Pine Plains Homes with Garage Parking features

Welcome to Pine Plains, NY – a charming community nestled in the heart of Dutchess County that combines the tranquility of rural living with the vibrancy of a tight-knit town. Known for its picturesque landscapes and friendly atmosphere, Pine Plains is not only an ideal place to call home but also a community that values quality education. The Pine Plains Central School District is dedicated to providing students with a comprehensive and enriching educational experience. With a commitment to academic excellence, the district offers a variety of programs designed to meet the diverse needs of its students, including advanced placement courses, extracurricular activities, and a strong emphasis on the arts and athletics.

As you explore the real estate options in Pine Plains, you'll discover a selection of homes that perfectly cater to modern living, including properties with convenient garage parking. Imagine coming home after a long day to a beautiful house that not only offers comfort but also the practicality of a garage. Whether you're parking your car or utilizing the space for extra storage, homes with garage parking provide the perfect blend of functionality and convenience.

In Pine Plains, you can enjoy the best of both worlds: a serene environment with easy access to educational opportunities and a range of housing options that accommodate your lifestyle. With its welcoming community spirit and commitment to education, Pine Plains is a place where families can thrive and create lasting memories. Come and discover the charm of Pine Plains – your dream home awaits!

Newest Pine Plains Homes with Garage Parking features

$1,200,000

3 Beds ⋅ 3 Baths ⋅ 1020922 MLS

Perched high on 5.32 private acres with breathtaking, distant panoramic views of the Taconic Range and Berkshire Mountains, this contemporary home has been completely transformed by a top-to-bottom renovation. Seamlessly blending chic modern upgrades with dramatic architectural bones, this turn-key residence offers utmost privacy on a scenic country lane, yet still provides incredible convenience; located just minutes from the Taconic State Parkway, less than 10 minutes to Pine Plains, and a 20-minute drive in either direction to Rhinebeck and Millerton. Spanning nearly 3,000 square feet, the residence unfolds across a light-filled, open-concept floor plan designed to celebrate its extraordinary setting. The dramatic great room serves as the heart of the home, anchored by soaring vaulted ceilings, a floor-to-ceiling exposed brick feature wall, and a wood-burning stove. Expansive walls of glass frame the surrounding landscape and open seamlessly to a generous entertaining deck, creating a natural extension of the living space and capturing breathtaking mountain views in every season. The beautifully appointed kitchen combines timeless design with modern functionality, featuring custom shaker cabinetry, a substantial center island, quartz countertops, and stainless-steel appliances. Adjacent living and dining spaces flow effortlessly, creating an ideal environment for both intimate gatherings and larger-scale entertaining. The main level is anchored by a private primary suite with a walk-in closet and direct access to the deck, offering a serene connection to the surrounding landscape. A dedicated office, laundry and pantry room, and powder room complete the floor. Upstairs, two additional bedrooms, a flex space, and two renovated baths are arranged around a dramatic overlook to the great room below, while a secret bonus space offers endless possibilities as a fitness studio, media room, playroom, or additional office. Beyond the cosmetic artistry, the property features a comprehensive utility overhaul engineered for modern reliability and comfort. The home's infrastructure is anchored by a high-efficiency dual-zone Carrier climate control system with central air and heat pumps, an energy-saving ventilation system, and a robust 200-amp electrical setup backed by a 20KW Kohler standby generator. Pristine water quality is guaranteed by a multi-stage filtration system including UV purification and advanced reverse osmosis lines, while a smart home network of eero mesh Wi-Fi, hardwired Cat 6 connections, Ring cameras, and Nest smart detectors delivers ultimate peace of mind. A rare offering that combines contemporary design, turnkey condition, and spectacular Hudson Valley views, 572 Hicks Hill Road presents an opportunity to enjoy elevated country living in one of the region's most desirable locations.

572 Hicks Hill Road, Stanfordville

$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

$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

$565,000

2 Beds ⋅ 2 Baths ⋅ 1017861 MLS

2-4 Lot Subdivision, includes secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on 7+acres in Hamlet zone (possible subdivision into 2 lots) Plus adjoining 8 acre parcel. Adjoining 4 acre boha parcel can be added for $125,000. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Easy to show with notice.

618 Bean River Road, Millerton

$1,695,000

3 Beds ⋅ 3 Baths ⋅ 1010636 MLS

Privately set on 32 extraordinary acres in the heart of Shekomeko, this light-filled country retreat captures sweeping views of Stissing Mountain and the Catskills from nearly every vantage point. A long drive winds through the landscape to a thoughtfully sited three-bedroom, two and a half bath residence featuring vaulted ceilings, expansive windows, a wood stove, and exceptional southern, western, and northern exposures. The 2,250-square-foot home includes a large porch, an outdoor shower, and an attached two-car garage, offering comfortable living amid complete tranquility. Equally compelling is the land itself—an exceptional setting for recreation, privacy, and even a future build for a larger main residence while retaining the existing home as a guest residence. A rare opportunity to own one of Shekomeko's most scenic properties, where dramatic views, acreage, and endless potential converge. 1504 Route 83 is conveniently located; minutes to Mashomack, 10 minutes to Pine Plains and Millerton, and 20 minutes to Millbrook.

