Upland Homes with Two Levels Stories

Welcome to Upland, California, a charming city nestled in the heart of San Bernardino County, where suburban comfort meets the beauty of the San Gabriel Mountains. Known for its picturesque neighborhoods, Upland boasts a rich history and a vibrant community spirit. With a delightful mix of parks, shopping centers, and dining options, residents enjoy a lifestyle that balances tranquility with convenience.

One of the standout features of Upland is its diverse array of homes, particularly those with two-level stories. These multi-story residences offer not only spacious living but also the opportunity for unique layouts that cater to various lifestyles. Imagine waking up in a beautifully designed master suite on the upper level, with panoramic views of the surrounding mountains, while the lower level serves as a welcoming space for family gatherings or entertaining friends. The two-level homes in Upland often come with modern amenities, open floor plans, and ample outdoor spaces, perfect for enjoying the California sunshine.

Upland’s neighborhoods are characterized by tree-lined streets and a strong sense of community. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find that Upland’s two-level homes offer the perfect blend of comfort and style. With excellent schools, recreational facilities, and a variety of local events throughout the year, Upland is not just a place to live; it’s a place to thrive. Explore the possibilities of two-level living in Upland and discover your dream home in this beautiful city!

Newest Upland Homes with Two Levels Stories

$1,650,000

7 Beds ⋅ 5 Baths ⋅ PW26211131 MLS ⋅ Active Status

Located at the end of a quiet cul de sac in The Colonies neighborhood of Upland, this beautifully renovated luxury home offers 7 bedrooms and 5 bathrooms, including an attached ADU with its own private entrance. High ceilings, abundant natural light, and recessed lighting create an open feel throughout the main living areas. The kitchen and family room flow naturally together, with a real flame electric fireplace adding warmth to the space. At the heart of the kitchen is an oversized custom marble island, complemented by generous cabinetry, a dedicated coffee area, and a walk-in pantry that provides additional storage. One of the home's standout features is the attached ADU, offering a versatile option for multigenerational living, extended family, guests, or potential rental income. With its own private entrance, the ADU includes a bedroom, two bathrooms with standing showers, a kitchenette, and a spacious living area that can also function as a second bedroom. The kitchenette includes a refrigerator, electric cooktop, and farmhouse sink, while a private laundry area and additional storage add convenience. Upstairs, the spacious primary suite offers plenty of room and includes a balcony overlooking the landscaped backyard. The primary bathroom features dual sinks, a soaking tub, separate shower, water closet, and two walk-in closets. The additional bedrooms are generously sized and provide flexibility for family, guests, or other uses. The upstairs laundry room offers added convenience with a sink and counter space. Outside, the fully landscaped backyard is designed for entertaining and enjoying Southern California living. A built-in firepit creates a natural gathering space, while the covered patio with two ceiling fans provides a comfortable setting for outdoor dining, relaxing, and entertaining. Extensively renovated and thoughtfully customized, this Colonies home combines the scale and finish of a luxury property with the versatility of an attached private living space. Broker and agents do not represent or guarantee the accuracy of the square footage, income, expenses, condition, development potential, bedroom/ bathroom count, lot size or lot lines, dimensions, permitted or non-permitted spaces, or school eligibility. Buyer is advised to independently verify the accuracy of all information with appropriate professionals. There are no warranties or guarantees, buyer to rely solely on his/her/their own findings.

1530 Crestar Court, Upland

$1,950,000

4 Beds ⋅ 5 Baths ⋅ IV26210827 MLS ⋅ Active Status

ENTERTAINERS DREAM HOME!!! This gorgeous corner lot home in the highly desirable area of Upland - Offering a perfect blend of inviting living areas, tasteful elegance and an abundance of natural light giving a radiant warmth all throughout the day. This double level layout welcomes you into an attractive entrance which flows beautifully into the family / dining area which then opens into the gourmet kitchen / family room area. The gorgeous kitchen features stainless steel appliances, granite counter-tops and stunning custom cabinets. There is one bedroom and an office downstairs and the remaining bedrooms are situated upstairs and are all generous in size. The upstairs is enriched with an oversized entertainment / great room. The back terrace is designed for enjoyment of every season accented with an extensive patio. The shimmering pool is welcoming for these hot days and the jacuzzi to enjoy at the end of the day! The house was built by a custom home builder with specific attention to every detail and then some. This amazing home is ready for the perfect family to begin making memories to last a lifetime!!

