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

$599,000

3 Beds ⋅ 3 Baths ⋅ 1050226 MLS

Discover a property that offers comfortable one-level living, impressive outdoor spaces and an exceptional detached garage at 158 Robinson Lane. Set on approximately 0.92 acre, this spacious ranch features three bedrooms, a welcoming living room with fireplace, and an updated kitchen with rich cabinetry, butcher-block countertops, stainless-steel appliances and an adjoining dining area. Hardwood flooring extends through much of the main living space, while the primary suite includes a generously sized private bath with an expansive tiled, glass-enclosed tub and shower area. The outdoor setting is designed to be enjoyed. A broad rear deck leads to an extensive patio with a covered gazebo and a striking stone outdoor fireplace, creating multiple areas for dining, entertaining or relaxing. The level lawn provides additional usable outdoor space, and a walk-in cooler located on the property offers a distinctive feature with possibilities for food storage, catering, gardening or other permitted uses. A major highlight is the oversized detached two-bay garage. Measuring approximately 22 by 34 feet, it is equipped with heat, air conditioning and a half bath, along with substantial upper-level attic and storage space. Whether used for vehicles, equipment, a workshop, recreation or another legally permitted purpose, this versatile building adds tremendous functionality to the property. The location provides convenient access to Route 55, the Taconic State Parkway, Route 9 and Interstate 84, placing shopping, dining, services and regional transportation routes within comfortable reach. With its flexible layout, extensive outdoor improvements, specialized storage and unusually well-equipped detached garage, 158 Robinson Lane offers features rarely found together in one property.

158 Robinson Lane, Wappingers Falls

$629,900

3 Beds ⋅ 2 Baths ⋅ 1048227 MLS

Welcome to 8 Caroline Dr. W, Wappingers Falls, NY a peaceful ,warm single family home. It's charm stems from the peace you feel when you walk in.This offers country living at its best and yet its not to far from local bars, restaurants and lots of shopping. If you enjoy nature please come home to me.

8 W Caroline Drive W, Wappingers Falls

$649,000

4 Beds ⋅ 3 Baths ⋅ 1048481 MLS

Picture perfect move-in condition on a cul-de-sac within the sought after Arlington Central School district. This 4 bedroom, 2.5 bath beautifully maintained Split-Level Ranch is privately set .97 acres on a quiet country street in Poughquag. The main level features a welcoming foyer that opens to a bright and airy living room highlighted by a large picture window that fills the space with natural light and brick wall fireplace offering comfort on those colder evenings. The formal dining room provides an ideal setting for gatherings and flows seamlessly into the eat-in kitchen, where abundant cabinetry, ample counter space, and a casual dining area create a functional and inviting hub of the home. Upper level consists of 2 bds & a full hall bath in addition to the primary suite. The finished lower level significantly expands the living space and includes a family room. On this level you'll also find a bedroom, laundry area, half bath, storage space and access to the oversized two-car garage with attic storage above adding convenience and versatility. Outside, the impressive level yard offers plenty of room for recreation, gardening, outdoor entertaining, or simply enjoying the open space. A storage shed provides additional utility, while the large deck overlooks the expansive backyard and pool. Conveniently located in the Town of Beekman, this property offers easy access to local parks, recreation areas, golf courses, shopping, restaurants, and everyday services. Outdoor enthusiasts will appreciate the proximity to the scenic Appalachian Trail, Tymor Park, and numerous hiking and nature destinations throughout the Hudson Valley. Commuters and travelers will also enjoy convenient access to major roadways, Metro-North train stations, and destinations throughout Dutchess County and beyond.

15 Deer View Lane, Poughquag

$1,125,000

4 Beds ⋅ 3 Baths ⋅ 1044719 MLS

This exceptional log home offers a tranquil retreat on 8.8 acres, featuring a private pond and a park-like setting. The property emphasizes privacy and includes an inground pool with a deck for outdoor enjoyment. Additionally, it boasts a substantial workshop with a one-bedroom guest quarters located above it, providing versatile extra space. Another run-in shed offers further utility storage. The location is highly desirable, offering the serenity of a private estate while remaining just minutes from the charming Rhinebeck village and convenient access to the Taconic Parkway.

