Yucaipa/Calimesa/Oak Glen (269) Homes with Pool

Yucaipa/Calimesa/Oak Glen (269) Homes with Pool

Nestled in the serene foothills of Southern California, the charming communities of Yucaipa, Calimesa, and Oak Glen offer a unique blend of natural beauty, small-town charm, and a vibrant lifestyle. Known for their stunning landscapes and welcoming atmosphere, these areas are perfect for those seeking a peaceful retreat without sacrificing modern conveniences.

Yucaipa is celebrated for its picturesque parks, hiking trails, and a rich history that can be seen in its quaint downtown area. The city boasts a variety of homes, many of which come with the added luxury of private pools, providing a perfect oasis for relaxation and entertainment. Imagine sunny afternoons spent by your pool, surrounded by the breathtaking views of the San Bernardino Mountains.

Just a stone’s throw away, Calimesa offers a tranquil suburban environment with a growing community spirit. Here, you’ll find a range of homes featuring pools, ideal for those warm California days. Residents enjoy easy access to local amenities, golf courses, and a strong sense of community, making it a wonderful place for families and retirees alike.

Oak Glen, known for its apple orchards and stunning nature trails, is a hidden gem where the beauty of the outdoors is just as inviting as the homes themselves. Many properties in this area feature pools, allowing you to soak in the stunning surroundings while enjoying the comfort of your own backyard.

Whether you’re looking for a serene escape or a vibrant community, Yucaipa, Calimesa, and Oak Glen promise a lifestyle that’s both charming and fulfilling, with homes that offer the perfect blend of comfort and leisure. Explore the possibilities and discover your dream home with a pool in this idyllic region of California!

Newest Yucaipa/Calimesa/Oak Glen (269) Homes with Pool

$809,000
3 Beds ⋅ 3 Baths ⋅ IG26195435 MLS ⋅ Active Status
Welcome home to this beautiful single-story property located in a desirable Yucaipa neighborhood! Featuring 3 bedrooms, 2.5 bathrooms, plus a dedicated office, this home offers a comfortable and inviting layout perfect for everyday living and entertaining. Step outside to your own backyard retreat featuring a sparkling pool and relaxing hot tub, surrounded by beautiful views and breathtaking sunsets. Additional highlights include a 3-car garage, central vacuum system, and leased solar. Whether you’re relaxing poolside, entertaining family and friends, or ending the day with a beautiful sunset, this is a home you’ll want to experience in person. Come see the lifestyle this home has to offer—schedule your private showing today and picture yourself calling it home!

13690 Chaparral trail, Yucaipa
$830,000
4 Beds ⋅ 3 Baths ⋅ IG26192896 MLS ⋅ Active Status
Welcome to this beautiful 4-bedroom, 3-bath home in the desirable Whisper Ranch neighborhood, offering an open floor plan designed for comfortable living and entertaining. Located in a well-established community with no HOA, this home combines privacy, space, and thoughtful upgrades. The backyard is a true retreat, featuring a recently redone in-ground pool and spa, mature landscaping, and a very private setting. A charming English garden-inspired seating area adds another inviting place to relax, entertain, or enjoy a quiet morning outdoors. The property also includes a dedicated dog run for added convenience. Recent exterior improvements include freshly painted eaves and doors, adding to the home’s clean and well-maintained appearance. Additional features include a three-car garage with EV charger, a dedicated workspace in the garage, and a whole-house generator for emergency backup power. With four bedrooms, three baths, generous living spaces, a beautifully refreshed pool and spa, and exceptional outdoor areas, this Whisper Ranch home offers a wonderful blend of comfort, function, and California indoor-outdoor living.

36298 Mesa Vista Place, Yucaipa
$1,495,000
4 Beds ⋅ 5 Baths ⋅ OC26185539 MLS ⋅ Active Status
PANORAMIC MOUNTAIN AND VALLEY VIEWS | LIVES LIKE A SINGLE LEVEL | PRIVATE POOL & SPA | 4-CAR GARAGE | HUGE DRIVEWAY | CUL-DE-SAC STREET & MORE! Welcome to 34830 Olive Tree Lane. Perched on a quiet cul-de-sac, this stunning custom home delivers panoramic valley and mountain views along with an entertainer's layout that lives like a single story, every bedroom is on the main level. Step through the front courtyard into a light filled interior with soaring vaulted ceilings, a wide open floor plan, and walls of windows that frame the breathtaking scenery from nearly every room. A soft, neutral color palette flows throughout, complemented by luxury wood look vinyl plank flooring across the entire downstairs. The formal dining room and living room flank the entry, leading into a spacious great room designed for gathering. The completely remodeled kitchen is a showstopper, featuring a huge island with seating for seven, a sunny breakfast nook with front-row views, all new Forno stainless-steel appliances, a gas range and hood, microwave drawer, walk-in pantry, and soft close cabinetry with pots and pans drawers. The primary suite is tucked at the back of the home to soak in the best of the views, and its spa-like en-suite bath has been beautifully remodeled with a makeup counter, dual sink vanity, freestanding soaking tub, separate walk-in shower, and an oversized walk-in closet with custom organization. Two additional bedrooms share a convenient Jack-and-Jill bathroom on the same wing, while a fourth bedroom, full bathroom, and separate powder bath sit privately on the opposite side of the home, ideal for in-laws, guests, or a private home office. Upstairs, a massive loft currently set up as a game room offers a pool table, wet bar with counter seating, its own mini-split, and a powder bath...a true entertainer's dream. Outside is just as impressive: private pool and spa, outdoor BBQ with counter seating, and multiple patio and seating areas make the most of the expansive backyard's lush lawn, while the beautifully landscaped front yard adds to the home's curb appeal. Car enthusiasts and hobbyists will love the 4-car garage with Swiss track flooring and a mini-split A/C unit, plus a huge driveway that comfortably fits 9-10 vehicles. Topped off with energy-saving solar panels, this exceptional home offers luxury, privacy, and unforgettable views in one rare package. Welcome Home!

