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

38136 Butterfly Court, Yucaipa
$1,099,000
4 Beds ⋅ 4 Baths ⋅ CV26228782 MLS ⋅ Active Status
Welcome to this stunning 4-bedroom, 3-bathroom home nestled on a quiet cul-de-sac, offering the perfect blend of elegance, comfort, and breathtaking views. A grand entry welcomes you into a light-filled interior featuring soaring ceilings, abundant natural light, and an open-concept floor plan designed for modern living. Step outside to the expansive rear balcony and take in the scenic views, making it the ideal place to enjoy your morning coffee or relax at sunset. The private backyard is a true retreat, complete with a sparkling pool and spa, creating the perfect setting for outdoor entertaining and year-round enjoyment. With four generously sized bedrooms, three full bathrooms, a desirable cul-de-sac location, and exceptional indoor-outdoor living spaces, this remarkable home offers the perfect combination of luxury and functionality.

38136 Butterfly Court, Yucaipa
950 California Unit 9, Calimesa
$130,000
2 Beds ⋅ 2 Baths ⋅ IG26184911 MLS ⋅ Active Status
Relax, unwind, and connect in Calimesa’s premier 55-plus community. This spacious double-wide home features two bedrooms, two bathrooms, dual-pane windows throughout, and an updated kitchen with a refrigerator, stove, microwave, dishwasher, washer, and dryer. The bright living space offers a ceiling fan, newer central HVAC for year-round comfort, and plenty of cupboards and shelves for storage. Exterior amenities feature a covered carport that fits two cars, a private storage shed, exterior security lighting, a video doorbell, and a small rose garden in front of the home with automatic drip irrigation. Community perks include mountain views, park-wide security cameras, an active clubhouse with a fireplace and full kitchen, a swimming pool, sauna, shuffleboard court, and pet-friendly grounds with RV storage. Residents regularly gather for holiday get-togethers, card games, and meetings in the clubhouse, creating opportunities for socializing and neighborly support while allowing everyone to maintain their own routines and independence. Conveniently located near I-10 freeway access in a quiet foothill setting, with nearby shopping, services, and parks, plus easy drives toward Redlands, Yucaipa, and surrounding outdoor areas. Designed for secure, carefree living in this tranquil 55-plus community.

950 California Unit 9, Calimesa
963 Bryant, Calimesa
$950,000
4 Beds ⋅ 3 Baths ⋅ PW26225165 MLS ⋅ Active Status
Welcome to this beautifully updated ranch-style home on 1.92 acres! Expanded in 2018, this 4,133 sq ft single-story home offers 4 bedrooms and 3 baths, including two primary suites or an in-law setup, plus custom closet shelving throughout. Enjoy vaulted ceilings, crown molding, recessed lighting, new flooring, and fresh paint. The remodeled primary bath features a walk-in shower, rainfall showerhead, dual sinks, and quartz counters. Major upgrades include a 2018 roof, two HVAC units with all-new ductwork, dual-pane windows, PEX plumbing, a water softener, a whole-house fan, and solar. Outside, you’ll find a pool and spa with new equipment, new front and covered back patios, new sprinklers, a 115 ft retaining wall, and a backyard ready for your vision. There’s a 960 sq ft workshop, an oversized 2-car garage, a wraparound driveway, and RV parking!

