Pine Plains Homes for Sale

Welcome to Pine Plains, New York – a charming community that perfectly blends small-town appeal with a strong commitment to education. Nestled in the picturesque Hudson Valley, Pine Plains boasts a vibrant school district that is dedicated to nurturing the minds of its students. The Pine Plains Central School District is known for its personalized approach to education, offering a range of programs designed to cater to diverse learning styles and interests. From dedicated teachers to modern facilities, families can feel confident that their children are receiving a top-notch education.

The district serves students from pre-kindergarten through high school, ensuring a seamless educational journey. With a focus on academic excellence, extracurricular activities, and community involvement, Pine Plains schools foster a supportive environment where students can thrive both academically and socially. Parents appreciate the close-knit community feel, where teachers and families work together to create a nurturing atmosphere for all students.

For those considering a move to this idyllic area, there are a variety of homes for sale in Pine Plains that cater to different lifestyles and budgets. Whether you’re looking for a cozy cottage, a spacious family home, or a charming farmhouse, Pine Plains has something to offer everyone. With its stunning natural surroundings, friendly neighbors, and a strong sense of community, Pine Plains is not just a place to live; it’s a place to grow and flourish.

Explore the homes for sale in Pine Plains today and discover the perfect backdrop for your family’s next chapter!

Newest Pine Plains Homes for Sale

$649,000

5 Beds ⋅ 3 Baths ⋅ 1049359 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

$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

$499,000

2 Beds ⋅ 2 Baths ⋅ 1049475 MLS

Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has it all, lake and mountain views! 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

$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

$895,000

2 Beds ⋅ 1 Baths ⋅ 1045934 MLS

Tucked away on 18+ acres off a designated scenic road sits this bright and charming country cottage. A long driveway leads to the cottage offering complete privacy with mature trees, wildlife, stone walls and a seasonal pond. This home has just undergone a total exterior renovation including new Marvin windows, Hardie Board siding, and insulation. Inside you will find polished concrete floors with radiant heat creating warmth throughout, custom cabinets and black walnut countertops, a Harman pellet stove, and separate wood burning fireplace. Comfortably live on the first floor with its cozy bedroom adjoining the European style bathroom with a vintage, cast iron clawfoot tub. The lofty and serene upstairs is currently configured as one spacious room but can easily be converted to two bedrooms with a bath. The cottage offers the flexibility to serve as a charming guest house should a future main residence be built. Immerse yourself in the peace and natural beauty of this rare property, with trails winding throughout the surrounding woodlands. A quick drive to the village of Stanfordville, and close to Millbrook, Pine Plains, and Rhinebeck. Two hours from Manhattan.

8 Old North Anson Way, Stanfordville

$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

$525,000

3 Beds ⋅ 2 Baths ⋅ 1046543 MLS

Charming Cape Cod Retreat on Nearly 6 Acres in Pine Plains. Tucked away on a quiet country road just outside the village of Pine Plains, this charming three-bedroom, two-bath Cape Cod offers the perfect blend of country tranquility, comfortable living, and endless possibilities on nearly six beautiful acres. Welcoming you home with its cheerful yellow exterior, the spacious main level features a comfortable living room, dining area, kitchen, and convenient three-quarter bath. Upstairs, you’ll find three bedrooms and a second full bath, providing plenty of room for family and guests. The walkout basement offers excellent potential and could easily become a creative studio, workshop, hobby space, home gym, or additional living area. A one-car garage with storage below adds even more practicality and space. Step outside onto the generous rear deck and take in the peaceful surroundings. The home is privately set back from the road among mature trees and a shady lawn, while the wooded portion of the property offers something truly special: two streams that converge on the property, creating a picturesque natural setting. Behind the house is a large, sunny open area with plenty of room for gardening, outdoor games, entertaining, or simply enjoying the beauty and privacy of your own country retreat. The location is equally appealing. You’re close to local farms, restaurants, galleries, and music venues, with numerous hiking, biking, and outdoor recreation opportunities within an easy drive. Nearby Millerton, Rhinebeck, and other Hudson Valley destinations offer even more shopping, dining, and entertainment. Located less than a two-hour drive from Manhattan and a short 20 minute drive to the nearest Metro north train station, this property is ideally suited as a peaceful weekend getaway, vacation retreat, or full-time country home. With nearly six acres, beautiful natural features, flexible living space, and a wonderful Hudson Valley location, this is a rare opportunity to create your own private escape in Pine Plains.

404 Schultz Hill Road, Pine Plains

$695,000

3 Beds ⋅ 2 Baths ⋅ 1042095 MLS

Presenting Hunns Lake House, an inviting country home set along the shores of Hunns Lake, a private residential lake tucked into the countryside of Stanfordville. The property features 150 feet of lakefront and beautiful water views from nearly every room, including a striking glass-enclosed dining room that looks out over the lake. With no motorboats permitted, lake life here is truly irresistible. Enjoy morning swims, afternoons kayaking or paddleboarding, and long evenings watching the light move across the water. Built in 1960, the three-bedroom, two-bath home offers an expansive 3,688 square feet, all on one level. Generous rooms and abundant windows fill the house with natural light. The glass-enclosed dining room opens directly into the living room, where a beautiful stone fireplace brings warmth and character. The large country kitchen centers around an island with plenty of room to cook and gather, while an incredibly spacious family room with a wood stove offers another place to settle in, spread out, and spend time together. The water is a constant presence here. It’s beautiful in every season, from long summer days spent swimming and paddling to crisp fall mornings and snowy winter views from beside the fire. Conveniently located between Millbrook and Rhinebeck, with the hamlets of Stanfordville and Pine Plains just minutes away and New York City less than two hours away, Hunns Lake House is a wonderfully relaxed place to escape to, and an even better place to call home.

119 W Hunns Lake Road, Stanfordville

$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

$379,900

3 Beds ⋅ 2 Baths ⋅ 1035814 MLS

Your dream of owning a charming lake house is within reach. Whether you are looking for a weekend getaway or a year-round home, this home in Twin Lakes is it. Weathered wood fencing frames the driveway entrance. A tasteful row of manicured hedges runs along the entire front yard. Mature trees and lovely plantings welcome you. As you step inside, you are greeted into a cozy living room. A captivating brick wall is home to a recessed wood stove which warms the entire home. The living room opens into a retro, adorable, efficient kitchen. There is a surprisingly large family room just a couple of steps away from the kitchen. What a great space for entertaining, watching TV and relaxing. This room includes the laundry area and access to the backyard. The primary bedroom is extremely spacious, offers a full ensuite bath and lots of closet space. There are two additional bedrooms and another full bath. The outdoor space is great. Both the front and back yards are large and level. The back yard includes a huge storage shed, perfect for storing equipment and all the toys needed to thoroughly enjoy the active lifestyle of a lake community. Relax in the yard or on the cute front porch or maybe take a stroll down to the lake where you can swim, fish or go boating. Host an event or picnic under the lovely pavilion. Come enjoy your slice of paradise. Located a short drive from Red Hook, Hudson and all that the fabulous Hudson Valley has to offer.

8 Loyola 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

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