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

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

Welcome to the picturesque region of Yucaipa, Calimesa, and Oak Glen, where the beauty of Southern California meets the charm of small-town living. Nestled against the stunning backdrop of the San Bernardino Mountains, this area is renowned for its breathtaking landscapes, lush orchards, and vibrant community spirit. With its mild climate and abundant outdoor activities, it’s no wonder that families and nature lovers alike are drawn to this enchanting locale.

Yucaipa boasts a rich history and a plethora of parks, hiking trails, and recreational facilities, making it an ideal destination for those who enjoy an active lifestyle. Calimesa, with its serene atmosphere and friendly neighborhoods, offers a perfect blend of tranquility and accessibility. Meanwhile, Oak Glen is famous for its apple orchards and scenic views, providing residents with a unique opportunity to immerse themselves in nature while enjoying the seasonal bounty.

For those seeking a home in this delightful region, you’ll find an array of stunning properties with two-level stories that cater to diverse lifestyles. These homes often feature spacious layouts, perfect for families or those who love to entertain. With ample room for growth and creativity, two-story homes provide not just space but also the opportunity to design your dream living environment. Imagine waking up to mountain views, enjoying family gatherings in expansive living areas, and retreating to your cozy bedroom sanctuary at the end of the day.

Yucaipa, Calimesa, and Oak Glen offer more than just houses; they provide a lifestyle rich in community, nature, and opportunity. Come explore the possibilities of your new home in this captivating region!

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

$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
$599,999
5 Beds ⋅ 3 Baths ⋅ PW26158085 MLS ⋅ Active Status
Welcome to this beautifully maintained 5-bedroom, 3-bathroom home offering approximately 2,854 square feet of modern living space in the desirable Summerwind Trails community of Calimesa. Built in 2020, this spacious residence features an open-concept floor plan designed for both everyday living and entertaining. The stylish kitchen flows seamlessly into the expansive family room, while a convenient downstairs bedroom and full bath provide flexibility for guests or multigenerational living. Upstairs, you'll find generously sized bedrooms and a versatile loft space. Enjoy an attached garage, central air conditioning, and a private backyard ready for relaxation or entertaining. Conveniently located near parks, schools, shopping, dining, and easy freeway access, this move-in-ready home offers the perfect blend of comfort, style, and convenience in one of Calimesa's fastest-growing neighborhoods.

1136 Poinsettia Circle, Calimesa
$849,000
5 Beds ⋅ 3 Baths ⋅ IG26158136 MLS ⋅ Active Status
Welcome to this stunning turnkey home in the highly sought-after Chapman Heights community! Beautifully maintained and move-in ready, this exceptional property offers the perfect blend of comfort, style, and energy efficiency with paid-off solar and a sparkling saltwater pool and spa, making it ideal for year-round enjoyment. The thoughtfully designed floor plan provides spacious living areas filled with natural light, creating a warm and inviting atmosphere for both everyday living and entertaining. Step outside to your private backyard oasis, where the saltwater pool offers the perfect place to relax, cool off, or host family and friends. Conveniently located just moments from Chapman Heights Elementary School and the Yucaipa Valley Golf Club clubhouse, you'll enjoy easy access to parks, walking trails, golf, shopping, dining, and all the amenities this desirable community has to offer. This beautiful home truly checks all the boxes. Don't miss your opportunity to own a turnkey home with paid solar, a resort-style backyard, and an unbeatable Chapman Heights location!

33665 Wild Horse, Yucaipa
$1,299,000
4 Beds ⋅ 3 Baths ⋅ 219150501DA MLS ⋅ Active Status
Incredible opportunity to own this sprawling estate, recently acquired through foreclosure proceedings. A nearly 4,000 sq. ft. two story country residence with brick facade and grand entry hall. Home has been updated with beautiful custom cabinetry, updated baths, granite countertops and many other upgrades. 4.74 acre property is breathtaking and perched on a promontory with sweeping 360 degree views of city lights, San Gorgonio, San Jacinto, and most every mountain range in the Southern California vicinity. Past the remote controlled entry gates of the exclusive Oak Hills Estates, you enter your compound via a long sweeping private driveway. 3 car attached garage, large pool and spa, extensive solar array, private orchards and vineyards, and two ponds and a steam highlight the extensive grounds and improvements.

37245 Valgio Drive, Calimesa
$579,000
4 Beds ⋅ 3 Baths ⋅ IG26156751 MLS ⋅ Active Under Contract Status
Welcome to this beautifully maintained 4-bedroom, 3-bathroom home that checks every box on your wish list! Featuring a highly desirable floor plan with one bedroom and a full bathroom conveniently located downstairs, this home offers flexibility for guests or a home office. The bright, clean kitchen is equipped with sleek stainless steel countertops and opens to the main living areas, creating an inviting space for everyday living and entertaining. The large living room showcases beautiful wood flooring and Tiled fireplace adding warmth and elegance to the home's inviting atmosphere. The spacious primary suite serves as a private retreat, featuring a generously sized bedroom and an oversized walk-in closet. The additional guest bedrooms are all generously sized with ample closet space. Step outside to a large backyard with RV parking, offering plenty of room for entertaining, storing recreational vehicles, or creating your dream outdoor oasis. Located in a welcoming, family-friendly neighborhood with NO HOA, this home combines comfort, functionality, and exceptional value. With its versatile layout, spacious living areas, large backyard, and desirable features, this home truly checks every box on your checklist. Don't miss the opportunity to make this move-in-ready home yours!

12897 Brigid Court, Yucaipa
$8,995,000
CV26156701 MLS ⋅ Active Status
**Call or Email for Offering Memorandum** Pleased to present for sale 12446 18th Street, Yucaipa, California, a 19-unit vacant multifamily community consisting of all two-bedroom, two and a half-bathroom townhome-style apartment units. Constructed in 2026, this offering represents a rare opportunity to acquire a newly constructed asset in one of the Inland Empire’s most active, developing submarkets. The Yucaipa Townhomes are all-electric and built to the same standard, offering a cohesive, institutional-quality product that commands premium rents while minimizing near-term capital expenditure risk. The two-story layout features an open main level with kitchen, dining, living area, powder room, and direct two-car garage access, complemented by two private en-suite bedrooms upstairs, one bedroom with a walk-in closet. The units are individually metered for electricity and have individual hot water heaters. The result is a highly livable, two-bedroom, two-and a half-bathroom ?oor plans (1,090 S.F. each) that appeals to a broad renter demographic, from working couples and young families to dual-income households seeking the feel of a single-family home at a multifamily price point. Each unit also features a large private backyard with a patio cover that is a rare offering among comparable Yucaipa multifamily products. Unit ?nishes are thoughtfully appointed throughout: quartz countertops, white oak-style plank ?ooring, shaker cabinets, recessed lighting, and cathedral ceilings. Each kitchen includes a dishwasher, refrigerator, and electric stove/oven, and each unit has its own individual hot water heater located in the garage. Every unit includes a direct two-car attached garage with an electric garage door opener and a 220V dryer outlet, a 200-amp electrical panel, central air conditioning and heat, and in-unit washer/dryer hookups. The community is secured with a code-access entry gate at the front entrance and a side exit gate, and features centralized mailboxes, low-maintenance landscaping, and an outdoor picnic area with arti?cial turf.

12446 18th, 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.