Prime Investment Opportunity in the Heart of Uptown Kingston. Strategically positioned in the heart of Kingston's historic Old Stockade Business District, 27 Main Street offers an exceptional opportunity for investors or owner-users to establish a commanding presence in Uptown Kingston. Located adjacent to the Ulster County government offices and a short walk to the County Courthouse, this rare offering includes three contiguous tax parcels totaling approximately 0.53 acres. The flagship property, 27 Main Street, is a distinguished two-story, 8663 SF commercial building constructed of limestone and brick in 1843. Rich with architectural character, it features soaring ceilings, grand columns, and original banking elements including a classic vault on the first floor and in the basement. A 1.9 million renovation in 2010 and a brand new roof installed in 2022 ensure modern functionality with historic charm. The first floor is leased to Rhinebeck Bank, a stable tenant since 2005. The Bank is in its second 10-year lease term, with 7 years remaining, and pays separately metered utilities. The second floor has been owner-occupied and will be delivered vacant. An ideal opportunity for office use or conversion in a low-vacancy office market. Alternatively, this space could be an amazing apartment or live/work space. Included in the sale are two additional parcels located at 264-266 Fair Street, totaling 0.23 acres and currently configured as a 32-space private parking lot. Of these, 7 are deeded exclusive use spaces, 20 unencumbered shared spaces, and 12 additional income producing spaces.. The parking lot offers immediate income potential or the ability to redevelop for a higher and better use, given its premium location in a fast-growing commercial corridor. Highlights: Three Contiguous Parcels | Total 0.53 Acres 7,415 SF Building | Built 1900 | Renovated 2010 2022 Net Operating Income: 113,896 New Roof (2022) Rhinebeck Bank: Long-Term Tenant (7 Years Remaining on Lease) 39 Space Parking Lot | Additional Development Potential Adjacent to Ulster County Office Building | Steps from Courthouse Separately Metered Utilities for Second Floor Significant Foot Traffic and Visibility in Uptown Kingston Whether you're looking for a flagship office location, an income-producing asset, or a development opportunity, 27 Main Street offers unmatched versatility, history, and prime positioning in one of the Hudson Valley's most vibrant commercial hubs.