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, this area is surrounded by majestic mountains and lush greenery, making it a haven for nature lovers and outdoor enthusiasts alike. With its mild climate and abundant sunshine, residents enjoy a year-round opportunity to explore the stunning trails, orchards, and parks that define this vibrant community.

One of the most appealing aspects of this region is the availability of homes with breathtaking views of trees and woods. Imagine waking up to the gentle rustle of leaves and the serene sight of towering pines right outside your window. These homes provide a perfect retreat from the hustle and bustle of city life, allowing you to immerse yourself in the tranquility of nature. Whether you’re sipping your morning coffee on the porch or hosting a family gathering in your backyard, the enchanting views create an idyllic backdrop for everyday living.

Yucaipa, Calimesa, and Oak Glen are also known for their friendly communities, excellent schools, and a variety of local amenities. From charming boutiques to delightful dining options, residents have everything they need within reach. Plus, the close-knit atmosphere fosters a sense of belonging, making it easy to forge lasting friendships.

If you’re seeking a home that offers both comfort and a connection to nature, look no further than this captivating region. Discover the beauty of Yucaipa, Calimesa, and Oak Glen, where your dream home awaits amidst the trees.

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

$470,000

1 Beds ⋅ 2 Baths ⋅ IG26228554 MLS ⋅ Active Status

Located in the heart of picturesque Oak Glen, this 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

$399,000

2 Beds ⋅ 2 Baths ⋅ IG26218062 MLS ⋅ Active Status

Welcome to Gingertree Trail! Tucked away in Upper Yucaipa's coveted Country Village, this light-filled 2-bed, 2-bath gem is the one you've been waiting for! Step inside to soaring vaulted ceilings and a living room that frames peaceful greenbelt views to the east, the perfect backdrop for morning coffee or relaxing evenings. The updated kitchen shines with upgraded cabinetry and stainless steel appliances, opening right out to your private enclosed patio for easy indoor-outdoor living. The primary suite is your own retreat, with large closets, a private bath, and its own slider to the patio. A spacious guest bedroom, full guest bath, indoor laundry, and plenty of storage round out 1,005 sq ft of smart, comfortable living. Enjoy a two-car carport with an exterior storage closet, plus the ease of HOA-maintained landscaping outside the fence line. But the real magic is the lifestyle! Lounge by the sparkling pool and spa, unwind under the covered patios, or host your next celebration in the stunning clubhouse, complete with a kitchen, sound system, tables, chairs, and restrooms, all included in your HOA dues. Stroll tree-lined pathways through mature landscaping in this self-managed, immaculately kept community of just 96 homes. Opportunities like this don't last long, and it's priced to sell. Schedule your showing today! **This is NOT a 55+ community, all are welcome!**

36202 Gingertree, Yucaipa

$750,000

4 Beds ⋅ 3 Baths ⋅ IG26208654 MLS ⋅ Active Under Contract Status

Escape to the tranquility of the woods with this exceptional single-story retreat, perfectly situated just minutes from the scenic trails of Wildwood Canyon State Park and the charming atmosphere of Oak Glen. As you turn onto Oak Grove Road, the stresses of the city simply fade away. This spacious home offers four bedrooms and three bathrooms, situated on a sprawling lot of over three-quarters of an acre. This property is ready for your personal vision and updates to transform it into your dream home. Enjoy the outdoors on the expansive patio, and take advantage of the convenience of an oversized two-car attached garage and additional storage shed. Your private getaway awaits.

37242 Oak Grove, Yucaipa

10961 Desert Lawn Drive Unit 409, Calimesa

$274,900

3 Beds ⋅ 2 Baths ⋅ NP26204139 MLS ⋅ Active Status

CORNER LOT! Beautiful 3-bedroom 2 bath home with an 11X32 room addition in one of the Inland Empires desired 55+ communities. This home has a living room, family room, dining area, wraparound kitchen, utility room w/ a sink, fireplace & a jacuzzi for you to enjoy. The master bedroom can accommodate a king size bed comfortably w/ additional furniture and it also has a retreat w/ its own exit and entry to the room addition. The master bathroom has a walk-in shower complete w/ grab bars, making it convenient for the Golden years. There are 2 other good-sized bedrooms, great for guests if needed or for yourself. The family room is adjacent to the kitchen which makes it comfortable especially when you have company. The fireplace just adds that little extra touch. The 2-car garage is attached and is really convenient when bringing home groceries or other items. The room addition was previously used as an art room, the possibilities are endless of what else it could be used for. The backyard is fenced with decorative fencing, great for a little bit of privacy or if you have a pet that would work too. The front porch has a swing attached for just enjoying the quiet evenings in the middle of daily life.

