Yucaipa/Calimesa/Oak Glen (269) Homes with Three Or More Levels Stories

Welcome to the enchanting region of Yucaipa, Calimesa, and Oak Glen, nestled in the heart of San Bernardino County, California. This picturesque area is renowned for its stunning mountain views, lush landscapes, and a warm community spirit that invites you to call it home.

Yucaipa offers a charming blend of suburban comfort and natural beauty, making it an ideal place for families, retirees, and everyone in between. With its close proximity to the San Bernardino National Forest, outdoor enthusiasts can enjoy hiking, biking, and exploring the great outdoors right at their doorstep. Calimesa, with its friendly neighborhoods and small-town vibe, provides a sense of tranquility while still being conveniently located near major freeways for easy access to nearby cities. Just a short drive away, Oak Glen is famous for its apple orchards, seasonal festivals, and breathtaking fall foliage, creating a picturesque backdrop for your new home.

For those seeking spacious living, the area boasts an impressive selection of homes with three or more levels. These multi-story residences provide ample room for families to grow, with separate spaces for relaxation, entertainment, and work. Imagine enjoying serene evenings on your balcony, soaking in the stunning views, or hosting gatherings in your expansive living area. Each home is designed to offer a unique blend of comfort and style, ensuring that you find the perfect fit for your lifestyle.

Whether you're drawn to the natural beauty, the welcoming community, or the diverse housing options, Yucaipa, Calimesa, and Oak Glen are ready to welcome you home. Discover the charm and vibrancy of this remarkable region today!

Newest Yucaipa/Calimesa/Oak Glen (269) Homes with Three Or More Levels Stories

$460,000

13 Beds ⋅ 21 Baths ⋅ CV26219726 MLS ⋅ Active Status

**NEW CONSTRUCTION 55+ SENIOR LIVING COMMUNITY | YUCAIPA, CA | $460,000 PER CONDO** Discover a new approach to independent senior living in Yucaipa, combining modern design, spacious residences, and accessibility-minded features. This distinctive 55+ community offers the opportunity to own while enjoying the benefits of a thoughtfully planned community. **Approximately 90% complete**, the development presents an opportunity for early buyers to participate in its next chapter. Remaining construction and finishing work is anticipated to progress as initial units secure buyers and investment, with the goal of completing the community to match or exceed the renderings featured in the MLS photos. Designed for **13 spacious residences, each exceeding 900 square feet**, the planned layouts feature a bedroom, den/office, bathroom, kitchen, laundry area, living and dining spaces, and a private patio. The three-story property features a conveniently located elevator serving all levels, ADA-compliant bathrooms, and a large-capacity elevator designed to accommodate a gurney. Enjoy community amenities designed for connection and relaxation, including **two rooftop patios and an oversized gazebo**—ideal for family gatherings, entertaining, barbecues, light exercise, or peaceful morning meditation. Additional highlights include premium construction, contemporary finishes, a fully solar-powered community, and covered parking. Whether you are planning your next chapter or seeking a home that balances independence, comfort, and community, this Yucaipa property offers a unique opportunity to establish ownership within a developing 55+ community. **Own your space. Embrace your independence. Be part of something special—all for $460,000 per residence.** *Photo Disclaimer: Some listing photos are virtually staged, digitally rendered, or enhanced to illustrate proposed designs, finishes, and the anticipated completed appearance. Certain features and common areas may remain under construction. Images may not reflect current or final conditions. Buyers should independently verify all features, specifications, pricing, ownership details, and completion plans.*

