Poughkeepsie City Homes with Driveway Parking features

Welcome to Poughkeepsie City, a vibrant gem nestled in the heart of Dutchess County, New York. Known for its rich history and picturesque landscapes, Poughkeepsie offers a unique blend of urban amenities and suburban charm. One of the standout features of this area is its exceptional school district, the Poughkeepsie City School District, which is dedicated to fostering a nurturing and inclusive learning environment for all students.

The Poughkeepsie City School District prides itself on its commitment to academic excellence and community engagement. With a diverse array of educational programs, including advanced placement courses and vocational training, students are well-prepared for college and careers. The district emphasizes the importance of holistic development, offering various extracurricular activities that encourage creativity, teamwork, and leadership skills. Parents will appreciate the strong emphasis on communication and collaboration between schools and families, ensuring that every child has the support they need to thrive.

For those considering a move to this charming city, many homes feature convenient driveway parking, making it easy for residents to come and go as they please. Imagine returning home after a long day and parking right in your own driveway, a luxury that adds to the comfort and convenience of everyday living.

With its excellent educational opportunities and welcoming neighborhoods, Poughkeepsie City is not just a place to live; it’s a community where families can grow, learn, and thrive. Explore the possibilities of making this wonderful city your new home!

Newest Poughkeepsie City Homes with Driveway Parking features

$450,000

3 Beds ⋅ 3 Baths ⋅ 1007852 MLS

Timeless Mid-Century Modern brick home offering enduring quality and incredible potential. Featuring hardwood floors, classic architectural details, and a spacious walk-up attic with a variety of potential uses, this solid home is ready for its next chapter. While it would benefit from updating, its exceptional location and quality construction present an outstanding investment opportunity in the Hudson Valley at an attractive value. A wonderful opportunity to personalize and restore a well-built home. Conveniently located near shopping, restaurants, parks, and the Poughkeepsie Tennis Club, and approximately a five-minute drive to the Poughkeepsie Metro-North and Amtrak station, this home combines timeless charm with everyday convenience in an established neighborhood.

13 Osborne Road, Poughkeepsie

$324,900

3 Beds ⋅ 1 Baths ⋅ 1029760 MLS

Welcome to this well-maintained Colonial offering over 1,200 square feet of comfortable living space with 3 bedrooms and 1 full bathroom. Blending classic charm with tasteful updates, this home features a spacious and inviting living room highlighted by a beautiful brick fireplace and abundant natural light. The updated eat-in kitchen features beautiful vaulted ceilings, white cabinetry, stainless steel appliances, ample counter space, and room for dining, creating the perfect space for everyday living and entertaining. A full bathroom is conveniently located on the main level, while the second floor offers three bedrooms, including a generously sized primary bedroom with a walk-in closet. Recent updates and improvements throughout the home provide a move-in ready feel while still maintaining character and warmth. Outside, enjoy a large level backyard with patio space, mature trees, and plenty of room for outdoor gatherings, gardening, or recreation. Conveniently located near shopping, restaurants, schools, parks, and major commuter routes, this charming home offers both comfort and convenience.