963 Bryant, Calimesa
34835 Elmwood Lane, Yucaipa
$799,999
4 Beds ⋅ 3 Baths ⋅ IG26222175 MLS ⋅ Active Status
Welcome to the EVERYTHING house! Where luxury meets entertainment, and every day feels like a vacation! Nestled on a quiet cul-de-sac near the highly desirable Chapman Heights community, this stunning home truly has it ALL — with NO HOA and OWNED SOLAR! Step into your own private backyard resort, complete with a sparkling pool, spa, thrilling waterslide, grotto, cascading waterfall, TWO fire pits, and a covered patio perfect for entertaining year-round. Add in a FOUR-car garage and gated side parking, and you'll quickly realize this home checks boxes you didn't even know you had! And that's just the OUTSIDE! Inside, you'll discover four spacious bedrooms, three bathrooms, two inviting living areas, and beautiful upgrades throughout. Need even more flexibility? The enclosed loft, complete with stylish barn doors for privacy, offers the perfect OPTIONAL FIFTH BEDROOM, home office, fitness studio, or creative retreat! Whether you're hosting summer pool parties, enjoying cozy evenings around the fire, or simply relaxing in your own private paradise, this home was made for living life to the fullest. This isn't just a home. It's THE home. The one everyone wants to be at, where weekends feel like vacations and memories are made for years to come. With resort-style amenities, owned solar, generous parking, versatile living spaces, and the freedom of no HOA, this rare opportunity is one you won't want to miss! Call us today to schedule your private showing and submit your offer!

34835 Elmwood Lane, Yucaipa
11869 Greenbluff Way, Yucaipa
$674,900
3 Beds ⋅ 3 Baths ⋅ IG26216697 MLS ⋅ Active Status
Welcome to this beautifully UPDATED AND REMODELED SINGLE STORY POOL HOME in the sought-after Chapman Heights community, located near golf courses and the scenic foothills of Yucaipa. This home offers 3 bedrooms, 3 bathrooms, and 2,150 square feet on a 9,293 square foot lot. High ceilings, crown molding, ceiling fans, and a light, soft color palette create an airy feel throughout. Recent updates include NEWER FLOORING THROUGHOUT, FULLY UPDATED KITCHEN WITH NEW APPLIANCES, CABINETRY, COUNTERS, LIGHTING, etc. UPDATED BATHROOMS, FRESH INTERIOR PAINT (2026) AND EXTERIOR PAINT (2024), making this home truly turnkey. The open floor plan connects the kitchen, dining area, and living room. The new kitchen includes all appliances, a center island, and a pantry, and opens to the living room with its cozy fireplace. The dining area sits adjacent to the kitchen. A versatile room offers the option of a formal living room, flex space, home office, or create a fourth Bedroom. The spacious primary suite features private access to the pool patio, a large walk-in closet, and a spa-like bathroom with a separate shower and tub. A front guest bedroom has its own private bathroom, and a hall bathroom is conveniently located near the third guest bedroom. Additional highlights include a separate laundry room and a three-car garage with abundant storage space. The backyard is designed for easy enjoyment, with a sparkling pool and spa and drought-tolerant landscaping, plus a blank-canvas hillside behind the pool just waiting for your horticultural imagination to bloom!

11869 Greenbluff Way, Yucaipa
35353 Cabrini Drive, Yucaipa
$975,000
5 Beds ⋅ 3 Baths ⋅ IV26219092 MLS ⋅ Active Status
WELCOME HOME TO YOUR OWN PRIVATE RESORT AND ENTERTAINER'S DREAM HOME!! Discover this exceptional custom home where spacious interiors, distinctive features, and an incredible outdoor retreat come together to create a truly special Southern California lifestyle. This two-story property features 5 bedrooms, 3 bathrooms, a 4-car garage, and a resort-style pool & spa on a large lot with NO HOA. Step inside to hardwood floors and a welcoming staircase that lead into generous living spaces. The formal living and dining areas feature cathedral ceilings and a fireplace, creating a welcoming setting for entertaining and special occasions. The kitchen features granite countertops and tile flooring, while the family room offers a second fireplace, oak cabinetry, a wet bar, wine cooler, surround sound, and direct access to the backyard—perfect for everyday living and hosting guests. A convenient downstairs bedroom and 3/4 bathroom provide excellent flexibility for guests or home office. Spacious laundry room with hookups and storage. A central vacuum system adds everyday convenience throughout the home. Upstairs, the primary suite offers a walk-in closet with a mirrored ceiling and dedicated vanity. The primary bathroom features a soaking tub and shower equipped with multiple sprayers for a spa-inspired experience. The four-car garage features durable epoxy flooring, providing ample room for vehicles, storage, or a versatile studio space with mirrored walls and a ballet stretch bar, ideal for a home gym or creative pursuits. OUTSIDE, YOUR BACKYARD OASIS AWAITS! The heated pool and spa feature a cascading waterfall spill, multicolor underwater lighting, and a pool vacuum system. Whether hosting summer parties or unwinding beneath the stars, this outdoor setting delivers an unforgettable experience. A large trex deck and park-sized gazebo create inviting spaces for barbecues, birthdays, celebrations, and relaxed evenings. You will enjoy the expansive grounds with refreshed landscaping and a gated dog run. Imagine weekends spent lounging poolside, gathering beneath the gazebo, or unwinding in the spa after a long day. With its generous accommodations, versatile spaces, and exceptional outdoor amenities, this property offers room to entertain, recharge, and enjoy life your way. A HOME THIS SPECIAL DESERVES TO BE EXPERIENCED IN PERSON! Photos can only tell part of the story. Come tour the home, and appreciate its unique features. Welcome Home!

