Yucaipa/Calimesa/Oak Glen (269) Homes with Garage Faces Side Parking features

Welcome to the picturesque region of Yucaipa, Calimesa, and Oak Glen, nestled in the heart of San Bernardino County, California. This charming area is renowned for its stunning natural beauty, friendly communities, and a plethora of outdoor activities that make it an ideal place to call home.

Yucaipa, with its vibrant downtown and family-friendly atmosphere, offers a delightful blend of modern conveniences and small-town charm. You'll find an array of shops, restaurants, and parks that cater to all ages. Just a stone's throw away, Calimesa boasts a serene environment, perfect for those seeking a quieter lifestyle while still enjoying easy access to local amenities. Meanwhile, Oak Glen is famous for its apple orchards and breathtaking mountain landscapes, providing a perfect escape for nature lovers and outdoor enthusiasts.

One of the standout features of homes in this region is the side-facing garages, which not only enhance curb appeal but also provide ample space for parking and outdoor activities. These thoughtfully designed homes offer a practical solution for families and individuals alike, ensuring that vehicles are easily accessible while maintaining a clean and organized front yard.

Whether you’re looking for a cozy retreat with a view, a spacious family home, or a charming cottage, Yucaipa, Calimesa, and Oak Glen have something for everyone. Come explore this enchanting region where community spirit thrives, and your dream home awaits!

Newest Yucaipa/Calimesa/Oak Glen (269) Homes with Garage Faces Side Parking features

$599,000

5 Beds ⋅ 3 Baths ⋅ IG26161154 MLS ⋅ Active Status

Nestled in the highly desirable upper Yucaipa area, this beautifully maintained custom tri-level home offers exceptional curb appeal, mountain views, and a spacious lot of over 1/4 acre. A long driveway, mature landscaping, RV parking, and a two-car attached garage create an impression while providing ample space for vehicles, toys, and guests. Inside, you'll find a light-filled interior featuring tasteful neutral colors, fresh interior paint, new carpet, and classic plantation shutters. The thoughtfully designed floor plan offers flexibility for a variety of lifestyles. The main level serves as the heart of the home with an inviting living room, formal dining area, and well-appointed kitchen—perfect for everyday living and entertaining. The lower level features a versatile bedroom complete with a wet bar, making it ideal as a guest suite, family room, game room, or private home office. A convenient laundry room and updated half bath complete this level. Upstairs, retreat to the spacious primary suite featuring a private balcony where you can enjoy peaceful mornings and beautiful views. The large primary bath includes dual vanities, a soaking tub, separate shower, and generous closet. Three additional bedrooms and a guest bathroom provide plenty of room for family and guests, with the guest bath also beautifully remodeled. Step outside to enjoy the expansive yard with lush lawn, mature trees, attractive landscaping, and plenty of room to entertain, garden, or even add a pool. The combination of privacy, usable outdoor space, and scenic surroundings makes this property truly special. With its custom design, flexible floor plan, tasteful updates, oversized lot, RV parking, and sought-after upper Yucaipa location, this home offers the perfect blend of comfort, functionality, and timeless appeal.

11666 Madison Street, Yucaipa

$725,000

5 Beds ⋅ 3 Baths ⋅ IG26154327 MLS ⋅ Active Under Contract Status

STOP SCROLLING—THE HOME EVERYONE WANTS JUST HIT THE MARKET! Golf course views? Check. Nearly 3,300 square feet? Check. Five bedrooms, three full bathrooms, multiple living spaces, and one of Chapman Heights' most sought-after floor plans? Check, check, and check! If you've been waiting for the perfect combination of size, location, and versatility in Yucaipa, this is the one that deserves the top spot on your must-see list. Welcome to 11967 Southwind Way, where luxury, space, and functionality come together in the highly sought-after Chapman Heights community. Perfectly positioned along the fairways of the Yucaipa Valley Golf Course, this stunning home offers breathtaking golf course views and room for everyone to spread out and enjoy. Step inside to discover three separate living spaces, including a formal living room, an inviting family room that opens to the kitchen, and an oversized upstairs loft that's ready to become your dream game room, home office, movie room, gym, or kids' playroom. With nearly 3,300 square feet, you'll never feel short on space. The thoughtfully designed floor plan features five spacious bedrooms and three full bathrooms, including a highly desirable downstairs bedroom and full bathroom that's perfect for guests, multi-generational living, or a private home office. The kitchen offers an abundance of cabinetry, white tile countertops, stainless steel appliances, and plenty of prep and storage space, all conveniently located adjacent to the indoor laundry room. Upstairs, retreat to the expansive primary suite where you'll wake up to gorgeous golf course views. A charming farmhouse-style sliding door provides privacy as you enter the spacious primary bathroom featuring dual sinks, a walk-in shower, soaking tub, and an oversized walk-in closet. One of the standout features of this home is the unique garage configuration. Enjoy the convenience of a two-car garage plus a separate one-car garage—ideal for extra vehicles, a workshop, golf cart storage, home gym, or additional storage space. Homes with this combination of size, views, location, and versatility rarely become available in Chapman Heights. Whether you're entertaining guests, accommodating a growing household, or simply looking for the perfect place to call home, 11967 Southwind Way checks all the boxes. Don't miss your opportunity to own one of Chapman Heights' most desirable floor plans with spectacular golf course views!

