Pine Plains Homes with Detached Parking features

Welcome to Pine Plains, NY – a charming and picturesque town nestled in the heart of Dutchess County. Known for its scenic landscapes and tight-knit community, Pine Plains offers a delightful blend of rural charm and modern conveniences. One of the town's standout features is its highly regarded school district, which is dedicated to fostering a nurturing and stimulating environment for students. The Pine Plains Central School District prides itself on its commitment to academic excellence, offering a range of programs that cater to diverse learning styles and interests. Parents can feel confident knowing their children are receiving a quality education, supported by dedicated educators and a variety of extracurricular activities.

In addition to its exceptional educational offerings, Pine Plains is also home to a selection of beautiful homes that boast detached parking features. Imagine returning to your spacious abode after a long day, where you can easily park your vehicle in your own dedicated space. These homes provide not only convenience but also an added layer of privacy and security. Whether you’re looking for a cozy cottage or a larger family home, Pine Plains has something to suit every taste and budget.

With its charming downtown area, outdoor recreational opportunities, and a strong sense of community, Pine Plains is the perfect place to call home. Discover the joys of living in this idyllic town, where quality education and comfortable living go hand in hand. Come explore Pine Plains today and see for yourself why this hidden gem in New York is the ideal setting for your next chapter!

Newest Pine Plains Homes with Detached Parking features

$800,000

5 Beds ⋅ 4 Baths ⋅ 1044978 MLS

Looking for a Dutchess County home with acreage, mountain views, guest accommodations, and flexible living space? Set on 5.16 acres in Stanfordville, this one of a kind property offers nearly 2600 square feet of living space along with an expansive outdoor oasis, multiple outbuildings, and separate accommodations currently used as an Airbnb. Inside the 4 bedroom, 2.5 bath main home, a spacious kitchen offers abundant cabinetry, generous counter space, stainless steel appliances, and a large peninsula. Multiple living and dining areas and a dedicated home office provide room to spread out, while a wood-burning stove framed by an exposed brick wall creates a distinctive gathering space with direct access to the expansive back deck. Upstairs you will find 4 spacious bedrooms, including a primary suite with a private bath and balcony. The apartment is above the detached 2 car garage, with a separate exterior entrance, separate utilities and dedicated elevated deck, creating added separation and flexibility for guests. Inside are comfortable living and dining areas, a kitchen with ample cabinetry and counter space, a bath, and bedroom space with generous closet storage. The private deck with pergola provides an additional outdoor sitting area overlooking the surrounding greenery. Currently used for short-term accommodations, this portion of the property may appeal to buyers searching for a home with guest quarters, separate living space, or potential income. Buyers should verify applicable permits, approvals, and requirements for continued short-term rental use. Beyond the home, more than five acres of park-like landscaped and open grounds create an impressive outdoor setting framed by mountain and countryside views. The property features a large multi-level back deck with space for dining, grilling, and entertaining, along with a landscaped fire pit area, backyard irrigation system, a fountain water feature, barn, shed, an additional outbuilding and expansive open lawn areas. The property also has riparian rights on Wappingers Creek and the Buttercup Farm Audubon Sanctuary is next door, adding even more splendor to this nature lover’s paradise. On the more practical side, heating and cooling is well covered, with mini-splits in the main home on the 1st floor that provide AC and heat as well as 8 zones of oil-fired hydronic baseboads. The apartment has mini-split heat and air conditioning in addition to the electric baseboard heat. The leased solar panels at $212/month cover the main house electric usage, owners currently only pay a $48 delivery fee. The accessory apartment is on a separate meter and runs $85-$100/month. A portable generator and transfer switch adds peace of mind. Located in the Pine Plains School District, this property offers an uncommon combination of exquisite property, flexible accommodations, outdoor entertaining space, and 360-degree Hudson Valley scenery.

