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

Welcome to the enchanting region of Yucaipa, Calimesa, and Oak Glen, a hidden gem nestled in the heart of Southern California. This picturesque area is renowned for its stunning natural beauty and a vibrant community spirit. Surrounded by the majestic San Bernardino Mountains, residents enjoy breathtaking views, outdoor adventures, and a mild climate that makes every day feel like a vacation.

Yucaipa is celebrated for its charming downtown, filled with boutique shops, delightful eateries, and a warm sense of community. Calimesa, with its serene atmosphere, offers a peaceful retreat while still being conveniently close to urban amenities. Just a short drive away, Oak Glen invites you to explore its apple orchards, hiking trails, and seasonal festivals that celebrate the beauty of nature.

For those seeking spacious living, homes with two levels in this region provide the perfect blend of comfort and style. These multi-story residences often boast open floor plans, allowing for seamless transitions between living spaces. Imagine entertaining friends in your expansive living room or enjoying family gatherings in a beautifully designed kitchen that flows effortlessly into a dining area. With ample bedrooms and versatile spaces, two-story homes cater to various lifestyles, whether you’re a growing family or seeking a home office retreat.

Living in Yucaipa, Calimesa, or Oak Glen means embracing a lifestyle filled with outdoor activities, community events, and a strong sense of belonging. Discover the perfect two-level home in this enchanting region, where every day offers new adventures and cherished memories. Come experience the charm and warmth of this delightful corner of California!

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

$69,000

2 Beds ⋅ 1 Baths ⋅ IG26168861 MLS ⋅ Active Status

Welcome to 13063 5th St., Space 5 in Yucaipa—a beautifully fully renovated home located in a peaceful 55+ community, offering comfort, convenience, and low-maintenance living. This move-in-ready home features a new electrical panel, new flooring, fresh interior paint, new windows, new sliding glass door, a completely remodeled bathroom, new light fixtures, updated hardware, new outlets, timer switches, and two energy-efficient mini-split systems for year-round comfort. The washer and dryer (approximately 3 years old) and most furniture are included, making this a truly turnkey opportunity. Enjoy the welcoming community amenities, including a clubhouse, sparkling pool, recreation area, and beautifully maintained grounds—all just minutes from Interstate 10, shopping, dining, and the Yucaipa Valley Golf Club. Whether you're looking to downsize or enjoy a relaxing retirement, this charming home is ready to welcome you.

13063 5th St #5, Yucaipa

$615,000

4 Beds ⋅ 3 Baths ⋅ IV26169582 MLS ⋅ Active Status

Newer house in a highly sought-after neighborhood in Calimesa. With all the amenities of a newly constructed modern home, this property boasts a lot of upgrades inside and out. Just recently added a 16' x 24' Aluminum base patio and retaining walls in the backyard. The Master bedroom, with a Full bathroom is located on the main floor while a half bath was also located on the main floor. The three other bedrooms and a Full bathroom can be seen on the second floor. And FYI, a new Stater Brother just started serving customer in the Cherry Valley area. A Must see!

