Upland Homes with Craftsman Style

Upland Homes with Craftsman Style

Welcome to Upland, California—a hidden gem nestled in the heart of San Bernardino County. With its picturesque mountain views and vibrant community spirit, Upland offers a unique blend of suburban charm and accessibility to urban amenities. Known for its rich history and friendly neighborhoods, this city is a perfect place for families, professionals, and retirees alike.

One of the standout features of Upland is its stunning Craftsman-style homes. These architectural treasures reflect a commitment to quality craftsmanship and timeless design, characterized by their wide porches, exposed rafters, and intricate woodwork. As you stroll through Upland’s tree-lined streets, you’ll be captivated by the warm, inviting aesthetics of these homes, which often feature built-in bookcases, coffered ceilings, and beautiful hardwood floors.

Living in a Craftsman home in Upland means embracing a lifestyle that values both comfort and character. Many of these residences are situated on spacious lots, providing ample outdoor space for gardening, entertaining, or simply enjoying the California sunshine. The community is also home to a variety of parks, schools, and local shops, making it easy to enjoy a balanced lifestyle.

Whether you’re drawn to Upland for its scenic beauty, its vibrant community, or the allure of Craftsman-style architecture, you’ll find a welcoming atmosphere that feels like home. Explore the possibilities in Upland, where your dream home awaits amidst stunning landscapes and a rich cultural heritage.

Newest Upland Homes with Craftsman Style

$825,000
3 Beds ⋅ 2 Baths ⋅ CV26150783 MLS
Step back in time in this turnkey, single-story Craftsman masterpiece! Perfectly preserving its timeless architectural heritage, this move-in-ready home welcomes you with a classic, sweeping front porch. Inside, beautifully restored original hardwood floors flow seamlessly through bright spaces illuminated by authentic Craftsman-style windows. Every historic detail has been lovingly brought back to life, including the original interior doors, thick baseboards, casing, and a grand, cozy fireplace that serves as the heart of the living space. The expansive backyard offers a private oasis with unlimited potential for entertaining, dining alfresco, or dynamic landscaping. Convenience is maximized by a detached 2-car garage featuring accessible rear alley access. Situated in a highly desirable Upland neighborhood, this property offers an unparalleled walkable lifestyle. Stroll easily into vibrant Downtown Upland to enjoy fine dining, local boutiques, and iconic community events like the annual Lemon Festival and Irish Festival. Benefit from top-tier, award-winning local schools, quick access to the Interstate 10 freeway, and close proximity to both historic Route 66 and San Antonio Regional Hospital. This rare blend of historic charm and urban convenience won't last long—schedule your private showing today!

693 N Euclid Avenue, Upland
$850,000
CV26136118 MLS
Welcome to 560 N. 2nd Avenue—a truly special home with an attached ADU in the heart of Historic Downtown Upland. Rich in character and thoughtfully updated, this beautifully maintained Craftsman offers the rare combination of timeless charm, flexible living space, and investment potential—all just moments from restaurants, coffee shops, breweries, boutique shopping, the weekly farmers market, and Upland’s beloved annual Holiday Parade and year-round downtown festivities. Situated on an approximately 7,500-square-foot lot, the property features a spacious front residence plus an attached ADU with its own private entrance, making it ideal for multi-generational living, rental income, a private guest suite, or a dedicated home office. The front main house offers two spacious bedrooms, one beautifully updated bathroom, an open-concept living and dining area, and a huge upstairs loft that is set up to add an additional bathroom. This versatile space could easily serve as a third bedroom, game room, office, or creative studio. Hardwood flooring, granite countertops, stainless steel appliances, updated cabinetry, recessed lighting, a large laundry room, and central heating and air conditioning blend historic character with modern comfort. The attached ADU features one bedroom, one bathroom, its own kitchen, living area, private entrance, and separate gas and electric meters, creating an exceptional opportunity for extended family, guests, or supplemental rental income. Car enthusiasts will appreciate the impressive detached oversized four-car tandem garage and expansive alley-access driveway, providing abundant off-street parking with room for multiple vehicles, boats, RVs, recreational toys, or future workshop possibilities. An additional front driveway provides even more parking and convenience. The spacious backyard is perfect for entertaining, offering plenty of room for BBQs and gatherings. Whether you’re relaxing around the fire pit, lounging beneath the pergola, or taking advantage of the expansive lawn, the outdoor space offers the perfect balance of hardscape and green space for year-round enjoyment. Whether you’re searching for your forever home, an income-producing property, or the perfect setup for extended family, this one-of-a-kind property truly checks nearly every box.

