Dutchess Homes with Open Parking features

Welcome to Dutchess County, New York—a hidden gem nestled in the picturesque Hudson Valley. Known for its breathtaking landscapes, rich history, and vibrant communities, Dutchess County is a place where modern living meets the charm of small-town life. With its lush parks, scenic river views, and historic sites, residents enjoy a perfect blend of outdoor adventure and cultural experiences. From the quaint streets of Rhinebeck to the bustling vibe of Poughkeepsie, there’s something for everyone in this diverse county.

For homebuyers seeking convenience and comfort, Dutchess County offers a fantastic selection of homes featuring open parking. Imagine coming home to a spacious driveway or dedicated parking area that welcomes you after a long day. Open parking not only enhances accessibility but also provides the freedom to host family gatherings and social events without the hassle of street parking. Whether you’re looking for a charming cottage, a modern family home, or a luxurious estate, you’ll find properties that cater to your lifestyle and parking needs.

In addition to the convenience of open parking, Dutchess County boasts a strong sense of community, top-rated schools, and a variety of recreational activities. Enjoy hiking along the Appalachian Trail, exploring local wineries, or visiting art galleries that showcase the talents of local artists. With its blend of natural beauty and community spirit, Dutchess County is not just a place to live—it's a place to thrive. Discover your dream home with open parking in this enchanting region and experience the best of New York living!

Newest Dutchess Homes with Open Parking features

$425,000

2 Beds ⋅ 2 Baths ⋅ 1029899 MLS

Pride of ownership shines throughout this clean, well-cared-for home. A rare opportunity to own a highly sought-after end-unit townhome in the desirable Round Hill community! Featuring an open-concept layout, this well-maintained home is move-in ready and waiting for its next owner. Step inside to a bright and inviting living room with a cozy fireplace, bay window, and soaring vaulted ceilings that create a spacious, airy feel. Wood cabinetry, stainless steel appliances, and ample countertops in the kitchen flow seamlessly into the dining area, making it ideal for both everyday living and entertaining. Just off the main living space, a versatile office/den opens to a private deck—perfect for working from home, relaxing, or enjoying your morning coffee. Upstairs, you'll find two generously sized bedrooms with ample closet space and a full bathroom. The unfinished lower level offers laundry, storage, and direct access to the attached one-car garage. Recent upgrades include a new boiler and hot water heater. Residents of Round Hill enjoy exceptional community amenities, including a swimming pool, two playgrounds, and a basketball court. Conveniently located for commuters, with easy access to the Taconic State Parkway, I-84, I-87, and Metro-North. Close to restaurants and shops, this home combines comfort, convenience, and an unbeatable location.

22 Hemlock Court, Fishkill

$420,000

6 Beds ⋅ 2 Baths ⋅ 1025819 MLS

Excellent investment opportunity in the City of Poughkeepsie! This vacant two-family property features two spacious 3-bedroom units, providing strong rental income and immediate cash flow for investors. Each apartment offers bright living spaces, large bedrooms, eat-in kitchens, and separate entrances for added privacy and convenience. The property is well maintained with separate utilities, making it an ideal low-maintenance addition to any investment portfolio. Roof 12 years old, Windows 8 Years old, Furnace 5 years old and Water Heater 2 years old. Conveniently located near Metro-North, Vassar College, Marist College, shopping, restaurants, hospitals, and major commuter routes, this property is positioned in a high-demand rental area. Whether you’re looking to expand your portfolio or secure a solid income-producing property, this multi-family home offers excellent long-term potential.

37 Delano Street, Poughkeepsie

$450,000

2 Beds ⋅ 3 Baths ⋅ 1013360 MLS

Welcome to 27 Spruce Ridge Dr in Fishkill! Located in the sought-after Fox Ridge community, this well-maintained 2-bedroom, 2.5-bath townhome offers 1,572 sq ft of comfortable living space. The open layout features vaulted ceilings, a fireplace, an eat-in kitchen, formal dining area, and private decks perfect for relaxing or entertaining. Upstairs, the spacious loft provides flexible space for a home office, guest room, or additional living area. The primary suite includes a large closet and a jacuzzi tub for added comfort. Enjoy community amenities such as a pool, tennis courts, and playground, all conveniently located near shopping, dining, Metro-North, and major commuter routes. A great opportunity to own in one of Fishkill’s most desirable communities!