1271 Pinehurst, Calimesa

$949,000

4 Beds ⋅ 4 Baths ⋅ IG26167242 MLS ⋅ Active Status

Welcome to this exceptional 3,850-square-foot Chapman Heights residence, perfectly situated on an expansive 14,824-square-foot lot. Offering 4 spacious bedrooms, 3½ bathrooms, and an impressive blend of luxury, comfort, and energy efficiency, this home is designed for both everyday living and unforgettable entertaining. The thoughtfully designed floor plan features a MAIN-LEVEL PRIMARY SUITE, providing privacy and convenience. This luxurious retreat includes a comfortable sitting area, a spa-inspired ensuite bathroom with a jetted soaking tub, separate walk-in shower, dual vanities, and an oversized walk-in closet. At the heart of the home is the beautifully updated kitchen, complete with elegant quartz countertops, a five-burner cooktop, built-in oven and microwave combination, stainless steel farmhouse sink, walk-in pantry, and abundant cabinetry. The kitchen flows seamlessly into the inviting family room, where a cozy fireplace and expansive sliding glass door create the perfect connection between indoor and outdoor living. Upstairs, you'll find three generously sized bedrooms, two full bathrooms featuring dual vanities, and a versatile loft that can easily serve as a media room, game room, home office, or additional living space and an abundance of cabinet space. Additional interior features include plantation shutters throughout, a whole-house fan, a dedicated laundry room with utility sink, a convenient downstairs powder room, and a highly efficient climate control system with a dedicated HVAC unit for the primary suite plus separate dual-zone controls for the upstairs and downstairs living areas. Step outside to your own private backyard paradise. Designed for year-round enjoyment, the resort-style yard showcases a heated saltwater pool with an exciting water slide, built-in spa, fully equipped outdoor kitchen, putting green, dedicated garden area, and plenty of space to relax or entertain family and friends. Additional highlights include approximately 28 SOLAR PANELS (Lease), a three-car garage equipped with an electric vehicle charger, and outstanding curb appeal. Located in the highly desirable Chapman Heights community, this exceptional home is just minutes from Yucaipa High School, Crafton Hills College, shopping, parks, golf, and convenient freeway access. This is a rare opportunity to own a home that perfectly balances elegance, efficiency, and resort-style living in one of Yucaipa's most sought-after neighborhoods.

33264 Gold Mountain Road, Yucaipa

$799,000

4 Beds ⋅ 3 Baths ⋅ MB26167139 MLS ⋅ Active Status

Welcome to 11432 Piñon Trail in Yucaipa—a move-in-ready, 4-bedroom, 3-bathroom home featuring modern upgrades, spacious living areas, and an excellent location across from Yucaipa Regional Park. Ideal for first-time home buyers or anyone seeking additional space, this beautifully maintained Yucaipa home offers a bright, open floor plan with soaring cathedral ceilings and high windows that fill the interior with natural light. The spacious kitchen is perfect for everyday meals and entertaining, featuring a farmhouse sink, gorgeous countertops, a large center island, ample cabinetry, and generous workspace. The large lot provides plenty of outdoor space for summer barbecues, entertaining guests, relaxing, and creating your own backyard retreat. Every detail has been thoughtfully maintained and upgraded with care, creating a comfortable home ready for its next owner. With four bedrooms, three bathrooms, flexible living areas, and modern conveniences, there is room to grow, work from home, entertain, and create lasting memories. Enjoy convenient access to outdoor recreation, shopping, dining, schools, and local amenities. If you are searching for a first-time buyer home in Yucaipa, a move-in-ready 4-bedroom house, an upgraded kitchen, an open floor plan, a large lot, or a home near Yucaipa Regional Park, this property stands out. Discover the space, comfort, and location you have been waiting for—schedule your private showing today!

11432 Pinon, Yucaipa

$995,000

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

$958,000

5 Beds ⋅ 5 Baths ⋅ CV26164138 MLS ⋅ Active Status

Perched atop one of the most desirable view lots in the exclusive gated community of Oak Hills, this extraordinary custom-built estate delivers an unparalleled combination of luxury, privacy, and breathtaking panoramic views stretching across the valley, city lights, and surrounding mountains. Set on approximately 4.56 acres, this impressive residence offers over 4,100 square feet of thoughtfully designed living space with 5 bedrooms and 5 bathrooms, including a private guest suite with its own entrance—ideal for multi-generational living, extended family, or long-term guests. From the moment you step through the grand double-door entry, soaring ceilings, abundant natural light, and expansive picture windows showcase the home's spectacular setting. The open-concept layout is designed for effortless entertaining, while the gourmet kitchen features granite countertops, generous workspace, and seamless flow into the main living and dining areas. The luxurious primary suite is a private retreat complete with a spa-inspired bathroom and stunning views, while an additional upstairs primary suite provides exceptional flexibility. Several bedrooms offer walk-in closets and private balconies where you can enjoy unforgettable sunrises, sunsets, and sparkling evening city lights. Step outside and experience true Southern California resort-style living. With acres of usable land, the possibilities are endless—create your dream pool, build an ADU, add a workshop, design an equestrian retreat, vineyard, or simply enjoy the unmatched peace and privacy that only a property of this caliber can provide. Additional highlights include a 4-car attached garage, gated driveway, mature landscaping, and ample parking for guests, and recreational vehicles. Rarely does a property combine luxury, acreage, breathtaking views, and endless potential in one exceptional offering. Conveniently located just minutes from I-10, shopping, dining, golf courses, and Yucaipa Regional Park, this is more than a home—it's a lifestyle destination

