Yucaipa/Calimesa/Oak Glen (269) Homes with Trees/Woods View

Yucaipa/Calimesa/Oak Glen (269) Homes with Trees/Woods View

Nestled in the heart of San Bernardino County, the enchanting region of Yucaipa, Calimesa, and Oak Glen offers a unique blend of natural beauty and suburban charm. This picturesque area, known for its stunning landscapes and vibrant community, is the perfect setting for those seeking a tranquil lifestyle surrounded by nature.

Yucaipa boasts a rich history and a welcoming atmosphere, with a variety of parks, hiking trails, and outdoor recreational opportunities. The nearby San Bernardino National Forest provides countless opportunities for adventure, from hiking and biking to camping under the stars. Meanwhile, Calimesa, a quaint city with a small-town feel, is known for its friendly residents and community events, making it an ideal place for families and retirees alike.

Oak Glen, famous for its apple orchards and seasonal festivities, adds a touch of rural charm to the region. Here, you can enjoy the fresh air while picking apples in the fall or indulging in homemade pies at local bakeries.

One of the standout features of homes in this area is the breathtaking views of trees and wooded landscapes. Imagine waking up to the sight of towering pines and lush greenery right outside your window. Many properties in Yucaipa, Calimesa, and Oak Glen are designed to maximize these stunning vistas, providing a serene backdrop for your daily life. Whether you’re sipping coffee on your porch or enjoying a family gathering in your backyard, the beauty of nature is always within reach.

Discover your dream home in this idyllic region, where the charm of small-town living meets the splendor of the great outdoors. Embrace a life surrounded by nature, community, and endless possibilities!

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

$84,900
2 Beds ⋅ 1 Baths ⋅ IG26165886 MLS ⋅ Active Status
SHHHHH!!! DON'T TELL ANYBODY about this hidden gem of a Senior +55 park nestled in the hills in Calimesa! OMG, only $263.80/month for space rent???? YES! A-D-O-R-A-B-L-E remodeled TWO BEDROOM, One Bathroom singlewide PLUS the 8X12 Expando on the Living Room makes it feel like a doublewide! Cutest kitchen EVER! Featuring an ANTIQUE STOVE, fully functional gas burners and oven, refrigerator, lots of storage and plenty of room for a cozy kitchen table for that morning coffee! Or, take that coffee outside on the covered porch to enjoy the morning even more. OK, back inside to find the large, open living room area with additional room for a formal dining room table. REMODELED BATHROOM with NEW single basin lavy with a tub/shower combination. Primary bedroom has dual closets and built-in drawers, leaving ample space for your QUEEN SIZE BED. Step down to another completely remodeled 2nd bedroom (or craft room, office, hobby room, etc.). This room adds about 200 more square footage not showing on the assessors roles. Open another door and you'll find your utility room, complete with washer & dryer, storage and so much more!! THIS HOME IS TURNKEY and waiting for YOU! No neighbors behind, lots of shade trees and a true "country charm" can be felt here. WHAT ARE YOU WAITING FOR? CALL ME TO SCHEDULE AN APPOINTMENT TODAY! (Ser# 50X1FD7) Don't let the singlewide designation fool you; there's over 800 sq ft of living area in this home!

35080 Chandler Avenue Unit 54, Calimesa
$995,000
4 Beds ⋅ 5 Baths ⋅ 219150880DA MLS ⋅ Active Status
Welcome home to Hidden Meadows...one of Yucaipa's most sought-after communities, tucked just minutes from the apple orchards, wineries, and mountain charm of Oak Glen. Set on a sprawling, parklike lot of just over half an acre, this completely remodeled and meticulously updated residence delivers the kind of turnkey luxury that rarely comes to market.Step inside to a formal dining room anchored by a stunning stacked-stone fireplace and warmed by a candlelit chandelier, creating the perfect setting for holiday gatherings and dinner parties. Rich wood-look flooring flows throughout the main level, tying together every space with timeless, classic elegance.The fully remodeled gourmet kitchen is a true showpiece, featuring dramatic leathered-granite countertops, custom wood cabinetry, a stone tile backsplash, a large center island with bar seating, and stainless-steel double wall ovens plus a professional-style range -- a dream for any culinary enthusiast. The kitchen opens seamlessly into an inviting family room, where a second river-rock fireplace, built-in shelving, and a wall of glass sliders frame lush backyard views and flood the space with natural light.Downstairs, a versatile office/den offers flexible living, currently used as a comfortable guest retreat, and easily reimagined as a potential fifth bedroom for growing or multigenerational households. Two conveniently placed half bathrooms round out the main level, including one tucked near the garage, ideal for effortless indoor-outdoor entertaining.Upstairs, all four bedrooms and three full bathrooms are generously sized with beautiful views. The primary suite is a true escape, crowned by dramatic vaulted, beamed ceilings and a private balcony overlooking the tranquil, tree-lined backyard. The spa-inspired ensuite bath impresses with a freestanding soaking tub, dual furniture-style vanities framed by elegant mirrors, and an oversized subway-tile walk-in shower, a daily retreat that feels like a five-star getaway.With numerous upgrades and meticulous care throughout, this Hidden Meadows gem offers the rare combination of refined luxury, everyday flexibility, and a truly unbeatable location, all within reach of Oak Glen's orchards, hiking trails, and small-town charm. Don't miss your chance to call this extraordinary property home!

