214 Main StreetPoughkeepsie, NY 12601Price: $1,699,000

214 Main Street Downtown Poughkeepsie Opportunity Zone | Courtyard | Separately Deeded Parking | Value-Add Upside 214 Main is a 7,500+ SF fully renovated four-story commercial building located in the heart of Historic Downtown Poughkeepsie's central business corridor and positioned within a federally designated Opportunity Zone. This asset offers rare flexibility: an investor can lease at market rates for stabilized yield, reposition for value-add upside, or occupy a flagship headquarters while generating income from additional floors. A Downtown Asset with Rare Amenities Unlike typical downtown inventory, 214 Main includes features that materially enhance both leasing velocity and long-term value: o Private Rear Courtyard A spacious and rare outdoor amenity ideal for tenant gatherings, hospitality activation, wellness programming, creative workspace use, or event-driven concepts. Outdoor space of this scale is a true scarcity asset. o Separately Deeded Adjacent Parking Lot (211 Union Street) Off-street parking for approximately 15 vehicles - a highly sought-after amenity in Downtown Poughkeepsie where dedicated parking is limited. This parcel is independently deeded, creating optionality for future monetization, development, or structured value enhancement. o Rare Outdoor Rooftop A private and rare outdoor amenity with multiple potential uses and a brand new waterproof roof. Building Configuration & Infrastructure Originally renovated in 2012, the property is professionally configured for single-tenant or multi-tenant occupancy. *10 private offices *2 conference rooms* Restrooms on every floor * Multiple storage areas *Separate utilities per level *Intercom system for controlled access *Large cellar-level recreation/training space suitable for classrooms, collaborative workspace, or tenant amenities The structure is handicap accessible and has undergone significant capital improvements, including: *Roof replacement *Updated front windows * Exterior lighting upgrades * Copper plumbing *Annual boiler and fire/alarm system inspections Heating is oil (above-ground tank). The layout supports straightforward floor-by-floor tenancy, enabling flexible lease structuring or phased occupancy. Prime Walkable Location 214 Main Street sits at the intersection of culture, commerce, and commuter flow: *Steps from the Bardavon 1869 Opera House *Near the Mid-Hudson Civic Center *Surrounded by restaurants, bars, retail, and nightlife *Close to government and municipal offices * Minutes to Metro-North (direct access to NYC) *Near Hudson River waterfront redevelopment This positioning supports strong demand from professional offices, medical administrative users, educational operators, nonprofits, creative service firms, and hybrid office concepts seeking urban vibrancy without Manhattan pricing. Opportunity Zone Advantage Located within a federally designated Opportunity Zone, qualified investors may benefit from capital gains tax deferral and potential long-term tax advantages (buyers to consult tax advisors). This designation enhances long-term hold strategies and repositioning opportunities. Investment Strategy & Upside The building will be delivered vacant, allowing for immediate repositioning and lease-up. With multiple floors, separately metered utilities, a private courtyard, and dedicated parking, the property provides: *Clear value-add lease-up potential * Owner-occupant with income strategy * Multi-tenant professional office conversion* Adaptive reuse potential *Long-term redevelopment optionality Downtown Poughkeepsie is undergoing sustained revitalization, and assets offering outdoor space, deeded parking, and walkable proximity to entertainment and transit are limited. 214 Main Street represents a rare combination of scale, flexibility, and embedded amenity value in a growing Hudson Valley market with direct commuter connectivity to New York City.