194 Smith Street, Poughkeepsie

$449,500

4 Beds ⋅ 3 Baths ⋅ 1028671 MLS

Steeped in history and rich in architectural significance, The James D. Keith House is one of Poughkeepsie's most recognizable residences. Gracefully positioned within the coveted Academy Street Historic District, this extraordinary c.1900 Colonial Revival masterpiece—designed by acclaimed local architect Percival M. Lloyd, this home beautifully blends timeless Colonial elegance with Victorian-inspired details. Offering almost 3,400 finished SQFT, 4 bedrooms, 2 full and 1 half baths, three fireplaces, and an additional unfinished third floor and expansive basement, this is a rare opportunity to own one of the Hudson Valley's architectural treasures. From the moment you step through the crystal-lined vestibule, you're welcomed by breathtaking period craftsmanship. A dramatic central foyer showcases a sweeping grand staircase illuminated by an impressive cathedral-height stained-glass window, while original woodwork, intricate moldings, soaring ceilings, hardwood floors, built-in cabinetry, oversized pocket doors, and elegant fireplaces highlight the home's remarkable character throughout. The main level was designed for both grand entertaining and comfortable everyday living. Multiple formal gathering spaces include an elegant living room with a wood-burning stove insert, a gracious formal parlor tucked into the home's iconic rounded tower, an expansive formal dining room, and an inviting wraparound covered porch that seamlessly extends the living space outdoors. The spacious eat-in kitchen, complete with adjoining butler's pantry and separate laundry room, overlooks the peaceful backyard beneath the canopy of a magnificent copper beech tree, providing the perfect opportunity to create a dream chef's kitchen while honoring the home's historic integrity. The second floor offers four generously sized bedrooms, two full bathrooms, and a flexible den or sitting room ideal for a home office, library, or nursery. The primary suite is warmed by a recently relined Rumford fireplace, while the spectacular tower bedroom captures sweeping western views and unforgettable Hudson River sunsets beneath its distinctive domed ceiling and beautifully arched architectural detailing. Above it all, the unfinished third floor presents approximately 1,500 square feet of untapped potential. Featuring soaring cathedral ceilings, abundant natural light, and charming architectural details, this incredible space is ready to become a luxurious primary retreat, artist's loft, guest quarters, home office, or creative studio. The expansive full basement offers an additional level of opportunity with room for workshops, storage, recreation, or future finished space. Outside, the stately wraparound porch, Juliet balconies, mature landscaping, and classic Colonial Revival facade create unforgettable curb appeal while honoring the home's historic pedigree. Situated on a quarter-acre lot in one of Poughkeepsie's most distinguished neighborhoods, the property is just moments from Vassar Brothers Medical Center, the vibrant downtown waterfront, restaurants, shops, Metro-North, and all that the Hudson Valley has to offer from hiking at Mohonk Preserve to weekend escapes in the Catskills. Whether you're an architectural enthusiast, preservationist, or visionary homeowner, 151 Academy Street offers a once-in-a-generation opportunity to restore, personalize, and preserve one of Poughkeepsie's most celebrated historic homes. Offered AS-IS, this remarkable residence is ready for its next chapter, to be restored and for someone who appreciates the craftsmanship, scale, and timeless beauty that simply cannot be replicated. Municipal water, sewer and natural gas! Excellent location, minutes to Route 9, Downtown Poughkeepsie, Walkway over the Hudson, Culinary Institute of America, Marist University, schools, all things shopping and more! Come be a part of History and see all that the Hudson Valley has to offer! *SOME INTERIOR PHOTOS HAVE BEEN VIRTUALLY STAGED WITH FURNITURE*

151 Academy Street, Poughkeepsie

$599,900

3 Beds ⋅ 3 Baths ⋅ 1028071 MLS

Welcome home to this meticulously maintained Colonial, completely renovated in 2024 and offering the perfect blend of modern style, comfort, and convenience. Step inside to discover a light filled, open floor plan designed for today's lifestyle. The stunning chef's kitchen features KraftMaid cabinetry, beautiful Quartz countertops, abundant workspace, and seamlessly flows into the dining area and spacious living space, perfect for everyday living and entertaining. A sliding glass door opens to a brand-new Trex deck with a retractable awning overlooking the level, fully fenced backyard. Working from home is effortless with the private first-floor office, complete with elegant French doors, providing a quiet and comfortable workspace. Upstairs, the primary suite offers an en-suite bath and generous closet space. Two additional bedrooms with another full bath and an oversized bonus room providing incredible flexibility as a playroom media room, home gym, or even a potential fourth bedroom. Additional features included a second floor laundry attaehed two car garage, generator, and countless updates throughout, making this truly move-in. Ideally located on the sought-after Southside of Poughkeepsie, this exceptional home is just minutes from shopping, restaurants, schools, major commuter routes, and approximately 3.5 miles from the metro-North train station. Furniture is negotiable.

24 Whittier Boulevard, Poughkeepsie

$529,000

5 Beds ⋅ 3 Baths ⋅ 1026212 MLS

Investment or owner-occupant opportunity at 17 North Clover Street, a spacious three-unit property offering flexibility, recent exterior improvements, and a convenient location. The building features two vacant units, each offering two bedrooms and one full bathroom, allowing a new owner to select tenants, establish current rental terms, or occupy one unit while generating income from the others. The third unit is an occupied one-bedroom, one-bathroom apartment, providing immediate rental income. Recent improvements include new roofs on both the main house and detached three-car garage, a freshly painted exterior, and an upgraded common foyer that creates an inviting entrance for residents and guests. Additional highlights include off-street parking and a three-car garage offering space for vehicles, storage, or other income generating possibilities. Ideally positioned within close proximity of the Poughkeepsie Metro-North and Amtrak station, the property provides convenient rail access to New York City, Albany, and surrounding Hudson Valley destinations. It is also close to Route 9, Routes 44/55, the Mid-Hudson Bridge, downtown restaurants and shops, the Poughkeepsie waterfront, parks, and the Walkway Over the Hudson. With two vacant apartments, an occupied income-producing unit, major exterior upgrades, and a highly accessible location, this is a great opportunity to build or expand a real estate portfolio.