6725 - 6727 Route 82 Unit #6725, Stanfordville

$450,000

1 Beds ⋅ 1 Baths ⋅ 1036155 MLS

Here is a truly exceptional opportunity to enjoy the peaceful lifestyle that comes with lakefront living. Immerse in the sounds of nature, enjoy the changing seasons, spend warm summer days kayaking on the lake, and relax in a setting that feels like a true departure from the everyday. Welcome to your sweet escape at 31 Lake Shore Drive, a charming cottage with an open floor plan and vaulted ceiling that's well suited for year-round living. The flexible layout allows you to use the home as either a one- or two-bedroom, depending on your needs. Imagine enjoying dinner every evening with the lake as your backdrop or unwinding on the rear deck while taking in the beautiful water views. From morning coffee at sunrise to relaxing evenings by the water, this home offers a peaceful place to create lasting memories with loved ones and friends. You will enjoy the benefit a spacious basement and a detached one-car garage, providing plenty of storage for outdoor equipment, seasonal items, or hobbies. Situated on nearly half an acre with mature trees for an added buffer of privacy, there's ample room for outdoor activities, entertaining, gardening, or simply enjoying the open space. Whether you're looking for a full-time residence or a weekend retreat this oasis offers the comfort, charm, and lifestyle that make lakefront living so special. It all awaits you! Make it yours today. Please do not go on the property without a confirmed appointment. Schedule a tour today.

31 Lake Shore Drive, Pine Plains

$4,480,000

3 Beds ⋅ 4 Baths ⋅ 1028057 MLS

Perfectly positioned atop more than 54 breathtaking acres in the heart of the Hudson Valley, this inviting country retreat offers exceptional privacy and sweeping natural beauty. Thoughtfully designed to embrace its spectacular setting, the home features an open, light-filled floor plan that flows effortlessly between the living and dining spaces, creating an ideal environment for both intimate gatherings and gracious living. Soaring ceilings, expansive windows, and glass doors bathe the interior in natural light while capturing picturesque views of the surrounding landscape throughout the seasons. At the heart of the home, the living room is anchored by a striking stone fireplace, creating a warm and welcoming gathering space. Thoughtfully equipped for year-round comfort and peace of mind, the home also features central air conditioning and a whole-house generator. The main level includes a serene primary suite, offering the ease of single-level living. Upstairs, two additional bedrooms and a full bath provide comfortable accommodations for family and guests, each enjoying peaceful views of the surrounding landscape. The walkout lower level offers exceptional versatility, with ample space for a family room, fitness area, artist’s studio, or home office, along with a spacious laundry area and abundant storage. Outside, the property’s remarkable acreage invites endless exploration. Wander through open meadows to a tranquil stream, observe abundant wildlife, or simply unwind on the expansive deck while taking in the beauty and serenity of the surrounding countryside. Offering the perfect balance of seclusion and convenience, this exceptional property feels worlds away, yet is just a short drive from charming villages, acclaimed dining, cultural attractions, and everyday amenities of Dutchess County. Whether envisioned as a peaceful weekend retreat or a full-time residence, this is Hudson Valley country living at its finest.

53 Market Lane, Clinton Corners

$400,000

3 Beds ⋅ 4 Baths ⋅ 1016273 MLS

A unique opportunity for builders, investors, contractors, or buyers with vision, this distinctive property offers exceptional potential. The existing 3-bedroom home had been extensively renovated and was ready for occupancy before a minor fire resulted in the interior being taken down to the framing. Importantly, the exterior of the home was not affected, providing a valuable head start for restoration and rebuilding. This rare property allows the next owner to complete the renovation and bring the home back to life while benefiting from many of the substantial improvements already made. Adding to its versatility, the property includes a second approved building site for a 1-bedroom cottage, creating flexible options for guest accommodations, a home office, rental income, or a private retreat. Beyond the improvements, the land’s natural beauty further enhances its appeal. Established fruit trees, scenic woodland trails, and striking rock outcroppings create a picturesque setting rich in character and outdoor enjoyment. Whether exploring the woods, harvesting fruit, or simply taking in the peaceful surroundings, the property offers a meaningful connection to nature. An oversized garage provides ample space for vehicles, equipment, storage, hobbies, or workshop use. Whether you’re looking to restore the existing residence, create a multi-building compound, or invest in a property with significant upside, this special parcel provides the ideal foundation to bring your plans to life. Conveniently located with easy access to the Taconic State Parkway and just minutes from the dining, shopping, arts, and cultural attractions of Red Hook, Rhinebeck, and Hudson, it offers an appealing balance of privacy and accessibility. Properties with this combination of restoration potential, additional building capacity, natural beauty, and versatile outbuildings are increasingly rare. Bring your ideas and realize the full promise of this one-of-a-kind property. Buyers to perform their own due diligence regarding approvals, permits, building requirements, and intended uses.

