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.
A Distinctive Commercial Opportunity in the Heart of Pine Plains
Once a cherished church, this remarkable building has been thoughtfully transformed into a dynamic commercial space—ideal for retail, studio, gallery, or a variety of creative ventures. Positioned right on Main Street among beloved local businesses, it offers unmatched charm and visibility.
A grand entrance awaits with wide stone steps and iconic yellow doors that open into a welcoming lobby. From here, explore the soaring main hall, the spacious lower level, or the airy loft.
The main floor captivates with its dramatic cathedral ceilings, sweeping open layout, and abundant natural light pouring through oversized windows. Original wide-board hardwood floors lend historic character, while ceiling fans and versatile track lighting enhance comfort and ambiance. The loft overlooks this inspiring space, perfect for display, seating, or additional workspace.
Downstairs, the lower level offers generous square footage with tall ceilings and bright natural light from ground-level windows. A built-in bar, worktables, and a convenient half bath make this level highly functional and full of potential.
Pine Plains is a thriving hub within the Hudson Valley, drawing both locals and visitors traveling along Route 199 between Connecticut, Dutchess County, and the river towns of Hudson and Kingston. Just two hours from NYC, the area benefits from a strong mix of residents, tourists, and second-home owners—supporting a lively business environment.
Endless possibilities await in this one-of-a-kind commercial property. Create your next venture in a space that truly stands apart.
Welcome to this meticulously maintained two-bedroom, one-bath home ideally situated on the outskirts of Main Street in Pine Plains, NY. Light, bright, and thoughtfully appointed, the home features gleaming wood floors throughout the living spaces and bedrooms, creating a warm and inviting atmosphere.
The tiled chef’s kitchen offers abundant counter space and room for a dining table and chairs, making it both practical and welcoming. The tiled full bath features a convenient shower. Both bedrooms are generously sized with gleaming wood floors and ample closet space. A spacious, light-filled foyer with coat closet provides a gracious entry, while the formal dining room offers flexibility as an office, craft room, reading room, or additional gathering space. The spacious living room is filled with natural light and showcases beautiful wood floors.
The full basement provides excellent storage and includes a dedicated laundry area. A rear exterior entrance leads to a covered patio, offering a comfortable spot to relax outdoors. Additional amenities include a detached one-car garage with automatic door opener and a whole-house generator for added peace of mind.
Conveniently located approximately 15 minutes from the Village of Millerton and approximately 20 minutes from the Wassaic Metro-North train station, with easy access to Millbrook, Red Hook, and Rhinebeck. Enjoy the charm of Pine Plains while remaining within convenient reach of the Hudson Valley’s villages, dining, shopping, recreation, and commuter connections.
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.
Come home to the Lake !! Nicely renovated 1 Bedroom Apartment. Heat & Hot Water included in the rent. All new Kitchen & Modern Bathroom with Bluetooth Speaker. Enjoy your favorite music, podcasts or playlists while you shower with the convenience of a built-in Bluetooth speaker. Also has a Den/Office. Includes new dishwasher, new state-of-the-art gas range, new refrigerator & microwave. All new bathroom fixtures and tiled floor. Situated up a hill with a great view of the beautiful Twin Island Lake – some lake rights included. The fishing is excellent! Landlord pays heat, hot water, snow removal, lawn mowing & trash collection. Also includes hook up for washer/dryer, off street parking and circular driveway. Beautiful Stissing Lake Town Park within walking distance boasts a recently renovated swimming beach, picnic area with pavilion, bathrooms, showers, ball fields, boat launch and many other summer activities including a summer camp for children. The quant village offers many amenities including a cultural center where you can enjoy a concert or a play. Dine at the historic Stissing House, Champetre (French cuisine) or several other eateries – breakfast, lunch or dinner. You can hike the Thompson Pond Nature Preserve or up Stissing Mountain to the fire tower for a breathtaking view. Travel & Leisure named Pine Plains one of 12 best small towns in NY to live in 2023. Only 94 miles to NY City – less than 15 miles to Millerton, Rhinebeck, Red Hook, Stanfordville and Ancram. Make your appointment today! Good credit and good references a must! No smoking, No pets, No Exceptions!
A once-in-a-lifetime opportunity to own 1,945 acres of pristine land, with expansive road frontage and multiple contiguous parcels. This estate includes 4 single-family homes, a two-family residence, a large commercial building, and a secluded storage or workshop. The diverse landscape features woodlands, rolling meadows, ponds, streams, and striking homesites surrounded by hedgerows, offering a perfect canvas for development or personal retreat. Located across both the Town of Milan and Town of Pine Plains, this property truly captures the essence of rural luxury.
From its sweeping western views of the Catskills, where the sunsets are nothing short of spectacular, to the tranquil northern vistas and the stunning Taconic range to the northeast, the scenery here is simply unparalleled. Stissing Mountain graces the horizon at every turn, creating a sense of belonging. With a subdivision already in place, the groundwork for future development has been laid, while hundreds of untouched acres await your imagination.