17 N Clover Street, Poughkeepsie

$799,990

6 Beds ⋅ 4 Baths ⋅ 1023883 MLS

Welcome to Academy House. Built in 1881, this distinguished Victorian residence is set along one of Poughkeepsie’s most admired tree-lined streets within the city’s Historic District. A gracious front porch introduces a home where original craftsmanship has been thoughtfully preserved while modern infrastructure provides the comfort and reliability expected today. The main level unfolds through a welcoming foyer into a collection of light-filled living and entertaining spaces, where generous proportions and beautifully preserved architectural details create a natural sense of flow. The dramatic horseshoe window in the grand living room is elegantly echoed in a remarkable set of pocket doors leading to the family room, a distinctive design feature that showcases the exceptional craftsmanship found throughout the home. A gracefully curved ceiling above the gathering area and the home’s signature curved glass windows further highlight its architectural character. Newly updated kitchen blends historic charm with modern function, featuring quartz countertops, stainless steel appliances, and abundant workspace designed for everyday living and entertaining. Extensive infrastructure improvements provide confidence behind the walls while allowing the home’s original character to remain the focal point. Recent updates include an upgraded electrical system, replacement PVC plumbing throughout, updated main sewer piping, a newer roof, storm windows throughout the home, and a new water heater. Together, these improvements deliver the convenience and efficiency of modern living without compromising the home’s historic integrity. The second level is accessible by both the main staircase and a secondary staircase off the kitchen, offering a layout that reflects the home’s original design while enhancing everyday functionality. Six bedrooms are thoughtfully arranged across the upper floors, including two spacious primary suites with beautifully renovated custom bathrooms. The remaining bedrooms are filled with natural light and enriched by original architectural details that continue the home’s timeless appeal. The finished and insulated third level offers exceptional flexibility, featuring an additional family room, two bedrooms, and a full updated bathroom. Whether used as guest accommodations, a home office, creative studio, or private retreat, this level provides versatile living space while maintaining the home’s historic character. Outside, the fully fenced backyard extends the living experience with space for outdoor dining, gardening, or quiet afternoons in a private setting. A detached two-car garage and newly paved driveway provide everyday convenience while complementing the property’s classic streetscape. Meticulously maintained throughout, Academy House offers the rare opportunity to enjoy the beauty and craftsmanship of a historic Victorian without the extensive restoration projects often associated with homes of this era. Positioned just minutes from Metro-North, Vassar College, Marist University, local hospitals, restaurants, cafés, and the growing cultural and dining destinations of downtown Poughkeepsie, the location offers exceptional convenience while remaining rooted in one of the city’s most architecturally significant neighborhoods. Academy House captures the elegance of 1881 with the infrastructure and functionality expected today, creating a residence where historic craftsmanship and modern living exist in effortless harmony.

112 Academy Street, 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

$450,000

6 Beds ⋅ 3 Baths ⋅ 1023576 MLS

Welcome to 17 Coughlin Street, a value-packed three-unit investment property offering immediate rental income and additional upside in the heart of Poughkeepsie. Two of the three apartments have been fully renovated and are currently rented, featuring updated kitchens and bathrooms, new appliances, modern flooring, fresh finishes, and bright, comfortable living spaces. The ground-level unit is under construction and has been thoughtfully set up for the next owner to complete, providing an excellent opportunity to customize the space and further increase the property’s income potential. Major improvements include a new roof, renovated siding, updated electrical and plumbing systems, separate water heaters, and a fire-alarm system. Outside, the property offers valuable off-street parking, a spacious rear area, and a rare three-car garage with excellent potential for parking, storage, or additional rental income. Conveniently located near downtown Poughkeepsie, shopping, restaurants, public transportation, the Metro-North train station, Route 9, Routes 44/55, the Mid-Hudson Bridge, and the Walkway Over the Hudson, this property combines updated living spaces, strong income potential, and a commuter-friendly location. A great opportunity for investors or owner-occupants looking to complete the final unit while collecting income from the two renovated apartments.

