Pine Plains Homes with Driveway Parking features

Pine Plains Homes with Driveway Parking features

Welcome to Pine Plains, New York – a charming community that blends the tranquility of rural living with the vibrancy of a close-knit town. Nestled in the heart of Dutchess County, Pine Plains is part of a highly regarded school district that prioritizes academic excellence and holistic development. The Pine Plains Central School District is known for its dedicated educators, modern facilities, and a diverse range of extracurricular programs that foster creativity and critical thinking. Families here appreciate the small class sizes, which allow for personalized attention and a supportive learning environment, ensuring that every child has the opportunity to thrive.

In addition to its outstanding educational offerings, Pine Plains boasts an array of beautiful homes that cater to a variety of lifestyles. Many properties in this area feature the convenience of driveway parking, making daily life easier for residents. Imagine coming home to your own driveway, where you can easily park your vehicle and enjoy the peace of mind that comes with having your own space. These homes often blend modern amenities with charming architectural details, creating an inviting atmosphere that feels like home the moment you step inside.

Living in Pine Plains means embracing a lifestyle enriched by nature, community, and educational excellence. Whether you're raising a family or looking for a serene retreat, this picturesque town offers the perfect backdrop for a fulfilling life. Explore the homes available with driveway parking and discover the ideal setting for your next chapter in Pine Plains, NY!

Newest Pine Plains Homes with Driveway Parking features

$525,000
2 Beds ⋅ 2 Baths ⋅ 1031285 MLS
Beautifully renovated home privately set on a scenic, park-like property, offering the perfect blend of privacy and convenience—Located on the Dutchess/Columbia line just 2 minutes to the Taconic State Parkway for an easy commute. This move-in-ready home is filled with natural light and showcases high-end finishes, designer touches, and thoughtful updates throughout. The chef's kitchen features quartz countertops, stainless steel appliances, custom cabinetry with pantry, floating shelves, soaring ceilings, built-in bench seating, an additional wall of cabinetry for exceptional storage, and access to the patio and backyard—ideal for indoor/outdoor living. The lovely living room is highlighted by oversized windows, sliding glass doors leading to a partially covered deck, recessed lighting, and a beautifully remodeled powder room with board-and-batten accents. Upstairs, the primary suite offers vaulted ceilings, oversized windows, and a walk-in closet with custom organizers. The spa-inspired full bath features a double vanity, an oversized luxury walk-in shower, and a stylish barn door entrance. A generously sized second bedroom includes a large closet. Additional features include central air, main-level laundry, recessed lighting, and quality finishes throughout. Outside, enjoy complete privacy surrounded by mature landscaping, established perennial gardens, raised garden beds, a large storage shed, and a separate studio/barn offering endless possibilities for a workshop, art studio, or hobby space (needs work). Conveniently located near state parks, hiking, skiing, and other Hudson Valley recreational opportunities, just 2 mins to the Taconic State Parkway, 20mins to Metro-North. Also nearby are sweet shops, restaurants, wineries, and equestrian estates that define the Hudson Valley lifestyle, this turnkey estate presents a rare opportunity to own an exceptional private retreat where luxury, recreation, and nature exist in perfect harmony.

10 Dickman Farm Road, Red Hook
$445,000
3 Beds ⋅ 2 Baths ⋅ 1029261 MLS
Tucked away off the main road, this property is situated on a private road near Hunns Lake. The former fishing cottage is cozy and quiet on 1.2 acres, with mature trees, lawns and meadows with western sunset views. The entryway leads to a windowed sitting room which opens up to the main pine paneled living room, lined with an oversize picture window with sliders. A stone wood burning fireplace with insert provides a great centerpiece and two cords of wood are ready for next season. Flooring is currently painted with a striping trim. Double pane thermal windows with screens are throughout the house. The open country kitchen has wide plank pine floors and countertops with plenty of cabinet storage. The dining area includes two sets of glass slider doors leading out to the spacious two level Trex redwood decking overlooking the pool. A deluxe propane grill with oven and burner is also included. There is a full bath with double sink and tub with shower in addition the laundry. A one car garage is also on this level. Upstairs is the primary bedroom with multiple window exposures. A brand new full bathroom features a beautiful soaking tub. There are two more bedrooms/office also having two window exposures. Furnace, Oil Tank, Water Heater and Pool Pump are new from 2025. The property on one side and the rear is buffered by wide open land/forest. 50 acre Hunns Lake is nearby, and is a great 2 ½ mile walk around it. This is nearby to the villages of Millbrook, Pine Plains, Rhinebeck, Millerton and more. All provide shopping, dining, and overall country recreation. The Wassaic Metro North train station is just 18 minutes away; all this just two hours from NYC. Welcome to the Hudson Valley!

