Pleasant Valley Homes with Parking Lot Parking features

Welcome to Pleasant Valley, New York, a charming hamlet nestled in the heart of Dutchess County. Known for its picturesque landscapes and tight-knit community, Pleasant Valley offers a perfect blend of rural charm and suburban convenience. Just a stone’s throw away from the vibrant city of Poughkeepsie, residents enjoy easy access to shopping, dining, and recreational activities, while still relishing the tranquility that comes with living in a smaller town.

Pleasant Valley is characterized by its beautiful parks, scenic walking trails, and a strong sense of community. The area is rich in history, with quaint buildings and landmarks that tell the story of its past. Families are drawn to Pleasant Valley for its top-rated schools and safe neighborhoods, making it an ideal place to raise children or enjoy retirement.

When it comes to housing, Pleasant Valley boasts a variety of options to suit different lifestyles and budgets. Many homes in the area feature convenient parking lot parking, providing residents with easy access to their vehicles and ensuring that guests have ample space when visiting. Whether you’re looking for a cozy single-family home or a spacious modern townhouse, you’ll find a welcoming community that feels just like home.

Explore Pleasant Valley today and discover the perfect place to call your own, where every day feels like a retreat in this serene slice of Dutchess County. With its friendly atmosphere and beautiful surroundings, it’s no wonder that Pleasant Valley is a sought-after destination for homebuyers. Come and see for yourself why this charming hamlet is the ideal place to settle down!

Newest Pleasant Valley Homes with Parking Lot Parking features

$1,675,000

1028236 MLS

HUGE investment opportunity, 1611 Main St (7 Residential Units) + 1613 Main St (3 Unit Mixed Use) in Pleasant Valley totaling 10 units for sale. Grossing over 200k yearly, this could be a great addition to your portfolio. Location is close to shopping centers, restaurants and entertainment. This property also has more than enough parking for residents and patrons. Income and Expense sheet & additional photos available upon request.

1611 Main Street, Pleasant Valley

$439,999

4 Beds ⋅ 4 Baths ⋅ 1001702 MLS

Priced to sell and delivered completely vacant! This four-family investment opportunity, located at 234 Lakeshore Drive in Pleasant Valley, offers immense value-add potential in a convenient and accessible Dutchess County location. Perfectly positioned for savvy investors, this vacant asset allows you to immediately begin strategic renovations to maximize your rental income and build substantial equity without tenant interruption. The property features private tenant parking alongside individualized outdoor retreats—including a covered front porch for one unit, a lower-level covered patio, and an upper-level terrace/balcony—presenting a rare chance to elevate each unit with its own private, premium living space. The location offers exceptional transit convenience, situated just 2 minutes from U.S. Route 44 and under 7 minutes from the Taconic State Parkway for effortless travel to Westchester County, Albany, and the wider Hudson Valley. The Route 9 corridor, Mid-Hudson Bridge, and Poughkeepsie Metro-North Station—offering direct service to Grand Central Terminal—are all within a quick 15-20 minute drive Tenants will love the lifestyle convenience, with downtown Pleasant Valley’s local shops and dining just moments away. The property boasts unparalleled proximity to top-tier recreation and culture, including Freedom Park, the Walkway Over the Hudson, James Baird State Park, Millbrook Vineyards & Winery, and Mill House Brewing Company. It is also exceptionally well-located for student or faculty rentals, sitting near Vassar College, Marist University, Dutchess Community College, and the Culinary Institute of America. Set within the acclaimed Arlington Central School District and close to major medical and employment hubs, this property is an unbeatable opportunity to secure a strong, reliable opportunity to secure an excellently located-family asset.

234 Lakeshore Drive, Pleasant Valley

$549,000

2 Beds ⋅ 3 Baths ⋅ 1004244 MLS

This is a 2 BR PLUS an additional dedicated office. Circular driveway to an All new renovation in beautiful Gretna Hill wooded neighborhood, elegant farms beyond. Mahogany full glass door entry on to black marble foyer. Spacious living/dining room, mahogany doors and trim. Full glass exterior door to 12' x 18' Japanese cedar deck. Hardwood floors throughout. Natural wood and marble kitchen with artisanal details, huge quartz worktop, new appliances. Large closet on back porch. First floor marble half bath and laundry. Primary bedroom with12' long mahogany closet, in-suite white marble and glass shower bath. Second Carrera marble with tub bathroom next to second bedroom with triple mahogany closet. Office with huge windows. 14' x 4' front porch. Perennial gardens, stone columns, steps, borders and walkway. Cedar siding. New windows. This property is self sustaining with private well and septic, clear south facing roof for possible future solar. Spray foam insulation, new heat pump mini split H&C. Minutes east to the Taconic Parkway, minutes west to Poughkeepsie shopping.

17 Gretna Hill Road, Pleasant Valley

$600,000

966628 MLS

Endless Possibilities Await! This rare property zoned High Density Residential spans 4.63 acres with exceptional road frontage and visibility on Route 44—a prime location for your next investment. The property features a charming 1915 Colonial full of character and potential, ready for restoration. Out back, enjoy a Gunite pool overlooking the serene Wappingers Creek, with over 600 feet of water frontage—a perfect setting for relaxation or future development. In addition to the main house, the property includes: An office building with a 2-bedroom, 2-bath apartment above , currently renting for $1650 and A double-wide home offering additional rental income of $1900 . This property needs a start fresh—tear down or work with what you have and reimagine the site as you wish. Whether you’re looking to invest, develop, or create a live/work space, this property is a blank canvas with incredible potential. Bring your vision and your buyers—this is the opportunity you’ve been waiting for!

1380 Route 44, Pleasant Valley

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.