Jake Middling, owner
One Cherry, LLC is a premier residential real estate investment and property holding company operating throughout Washington, Arizona, and Florida—three of the nation’s most desirable and rapidly growing housing markets. Our mission is simple: identify undervalued real estate opportunities, execute strategic renovations and modern upgrades, and create high-quality homes that generate lasting value for homeowners, communities, and investment partners alike.
Through disciplined acquisitions, conservative underwriting, and hands-on project management, One Cherry, LLC has established a reputation for transforming overlooked properties into desirable, income-producing assets. Our portfolio includes residential rentals, fix-and-flip projects, furnished executive housing, and professionally managed short-term vacation rentals.
For banks, private lenders, and investment partners, One Cherry, LLC represents a dependable and experienced borrower with a proven track record of successful acquisitions, responsible asset management, and measurable appreciation. Every project is approached with a focus on protecting capital, maximizing returns, and maintaining the highest standards of quality and accountability.
In addition to our traditional real estate holdings, One Cherry, LLC owns and operates premium short-term rental properties in some of the country’s most sought-after vacation destinations. Our Arizona portfolio features two exceptionally located vacation homes in Scottsdale, positioned just minutes from Old Town Scottsdale, world-class golf courses, spring training facilities, fine dining, nightlife, and premier shopping. These properties consistently attract vacationers, business travelers, golf enthusiasts, and seasonal visitors seeking a luxury Arizona experience.
In Florida, our portfolio includes a stunning waterfront vacation home in Cape Coral situated directly on a recreational lake, offering guests immediate access to boating, fishing, kayaking, paddleboarding, and a variety of water sports. The property’s unique waterfront setting, combined with Florida’s year-round sunshine, creates a highly desirable destination for families, outdoor enthusiasts, and vacation travelers.
For corporate clients, traveling professionals, healthcare workers, contractors, and relocating families, we also offer fully furnished, move-in-ready housing solutions throughout our markets. Our furnished residences provide the comfort and convenience of home without the burden of purchasing furniture, signing lengthy leases, or navigating the challenges of relocation.
At One Cherry, LLC, we believe exceptional real estate creates value for everyone involved—from the financial institutions and lending partners who help fund opportunities, to the guests, tenants, and families who ultimately call our properties home. Through thoughtful investment, strategic management, and an unwavering commitment to quality, we continue to build a portfolio that delivers both financial performance and outstanding living experiences.
Leadership & Experience
One Cherry, LLC is led by its Owner and President, who brings more than 22 years of hands-on experience in real estate acquisition, property management, residential redevelopment, construction, and investment strategy. Throughout his career, he has successfully purchased, renovated, managed, leased, and sold a wide range of residential and commercial real estate assets, providing a comprehensive understanding of every stage of the investment lifecycle.
In addition to his residential expertise, he has extensive experience overseeing and actively managing a large commercial real estate portfolio comprised primarily of neighborhood retail centers, strip malls, and single-tenant occupied properties. He continues to manage these assets today, maintaining direct involvement in leasing, tenant relations, capital improvement planning, financial performance, property operations, and long-term investment strategy. This ongoing experience provides valuable insight into market trends, asset preservation, cash flow optimization, and value creation across multiple real estate sectors.
Raised in the shadow of a highly successful real estate investor, builder, and entrepreneur, he was immersed in the industry from an early age. Real estate, construction, and business ownership have been part of his family’s heritage for four generations, creating a foundation of knowledge and experience that continues to shape the company’s approach today.
This multi-generational background, combined with more than two decades of personal experience, allows One Cherry, LLC to identify opportunities others overlook, accurately assess risk, manage complex renovation projects, and maximize the value of every asset it acquires. The company is particularly recognized for transforming outdated and neglected properties into highly desirable homes featuring luxury kitchens, spa-inspired bathrooms, modern finishes, and exceptional craftsmanship.
Today, One Cherry, LLC continues this legacy by acquiring undervalued properties, revitalizing neighborhoods, operating high-performing rental and vacation properties, and delivering strong, reliable results for lending partners, investors, tenants, and guests alike.