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 offers a unique blend of natural beauty, small-town charm, and a vibrant community spirit, making it an ideal place to call home.

Yucaipa is renowned for its stunning landscapes, where rolling hills and scenic vistas create a serene backdrop for everyday life. With an abundance of parks, hiking trails, and outdoor activities, residents can enjoy the great California outdoors year-round. Calimesa, adjacent to Yucaipa, boasts a peaceful atmosphere and a friendly community, perfect for families and retirees alike. And just a short drive away, Oak Glen invites you to experience its apple orchards, rustic charm, and seasonal festivals, celebrating the region's agricultural heritage.

In this captivating region, you'll find a diverse selection of homes, including multi-level story options that cater to various lifestyles and preferences. These homes offer spacious layouts, perfect for growing families or those who love to entertain. With multiple levels, you can enjoy designated spaces for relaxation, work, and play, all while taking in the stunning views that this area has to offer.

Whether you’re looking for a modern home with all the latest amenities or a charming property steeped in history, Yucaipa, Calimesa, and Oak Glen have something for everyone. Experience the warmth of community living and the beauty of nature, and let this remarkable region welcome you home.

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

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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.