The Union Street Bungalows offers a unique opportunity to acquire a fully renovated, historically designated 8-unit bungalow-style property in the core of Little Italy—one of San Diego’s most dynamic and high-demand urban neighborhoods. The asset is currently operated as a short-term rental property and is supported by a transferable Conditional Use Permit (CUP), a highly limited entitlement within the neighborhood. With new approvals no longer being issued in Little Italy, this designation represents a meaningful barrier to entry and a significant advantage over competing properties. In addition, the property is subject to a Mills Act contract, which provides a reduced property tax basis tied to its historic designation. This structure results in materially lower operating expenses compared to similar assets, improving overall investment performance. The property was thoughtfully revitalized under the direction of Jonathan Segal, and reflects a cohesive blend of architectural character and contemporary functionality. The eight detached studio residences are arranged in a bungalow-style layout that prioritizes privacy and individuality—an uncommon feature in downtown multifamily properties. Each unit includes a full kitchen, private bathroom, built-in Murphy bed, storage, and its own outdoor patio space, creating a distinctive residential or hospitality experience. The site’s configuration, with separate entrances and outdoor areas for each unit, supports a variety of operational approaches. Whether maintained as a short-term rental asset, repositioned toward furnished mid-term leasing, or operated as traditional multifamily housing, the property offers flexibility to adapt to evolving market conditions. Positioned within walking distance of Little Italy’s restaurants, cafés, and retail corridors, as well as the San Diego waterfront, the property benefits from consistent tenant and visitor demand. The surrounding area’s strong employment base, lifestyle appeal, and limited supply of comparable properties further reinforce its long-term desirability. The Union Street Bungalows represents a rare combination of historic character, regulatory advantages, and prime location—offering investors a differentiated asset with both immediate usability and enduring value in one of San Diego’s most competitive rental markets.