27 Spruce Ridge Drive, Fishkill

$625,000

3 Beds ⋅ 1 Baths ⋅ 984293 MLS

"Set on 12 generous acres in one of Rhinebeck’s most appealing country settings, this updated property offers space, privacy, and exceptional flexibility just minutes from Rhinebeck Village and the Taconic Parkway. The home features a remodeled kitchen, generous natural light, and inviting living spaces with strong potential for redesign or further customization. Recent upgrades include 200 amp electric service, well pump, boiler, heat pump and oak flooring. A restored barn adds valuable additional space, ideal for a studio, office, guest area, creative workspace, or recreation along a two-car garage with EV charging. With expansive acreage and multiple usable spaces, the property offers the rare opportunity to create a highly personal Hudson Valley retreat whether as a full-time residence, weekend home, or live/work environment. Close to Rhinebeck’s downtown restaurants, shops, cultural destinations, and Amtrak access, this property combines country privacy with convenient access to the best of the Hudson Valley."

461 White Schoolhouse, Rhinebeck

$1,250,000

4 Beds ⋅ 3 Baths ⋅ 967644 MLS

Don't miss this exceptional value in the heart of the Village of Millbrook: a beautifully maintained and thoughtfully updated 3-bedroom, 2-bath home (2,132 sq ft) complemented by a detached 1,750 sq ft two-car garage with an approximately 1,000 sq ft, 1-bedroom, 1-bath guest apartment above, currently generating rental income that pays for the taxes and maintenance for the entire property! Set on 0.21 acres just steps from Millbrook's boutiques, restaurants, galleries, and everyday conveniences, the property offers an increasingly rare combination of village living and income-producing potential. Originally built in 1910, the main residence was extensively renovated in 2002 with new windows, updated heating systems, a new oil tank, and two-zone central air conditioning, blending modern comfort with historic character. The guest apartment was constructedin 2018 and provides excellent flexibility for rental income, guests, or extended family. The private fenced backyard serves as a peaceful retreat, featuring two bluestone patios ideal for outdoor dining, entertaining, or relaxing. Ideally located near highly regarded public and private schools, summer camps, and premier sporting clubs, including the Millbrook Golf & Tennis Club, Tamarack Preserve, and Mashomack Preserve Club. The region is renowned for its equestrian lifestyle, with access to horse shows, fox hunting, riding trails, and top-tier equestrian facilities. Hiking, fly-fishing, polo, and skiing are all nearby. Millbrook's central location provides convenient access to Rhinebeck, Red Hook, Pine Plains, Millerton, Hudson, Litchfield County, and the Berkshires, home to Tanglewood and a wealth of cultural attractions. Just 1¾ hours from Manhattan by car or via Metro-North Railroad, this unique property offers the perfect blend of village convenience, country charm, and income-producing flexibility.

3311 Franklin Avenue, Millbrook

$459,000

2 Beds ⋅ 3 Baths ⋅ 956930 MLS

Exceptional mixed-use investment opportunity in the heart of downtown Poughkeepsie! This well-maintained brick building offers classic character paired with smart, low-maintenance ownership. Situated on a highly visible corner, the property blends residential income with prime commercial potential perfect for investors or owner-operators looking to plant roots in one of the Hudson Valley’s fastest-growing markets. The building is in pristine condition and features two residential units along with a spacious ground-level commercial storefront ready for a new or expanding business. The residential apartments provide steady rental income, while the vacant commercial space opens the door for additional revenue or personal business use. Solid brick construction, efficient systems, and minimal exterior upkeep make this a truly turnkey, low-maintenance asset. Location is everything, and this property delivers. Just minutes from the Metro-North Railroad Poughkeepsie Train Station, commuting to New York City is simple and convenient. Residents and customers alike will love being close to major downtown attractions including the historic Bardavon Opera House, the scenic Walkway Over the Hudson, waterfront dining, breweries, shops, and year-round entertainment. Nearby hotels such as the DoubleTree by Hilton bringing consistent visitor traffic to the area, supporting strong foot flow for local businesses. Downtown Poughkeepsie continues to see revitalization and investment, making this an ideal time to secure a property that offers immediate income, future upside, and long-term stability. Whether you’re expanding your portfolio or launching a new venture, this standout brick building checks every box: location, condition, versatility, and income potential.

