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

$999,999

6 Beds ⋅ 6 Baths ⋅ 998000 MLS

1920s Victorian Splendor with Exceptional Possibilities - Step into the timeless elegance of the 1920s at 104 Hooker Avenue, a distinctive Victorian property offering an impressive combination of historic character with gorgeous period woodwork, space, and future potential on almost one acre. Featuring six bedrooms, six bathrooms, and parking for 10+ vehicles, this extraordinary property provides the scale and flexibility rarely found in the area. Original architectural charm and classic Victorian details create an inviting backdrop for a variety of possibilities, while the generous property and expansive footprint offer room to imagine something truly special. Whether you're looking for an exceptional residence, an investment opportunity, or a property with potential for an alternative use, 104 Hooker Avenue deserves a closer look. Adding to the appeal is the property's potential for subdivision with its large, wooded frontage, subject to municipal review and approvals. There may also be an opportunity for a quiet-use professional or business application, subject to required approvals. With its grand proportions, abundant parking, substantial grounds, and coveted Victorian character, 104 Hooker Avenue presents an exciting opportunity to own a piece of Poughkeepsie's architectural history while exploring its future potential. Bring your vision and unlock the possibilities of this remarkable property. *Note - Some photos have been Virtual Enhanced

104 Hooker Avenue, Poughkeepsie

$449,888

3 Beds ⋅ 2 Baths ⋅ 1045349 MLS

Welcome to this spacious, move-in-ready single-story ranch nestled in desirable Colburn Estates! This well-maintained home offers numerous updates, comfortable living spaces, and excellent flexibility for today’s lifestyle. The main level features beautifully refinished hardwood floors throughout, a welcoming living room with a wood-burning fireplace, and California-style floor-to-ceiling windows with an exterior walk-out door providing an abundance of natural light and easy access to the yard. The sunken dining room addition is a wonderful gathering space, featuring newly installed 30"x 54" skylight with copper flashing and a new wall A/C unit installed in 2026. The kitchen offers quartz countertops and a gas cooktop, while both bathrooms were tastefully remodeled in 2018. Replacement windows on the main level are approximately 20 years old. Numerous improvements provide added peace of mind, including new vinyl siding installed in 2024, a recently power-washed exterior, architectural roof shingles installed in 2014, and new 5" gutters with stainless-steel mesh gutter guards. The home also benefits from additional insulation, including 3/4" foam board added with the siding installation and R-30 attic insulation. Four brand-new basement windows have recently been installed, and the main level and garage have been freshly painted. The lower level offers tremendous potential with a separate side entrance and a large unfinished area that can be customized to suit your needs. Create a home office, potential fourth bedroom, guest space, or explore a potential mother-daughter setup, subject to necessary approvals. There is also ample room to add another bathroom. Home is serviced with 200-amp electrical service adds further convenience. The oversized two-car garage addition features a side entrance and additional attic storage with a new metal attic door. The basement provides abundant storage, with the freezer included in the sale. A 7' x 10.6' storage shed provides even more outdoor storage. The Burnham furnace was installed in 2009 and converted from oil to natural gas in 2013; the oil tank was removed at that time. Municipal water and sewer and natural gas heat add to the convenience. Appliances include refrigerator (2008), wall oven (2009), washer and dryer (2018), and dishwasher (2020). Freezer stays, Ideally located with easy access to Route 9, shopping, supermarkets, and commuting options. The Poughkeepsie Metro-North station is approximately 5.9 miles away. With its generous spaces, extensive updates, flexible lower level, and convenient location, this home truly spells Home Sweet Home!

80 Colburn Drive, Poughkeepsie

$649,000

4 Beds ⋅ 3 Baths ⋅ 1044908 MLS

Welcome to 24 Deer Run Road, a beautifully designed new-construction bi-level tucked away on a quiet cul-de-sac in an established neighborhood within the Wappingers Central School District. Offering four bedrooms, three full bathrooms and a spacious, thoughtfully planned layout, this home blends modern style with everyday comfort. The bright and inviting main level features hardwood flooring throughout, with soaring cathedral ceilings connecting the kitchen, dining area and living room. This open-concept space is ideal for everyday living and entertaining, with direct access to a rear deck. The private primary suite provides a peaceful retreat with its own full bathroom and walk-in closet. Two additional bedrooms and a second full bathroom complete this level. The finished lower level features durable vinyl flooring, a generously sized family room, fourth bedroom, third full bathroom, separate laundry room and direct access to the oversized two-car garage. This versatile space is perfect for guests, a home office, recreation room or additional living area. Outside, the property offers a comfortable backyard, a large side yard and a wooded backdrop that creates a wonderful sense of privacy. There is plenty of room to relax, entertain, garden or simply enjoy the peaceful natural surroundings. Enjoy everything Dutchess County and the Hudson Valley have to offer, including nearby parks, hiking trails, Hudson River recreation, local farms, markets, restaurants and cultural attractions. Conveniently located near Route 9, shopping, dining, medical facilities and Metro-North train service, with easy access to Poughkeepsie, Wappingers Falls, Beacon and other popular Hudson Valley destinations. Estimated completion is approximately three months, and there is still time for the buyer to select certain finishes and add personal touches to their new home.