331 Mountain View Road Unit #325, Rhinebeck

$1,699,999

5 Beds ⋅ 5 Baths ⋅ 1047350 MLS

Prepare to be captivated by this one-of-a-kind 5 bedroom, 4.5 bath luxury estate in the prestigious Old Hopewell Estates—an extraordinary residence that seamlessly blends elegance, privacy, and resort-style living with town water/sewer and low taxes. Perfectly sited on a manicured 1-acre corner lot, this custom Colonial boasts over 6,000 sq. ft. of refined living space plus a fully finished 1,700+ sq. ft. walkout basement designed as a true mother/daughter or multi-generational suite with its own full kitchen, spacious living and dining areas, luxury bath, private laundry room, fireplace, and direct access to the backyard—making it completely self-sufficient for extended family or guests.ONLY For the most discerning buyers--- From its commanding brick facade, stone-accented driveway, and double-door entry to the soaring two-story foyer with dual staircases, hardwood floors, and intricate millwork, every detail radiates sophistication. The main level is designed for both grand entertaining and everyday comfort, featuring elegant formal living and dining rooms, a coffered-ceiling family room with fireplace, and a sun-filled home office. The gourmet kitchen is a showpiece with a massive quartz island, professional-grade appliances, custom cabinetry, and a garden window overlooking the lush grounds, flowing seamlessly to a dramatic breakfast area and expansive patios. Upstairs, the primary suite is a private retreat with sitting room, dual custom closets, fireplace, and a spa-inspired bath with limestone floors, soaking tub, and oversized walk-in shower, while four additional bedrooms include a princess suite and Jack & Jill accommodations. Step outside to your own resort-style paradise—a heated saltwater pool with natural stone accents, multiple stone-paver patios, an outdoor kitchen, European-style gazebo, tranquil fountain garden, and cozy firepit lounge, all surrounded by professional landscaping for ultimate seclusion. Additional highlights include a heated/air-conditioned 3-car garage, whole-house sound and security systems, and a commuter-friendly location just 5 miles to Metro-North and 75 miles to Manhattan. Combining timeless elegance with unmatched functionality, this estate is the crown jewel of Old Hopewell Estates—a forever home offering true multi-generational living, luxury, and lifestyle.

144 Shamrock Hills Drive, Wappingers Falls

$999,999

6 Beds ⋅ 6 Baths ⋅ 998000 MLS

1920s Victorian Splendor with Exceptional Possibilities - Step into the timeless elegance of the 1920s at 104 Hooker Avenue, a distinctive Victorian property offering an impressive combination of historic character with gorgeous period woodwork, space, and future potential on almost one acre. Featuring six bedrooms, six bathrooms, and parking for 10+ vehicles, this extraordinary property provides the scale and flexibility rarely found in the area. Original architectural charm and classic Victorian details create an inviting backdrop for a variety of possibilities, while the generous property and expansive footprint offer room to imagine something truly special. Whether you're looking for an exceptional residence, an investment opportunity, or a property with potential for an alternative use, 104 Hooker Avenue deserves a closer look. Adding to the appeal is the property's potential for subdivision with its large, wooded frontage, subject to municipal review and approvals. There may also be an opportunity for a quiet-use professional or business application, subject to required approvals. With its grand proportions, abundant parking, substantial grounds, and coveted Victorian character, 104 Hooker Avenue presents an exciting opportunity to own a piece of Poughkeepsie's architectural history while exploring its future potential. Bring your vision and unlock the possibilities of this remarkable property. *Note - Some photos have been Virtual Enhanced