11967 Southwind, Yucaipa

$285,000

2 Beds ⋅ 2 Baths ⋅ SW26149200 MLS ⋅ Active 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. As an added bonus, the seller is offering the option to keep the home partially furnished, making your move-in even easier!

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

$895,000

4 Beds ⋅ 3 Baths ⋅ IG26122820 MLS ⋅ Active Status

Experience elevated living in Upper North Yucaipa. This custom-built home is a place where mornings begin with soft mountain light and evenings settle into quiet sunsets over the valley. With 3,077 sq ft of thoughtful design, this 4-bed, 3-bath retreat was crafted for comfort, connection, and the kind of living that brings generations together. The great room is the heart of the home — warm, open, and anchored by a beautiful fireplace. It flows effortlessly into the chef’s entertainer’s kitchen, where family gatherings feel natural, and conversations linger. With two full primary suites, this home is perfectly suited for multi-generational living, offering privacy, independence, and comfort for everyone under one roof. The main suite’s dual walk-in closets add a touch of everyday luxury. Enjoy the convenience of a whole house fan system, 36 inch doorways throughout with no thresholds and a wheel-in accessible shower. Step outside to the large covered patio, where mornings start with coffee overlooking the mountains and evenings end with golden skies. The 16,117 sq ft lot gives you room to breathe, with a 2-car attached garage and RV parking on both sides of the property with full hook-ups (50-amp, water, sewer) on the west side and partial hook-ups on the east side. When you’re ready to explore, you’re just minutes from Oak Glen Village, close to mountain and desert resorts, the Yucaipa Regional Park, and convenient shopping. This is more than a home — it’s a lifestyle rooted in views, space, and the quiet beauty of Upper North Yucaipa, designed to bring families together.

35102 Persimmon, Yucaipa

$599,000

3 Beds ⋅ 2 Baths ⋅ IG26127326 MLS ⋅ Active Status

Welcome to 13348 5th Street in Yucaipa, where modern upgrades, functional living space, and a large lot come together to create the perfect place to call home. This beautifully remodeled single-story residence offers over 1,600 square feet of living space with 3 bedrooms, 2 full bathrooms, and a versatile floor plan designed for today's lifestyle. Step inside to discover an extensively renovated interior featuring gorgeous laminate wood flooring, recessed lighting, and a stunning open-concept kitchen that serves as the heart of the home. The kitchen boasts white shaker cabinetry, quartz countertops, subway tile backsplash, black stainless steel appliances, and an eat-at bar that opens seamlessly to the spacious living area, making it ideal for entertaining family and friends. The bedrooms are generously sized, while an additional bonus room provides incredible flexibility and can serve as a secondary family room, game room, home office, or even a potential fourth bedroom. Both bathrooms have been tastefully updated with upgraded vanities, modern fixtures, and beautiful tile work. The spacious primary suite includes dual sinks and a large walk-in shower, creating a private retreat you'll love coming home to. Additional interior features include indoor laundry and an abundance of natural light throughout. Situated on a lot of over a quarter acre, the exterior offers endless possibilities. A circular driveway provides excellent curb appeal and convenience, while the oversized garage is both extra deep and extra wide, offering ample room for vehicles, storage, hobbies, or a workshop. Need even more space? The detached storage building has been insulated and drywalled, making it an ideal flex space for a home office, gym, studio, workshop, or hobby room. The property also features extensive concrete flatwork, abundant parking, RV parking, and plenty of room for all your toys, trailers, boats, and recreational vehicles. Combining modern updates, flexible living spaces, and exceptional parking and storage options, this move-in-ready Yucaipa home offers the space, versatility, and upgrades that today's buyers are searching for. Don't miss your opportunity to make it yours!

