Poughkeepsie Homes with Oversized Parking features

Poughkeepsie Homes with Oversized Parking features

Welcome to Poughkeepsie, a charming city nestled in the heart of Dutchess County, New York. Known for its rich history, vibrant arts scene, and stunning natural beauty, Poughkeepsie offers a unique blend of urban amenities and small-town charm. Situated along the picturesque banks of the Hudson River, this city is not only a hub for culture and education but also a gateway to the breathtaking landscapes of the Hudson Valley.

Poughkeepsie boasts a diverse range of homes, and for those who prioritize convenience, our listings featuring oversized parking are a true gem. Imagine coming home to a spacious property that accommodates multiple vehicles, perfect for families, car enthusiasts, or anyone who enjoys hosting friends and family. These homes are designed with practicality in mind, providing ample space for your cars, RVs, or even a boat, making it easy to explore the nearby scenic spots and outdoor adventures that the Hudson Valley has to offer.

In addition to the oversized parking features, homes in Poughkeepsie are often set in welcoming neighborhoods, close to schools, parks, and local shops. The city’s vibrant community spirit is palpable, with events and festivals that celebrate the local culture. Whether you're strolling along the Walkway Over the Hudson or enjoying a meal at one of the many delightful eateries, Poughkeepsie is a place where you can truly feel at home.

Explore our listings today and discover the perfect property that combines the beauty of Poughkeepsie with the practicality of oversized parking! Your dream home awaits in this enchanting city.

Newest Poughkeepsie Homes with Oversized Parking features

$650,000
6 Beds 2 Baths 1030768 MLS
Step into the rich history of this circa 1865 home, located in the City of Poughkeepsie's Historic District. Offering approximately 3,876 square feet across three finished levels, this residence showcases a distinctive Mansard roof, pocket doors, original millwork, bay windows, extensive built-ins, decorative fretwork, and other preserved architectural details that reflect its history and craftsmanship. A grand staircase with ornate woodwork and a built-in hall settle welcomes you upon entry, while hardwood floors, high ceilings, and ornate cast-iron radiators continue throughout much of the home. Spacious rooms provide flexibility for everyday living, entertaining, home office space, or creative pursuits. The kitchen complements the home's period appeal with custom wood cabinetry, built-in hutches, exposed brick, granite countertops, a movable center island, and a bright bay-window dining area. A freestanding wood stove set on a decorative mosaic tile hearth adds warmth and architectural interest. Additional features include a covered front porch, three finished levels, a full unfinished basement, municipal water and sewer, oil heat, and mature landscaping. Conveniently located near Route 9, Metro-North, the Mid-Hudson Bridge, the Poughkeepsie waterfront, restaurants, shopping, parks, Vassar Brothers Medical Center, Marist University, Vassar College, and other Hudson Valley amenities. A rare opportunity to own a substantial historic home in the City of Poughkeepsie's Historic District, offering preserved architectural details, generous living space, and a convenient Hudson Valley location. Don't miss out!

129 Academy Street, Poughkeepsie

$595,000
4 Beds 2 Baths 1026736 MLS
Beautifully Modernized and Expanded 2,426sqft, 4-Bedroom California Ranch, nestled in Barnegat Estates has much to offer. In 2006 the Homeowners built an addition with a 2 car, 768sqft Workshop/Garage and a 576sqft Living Room over it. Main Level offers 3 Bedrooms, a Gorgegous Full Bathroom with Corian Counters, Stylish Finishes, Subway Tile and Skylight. Spacious Living with room to grow. Large Formal Dining, Eat-In-Kitchen and Living Room. Kitchen offers Beautifully Tiled Floor, Corian Counters, Maple Cabinets, Stainless Steel Appliances, Cook's Window, Breakfast Island, SkyLight, Desk/Sitting Nook and French Doors to the Living Room. The Living Room is next to nature with 3 walls of windows, a great space for large gatherings around the Gas Fireplace. Sliding Glass Doors to Deck with Awning for a cool breeze in the shade, with quick access to yard and Gardens. Mother/Daughter with first Level Entry, offers 768sqft, 2 Rooms, Gas Fireplace, Walk-In-Closet, Renovated Full Bathroom w/Shower, Laundry, Kitchenette Nook and Addt'l Storage. Making it a perfect home for those seeking more space, larger rooms, additional Garages, a heated Workshop, or a Mother/Daughter layout. Situated on a Beautifully manicured .25 of an acre, offering ready to grow Garden Beds, Shade Trees and absolutely gorgeous Mature landscaping. 275k Addition 2006 New Siding 2006 New Roof 2020 New Boiler 2024 New Bathrooms 2025 New Water Heater 2026 Well Maintained Beautifully Renovated Lots of Natural Light Skylights Beautifully Tiled Hardwood Floors Heated Workshop Bonus Garage Space Central Location Close to IBM, Major Shopping, Parks, Schools, Hospitals, Colleges, Restaurants, Spratt Park/McCann Golf Course and only 6 miles to Metro North!

