Poughkeepsie City Homes with Oversized Parking features

Welcome to the vibrant Poughkeepsie City School District, nestled in the heart of Dutchess County, New York. This dynamic district is not just a place for academic growth; it’s a community that fosters creativity, inclusivity, and a lifelong love of learning. With a diverse range of educational programs, Poughkeepsie City School District is dedicated to nurturing students from all backgrounds, ensuring they are well-prepared for the future. The district boasts a variety of extracurricular activities, advanced placement courses, and dedicated staff who are committed to the success of each student.

Families looking to settle in this charming city will be delighted to discover homes featuring oversized parking options. These spacious properties are perfect for those who appreciate the convenience of ample parking, whether it’s for multiple vehicles, recreational toys, or simply for hosting friends and family. Imagine coming home to a beautifully designed residence with the luxury of oversized parking, allowing you to enjoy your space without the hassle of street parking.

Living in Poughkeepsie not only gives you access to a thriving school district but also places you at the center of a community rich in culture and history. From the scenic views along the Hudson River to the vibrant local arts scene, there’s something for everyone. Experience the perfect blend of education, comfort, and lifestyle in Poughkeepsie, where your dream home awaits!

Newest Poughkeepsie City 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

$500,000

4 Beds ⋅ 2 Baths ⋅ 1022089 MLS

Turnkey Investment Opportunity! This 2-family home is fully occupied and generating $52,800 annually. It will provide reliable cash flow from day one. Included in the sale is the lot next door (3 Park Place, 131300-6162-71-320192-0000). Leased solar panels were installed in 2022 to 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

$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

$454,930

5 Beds ⋅ 2 Baths ⋅ 1012357 MLS

Welcome to 361 Church Street, a prime investment opportunity in the heart of Poughkeepsie. This property offers the perfect blend of city living and long term value, located minutes to the Poughkeepsie Train station with direct service to New York city, close proximity to downtown restaurants, shops, schools, breweries, great night life and scenic Hudson River Views. this home offers all the perks of living in a revitalizing urban area. This home is great whether your looking for rental income or living your dream. This home presents a rare chance to invest in Poughkeepsie's expanding market. This home has potential for appreciation and strong returns. Oversized Front porch. Unit 1 offers 3 bedroom, galley kitchen, formal living room, full bath, high ceilings, beautiful wood floors, stained glass window, built-ins, very generous size rooms. The second unit offers 2 bedrooms includes a oversized primary bedroom with his and her closets, den/office, formal dining room, living room, full bath, galley kitchen, high ceilings, beautiful wood moldings includes private porch. Full walk up attic, Full dry basement. Seperate utilites and oil tanks, Updated roof and electric. Private fenced in backyard with lots of parking spaces. Come take a look at this fabulous home with tons of opportunities.. FULLY AVAILABLE BUYER FINANCING FELL THROUGH!!!

361 Church 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 and 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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