Dutchess Homes with Oversized Parking features

Dutchess Homes with Oversized Parking features

Welcome to Dutchess County, New York – a picturesque region that beautifully blends natural beauty with vibrant community life. Nestled in the heart of the Hudson Valley, Dutchess County is known for its stunning landscapes, charming small towns, and rich history. With the majestic Hudson River winding through its heart, residents enjoy an abundance of outdoor activities, including hiking, biking, and exploring the numerous parks and nature reserves.

Dutchess County is home to a diverse array of communities, each with its own unique character. From the bustling streets of Poughkeepsie, the county seat, to the quaint charm of Rhinebeck and Beacon, there’s a perfect neighborhood for everyone. Enjoy local farmers' markets, art galleries, and historic sites, all while being conveniently located just a short train ride from New York City.

For those seeking homes that offer both comfort and practicality, Dutchess County boasts an impressive selection of properties featuring oversized parking. Whether you have multiple vehicles, enjoy outdoor hobbies that require extra space, or simply appreciate the convenience of ample parking, these homes are designed with your needs in mind. Imagine arriving home to a spacious driveway that accommodates your cars, RVs, or even a boat, making weekend getaways a breeze.

Embrace the idyllic lifestyle of Dutchess County, where stunning homes with oversized parking await you. Experience the perfect blend of rural charm and urban convenience in this delightful corner of New York. Your dream home is just around the corner!

Newest Dutchess 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

$699,000
3 Beds 3 Baths 1029600 MLS
A rare Pawling hilltop retreat with panoramic views & endless potential! Opportunities like this are extraordinarily hard to come by. Perched high to capture breathtaking, miles-long panoramic vistas, this true "sunset house" offers an idyllic Hudson Valley lifestyle centered around big skies, rolling hills, and complete tranquility. Imagine sitting on the expansive covered patio with your favorite beverage looking out into the vibrant sunset, or lounging by the crystal-clear in-ground pool, sunbathing while overlooking nearby farms and sparkling lakes. This property was built for unforgettable outdoor living and limitless entertaining. Inside, the home is a clean-cut, light-filled ranch featuring three bedrooms and two-and-a-half bathrooms. The expansive living room serves as the heart of the home with its classic brick wood-burning fireplace, two huge picture windows framing the valley skyline, and sliding glass doors that open directly onto the massive patio. Adjacent, the kitchen is outfitted with high-end cabinetry and modern stainless steel appliances, opening seamlessly to a bright dining area framed by another impressive picture window. The primary bedroom offers its own private half bath, while a hallway closet conveniently houses the main-level laundry. Downstairs, the finished walk-out basement expands your living space with two versatile rooms perfect for a home theater, gym, or guest quarters, complemented by a full bathroom and abundant storage space. Spanning over 4.5 acres, the grounds offer exceptional privacy along with rare long-term flexibility. Whether you envision expanding the existing home or exploring options to subdivide and sell or build a second residence, this property delivers a quintessential Pawling sanctuary where indoor ease meets endless horizon.

21 Overlook Drive, Pawling

$799,000
4 Beds 3 Baths 1029249 MLS
Rare opportunity to own this historic farmhouse colonial perfectly situated on a quiet, private yard with beautiful, scenic golf course views! Whether you're looking for a multi-generational living arrangement, an income-producing investment, or extra space for guests, this unique property offers incredible flexibility. Inside the main space, you will notice the warmth and craftsmanship of a bygone era, showcased through beautiful original woodwork and timeless hardwood floors. The spacious main level boast a large dining room with a built-in bar, a bright sunroom with access to the outside, and a comfortable family room centered around a cozy pellet stove. This family room opens directly into an oversized, casual eat-in kitchen complete with a skylight, a large walk-in pantry, and direct access to the backyard. The upper floor master bedroom features a beautiful, original decorative fireplace and classic hardwood floors. The layout also includes one additional bedroom, a dedicated office/flex space, plus a massive bonus area which can be used an extra-large bedroom, play space, or media room that comes complete with its own walk-in closet. Adding incredible value to the property is the attached, completely updated apartment, which includes a beautiful stone fireplace and a large bedroom. The outdoor spaces match the impressive scale of the interior with a brand-new back patio to grill, relax, or take in the golf course views. The property also features a detached, oversized 2-car garage equipped with extra workshop and loft space, offering more than enough room for your vehicles, heavy tools, storage, and weekend hobbies. Town sewer and water add to the appeal of this home! Easy access to Taconic State Parkway, route 9 and local shopping make this location truly perfect. Come see this home to truly appreciate what it has to offer!