292 Mill Street, Poughkeepsie

$775,000

955036 MLS

330 Main Street Poughkeepsie is beautifully restored 4-story mixed-use rowhouse located in Downtown Poughkeepsie, N.Y. The site was rebuilt from top to bottom in 2010/2011, with exterior facade restoration to its original look and interior restoration of hardwood floors with modern amenities like central heating/AC, video security system and kitchen appliances. Building features a vacant open floorplan1,900SF storefront with basement access and three occupied apartments. Each unit is inspected annually and updated as needed. Could be combined with sister building 328 Main Street as a discounted package. IDEAL FOR OWNER-OCCUPIER - SBA ELIGIBLE - OR INVESTOR WITH A TENANT PROSPECT!

330 Main Street, Poughkeepsie

$775,000

954903 MLS

328 Main Street Poughkeepsie is beautifully restored 4-story mixed-use rowhouse located in Downtown Poughkeepsie, N.Y. The site was rebuilt from top to bottom in 2010/2011, with exterior facade restoration to its original look and interior restoration of hardwood floors with modern amenities like central heating/AC, video security system and kitchen appliances. Building features an occupied 1,900SF ground-floor commercial space with basement access and three occupied apartments. Each unit is inspected annually and updated as needed. Could be combined with sister building 330 Main Street as a discounted package.

328 Main Street, Poughkeepsie

$375,000

953399 MLS

LOCATION - LOCATION - BEACON, NY - MONEY MAKING...TEQUILA BAR & RESTAURANT BUSINESS FOR SALE & LEASE OPPORTUNITY. In the heart of Beacon this super established business opportunity with good lease terms. One of Hudson Valley's most established and thriving communities in walking distance to Metro North Train station and a high end real estate community located on the Hudson River with easy access from Newburgh/Beacon Bridge connecting four counties: Putnam, Dutchess, Orange and Ulster. Be part of this landmark city of the Hudson Valley...beautiful town with spacious sidewalks, plenty of parking and full of activities throughout the week...Making this vibrant downtown city a super destination for a good balance of living and business...Spacious establishment approximately 2600' sq. ft. with an 80-seat capacity on one level. Fully equipped with high ceilings, bar serving a vast selection of tequilas and delicious menu items in a lively environment with character. Experienced staff ready to serve the needs of this beautiful town and its visitors. Sale does not include the real property.

328 Main Street, Beacon

$1,290,000

945229 MLS

Property Overview: Mixed-Use Building in Poughkeepsie Prime Location: Main Street, Heart of city of Poughkeepsie's Downtown Business District, a block to Civic Center, Hotel, Bardavon, Restaurants and Bars. Total Size: Approximately 15,000 sq. ft. Building Features: - 5 Levels of Rental Space: Offering a diverse mix of commercial and residential units. - Main Street Entrance: Convenient access for businesses and customers. - Rear Exit: Leads to shared public parking, enhancing accessibility. Parking: Public parking lot shared with local bars, restaurants, office spaces. Commercial Units: 1. Bar/Cafe/Restaurant: 5,000 sq. ft. split across two levels (2,500 sq. ft. each). 2. Office/Shop: 800 sq. ft. with Roof-top access, possible residential conversion. Residential Units: - 3 separate units consisting of: - Studio - 1-Bedroom Apartment - 3-Bedroom Apartment Additional Information: - Restaurant/Bar; under New Management; in preparation to open. - All units occupied. Advance notice is required for tenant showings (48 hours). - Interested buyers are required to provide proof of funds to schedule a tour of the property. - Appointments must be arranged through ShowingTime, must be accompanied. - Please call for more information or to schedule a visit. This property represents a unique opportunity for investors seeking a mixed-use building in a lively urban area with strong foot traffic and nearby amenities.

302-304 Main Street, Poughkeepsie

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.