26 Hunns Lake Place, Stanfordville
$350,000
2 Beds ⋅ 1 Baths ⋅ 1022019 MLS
Welcome HOME to this charming farmhouse cottage, originally built in 1853 and was Schoolhouse number nine, one of clinton's original schoolhouses! Nestled on over an acre of picturesque, level property in the highly sought-after Pine Plains School District, this one-of-a-kind home offers 2 bedrooms, 1.5 bathrooms, and 1,320 square feet of comfortable living space surrounded by mature trees and peaceful countryside. Rich in history and timeless character, the home features hardwood floors, soaring ceilings, oversized windows that fill the home with natural light, and a spacious living room centered around a cozy wood stove with a wet bar. The generously sized country kitchen offers abundant cabinetry, extensive counter space, and a bright dining area overlooking the backyard. The flexible floor plan includes two first-floor bedrooms, a full bathroom, and an additional half bath, providing the convenience of one-level living. A full walk-up attic offers exceptional storage and exciting potential for future expansion. Step outside to the oversized rear deck overlooking the sprawling backyard, ideal for entertaining, gardening, or simply enjoying the tranquil setting. The property also features a detached one-car garage, multiple storage sheds, and an expansive level lawn with plenty of room for recreation, hobbies, or future improvements. Whether you're searching for a full-time residence, a weekend getaway, or a piece of Hudson Valley history, this rare property offers historic charm, endless potential, and an unbeatable location just minutes from Rhinebeck, Millbrook, Pine Plains, wineries, farm markets, hiking trails, and everything the Hudson Valley has to offer. Some photos have been digitally staged.

357 Pumpkin Lane, Clinton Corners
$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
$379,000
3 Beds ⋅ 1 Baths ⋅ 1028565 MLS
Attractive 3 bedroom, 1 bath cape cod loaded with recent improvements. Attractive open floor plan includes kitchen w/stainless appliances, granite counters & breakfast bar, which flows seamlessly to living room w/fireplace. Two first floor bedrooms and tile bathroom. Second floor includes generously sized bedroom plus office/den and storage space. Three season front porch is the perfect place to relax. Recent improvements include roof, furnace, water heater, pressure tank and 200 amp electric service. One car garage plus large workshop/studio space complete with insulation & electric and dedicated driveway. All situated on park-like property just minutes from shopping, dining, Stissing Lake and Taconic State Parkway. Attractively low taxes. An opportunity not to be missed.

2795 Church Street, Pine Plains
$2,500,000
12 Beds ⋅ 7 Baths ⋅ 1025626 MLS
Sisters Hill Farm – A Rare Legacy Estate in the Heart of the Hudson Valley Welcome to Sisters Hill Farm, an extraordinary 66-acre country estate where history, stewardship, and opportunity come together in one exceptional offering. Set amidst rolling fields, mature woodlands, and breathtaking pastoral views, this remarkable property offers a rare opportunity to own one of the region's most iconic farm estates. At the heart of the property stands a magnificent turn-of-the-century farmhouse that captures the elegance and craftsmanship of a bygone era. Rich in architectural detail, the multi-bedroom residence has been lovingly maintained and showcases impressive period character throughout. A grand stone fireplace anchors the home's welcoming living spaces, complemented by stunning handcrafted woodwork and intricate trim. Large windows frame sweeping views of the surrounding farmland, gardens, and mature trees creating a peaceful connection to the landscape in every season. The estate also includes a second four-bedroom residence and a charming one-bedroom cottage, offering exceptional flexibility for extended family, guests, rental income, or staff accommodations. Privately situated, the second home features an in-ground swimming pool, providing a relaxing retreat surrounded by the beauty of the countryside. Supporting the agricultural operation is an impressive working barn thoughtfully designed to meet the needs of a modern CSA farm while preserving its traditional agricultural character. The barn includes comfortable living quarters for farm staff, stalls, extensive storage areas, and a commercial walk-in refrigeration system essential for harvesting, storing, and distributing fresh produce. These facilities provide the infrastructure necessary to continue successful vegetable production immediately upon ownership. Numerous outbuildings throughout the property support equipment storage, maintenance, workshops, and additional agricultural uses. Every element of Sisters Hill Farm has been thoughtfully developed to support both productive farming and exceptional country living. Adding to the property's exceptional value is its established Community Supported Agriculture (CSA) program. The CSA offers a well-established operation with a loyal membership base, modern infrastructure, and a strong reputation for high-quality, sustainably grown produce. The agricultural business provides an opportunity to continue a successful farming enterprise while benefiting from decades of community goodwill. Additional information about the CSA can be found at sistershillfarm.org. Whether envisioned as a private country estate, a multi-generational family compound, a working farm, or an investment in the region's agricultural future, Sisters Hill Farm offers extraordinary versatility and enduring appeal. This is more than a beautiful property—it is a place where history has been carefully preserved, the land has been thoughtfully stewarded, and the possibilities for its next chapter are truly exceptional.

