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

Nestled in the heart of Southern California, the enchanting region of Yucaipa, Calimesa, and Oak Glen offers a unique blend of natural beauty and suburban charm. Known for its picturesque landscapes and a community that values the great outdoors, this area is a hidden gem for those seeking a serene lifestyle amidst nature’s splendor.

Yucaipa, with its rolling hills and stunning mountain views, is a haven for outdoor enthusiasts. The city boasts an array of parks, hiking trails, and recreational areas, making it ideal for families and individuals who appreciate an active lifestyle. Just a stone's throw away, Calimesa offers a quaint, small-town atmosphere while providing easy access to modern amenities and services. Oak Glen, renowned for its apple orchards and seasonal festivities, adds a touch of rustic charm and is perfect for weekend getaways and family outings.

One of the standout features of homes in this region is the breathtaking views of trees and wooded landscapes. Imagine waking up to the gentle rustle of leaves and the soothing sounds of nature right outside your window. Many properties in Yucaipa, Calimesa, and Oak Glen are thoughtfully designed to maximize these lush vistas, offering an idyllic backdrop for your everyday life. Whether you’re sipping coffee on your porch or enjoying a cozy evening by the fireplace, the beauty of the surrounding woodlands is sure to elevate your living experience.

Discover your dream home in this captivating region, where nature meets community, and every day feels like a retreat. Embrace the tranquility of Yucaipa, Calimesa, and Oak Glen – your perfect sanctuary awaits!

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

$110,000

3 Beds ⋅ 2 Baths ⋅ IG26183435 MLS ⋅ Active Status

Welcome to this inviting three-bedroom, two-bath manufactured home in Las Palomas Estates. The thoughtfully designed single-level floor plan offers a comfortable living area, a functional kitchen with generous cabinet space, and well-proportioned bedrooms. Outside, enjoy a covered two-car carport with additional usable outdoor space and beautiful surrounding views. Community amenities include a swimming pool, spa, clubhouse, recreation areas and onsite management. Conveniently located near shopping, dining and I-10 freeway access, this home combines comfort, convenience and an appealing community setting.

1134 Villa Calimesa Lane Unit 93, Calimesa

$939,900

4 Beds ⋅ 3 Baths ⋅ IV26182500 MLS ⋅ Active Status

PRICE IMPROVEMENT 9.8.2026! YOUR PRIVATE BACKYARD RETREAT AWAITS! Spectacular 2-story home located in the beautiful neighborhood of Hidden Meadows. This home features 4 spacious bedrooms all with walk-in closets, 3 full bathrooms that have all been remodeled, large living & dining room with fireplace & built-in shelves. The kitchen has also been remodeled to include more cabinet space, granite counter tops & large island/breakfast counter that opens to the family room with a wood burning stove & slider to the backyard. This first level also offers 1 of the bedrooms & full baths as well as a good size laundry room with direct access to the oversized 3 car garage. Upstairs you will find the other 3 bedrooms including the Primary suite with double door entry, vaulted ceiling, fireplace & sliding door leading to a private balcony overlooking the backyard. The expansive primary bathroom has dual sinks, large soaking tub & separate walk-in shower. This home is situated on a cul-de-sac with a backyard perfect for entertaining that includes an outdoor kitchen & amazing pool with waterfall, slide & elevated spa. Steps on either side of pool take you up to a cozy firepit to enjoy on those cool evenings. As an added bonus, you can watch beautiful sunsets from the large front porch. This is a must see!

13557 Pineridge Court, Yucaipa

$84,499

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

$949,950

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

$254,900

2 Beds ⋅ 2 Baths ⋅ SW26149200 MLS ⋅ Active Under Contract 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.

10961 Desert Lawn (508 Poplar) Drive Unit 508, Calimesa

$1,099,900

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

Motivated Seller! 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 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 (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

MASSIVE $51,000 PRICE REDUCTION! NOW OFFERED AT $899,000 AND PRICED TO SELL! Don't miss this exceptional opportunity to own one of Oak Glen's most unique turnkey homesteads. With a significant price improvement, this private retreat offers outstanding value for buyers seeking usable acreage, modern upgrades, and the peaceful mountain lifestyle that makes Oak Glen so desirable. 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.

39804 Pine Bench, 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.