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

$649,000

5 Beds ⋅ 3 Baths ⋅ 1051399 MLS

Space, privacy, and possibility in the heart of Clinton Corners! Set on approximately 3.3 acres, this expansive two-family home offers nearly 4,000 square feet of living space and an exceptional blend of versatility and Hudson Valley charm. The main residence features 3 bedrooms and 2 bathrooms, with a generous layout that lives larger than most homes. A welcoming formal entry leads into an inviting open-concept living space where the kitchen, dining area, living room, and den flow seamlessly together—perfect for relaxed everyday living and effortless entertaining. Step outside onto the spacious deck for alfresco dining, sunset gatherings, or quiet mornings with coffee. Down the hall, two generously sized bedrooms accompany a private primary suite with its own ensuite bath. The lower level offers an impressive 2-bedroom, 1-bath apartment with a large kitchen and living room, creating an ideal setup for guests, extended family, or rental income. A two-car garage and dedicated workshop space add even more functionality for hobbies, projects, and storage. Outside, a storage shed and expansive green yard provide plenty of room for gardens, a pool, outdoor entertaining, or play. Whether envisioned as a full-time residence, weekend retreat, multi-generational home, or income-producing property, 226 Charwill Drive offers the space and flexibility to create your own Hudson Valley lifestyle. Conveniently located just minutes from the Taconic State Parkway and approximately 90 minutes from NYC, with the villages of Rhinebeck and Millbrook only about 10 minutes away. Enjoy farm-to-table dining, boutique shopping, local farms, vineyards, and the many cultural and historical treasures that make the Hudson Valley such a special place to call home.

226 Charwill Drive, Clinton Corners

$1,650,000

3 Beds ⋅ 4 Baths ⋅ 1049798 MLS

Set on 50 acres of complete privacy, this 1930's Colonial sits alone with sweeping views to the Berkshires. The home offers country living with a Livingroom with a fireplace, Diningroom with French doors opening to a porch. There is a heated sunroom to enjoy the quiet outside. The primary suite includes its own bathroom and a balcony perfect for morning coffee or stargazing. For added space, the third floor has been made into a yoga/workout room, along with an office and a bath. There are additional two bedrooms and 1 1/2 baths. Outside, sits a charming gazebo overlooking a tranquil pond perfect for nature watching. Also, there is a two car garage and an additional barn for a workshop or studio. Some updates are needed.

81 Tinker Hill Road, Pine Plains

$2,800,000

3 Beds ⋅ 4 Baths ⋅ 1047722 MLS

Set on 9.25 acres of open meadow in Milan, 15 Ferris Lane is a to-be-built contemporary country home conceived and designed by APS Designs, a multidisciplinary design studio, and developed by AELO. The residence takes its cues from the familiar forms of the Hudson Valley and reimagines them through a distinctly contemporary lens. A series of interconnected gabled volumes will stretch across the landscape, combining clean geometry, natural materials, and expansive walls of glass with a warmth and restraint that feel entirely at home in the setting. Symmetrical and timeless in character, the design is grounded in a strong sense of place while introducing inventive new elements. The entrance porch evokes the formality and symmetry of an Italian Palladian villa, creating an iconic arrival. Above, it becomes a panoramic terrace accessed from the second floor, offering an elevated connection to the surrounding landscape. At the heart of the house will be a soaring, barn-like great room whose dramatic volume opens to the landscape through oversized windows and doors. The living, dining, and kitchen areas will flow together, with a mezzanine above adding another layer of space and perspective. Three bedrooms will occupy the quieter wings of the house, creating separation between private and communal spaces. At the rear, the principal living areas will open onto an expansive deck and outdoor entertaining area overlooking the pool and surrounding countryside. The residence will comprise approximately 2,550 square feet on the main level, together with a 730-square-foot mezzanine and an attached 576-square-foot two-car garage. The 9.25-acre property begins along a quiet country road and rises through open meadow to an elevated homesite with long views across neighboring farmland and the rolling hills beyond. The house has been carefully positioned to take full advantage of the setting, with its principal living spaces and terraces oriented toward the surrounding countryside. Founded by Antonio Pio Saracino—an Italian designer and artist licensed to practice architecture in Italy—APS Designs is a multidisciplinary studio whose international projects are shaped by a strong sense of place and span the built environment, interior design, furniture, and art. Saracino’s work is represented in the permanent collections of institutions including the Centre Pompidou, the Brooklyn Museum, and the Los Angeles County Museum of Art, and has been exhibited internationally, including at the Venice Biennale. At 15 Ferris Lane, APS Designs has conceived a contemporary country house for AELO that is firmly rooted in the traditional landscape of the Hudson Valley while establishing a distinctive identity of its own. Estimated delivery Spring 2027.

