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

Welcome to the enchanting region of Yucaipa, Calimesa, and Oak Glen, nestled in the heart of San Bernardino County, California. This picturesque area is known for its stunning landscapes, charming neighborhoods, and a warm community spirit that makes it a wonderful place to call home.

Yucaipa is celebrated for its beautiful foothills and breathtaking views, particularly those that showcase the lush orchards that dot the landscape. The region is renowned for its agricultural heritage, offering residents the unique opportunity to enjoy homes with orchard views. Imagine waking up each morning to the sight of blooming fruit trees, fragrant blossoms, and the vibrant colors of nature right outside your window. The orchards not only provide a serene backdrop but also contribute to the area's rich farming culture, with local markets offering fresh produce and homemade goods.

Just a stone's throw away, Calimesa boasts a charming small-town atmosphere, perfect for families and retirees alike. With a variety of parks, hiking trails, and community events, Calimesa is a haven for outdoor enthusiasts and those seeking a close-knit community.

Venture a bit further, and you'll discover Oak Glen, a hidden gem known for its apple orchards and seasonal festivities. This quaint area is perfect for weekend outings, offering apple picking, cider tasting, and picturesque picnic spots.

Whether you're looking for a cozy family home or a serene retreat, Yucaipa, Calimesa, and Oak Glen offer a diverse range of properties with stunning orchard views, making this region an idyllic setting for your next chapter. Embrace the charm and beauty of this remarkable area and discover your dream home today!

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

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 219150501DA MLS ⋅ Active Status

Incredible opportunity to own this sprawling estate, recently acquired through foreclosure proceedings. A nearly 4,000 sq. ft. two story country residence with brick facade and grand entry hall. Home has been updated with beautiful custom cabinetry, updated baths, granite countertops and many other upgrades. 4.74 acre property is breathtaking and perched on a promontory with sweeping 360 degree views of city lights, San Gorgonio, San Jacinto, and most every mountain range in the Southern California vicinity. Past the remote controlled entry gates of the exclusive Oak Hills Estates, you enter your compound via a long sweeping private driveway. 3 car attached garage, large pool and spa, extensive solar array, private orchards and vineyards, and two ponds and a steam highlight the extensive grounds and improvements.

37245 Valgio Drive, Calimesa

$950,000

4 Beds ⋅ 3 Baths ⋅ IG26070989 MLS ⋅ Active Status

Nestled in the heart of Oak Glen, this private homestead offers a rare opportunity to experience true mountain living with the convenience of nearby city access. Set on nearly all usable acreage, the property is surrounded by mature trees, fresh mountain air, and a peaceful, secluded setting that captures the essence of Oak Glen’s four distinct seasons. The extensively updated home blends modern upgrades with rustic charm. Improvements include new windows, French doors, heating and air conditioning, maintenance-free James Hardie siding, and a tankless water heater for long-term efficiency and comfort. Inside, the inviting interior features granite countertops, hardwood floors, a wood-burning stove in the family room, and a fireplace with heatalator in the living room. The thoughtful floor plan offers 4 bedrooms and 3 full bathrooms, ideal for full-time living, multi-generational use, or a private retreat. The land itself is a standout feature, offering both beauty and functionality. An established orchard with over 30 fruit trees—including apple, pear, and plum—creates a true homestead environment with room to expand gardens, outdoor living areas, or additional agricultural use. Seasonal hummingbird migrations and local wildlife further enhance the natural setting. A fully equipped multi-room barn with attached workshop provides exceptional versatility, complete with plumbing, electrical, and two wood-burning stoves for year-round use. Whether for woodworking, metalwork, car restoration, creative studio space, or storage, the possibilities are extensive. Two additional outbuildings add even more flexibility and value. Infrastructure and reliability are unmatched, featuring a whole-property Generac backup generator servicing the home, barn, and pump house—an extremely rare and valuable feature in mountain communities. The private well is known for its high-quality Oak Glen water, providing both independence and peace of mind. Despite its private setting, the property is just minutes from Yucaipa and Redlands, offering convenient access to dining, shopping, and everyday amenities. This is a unique opportunity to own a turnkey Oak Glen homestead combining usable land, modern upgrades, and a lifestyle defined by space, nature, and tranquility.

39804 Pine Bench, 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.