Nestled in the tranquil countryside of Dutchess County, this magnificent property offers easy access to charming towns like Red Hook, Rhinebeck, Millbrook, Pine Plains, Millerton, and Amenia.
Experience this stunning sanctuary where rustic charm meets modern luxury on over 19 meticulously manicured acres of pure magic! This elevated 3-bedroom, 3-bath masterpiece captures your heart the moment you arrive, drawing you toward an expansive wood deck and a stunning screened-in gazebo with a built-in fire-pit – the ultimate “entertainment perch” for soaking in breathtaking, panoramic valley views. Inside, the home glows with natural light, featuring soaring vaulted ceilings, a gourmet chef’s kitchen with high-end appliances, and a primary suite that serves as a true retreat with its own stone fireplace and oversized closet. A newly reconfigured second bedroom with an adjacent study provides the perfect versatile workspace. The lower level adds even more flair with a sleek kitchenette, media room, a full bath and a new third bedroom. The equestrian facilities includes a 4-stall barn, arena, hay barn, and fabulous riding trails, catering to every horse lover’s dream. 3-car heated garage and a powerful 45KW generator. This impeccably maintained estate isn’t just a home, it is a move-in-ready lifestyle that is utterly magical. Minutes to the villages of Millerton and Pine Plains. 2 hours to NYC.
Set on a nicely landscaped and private yard ideal for gardening with .65 acres total (an adjacent building parcel of .72 acre can be purchased for an additional amount). This inviting, well-maintained 3-bedroom, 2-bath ranch offers comfort and has a handicap-accessible interior. Features include a living room with a fireplace, lovely wood floors throughout, and a large basement perfect for a workshop, recreation room, or additional storage. The attached garage is accessible through a large sunroom/breezeway for three-season use. Located within walking distance, only minutes to the town beach on Stissing Lake and recreation area offering swimming, boating, and summer children’s camp. Also nearby is Stissing Mt. with hiking trails and Thompson Pond Bird Sanctuary. Pine Plains is a quaint village in Northern Dutchess County which is presently known for the Stissing Center for Arts and Culture and the Stissing House Restaurant. Move right in with no worries with a new roof and kitchen appliances, and central A/C for those hot summer days.
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.
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.
Looking for a property that offers an opportunity for a homestead lifestyle in the Hudson Valley? Situated in the Town of Pine Plains, this early colonial farmhouse is now offered for sale on 15+ acres. Appointed with wide-plank floors, the main level features sun-lit, well-proportioned rooms. On the second floor, there is a primary bedroom with a dressing room, 3 additional bedrooms, an office, and a full bathroom off the hallway. There is also a walk up attic. Off the rear of the house, there is a workshop and several period barns. The property consists of two parcels; the house and barns on 10 acres plus an additional contiguous 5 acre vacant parcel. The land is lovely, with rolling hills and views of Stissing Mountain. This farm is less than two hours from New York City, convenient to Mashomack Preserve and minutes to the Pine Plains town center where you will find shops and restaurants, including the Stissing House Restaurant as well as the Stissing Center for Arts & Culture. For outdoor adventuring, nearby Stissing Lake and Stissing Mountain Hiking Trails are sure to please. A wonderful property for a new owner to bring back to life.
Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**
Welcome to 16 Ryan Road, a spacious 3-bedroom, 2-bathroom home in the scenic Pine Plains area. Featuring a large kitchen with plenty of workspace, a center island, and a functional layout with generous living areas, this home offers a great foundation for your next project.
The property needs some updating and is ideal for a buyer looking to add their own personal touches and build equity. With a practical floor plan, comfortable bedroom space, and plenty of potential, this could be an excellent opportunity for a first-time buyer, investor, or anyone looking for a fixer-upper in a desirable Hudson Valley setting.
Bring your vision and make this home your own!
Beautiful, quiet neighborhood with park like setting. Lovely three-bedroom home with landscaped front, back and side yards. Spacious living room flows into quaint dining room with stained pine tongue & groove walls & updated country kitchen with backyard walkout access. Whether you’re relaxing in front of the fireplace in the living room or entertaining friends at the backyard fire pit, you will love your new life in beautiful Pine Plains township! Updated kitchen with Farmhouse Sink & Butcher Block counters and shelving. Complete top of the line package of Samsung Wi Fi appliances including Samsung Refrigerator, Stove, Microwave & Washer/Dryer. Hardwood floors throughout. Newer roof and boiler. Brand new finished outdoor shed stays! Short walk to Stissing Pond Rec Beach, ball fields and boat launch. A nature enthusiast’s dream with nearby hiking trails throughout beautiful Stissing Mountain as well as Thompson Pond & Twin Island Lake, all just a few minutes’ walk through quiet back roads. Five-minute walk to shops, restaurants, high school, post office, salons, popular Back Bar Beer Garden and world famous Stissing House! Five-minute drive to Taconic Parkway. Central to Rhinebeck, Red Hook, Millerton, Kingston and Great Barrington. Call today!