1504 Route 83, 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

$1,275,000

3 Beds ⋅ 3 Baths ⋅ 987704 MLS

A very special living and investment opportunity. Create an exceptional lifestyle in this well-preserved 1968 brick mid-century modern 3,670 sq ft one-level residence, complete with all comforts and amenities. Boasting a unique additional 2,152 sq ft attached indoor pool with floor-to-ceiling bay windows, enjoy sweeping jetliner views spanning more than 30 unencumbered miles of rolling hills to the south. Thoughtfully designed with seamless indoor-outdoor circulation and plenty of storage space, this home feels fitting for one or many. It magically transforms from a quiet writer's retreat into a vibrant family home or your private entertainment hub. Solidly built atop a hill, the easy-access bungalow-style layout features 3 bedrooms and 2 bathrooms on one side, and generous communal spaces on the other--including a living room, an open kitchen with dining area, and a large sunny room ideal for use as an office or additional living space. The island kitchen showcases custom-built original Quaker Maid maple cabinets paired with a state-of-the-art pantry. The original mid-century modern carefully preserved design contributes to the home's authentic historical charm while modern conveniences such as central air conditioning, high-speed internet, and a multi-point alarm system provide comfort. The large 1,800 sq ft heated basement includes a second kitchen area with double sink, countertops and cabinets, a full bathroom, laundry, utility room, and ample storage, ready to become a recreational space when adding a ping-pong table, a pool table and a movie screening area. An attached garage with additional workshop gives direct interior access to the house through a mudroom featuring bluestone floors and cedar walls. Swim year-round in the heated indoor kidney-shaped pool equipped with saltwater system & dedicated propane furnace; the solid brick construction includes a newer roof, massive industrial beams & renovated hardwood ceiling. Vinyl liner was recently replaced. Huge yoga deck facing the view. Property has two wells: one for the main house and a second dedicated to the pool and the garden's automatic irrigation system. The fenced vegetable garden sits just steps from the kitchen. Other practical touches include an automatic generator, outdoor spigots, & exterior outlets. The blacktop driveway makes snow removal quick and easy, while the parking area easily accommodates eight vehicles for pool parties or BBQs. Thanks to the elevated location, cell phone reception is strong. In-ground power lines enhance the elegance of the park-like setting, with its maintained lawn and mature trees offering plenty of outdoor space to roam after your daily swim. The house and grounds are easy to maintain. Use the large detached powered shed for lawn equipment storage, or convert it into a studio. Adding to the property's versatility, the 4.23 acres are already subdivided into two parcels with separate tax bills: the upper 2.23-acre parcel includes the residence while the lower 2-acre parcel is currently zoned as residential vacant land. This property has a renewable two-year Short-Term Rental (STR) permit and is currently operated successfully as an STR for half the year. The property also offers tremendous solar potential. Conveniently located less than a mile from the Taconic State Parkway (yet you cannot hear it), and only a 1hr 45mn drive from New York City, this peaceful and secluded residence makes the perfect weekend or vacation home. Pick up your guests or park at the Rhinecliff or Poughkeepsie train stations - respectively 30mn & 25mn away - or enjoy a scenic 1 hr 50 mn train ride along the Hudson River to the city. Own your own hill with million-dollar views, enjoy it as a primary luxury residence, a seasonal work-from-home getaway, or generate income with this turn-key piece of paradise. Included adjacent parcel address is 68 Ridge Rd Parcel ID 1352006569128825380000.

68-78 Ridge Road, Clinton Corners

$1,425,000

3 Beds ⋅ 3 Baths ⋅ 996917 MLS

**TO BE BUILT** – This custom 3-bedroom, 2.5-bath Farmhouse Ranch seamlessly blends timeless charm with modern design, offering nearly 2,600 SQFT of thoughtfully designed living space. Privately set on 6 acres following a long meandering driveway and tucked far back off the road, this property offers the perfect balance of privacy and convenience in the heart of Clinton Corners. Upon arrival, you’re welcomed by a charming wrap-around rocking chair front porch, while a deep rear porch extends the living space outdoors—perfect for relaxing or entertaining. Inside, the open-concept layout effortlessly connects the vaulted living room, kitchen, and dining area, creating a spacious and airy atmosphere centered around a cozy gas fireplace. A formal dining room and dedicated home office provide added flexibility for entertaining or working from home. The thoughtfully designed split-bedroom floor plan ensures privacy, with the primary suite tucked away in its own quiet corner of the home. This inviting retreat features a vaulted ceiling, an en suite bath, and an oversized walk-in closet. Two additional bedrooms are situated on the opposite side of the home and share a full bath. Above the garage, a spacious bonus room offers endless possibilities for a media room, playroom, guest quarters, or additional flex space. High-efficiency Bosch electric forced-air heating and cooling make maintaining comfort effortless year-round. Generous builder specifications include oak flooring throughout the common areas and granite/quartz countertops throughout. This is a rare opportunity to build a custom home in a peaceful, scenic setting—crafted for modern living while capturing the timeless appeal of a classic farmhouse. Reach out today! **PHOTOS ARE RENDERINGS OF A SIMILAR MODEL BUILT WITH OPTIONS. BUILDER CAN BUILD TO SUIT AS WELL.

114 Quarfelt Road, Clinton Corners

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