12255 3rd, Yucaipa

$1,450,000

6 Beds ⋅ 3 Baths ⋅ IV26216004 MLS ⋅ Active Status

A Rare Oak Glen Property with Endless Possibilities! Set in Oak Glen on approximately 3.27 acres, this 4,528 sq ft, three-story home offers 6 bedrooms, 3 bathrooms, mountain views, mature trees, and a charming wraparound porch. The property includes beautifully landscaped lawns, tree-lined grounds, and a desirable corner-lot setting near Oak Glen Road. Inside, the home features custom woodwork, built-in storage, multiple fireplaces, and a family room/library that opens to the kitchen. The kitchen includes stainless-steel appliances and generous cabinetry, while the upper levels provide flexible bedroom, retreat, study, and guest-space options. A main-level bedroom adds additional convenience, while the primary suite includes a retreat/study area. The third level offers additional living or guest space with elevated mountain views. The outdoor setting is truly special, featuring mature Spruce, Sequoia, Aspen, Maple, and Dogwood trees, along with established apple trees and expansive grounds. Additional property features include a 3-car attached garage, private well, two Oak Glen water shares, septic system, two HVAC units, and a whole-house generator. Beyond its appeal as a private mountain residence, this property presents an exciting opportunity for buyers interested in exploring a short-term vacation rental, Airbnb, or intimate wedding and event venue. The current owners even celebrated their own wedding on the property, hosting approximately 200 guests against the beautiful Oak Glen mountain backdrop. With its expansive acreage, picturesque setting, and proximity to Oak Glen's popular attractions, the possibilities are worth exploring. Buyers should independently verify all applicable zoning, permits, licensing, and use restrictions. Ideally located approximately 0.1 miles from Snow-Line Orchard, 0.2 miles from ABurgerCompany, 0.4 miles from Los Rios Rancho and Farm Kitchen, and 0.6 miles from Oak Glen shops and attractions. Enjoy nearby orchards, cider, restaurants, hiking trails, and the Oak Glen Preserve, all with convenient access to Yucaipa, Redlands, and the surrounding Inland Empire.

39287 Pine, Yucaipa

$1,690,000

3 Beds ⋅ 4 Baths ⋅ IG26189600 MLS ⋅ Active Status

Tucked away on 3.5 acres of serene Oak Glen paradise, this private sanctuary offers a rare retreat where towering Cedar, Redwood, Oak, and Aspen trees embrace a home that masterfully bridges the gap between rugged mountain charm and contemporary sophistication. Accessed by a long, private gated driveway that promises total seclusion, the residence welcomes you with an awe-inspiring 31-foot-high ceiling, where rustic beams and an intricate Herringbone pattern create an unforgettable architectural statement. Inside, the home honors its unique heritage while incorporating thoughtful modern enhancements, including brand-new flooring, contemporary fixtures, updated baths, new roof, decks and stucco with attention to detail that elevates the comfort and design of its 3735 square feet of living space. At the heart of the home, a massive stone fireplace anchors the living area, creating an inviting gathering spot, while a wood stove on the main floor ensures cozy efficiency during chilly mountain evenings. Culinary enthusiasts will adore the European-style kitchen, complete with custom cabinetry, granite countertops, and top-tier appliances from Miele, Bosch, and Sub-Zero, all framed by a wall of windows that pulls the vibrant landscape inside. The lower level offers a sprawling 26x30 game room featuring its own entrance and a second floating hearth fireplace, providing the perfect venue for entertainment. The primary suite enjoys large windows for viewing, built-in storage and an updated bath with a new walk-in shower. Outside, wraparound viewing decks invite you to savor the breathtaking panoramas of city lights, tranquil meadows, and rugged mountains. Off the kitchen patio is a large detached room that could be a great office or gym. The garage has new epoxy flooring and a bath, along with a tall garage door. The covered entry parking is convenient for all seasons. Fruit trees dot the property, and the usable land invites you to bring your big ideas and future plans to live the good life in "The Glen."

39155 Harris, Oak Glen

$14,500,000

3 Beds ⋅ 5 Baths ⋅ IV25253989 MLS ⋅ Active Status

Step into a storybook setting... an extraordinary One-of-a-Kind Castle nestled in the beautiful mountain community of Oak Glen California. This magical Estate is tucked away in a forest yet conveniently located, offering easy access and feeling worlds apart from the city. Just 11 minutes from Yucaipa, about an hour from Lake Arrowhead and only 90 minutes from Los Angeles, it is a rare find that blends convenience with absolute privacy. Designed as a true Castle showplace, the property features an impressive grand entertaining Lounge... perfect for large gatherings, celebrations, or quiet evenings in regal style. With its timeless design and beautiful natural setting, this remarkable property offers a rare blend of nostalgia, unique character, and privacy. One of a Kind! Oh So Magical!! Attention Actors, Producers, Writers...Your Dream Come True Property. Approximately 6.73 Acres.

38838 Birch Creek, Oak Glen

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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.