123-179 Sisters Hill Road, Stanfordville
$2,475,000
7 Beds ⋅ 6 Baths ⋅ 1022023 MLS
The History: The wonderfully characterful Hammertown was established in 1774, in a small hamlet of millworkers, farmers, and blacksmiths, amidst the lush pastoral landscapes surrounding what would become the town of Pine Plains, New York. The home and its grounds were occupied by only three families across 250 years, each family slowly developing the property to include, in addition to the sprawling main house, beautiful, sweeping trees and gardens, stone walls, a two-hundred-year-old barn that has housed many an ambitious project, and a sweet guest house nestled at the entrance of the land. The Main House: The seat of the property is a traditional colonial farmhouse, tastefully renovated and beautifully envisioned for the current era - while still respecting the home's history as it passed through a quarter of a millennium. Exquisite millwork lines every wall in the home, no less than five fireplaces are peppered throughout, and we mustn’t forget the beautiful, wide-plank wood floors. On the ground floor, you’ll find a large boot room with plenty of storage, a formal dining room, a cozy living room, a wallpapered powder, and the beating heart of the home - the monumental kitchen; a light-filled and dreamy space perfect for entertaining. The second floor has two large bedroom suites with a full bath each, three additional bedrooms, and another full bath. Each bedroom has a subtle but charming color palette, more extraordinary woodwork, and two of the bedrooms have fireplaces. The proportions of the rooms and the layout are well suited to a large family or those with frequent guests, with the two en suites each occupying their own corner of the house, and the three bedrooms and last bathroom in their own wing. The Grounds: Outside, the farmhouse has two ‘faces’ and two beautiful porches. Additionally, a large dining terrace bordered by stone walls sits conveniently off the kitchen. Strolling away from the main house, you’ll find a wrought-iron greenhouse structure and a French parterre garden planted with herbs, lavender, and flowers. The Barn: The Hammertown barn, built in the early 1800s by the founding family of the property, has lived many exciting lives - from being home to elephants from the Barnum Bailey Circus in the early 1900s to its most recent iteration as the main outpost of a beloved furnishings and antiques brand. The barn’s soaring beams and incredible staircase welcome you into the structure, where multiple rooms serve various purposes - including plenty of living space (the perfect place for a home theater), open, sprawling areas with soaring ceilings ideal for hosting large groups, and an abundance of utility, office, and storage space. The barn is fully serviced with electric, air conditioning and heat, and plumbing (including a bathroom). The Guest House: The two-bedroom, two-bath guest cottage was built to elegantly blend with the property's historic character and features multiple fireplaces and detailed millwork. The double-height great room’s arched window floods the house with warm light, and French doors lead to the cottage’s sweet outdoor terrace. The Surroundings: Hammertown is just minutes from Pine Plains, less than fifteen minutes from Millerton and the Connecticut border, and two hours from New York City. The area is defined by some of the most beautiful country landscapes in the region, and is full of hiking trails, thriving local farms, and wonderful small towns and communities. As a marvelously well-serviced compound, Hammertown has incredible potential for those who also wish to explore live-work opportunities, having been home to multiple tasteful commercial ventures and events over the past several decades.