117 Camp Road, Red Hook

$11,250,000

5 Beds ⋅ 6 Baths ⋅ 1020209 MLS

Privately set on 50 acres with sweeping Western views of the Catskill Mountains, this extraordinary Shekomeko estate embodies the very best of Hudson Valley country living. Designed by architect Jimmy Crisp and completed in 2004, the residence offers over 9,684 finished square feet of beautifully crafted living space. A long, tree-lined drive framed by mature red maples leads to the elegant residence, where gracious proportions and refined finishes create a home equally suited to grand entertaining and relaxed everyday living. At its heart is a chef's kitchen that flows seamlessly into the main gathering spaces, while walls of windows frame the surrounding landscape. The second floor is anchored by a luxurious primary suite with a fireplace, private balcony, sitting room, dual walk-in closets, and a spacious spa-like bath. Four additional bedrooms and a private office provide generous accommodations for guests. The lower level offers a gym, Pilates studio, play area, expansive wine cellar, and large laundry room. One of the home's defining features is the remarkable stone wing, built around a dismantled historic barn. Its vaulted beamed ceilings, custom copper railings, and floor-to-ceiling stone fireplace create a dramatic great room that opens directly to the pool. Outside, a beautifully landscaped 75' x 25' pool and spa overlook rolling fields and distant mountain views. A stone terrace with an outdoor fireplace, dining loggia, and fire pit creates exceptional spaces for entertaining, while a vegetable garden, pond, pole barn, and detached two-car garage with a studio and bath above complete the estate. Private, peaceful, and surrounded by extraordinary natural beauty, this exceptional property offers a rare opportunity to experience refined country living.

147 Moadock Road, Millerton

$575,000

3 Beds ⋅ 4 Baths ⋅ 997897 MLS

There are plenty of beautiful homes in the Hudson Valley. Far fewer offer a setting--and a lifestyle--like this. Set directly on the lake in one of the area's premier private communities, this architect-designed contemporary offers beautiful water views from nearly every room, abundant natural light, and something increasingly hard to find: the pleasures of owning a country home without many of the usual responsibilities that come with maintaining one. Designed by architect Steve Haas, the 3-bedroom, 3.5-bath home was created to embrace its waterfront setting. Walls of glass frame the lake throughout the main living spaces, while each bedroom features its own en suite bath, including a first-floor bedroom suite ideal for guests or convenient one-level living. At the heart of the home is a dramatic cathedral-ceiling living room with a wood-burning fireplace, expansive windows, and generous space for entertaining. The adjoining dining area and granite kitchen create an easy, open flow for everyday living and gatherings with friends, all with the lake as a backdrop. The large screened porch overlooking the water may quickly become the favorite room in the house. It's the perfect place for morning coffee, summer dinners, entertaining friends, or simply watching the lake change with the seasons. Just off the kitchen, a private courtyard provides another outdoor space for container gardening, a fire pit, or relaxing outdoors. What truly distinguishes this property is how easy it is to own and enjoy. Swim or kayak on the lake, play tennis or bike along the peaceful, tree-lined private roads or boardwalk. And with the beautifully maintained community pool just moments from the house, it feels almost like having your own pool--without the expense, maintenance, opening, closing, or day-to-day work of actually owning one. That same ease extends to the home itself. The association maintains the landscaping, snow removal, private roads, pool, tennis courts, and common areas, while also assuming responsibility for many exterior maintenance and replacement items that would ordinarily fall to the homeowner. The result is an unusually carefree approach to country living. Instead of spending weekends maintaining acreage, landscaping, clearing snow, caring for a pool, or worrying about exterior upkeep, you can simply arrive and enjoy the lake. For a weekend owner in particular, that's a meaningful difference. Offered fully furnished, the home is truly turnkey and ready to enjoy from day one. And while the setting feels like a genuine escape, it's remarkably accessible. Hudson and its Amtrak station are approximately 25 minutes away, while the Wassaic Metro-North station provides another convenient rail option to and from New York City. Rhinebeck, Pine Plains, the Berkshires, Tanglewood, the Taconic State Parkway, and some of the region's best restaurants, markets, and cultural destinations are all within easy reach. For buyers who want waterfront living without taking on the constant upkeep of a traditional country property, this offers a combination that's increasingly difficult to find: an exceptional lakefront setting, distinctive architecture, beautiful views, and a lifestyle designed to be enjoyed rather than maintained.

