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

Welcome to the enchanting region of Yucaipa, Calimesa, and Oak Glen—an idyllic corner of Southern California nestled in San Bernardino County. This area is a hidden gem, offering a unique blend of natural beauty, community spirit, and a serene lifestyle that is hard to resist.

Yucaipa, known for its picturesque landscapes and friendly neighborhoods, boasts a rich history and a vibrant community. The city is surrounded by the stunning San Bernardino Mountains, providing residents with breathtaking views and an abundance of outdoor activities. From hiking and biking to picnicking in the lush parks, there’s no shortage of ways to enjoy the great outdoors.

Just a stone's throw away, Calimesa complements Yucaipa's charm with its small-town feel and a welcoming atmosphere. This quaint city is perfect for families and retirees alike, offering a peaceful environment while still being conveniently close to urban amenities.

Nestled nearby, Oak Glen is famous for its apple orchards and seasonal festivals. This picturesque area invites you to explore its rolling hills, where you can pick fresh fruit and enjoy the beauty of nature year-round.

One of the standout features of homes in this region is the availability of properties with orchard views. Imagine waking up to the sight of blooming orchards and lush greenery right outside your window. These homes not only provide a tranquil setting but also a unique lifestyle that celebrates the beauty of nature. Whether you’re sipping morning coffee on your porch or hosting friends for a sunset barbecue, the orchard views create an enchanting backdrop for everyday life.

Discover the charm and beauty of Yucaipa, Calimesa, and Oak Glen—where your dream home with an orchard view awaits!

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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