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

Nestled in the heart of Southern California, the charming communities of Yucaipa, Calimesa, and Oak Glen offer a unique blend of suburban comfort and natural beauty. This picturesque region is renowned for its stunning landscapes, where rolling hills and lush greenery create a serene backdrop for everyday life. With its close proximity to both the San Bernardino Mountains and the expansive San Bernardino National Forest, residents can enjoy a plethora of outdoor activities, from hiking and biking to apple picking in the famed orchards of Oak Glen.

The real estate market in this area is thriving, particularly for those seeking homes with breathtaking views of trees and woods. Imagine waking up each morning to the gentle rustle of leaves and the soft chirping of birds, all from the comfort of your own home. Many properties feature expansive windows that frame the natural beauty outside, allowing you to soak in the tranquil surroundings. Whether you’re looking for a cozy cottage or a spacious family home, the options here are as diverse as the landscape itself.

Yucaipa, Calimesa, and Oak Glen not only provide stunning views but also a warm sense of community. Enjoy local events, farmers' markets, and charming shops that make this region a delightful place to call home. With its rich blend of nature and community spirit, it’s easy to see why so many are drawn to this hidden gem in California. Discover your dream home in this enchanting area and embrace a lifestyle filled with beauty and tranquility.

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

10961 Desert Lawn Dr (527 Robellini Rd) Unit 527, Calimesa

$294,500

3 Beds ⋅ 2 Baths ⋅ IG26211300 MLS ⋅ Active Status

Beautiful 3-Bedroom Home in a Desirable 55+ Community Welcome home to this beautiful 3-bedroom, 2-bath residence offering comfort, style, and an exceptional 55+ community lifestyle. The dazzling kitchen provides a wonderful space for preparing meals and gathering with friends and family, while the spacious living room offers plenty of room to relax. A separate dining area makes entertaining effortless. Enjoy beautiful views from both the front and back of the home, adding to its inviting appeal. Just moments away, the community recreation center offers an array of amenities, including refreshing pools, relaxing hot tubs, and pickleball courts—perfect for staying active and enjoying the Southern California lifestyle. Conveniently located near local shopping, dining, and entertainment, with easy freeway access for commuting and exploring the surrounding area. This home offers the perfect combination of comfortable living, recreation, convenience, and community.

10961 Desert Lawn Dr (527 Robellini Rd) Unit 527, Calimesa

$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

$775,000

4 Beds ⋅ 3 Baths ⋅ IG26208302 MLS ⋅ Active Status

Welcome to the highly sought after Oak Glen lifestyle! This beautiful 4-bed, 3-bath, 2,013 sq. ft. home sits on a secluded 2.81 acres and features solar, a private water well, and a peaceful stream running through the property. Surrounded by beautiful apple orchards and the mountains, this property offers the peaceful feel of mountain living without the long mountain drive. Start your mornings with a cup of coffee on the spacious covered porch, settle into a rocking chair, and enjoy the soothing sounds of the stream and the beauty of your surroundings. Inside, you’ll find luxury vinyl flooring, a spacious primary suite, and a versatile bonus room just beyond the primary bathroom. This flexible space can be used as additional closet space, storage, a home office, hobby room, or whatever fits your lifestyle. The inviting kitchen features shaker-style cabinetry and butcher block countertops, creating a warm and welcoming space for everyday living, family gatherings, and entertaining. The garage has been walled in to create additional usable interior space, while the original garage door fixtures remain in place, offering flexibility for future use or conversion back to a garage if desired. With solar, a private water well, 2.81 acres, and a stream, there is plenty of room to enjoy a more self-sufficient and relaxed lifestyle. And if you’ve always dreamed of a little more room for your country living adventures, bring the horses, chickens, goats, cows, and all the fun that comes with them! Enjoy the space to garden, explore, relax, or simply take in the fresh mountain air. Spend your days surrounded by apple orchards, listening to the stream, relaxing on the porch, and enjoying the freedom that comes with having room to spread out. This is Oak Glen living at its best peaceful, private, and full of possibilities, all while being conveniently close to town.

38203 Potato Canyon, Oak Glen

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

1134 Villa Calimesa Lane Unit 93, Calimesa

$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

$909,900

4 Beds ⋅ 3 Baths ⋅ IV26182500 MLS ⋅ Active Status

PRICE IMPROVEMENT 9.23.2026! 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

$82,500

2 Beds ⋅ 1 Baths ⋅ IG26165886 MLS ⋅ Active Status

THE SECRET IS OUT! this hidden gem of a Senior +55 park is nestled in the hills in Calimesa! OMG, only $275.30/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

$924,924

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

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

$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

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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.