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 renowned for its stunning natural beauty, vibrant community spirit, and a lifestyle that effortlessly blends rural charm with modern convenience.

Yucaipa, with its stunning mountain views and lush landscapes, offers a serene escape from the hustle and bustle of city life. Residents enjoy a variety of outdoor activities, from hiking in the nearby San Bernardino National Forest to exploring the charming local parks. Calimesa, just a stone's throw away, is known for its friendly neighborhoods and family-oriented atmosphere, making it a perfect place to call home. Meanwhile, Oak Glen is celebrated for its apple orchards and seasonal festivals, providing a delightful taste of country life.

One of the standout features of homes in this region is the breathtaking orchard views that many properties offer. Imagine waking up to the sight of blossoming trees and the sweet scent of fresh fruit in the air. These homes not only provide a beautiful backdrop but also a unique opportunity for those who appreciate the beauty of nature and desire a lifestyle that embraces outdoor living.

Whether you are looking for a cozy cottage or a spacious family home, the Yucaipa/Calimesa/Oak Glen area has something for everyone. With its rich agricultural heritage, friendly community, and stunning landscapes, this region is truly a hidden gem waiting to be discovered. Come and experience the charm of life with orchard views in this idyllic part of California!

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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