Yucaipa/Calimesa/Oak Glen (269) Homes with Two Levels Stories

Welcome to the enchanting region of Yucaipa, Calimesa, and Oak Glen, nestled in the heart of Southern California! Known for its picturesque landscapes, charming neighborhoods, and a community spirit that welcomes all, this area offers an idyllic setting for families and individuals alike. With the majestic San Bernardino Mountains as a backdrop, residents enjoy a perfect blend of natural beauty and suburban comfort.

Yucaipa boasts a rich history and a vibrant downtown area filled with boutique shops, delightful eateries, and local events that foster a sense of community. Just a stone’s throw away, Calimesa offers a tranquil atmosphere with its sprawling parks and golf courses, perfect for outdoor enthusiasts. Meanwhile, Oak Glen is renowned for its apple orchards and seasonal festivals, making it a delightful retreat for nature lovers and families looking to create lasting memories.

If you're in the market for a home, you'll find a variety of options, including stunning two-story residences that provide ample space for living, entertaining, and enjoying life. These homes often feature open floor plans, modern amenities, and spacious backyards, making them ideal for families or anyone who appreciates a little extra room to breathe. With multiple levels, these homes offer the perfect balance of privacy and togetherness, allowing for both cozy family gatherings and peaceful retreats.

Whether you’re drawn to the scenic beauty, the rich community vibe, or the exceptional housing options, Yucaipa, Calimesa, and Oak Glen are waiting to welcome you home! Explore this charming region today and discover the perfect place to create your next chapter.

Newest Yucaipa/Calimesa/Oak Glen (269) Homes with Two Levels Stories

$589,000

3 Beds ⋅ 3 Baths ⋅ IG26214517 MLS ⋅ Active Status

Welcome to 33410 Wallace Way, a highly upgraded smart home in the desirable Aberdeen community of Chapman Heights, offering gorgeous views from the backyard. With nearly 2,300 sq ft of living space, this 3-bedroom, 2.5-bath home also includes an attached two-car garage. The formal living and dining rooms flow into the kitchen, now finished with new quartz countertops, and into the family room, where a fireplace, large windows, and Milgard French doors open to the backyard. Outside, a large insulated covered patio is ready for entertaining. Concrete and stone pathways run along both sides of the yard, and wrought iron fencing across the back keeps the views and mature landscaping in full sight. Upstairs you'll find a bonus loft, two guest bedrooms, a guest bath, a laundry room, and a spacious primary suite with beautiful views of the city below. The primary bath has a walk-in shower, soaking tub, dual sinks, a large walk-in closet, tile flooring, new light fixtures, and heated mirrors. Recent upgrades include LVP flooring upstairs, Andersen windows on the first floor, a whole house fan, three ceiling fans, exterior paint (2018), HVAC (2020), rain gutters (2020), water heater (2022), interior paint (2023), multiple smart home features, and a whole-house GFCI (2026). As a bonus, the HOA maintains the front yard landscaping. The community also offers walking trails and a playground, and the Yucaipa Valley Golf Course is just around the corner. Local schools, shopping, grocery stores, restaurants, gyms, and so much more are all close by. Don't miss this one!

33410 Wallace, Yucaipa

$809,000

4 Beds ⋅ 3 Baths ⋅ IG26213266 MLS ⋅ Active Status

Welcome home to this stunning Whisper Ranch home! Nestled in a highly desired neighborhood, this beautifully upgraded 4 bedroom 2.5 bathroom home perfectly blends modern indoor luxury with exceptional outdoor living. From the moment you arrive you will love the pristine curb appeal, highlighted by the freshly painted exterior and the welcoming sitting front porch. Perfect for having morning coffee time! Step inside to the sprawling layout, discover the beautiful fireplaces, and explore the dream kitchen built for culinary enthusiasts. The heart of the home features high end quartz countertops and a premium, commercial grade chef’s refrigerator and freezer configuration that offers massive storage and a sleek aesthetic. The floor plan provides optimal space for everyone, anchored by a large master suite sanctuary complete with a spacious attached bathroom. Three additional well sized bedrooms offer plenty of room for family, guests, or a dedicated home office. The outdoor space is a true oasis situated on a large lot. Step into the newly landscaped pool sized back yard, where you can host gatherings effortlessly with your newly built barbecue island. The grounds also feature a dedicated dog run, and RV potential to park your toys securely. Turnkey and loaded with premium updates, this Whisper Ranch beauty won’t last long! Schedule your showing today!

