Pleasant Valley Homes with Detached Parking features

Welcome to Pleasant Valley, New York – a charming gem nestled in the heart of Dutchess County. This picturesque town is renowned for its stunning natural landscapes, friendly community, and a rich tapestry of history. With its lush parks, serene walking trails, and vibrant local culture, Pleasant Valley offers a delightful blend of suburban tranquility and easy access to the bustling amenities of nearby cities.

One of the standout features of homes in Pleasant Valley is the availability of detached parking. Imagine the convenience of having your vehicles securely parked just steps away from your front door. Detached parking not only provides an added layer of privacy but also complements the spacious layouts of the homes, enhancing the overall appeal for families and individuals alike. Whether you're a busy commuter or someone who enjoys entertaining guests, this feature ensures that your lifestyle is both practical and stylish.

Pleasant Valley is also home to a variety of recreational activities, from hiking in the nearby scenic trails to enjoying community events throughout the year. The town's close-knit atmosphere fosters a sense of belonging, making it a perfect place for families and young professionals. With excellent schools and a plethora of local shops and eateries, everything you need is just around the corner.

If you’re seeking a home that combines comfort, convenience, and community spirit, Pleasant Valley is the perfect destination. Explore the wonderful homes with detached parking features and discover the lifestyle that awaits you in this enchanting town. Your dream home in Pleasant Valley is just a visit away!

Newest Pleasant Valley Homes with Detached Parking features

$495,000

3 Beds ⋅ 2 Baths ⋅ 1006885 MLS

The Ultimate Hudson Valley Retreat: Private Living Meets an Enthusiast’s Dream Escape to your own private, tree-lined sanctuary in Pleasant Valley. Tucked away in the highly desirable Arlington School District, this custom-built, 1.7-story residence offers the perfect blend of country living, efficiency, and unmatched mechanical utility. From the moment you arrive, the towering trees and serene surroundings establish a sense of total privacy. Inside, the home features 3 spacious bedrooms and 2 full baths, framed by striking A-frame commercial-grade windows that flood the main living spaces with beautiful natural light. Designed for total self-sufficiency and year-round comfort, the property features a top-of-the-line Central Boiler E-Classic outdoor wood furnace, which handles the home's heating by efficiently piping heat through the main furnace to control the lower-level baseboard system—allowing you to heat your home using the land's abundant natural timber. The main home also features central air, a central vacuum system, a water purification system, and a peaceful 3-season room perfect for taking in the wooded views. The basement features a walk-out to the lower level, offering plenty of storage. For absolute peace of mind, a premium Generac backup generator protects the property—fully connected to provide uninterrupted power to both the main home and the detached garage. For the car enthusiast, mechanic, hobbyist, or entrepreneur, the crown jewel of this property is the detached, commercial-grade 3-car garage. Fully equipped with a 4-post lift, a dedicated workshop space, and a compressor.. Combined with the attached 2-car garage on the main house, you have sheltered space for 5+ vehicles and endless projects that can continue seamlessly through any storm. Whether you are launching a business, restoring classics, or seeking a private, high-efficiency homestead, 176 Downing Road offers a lifestyle without limits. ***The personal property is being cleared every day so some pictures may be different.

176 Downing Road, Pleasant Valley

$595,000

2 Beds ⋅ 2 Baths ⋅ 995827 MLS

Welcome to Turtle Pond Gully, a delightful property in the Hudson Valley. Enjoy country life in this sweet colonial farmhouse located in the town of Pleasant Valley. This 1930s cottage offers immense charm and is the perfect retreat for weekenders or year-round residents. The light-filled home offers a cozy and comfortable interior with beautiful wood floors. Many original details have been preserved and the home has been updated and is well maintained. It has a wonderful dining room with a pellet stove and a French door to a peering porch and another to a lovely sunroom; a stylish kitchen with tin ceiling; a living room with a French door to an attractive side porch. Many recent improvements, including new metal roof, new siding, and an automatic Generac generator. The grounds, with fine plantings, a pond and stone wall borders, have a lovely park-like feel. There is a detached two car barn style garage with a large game room and woodshop. Centrally located in Dutchess County this is a convenient location, within a mile to the Taconic Parkway, 10 miles to Poughkeepsie train station and only a 12 minute drive to Millbrook.

145 Drake Road, Pleasant Valley

$1,750,000

6 Beds ⋅ 4 Baths ⋅ 886347 MLS

Step back in time without sacrificing modern comforts in this rare, historic brick farmhouse estate, originally built in the 1760s by early settler Sarah Tobias Newcomb. Rich in Revolutionary War-era history, this extraordinary property tells a story few homes can: Sarah famously sent cheese from her dairy to George Washington's encampment nearby. Over the years, the home has flown both British and American flags, bearing witness to centuries of change. Set on approximately 18 serene acres with subdivision potential for three 3.5-acre lots, the estate includes a beautifully restored 6-bedroom, 4-bathroom residence. Carefully updated to preserve its character, the home features original wide-plank hardwood floors, massive Dutch doors with original hardware, six corner Rumford fireplaces, designer lighting, crown molding, and a fully renovated chef’s kitchen with an eat-in area. Enjoy formal and casual living spaces, including a dining room, living room, and family room. Modern upgrades include new central air, central vacuum, and oil heating with an above-ground tank. Additional amenities include a soaking tub, stall shower, and dedicated dressing area. Property taxes have been lowered for the 2025 tax season, offering immediate financial relief—and there is further potential for tax breaks should the new owner choose to start a small farm operation. Outdoors, unwind on the 50-foot veranda overlooking a tranquil pond and rolling pastures. A charming tiny house by a seasonal brook offers extra retreat space, while two large barns serve various purposes—one equipped with horse stalls and a commercial woodworking shop, the other perfect for additional stabling or storage. An outdoor cabana adds another space for relaxation or entertaining. This estate is being sold as-is by motivated sellers who have poured love and care into its restoration. Whether you're an equestrian, a history enthusiast, or a visionary investor, this property offers endless potential—from farming (which may bring additional tax benefits) to development or simply enjoying the luxury of rural elegance.

11 Brown Road, Pleasant Valley

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