421 E 21st, Upland

$720,000

3 Beds ⋅ 3 Baths ⋅ AR26210572 MLS ⋅ Active Status

The well maintained family home (Planned Unit Development) in the gated Grovelands Community features 3 Bedrooms+Den(Downstairs)+Loft and 3 Bathrooms - the house can be easily converted to a 5 Bedroom home if need. The bright open living/dining room has a fireplace and ceiling fan, kitchen with recessed lighting, island, pantry and downstairs den could be converted to a guest bedroom. The spacious primary bedroom has double doors, high valted ceiling, ceiling fan and bathroom with large walk-in closet, dual sinks, soaking tub and separate shower stall. Wonderful community offers gated entrance, guest parkings, swimming pool and children/s plan area. Other features include north facing with mountain view, security alarm system, individual laundry room upstairs, 2-car attached garage with direct access to the kitchen, two additional parking spaces on the driveway, large patio in private backyard with frut trees and automatic sprinkler system. Near Downtown Upland, Library, Civic Center and San Antonio Regional Hospital - situated conveniently close to dining, shopping and freeways. The perfect home for entertaining and California living. Move in and enjoy!

1430 Orange Tree Lane, Upland

$825,000

3 Beds ⋅ 3 Baths ⋅ CV26209760 MLS ⋅ Active Status

Nestled within the gated community of Upland Hills Country Club, this beautifully remodeled home offers a serene setting, sweeping golf course views, and a thoughtfully designed floor plan. Positioned to capture mountain views to the north and peaceful golf course views to the south, the home enjoys a rare combination of natural beauty, privacy, and convenience. The backyard is a private garden-like retreat, featuring covered patio area, manicured lawn, and mature maple trees that create a tranquil outdoor setting overlooking the golf course. Inside, the functional floor plan offers comfortable living spaces with soaring ceilings and an abundance of natural light. The remodeled kitchen and adjacent den are perfectly positioned to take in the golf course views, while the formal living areas provide an inviting space for entertaining and everyday living. Upstairs, a versatile loft provides additional living or workspace, while the spacious primary suite offers a peaceful retreat overlooking the golf course. The primary bathroom has been remodeled and features generous proportions and a large walk-in closet. Additional improvements include remodeled bathrooms, attractive flooring throughout, and a newer HVAC system. The attached two-car garage provides exceptional storage, along with a convenient utility sink. The only shared wall with the neighboring residence is at the garage, while the remainder of the home is surrounded by its own side and rear yards, allowing you to walk completely around the residence. Upland Hills Country Club offers an exceptional collection of amenities, including three sparkling pools, tennis courts, pickleball courts, and beautifully maintained community grounds. The HOA also covers a wide range of maintenance, amenities, and utilities, providing a convenient, low-maintenance lifestyle. Ideally located in the Upland area with easy access to shopping, dining, recreation, and major transportation routes, this is a wonderful opportunity to enjoy comfortable living in a peaceful golf course community. Information deemed reliable, buyer to verify.

1464 Augusta, Upland

$844,888

5 Beds ⋅ 3 Baths ⋅ CV26208069 MLS ⋅ Active Status

Welcome to 1527 Fairwood Way — a two-story North Upland pool home offering 4 bedrooms, 3 bathrooms, and approximately 2,095 square feet on a 7,500 square foot lot. Vaulted ceilings give the main living space real volume and light, and the floor plan is functional and well-proportioned, with generous room sizes that work as easily for quiet weeknights as they do for hosting. A downstairs bonus room with a closet adds flexible space for a home office, guest room, or gym — buyer to verify permits. Out back, the pool was replastered in July 2026, anchoring a generous yard with plenty of room left to shape. This one is being offered in its present condition, and it's looking for a buyer who knows how far a little love can go. Bring your paint, your ideas, and your contractor. Cosmetic updates here go a long way, and the reward is a freshly replastered pool on a 7,500 square foot lot in an established Upland neighborhood — the kind of opportunity that rarely comes available in this pocket. Minutes to shopping, dining, neighborhood parks, and quick access to the 210 and 10. Investors and owner-occupants alike — come see the potential.