85 Hammertown Road, Pine Plains
$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
$799,000
3 Beds ⋅ 2 Baths ⋅ 1007119 MLS
A 1949 original, 153 Near Road was fully reimagined in 2021. The house is sited on two acres off a county lane, yet is a short distance to Hudson, Red Hook, Pine Plains with easy access to the Taconic Parkway. The first floor features an open concept, the kitchen, dining and living spaces flow together without interruption, anchored by a kitchen island and warmed by a wood stove. Flooded with natural light through picture windows the light wood floors catch and reflect the sunlight throughout the day. A first floor bedroom suite offers privacy and ease, featuring a stunning walk in shower and a laundry room tucked nearby, everything one needs on one level. Upstairs, two bedrooms feel suspended in the tree canopy. The window above the soaking tub perfectly frames it, making it an ideal spot for a moonlit soak. Enjoy the stream on a hot summer day and later relax under the stars around the firepit. The electrified outbuilding is a great space for an office or artist studio. One won't have to worry about using additional electricity, as the solar panels lighten the footprint.

153 Near Road, Red Hook
$850,000
1008519 MLS
Commercial property with Multi-Use potential in Pine Plains, NY. This versatile commercial property boasts a variety of uses, making it of interest to investors, entrepreneurs and businesses alike. With two apartments, two office spaces, dedicated studio areas and a spacious workshop area with 5 bays with overhead doors. This property offers the perfect blend of residential and commercial functionality with potential for showrooms. Hardwood floors throughout and a new roof. Hard to find commercial property.

2773 Church Street, Pine Plains
$639,000
3 Beds ⋅ 3 Baths ⋅ 1006576 MLS
Your Lakeside Sanctuary Awaits at 553 Lake Rd in Pine Plains NY. Imagine a life where your mornings begin not with an alarm, but with the gentle song of birds and the sun rising over the glassy waters of Twin Island Lake. Welcome to 553 Lake Road in Pine Plains—a home that doesn’t just offer a place to live, but a feeling of profound peace, warmth, and sanctuary. A Home Infused with Warmth and Light From the moment you step inside, you are wrapped in comfort. Gleaming hardwood floors guide you through a thoughtful layout designed to soothe the soul. The Living Room: Unwind by the crackling fireplace while gazing out at beautiful lake views. The Heart of the Home: An updated, sun-lit kitchen boasts abundant countertop and cabinet space, flowing effortlessly into a lovely dining area. The Sunroom: A bright, incredibly spacious sunroom offers the ultimate spot to curl up with a good book, practice yoga, or simply watch the seasons change. Space to Grow, Create, and Breathe The second floor features two beautifully appointed full baths, ensuring ultimate convenience with 3 bedrooms. Downstairs, a full walkout basement bursts with potential, offering the ideal layout to create an accessory dwelling unit (ADU), a guest suite, or rental space. For the creator or hobbyist, the 2-car heated garage is a dream come true, complete with a workshop and a spacious loft perfect for DIY projects or studio space. Peace of mind is also guaranteed with a whole-house generator. Embrace the Great Outdoors Step outside onto your brand-new Trex porch to sip your morning coffee, breathe in the crisp Hudson Valley air, and feel the stress of the week melt away. With over 3 private acres of your own land, you can hike, explore, and connect with nature right in your backyard. Lake access on your private dock just across the street, kayak or canoe around the lake for an interesting adventure. Looking for a challenge? The breathtaking trails of Mt. Stissing are just minutes away. The Location: A Seamless Escape Located under 2 hours from NYC with a straight, scenic drive up the Taconic State Parkway, this property is incredibly versatile. Whether you dream of a permanent full-time haven, a magical summer retreat, or a lucrative short-term rental/Airbnb, this home is ready to fulfill your dreams. Best of all, you are just 15 minutes away from the historic streets, gourmet dining, and culture of Rhinebeck and Red Hook.

553 Lake Road, Pine Plains
$549,000
2 Beds ⋅ 2 Baths ⋅ 1006574 MLS
Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has a proven track record as a highly successful Airbnb. Whether you are looking for a lucrative investment, a dream summer getaway, or a year-round sanctuary, this home has it all. The entire front of the house features stunning, unobstructed lake views. Start your mornings on the covered porch sipping coffee, listening to the birds, and watching the wildlife on the water amidst beautiful perennial flowers. Inside, enjoy a bright, spacious open floor plan ideal for modern living. The layout includes a primary bedroom and bath with plenty of closets, plus a second bedroom and a flexible home office with a large closet, sleeps like a 3 bedroom. Step outside to hike up your own 4 acres of private land, or drive just 15 minutes to enjoy the top-tier restaurants and entertainment in nearby Red Hook and Rhinebeck. All this peace and quiet is located under 2 hours from NYC via the Taconic State Parkway!

559 Lake Road, Pine Plains
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