37550 Marondi, Calimesa

$1,100,000

4 Beds ⋅ 4 Baths ⋅ IG26162038 MLS ⋅ Active Status

Make this home your Castle! This is a well cared for 4 bedroom home with a pool and spa on a nearly 1 acre lot! Living here will make you feel like royalty! The curb appeal is majestic with the stone veneer and round two story entry. As you enter the home through the extra large wooden door and step into the the large entry you will be impressed by the large space, high cathedral ceiling, chandelier and the light that enters through the octagon windows from above. The formal living room is a few steps down to the left with a vaulted ceiling and double French doors to the backyard. The formal dinning room has a Tray Ceiling with accent lighting and double French Doors to the backyard as well. The kitchen and casual dining area includes a wonderful dark green granite countertop in a gourmet kitchen. Lots of cabinets with plenty of storage Including pull out shelving. The east end of the downstairs area has the laundry room and a cozy family room with a fireplace and sliders out to the back yard. The home has all 4 bedrooms upstairs. The primary bedroom has vaulted ceilings and great views of the mountains, fireplace, LOTS of closet space including a separate closet with racks for shoes. The en-suite bath has double sinks, a separate shower and a jetted tub where you can enjoy the view and the fireplace. Another bedroom is quite oversized while the remaining two are spacious yet traditional sized bedrooms. The upstairs hall bath includes a laundry chute down to the laundry room below! The backyard is designed for good times! There is a covered and fenced extra large patio area on the north side of the home with a protected BBQ area near the kitchen. The pool and spa include some fun features like colorful ceramic sea life elements and a Volcano Water effect that impresses the kids! Many of the walkways have been stained and some include non-slip materials for safety. The garage entries are all in the backyard behind a remote controlled gate. So, there is plenty of concrete area for many types of games, There is a three car attached garage. The single detached garage at the back of the property has held a boat and a class c RV. This garage also has a half bath and an RV cleanout. The current owner has had a love for birds and has an aviary between the carport and extra garage. The birds will be removed. You can choose to enjoy raising birds or not. If you are looking for a home with something EXTRA then you need to see this home!