322 Arcadia Drive, Ancramdale

$1,495,000

3 Beds ⋅ 3 Baths ⋅ 987176 MLS

Experience this stunning sanctuary where rustic charm meets modern luxury on over 19 meticulously manicured acres of pure magic! This elevated 3-bedroom, 3-bath masterpiece captures your heart the moment you arrive, drawing you toward an expansive wood deck and a stunning screened-in gazebo with a built-in fire-pit - the ultimate "entertainment perch" for soaking in breathtaking, panoramic valley views. Inside, the home glows with natural light, featuring soaring vaulted ceilings, a gourmet chef’s kitchen with high-end appliances, and a primary suite that serves as a true retreat with its own stone fireplace and oversized closet. A newly reconfigured second bedroom with an adjacent study provides the perfect versatile workspace. The lower level adds even more flair with a sleek kitchenette, media room, a full bath and a new third bedroom. The equestrian facilities includes a 4-stall barn, arena, hay barn, and fabulous riding trails, catering to every horse lover's dream. 3-car heated garage and a powerful 45KW generator. This impeccably maintained estate isn't just a home, it is a move-in-ready lifestyle that is utterly magical. Minutes to the villages of Millerton and Pine Plains. 2 hours to NYC.

617 BEAN RIVER Road, Pine Plains

$4,900,000

3 Beds ⋅ 4 Baths ⋅ 956925 MLS

Perched atop 40.9 private acres, this exceptional custom-built estate offers unrivaled privacy and sweeping panoramic views of the Catskill Mountains. Blending timeless craftsmanship with modern luxury, this hilltop retreat embodies refined living in a breathtaking natural setting. Inside, antique teak flooring flows throughout the home, adding warmth and character to every space. The open floor plan features a gracious living room that opens to a library with a fireplace and a full bath, creating an inviting centerpiece for both relaxation and entertaining. At the heart of the home, the eat-in kitchen is both functional and striking, featuring a scullery and a distinctive modern Rumson fireplace. The kitchen opens effortlessly onto a stone terrace and pergola, offering a breathtaking setting for alfresco dining while overlooking beautifully landscaped gardens that evolve with the changing seasons. Adjacent, the formal dining room provides a refined space for hosting memorable gatherings. The lower level includes three bedrooms and four full baths, along with a music salon featuring expansive glass doors that open to a stone terrace with breathtaking panoramic views. Additional amenities include a wet bar, laundry room, and wine cellar, offering both convenience and luxury. A detached two-car garage complements the home’s timeless architecture while adding everyday practicality. Experience the epitome of serenity, artistry, and mountain living in this extraordinary hilltop estate—where every sunset paints a masterpiece across the western sky.

1135 Duell Road, Stanfordville

$3,895,000

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

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