104 Hooker Avenue, Poughkeepsie

$1,695,000

3 Beds ⋅ 3 Baths ⋅ 1045384 MLS

Set on a newly developed parcel within the highly coveted Fox Lane neighborhood that is adorned with luxury properties, this modern country home captures the essence of Hudson Valley living, with clean architectural lines softened by rolling pastoral hills and open meadow views. Designed specifically to capture the elements of five private acres and oriented to the south, the home is bathed in natural light from morning through golden hour, creating a sense of warmth and calm that feels both elevated and effortless. Inside, the layout is as functional as it is beautiful. Wide plank french oak flooring runs throughout, grounding the home in a natural, cohesive palette, while custom cabinetry and refined finishes elevate every space. The main living area is anchored by a sleek fireplace that offers a focal point for gathering and keeps things cozy. The modern kitchen flows seamlessly into a butler’s pantry, perfect for entertaining or keeping daily life tucked away. Beautiful countertops compliment the large center island that is ideal for that morning cup and watching the sun rise. A dedicated laundry and mudroom with custom built-ins adds practicality without sacrificing design. On the right wing, a primary suite is a true retreat, featuring a spa-like ensuite with an oversized soaking tub positioned in front of a large picture window, and double vanity. Two additional bedrooms and a well-proportioned layout provide flexibility for guests, work-from-home needs, or weekend hosting. Additional highlights include attic storage and a private dry sauna, bringing a layer of wellness and luxury to everyday living. Easily add a pool and an additional structure to create that true compound vibe. Located just minutes from the heart of Tivoli and the campus of Bard College, Fox Lane offers the rare combination of quiet countryside living with access to one of the Hudson Valley’s most vibrant cultural pockets. Enjoy proximity to beloved local spots like The Corner, Fortunes Ice Cream, and Traghaven Whiskey Pub & Co., along with nearby Rhinebeck and Red Hook for even more dining and shopping options. Convenient access to the Taconic State Parkway and Amtrak service from Rhinecliff makes travel to and from New York City seamless, just under two hours door to door.

74 Fox Lane, Tivoli

$449,888

3 Beds ⋅ 2 Baths ⋅ 1045349 MLS

Welcome to this spacious, move-in-ready single-story ranch nestled in desirable Colburn Estates! This well-maintained home offers numerous updates, comfortable living spaces, and excellent flexibility for today’s lifestyle. The main level features beautifully refinished hardwood floors throughout, a welcoming living room with a wood-burning fireplace, and California-style floor-to-ceiling windows with an exterior walk-out door providing an abundance of natural light and easy access to the yard. The sunken dining room addition is a wonderful gathering space, featuring newly installed 30"x 54" skylight with copper flashing and a new wall A/C unit installed in 2026. The kitchen offers quartz countertops and a gas cooktop, while both bathrooms were tastefully remodeled in 2018. Replacement windows on the main level are approximately 20 years old. Numerous improvements provide added peace of mind, including new vinyl siding installed in 2024, a recently power-washed exterior, architectural roof shingles installed in 2014, and new 5" gutters with stainless-steel mesh gutter guards. The home also benefits from additional insulation, including 3/4" foam board added with the siding installation and R-30 attic insulation. Four brand-new basement windows have recently been installed, and the main level and garage have been freshly painted. The lower level offers tremendous potential with a separate side entrance and a large unfinished area that can be customized to suit your needs. Create a home office, potential fourth bedroom, guest space, or explore a potential mother-daughter setup, subject to necessary approvals. There is also ample room to add another bathroom. Home is serviced with 200-amp electrical service adds further convenience. The oversized two-car garage addition features a side entrance and additional attic storage with a new metal attic door. The basement provides abundant storage, with the freezer included in the sale. A 7' x 10.6' storage shed provides even more outdoor storage. The Burnham furnace was installed in 2009 and converted from oil to natural gas in 2013; the oil tank was removed at that time. Municipal water and sewer and natural gas heat add to the convenience. Appliances include refrigerator (2008), wall oven (2009), washer and dryer (2018), and dishwasher (2020). Freezer stays, Ideally located with easy access to Route 9, shopping, supermarkets, and commuting options. The Poughkeepsie Metro-North station is approximately 5.9 miles away. With its generous spaces, extensive updates, flexible lower level, and convenient location, this home truly spells Home Sweet Home!

80 Colburn Drive, Poughkeepsie

$649,000

4 Beds ⋅ 3 Baths ⋅ 1044908 MLS

Welcome to 24 Deer Run Road, a beautifully designed new-construction bi-level tucked away on a quiet cul-de-sac in an established neighborhood within the Wappingers Central School District. Offering four bedrooms, three full bathrooms and a spacious, thoughtfully planned layout, this home blends modern style with everyday comfort. The bright and inviting main level features hardwood flooring throughout, with soaring cathedral ceilings connecting the kitchen, dining area and living room. This open-concept space is ideal for everyday living and entertaining, with direct access to a rear deck. The private primary suite provides a peaceful retreat with its own full bathroom and walk-in closet. Two additional bedrooms and a second full bathroom complete this level. The finished lower level features durable vinyl flooring, a generously sized family room, fourth bedroom, third full bathroom, separate laundry room and direct access to the oversized two-car garage. This versatile space is perfect for guests, a home office, recreation room or additional living area. Outside, the property offers a comfortable backyard, a large side yard and a wooded backdrop that creates a wonderful sense of privacy. There is plenty of room to relax, entertain, garden or simply enjoy the peaceful natural surroundings. Enjoy everything Dutchess County and the Hudson Valley have to offer, including nearby parks, hiking trails, Hudson River recreation, local farms, markets, restaurants and cultural attractions. Conveniently located near Route 9, shopping, dining, medical facilities and Metro-North train service, with easy access to Poughkeepsie, Wappingers Falls, Beacon and other popular Hudson Valley destinations. Estimated completion is approximately three months, and there is still time for the buyer to select certain finishes and add personal touches to their new home.