34830 Olive Tree, Yucaipa
$1,249,000
5 Beds ⋅ 4 Baths ⋅ CV26189602 MLS ⋅ Active Status

37191 Wildwood View, Yucaipa
$785,000
3 Beds ⋅ 2 Baths ⋅ IG26189241 MLS ⋅ Active Status
Welcome to a rare North Bench property offering the space, privacy and lifestyle buyers have been searching for! This well-maintained single-story home features 3 bedrooms, 2 bathrooms and approximately 1,708 square feet of comfortable living space on an expansive 1.14-acre lot. Inside, you’ll find spacious rooms, a welcoming fireplace, plantation shutters, crown molding, tile flooring and an updated walk-in shower. The kitchen is clean and functional, while offering the perfect opportunity for the next owner to personalize it to their style. Step outside and enjoy your own private retreat with an in-ground swimming pool, covered patio, mature landscaping and plenty of room for entertaining. The property also features RV parking, an attached two-car garage and generous usable land for animals, gardening, a workshop or future additional living space. With potential for accessory dwelling options, buyers can explore creating space for extended family, rental income or a private guest residence, subject to City, County, septic and other required approvals. Beautiful views, peaceful surroundings and over an acre of possibilities make this a truly special Yucaipa property

10222 Cherry Croft Dr., Yucaipa
$724,500
4 Beds ⋅ 3 Baths ⋅ IG26189012 MLS ⋅ Active Status
Welcome to 34293 Oakwood Place, a beautiful 4-bedroom, 3-bathroom home offering 2,203 square feet of living space at the end of a cul-de-sac in Yucaipa’s desirable Chapman Heights community. This home combines a sought-after location with exceptional indoor-outdoor living. Step inside to a spacious and versatile floor plan featuring separate formal living and dining room, providing the perfect setting for entertaining and special gatherings. The inviting family room features a cozy fireplace and opens to the kitchen, creating a comfortable central gathering place for everyday living. The kitchen features a center island with breakfast bar seating, offering additional prep space and a casual spot for meals and conversations. The thoughtfully designed floor plan includes a bedroom and full bathroom downstairs, providing flexibility for guests, a home office, or multi-generational living. Upstairs, you will find a versatile loft, that can serve as a play room, reading nook, or home office, along with a conveniently located laundry room. The spacious primary is a true retreat, featuring a walk-in closet and an en-suite bathroom with dual sinks and a relaxing soaking tub. Double doors open directly from the primary suite to your own private terrace showcasing gorgeous views - the perfect place to enjoy morning coffee, take in the scenery, or unwind at the end of the day. The backyard is a true highlight, designed for both entertaining and relaxation with a sparkling in ground pool and spa built in 2024, a Double-Decker porch with new ceiling fan and lighting plus plenty of room to roam on this great sized lot. Whether you’re hosting summer gatherings, relaxing poolside, or unwinding in the spa, this outdoor space is ready to be enjoyed. The home also features a 3-car garage and has benefited from several significant recent improvements, including a newer HVAC system, tank-less water heater, exterior paint, and vinyl fencing—providing added comfort, efficiency, privacy and peace of mind for the next owner. Conveniently located near the golf course, schools, shopping, dining, recreation, parks, and local amenities. Perfectly positioned to enjoy the best of Yucaipa living, this exceptional home stands ready to welcome its fortunate next owner.

34293 Oakwood, Yucaipa
$640,000
3 Beds ⋅ 3 Baths ⋅ HD26179388 MLS ⋅ Active Under Contract Status
Welcome to 11743 Adams St. Located within a clean and quiet cul-de-sac, this 2004 built POOL home!!! 3 Bedrooms, 2 1/2 bathrooms with a spacious 1,888sqft of living space, upgraded luxury vinyl plank flooring throughout, window coverings on all windows, front & back, good size kitchen with a dining area that looks out to your beautiful refreshing pool & backyard. Kitchen comes equip with black appliances. Laundry area is located behind accordion doors in the hallway. Front yard has lush landscape along with white Vinyl fencing, 3 car garage, RV parking & rain gutters. Backyard is where you can enjoy that staycation all year long. Whether you are basking in the sun in your sparkling pool or lounging under your extra large covered patio, you will be sure to enjoy. Property comes with a storage shed, dog run area and ample space to host any gathering your heart desires. If adventure is what you seek, we've got you covered. Located within 1.2 miles from your front door is the Yucaipa Regional and Community Park with hiking/biking trails, along with areas to enjoy a picnic and more. The entertainment doesn't stop there...continue a few more min and find eateries & local hot spots, just a perfect community. Home Leasing opportunity available if purchasing isn’t an option. You don't want to let this one pass you up! There is so much more than meets the eye.