37254 Ironwood Drive, Yucaipa
$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
$346,000
2 Beds ⋅ 2 Baths ⋅ IG26155477 MLS ⋅ Active Status
OWN THE LAND. LOVE THE LIFESTYLE. LIVE THE GOOD LIFE! Welcome to Sharondale—one of Calimesa's most sought-after 55+ communities—where beautifully manicured grounds, resort-style amenities, and an unbeatable sense of community await. Better yet, this spacious manufactured home is situated on a permanent foundation, meaning you own the land and enjoy all the perks of low-maintenance living! Offering nearly 1,900 square feet of living space, this two-bedroom, two-bathroom home is perfectly positioned on a premium lot backing directly to the clubhouse, providing fantastic privacy and peaceful views that are hard to come by. Step inside and discover room to spread out with a large formal living room, formal dining room, spacious kitchen, and an inviting family room complete with a cozy fireplace and sliding glass door leading to the front patio—the perfect spot to unwind and enjoy Calimesa's beautiful weather. Whether you're hosting family for the holidays or enjoying a quiet evening at home, this floor plan offers the space and flexibility you've been looking for. The oversized primary suite is a true retreat featuring a large closet, vanity area, private bathroom, and its own sliding glass door leading to the covered back patio—your own private escape just steps away. Need extra space? The bonus room located just off the back of the carport is ideal for storage, hobbies, crafts, or a workshop. Sharondale residents enjoy mature landscaping, a sparkling pool and spa, an impressive clubhouse, and a reasonable HOA fee of just $270 per month, which includes water and sewer (per HOA). Space. Privacy. Amenities. Ownership. Homes like this don't come around often. If you've been dreaming of an active and carefree lifestyle without sacrificing comfort or square footage, your next chapter begins right here at 9423 Corbie Court.

9423 Corbie Court, Calimesa
$285,000
2 Beds ⋅ 2 Baths ⋅ SW26149200 MLS ⋅ Active Status
Welcome to Plantation on the Lake, Southern California’s premier 55+ retirement community! This well maintained 2 bed + office, 1-3/4 ba (walk-in shower in primary) offering the perfect blend of living space and functionality. Enjoy whole-house plantation shutters for added privacy and timeless style, along with high-efficiency ceiling fans throughout. The large eat in kitchen features a nice size island as well as a walk-in pantry and in the laundry room enjoy direct access to the attached "rare" oversized garage with room for cars, recreational vehicles, tools, and additional storage. Experience true resort-style living with an impressive array of amenities, including recreation centers, sparkling pools, relaxing hot tubs, fitness centers, pickleball courts, dog parks, libraries, billiards, card rooms, fire pits, and a full calendar of social activities and community events. Beautifully maintained grounds and a welcoming atmosphere make it easy to enjoy an active or peaceful lifestyle. Located near new shopping centers, everyday conveniences, and major freeways. This home offers exceptional value and convenience, including, refrigerator, range, washer and dryer. As an added bonus, the seller is offering the option to keep the home partially furnished, making your move-in even easier!