10389 Walnut Grove Court, Yucaipa

$1,195,000

4 Beds ⋅ 4 Baths ⋅ CV26161821 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

$775,000

4 Beds ⋅ 4 Baths ⋅ IG26158229 MLS ⋅ Active Status

If you've been dreaming of luxury living in a resort-style community—without the luxury price tag—this is the one you've been waiting for. Welcome to The Reserve, one of Yucaipa's most sought-after communities, where every day feels like a vacation. Imagine starting your mornings with a friendly game of pickleball, spending warm afternoons relaxing by the sparkling community pool, and ending the day with neighbors and friends at the clubhouse. Step inside to discover an expansive and thoughtfully designed floor plan perfect for modern living. Just off the entry, you'll find a conveniently located downstairs bedroom and full bathroom, ideal for multigenerational living, overnight guests, or a private home office. Multiple living spaces, a formal dining room, and a spacious kitchen create the perfect setting for entertaining, while an additional downstairs powder room adds everyday convenience. Upstairs, an oversized loft offers endless possibilities. Whether you envision a media room, game room, children's play area, home gym, or an additional family room, this versatile space is ready to fit your lifestyle. Retreat to the luxurious primary suite, where breathtaking views of Yucaipa's rolling hills and mountain landscape provide a peaceful backdrop. The spa-inspired ensuite bathroom is designed for relaxation, featuring ample space to unwind after a long day. Completing the suite is an enormous walk-in closet with room for an extensive wardrobe, shoes, luggage, and more. Two additional upstairs bedrooms and another full bathroom provide plenty of room for family and guests. The immaculate two-car garage is every organizer's dream, complete with durable epoxy flooring and abundant built-in cabinetry for exceptional storage. Step outside to your private backyard oasis featuring a covered patio, perfect for alfresco dining, weekend barbecues, or simply relaxing in the shade while enjoying Southern California's beautiful weather. And when you're ready for even more fun, the incredible community amenities are just moments away. Cool off in the resort-style pool, challenge friends to a match on the tennis or pickleball courts, or gather at the clubhouse for community events and unforgettable evenings. If you've been searching for the perfect blend of luxury, comfort, and an active resort-style lifestyle, this exceptional home deserves a place at the top of your list!

31801 Oak Wood Circle, Yucaipa

$588,990

4 Beds ⋅ 3 Baths ⋅ SW26160402 MLS ⋅ Active Status

Welcome home to Siena by CrestWood Communities—an exceptional new construction home in Yucaipa where contemporary design, energy-efficient living, and everyday comfort come together. Visit the Siena Sales Center at 12708 5th Street, Yucaipa, open Saturday through Wednesday from 10:00 AM to 6:00 PM, and experience The Blake for yourself. Offering approximately 2,068 square feet, The Blake features 4 bedrooms, 3 bathrooms, a desirable downstairs bedroom, an upstairs loft, and a 2-car garage. The open-concept layout seamlessly connects the kitchen, dining, and great room, creating an inviting space for everyday living, entertaining, and making lasting memories. At the heart of the home, the beautifully appointed kitchen showcases white Shaker cabinetry, quartz countertops, and a premium Bosch appliance package, blending timeless style with modern functionality. Expansive living spaces filled with natural light create a warm, welcoming atmosphere that feels both open and connected. This energy-efficient home includes 9-foot ceilings; luxury vinyl plank flooring throughout the first-floor living areas, bathrooms, and laundry room; plush carpeting in the bedrooms, stairs, and loft; dual-pane Low-E windows; integrated solar (lease or purchase); and EV-ready prewiring for an electric vehicle charging outlet. The convenient downstairs bedroom and full bathroom offer exceptional flexibility for overnight guests, multigenerational living, or a private home office. Upstairs, the versatile loft creates additional space for a media room, playroom, study, or second living area, while the remaining bedrooms provide privacy and comfort for family and guests. The community tot lot and picnic area are perfect for gathering with family, friends, and neighbors. Ideally located near parks, shopping, dining, schools, outdoor recreation, and major commuter routes, Siena offers the perfect balance of small-community charm and everyday convenience. With a limited number of homesites available and introductory pricing currently offered, now is an exceptional time to own a new home at Siena. Qualified buyers may receive closing cost assistance or incentives toward builder upgrades, providing added value and the opportunity to personalize their new home. Schedule your private tour today and discover why Siena by CrestWood Communities is one of Yucaipa's most exciting new home communities.