35353 Cabrini Drive, Yucaipa
34111 Wildwood Canyon Unit 108, Yucaipa
$180,000
3 Beds ⋅ 2 Baths ⋅ DW26219227 MLS ⋅ Active Status
Welcome to Wildwood Canyon Estates, a welcoming all-age community in the beautiful city of Yucaipa! This 3-bedroom, 2-bathroom manufactured home offers a comfortable living space, a functional floor plan, and a covered parking structure. Inside, you’ll find a spacious living area, a generously sized primary bedroom, and two additional bedrooms that offer flexibility for your everyday needs. The layout provides a great opportunity for buyers looking to personalize a home to match their own style and preferences. Step outside and enjoy your own private yard, offering space for outdoor gatherings, gardening, or simply relaxing. It’s a wonderful opportunity to enjoy outdoor living without the upkeep of a large property. Wildwood Canyon Estates offers an impressive selection of community amenities, including two swimming pools, a clubhouse, a playground, a dog park, a basketball court, walking paths, and RV storage. Conveniently situated near local shopping, dining, and freeway access, this location makes everyday living easy. Schedule your private showing today! Buyer must obtain park approval. Buyer to verify space rent, community rules, amenities, and property condition.

34111 Wildwood Canyon Unit 108, Yucaipa
360 Canyon View, Calimesa
$773,000
4 Beds ⋅ 2 Baths ⋅ IG26215426 MLS ⋅ Active Status
Welcome to this single-story bungalow offering comfortable proportions, practical living, and inviting outdoor enjoyment. The one-level layout provides an easy flow for everyday routines, relaxed evenings, and time spent together. Central cooling helps keep the interior comfortable through warmer seasons, while the private pool creates a refreshing setting for sunny afternoons, casual gatherings, or quiet weekends at home. A two-car garage adds convenient covered parking and useful storage possibilities. The wood-shingle roof and classic bungalow architecture give the residence a distinctive residential profile. Daily essentials and neighborhood destinations are within reach. With its spacious footprint, four-bedroom versatility, central cooling, garage, and pool, this Calimesa home presents an appealing opportunity for buyers seeking a residence with both indoor function and outdoor leisure. Explore the possibilities at 360 Canyon View Dr and imagine how its flexible spaces could complement your lifestyle. This unique property is large enough for horses and zoned. Schedule your private showing today. The other strong points on this well cared for home is newer roof, newer windows, exterior paint and also an upgraded panel set up for your electric car as you wish.