24 Deer Run Road, Poughkeepsie

$599,900

4 Beds ⋅ 3 Baths ⋅ 1043586 MLS

Pre-qualified buyers only please. This unique home is being offered for the first time in over ten years and it's a lot of house for the money. All large sized rooms on an oversized lot located at the end of a lovely street just minutes from everything. The entrance foyer has built in planters and an entire wall of custom stonework that opens up to an oversized living room with the same stonework and woodstove insert- even the wood is included for next winter's burning. There is a nice sized kitchen with a center island, and the laundry room is conveniently located right in the same room for your ease!! The dining room is there as well and has a bow window and even a built-in ironing board from the old days with a door out to the massive wrap around deck that overlooks the inground Gunite pool. There are two bonus rooms with parquet floors off of the dining area and the living room with pocket doors that are currently being used as an office and an exercise room. The home allows for anyone to choose how to use the different rooms for their individual needs and taste! The main floor has a large primary bedroom with a full bath, two additional bedrooms, and a bathroom in the hallway with double sinks. On the lower level, there is a massive fourth bedroom, a full bathroom that opens to the outside to facilitate easy access to the pool, and storage galore. There is also a large family room with a built-in bar, a non-working second wood burning fireplace insert, and a large pool table room that is not heated. There is also a large room for mechanicals and storage galore and a utility room as well. The space inside this custom home and its unique features will surprise you and the pictures don't do it justice. Outside there is a pool house, large decking overlooking the pool, and a few patios to choose from. One of the best features of this home is the detached garage with multiple doors and a full walk up to a second story. A car enthusiast or hobby person could spend years deciding on its best use or change their plans as the need arises!! The solar power is fully paid for and off sets the utility bills- we are currently looking into whether the current credit will be transferable to the new owners.

58 Ireland Drive, Poughkeepsie

$599,000

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, such as plaster ceilings and walls throughout. 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! **Some photos have been virtually staged**

129 Academy Street, Poughkeepsie

$599,000

3 Beds ⋅ 4 Baths ⋅ 1030561 MLS

Move-in Ready. This spacious Contemporary home has been updated. Features an Open Floor plan for today's modern living with custom Chiefs Kitchen with 36 inch range and Stainless Steel Range hood, Living and dining area has two double doors that walk-out to large deck that is ideal for entertaining and view of the private backyard. Primary bedroom has two walk-in closets, and private bath. Lower level features Recreation room, walk-out to backyard and covered deck area and full bath. There is a Tandem two car and single garage with a total of 3 car car capacity. Plenty of room in the backyard with two sheds for extra storage. Desirable neighborhood with quick access to nearby schools, Taconic Parkway, and Route 55 with ample shopping, restaurants, and nearby parks and bike trail.

83 Smith Road, Poughkeepsie

$500,000

4 Beds ⋅ 2 Baths ⋅ 1022089 MLS

Great Investment Opportunity! This 2-family home has one leased unit and one vacant. Live in one unit and use the rent to help with expenses or rent out both units for maximum income. It has been generating $52,800 annually. Included in the sale is the lot next door (3 Park Place, 131300-6162-71-320192-0000). Solar panels will be paid off by seller at closing. Solar panels were installed in 2022 and keep electricity costs to the bare minimum of $60/month. Separate natural gas meters allow tenants to pay, which saves on the owner's monthly cost. The roof was replaced in 2022 when the panels were installed. Each unit offers 2 bedrooms, 1 bath, large kitchen, dining room, living room, and unit 2 has a den/office that leads to the balcony. With a shared washer and dryer, basement storage, plenty of parking, and a convenient location close to shopping, dining, schools, and major commuter routes, this property is designed for both tenant appeal and long-term value.

1 Park Place, Poughkeepsie

$575,000

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

$445,000

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

$575,000

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

$385,000

3 Beds ⋅ 2 Baths ⋅ 1000609 MLS

This charming three-bedroom, two-bathroom home offers spacious living with timeless character and endless potential. Step into the inviting enclosed sunroom entrance, the perfect place to relax and enjoy natural light year-round. Inside, you’ll find the home is freshly painted with refinished hardwood floors and the kitchen featuring beautiful NEW wood cabinetry, NEW gas stove, recess lighting and a doorway onto the rear deck overlooking the property. The living room is open to the formal dining room, and a spacious and impressive entryway that welcomes you home. The home boasts generously sized rooms, hardwood floors throughout, natural gas heat, city water, and city sewer for added convenience. A side entrance provides easy access, while the unfinished walk-up attic offers excellent storage space and includes a window, creating possibilities for future use and storage space. Unfinished basement with utilities and storage space. Outside, enjoy a beautiful flat garden property with ample parking for 4 plus cars, making this home ideal for entertaining, gatherings, or everyday comfort. A wonderful opportunity to own a spacious home with charm, functionality, and room to grow. located close to shopping, restaurants and schools, with a short commute to Metro North trains along with the walkway over the hudson river with its faboulous hiking, biking & walking trails.

100 Innis Avenue, 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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