Yucaipa/Calimesa/Oak Glen (269) Homes for Sale

Yucaipa/Calimesa/Oak Glen (269) Homes for Sale

Welcome to the enchanting region of Yucaipa, Calimesa, and Oak Glen, California—an idyllic destination that beautifully blends natural beauty with suburban charm. Nestled against the stunning backdrop of the San Bernardino Mountains, this area is renowned for its picturesque landscapes, vibrant community, and a plethora of outdoor activities.

Yucaipa offers a delightful small-town atmosphere, where you can enjoy a leisurely stroll through its charming downtown filled with boutique shops, local eateries, and seasonal farmers' markets. The city is also home to several parks and hiking trails, making it a haven for nature enthusiasts and families alike. Just a stone's throw away, Calimesa presents a tranquil lifestyle with its friendly neighborhoods and a strong sense of community.

Oak Glen, famed for its apple orchards and seasonal festivals, adds a touch of rustic charm to the area. It’s the perfect spot for apple picking in the fall, and its scenic beauty attracts visitors year-round.

For those looking to call this beautiful region home, there are a variety of homes for sale that cater to diverse tastes and budgets. From cozy single-family homes to spacious estates with breathtaking views, the real estate options are as varied as the landscapes themselves. Whether you're seeking a peaceful retreat or a vibrant community, Yucaipa, Calimesa, and Oak Glen have something to offer everyone.

Explore the homes for sale in this captivating region and discover the perfect place to create lasting memories in the heart of Southern California!

Newest Yucaipa/Calimesa/Oak Glen (269) Homes for Sale

$529,100
3 Beds ⋅ 2 Baths ⋅ FR26198326 MLS ⋅ Active Status
This home is absolutely gorgeous, charming and inviting! She has had many upgrades through the years, to name a few. Top of the line double pane windows, laminate flooring, redesigned kitchen within the last 10 years with new cabinets and granite countertops. New 40 gallon water heater in, "2025". upgraded electrical. There is also a whole house fan. She has just been freshly painted inside and out. New vanities with quartz countertops in both bathrooms also fixtures, toilets, and hardware. New ceiling fans and light fixtures throughout. New stainless steel appliances, (Range with glass cooktop, dishwasher, microwave, and even a new garbage disposal! ) The yard just had a makeover and is equipped with automatic sprinklers. The majestic corner lot is lined with mature trees and lovely walkways with custom brickwork. She has been professionally cleaned inside and out and ready for you to move right in! The washer, dryer and refrigerator are include! Hurry to tour won't last priced to sell: 529,100.00

35465 Date Avenue, Yucaipa
$599,000
4 Beds ⋅ 3 Baths ⋅ IG26197289 MLS ⋅ Active Status
Beautifully appointed 4-bedroom, 3-bathroom home with a highly desirable first-floor bedroom and full bath. The welcoming entry opens to formal living and dining, while the spacious kitchen features white cabinetry, gray quartz countertops, and a breakfast nook that flows into the family room with a cozy fireplace. Upstairs offers three additional bedrooms, including a spacious primary suite with walk-in shower, soaking tub, and large walk-in closet. A striking skylight above the staircase fills the home with natural light. Enjoy the backyard's new patio and pergola, plus a side yard perfect for gardening. Ideally located next to Yucaipa Regional Park and Lake, minutes from downtown Yucaipa, dining, entertainment, and freeway access, with easy access to Redlands and Highland. This is the perfect blend of style, comfort, and location.

34982 Summerwood, Yucaipa
$385,000
2 Beds ⋅ 2 Baths ⋅ IG26192889 MLS ⋅ Active Status
**Welcome to Sun Park 11!** This beautifully updated, move-in-ready 2-bedroom, 2-bath home is one you won’t want to miss! Located in a desirable senior community, this charming property offers comfortable living with thoughtful updates throughout and pride of ownership evident from the moment you arrive. Step inside to discover a fresh, inviting interior featuring fresh paint throughout, an updated kitchen, and beautifully refreshed bathrooms. The spacious layout provides plenty of room to relax and entertain, while the separate laundry room and enclosed sunroom add valuable versatility and functionality. Enjoy the outdoors in your private backyard, complete with established citrus trees—perfect for relaxing, gardening, or enjoying your morning coffee. The home also offers a garage for convenient parking and storage. Residents of Sun Park 11 enjoy a wonderful community setting with a greenbelt and community pool just a short walk away. Conveniently located near shopping, dining, Yucaipa’s Uptown district, and the beautiful Oak Glen area, this home offers both comfort and convenience in a peaceful community setting. Move-in ready, beautifully updated, and ideally located—come see why this home is the one you've been waiting for!