13348 5th, Yucaipa

$1,485,000

3 Beds ⋅ 3 Baths ⋅ PW26105840 MLS ⋅ Active Status

78,843 square foot giant lot with a front and back entrance with two 40 x 60 all steel fully permitted warehouses with tons of storage on the lot Can drive heavy trucks and equipment in from the East and West entrances both with wide gates with reinforced heavy-duty concrete with over 100 yards of driveway space along with true RV parking and RV sewer hookup and water! Perfect for your race cars, campers, toys, automotive storage The roll up doors are extra tall and the warehouses are built like tanks. So much storage. Live in the residential home that is a 3-bedroom 3 bath complete with a bathroom in the Man Cave Garage. The garage is spacious and the garage door opens up to the lot for additional storage. So much you can do here. The grounds are well maintained and there is even an exotic rare catus garden. The warehouses have steel roofs and the over 15-foot steel doors are perfect for all of your storage needs. There is even an existing car lift. The house is the perfect place to have an onsite caretaker to watch over all of your stuff. Do not pay for RV storage ever again The house has an incredible open floor plan with a great kitchen with granite counter tops. Lots of storage and the neighborhood is fantastic. You could do almost anything with this giant lot. A great place to call home and store your boat and camper at the same time! So close to downtown Yucaipa. Close to the golf course, wilderness park and all of your favorite little coffee shops and walking trails. In between Thermal and the mountains are calling. Just a quick drive up the back side to Lake Arrowhead or Running Springs. Perfectly situation close to the Palm Springs airport or Ontario International airport and even the private Chino airport. Solid roof, great plumbing and good electrical. No need to look any further. You have found the perfect place to call home and work at the same time! Build that ADU you have always dreamed of or plant that giant garden. Room for the kids to play and a great space to come home to. Mint condition. The owner has kept this home in superior condition. Come on over and stay awhile and enjoy our Mountain view! Have your morning coffee out on the back porch or sit out under the front porch for pure serenity and peace. A property like this only comes up once in a great while. You can almost never find a beautiful home complete with giant 40 x 60 all steel warehouses that are FULLY PERMITTED. You could even store your planes here. Excellent investment.

12681 Bryant, Yucaipa

$699,000

3 Beds ⋅ 2 Baths ⋅ IG26079373 MLS ⋅ Active Under Contract Status

Perched high above the valley in the heart of Oak Glen, this remarkable hilltop retreat offers the kind of panoramic views most people only experience on vacation. From sunrise over the mountains to sparkling city lights at night, every window frames a breathtaking piece of Southern California's natural beauty. Set on approximately 1.66 acres, this custom-built home was thoughtfully designed to embrace its surroundings, blending comfort, privacy, and unforgettable scenery. The open-concept living spaces invite the outdoors in, while expansive windows capture miles of rolling hills, mountain vistas, and changing skies throughout the day. Imagine enjoying your morning coffee as the sun rises over the valley, hosting friends beneath a canopy of stars, or simply unwinding in complete tranquility after a busy day. This is more than a home—it's a lifestyle rarely available and impossible to replicate. Located in the highly desirable Oak Glen community, known for its apple orchards, seasonal charm, hiking trails, and small-town atmosphere, this property offers the perfect balance of peaceful mountain living with convenient access to nearby shopping, dining, and commuter routes. Whether you're searching for a full-time residence, weekend retreat, or private sanctuary with unforgettable views, this is an opportunity to own one of Oak Glen's most captivating settings.

38736 Oak Glen Road, Oak Glen

$1,225,000

4 Beds ⋅ 3 Baths ⋅ IG26061388 MLS ⋅ Active Status

Over two acres in Oak Glen with a single story 2013 build, an attached four car garage, stables, and a separate guest home. Welcome to Snow Line Ranch! Located on a private street in the picturesque town of Oak Glen, this custom built home sits directly across from the protected Wildlands Conservancy. You approach the property and are greeted by stunning mountain views. This land was previously owned by Kevin Costner. Enter the home past the large front porch, or directly from the oversized four car garage (est. over 1200 sq ft) , which features even more storage space in a dedicated loft overhead. The great room in the center is the heart of the home. A sizable living area features a rock wall with a wood burning stove. This opens up to a foyer, dining, and a large kitchen. All of these rooms are filled with natural light from large double pane windows. High end touches included a conventional double oven, a walk in pantry, excellent counter space, and the farmhouse sink. You may actually enjoy dishes with this view! The spacious primary suite is off of the kitchen, with it's own walk-in closet and a sizable bath. There is a large shower and a soaking tub. There are three additional bedrooms opposite the family room, all with sizable closet space. One features French doors, and is currently in use as a home office. This home even has a basement (estimated at 432 square feet, and not included in the online square footage). Heading outside, there is a 2023 Park Model manufactured home with two additional bedrooms, kitchen, living space, and even laundry hookups (estimated at 392 square feet, and not included in the online square footage). With it's own permanent water, power and septic hookups, this is perfect for a home office, guest space, or extended live-in family. This private location on Raspberry means serene country living without the inconveniences of being too far off the grid. We are only 15 minutes from Stater Brothers Market in Upper Yucaipa, and just around the corner from local Oak Glen dining. There is a paid solar system - owners total Edison power bill in 2025 was less that $100. Sellers use Starlink for internet. The Generac propane generator and the Oak Glen Domestic Water Company Shares are also included in the sale.

