Wappingers Homes with Oversized Parking features

Welcome to the Wappingers School District, a vibrant and nurturing educational community nestled in the heart of Dutchess County, New York. Known for its commitment to academic excellence and holistic development, the Wappingers School District serves a diverse student population across several well-equipped schools. With a strong emphasis on innovative teaching methods, dedicated educators, and a wide array of extracurricular activities, this district is designed to foster a love for learning while preparing students for success in an ever-evolving world.

Families who choose to call Wappingers home will appreciate not only the quality of education but also the inviting neighborhoods that surround them. One of the standout features of many homes in this area is the availability of oversized parking spaces. Whether you have multiple vehicles, enjoy hosting gatherings, or simply need extra room for recreational vehicles, these properties offer the convenience and flexibility that today’s homeowners desire. Imagine coming home to a spacious driveway or a garage that can accommodate not just your car, but also your hobbies and adventures.

Living in Wappingers means you’re not just investing in a home; you’re investing in a community that values education, growth, and family. With beautiful parks, local shops, and a friendly atmosphere, it’s no wonder that families are drawn to this charming area. Explore the possibilities of your future home in Wappingers, where quality education meets the comfort of oversized parking solutions, making everyday living a little easier and a lot more enjoyable.

Newest Wappingers Homes with Oversized Parking features

$599,000

3 Beds ⋅ 2 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

$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

$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

$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

$537,500

3 Beds ⋅ 3 Baths ⋅ 1030461 MLS

Welcome to 38 West Taconic Drive, a rare brick corner lot charmer in the desirable Hillside Lake neighborhood of Wappingers Falls, offering its next owner the best of both worlds: quiet country living with less than a five minute drive to the Taconic State Parkway. Impeccably maintained by its current owners, the home offers three bedrooms and baths, a formal dining room and multiple living areas, including a bonus room that opens to the yard. Two fireplaces, one on each level, add to further warmth and charm. The home features a modern kitchen, updated baths, yet retains its rustic charm throughout, paying homage to its country roots. The home boasts new central air with a heat pump, offering electric or oil heating options, quality designer lighting throughout the home. which will transfer with the sale, newer, updated windows & septic system. Outside, the backyard is an entertainers'paradise: the fenced in back yard is divided into multiple outdoor entertaining spaces and comes complete with an outdoor fireplace and raised deck to be converted to accommodate the many visitors who will flock to your home. The recently paved driveway has been widened allowing parking for 8 cars, in addition to the oversized garage two car garage. The side yard is approximately 3,000 sq/ft and features a highly sought-after wrought-iron courtyard gazebo. The yard is 3/4 fenced in. This space can easily become he wildflower garden of your dreams, the largest vegetable garden in town, or a place to park your RV or boat. Pictures do not do this property justice. Book your appointment today.

38 W Taconic Road, Wappingers Falls

$799,000

4 Beds ⋅ 4 Baths ⋅ 1029249 MLS

Rare opportunity to own this 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 you will notice the 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

$825,000

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

$799,000

5 Beds ⋅ 4 Baths ⋅ 1008407 MLS

Rare opportunity to own this 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 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

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