Dutchess Homes with Covered Parking features

Welcome to Dutchess County, New York—a picturesque gem nestled in the heart of the Hudson Valley. Known for its stunning landscapes, rich history, and vibrant communities, Dutchess County offers a unique blend of rural charm and urban convenience. With its rolling hills, scenic river views, and charming small towns, it’s no wonder that this region has become a sought-after destination for homebuyers looking for a peaceful yet engaging lifestyle.

One of the many appealing features of homes in Dutchess County is the availability of properties with covered parking. Imagine coming home after a long day, greeted by the convenience of a sheltered space for your vehicle. Whether you’re looking for a cozy garage or a carport, these homes provide not only protection from the elements but also added security for your vehicle. Covered parking is especially valuable in this region, where winter weather can bring snow and ice, and summer storms can pop up unexpectedly.

In Dutchess County, you’ll find a variety of homes that cater to different lifestyles, from charming historic houses in Poughkeepsie to modern retreats in Beacon. Enjoy easy access to outdoor activities, local wineries, and cultural attractions, all while having the peace of mind that comes with a home equipped with covered parking.

If you’re ready to embrace the Dutchess County lifestyle, explore the available homes with covered parking and discover how this beautiful region can be the perfect backdrop for your next chapter. Your dream home awaits!

Newest Dutchess Homes with Covered Parking features

$675,000

4 Beds ⋅ 3 Baths ⋅ 1030321 MLS

Welcome to this beautifully maintained Colonial in the desirable Bristol Woods neighborhood of Stormville. Set on a private one-acre lot, this 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and functionality. Inside, you'll find hardwood floors, multiple living areas, an inviting eat-in kitchen, and a cozy family room with a fireplace. Step outside to enjoy the large deck overlooking the private backyard. A recently installed heat pump provides efficient heating and cooling throughout the main level, while the spacious primary suite and finished lower level with a walk-out offer flexibility for today's lifestyle. Recent updates include a new driveway (September 2025) and gutter guards for low-maintenance living. Conveniently located just minutes from I-84, the Taconic State Parkway, shopping, dining, and Metro-North, this home offers privacy without sacrificing convienence.

189 Judith Drive, Stormville

$194,999

1 Beds ⋅ 1 Baths ⋅ 1011801 MLS

Welcome to this TURNKEY, bright and inviting 1-bedroom, 1-bath condominium located in the well-maintained Tivoli Gardens community. This comfortable, 2nd floor condo offers a private balcony off the bedroom with peaceful views of mature trees and beautifully landscaped grounds, creating a relaxing setting to enjoy your morning coffee or unwind at the end of the day. The unit includes a one-car garage plus additional unassigned parking space for added convenience. Residents enjoy meticulously maintained lawns, attractive common areas, and picnic tables set up in the open green fields perfect for outdoor gatherings. Ideally situated in the heart of the scenic Hudson Valley, this condominium is just a short drive from the natural beauty of Tivoli Bays, the renowned Kaatsbaan Cultural Park, and the historic Clermont State Historic Site. Enjoy easy access to hiking, kayaking, cultural events, farmers markets, charming villages, and many of the area's most treasured attractions. Whether you're seeking a full-time residence, a weekend retreat, or an investment opportunity, this condominium offers comfort, convenience, and an exceptional location in one of the Hudson Valley's most desirable areas.

45 Tivoli Gardens Unit #C45, Tivoli

$1,625,000

3 Beds ⋅ 2 Baths ⋅ 1011800 MLS

Calling all dreamers, this unique, architect-designed contemporary residence is set on 25 private, wooded acres in Millbrook, New York. Located on a pastoral country road, and neighboring one of Millbrook's grand estate properties, this offering combines exceptional architectural integrity, quality construction, and future development potential. The light-filled home is defined by soaring 30-foot ceilings and a dramatic sense of volume with Greek revival motifs throughout. The grand entry to the main level flows into an open kitchen area leading to the great room, with a stunning granite fireplace and adjacent open dining area and a generous greenhouse/sunroom which extends the living space. A balcony off the dining-room anchors both sides of the house and offers a sheltered outdoor respite for coffee or cocktails overlooking the peaceful wooded landscape. The other side leads into the guest bedroom and bath, as well as the primary bedroom suite, featuring a dressing area and walk in closet. Separate loft spaces in each bedroom can be enjoyed as open galleries, sleeping areas or reimagined as another floor to expand the interior square footage. Constructed with quarried bluestone and granite, I-beams, a seamless steel roof, custom millwork, and French limestone and oak floors, the house reflects a focus on longevity and craftsmanship. Below, a large cellar is well-suited for a workshop or studio and includes multiple storage rooms including one for wine. This level also offers flexibility for conversion into additional living space. An approximately 1,000-square-foot, four-bay garage provides substantial parking and storage. Additional on-site materials, including granite pavers, brick pavers, a granite bench, and a granite lamp post base, are included in the sale and offer opportunities for future landscape or hardscape projects. The grounds are anchored by a private garden with a granite pathway encircling a grand Robinson iron fountain featuring cranes. A spring-fed brook runs along the southern border of the property, enhancing the natural setting. Approximately 20 acres on the eastern side of the property offer development potential and the possibility of creating additional vantage points. Less than 2 hours from New York City, this Millbrook estate property combines solid architectural pedigree, superior construction and significant landholding in a much sought-after Hudson Valley location, with convenient access to the amenities of Millbrook Village, Dutchess Day School, and the wider Hudson Valley region. *Some photos virtually staged.

