Dutchess Homes with On Street Parking features

Dutchess Homes with On Street Parking features

Welcome to Dutchess County, New York – a picturesque blend of natural beauty, vibrant communities, and rich history. Nestled in the heart of the Hudson Valley, Dutchess County is renowned for its stunning landscapes, charming towns, and a lifestyle that perfectly balances tranquility with accessibility. With the Hudson River winding through its heart, residents enjoy a plethora of outdoor activities, from hiking the scenic trails of the Appalachian Mountains to leisurely strolls along the riverbanks.

Dutchess County boasts a diverse array of neighborhoods, each with its unique character and charm. Whether you are drawn to the historic streets of Poughkeepsie, the quaint shops in Rhinebeck, or the family-friendly atmosphere of Fishkill, there’s a perfect home waiting for you. One of the appealing features of many homes in this area is the availability of on-street parking. This convenience not only enhances the ease of daily living but also reflects the welcoming community spirit that defines Dutchess County.

Imagine returning home after a day of exploring local wineries, farmers' markets, or art galleries, and finding a convenient spot right outside your door. With on-street parking, you can easily welcome friends and family, making gatherings effortless and enjoyable.

In Dutchess County, you’ll find a place that feels like home, where the beauty of nature meets the warmth of community. Discover your dream home today and embrace the vibrant lifestyle that awaits you in this enchanting part of New York!

Newest Dutchess Homes with On Street Parking features

$799,000
1031541 MLS Wassaic Commons BLDG.
Nestled in the heart of Wassaic Hamlet on Main Street, this meticulously revitalized 1920s two-story barn, spanning 10,640 SF, stands as a testament to craftsmanship and vision. Over six years, from 2017 to 2023, exceptional contractors, tradespeople, and artisans transformed this historic structure into the Wassaic Commons, a modern masterpiece, blending rustic charm with state-of-the-art functionality. The iconic green barn, with HM zoning, offers a versatile canvas for a variety of uses, including office space, retail, arts instruction, studios, workshops, or storage, making it an ideal investment for entrepreneurs and creatives alike. The first floor, encompassing 5,320 SF, is thoughtfully divided into 3 distinct spaces. On one side, a 1,200 SF area houses an 800 SF market space and a 400 SF commercial kitchen, currently leased to the renowned Vitksy Bakery. On the opposite side, 3,600 SF of retail space, currently operates as the Wassaic Farmer’s Market. The seasonal farmers market is open from May until the end of October, Friday through Sunday. 22 tables covered in burlap tablecloth set the stage for local businesses to showcase a diverse range of items including farm fresh vegetables and eggs, artisanal breads, distinctly designed floral arrangements, health, healing and beauty products, to name a few. At the center, a 520 SF section includes an office, 2 bathrooms, and mechanical systems, providing essential infrastructure for seamless operations. The second floor, also 5,320 SF, features 3,600 SF of raw space brimming with potential for customization. The loft’s 20-foot ceilings are adorned with a breathtaking lighting design inspired by the constellation of Polaris, Ursa Minor, and neighboring stars, with fixtures suspended at varying heights, sizes, and brightness. The timbers on this floor boast a charred finish that is naturally resistant to mold, mildew, and insects, adding aesthetic allure and durability. This is an ancient Japanese technique known as shou sugi ban. The remaining 1,720 SF is currently utilized for mechanical systems and storage on the second floor. The barn’s transformation included extensive upgrades to ensure modern efficiency and comfort. Custom cabinetry, paneling, and millwork, crafted by master carpenters, elevate the interior, with careful attention to acoustics for an optimal environment. The structure itself has been rigorously evaluated by structural engineers, architects, and timber specialists, ensuring its integrity and longevity. Outside, the barn’s exterior was scraped and painted, with reclaimed planting areas, cleared views of the bordering stream, outdoor seating, and bicycle racks creating an inviting destination for residents and visitors. A concrete sidewalk connects the barn to a 748 SF storage shed, which houses a 12 x 6 commercial-grade walk-in cooler and additional storage space. Located just steps from the Wassaic Art Project, the Lantern Inn, Ten Mile Table, Calsi’s General Store and the local post office, this property is centrally positioned between Amenia, Millbrook, Millerton, Kent, Sharon, and Pawling. Its proximity to the Wassaic Metro North Train Station, the final stop on the Harlem line, and Route 22 make it a convenient 2-hour journey to NYC by car or train. For outdoor enthusiasts, the barn marks the starting point of the Harlem Valley Rail Trail, offering 46 miles of paved trails for bicyclists. This extraordinary property, blending historic charm with modern innovation, is a rare opportunity to own a versatile and vibrant cornerstone in the heart of Wassaic Hamlet.

3 Main Street, Wassaic

$299,900
4 Beds 2 Baths 1027461 MLS
STOP RENTING & START OWNING! COMPLETELY TURN-KEY 4-BEDROOM COLONIAL! Why pay a landlord when you can own this spacious, updated 4-bedroom, 1.5-bathroom single-family Colonial for less than the cost of local rent? Boasting 1,600 square feet of vibrant, sun-drenched living space, 20 Grant Street is the definition of "move-in ready." THE LAYOUT YOU WANT: Say goodbye to cramped quarters! The flexible 7-room floor plan features a highly coveted main-level bedroom option—perfect for a home office, guest space, or playroom—plus three additional oversized bedrooms upstairs. INTERIOR HIGHLIGHTS: Enjoy modern, seamless flooring throughout, natural gas cooking, and a floor plan built for everyday living. Out back, a private backyard space and balcony offer the perfect retreat for summer BBQs or morning coffee. Need storage? The partial basement has you covered. ULTRA-CONVENIENT CITY LIVING: Say goodbye to utility headaches. This home features high-efficiency natural gas forced-air heating, city water, city sewer, and low-maintenance on-street parking right at your front door. Located seconds from downtown shopping, hospitals, local parks, and major commuter routes. THE BOTTOM LINE: Whether you are a first-time homebuyer looking for space to grow or a savvy investor hunting for a high-yield, turn-key rental with zero renovations needed—this is the property you’ve been waiting for.A property this clean at this price point will not last. Don't wait—schedule your private tour today!

20 Grant 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

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