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

Nestled in the heart of Southern California, the charming communities of Yucaipa, Calimesa, and Oak Glen offer a delightful blend of natural beauty, rich history, and a vibrant lifestyle. Known for their stunning mountain views and lush landscapes, this region is a hidden gem that attracts those seeking both tranquility and adventure.

Yucaipa boasts a warm, inviting atmosphere with a strong sense of community. It’s a place where neighbors become friends, and local events bring everyone together. The city is surrounded by the San Bernardino Mountains, offering endless opportunities for outdoor enthusiasts to hike, bike, and explore. With its picturesque parks and thriving farmers' markets, Yucaipa is perfect for families and individuals alike.

Just a stone's throw away, Calimesa is a quaint town that exudes small-town charm. It features a growing number of amenities, including boutique shops and cozy cafes, making it an ideal spot for relaxation and leisure. The community is known for its friendly vibe and scenic golf courses, making it a favorite among retirees and young families.

Oak Glen, famous for its apple orchards and seasonal festivals, is a must-visit for anyone in the area. This idyllic setting not only offers breathtaking views but also a chance to experience farm-to-table living with fresh produce and homemade goods.

For those seeking homes with orchard views, this region is a dream come true. Imagine waking up to the sight of rolling orchards and majestic mountains right outside your window. With a variety of properties available, from charming cottages to modern estates, you can find your perfect slice of paradise in Yucaipa, Calimesa, or Oak Glen. Come discover the beauty and warmth of this exceptional region, where every day feels like a getaway!

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

$899,000

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.