1527 Fairwood Way, Upland

$1,399,000

5 Beds ⋅ 5 Baths ⋅ 26990659 MLS ⋅ Active Status

Welcome to 426 Citrus Union Street, a two-story home of about 3,925 square feet in Upland's Montrose neighborhood. The residence offers five bedrooms, four full bathrooms, a powder room, and an upstairs loft. Ceilings are high throughout, the plan is square and practical, and natural light reaches the main living areas. The property sits south of the 210 Freeway in the Upland Unified School District. Daily errands are close along Foothill Boulevard and at nearby parks. Colonies Crossroads, Victoria Gardens, and Ontario Mills cover larger shopping and dining, with Ontario International Airport a straightforward drive. Features include central air, plantation shutters, recessed lighting, extra linen storage, arched openings, upgraded laminate flooring, and an attached three-car garage. A water softener is in place. On the first floor, a bright living room opens toward the kitchen and dining room. The kitchen has maple cabinets, granite counters, stainless-steel appliances, an oversized island, and a large walk-in pantry. The family room has multiple windows. A bedroom suite and powder room on this level can serve as a guest room or office. The second floor holds four bedrooms and a laundry room with cabinets and a utility sink. The primary suite has a sitting area and a large walk-in closet. The primary bath includes two separate vanities, a partitioned toilet with storage, a shower, and a soaking tub. Two secondary bedrooms share a dual-access (Jack and Jill) bathroom. The loft works as an office or media space. The backyard and patio look toward the mountains, with a shaded seating area and fruit trees including mulberry, peach, and sweet pomelo. A community park nearby has seating and a pet waste station.

426 Citrus Union Street, Upland

$715,000

4 Beds ⋅ 3 Baths ⋅ PW26204368 MLS ⋅ Active Status

Welcome to this stunning, turn-key residence located in the highly desirable, gated Heartland community of Upland! Boasting 1,972 square feet of beautifully designed living space, this home blends the spacious feel of a single-family property with the low-maintenance lifestyle of a premier condominium. Steeped in natural light, the main front entryway opens into a bright, open-concept floor plan that seamlessly connects the main living room and dining area perfect for both daily living and effortless entertaining. The heart of the home is the chef-ready kitchen, which features a direct service entrance from the attached 2-car garage, making grocery trips a breeze. With 4 generously sized bedrooms and 2.5 bathrooms, this split-level layout offers maximum privacy and versatility for families, guests, or a dedicated home office. Enjoy the peace of mind that comes with living in a secure, well-maintained gated community with a low monthly HOA fee. Conveniently situated near top-rated schools, local parks, shopping, and dining, this Upland gem is ready for its next chapter.

349 Settlers Rd, Upland

$1,375,000

4 Beds ⋅ 3 Baths ⋅ CV26205010 MLS ⋅ Active Status

BEAUTIFULLY PRESERVED HISTORICAL ENGLISH REVIVAL Built in 1929 is on the MILLS ACT which affords it SUBSTANIAL TAX ADVANTAGES The Property showcases Timeless Old-World Charm, with unmistakable French Architectural Influences. From its Steeply Pitched Gable Roof and Storybook Silhouette to the Elegant Arched Doorways and Original Detailing. This Enchanting Home evokes the Romantic Ambiance of a European countryside Manor. Whether viewed as a classic example of Tudor/English Revival or through its Refined French Styling, this two-story residence offers a rare blend of Architectural Heritage and Artistic Craftsmanship. Circular Motor Court and Fountain greet you and your guests. Entry with Grand Staircase. Large rooms. Living Room with Fireplace and French Door to Sun room, Formal Dining Room. Remodeled Gourmet Kitchen with Butler's Pantry. Rotunda Breakfast Room with Windows to the Wonderful, Landscaped Backyard. Downstairs Library Existing Two Room Recording Studio/Office or possible ADU attached to a Two Car Garage gives it endless possibilities. Please call for more details. Truly a Country Estate that sits on a large 11,250 approx.sq.ft.lot.

1447 N Euclid, Upland

$889,000

3 Beds ⋅ 3 Baths ⋅ CV26205903 MLS ⋅ Coming Soon Status

Beautifully remodeled home in desirable North Upland with mountain views, offering 3 bedrooms, 2.5 bathrooms, indoor laundry room, 1,559 square feet of living space on 5,356-square-foot lot. Large private backyard featuring a covered patio—perfect for entertaining, relaxing, or gardening. Upland Unified School District. Located right across a neighborhood park. Near shopping, dining, and recreation. Move-in-ready home with quality upgrades and an exceptional location.