34307 Chelsie Ln, Yucaipa

$570,990

3 Beds ⋅ 3 Baths ⋅ SW26157121 MLS ⋅ Active Status

Welcome home to The Cathy at Siena by CrestWood Communities—an exceptional new construction home in Yucaipa where contemporary design, energy-efficient living, and everyday comfort come together. Visit the Siena Sales Center at 12708 5th Street, Yucaipa, open Saturday through Wednesday from 10:00 AM to 6:00 PM, and experience The Cathy for yourself. Offering approximately 1,902 square feet, this thoughtfully crafted home features 3 bedrooms, 2.5 bathrooms, a versatile upstairs loft, and a 2-car garage. The open-concept layout seamlessly connects the kitchen, dining, and great room, creating an inviting space for everyday living, entertaining, and making lasting memories. At the heart of the home, the beautifully appointed kitchen showcases white Shaker cabinetry, quartz countertops, and a premium Bosch appliance package, blending timeless style with modern functionality. Expansive living spaces filled with natural light create a warm and welcoming atmosphere that feels both spacious and connected. This energy-efficient home includes 9-foot ceilings, luxury vinyl plank flooring throughout the first-floor living areas, bathrooms, and laundry room, plush carpeting in the bedrooms, stairs and loft, dual-pane Low-E windows, integrated solar (lease or purchase), and EV-ready prewiring for an electric vehicle charging outlet. Upstairs, the flexible loft offers endless possibilities as a home office, media room, playroom, or additional gathering space, while the private bedroom layout provides comfort and functionality. The community tot lot and picnic area are perfect for gathering with family, friends, and neighbors. Ideally located near parks, shopping, dining, schools, outdoor recreation, and major commuter routes, Siena offers the perfect balance of small-community charm and everyday convenience. With a limited number of homesites available and introductory pricing currently offered, now is an exceptional time to own a new home at Siena. Qualified buyers may receive closing cost assistance or incentives toward builder upgrades, providing added value and the opportunity to personalize their new home. Schedule your private tour today and discover why Siena by CrestWood Communities is one of Yucaipa's most exciting new home communities.

34311 Chelsie Ln, Yucaipa

$660,000

4 Beds ⋅ 4 Baths ⋅ IG26160230 MLS ⋅ Active Under Contract Status

HOLY MOLY...somebody call HGTV because this one is SHOWSTOPPING! Welcome to one of Yucaipa's most stunning homes located in a highly desirable gated community! Offering nearly 2,900 sq. ft. of beautifully upgraded living space with 4 bedrooms and 3.5 bathrooms, this home delivers luxury, designer finishes, and resort-style living at every turn. The formal living and dining rooms seamlessly flow into the oversized family room featuring a custom built-in entertainment center, fireplace, and open-concept design perfect for entertaining. And now for the star of the show...THE KITCHEN! This HGTV-worthy custom kitchen is guaranteed to steal the spotlight! Featuring gorgeous white shaker cabinetry, quartz countertops, a massive center island with butcher block top, custom cabinet organizers, pull-out drawers, spice racks, designer range hood, stainless steel appliances, recessed lighting, designer tile backsplash, oversized sink, wood-look tile flooring, plantation shutters, a built-in desk nook, and hanging pot rack, this is the kitchen buyers dream about. Fair warning—your guests may never want to leave! Step outside to your tropical-inspired backyard retreat complete with artificial turf, concrete hardscape, fire pit area, custom planters, and lush vines climbing the block walls, creating the perfect space to relax or entertain year-round. Upstairs you'll find three spacious guest bedrooms, two guest bathrooms, and an expansive primary suite. The luxurious primary bathroom features dual sinks, a soaking tub, walk-in shower, and an oversized walk-in closet. Additional features include a finished two-car garage with overhead storage racks for added convenience. And let's talk about SAVINGS! The home is equipped with solar at just $141 per month. The sellers have shared that it has covered 100% of their electricity usage—and they certainly don't conserve when it comes to enjoying their home! Keep the A/C running, host the holidays, and enjoy the lifestyle without worrying about sky-high electric bills. The amenities don't stop there! Enjoy resort-style living with gated entrances, a sparkling pool and spa, playground, clubhouse, and beautifully maintained grounds...even better, the HOA maintains and waters your front yard landscaping—all for just $220 per month! Luxury finishes. Tropical vibes. Resort-style amenities. An unforgettable kitchen. Low-cost solar. This isn't just a home—it's a lifestyle. The only thing missing is YOU!

33992 Lily, 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.