13509 Margaret, 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

10961 Desert Lawn Drive Unit 365, Calimesa

$269,900

3 Beds ⋅ 2 Baths ⋅ NP26211902 MLS ⋅ Active Status

3 Bedrooms with no back neighbors!!! This home has the desired Jack & Jill plan which separates the primary bedroom from the 2 guest bedrooms. The primary bedroom is quite large, it has a king-size bed, dressers, nightstands etc. It also has a walk-in closet and attached primary bath which has a separate tub and 60” shower. The other 2 bedrooms and guest bath are separated by the living room, kitchen and family room. if you have guest and want some privacy this plan is divine. The living room is upon entry, the dining area and kitchen are just steps away. The breakfast bar is a great substitute for having a quick bite instead of using the dining set. The main kitchen appliances remain with the home as well as the washer and dryer. The step-down family room can certainly accommodate quite a bit of furniture and company if needed, think of the possibilities! Ther are grab bars for convenience if needed to the family room. The guest bedrooms are roomy and well maintained which is separated by the guest bathroom. There are French doors that lead out to the enclosed patio room which at this point is an office and exercise room combines. From there the fenced in backyard and patio area is right out the doorway. The 2 car garage has built in cabinets which a few of them do stay with the home and last but not least, this home has 15 solar panels which are included!

10961 Desert Lawn Drive Unit 365, Calimesa

$375,000

3 Beds ⋅ 2 Baths ⋅ IG26206482 MLS ⋅ Coming Soon Status

WELCOME TO 197 SUMMIT VIEW Welcome to 197 Summit View, a charming 3-bedroom, 2-bath home located in a beautiful senior community in the heart of Calimesa. Built in 1974, this two-story home offers approximately 1,239 square feet of comfortable living space with thoughtful updates throughout. Step inside to a warm and inviting interior designed for comfortable everyday living. Recent improvements include a new central HVAC system, while the all-electric setup and owned solar panels offer added efficiency and convenience. The home also features an attached garage and multiple patio areas that provide inviting spaces to relax outdoors, enjoy the pleasant views, or spend time with family and friends. The well-established community features mature landscaping and HOA amenities that include a swimming pool and clubhouse, giving residents additional spaces to relax, gather, and enjoy the neighborhood. Conveniently located near shopping, dining, services, and local amenities, 197 Summit View offers the comfort of an established Calimesa neighborhood with features that make everyday living easy and enjoyable. Come see what makes this home and community such a special place to call home.

197 Summit View, Calimesa

$539,900

3 Beds ⋅ 3 Baths ⋅ IV26209070 MLS ⋅ Active Status

This FORMER MODEL HOME has an enviable golf course location in the Aberdeen neighborhood of Chapman Heights. Feel as if you have an expanse of yard without the maintenance! Upon entering this beautiful home, you'll be struck by the views and the automatic comfort as well as the designer touches that come with a former model home like downstairs hardwood flooring. On the first level, there is a 1/2 guest bathroom and a living room which opens to the dining area which opens to the kitchen, making the home ideal for entertaining. Ample counter space and a pantry make the kitchen well designed for a host of meals and midnight snacks. The backyard is easy to maintain and opens from the dining area via sliding glass door for seamless barbecueing or coffee enjoying. Upstairs you'll find a spacious primary bedroom with en suite with separate tub and shower combination, double sinks, and a walk in closet. Paired with a balcony, the primary is situated as its own retreat within the home. The laundry room is efficiently located upstairs, as are the two remaining bedrooms, which boast an abundance of natural light and views, and the other bathroom. A whole house fan helps keep the home feeling cool and helps with the electric bills, while one of the HOAs covers front yard maintenance, leaving you with more time to enjoy nearby parks, trails, and leisurely walks around the neighborhood. Well maintained, conveniently located, and turnkey, this home just needs its new owners.. bring your golf clubs!

33333 Wallace, 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

$592,000

4 Beds ⋅ 3 Baths ⋅ IV26208659 MLS ⋅ Active Status

33825 Glenoaks Dr is a two-story Yucaipa home with a vaulted living room and a covered backyard patio overlooking an open lawn. The kitchen’s wraparound counters and breakfast bar provide preparation space and casual seating beside the dining area, with windows facing the backyard. Tall windows bring natural light into the front living room, while a separate sitting area centers on a fireplace. A downstairs bedroom and full bathroom add flexibility to the four-bedroom layout. Upstairs, the primary bedroom includes a walk-in closet and an adjoining bathroom with double sinks and a tub-shower blend. Outside, the covered patio creates a shaded setting for dining or seating, with mature trees bordering the lawn. An attached garage and broad driveway provide parking, while a separate laundry room includes overhead cabinets for storage. Included 100-Day Home Warranty with buyer activation