10961 Desert Lawn (508 Poplar) Drive Unit 508, Calimesa
$1,159,000
3 Beds ⋅ 4 Baths ⋅ IV26145190 MLS ⋅ Active Status
Welcome to your private retreat in Yucaipa's highly sought-after Wildwood/Hidden Meadows area, where natural beauty, comfort, and peaceful living come together. Nestled on a sprawling, park-like lot surrounded by mature oak trees, towering evergreens, lush greenery, and a year-round running stream, this exceptional property offers a rare setting unlike any other. A stunning rock waterfall welcomes you home, while serene pathways, shaded outdoor spaces, and the soothing sound of the flowing stream create a peaceful atmosphere. Enjoy morning coffee on the deck, evenings under the stars, or relax beneath the covered patio surrounded by nature. Inside, the home has been refreshed with fresh interior paint and new upstairs carpet. Large windows fill the home with natural light while showcasing beautiful views of the surrounding landscape. The chef's kitchen offers generous workspace and storage, making it ideal for entertaining and everyday living. Cozy living areas provide the perfect setting to gather around the fireplace. The spacious primary suite features dual walk-in closets and ample space to unwind. Additional features include a built-in whole-house vacuum system, whole-house intercom, a 360-degree security camera system with whole-house alarm, a 220V EV charging outlet in the garage, a new gas water heater, and an impressive 59-panel solar system for added energy efficiency. The outdoor living space offers room to entertain, garden, explore, or simply enjoy the peaceful surroundings. Located in the desirable Wildwood/Hidden Meadows area, this property offers a unique blend of privacy and convenience with easy access to hiking trails, local parks, schools, shopping, dining, and all that Yucaipa has to offer. This is a rare opportunity to own a truly one-of-a-kind property where nature, privacy, and modern conveniences come together in one exceptional setting.

13515 Oak Mountain, Yucaipa
$242,000
IG26136941 MLS ⋅ Active Status
BUILD YOUR DREAM ESTATE IN PRESTIGIOUS HIDDEN MEADOWS! Rare opportunity to own 2.84 acres in the highly sought-after Hidden Meadows community, surrounded by stunning custom homes and million-dollar estates. The property has been professionally surveyed and roughly graded, with a water meter already installed on site and utilities conveniently available at the street. Enjoy breathtaking surroundings, privacy, and the opportunity to create a custom home tailored to your lifestyle in one of the area's most desirable neighborhoods. Whether you're ready to build now or invest in a premier piece of land for the future, this exceptional property offers endless possibilities. Don't miss your chance to build the home you've always imagined in Hidden Meadows!

13582 Oak Mountain Drive, Yucaipa
$888,000
5 Beds ⋅ 3 Baths ⋅ IG26106814 MLS ⋅ Active Under Contract Status
Improved Price! Welcome Home to 36246 Canyon Terrace Drive in Yucaipa’s Prestigious Whisper Ranch (NO HOA!). Meticulously-maintained one-owner home ~ Thoughtfully upgraded inside and out ~ Premium view lot with no neighbors behind which offers beautiful views of the local mountains, city lights, and the mature oak trees which span from the back of the property to the hiking trail below. There’s so much to discover inside and out, but let’s start in the backyard which begins with a covered patio retreat with remote-controlled floor-to-ceiling privacy screens to enclose it when desired with a TV & heater for year-round enjoyment. Artists, hobbyists, do-it-yourselfers, & those who just like a space to call their own have 2 great options here - a studio on one side of the yard & a larger workshop by the 3-car garage (both have windows, finished walls & lights). Enjoy the low maintenance yard with abundant concrete patio areas, high-end artificial lawn, & delicious navel orange trees. Inside, in addition to the features expected in Whisper Ranch homes, we have abundant upgrades starting with the gorgeous contemporary kitchen remodel with slab granite countertops with waterfall edges on the island, soft-close KraftMaid cabinetry with customized inserts, stainless steel appliances (including a slide-in gas range with a split convection oven & a super-quiet dishwasher), attractive tile backsplash, & a double porcelain sink. Next, is the fabulous new flooring - engineered hardwood adorns most of the main floor. All 5 bedrooms (3 beds upstairs/2 down) have new luxurious carpet with plush padding to warm your toes on those chilly winter nights. In summer, the 3-year-new 5-Ton Lennox AC & new ducting keeps you cool with maximum efficiency. The family room & primary suite offer glass doors with encased blinds & Phantom screens. Counters in the 3 baths, laundry room, & on the linen cabinet are topped with more gorgeous granite. Most window coverings are upgraded & many also have solar shade screens installed for energy efficiency. Premium wall mount LiftMaster shaft garage door openers. Exterior holiday lights on a timer installed for convenience. New water heater in 2025. Whisper Ranch is known for rolling hills with sidewalks in front surrounded by hiking trails to explore along the perimeter! Please view the photos, floor plan & virtual tours for more details, then contact your trusted real estate advisor to tour it and make it your very own. You deserve this!