2280 Ash, Upland

$949,990

4 Beds ⋅ 3 Baths ⋅ IG26202600 MLS ⋅ Active Status

Welcome to this beautifully remodeled 4-bedroom, 2.5-bathroom home situated on a desirable corner lot in one of Upland’s most sought-after neighborhoods! Offering approximately 2,194 square feet of living space, this move-in-ready home has been thoughtfully updated with brand-new flooring throughout, fresh interior and exterior paint, updated kitchen cabinets, new kitchen and bathroom countertops, brand-new stainless steel appliances, and energy-efficient dual-pane windows. Inside, you’ll find a bright and functional floor plan with multiple living areas ideal for everyday living and entertaining. The updated kitchen flows seamlessly into the main living spaces, creating the perfect setting for family gatherings or hosting guests. Upstairs, the generously sized bedrooms include a large primary suite with its own private balcony—the perfect place to enjoy your morning coffee or unwind at the end of the day. Situated on a generous corner lot, the backyard offers plenty of room for entertaining, weekend BBQs, gardening, or simply relaxing. The property also features fresh sod, adding to the home’s clean curb appeal and refreshed exterior. Located in a quiet, well-established neighborhood with tree-lined streets and pride of ownership throughout, the home is just minutes from parks, schools, shopping, dining, and convenient access to the 10 and 210 freeways. With no HOA, a low tax rate, tasteful updates throughout, and a great Upland location, this home checks all the boxes. Don’t miss your opportunity to make it yours!

1432 Purdue Street, Upland

$648,000

3 Beds ⋅ 3 Baths ⋅ IG26202651 MLS ⋅ Active Status

WOW!!! DETACHED HOME IN GATED COMMUNITY!! Welcome to Harvest at Upland, a beautifully maintained gated community in North Upland where thoughtful home design meets resort-style living. Tucked away from the street within the community, this 3-bedroom, 2.5-bathroom DETACHED home offers a more peaceful setting along with an open-concept layout that connects the kitchen, dining, and living spaces for easy everyday living and entertaining. The kitchen features stainless steel appliances and an island with seating, opening directly to the dining and living areas. The kitchen also provides access to a private enclosed patio, creating a convenient spot to enjoy your morning coffee or some fresh air. Upstairs, all three bedrooms are situated alongside a versatile loft that can be used as a home office, play space, or additional hangout spot. The primary suite includes dual sinks and a walk-in shower. A stackable washer and dryer are tucked away in an upstairs closet, for added convenience. Additional features include solar, to be assumed by the buyer, a tankless water heater, ceiling fans, recessed lighting throughout, and upgraded roller shades on the upstairs windows. The attached two-car garage provides direct access to the home. One of the standout features of living at Harvest is the collection of amenities available just outside your front door. Residents enjoy a large pool and spa, fitness center, clubhouse, dog park, playground, two neighborhood gardens, ping-pong and recreation room, outdoor fireplace and conservation areas, and BBQ and entertaining spaces. The beautifully landscaped community creates plenty of opportunities to get outside, gather with neighbors, or simply enjoy the surroundings. Located in North Upland with convenient access to shopping, dining, entertainment, parks and recreation, including Colonies Crossroads, Montclair Place, Ontario Mills and Claremont Village. The Metrolink station and 210 and 10 freeways are also nearby, making it easy to connect throughout the Inland Empire and surrounding areas. Nearby higher-education destinations include the Claremont Colleges and University of La Verne. The home is served by Upland Unified School District. The community setting offers plenty to look at, from the surrounding hills and mountains to airplanes overhead and even 4th of July fireworks.

817 Cranberry Way, Upland

$1,189,000

5 Beds ⋅ 3 Baths ⋅ PW26203965 MLS ⋅ Active Status

Updated, turnkey home with an attached ADU. Welcome to a beautifully updated home offering exceptional versatility and endless potential for multi-generational living or rental income. The main home features 3 bedrooms and 2 bathrooms, highlighted by an updated kitchen with real wood cabinetry, a newly remodeled hallway bathroom, new cordless blinds, upgraded lighting, upgraded 200 amp electrical panel, upgraded plumbing, laundry room and lots more. The home layout offers unique flexibility that's hard to find. You can open the shared wall and close the stairway access from the ADU to make a 5 bedroom main home. That still leaves you a studio with a kitchen and bathroom perfect for aging parents, guests, or rental income! The almost 10,000 sqft lot can still accommodate a full, separate ADU (Buyer to verify). Outside, you'll find a large driveway and a spacious backyard, providing plenty of space for entertaining, relaxing, family gatherings, or enjoying the outdoors. With its thoughtful updates, functional layout, attached ADU, generous parking, and spacious yard, this property offers a unique opportunity you won't want to miss. Built-in peace of mind with regular preventative maintenance, including annual water heater flushes, routine HVAC servicing, and ongoing quarterly pest control

236 W Dayton, Upland

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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.