11944 4th Street, Yucaipa
$290,000
2 Beds ⋅ 2 Baths ⋅ IG26196756 MLS ⋅ Active Status
This home has alot to offer it has a great location in a 55+ community in Calimesa. The Mountain views from every part of the yard and the storage you will have plenty of it to make your move easy. This home is close by the club house where the community loves to hold all kinds of event for the people that live in the sharondale community. Come take a tour of this great home in a great location.

9401 Sharondale, Calimesa
$574,900
3 Beds ⋅ 2 Baths ⋅ IG26196171 MLS ⋅ Coming Soon Status
Back on the market with New Pergo Flooring and Paint!!! A rare opportunity in Upper Yucaipa—two homes on one lot with a versatile layout and thoughtful updates throughout! 35263 Beech Avenue offers a charming 2-bedroom, 1-bath front home plus a separate studio, creating wonderful possibilities for multi-generational living, guests, a home office, or investment use. Step inside the front home and immediately notice the gorgeous new Pergo flooring, adding a fresh, updated look throughout the living spaces. The light and bright family room features newer windows, recessed lighting, and a ceiling fan, then flows into a charming dining area complete with built-in cabinetry and custom ceiling details. The updated kitchen is full of character, featuring butcher block countertops, a farmhouse sink, matte black fixtures, and newer appliances. Refrigerators in both units are included. Outside, enjoy a welcoming front patio perfect for morning coffee, along with a private backyard offering plenty of space for BBQs, entertaining, gardening, or outdoor play. Tucked behind the main home is the separate studio, thoughtfully designed with an open living/sleeping area, galley-style kitchen with room for a breakfast table, and an updated full bathroom. Both units have access to a separate laundry room, providing added convenience while maintaining separation between the living spaces. The fully gated property also includes a large storage shed with possibilities for a workshop, hobby room, playhouse, or additional storage. Alley access provides convenient access to the rear of the property and additional flexibility for RV or trailer parking. Mature Landscaping and Fruit Trees, ( Avocado, Orange and Lemon) With two distinct living spaces, updated interiors, new flooring, outdoor areas, and a highly functional front-home/back-home configuration, this Upper Yucaipa property offers flexibility that is hard to find. Move-in ready and ready for its next chapter!

35263 Beech, Yucaipa
$1,050,000
4 Beds ⋅ 4 Baths ⋅ IG26195990 MLS ⋅ Active Under Contract Status
Nestled in the highly desirable Hidden Meadows neighborhood of Yucaipa, this stunning custom single-story residence offers space, quality, and thoughtful design throughout. Situated on over half an acre, the property features 4 bedrooms, 2 full bathrooms and 2 half bathrooms (One half bath located in the garage), and approximately 2,819 square feet of living space. The spacious floor plan includes a formal living room, formal dining room, and an expansive family room ideal for both everyday living and entertaining. The large kitchen is appointed with a center island, stainless steel appliances, custom white cabinetry, recessed lighting, and a picture window looking out to the backyard. The primary suite offers a private retreat complete with a fireplace and seating area. The upgraded primary bathroom features dual vanities, a soaking tub, and a large walk-in shower with windows providing natural light and backyard views. Interior finishes include custom tile work, laminate wood flooring, large baseboards, and window shutters. Outdoor amenities include a full-length covered patio across the rear of the home, a detached patio area with fireplace, an additional detached gazebo, mature landscaping, block walls, and wrought-iron fencing. Car enthusiasts and hobbyists will appreciate the oversized garage offering approximately 1,440 square feet of space, providing exceptional parking, workshop potential, and storage capacity. Plus the RV parking behind the wrought iron gate! A rare opportunity to own a spacious custom home on a large lot in one of Yucaipa’s most sought-after communities. Don't wait, this one isn't expected to last long!

37420 Wildwood View, Yucaipa
$809,000
3 Beds ⋅ 3 Baths ⋅ IG26195435 MLS ⋅ Active Status
Welcome home to this beautiful single-story property located in a desirable Yucaipa neighborhood! Featuring 3 bedrooms, 2.5 bathrooms, plus a dedicated office, this home offers a comfortable and inviting layout perfect for everyday living and entertaining. Step outside to your own backyard retreat featuring a sparkling pool and relaxing hot tub, surrounded by beautiful views and breathtaking sunsets. Additional highlights include a 3-car garage, central vacuum system, and leased solar. Whether you’re relaxing poolside, entertaining family and friends, or ending the day with a beautiful sunset, this is a home you’ll want to experience in person. Come see the lifestyle this home has to offer—schedule your private showing today and picture yourself calling it home!