11743 Adams Street, Yucaipa
$160,000
2 Beds ⋅ 2 Baths ⋅ 219151777DA MLS ⋅ Active Status
For showings call 760.625.6814 Discover this charming manufactured home in a sought-after 55+ community, where comfort meets stunning mountain views! This modern residence features an open floor plan, perfect for gatherings, with a spacious living area and a stylish kitchen with a central island. Enjoy a serene primary suite with a walk-in shower and the convenience of an indoor laundry room.Step outside to a covered patio, carport, and a yard ready for your gardening dreams. The community offers fantastic amenities like a pool, spa, clubhouse, and RV storage. Located just minutes from shopping, dining, and golf, this home is your ideal retreat for active adult living. Explore more at RanchoCalimesa.com

10320 Calimesa Boulevard Unit 46, Calimesa
$1,050,000
5 Beds ⋅ 4 Baths ⋅ IG26180680 MLS ⋅ Active Status
Welcome to this exceptional 5 bedroom, 4 bathroom residence offering luxury, comfort, and impressive living space in one of Yucaipa’s most desirable neighborhoods. This beautifully appointed home features a grand entry with soaring ceilings, an elegant formal dining room, and a spacious floor plan designed for both everyday living and entertaining. The heart of the home is the stunning kitchen, complete with custom cabinetry, a large center island, premium appliances, ample counter space, and an inviting dining area. The open-concept design flows seamlessly into the living spaces, creating the perfect setting for gatherings of any size. Retreat to the generously sized bedrooms, including a luxurious primary suite offering comfort and privacy. With four bathrooms, this home provides plenty of space and convenience for family and guests alike. Step outside to enjoy the beautifully landscaped backyard featuring a covered patio, outdoor entertainment area, and plenty of room to relax or host memorable events.

13385 Canyon Heights, Yucaipa
$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
$599,950
4 Beds ⋅ 3 Baths ⋅ 219151387DA MLS ⋅ Active Under Contract Status
Welcome home to 1165 Heritage Dr, an exquisite 4-bedroom, 3-bathroom retreat set on a sprawling lot located inside the gates at JP Ranch. From the moment you step inside, the open floorplan blends elegance with modern livability, highlighting thoughtful upgrades throughout that elevate everyday living. The heart of the home is the great room, where a chef-inspired kitchen boasts top-of-the-line appliances and a mounted 75'' TV serves as a dramatic focal point. The adjacent dining area completes the space, creating the perfect hub for entertaining and culinary creativity. Four generously sized bedrooms offer comfort and privacy, while three well-appointed bathrooms add a touch of everyday sophistication. Step outside to a backyard designed for relaxation and entertaining in equal measure. A large, covered patio sets the stage for al fresco dining, an outdoor kitchen invites culinary adventures, an above-ground pool and spa as well as the cozy firepit make this the ultimate spot to unwind under the stars. This home is also equipped with smart technology throughout. Control the lighting, temperature, and security with just a touch, bringing effortless, modern convenience to daily living. An added bonus: the home comes with a leased solar system that offers energy efficiency and lower utility costs, available for the new buyer to assume at close of escrow (subject to qualification with the solar provider). This is a fantastic opportunity to step into a home already set up for smart, sustainable living. Located within the highly sought-after JP Ranch community, 1165 Heritage Dr combines opulence, functionality, and modern innovation in one exceptional package. Schedule your private tour today and make this dream residence your own.

1165 Heritage Drive, Calimesa
$1,175,000
4 Beds ⋅ 3 Baths ⋅ IG26169038 MLS ⋅ Active Status
Tucked among beautiful mature trees and lush landscaping, this spacious single-story home offers privacy, flexibility, and incredible indoor-outdoor living just minutes from Oak Glen. The home features generously sized rooms, abundant storage, and a versatile bonus living area with its own bar, bedroom, bathroom, and additional space—ideal for extended family, guests, a mother-in-law suite, game room, or entertaining area. Step outside and enjoy a backyard that truly feels like a private retreat. The sparkling pool, dedicated BBQ area, outdoor chimney, and breathtaking views create the perfect setting for relaxing or entertaining. A sunroom provides a peaceful place to enjoy the sunrise, while the full-size tennis court offers recreation right at home. Additional highlights include multiple storage buildings, a three-car garage, RV parking, and plenty of room for all your hobbies, vehicles, and equipment. With its secluded setting, impressive amenities, and convenient location, this one-of-a-kind property offers space, comfort, and endless possibilities.

36268 Highland Ave, Yucaipa
Start Your Search

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.