46 Hoxie Road, Millbrook

$498,000

3 Beds ⋅ 3 Baths ⋅ 1010116 MLS

Welcome to 2 Enderkill, a distinctive Hudson Valley retreat where natural beauty and everyday comfort come together. Nestled on a private setting surrounded by stunning rock outcroppings that create a truly one of a kind sense of character and connection to the landscape, this spacious 3 bedroom, 3 full bath home offers versatility, warmth, and room to grow. The main level features an inviting kitchen overlooking the dining area, a generous living room anchored by a cozy fireplace, and a flexible bonus room perfect as a home office, guest space, playroom, or potential first floor bedroom. Upstairs, you'll find three spacious bedrooms and two full baths, including a primary suite with its own private bath and sliding glass door leading to a secluded balcony overlooking the property. Outdoor living shines with a large deck, above ground pool, detached garage, attached carport, and an additional included .32 acre parcel, providing extra space and opportunity. Recent updates include a new roof, offering peace of mind for years to come. Perfectly positioned in the heart of the Hudson Valley, this unique property sits just minutes from Rhinebeck, Hyde Park, and Poughkeepsie, with easy access to Metro North train service for effortless commuting or weekend getaways. Enjoy the best of the region right at your doorstep, from boutique shopping and acclaimed dining to parks, hiking trails, and storied historic sites. Nature lovers and outdoor enthusiasts will love being directly across from Norrie State Park, with Dinsmore Golf Course and the iconic Mills Mansion just a short drive away. Whether you're seeking privacy, convenience, or a connection to the timeless charm and culture the Hudson Valley is celebrated for, this property delivers it all.

2 Enderkill Drive, Staatsburg

$3,850,000

7 Beds ⋅ 7 Baths ⋅ 1003365 MLS

WhistleWood Farm A rare multi-use estate set on just under 40 acres in the heart of Rhinebeck, NY. Currently operating as a successful bed-and-breakfast, event venue, and horse boarding facility, WhistleWood Farm offers exceptional flexibility for both residential and commercial buyers seeking a true Hudson Valley destination property. Comprised of three parcels totaling nearly 40 acres, the property is equally suited as a private compound, gentleman’s farm, equestrian retreat, boutique hospitality venture, or wellness-focused escape. Existing hospitality and equestrian infrastructure provide a strong foundation for continued or expanded use. The main residence spans approximately 4,500 square feet and features 5 bedrooms, 5 full baths, and 2 kitchens—offering remarkable flexibility for private living, guest accommodations, or hospitality operations. Complementing the main house is an beautifully appointed 1,500-square-foot carriage house with three bedrooms and three baths, rich in character and perfectly suited for guests, extended stays, or expanded event and hospitality use. Walking trails through the woods create a rare sense of privacy and connection to the landscape just moments from the heart of Rhinebeck Village—with its celebrated dining, farm-to-table restaurants, boutiques, and nearby Amtrak access. For the tennis enthusiast, premier tennis facilities conveniently located next door further enhance the property’s lifestyle appeal. Open meadows, mature trees, and a coveted Village-adjacent setting make WhistleWood Farm a truly rare offering—equally compelling as a private estate, hospitality investment, or legacy property in the Hudson Valley. Additional features include solar power, further enhancing the property’s efficiency and long-term sustainability.

52 Pells Road, Rhinebeck

$329,000

2 Beds ⋅ 1 Baths ⋅ 999737 MLS

Imagine a charming two-bedroom ranch situated on a gentle hill and a peaceful road in the Town of Hyde Park. The stunning stone fireplace in the welcoming living room is sure to be a highlight. Walking through the door, you’ll immediately feel a sense of calm and comfort—this is the perfect escape! The home features wood/combination floors, a hybrid electric hot water heater, a generator hookup (though no generator included), central a/c, 200 Amp service, a deck, and a smart thermostat. Plus, you’re just minutes from the Village of Hyde Park, where you can find shopping, restaurants, historic sites, schools, medical facilities, hiking trails, the Hudson River, the Culinary Institute of America, and so much more!

