Upland (690) Homes with Two Levels Stories

Welcome to Upland, California—a charming city nestled in the heart of San Bernardino County, where the stunning San Gabriel Mountains serve as a picturesque backdrop to everyday life. Known for its warm climate, vibrant community, and rich history, Upland is a delightful blend of suburban tranquility and urban convenience. With its tree-lined streets, inviting parks, and a variety of shopping and dining options, Upland offers an idyllic environment for families, professionals, and retirees alike.

One of the most appealing aspects of Upland's real estate market is the availability of two-story homes. These multi-level residences provide an ideal balance of space and functionality, making them perfect for growing families or those who enjoy entertaining. With ample room for personalization, two-level homes often feature spacious living areas, well-appointed kitchens, and inviting outdoor spaces that enhance the California lifestyle. Imagine hosting gatherings in your expansive backyard or enjoying quiet evenings on your balcony, soaking in the stunning views of the surrounding mountains.

Upland’s two-story homes often come equipped with modern amenities and thoughtful designs, including open floor plans, luxurious master suites, and energy-efficient features. The city's diverse neighborhoods cater to a variety of tastes, ensuring you'll find the perfect home that meets your needs and desires. Whether you’re looking for a cozy family retreat or a stylish modern abode, Upland’s two-story homes offer an exceptional opportunity to experience the best of California living. Discover your dream home in Upland today, and embrace a lifestyle filled with comfort, community, and breathtaking scenery!

Newest Upland (690) Homes with Two Levels Stories

$1,268,888

5 Beds ⋅ 3 Baths ⋅ CV26215902 MLS ⋅ Active Status

Beautiful spacious 5 bedroom, 3 bath North Upland home. Thoughtfully upgraded with friends and family in mind. Enjoy the incredible backyard with commercial wood fired pizza oven, Chefs BBQ island with ice maker and beverage fridge and huge covered patio. 2 car detached garage is insulated and air conditioned (possible ADU) + a 2 car covered carport. Additional features include updated master and guest bath, new doors throughout, updated plumbing, barn workshop, 30 AMP for RV, long gated driveway, and so much more. This is a must see!

1710 Coolcrest Avenue, Upland

$1,495,000

4 Beds ⋅ 3 Baths ⋅ CV26215493 MLS ⋅ Active Status

Where luxury living meets the warmth and comfort of home, 2429 Cliff Road truly stands apart. Nestled in the highly sought-after San Antonio Heights community of North Upland. This beautifully maintained, turnkey residence offers exceptional style, functionality, privacy, and timeless charm. Set on an expansive corner lot, the property features a grand circular driveway, separate extended RV driveway, RV parking, beautifully landscaped grounds, and a home gracefully positioned back from the street for privacy and an impressive sense of arrival. Inside, soaring ceilings, rich engineered wood-plank flooring, abundant natural light, and an open, thoughtfully designed floor plan create an inviting atmosphere. Oversized sliding glass doors showcase the spectacular backyard and seamlessly connect indoor and outdoor living. The backyard is a private resort designed for entertaining and unforgettable gatherings. Enjoy a sparkling pool and spa with Baja shelf, built-in table seating, dramatic rock waterfall and water slide with grotto, plus a spectacular custom Tiki hut Palapa with a wonderfully equipped outdoor BBQ kitchen. This exceptional outdoor oasis is perfect for entertaining or relaxing in the ultimate Southern California lifestyle. The multi-level floor plan provides both spaciousness and privacy. The generously sized primary suite occupies its own private wing, while three additional oversized bedrooms and a beautifully appointed full bath are located upstairs, offering exceptional space for family, guests, or a home office. At the heart of the home, the chef-inspired kitchen is ideally positioned between the dining and family rooms and features high-end appliances, extensive custom cabinetry, generous workspace, and an ideal entertaining layout. The oversized garage offers impressive ceiling height and abundant space for vehicles, hobbies, toys or workshop. The long, separate RV driveway extends toward the rear of the property, offering potential for an ADU, RV garage, workshop, or additional recreational space—buyer to verify feasibility and requirements with the appropriate agencies. Highlights include PAID-OFF SOLAR, ¼ WATER SHARES, RV PARKING, circular driveway, expansive lot. Ideally located minutes from The Colonies Crossroads, premier shopping, dining, entertainment, parks, hiking trails, highly regarded schools, and convenient freeway access, 2429 Cliff Road offers the space, privacy, amenities, and lifestyle that define North Upland living.

2429 Cliff Road, Upland

$829,800

4 Beds ⋅ 3 Baths ⋅ CV26215391 MLS ⋅ Active Status

Upland Hills Estates Gated Community! Largest model. Professional photos and updated description to follow.

1476 Augusta Drive, Upland

$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

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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.