33825 Glenoaks, Yucaipa

$899,000

4 Beds ⋅ 3 Baths ⋅ IV26204970 MLS ⋅ Active Status

Sharon Way — Ranch Living Near Wildwood Park, Yucaipa RARE PROPERTY ALERT!! — An extraordinary ranch opportunity in Yucaipa that truly doesn’t come around often. If you’ve dreamed of planting your own orchard, cultivating a vineyard, raising horses, goats, and chickens, or even running a business, steps from your front door with coffee in hand, this property delivers the space and freedom to make it real. Set on 3.5 acres of usable land, this ranch is paired with a beautifully updated 3,000 sq ft single story home overlooking your own private canyon. The acreage is a blank canvas ready for your vision — agricultural, equestrian, recreational, or entrepreneurial. A bounty of mature fruit trees already thrives here, including Lime, Lemon (two varieties), Orange, Grapefruit, Pomegranate, Plum, Apple, Peach, Asian Pear, Fig, and Grapes. A major 2022 renovation and expansion added a stunning new primary suite, spa style bathroom, and a multipurpose room with canyon views (easily convertible to a 5th bedroom). Additional upgrades include a new roof, new HVAC, new windows, and beautifully refreshed kitchen and bathroom spaces. All bedrooms are conveniently located on one level, offering true single story ranch living. The location is exceptional — just a short walk, bike ride, or horseback ride to Wildwood Canyon State Park, and minutes from Oak Glen, Bogart Regional Park, Yucaipa Regional Park, Old Town Yucaipa, and the 10 freeway for commuters. Major employment centers in Loma Linda and Redlands are within easy reach. Wildwood Elementary School is also a quick and convenient walk from your front door. This is more than a home — it’s a lifestyle, a legacy property, and a rare chance to own acreage in one of Yucaipa’s most desirable ranch corridors. **Please note that the house has been virtually staged in the photos**

36098 Sharon, Yucaipa

$575,000

5 Beds ⋅ 3 Baths ⋅ IG26205274 MLS ⋅ Active Status

Mornings here start slow, coffee in hand while the neighborhood wakes up, and evenings belong to the backyard: a private patio, turf that never needs mowing, and a mountain view that shows up every single day. Yucaipa living, minutes from the 10, with shopping close and commutes to Redlands, San Bernardino, and anywhere else the Inland Empire needs you. This is a house that holds a full life without breaking a sweat. The island is where the good stuff accumulates, the slow breakfasts, the long dinners, the people who drop by and stay. A built-in desk quietly absorbs the paperwork of everyday life. And a bedroom with its own bath on the main floor means guests get their own corner of the house, their own rhythm, their own door to close. Upstairs feels like a retreat that doesn't try. A primary suite with a walk-in closet that ends the morning negotiation over drawer space, and a laundry room with a sink and real storage, so the machinery of family life stays tucked away where you don't have to look at it. Then there's the quiet relief of a house that's already done. Solar, owned outright. Tankless hot water. EV charging station. A yard that invites you to sit and stare at the mountains instead of mowing, and an HOA that keeps the front lawn and playground ready for the kids next door. Newer built, five bedrooms, three baths, nearly 2,500 square feet, with the upgrades that usually cost a fortune already in place, not a project waiting on you.

31960 Chagall Way, Yucaipa

$604,000

4 Beds ⋅ 3 Baths ⋅ IG26200846 MLS ⋅ Active Status

Welcome to 11992 Greenbluff Way in the desirable Chapman Heights community of Yucaipa! This spacious 4 bedroom, 3 bath home offers an open and comfortable floor plan with plenty of natural light and mountain views. The main level features a bedroom and full bath, making it perfect for guests, a home office, or anyone looking for single-level living space. The living room and family room provide plenty of room to spread out, with a cozy fireplace in the family room and easy access to the kitchen. This home also offers fresh exterior paint newly, added ceiling fans and keyless entry into the garage as well as a newer AC unit. Upstairs you'll find three additional bedrooms, including a spacious primary suite with a walk-in closet and private bathroom featuring dual sinks, a soaking tub and separate shower. The kitchen offers plenty of cabinet space, a center island and a great view toward the backyard. Outside, enjoy a private backyard with no home directly behind you and beautiful mountain views and newly poured concrete around the home. There's even a 50 amp plug in the garage to charge your EV! Located in Chapman Heights with easy access to parks, shopping, dining and local schools. This is a great home in a great Yucaipa location!

11992 Greenbluff, Yucaipa

$699,900

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.