24 Deer Run Road, Poughkeepsie

$599,900

4 Beds ⋅ 3 Baths ⋅ 1043586 MLS

Pre-qualified buyers only please. This unique home is being offered for the first time in over ten years and it's a lot of house for the money. All large sized rooms on an oversized lot located at the end of a lovely street just minutes from everything. The entrance foyer has built in planters and an entire wall of custom stonework that opens up to an oversized living room with the same stonework and woodstove insert- even the wood is included for next winter's burning. There is a nice sized kitchen with a center island, and the laundry room is conveniently located right in the same room for your ease!! The dining room is there as well and has a bow window and even a built-in ironing board from the old days with a door out to the massive wrap around deck that overlooks the inground Gunite pool. There are two bonus rooms with parquet floors off of the dining area and the living room with pocket doors that are currently being used as an office and an exercise room. The home allows for anyone to choose how to use the different rooms for their individual needs and taste! The main floor has a large primary bedroom with a full bath, two additional bedrooms, and a bathroom in the hallway with double sinks. On the lower level, there is a massive fourth bedroom, a full bathroom that opens to the outside to facilitate easy access to the pool, and storage galore. There is also a large family room with a built-in bar, a non-working second wood burning fireplace insert, and a large pool table room that is not heated. There is also a large room for mechanicals and storage galore and a utility room as well. The space inside this custom home and its unique features will surprise you and the pictures don't do it justice. Outside there is a pool house, large decking overlooking the pool, and a few patios to choose from. One of the best features of this home is the detached garage with multiple doors and a full walk up to a second story. A car enthusiast or hobby person could spend years deciding on its best use or change their plans as the need arises!! The solar power is fully paid for and off sets the utility bills- we are currently looking into whether the current credit will be transferable to the new owners.

58 Ireland Drive, Poughkeepsie

$655,000

3 Beds ⋅ 3 Baths ⋅ 1041481 MLS

Set on nearly two acres just a few miles from the village of Pawling, this log home offers space, privacy, and real potential for the right buyer. The in-ground concrete pool and detached three-car garage add value rarely found together at this price point. Inside, the open kitchen and vaulted wood ceilings give the home a warm, cabin-like character that is hard to find in newer construction. This home is being sold as is and priced to reflect its current condition and status. The space above the garage is finished but is permitted and approved for storage use only. It is not being represented as legal living space, and any potential alternate use should be independently verified by the buyer with the Town of Pawling. The lower level is currently the subject of an active permit application to be finished, and its status should also be verified directly with the Town prior to closing. A solar panel system is installed on the property but is not currently connected to the grid. Reinstallation and reconnection through Tesla is scheduled, and buyers should confirm current status and any associated costs or timelines directly with Tesla. Given the acreage, the pool, and the bones of this home, there is a lot here for a buyer willing to do some homework. Priced at $655,000 to reflect the property's current condition and open items.

12 Rebecca Drive, Pawling

$799,000

3 Beds ⋅ 1 Baths ⋅ 1037836 MLS

Set on an impressive 13.5 acres, this well-maintained 3-bedroom, 1-bath ranch presents a rare opportunity for those seeking space, privacy, and future possibilities. Lovingly cared for over the years, the home offers comfortable one-level living in a peaceful setting with abundant room to enjoy the outdoors, create gardens, add recreational space, or simply appreciate the privacy of over 13 acres. Offered for the first time in more than 50 years, the property features substantial road frontage and potential for subdivision into 2–3 additional building lots, offering an exciting opportunity for future development. Conveniently located near the Taconic State Parkway, I-84, and area amenities, this unique offering combines a well-cared-for home, expansive level acreage, and exceptional potential.

2776 Route 52, Hopewell Junction

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