360 Canyon View, Calimesa
13668 Canyon View Drive, Yucaipa
$949,000
5 Beds ⋅ 3 Baths ⋅ IG26214270 MLS ⋅ Active Status
Welcome to single-story resort living in Whisper Ranch. This five-bedroom, two-and-a-half-bath home offers 2,904 square feet on a 10,000-square-foot lot, with gated RV parking and a backyard made for entertaining. High ceilings, natural light, and beautiful arched windows greet you in the formal living and dining areas. Hardwood floors run through the main living spaces, while the bedrooms feature new carpet and ceiling fans. Plantation shutters, crown molding, recessed lighting, and surround-sound speakers add thoughtful touches throughout the main living areas. The family room opens to the kitchen, with a stone-faced fireplace as its focal point. The kitchen features an island, granite countertops, stainless steel appliances that are all within three years old, a Wi-Fi-connected smart oven, a bay-window seat, and pull-out pantry drawers. A split floor plan places the primary suite on one side of the home and the guest bedrooms on the other. The remodeled primary bath features a clawfoot tub and walk-in shower. Outside, enjoy a PebbleTec pool with a waterfall and slide, a covered entertaining area with an outdoor TV, barbecue, sink, refrigerator, and fireplace, plus a separate fire pit and gazebo. Additional features include dual HVAC systems, a tankless water heater, water softener, epoxy garage flooring, garage cabinets, two sheds, and a washer and dryer that are only a few months old. The exterior was painted within the last two years. With its inviting interiors, thoughtful upgrades and resort-style backyard, this Whisper Ranch home makes everyday living feel like a getaway. Welcome to your everyday escape.

13668 Canyon View Drive, Yucaipa
35679 Lynfall Street, Yucaipa
$879,000
5 Beds ⋅ 3 Baths ⋅ IG26208836 MLS ⋅ Active Status
5-bedroom, 3-bathroom home located in a cul-de-sac. Property features a 40-foot driveway, 3-car garage, and gated motorhome parking. There is a separate Living room and cozy family room with a fireplace. Ceilings fans through the home with a whole house fan included. The backyard has landscaping, BBQ island, a variety of fruit trees, an above-gound pool, a dedicated garden area, and a permnanent shed.

35679 Lynfall Street, Yucaipa
11620 Calvin Street, Yucaipa
$325,000
2 Beds ⋅ 1 Baths ⋅ IG26166490 MLS ⋅ Active Status
Welcome to Sun Park I, a highly desirable 55+ active-adult community in beautiful Upper Yucaipa! This charming and exceptionally well-maintained single-story home offers two bedrooms, one full bathroom, a spacious living room, and abundant natural light throughout. The inviting kitchen features tile countertops and an eat-in dining area. Recent improvements include new carpet, fresh interior and exterior paint, newer dual-pane windows, and a newer composition roof. Enjoy the screened sunroom, separate laundry room with a utility sink, and a low-maintenance backyard with mature shade trees and privacy hedging. The single-car garage includes a workbench and additional storage, while rain gutters add everyday convenience. The low HOA provides wonderful amenities, including a swimming pool, clubhouse, putting green, and scenic walking paths. Ideally located near shopping, golf courses, parks, trails, the regional park, community center, and performing arts center—all surrounded by beautiful mountain views. With low property taxes and an easy-care lifestyle, this lovely home is ready to welcome its next owner!

11620 Calvin Street, Yucaipa
34354 Sherwood, Yucaipa
$689,900
4 Beds ⋅ 3 Baths ⋅ PW26203129 MLS ⋅ Active Status
Beautiful Chapman Heights 2200+ sq/ft pool home on a large 8,844 sq ft lot located on a quiet cul-de-sac! This 4-bedroom, 3-bath home features a bright, open floor plan with soaring ceilings, plenty of natural light and newer paint throughout. The kitchen and family room with fireplace overlook the private backyard featuring a covered patio, sparkling pool and spa—perfect for entertaining. Downstairs offers a bedroom and full bath with walk-in shower, ideal for guests or extended family. Upstairs you’ll find three additional bedrooms, two baths and a spacious loft perfect for an office, game room or second living area. The primary suite features a private balcony overlooking the backyard with beautiful sunrise views. Large 3-car garage, leased solar and plenty of storage complete this great Chapman Heights home!

34354 Sherwood, 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.

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