10961 Desert Lawn Drive Unit 409, Calimesa

$999,000

5 Beds ⋅ 4 Baths ⋅ IG26199521 MLS ⋅ Active Status

A spectacular VIEW home masterfully designed to accommodate Several Generations! *** NO HOA *** Whether bringing parents closer, giving adult children their own space, or creating a home where generations can gather for years to come, this is truly a special opportunity to invest in your family’s legacy without compromising comfort, privacy, or style. Soaring ceilings, expansive windows, abundant natural light, and breathtaking panoramic views create an impressive sense of space from the moment you enter. This thoughtfully designed floor plan offers incredible flexibility, beginning with a main-level bedroom and full bath, ideal for parents, adult children, extended family, or guests. Additionally, this main level offers two formal living areas, formal dining area and a regal den/office with soaring ceilings! A central Gourmet Kitchen featuring Two Pantries ( one walk in ) and full amenities is the heart of the home where everyone is sure to gather! Storage is more than abundant throughout this home as well! Ascend the Grand staircase to find two separate wings creating a rare sense of privacy! One wing is dedicated to the luxurious primary suite, complete with a private office tucked at the back, beautifully appointed spa-inspired bathroom with stunning tilework, an expansive walk-in closet and a private balcony showcasing spectacular views. Across the hall you find a separate wing providing both a Jack-and-Jill bedroom arrangement sharing a full bath, PLUS an additional bedroom and bathroom (with an expansive loft / living area separating the sleeping quarters) creating the perfect place to relax, entertain, work, or play upstairs as well. This exceptional 5-bedroom, 4-bath residence was thoughtfully designed for multiple generations to live, gather, and grow together—without sacrificing privacy or luxury. Outside, a covered patio and lush green lawn invite year-round California living, all framed by sweeping panoramic views. A 4 CAR TANDEM GARAGE and EXPANSIVE DRIVEWAY offer ample parking for everyone as well! Lastly, it's efficient with Owned Solar! Homes offering this level of space, flexibility, and multigenerational living are incredibly hard to find. Don’t miss your opportunity to experience it before anyone else—this one won’t last!

36358 Canyon Terrace, Yucaipa

$1,199,999

5 Beds ⋅ 4 Baths ⋅ IG26200238 MLS ⋅ Active Status

Mountain views. Poolside sunsets. Dinner by the fire. Weekends in Oak Glen just up the road. This is Hidden Meadows living. Tucked into one of Yucaipa’s most sought-after neighborhoods, this beautifully remodeled single-story home pairs nearly 3,000 square feet of flexible living space with dramatic architecture, sweeping foothill views, and a backyard designed for year-round entertaining. Soaring vaulted ceilings, skylights, and walls of windows flood the main living spaces with natural light while framing the surrounding foothills. A sunken formal living room and adjoining dining space are anchored by two dramatic raised-hearth tiled fireplaces, while a built-in wet bar creates a natural gathering point. Expansive glass doors blur the line between indoors and out, opening the living spaces to the pool deck and surrounding views. The modernized kitchen combines two-tone cabinetry, stone countertops, breakfast bar, abundant storage, and an oversized walk-in pantry, with an easy flow between indoor and outdoor gathering spaces. The single-story layout offers five bedrooms and four bathrooms, highlighted by an impressive primary retreat with a generous sitting area and direct backyard access. Its remodeled en suite bath feels like a private spa, with a freestanding soaking tub, oversized glass shower, dual vanity, and serene finishes. On the opposite side of the home, a separate bedroom and adjacent bath beyond the kitchen create a flexible setup for guests, extended family, a private office, or multigenerational living. And then there’s the backyard: an expansive pool deck wraps around a sparkling pool and raised spa, with multiple places to lounge, dine, gather, and take in the mountain views. A covered outdoor kitchen and built-in seating make outdoor meals easy, while the oversized deck leaves plenty of room for quiet evenings or full-scale summer pool parties. Beyond the pool, low-maintenance turf, garden space, a chicken coop and small-animal enclosures bring a little of Yucaipa’s semi-rural character home, while a dedicated RV or boat parking pad adds hard-to-find flexibility. And when it’s time to leave home, the orchards, trails, restaurants, cider, and seasonal traditions of Oak Glen are just minutes up the road — close enough to make apple picking, mountain hikes, and cool fall afternoons part of an ordinary weekend.

13582 Oak Hill Court, Yucaipa

$76,900

1 Beds ⋅ 1 Baths ⋅ IG26194380 MLS ⋅ Active Status

BACK ON THE MARKET through No Fault of the Seller! WAS a TWO Bdrm, now only a ONE Bdrm...but that could change quickly! Lovely, quiet, tucked away +55 Senior park with Super Low space rent of only $263.56/mo. 12X60 with an Expando in living room, an enclosed porch and a separate room for the washer & dryer, laminate flooring throughout, super open and spacious with a FABULOUS BACK YARD to enjoy! Fully landscaped with lovely views and no neighbors behind you, this home is waiting for YOU! Includes, refrigerator, freestanding range/oven, dishwasher, disposal, and washer. Dryer just decided to quit working, but the gas hookups are there. NEW Kitchen cupboards, open to living area with a breakfast bar, room for a table & chairs too!. Primary bathroom has large Walk-In Shower. Look at the pictures then call to see this home asap! (Serial# S2601616)

35080 Chandler Avenue Unit 43, Calimesa

$879,000

4 Beds ⋅ 3 Baths ⋅ IV26182500 MLS ⋅ Active Status

PRICE IMPROVEMENT 10.19.2026! 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

$77,500

2 Beds ⋅ 1 Baths ⋅ IG26165886 MLS ⋅ Active Status

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! Only $275.30/month for space rent???? YES!

35080 Chandler Avenue Unit 54, Calimesa

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

$264,900

2 Beds ⋅ 2 Baths ⋅ SW26149200 MLS ⋅ Active Status

LUCKY YOU this beautiful home is back on the market, at NO FAULT of the seller. Welcome to this move-in ready home in a prime location of the 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 and seller is having brand new carpet installed! 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!

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

$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

$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

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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.

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

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

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