Poughkeepsie City Homes with Detached Parking features

Welcome to Poughkeepsie City, nestled in the scenic Dutchess County of New York, where vibrant community life meets educational excellence. The Poughkeepsie City School District is renowned for its commitment to fostering a nurturing environment for students, offering a diverse range of programs that cater to various learning styles and interests. With a focus on academic achievement, the district boasts a strong curriculum complemented by dedicated educators who inspire and empower students to reach their full potential.

Families will appreciate the district's emphasis on extracurricular activities, which include sports, arts, and various clubs, ensuring that children have ample opportunities to explore their passions and develop essential life skills. The district is also known for its strong community involvement, encouraging parents and guardians to engage actively in their children’s educational journey.

As you explore the charming neighborhoods of Poughkeepsie, you'll discover homes that not only offer comfort and style but also come with the added convenience of detached parking. Imagine coming home to a beautifully designed residence, complete with a spacious garage or parking area that provides both security and easy access to your vehicle. These homes are perfect for families, professionals, and anyone who values the practicality and peace of mind that comes with having dedicated parking.

Living in Poughkeepsie means you’re not just investing in a home; you’re becoming part of a thriving community that prioritizes education and family-friendly living. Discover your dream home in this picturesque city, where quality education and comfortable living go hand in hand!

Newest Poughkeepsie City Homes with Detached Parking features

$465,000

4 Beds ⋅ 3 Baths ⋅ 1026339 MLS

Welcome to 149 Washington street, where beauty, functionality and affordability meet. Featuring 4 bedrooms, 2.5 bathrooms, a fully renovated kitchen, formal dining room, semi finished basement and beautiful livingroom fitted with a timeless stone fireplace. An additional flexible living space is offered as a fully finished attic boasts a huge amount of addition square footage. This home offers detailed finishes you don't often see today including stained glass windows, and craftsman style wood features. As a bonus, a split heating system allows each floor its own comfortable living temperature. Located directly across the street from the community pool, a half mile from major educational institutions, and less than a block from the renowned Walkway Over the Hudson. Imagine yourself sipping sweet tea as you relax on your porch swing after a day at the community pool. The perfect opportunity to own as a home or turnkey rental property. Truly a must see.

149 Washington 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

$299,900

917401 MLS

Two unit home featuring large two bedroom apartments with separate utilities. Gas furnaces and hot water heaters. Separate entrances as well as front and back porches. Full walk up attic and full basement for storage, laundry or whatever you would need the extra space for. The second floor is vacant for easy log and go showings, the first floor would require 24 hour notice if you would like to see both at the same viewing. Long time tenant on the first floor would be happy to stay if desired. This home is close to public transportation, schools & the main street corridor. Walk to Raymond Avenue farm market as well as restaurants in the area. Some updating needed but can provide positive cash flow quickly.

9 GRAY Street, Poughkeepsie

$379,000

3 Beds ⋅ 2 Baths ⋅ 998179 MLS

Step into timeless charm with this 3 bedroom, 1.5 bathroom brick and stone Cape Cod, where classic architecture meets warm, inviting living spaces. From the moment you arrive, the home’s solid masonry exterior and steeply pitched roofline create unforgettable curb appeal that speaks to craftsmanship and character. Inside, rich hardwood flooring flows throughout, adding warmth and elegance to every room. Original features—including vintage hardware, and thoughtfully preserved architectural touches—celebrate the home’s heritage while offering a distinctive sense of style you simply can’t replicate. Natural light fills the cozy yet spacious living areas, highlighting the home’s character and creating an inviting atmosphere perfect for both everyday living and entertaining. The traditional layout offers comfortable bedrooms tucked beneath charming rooflines, along with welcoming common spaces designed for gathering. This Cape Cod is more than a home—it’s a rare opportunity to own a piece of enduring design, where solid construction and original details come together in perfect harmony.

208 S Grand Avenue, Poughkeepsie

$899,000

999699 MLS

Seeking An Investment Property? Looking To Perhaps Retire....Retire Early And Have Additional Income? For Sale Is This Six Family Building Consisting Of (5) Three Bedroom Apts And (1) Two Bedroom, All With Separate Utilities (Gas & Electric). This Turnkey Property Also Includes Off The Street Parking In The Form Of A Driveway From The Front To The Rear Of The Bldg Opening Up To A Parking Area Plus (8) Garages. The Apartments Are Moderately Priced, As This Income Generated Has Been As Such For Years; With Pro Forma, The Numbers Have The Potential To Go Up. This Is An AS IS SALE Please Read Other Remarks For More Information.

242 Mansion Street, Poughkeepsie

$425,000

3 Beds ⋅ 3 Baths ⋅ 964337 MLS

Bring new life to a home rich with character and history. Original details such as hardwood floors, stained glass and chandeliers reflect its timeless charm and craftsmanship while offering a strong foundation for renovation and customization. The layout includes large sized rooms and the convenience of first floor laundry, with the washer and dryer already in place. Set on a level, double lot, the property features a fenced backyard, long driveway and a detached two car garage, providing amble outdoor space and parking. The home is ideally located with easy access to transportation, shopping, dining, medical facilities and other local amenities. Please note that the photos were taken when the home was furnished. The property will require updates, mostly on the outside of the home and the garage, and may be best suited for a renovation/rehab loan or cash. Buyer will be responsible for obtaining a certificate of occupancy, agent has the list of requirements. Current condition of home is not reflected in these photos, photos are from a previous listing. Home is being sold AS IS.

105 Hooker Avenue, Poughkeepsie

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