36246 Canyon Terrace Drive, Yucaipa
$499,900
1 Beds ⋅ 2 Baths ⋅ IG26106532 MLS ⋅ Active Status
Nestled in the heart of picturesque Oak Glen, this absolutely charming mountain retreat offers the perfect blend of rustic character, comfort, and privacy. Ideally located near renowned apple orchards, boutique shopping, quaint restaurants, and year-round seasonal attractions, this beautifully maintained home features 1 bedroom, 1.75 bathrooms, and 1,052 sq. ft. of inviting living space on an expansive 15,300 sq. ft. lot with room for potential expansion. A welcoming brick walkway with decorative planters leads to the spacious wraparound deck, creating the perfect setting to relax and enjoy the serene mountain surroundings. Inside, the home showcases soaring vaulted wood-beamed ceilings, plantation shutters, central heating and air conditioning, and newly installed rodent-resistant aluminum flex ducting beneath the home. The spacious living room is warm and inviting with a cozy wood-burning stove, while the adjoining kitchen features wood cabinetry, tile countertops, and premium Bosch stainless steel appliances including a built-in oven, cooktop with vent hood, and microwave. The Samsung refrigerator, washer, and dryer are all included. The light-filled dining area opens to the front deck through elegant French doors, creating seamless indoor-outdoor living. The generously sized bedroom offers direct access to the back deck through a glass slider and includes a private ensuite bathroom with vanity area, walk-in shower, and an ideal cedar-lined walk-in closet with built-in storage. A full guest bathroom completes the interior. Step outside to the peaceful back deck and take in the breathtaking forest and mountain views. Additional amenities include a detached 2-car garage, 1-car carport, driveway parking for up to 4 additional vehicles, and a storage shed. Whether you are looking for a full-time residence, weekend getaway, or investment opportunity, this Oak Glen gem offers the very best of mountain living while still being conveniently close to shopping, services, and the nearby US Forestry Service Station. A rare opportunity you do not want to miss!

39370 Clearwater Drive, Yucaipa
$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
$745,000
4 Beds ⋅ 3 Baths ⋅ IG26066527 MLS ⋅ Active Under Contract Status
Back on market at no fault of the seller's. Welcome to this beautiful two-story home in the popular Chapman Heights community of Yucaipa. This home sits in a great location with amazing views of the golf course and has been updated over the last three years. As you walk in, you’ll notice the high ceilings and open feel right away. The home has 4 bedrooms and 3 bathrooms, including a bedroom and full bathroom downstairs, perfect for guests or family. Upstairs, the primary bedroom has its own fireplace and a private balcony with great views. The primary bathroom includes a soaking tub, separate shower, and a large walk-in closet with natural light. Many updates have already been done for you, including new paint inside and outside, new flooring throughout the entire home (including the stairs), and an updated kitchen with new countertops, backsplash, and appliances. The home also has brand new high-efficiency A/C units to help keep you comfortable. The kitchen offers plenty of counter space, double ovens, a pantry, and easy access to the laundry room. Other features include ceiling fans, plantation shutters, and crown molding. Upstairs also includes a loft and an office area. The backyard is great for relaxing or entertaining, with newer pavers, a large covered patio, and peaceful golf course views. The front yard has also been updated with newer landscaping. The home also includes finished garage spaces that can be used for a gym, workshop, or extra storage. Located close to parks, shopping, restaurants, hiking trails, and schools, this home is move-in ready and in a great neighborhood. *Some photos have been digitally staged and virtually enhanced.*

11907 Southwind Way, Yucaipa
$14,500,000
3 Beds ⋅ 5 Baths ⋅ IV25253989 MLS ⋅ Active Status
Step into a storybook setting... an extraordinary One-of-a-Kind Castle nestled in the beautiful mountain community of Oak Glen California. This magical Estate is tucked away in a forest yet conveniently located, offering easy access and feeling worlds apart from the city. Just 11 minutes from Yucaipa, about an hour from Lake Arrowhead and only 90 minutes from Los Angeles, it is a rare find that blends convenience with absolute privacy. Designed as a true Castle showplace, the property features an impressive grand entertaining Lounge... perfect for large gatherings, celebrations, or quiet evenings in regal style. With its timeless design and beautiful natural setting, this remarkable property offers a rare blend of nostalgia, unique character, and privacy. One of a Kind! Oh So Magical!! Attention Actors, Producers, Writers...Your Dream Come True Property. Approximately 6.73 Acres.

38838 Birch Creek, Oak Glen
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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.