17 Conklin Street, Poughkeepsie

$275,000

4 Beds ⋅ 2 Baths ⋅ 1022653 MLS

Opportunity awaits in this spacious 3-bedroom, 2-bath home that offers the flexibility to live like a 4-bedroom. Ideally located just minutes from Poughkeepsie’s waterfront, Metro-North, restaurants, and local amenities, this property is perfect for buyers looking to build equity. The home needs updating and is being sold as-is, making it a great opportunity for an owner-occupant or investor ready to bring their vision to life.

39 Spruce Street, Poughkeepsie

$299,900

3 Beds ⋅ 2 Baths ⋅ 1022816 MLS

2 Family within walking distance to Metro North, the Main Street Restaurant District and the waterfront. Solid rental history with very low turnover. This home features separate utilities and a driveway for off street parking. Perfect for the investor or a live in one unit and rent out the other unit type situation.

10 Charles Street, Poughkeepsie

$595,000

4 Beds ⋅ 4 Baths ⋅ 1020852 MLS

Rare offering featuring 3,458 square feet of living space. Steeped in history and architectural charm, this enchanting 1921 residence is a true standout in the heart of Poughkeepsie. Thoughtfully designed with romantic architectural influences, rich craftsmanship, and timeless character, this eclectic home evokes the warmth and artistry of another era, and over a century later, it continues to do exactly that. Wrapped in classic stucco and once crowned with its iconic red tile roof, this whimsical home has been lovingly maintained and thoughtfully updated over the years, including a new roof and beautifully renovated bathrooms, while preserving the timeless character that makes homes of this era so extraordinary. Step through the true tiled vestibule and into a world of warmth, texture, and craftsmanship. The formal living room welcomes you with a stunning tiled fireplace framed by rich natural woodwork and gracious proportions, while the adjoining formal dining room showcases original windows that beautifully frame the artistry and soul of this home. Mirroring the formal living space is a cozy media room, offering additional flexibility for relaxing or entertaining, alongside a full first floor bathroom complete with tub. Toward the rear of the home, discover an expansive kitchen, charming library with exposed brick fireplace, and an authentic butler’s pantry, spaces that feel both practical and storybook in nature. An additional full bathroom on the main level creates wonderful flexibility for guests, extended stays, or multi generational living. Upstairs, retreat to a true ensuite primary bedroom, accompanied by two additional bedrooms, a dedicated office, and a beautifully tiled full bathroom. Throughout the home, exquisite original woodwork, graceful arched doorways, and architectural details rarely seen in modern construction add to the undeniable charm and feel good energy this home radiates. Homes like this are more than houses, they are experiences. Rich with character, warmth, and whimsy, this one simply must be experienced to fully appreciate the beauty, history, and unmistakable feeling of home it offers.

96 Hooker Avenue, Poughkeepsie

$482,000

4 Beds ⋅ 3 Baths ⋅ 1020360 MLS

Excellent investment opportunity in the heart of Poughkeepsie! This well-maintained triplex is ideally situated on a quiet residential street just minutes from the Walkway Over the Hudson, Route 9, the Poughkeepsie Train Station, restaurants, shopping, parks, and all the conveniences the Hudson Valley has to offer. The property features three spacious units. Unit 1 offers one bedroom and one full bath and is currently rented. Unit 2 is currently owner-occupied and configured as a one-bedroom, one-bath with an additional open room currently being used as an office. Easy to show and offering flexibility for the next owner. Unit 3 includes one bedroom and one full bath and is also tenant-occupied. The property generates solid rental income with excellent potential for additional cash flow. Whether you're looking to expand your investment portfolio or occupy one unit while collecting rental income from the others, this property presents an outstanding opportunity. Its desirable location, strong rental potential, and proximity to major commuter routes, shopping, dining, and the Walkway Over the Hudson make 95 Albany Street a smart investment in one of Poughkeepsie's most convenient neighborhoods. Don't miss your chance to own this profitable multi-family property with excellent upside potential!

95 Albany Street, Poughkeepsie

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