11821 Raspberry, Oak Glen

$1,094,400

3 Beds ⋅ 3 Baths ⋅ IV26017542 MLS ⋅ Active Status

Country living meets modern convenience in the charming small-town atmosphere of Yucaipa, California. This exceptional homesite is nestled on an estimated ½-acre plus lot in a quiet cul-de-sac above Yucaipa Creek, offering stunning mountain and valley views. This home features 3,147 SQFT, 3 spacious bedrooms, 3 bathrooms, and a 3 car garage. Designed with entertaining in mind, the open floor plan flows seamlessly from the large kitchen to the great room, connecting the front courtyard with a covered rear patio for year-round indoor-outdoor living. The chef-inspired kitchen includes: A large quartz island, Stainless Steel Appliances Package, including: 40" Built-in Refrigerator, 48" Range with Double Ovens, 48" hood, Wall Oven, Microwave, and Dishwasher. Interior Included Features 7 1/4" Baseboards, Wide entry Door, Tall Decorative Interior Doors, 10 Foot ceilings in main living areas and Primary Bedroom. The primary suite is a luxurious retreat, featuring: A sliding barn door leading to the spa-like bathroom, A Roman Tub, large walk-in shower with Bench seating and Designer Decorative Tile Walls, an oversized walk-in closet, Additional highlights: Owned solar panels for energy efficiency, High-quality dual-pane windows, Top and bottom insulated attic, and No HOA. RV-accessible side yard with clean-out installed. Expansive Vinyl privacy fenced backyard with room for a pool ADU, workshop, or anything else you envision. Pool can be built with the home if using builders pool company. Please note: Photos shown are of the model home, Lot 10 is a quick close home with lots of upgrades. Our most popular Plan 2 is almost sold out lot 10 is the only one left...Last one Don't miss out

35873 Wildwood Crest Drive, Yucaipa

$2,798,000

3 Beds ⋅ 4 Baths ⋅ IV25158712 MLS ⋅ Active Status

Welcome to Vista Dhome, an extraordinary monolithic dome residence situated atop a breathtaking mountain in Yucaipa, California. Spanning 3,895 square feet of thoughtfully designed living space, this unique home rests on 42 acres of pristine mountain top land at an elevation of 3,800 feet. Here, you’ll experience true 360-degree panoramic views that sweep across the landscapes of Yucaipa, Calimesa, Cherry Valley and the rugged majesty of the surrounding mountains. From your vantage, gaze over the San Bernardino National Forest, Lake Perris, and Lake San Jacinto. On a clear day, your eyes can wander as far as Palm Springs and even the distant outline of Catalina Island. This setting delivers unparalleled vistas and a sense of tranquility that is simply unmatched, ideal for those seeking harmony between contemporary comfort and raw natural beauty. Nestled in the foothills of the San Bernardino Mountains, Vista Dhome offers both peaceful seclusion and convenient access to local amenities. The property is located near scenic parks, hiking and biking trails, shopping centers, and top-rated schools, ensuring a lifestyle that blends relaxation with opportunity. *Monolithic Dome Design: The home's innovative dome shape provides exceptional energy efficiency, structural integrity, and a striking architectural profile. *Expansive Living Space: The residence features an open-concept floor plan illuminated by natural light, soaring ceilings, and elegant finishes throughout. *Resort-Style Pool and Spa: Enjoy an exotic swimming pool complete with a dramatic waterfall and a hidden grotto, creating an atmosphere of tropical luxury. Relax in the inviting in-ground spa, or retreat to the additional above-ground spa perched on the expansive viewing deck, perfect for soaking in the breathtaking mountain vistas. *Modern Kitchen: The gourmet kitchen is equipped with premium appliances, spacious granite countertops, ample cabinetry, and a central island perfect for both casual meals and entertaining *Outdoor Retreat: With 42 acres to explore, the property includes beautifully landscaped gardens, a welcoming patio, and abundant room for outdoor gatherings or peaceful evenings under the stars. *Energy Efficiency: Dome construction, modern HVAC system, dual-pane windows, Solar for the pool and smart home features combine for impressive comfort and sustainability. Vista Dhome isn't just a home; it's a one-of-a-kind mountaintop retreat.

13600 Diamond Point Drive Unit 1, 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.