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 vibrant area is renowned for its picturesque landscapes, rich agricultural heritage, and a warm community spirit that makes it a truly delightful place to call home.

Yucaipa, with its charming downtown and proximity to the San Bernardino Mountains, offers a perfect blend of suburban tranquility and outdoor adventure. Residents enjoy an array of recreational activities, from hiking the scenic trails of the surrounding mountains to exploring the lush orchards and farms that define the region. Calimesa, with its serene neighborhoods and beautiful parks, is ideal for families seeking a peaceful lifestyle, while Oak Glen boasts stunning apple orchards and seasonal festivals that celebrate the harvest.

For those in search of spacious living, this region offers a variety of homes featuring three or more levels. These multi-story residences provide ample space for families, with the added benefit of stunning views and diverse floor plans. Imagine waking up to breathtaking mountain vistas or enjoying sunset views from your private balcony. Whether you’re entertaining guests or cherishing quiet family moments, these homes are designed to elevate your living experience.

With its unique blend of natural beauty, community charm, and spacious homes, Yucaipa, Calimesa, and Oak Glen is not just a place to live, but a lifestyle to embrace. Discover your dream home in this captivating region, where every day feels like a retreat. Come and experience the warmth and charm of this remarkable area today!

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

$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

$599,000

5 Beds ⋅ 3 Baths ⋅ IG26161154 MLS ⋅ Active Under Contract Status

Nestled in the highly desirable upper Yucaipa area, this beautifully maintained custom tri-level home offers exceptional curb appeal, mountain views, and a spacious lot of over 1/4 acre. A long driveway, mature landscaping, RV parking, and a two-car attached garage create an impression while providing ample space for vehicles, toys, and guests. Inside, you'll find a light-filled interior featuring tasteful neutral colors, fresh interior paint, new carpet, and classic plantation shutters. The thoughtfully designed floor plan offers flexibility for a variety of lifestyles. The main level serves as the heart of the home with an inviting living room, formal dining area, and well-appointed kitchen—perfect for everyday living and entertaining. The lower level features a versatile bedroom complete with a wet bar, making it ideal as a guest suite, family room, game room, or private home office. A convenient laundry room and updated half bath complete this level. Upstairs, retreat to the spacious primary suite featuring a private balcony where you can enjoy peaceful mornings and beautiful views. The large primary bath includes dual vanities, a soaking tub, separate shower, and generous closet. Three additional bedrooms and a guest bathroom provide plenty of room for family and guests, with the guest bath also beautifully remodeled. Step outside to enjoy the expansive yard with lush lawn, mature trees, attractive landscaping, and plenty of room to entertain, garden, or even add a pool. The combination of privacy, usable outdoor space, and scenic surroundings makes this property truly special. With its custom design, flexible floor plan, tasteful updates, oversized lot, RV parking, and sought-after upper Yucaipa location, this home offers the perfect blend of comfort, functionality, and timeless appeal.

11666 Madison Street, Yucaipa

$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.