6 Country Club Road, Hopewell Junction

$149,888
2 Beds 2 Baths 1030143 MLS
Welcome to Hidden Brook Estates, a well-maintained and desirable co-op community offering affordable living in a lovely neighborhood setting. This spacious Ritz-Craft-Centennial model, 24x48 manufactured home (built in 1986) set on one of nicest lot with park-like setting. Home features 2 bedrooms, 2 full baths, and an open, airy floor plan. Step inside to find a high vaulted ceiling in the living room, flowing seamlessly into the dining area – perfect for entertaining or everyday living. Many replacement windows ( approx 2004) bathe the space in natural light, creating a bright and welcoming atmosphere. The kitchen offers ample cabinetry, countertop space and walk-in pantry closet with a convenient rear door leading to a deck (overlooks woods) is ideal for relaxing outdoors or for your BBQ grill. Dining room has an extra large built-in China cabinet for your dishes & silverware. The primary bedroom includes an ensuite bath with walk-in shower remodeled less than 4 years old and heat lamp as you come out of the shower and linen closet for your towels. Second bedroom located on the other end of the home gives privacy, newly installed wall to wall carpeting and has a walk-in closet. Both bedrooms have ceiling fans. Hall bathroom has new bath tub and new vinyl flooring. The home also features a laundry area with side-by-side washer and dryer (included). Outside, enjoy the privacy with park like backyard area surrounded by mature shrubs & woods. A storage shed 10x12 with electric for your workshop and gardening tools. Parking for three cars on the expanded paved blacktop driveway that was extended. Approx updates: roof replaced (2003), central air (original and still runs), Thermo Pride furnace (2020), windows (2006) and brand new 50 gallons electric hot water heater. Nice front steps replaced about 8 years ago with vinyl handrails. Lot rent $500 per includes school and county taxes, water, sewer, garbage & main road snow removal. You are responsible for clearing the snow from your driveway and walkway and mow the lawn around the house. Playground nearby on Kens Way Extension. Co-op requires 700 credit score, $1,500/monthly income & Board approval before contracts will go out. Cash or mobile home financing only. Flood insurance required by lender. This is an estate listing, home sold as-is. Inspection for information purpose only. Affordable, well-maintained community—why rent when you can own? Use ShowingTime to book your appt. Buyer must be owner occupied to live at the HBE Community.

35 Perry Road, Hyde Park

$599,000
2 Beds 2 Baths 1026621 MLS
This sprawling expanded ranch, set back on a long drive and surrounded by beautifully landscaped grounds, is a rare offering that combines exceptional craftsmanship, thoughtful design, and an unbeatable Hudson Valley location. Quality contractor-owned and meticulously maintained, pride of ownership is evident throughout. The show-stopping living room features dramatic exposed truss-style beams, skylights that fill the space with natural light, and a wood stove set on a cozy brick hearth. A stunning oversized entry foyer showcases 10" wide yellow pine flooring and connects two distinct living areas, creating an ideal floor plan for extended family, multigenerational living, or a private guest, teen, or in-law suite. This 2BR home really lives like a 4BR plus. The oak kitchen is designed for everyday living and entertaining, offering stainless steel appliances, a breakfast bar, breakfast nook, and beautiful, durable terra cotta flooring that opens seamlessly to the great room. Outdoor living is just as impressive with a spectacular three-level multi-tiered deck, delightful bluestone patio with fire pit, and unilock paver accents, perfect for relaxing or entertaining while enjoying the peaceful surroundings. Additional highlights include deeded lake rights, an oversized heated three-car garage with expansive driveway parking, and an immaculate unfinished basement offering abundant storage and incredible potential for future expansion. Ideally located just minutes from the Omega Institute, the Village of Rhinebeck, the Taconic State Parkway, and all the shopping, dining, recreation, and cultural attractions the Hudson Valley has to offer. With sought-after Rhinebeck schools, low taxes, and an incredibly versatile floor plan, this meticulously maintained home offers the perfect blend of comfort, quality, and convenience. Whether you're entertaining a crowd, accommodating extended family, looking for room to grow, or searching for the ideal heated three-car garage for your vehicles, hobbies, or workshop, this exceptional home is designed to meet your needs today and for years to come.