15 Ferris, Red Hook

$695,000

3 Beds ⋅ 2 Baths ⋅ 1047455 MLS

Set among majestic trees with the gentle sound of a creek below, Turkey Hill is a warm and tranquil country home where soaring ceilings, exposed beams and log home character create an inviting sense of place. A large covered front porch sets the tone. It is the kind of spot made for slow mornings with coffee, long summer evenings and rocking chairs, with birdsong in the trees and the creek in the distance. Inside, cathedral ceilings give the main living space a striking sense of volume, while exposed wood beams throughout the home bring warmth and character from room to room. At the heart of the living room, a wood-burning fireplace with a dramatic stone surround creates a natural gathering place, while a propane stove offers another cozy source of warmth. The kitchen pairs the home’s rustic character with a clean, updated feel, including new quartz countertops and direct access to a side deck leading to the fenced backyard and garden. Off the living room, a light-filled sunroom is currently used as a home office and reading nook, with windows framing views of the surrounding landscape and creek. The sunroom also connects directly to the primary suite, creating an easy flow between the spaces. The primary bedroom includes a walk-in closet and its own private full bathroom, all within a warm, wood-clad space with a high, open ceiling. Upstairs, two equally sized bedrooms share a second full bathroom. Between them, a generous open landing overlooks the living room and fireplace below, further enhancing the home’s open and airy feel. The landscape is just as much a part of Turkey Hill as the house itself. Gardens, old stone walls and a lush meadow give the property the feeling of a country home that has settled naturally into its surroundings. A short trail winds through the meadow to the creek, creating a serene destination of its own just beyond the house. The fenced backyard provides a defined space for gardening, pets and play while still feeling connected to the larger landscape. A full, unfinished walkout basement provides generous room for a workshop, storage and hobbies. The heated detached two-car garage offers even more flexibility, with abundant additional space in the upper attic level, and a new whole-house generator provides added peace of mind. For all its privacy and sense of seclusion, Turkey Hill is remarkably connected. The Taconic State Parkway is just minutes away, putting New York City under two hours from home, while Red Hook, Rhinebeck and Tivoli are all within 10-20 minutes. Together, these beloved Hudson Valley towns offer some of the area’s best restaurants, cafes, shops and markets, making Turkey Hill a desirable country retreat with the best of the region close at hand.

1262 Turkey Hill Road, Red Hook

$425,000

3 Beds ⋅ 2 Baths ⋅ 1040822 MLS

Beautifully renovated from top to bottom. This lovely one level ranch is immaculate and the gem you have been looking for. Walk in to your light filled Living Room open to your dining area, this is truly the heart of your home as the Kitchen, Primary Suite and Guest Bedrooms wing all branch off here. To the left we have a large Primary Bedroom with Walk In Closets and a delightful Primary Bath, bright and clean. The Kitchen is conveniently off the Dining Area and offers wonderful stainless steel appliances, loads of cabinet space and a lovely Eat in Area with walls of windows flooding the home with sunlight. Laundry couldn't be easier with connections in place in a tucked off Pantry. Sliders to the handsome back Deck for al fresco entertaining in the Hudson Valley sunshine. Backyard overlooks your wooded oasis to take in the mature Pines and listen to the Birds. Down the hall there are Two Guest Bedrooms and a hall Bathroom with tub. Great Lower level that walks out to a cute side Deck, wood stove here for cost effective heat and cozy nights. Two Car Garage off this level for ease in all weather, all year long. Ample storage in Garage as well. Light, Bright, and new this ones a real rarity. The sweet town of Elizaville is minutes from neighboring Red Hook and Germantown, still undiscovered you'll love spending the summer swimming at Twin Lakes, and dining at Kiki's Diner, and finishing with ice cream and the Farmers Market at Roosters. 90 minutes to NYC, 6 min to the TSP for easy access.

83 Weaver Road, Elizaville

$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

$1,465,000

3 Beds ⋅ 4 Baths ⋅ 1033554 MLS

Mid Century contemporary home with scenic water views, and luxury amenities. Nestled on the banks of the picturesque Roe Jansen Kill, this unique three bedroom mid century home offers an open, flowing floor plan perfect for modern living. The spacious great room features a custom kitchen with a Garland gas stove, New LG Refrigerator, double oven and large pantry Relax by the stone, wood burning fireplace or step out onto the multi level deck overlooking the serene waterway. The main level also includes a great room, spacious bedroom with sliders to the deck, along with a luxury bathroom featuring a walk in steam shower, double sinks and a jacuzzi tub plus a sizeable flex room perfect for additional bedroom. The oversized upper level primary suite boasts a fireplace, radiant heat, sound surround and its own deck with breathtaking views. The ensuite bath is a true retreat with a bidet and triple glazed walk in steam shower, Additional features include a separate two car garage with a spacious one bedroom apartment complete with a high end kitchen,, bath and office. Outdoors enjoy the 20x40 heated in ground pool with new pool cover in (2024) new pool heater (2024) and new pool pump (2023). The convenient pool house offers kitchen with two year old grill top, remodeled bath and changing room. Additional updates include main electrical box, (2025), washer & dryer,(2024) and well pump (2023). Conveniently located near the Taconic Parkway, Rhinebeck, Hudson and Bard College, this property offers both tranquility and easy access to cultural events. Experience the good life in this distinctive offering!

1202 Jackson Corners Road, Red Hook

$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

$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

$359,000

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

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