560 N 2nd Avenue, Upland
$850,000
3 Beds ⋅ 2 Baths ⋅ CV26135979 MLS
Welcome to 560 N. 2nd Avenue—a truly special home with an attached ADU in the heart of Historic Downtown Upland. Rich in character and thoughtfully updated, this beautifully maintained Craftsman offers the rare combination of timeless charm, flexible living space, and investment potential—all just moments from restaurants, coffee shops, breweries, boutique shopping, the weekly farmers market, and Upland’s beloved annual Holiday Parade and year-round downtown festivities. Situated on an approximately 7,500-square-foot lot, the property features a spacious front residence plus an attached ADU with its own private entrance, making it ideal for multi-generational living, rental income, a private guest suite, or a dedicated home office. The front main house offers two spacious bedrooms, one beautifully updated bathroom, an open-concept living and dining area, and a huge upstairs loft that is set up to add an additional bathroom. This versatile space could easily serve as a third bedroom, game room, office, or creative studio. Hardwood flooring, granite countertops, stainless steel appliances, updated cabinetry, recessed lighting, a large laundry room, and central heating and air conditioning blend historic character with modern comfort. The attached ADU features one bedroom, one bathroom, its own kitchen, living area, private entrance, and separate gas and electric meters, creating an exceptional opportunity for extended family, guests, or supplemental rental income. Car enthusiasts will appreciate the impressive detached oversized four-car tandem garage and expansive alley-access driveway, providing abundant off-street parking with room for multiple vehicles, boats, RVs, recreational toys, or future workshop possibilities. An additional front driveway provides even more parking and convenience. The spacious backyard is perfect for entertaining, offering plenty of room for BBQs and gatherings. Whether you’re relaxing around the fire pit, lounging beneath the pergola, or taking advantage of the expansive lawn, the outdoor space offers the perfect balance of hardscape and green space for year-round enjoyment. Whether you’re searching for your forever home, an income-producing property, or the perfect setup for extended family, this one-of-a-kind property truly checks nearly every box.

560 N 2nd Avenue, Upland
$1,180,000
3 Beds ⋅ 2 Baths ⋅ CV26140002 MLS
Imagine arriving home each evening and feeling as though you've escaped to your own private resort. Nestled on a beautifully curated 16,400± sq. ft. lot in prestigious San Antonio Heights, this thoughtfully reimagined 1922 Craftsman is more than a home—it's a private retreat designed for unforgettable gatherings and everyday living. The resort-inspired grounds are truly exceptional, featuring multiple outdoor entertaining spaces, a sprawling TREX deck beneath a majestic pepper tree, pergola-covered patio, BBQ station, tranquil water feature, greenhouse with electricity and water, raised irrigated garden beds, and a flourishing orchard with avocado, citrus, apple, pear, and apricot trees. Framed by breathtaking mountain views, the setting feels more like a private garden estate than a traditional backyard. Designed for both entertaining and adventure, the property also offers RV parking with 50-amp electrical service, water hookup, and dump station, a finished carriage house garage, bonus workshop with electricity, dedicated dog wash station, pet relief area, and a charming garden powder room that adds both convenience and character to outdoor gatherings. Inside, timeless Craftsman charm blends seamlessly with modern amenities. Imported hardwood floors, marble countertops, Smart Home technology compatible with Google Assistant and Alexa, customizable lighting, built-in speakers, Ethernet wiring, paid solar, and a private lounge complete with a wet bar, ice maker, bottle chiller, bar dishwasher, and sink create an ideal space for entertaining. One of the three bedrooms is currently configured as a warm and inviting library, offering flexibility for a home office, guest room, or reading retreat. Extensive improvements completed between 2021 and 2023 include a new roof, 200-amp electrical panel, HVAC system, plumbing, sewer laterals, tankless water heater, and major electrical upgrades, providing exceptional peace of mind. As an added benefit, ownership includes a partial share in the San Antonio Water Company. This is more than a beautiful home—it's a lifestyle. A place where friends gather, gardens flourish, memories are made, and every day feels like a getaway.

895 W 23rd, Upland
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Based on information from CRISNet MLS as of All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The listing broker's offer of compensation is made only to participants of the MLS where the listing is filed.