70 Camp Drive, Rhinebeck

$595,000
4 Beds 2 Baths 1026736 MLS
Beautifully Modernized and Expanded 2,426sqft, 4-Bedroom California Ranch, nestled in Barnegat Estates has much to offer. In 2006 the Homeowners built an addition with a 2 car, 768sqft Workshop/Garage and a 576sqft Living Room over it. Main Level offers 3 Bedrooms, a Gorgegous Full Bathroom with Corian Counters, Stylish Finishes, Subway Tile and Skylight. Spacious Living with room to grow. Large Formal Dining, Eat-In-Kitchen and Living Room. Kitchen offers Beautifully Tiled Floor, Corian Counters, Maple Cabinets, Stainless Steel Appliances, Cook's Window, Breakfast Island, SkyLight, Desk/Sitting Nook and French Doors to the Living Room. The Living Room is next to nature with 3 walls of windows, a great space for large gatherings around the Gas Fireplace. Sliding Glass Doors to Deck with Awning for a cool breeze in the shade, with quick access to yard and Gardens. Mother/Daughter with first Level Entry, offers 768sqft, 2 Rooms, Gas Fireplace, Walk-In-Closet, Renovated Full Bathroom w/Shower, Laundry, Kitchenette Nook and Addt'l Storage. Making it a perfect home for those seeking more space, larger rooms, additional Garages, a heated Workshop, or a Mother/Daughter layout. Situated on a Beautifully manicured .25 of an acre, offering ready to grow Garden Beds, Shade Trees and absolutely gorgeous Mature landscaping. 275k Addition 2006 New Siding 2006 New Roof 2020 New Boiler 2024 New Bathrooms 2025 New Water Heater 2026 Well Maintained Beautifully Renovated Lots of Natural Light Skylights Beautifully Tiled Hardwood Floors Heated Workshop Bonus Garage Space Central Location Close to IBM, Major Shopping, Parks, Schools, Hospitals, Colleges, Restaurants, Spratt Park/McCann Golf Course and only 6 miles to Metro North!

23 Hankin Loop, Poughkeepsie

$785,000
5 Beds 4 Baths 1025832 MLS
Rich in history and character this 1820 farmhouse offers 5 bedrooms and three and a half baths a total of 4616 finished square feet in the main residence. Gorgeous wide plank floors, many windows, 2 staircases, tucked away rooms add to the charm and coziness of this home. Throughout the house the historic details add to the welcoming feeling, however thoughtful renovations including all the bathrooms and the attentive and continual maintenance including the addition of insulation in the walk-up attic and the basement the 10,000-watt whole house generator create a sense of modern comfort. A private and versatile east wing can be closed off from the house creating an ideal guest suite complete with a living/family room, bedroom and full bath. This area has three skylights, a propane stove, private entrance and a door to the private deck and back yard. In addition to the main home there is a self-contained 2 bedroom, 1. 5 bath apartment. This space can be accessed through an enclosed hallway from the house and also through an independent door. Originally finished in 1994 this 1000 finished square feet apartment has been recently renovated with radiant heat, new boiler in 2024, a washer/ dryer and the metal roof was repainted in 2025. The countertops are new and tile was installed in the full bath. This is a great space for, extended family, guests, a nanny or as an income producing opportunity. Outside the impressive three bay barn is a destination in itself. Equipped with electricity, water and a second floor it offers endless possibilities for hobbyists, artists, or storage. As a delightful conversation piece, the barn’s striking oversized front windows was salvaged from the legendary James Cagney Stage Stop Restaurant, adding another unique chapter to this remarkable property’s story. The 1.11-acre property is a lovey combination of open, mostly level yard, trees and gardens enhanced by private decks to the back and side of the property. Surrounded by the beauty of the Hudson Valley and tucked just beyond farmland, it is conveniently located with easy access to the Taconic Parkway and effortless travel just a short distance from the regions many farm markets, wineries, cultural attractions and charming villages.

2327 Salt Point Turnpike, Clinton Corners

$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

$850,000
5 Beds 3 Baths 1022034 MLS
Welcome to 289 Oak Ridge Road, a sprawling 5-acre estate property offering exceptional space, flexibility, and long-term potential in Hopewell Junction. With approximately 5,791 square feet of gross living area across two levels, this expansive residence provides a rare combination of indoor scale, outdoor amenities, and possible future upside. The main house features a flexible layout with multiple bedroom, office, den, and living area configurations, making it well-suited for a variety of lifestyle needs. The interior includes an oversized open kitchen and family room area, multiple living rooms, a large den, library/office space, and a spacious primary suite with additional adjoining rooms, office nook, sliding glass doors to the rear deck, and convenient flow back toward the kitchen area. A second kitchen on the lower level adds further flexibility for extended household use, guest space, or potential separate living arrangements, subject to verification and applicable approvals. The outdoor setting is equally impressive, with an in-ground pool, tiered decks, porches, wraparound outdoor living areas, a basketball court, pool house, additional recreational building, two sheds, and a large play structure. The property offers abundant room for entertaining, recreation, storage, gardening, hobbies, or future planning. Currently understood to be zoned for two-family use, the property may offer additional long-term possibilities. The separate apartment-style building appears large enough to potentially be reconfigured into two apartments, with one on the first floor and one on the lower level. There may also be potential to evaluate whether the main residence and accessory/apartment structure could be treated separately, depending on zoning, certificate of occupancy history, parcel configuration, septic capacity, parking requirements, code compliance, and municipal review. Whether used as a spacious private residence, multi-generational setup, income-producing opportunity, or long-term redevelopment play, 289 Oak Ridge Road offers a unique combination of land, scale, amenities, and possibility. Buyer to complete all due diligence regarding permitted uses, rental potential, subdivision potential, conversion options, and required municipal approvals.

289 Oak Ridge Road, Hopewell Junction

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