23 Hankin Loop, Poughkeepsie

$459,900
3 Beds 2 Baths 1020961 MLS
South side extremely well cared for home is looking for its next long term owner. Looking for a home that will offer you everything you're looking for? Stop the search is over. A solidly built brick cape style home situated above the quiet street it sits on. Plenty of off street parking and a backyard made for gatherings. A whole house basement with two root cellars and the ceiling hight to do whatever you would like. Game room, home gym, plenty of storage or whatever else you may think of. Access the garage and your car without going outside, no more hot sun, cold snow or wet rain to hinder you from comfortably entering or exiting your car. The house offers a warm welcoming entry from the front door where hardwood floors through out the home lead to a very generous sized living room with fireplace. A formal dinning room to enjoy any celebration or holiday you like. A large eat in kitchen with more counter top space then you could use. A counter top stove and double wall oven to prepare culinary delights and snacks alike. You can also enjoy a cold drink, warm cup of morning coffee or just unwind in the screened in porch right of the eating area of this incredible kitchen. Down the hallway leads to two generous sized bedrooms with closets for plenty of clothes. Your first full bath rounds off the first floor of this home. Then up the stairs to the second floor where you will find space for even more storage if you need it, your second full bathroom and a third spacious bedroom with closets. A large walk in cedar closet is also there for anything you'd like to store in it. At the end of the home is a large space currently used for even more storage or can be finished to become an incredible work from home office that would be extremely private or a sitting area for relaxing and unwinding with tv away from it all steps away from your slumber. Close to everything the city and town has to offer, minutes to Raymond ave farmers market and restaurants. A few more minutes to the main street corridor, waterfront, train station and the Walkway over the Hudson state park. Home was so well cared for that any updating you may like to do can be done when you would like as you like in time if you decided. The pride of ownership is blinding in this home. Easy to show but confirmation is required.

10 Degarmo Place, Poughkeepsie

$649,000
1021090 MLS
Position yourself in the heart of Downtown Poughkeepsie with this exceptional mixed use investment opportunity at 381 Main Street. This well-maintained commercial property offers the rare combination of immediate cash flow, long term upside, and one of the most valuable amenities in the city: dedicated off street parking with approximately 10 exclusive spaces. The first floor is occupied by a successful, high-end salon whose owner is offering the property for sale and is interested in remaining as a long-term tenant, providing investors with immediate occupancy and rental income from an established business. The second floor is currently leased on a month-to-month basis to a nail salon, offering flexibility to maintain the existing tenant, negotiate new lease terms, or reposition the space to maximize future income. Investment potential extends well beyond the existing rental stream. With approximately 10 dedicated parking spaces, this property offers an uncommon advantage in Downtown Poughkeepsie, where neighboring commercial buildings often lack private parking. The lot itself presents an additional revenue opportunity through leased parking spaces for nearby businesses, employees, or residents, creating another potential income source. Located within an area benefiting from ongoing public and private investment, Downtown Poughkeepsie continues to experience significant revitalization, making this an ideal time to secure a commercial asset with both current income and future appreciation potential. Investors seeking stable cash flow may appreciate the opportunity to retain the existing businesses while strategically increasing rental income over time to improve overall returns. Whether you are completing a 1031 Exchange, expanding your commercial portfolio, or seeking a mixed-use asset with multiple income streams, 381 Main Street offers a compelling combination of location, flexibility, parking, and long-term investment potential. Opportunities to acquire a property of this caliber with established tenants, dedicated parking, and multiple avenues for increased revenue are increasingly rare in the City of Poughkeepsie.

381 Main Street, Poughkeepsie

$700,000
9 Beds 3 Baths 973933 MLS
Academy Street Development Opportunity Multi-Family + 2 Vacant Parcels | Value-Add + Redevelopment Potential Located in the heart of Downtown Poughkeepsie’s rapidly evolving corridor, this Academy Street offering presents a rare opportunity to acquire a multi-family property along with two adjoining vacant parcels, ideal for both immediate income and future development. The existing multi-family structure features large residential units with strong rental potential, making it an attractive value-add investment. With renovations, this property can generate solid cash flow while providing a strategic hold for future expansion. What truly sets this offering apart are the two additional vacant parcels, creating a unique assemblage that opens the door to a variety of redevelopment possibilities. Whether expanding the current building, constructing new residential units, or creating a mixed-use concept, the flexibility here is a major advantage. Situated within the MU-5 (Mixed-Use 5) zoning district, the property allows for: Multi-family residential development Retail, office, and service-based uses Potential for up to 5 stories (with bonus height opportunities up to 7 stories) Developers and investors will appreciate the ability to maximize density in a high-demand rental market, all while being positioned near major amenities, transportation, and ongoing city revitalization efforts. Additional highlights include: Prime downtown location near business district, courthouse, and train station Strong rental demand in the area Flexible zoning supporting multiple development strategies Opportunity to create scale with adjacent parcels This is an ideal opportunity for an investor or developer looking to combine immediate income with long-term upside, in one of Poughkeepsie’s most active growth areas.

50 Academy Street, Poughkeepsie

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