Pine Plains Homes with Private Parking features

Welcome to Pine Plains, a hidden gem nestled in the heart of Dutchess County, New York. This charming town is known for its picturesque landscapes, friendly community, and a rich tapestry of history that dates back to the early 18th century. With its rolling hills, lush greenery, and serene countryside, Pine Plains offers a tranquil escape from the hustle and bustle of city life, making it the perfect place to call home.

Pine Plains boasts a vibrant local culture, with quaint shops, delicious eateries, and various outdoor recreational activities to enjoy. Whether you’re exploring the scenic trails of the nearby Taconic State Park or attending one of the lively community events, you’ll find that Pine Plains is brimming with opportunities for connection and adventure.

For those considering a move to this idyllic town, you'll be pleased to discover homes that come with the convenience of private parking. In Pine Plains, many properties feature dedicated parking spaces, allowing you to enjoy the peace of mind that comes with secure and accessible parking right at your doorstep. This feature not only enhances your living experience but also adds to the value of your investment.

With a range of charming homes available, from cozy cottages to spacious family residences, Pine Plains offers something for everyone. Embrace the opportunity to live in a community that values both nature and neighborly connections. Discover your dream home in Pine Plains, where comfort meets convenience in a truly enchanting setting.

Newest Pine Plains Homes with Private Parking features

$3,995,000

10 Beds ⋅ 7 Baths ⋅ 953909 MLS

Set far back from one of the Hudson Valley’s most prestigious and scenic roads, this stunningly restored 1830s colonial farmhouse is a masterclass in combining historic charm with sophisticated living. Situated in the heart of the pastoral Shekomeko Valley on just under 10 pristine acres, this property offers ultimate privacy surrounded by large, rolling farms and protected acreage. Classic white clapboard siding and a welcoming front porch set the stage for a home that seamlessly blends 19th-century soul with modern amenities. Step onto original wide-plank flooring and admire the stunning, exposed hand-hewn beams. An oversized living room features a wood-burning fireplace and panoramic views from three exposures, with French doors leading to the expansive property. The formal dining room boasts an additional fireplace and two large china closets. The professionally equipped kitchen includes dual sinks, a premium professional range, a built-in refrigerator, and a sunny, south-facing breakfast room with pastoral views. A convenient butler’s pantry and powder room are also included on this level. Head upstairs to four bedrooms (two with fireplaces) and three bathrooms. The main house includes a fully equipped 3-bedroom apartment with a separate entrance—perfect for guests or staff. The property is a true compound, designed for both entertainment and flexibility. A fully outfitted barn includes a 3-bedroom apartment, a gym with a sauna, laundry, a workshop and a very large storage room which can easily be converting into more living space. Other buildings include another barn/workshop, a yoga studio, a 2-car detached garage with a storage loft, and a 60' equipment shed. This parcel offers endless potential for hobby farming, horses/livestock, or creating a private, quiet home office. Located in the desirable Shekomeko Valley, this property offers a rare mix of secluded tranquility and easy access to nearby towns.

1515-1517 Route 83, Pine Plains

$736,500

938910 MLS

A Distinctive Commercial Opportunity in the Heart of Pine Plains Once a cherished church, this remarkable building has been thoughtfully transformed into a dynamic commercial space—ideal for retail, studio, gallery, or a variety of creative ventures. Positioned right on Main Street among beloved local businesses, it offers unmatched charm and visibility. A grand entrance awaits with wide stone steps and iconic yellow doors that open into a welcoming lobby. From here, explore the soaring main hall, the spacious lower level, or the airy loft. The main floor captivates with its dramatic cathedral ceilings, sweeping open layout, and abundant natural light pouring through oversized windows. Original wide-board hardwood floors lend historic character, while ceiling fans and versatile track lighting enhance comfort and ambiance. The loft overlooks this inspiring space, perfect for display, seating, or additional workspace. Downstairs, the lower level offers generous square footage with tall ceilings and bright natural light from ground-level windows. A built-in bar, worktables, and a convenient half bath make this level highly functional and full of potential. Pine Plains is a thriving hub within the Hudson Valley, drawing both locals and visitors traveling along Route 199 between Connecticut, Dutchess County, and the river towns of Hudson and Kingston. Just two hours from NYC, the area benefits from a strong mix of residents, tourists, and second-home owners—supporting a lively business environment. Endless possibilities await in this one-of-a-kind commercial property. Create your next venture in a space that truly stands apart.

3007 Church Street, Pine Plains

$485,000

4 Beds ⋅ 3 Baths ⋅ 924504 MLS

A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite bath. A second hallway full bath is conveniently located for use by the other two bedrooms. First floor also has guest quarters that include a bedroom, half bath and sitting room or office. Finished basement with a gas fireplace for those chilly winter nights at home with family. An additional room that could be for gaming, office or den. Completing the lower level is a separate room for laundry. There is also a one car garage and an unfinished bonus room waiting for you to make it special to you. Plenty of yard space for outdoor activities and BBQs. Driveway has room for plenty of off-street parking. Quiet road conveniently located near the town park – beach, kayaking, playground, large pavilion, picnic area, etc. A short distance to Thompson Pond Nature Preserve, plenty of hiking trails including a trail up to the Stissing Fire Tower. Less than a mile from village center with its quaint shops and eateries – dine at The Stissing House or get pizza or burgers and don’t forget to visit the Stissing Cultural Center for a concert or a play. Come take a look!

82 Lake Road, Pine Plains

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