13690 Chaparral trail, Yucaipa
$649,900
3 Beds ⋅ 2 Baths ⋅ IV26191108 MLS ⋅ Active Status
Welcome to 32377 Avenue D in Yucaipa an exceptional opportunity offering space, versatility, and exciting future potential! This single-story home features 3 bedrooms, 2 bathrooms, approximately 1,752 square feet of living space, plus a basement that provides valuable additional storage and flexible-use possibilities. Situated on a sprawling 37,800 sqft. lot, the property also includes city-approved plans for two additional dwelling units, creating an outstanding opportunity for multigenerational living, potential rental income, or future expansion. The existing home offers a functional floor plan, comfortable living areas, and abundant outdoor space for entertaining, gardening, recreational use, or additional parking. Conveniently located near shopping, dining, schools, parks, and major commuter routes. Whether you are a homeowner, investor, or developer, this unique property offers tremendous possibilities. Don’t miss the opportunity to own a substantial piece of Yucaipa with approved plans already in place. Buyer to independently verify the basement’s permitted status and square footage, as well as all permits, ADU approvals, zoning, utilities, development requirements, and intended uses with the City of Yucaipa and the appropriate agencies.

32377 Avenue D, Yucaipa
$549,900
2 Beds ⋅ 1 Baths ⋅ IG26194714 MLS ⋅ Coming Soon Status
A large, versatile bonus room with a built-in fireplace steals the spotlight in this darling ranch-style home. With 2 bedrooms, 1 bathroom, generously sized rooms throughout, and a spacious kitchen, this home offers plenty of room to live, work, and grow. Beautiful landscaping and a gated yard provide privacy and curb appeal, while the backyard offers low-maintenance turf, a shed, and plenty of room to make it your own. The 2-car garage offers plenty of cabinetry, a workshop bench, and overhead storage. A large, fenced RV parking adds even more versatility. Ideally located near Uptown Yucaipa—close to everything, yet tucked away from the hustle and parking challenges. A wonderful home for any season of life! Additional photos to come.

12001 2nd Street, Yucaipa
$599,900
2 Beds ⋅ 2 Baths ⋅ IG26194625 MLS ⋅ Active Status
A Rare Opportunity in the Heart of Majestic Oak Glen. Some properties simply give you a place to live. Others give you a story, a setting and possibilities that are difficult to recreate. Tucked away among the towering trees and natural beauty of Oak Glen, this extraordinary property offers approximately 2.6 acres and two uniquely charming units, creating an opportunity unlike almost anything else you will find in this treasured mountain community. From the moment you enter, there is a feeling that this property is special. Mature oak trees create a breathtaking canopy, the peaceful setting feels worlds away from the city below, and the two distinctive units blend naturally into their surroundings. Whether envisioned as a private family compound, multigenerational retreat, guest accommodations, artist's getaway, investment opportunity or something entirely different, the possibilities here are remarkable. And then there is the history. Oak Glen has been a special part of Southern California since the 1800s, known for its orchards, ranches, mountain landscape and generations of families who have worked to preserve its rural character. This property seems to capture that same spirit one-of-a-kind, rooted in the land and impossible to duplicate. Among its most fascinating features is an enormous heritage oak tree that the seller states has been identified as the largest oak tree in San Bernardino County, creating a natural centerpiece that must truly be experienced in person. Water is another extraordinary feature. The seller reports the private well is considered one of the strongest-producing wells in Oak Glen, an impressive feature for a mountain property and one buyers will certainly want to explore further. The property also offers a shared septic system, propane, additional storage and areas of usable land that invite you to imagine what could come next. There appears to be additional space toward the upper portion of the property that may offer future possibilities, subject of course to county requirements and buyer investigation. This isn't a property that can be fully appreciated by reading about it, you need to walk the land, hear the quiet, stand beneath the magnificent oak and experience Oak Glen for yourself. For the buyer looking for something truly different, this may be one of those rare properties that only comes along once.

39922 Pine Bench Road, Oak Glen
$499,900
3 Beds ⋅ 2 Baths ⋅ SW26194603 MLS ⋅ Active Status
Single story home in the established central yet quiet section of town. Located on a large lot with neighbors on one side, located deep off the street with a long driveway. An open and spacious floorplan with a side patio, entertainers living room and 3 bedrooms plus on office space, many with views of open space and hills. Located. Sit out the back and enjoy the sunset and wildlife, don't miss out on this amazing opportunity!

12431 8th, Yucaipa
$639,900
4 Beds ⋅ 2 Baths ⋅ IG26193441 MLS ⋅ Active Status
You will not want to pass by this original owner, 4 bedroom, 2 bath home, located on one of the most desired strreets in Chapman Heights. It will be difficult to want to leave for work in the morning after enjoying your coffee in your private, beautifully landscaped back yard. All four bedrooms, including the primary suite, are downstairs. Kitchen opens up to the family room. The upstairs loft is a perfect way to keep the kids entertained close by. This is the ideal home for any size family. The private location offers the peace and tranquility you need, or the space and the neighborhood to entertain as many guests as you can fit. This is a memory making home, for sure. See you soon!

33516 Lansford Street, 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.