Downtown Poughkeepsie, NY homes for sale & real estate

Downtown Poughkeepsie, NY Homes for Sale

RARE OWNER OCCUPANT OPPORTUNITY in the City of Poughkeepsie, NY. This two building property features a spacious 2BR/1BA owner's unit currently rented at $1,875/mo with an attached 2-car garage, abundant storage and in unit washer/dryer. IDEAL for a buyer with a business or hobby — plus a second building with two long-term-tenanted 1BR/1BA units renting for $1,135 and $1,250/mo with off street parking and leases running through Aug 31, 2027. Perfect for an owner-occupant looking to live on-site while collecting rental income from day one. All municipal services and natural gas. Buildings are in good condition with newer features such as electrical, boiler/HVAC and roof. This unique tw

Downtown Poughkeepsie, NY Homes for Sale

Investment Opportunity – High Cash Flow Property in the Heart of Poughkeepsie Presenting 40 S. Hamilton Street, a rare opportunity to acquire a proven income-producing property in the City of Poughkeepsie. This well-established rooming house consists of nine private single-occupancy rooms, seven bathrooms, providing affordable and independent living accommodations that serve a critical role in the local housing market. This property is a grandfathered rooming house (meaning no other property can be zoned as a rooming house without a special permit). Coin operated laundry also included in the basement. The property has demonstrated strong and consistent performance, currently generati

Downtown Poughkeepsie, NY Homes for Sale

Welcome to a truly special piece of Poughkeepsie history. Built in 1877 and set within the Historic District, this striking Victorian residence offers an exceptional opportunity to restore and reimagine a grand historic home while preserving its remarkable architectural character. From the gracious curved staircase and soaring ceilings to original hardwood floors, intricate moldings, pocket and French doors, multiple fireplaces, and a distinctive glass-enclosed cupola, the craftsmanship and scale of this home are rarely found today. With approximately 4,831 square feet, three levels, 8 plus bedrooms (tax indicate 6), 6 baths (3 full 3 half), a spacious kitchen with cherry cabinetry, granite

Downtown Poughkeepsie, NY Homes for Sale

Impeccably Maintained Two-Family — First Time on the Market! Step inside this impeccably maintained two-family home and feel as though you’ve walked into a beautifully preserved time capsule! Offered for the first time on the market, this special property reflects years of pride of ownership, with beautiful original woodwork, charming details, and exceptional care throughout. The home features two separate 2-bedroom units, each offering comfortable living spaces and newer appliances. Recent improvements include kitchen sinks approximately 3 years old and a roof approximately 10 years old. The property offers gas utilities and separate electric, making it an excellent opportunit

Downtown Poughkeepsie, NY Homes for Sale

This home is located within a Historic residential corridor known for its prominent Victorian Architecture. George Corlies was responsible for mapping out and building many of the Victorian homes on South Hamilton Street. These special second Empire and Italian Villa designs give the block a Historic Charm. In the 1930's Many estates in the Hudson Valley f were retro fit internally to transition from a grand estate to a multi-Family. Today this building operates as a successful Triplex. It contains three distinct 2-bedroom apartments while preserving its defining Mansard roofline and distinctive second -empire framing. There is 1 gas meter and 1 electric meter. Seller will credit buyer $10,

Downtown Poughkeepsie, NY Homes for Sale

Welcome to 69 Montgomery Street, a beautifully maintained circa 1849 Colonial Victorian set in the heart of Poughkeepsie’s historic district, where original character and thoughtful modern updates come together. Step inside to soaring ceilings, gleaming red oak floors, and oversized, sun-filled rooms that immediately showcase the scale and craftsmanship of this historic home. The main level offers a spacious living room that flows naturally into the grand dining room—an inviting setting for everything from quiet dinners to holiday gatherings. The well-appointed kitchen features an induction cooktop and Sub-Zero refrigerator, combining modern function with the home’s timele