.

Discover the charm of Yucaipa, Calimesa, and Oak Glen, where breathtaking nature meets a vibrant community, and your dream home awaits!

Newest Yucaipa/Calimesa/Oak Glen (269) Homes with Multi Level Stories

$1,199,000

4 Beds ⋅ 2 Baths ⋅ IG26073154 MLS ⋅ Active Status

Endless possibilities! Two parcels, on Yucaipa’s north bench, totaling 3.55 acres, hold limitless opportunities. Located at approximately 2900 ft elevation, surrounded by mountains, the unique microclimate offers cooler summer temperatures with occasional light dusting of snow in winter months. The terrain gently slopes allowing access/use of the entire property yet is elevated from the street for privacy. The uniquely designed multilevel home features a private living space with its own entrance (at its lowest level.) The mid-level includes the formal living space, kitchen and generous family room complete with a wood burning stove. Ascend to the upper level and you’ll find three additional bedrooms with one common bath. All powered by PAID FOR SOLAR. Also onsite is An approximately 1,440 sf manufactured structure, perfect for a home-based office. And, lastly, the rustic barn…the kind you see amongst pastures during your road trips. Bring all your RVs and toys, plant a vineyard, or build additional structures/ADUs. The possibilities are endless! Learn more about the Yucaipa Valley American Viticultural Area in the supplements.

10207 Juniper Avenue, Yucaipa

$1,200,000

5 Beds ⋅ 5 Baths ⋅ IG26028228 MLS ⋅ Active Status

Welcome to an extraordinary hilltop Spanish-Mediterranean retreat with breathtaking mountain and city-light views. Privately positioned on 1.32 acres at the end of a quiet road shared by only four homes, this tri-level estate offers rare seclusion, panoramic scenery, and a lifestyle that feels like a permanent getaway. Spanning 4,371 square feet, the home features 5 bedrooms, 4.5 bathrooms, and a 4-car drive-through garage, thoughtfully designed for multi-generational living and memorable entertaining. From the moment you enter, soaring ceilings, floor-to-ceiling windows, imported wood accents, custom doors, and rich hardwood floors create warmth and timeless character. The dramatic living room showcases 20-foot ceilings, exposed wood beams, a striking stone fireplace, and an architectural catwalk that connects the living spaces while framing the incredible views. The main level also includes a den with built-in bar, formal dining room, spacious kitchen with island, guest bath, and mudroom/storage area—ideal for hosting with ease. This home offers two private primary suites, each with en-suite bathrooms and private balconies. One suite features a spa-inspired jetted tub perfectly positioned to soak in the scenery. The upper level includes a cozy lounge landing, two additional bedrooms, a full bathroom, a large laundry room, and an oversized bonus room currently used as a bedroom and game room. Newer windows and sliding doors open to multiple decks and patios, seamlessly blending indoor and outdoor living. Outside, enjoy a long private driveway, RV and boat parking, additional parking areas, solar power, a sand volleyball court, fruit trees including walnut, and a jacuzzi overlooking the hills—perfect for stargazing and unwinding at sunset. Conveniently located just minutes from Oak Glen’s apple orchards, vineyards, regional parks, and the shops and dining of uptown Yucaipa, yet feeling worlds away. No HOA. Offered fully furnished and ideal as a primary residence, second home, or potential vacation rental. Just 74 miles to Los Angeles and 41 miles to Palm Springs. A rare hilltop sanctuary—schedule your private showing today.

36435 Jomar Street, Yucaipa

Start Your Search

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.