15 Forest Drive, Hyde Park

$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

$5,000,000

8 Beds ⋅ 13 Baths ⋅ 968589 MLS

Set high atop the storied crest of Quaker Hill, Elmwood Farm is a legacy estate where Hudson Valley history, architectural grandeur, and pastoral beauty converge. Approached by a long, winding gated drive, the property reveals itself gradually across 25.5 rolling acres before arriving at a striking Elizabethan style manor that has stood watch over the surrounding countryside for generations. Quaker Hill has long been known as one of the Hudson Valley’s most distinguished enclaves. For more than a century it has quietly attracted artists, writers, diplomats, and those seeking privacy, landscape, and a connection to history. Elmwood Farm stands among the hill’s most recognizable estates, shaped by generations of stewards who helped define the character of this remarkable hamlet. Owning Elmwood Farm is not simply about acquiring a home. It is about becoming part of the long story of Quaker Hill and carrying that legacy forward. The manor itself reflects the craftsmanship and romance of another era. Leaded glass windows cast soft light throughout the interior, while hand carved pilasters and hand painted plaster ceiling motifs reveal the artistry and attention to detail that defined the estate’s original design. Dramatic rooflines with carved timber fascia and Gothic inspired spires create a striking architectural silhouette that rises above the surrounding landscape. At the center of the home, a magnificent figured oak staircase ascends through the interior, its hand carved newel posts adorned with whimsical animal figures that speak to the individuality and charm of the residence. Gracious gathering rooms anchored by ten fireplaces provide spaces that feel both intimate and grand, equally suited for quiet evenings by the fire or lively gatherings with friends. A charming upper wing with hand painted storybook murals adds an unexpected and delightful layer of character that reflects the estate’s long and colorful history. Beyond the main residence, Elmwood Farm unfolds as a true country compound. The property includes two caretaker homes, a carriage house with groom’s quarters, a yoga studio, and a greenhouse, offering extraordinary flexibility for guests, staff, creative pursuits, or wellness focused living. The grounds themselves are equally compelling. Rolling lawns, mature trees, and sweeping views across the surrounding countryside create a sense of scale and serenity that is increasingly rare in today’s world. The landscape feels timeless, a place where mornings begin with mist rising over the hills and evenings conclude with golden sunsets stretching across the valley. For the next owner, Elmwood Farm offers something truly rare. It is an opportunity to become the next steward of one of Quaker Hill’s historic estates and to preserve a remarkable piece of Hudson Valley history while shaping its next chapter for generations to come.

618 Quaker Hill Road, Pawling

$1,295,000

4 Beds ⋅ 4 Baths ⋅ 986634 MLS

**TO BE BUILT** Welcome to The Woodlands at Hyde Park, an enclave of 20 elite homes, built by a local, well known custom home builder. All lots offer a private and bucolic setting ranging from 1 to 5+ acres. Lot 14 features the Payton Model. A Modern Farmhouse situated on over 2 acres of privacy, primary first floor en suite, 3400+ finished SQFT, 4 bedrooms, 3.5 baths, an office, loft and 260 SQFT unfinished bonus room for future gym/play room/flex space! With hardwood floors throughout the common areas, 9’ ceilings in the main level, 11’ ceilings in the great room and an open concept layout. The modern kitchen with an oversized island and walk in pantry boasts plenty of space, open to the dining area and living room. The expansive primary ensuite features walk-in closet, dual sinks, custom shower, soaking tub and tons of windows allowing ample natural light. Upstairs features a princess suite with walk-in closet, Jack & Jill bath and loft area. Two car attached front load garage and full walk out basement with 8' ceilings and full sized windows allowing tons of room for future expansion! Excellent location right in the heart of historic Hyde Park, minutes to the Culinary Institute of America, Marist College, The Walkway over the Hudson, Poughkeepsie Train Station, Village of Rhinebeck and 85 miles to Manhattan! Come build your dream home today! **PHOTOS SHOWN ARE RENDERINGS AND SIMILAR MODELS BUILT WITH OPTIONS**

14 Bear Hollow Lane, Hyde Park

$849,000

4 Beds ⋅ 2 Baths ⋅ 980285 MLS

Circa 1739, this 4BR/2BA Greek Revival blends historic character with thoughtful modern updates on 2.49 private acres. Original details include wide plank floors, handcrafted woodwork, four fireplaces(two functioning)-ideal for those who appreciate timeless architecture. The spacious eat-in kitchen offers charm with everyday functionality. A first-floor bedroom and full bath provide flexible living options. Upstairs features a large primary bedroom with a fireplace, two additional bedrooms (one currently used as a dressing room), a full bath, and a bonus room ready for your vision. Full, unfinished basement and attic add to the possibilities of expansion of this well-kept home. Outdoor highlights include gardens, multiple decks and porches, a pool, and an open barn used as a carport. A former garage offers studio or workshop potential. Recent updates include kitchen tiles, a new roof, a septic system, a boiler, an oil tank, and a new pool liner. Home to generations of Dutchess County’s most notable residents, it’s ready for its next chapter. Whether you're seeking a statement residence, a weekend retreat, or a truly distinguished legacy property, this timeless home invites you to become part of its storied history.

9 Ireland Avenue, Wappingers Falls

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