Pine Plains NY Real Estate & Homes for Sale

Imagine the perfect getaway, nestled in the heart of Pine Plains, surrounded by the tranquil beauty of nature and wildlife. This once-in-a-lifetime opportunity presents itself as a chance to purchase 30.78 acres on Stissing Lake, offering you your very own private peninsula. With breathtaking water views and stunning vistas in every season, this parcel of land is truly a gem waiting to be discovered. The bucolic setting of this property provides an idyllic backdrop for your dream home. Whether you envision a grand and spectacular residence or cozy and charming tiny cottages, this expansive land can accommodate your vision. The possibilities are endless, and you have the freedom to design and create your ideal living space. One of the standout features of this property is the ability to craft your own private beach area. Imagine stepping out of your home and feeling the sand between your toes as you relax by the water's edge. With a dock exclusively reserved for non-motorized crafts, you can peacefully explore the serene waters of Stissing Lake at your leisure. This ensures a tranquil and undisturbed environment, where you can fully embrace the beauty of your surroundings. As you explore this unique and diverse landscape, you'll be treated to an array of natural wonders. From the vibrant colors of autumn to the glistening white snow in winter, each season brings its own charm and beauty. Wildlife abounds in this area, providing ample opportunities for bird watching, hiking, and immersing yourself in the great outdoors. Not only is this property a haven for nature enthusiasts, but it also offers a sense of exclusivity. Being the last large parcel available for purchase in the area, you'll have the privilege of owning a truly one-of-a-kind piece of land. The privacy and seclusion that comes with this property will allow you to escape the hustle and bustle of everyday life and find solace in the tranquility of your own private retreat. With spectacular water views, a bucolic setting, and the ability to build your dream home or tiny cottages, this property is truly a blank canvas awaiting your artistic touch. Embrace the beauty of nature, wildlife, and the changing seasons, and relish the serene atmosphere that comes with owning your own private peninsula. Don't miss out on this extraordinary opportunity to make your dreams a reality.

Imagine the perfect getaway, nestled in the heart of Pine Plains, surrounded by the tranquil beauty of nature and wildlife. This once-in-a-lifetime opportunity presents itself as a chance to purchase 30.78 acres on Stissing Lake, offering you your very own private peninsula. With breathtaking water views and stunning vistas in every season, this parcel of land is truly a gem waiting to be discovered. The bucolic setting of this property provides an idyllic backdrop for your dream home. Whether you envision a grand and spectacular residence or cozy and charming tiny cottages, this expansive land can accommodate your vision. The possibilities are endless, and you have the freedom to design and create your ideal living space. One of the standout features of this property is the ability to craft your own private beach area. Imagine stepping out of your home and feeling the sand between your toes as you relax by the water's edge. With a dock exclusively reserved for non-motorized crafts, you can peacefully explore the serene waters of Stissing Lake at your leisure. This ensures a tranquil and undisturbed environment, where you can fully embrace the beauty of your surroundings. As you explore this unique and diverse landscape, you'll be treated to an array of natural wonders. From the vibrant colors of autumn to the glistening white snow in winter, each season brings its own charm and beauty. Wildlife abounds in this area, providing ample opportunities for bird watching, hiking, and immersing yourself in the great outdoors. Not only is this property a haven for nature enthusiasts, but it also offers a sense of exclusivity. Being the last large parcel available for purchase in the area, you'll have the privilege of owning a truly one-of-a-kind piece of land. The privacy and seclusion that comes with this property will allow you to escape the hustle and bustle of everyday life and find solace in the tranquility of your own private retreat. With spectacular water views, a bucolic setting, and the ability to build your dream home or tiny cottages, this property is truly a blank canvas awaiting your artistic touch. Embrace the beauty of nature, wildlife, and the changing seasons, and relish the serene atmosphere that comes with owning your own private peninsula. Don't miss out on this extraordinary opportunity to make your dreams a reality.

Enjoy one level living in this cute ranch on a nice corner, quiet lot. Beautiful landscape. Fantastic opportunity to live in the picturesque village of Pine Plains. Walk to Stissing Lake and the Thompson Nature Preserve. Near all the amenities. Excellent starter or retirement home, freshly painted throughout. Nice level yard for a garden, family, pets and entertaining! Walk to library, community center, shops, restaurants, post office, and recreational areas and trails. An outdoor enthusiast's heaven! Come enjoy the lovely landscape, mountains, lakes and neighbors of Pine Plains! You will be impressed.

Fly into this private, hilltop country estate with its own airstrip. This five bedroom, five and one half bath home has stunning bucolic views to Stissing Mountain and provides a layout that has an airy and elegant ambiance. The cathedral living room is centered around a soaring stone fireplace and leads to a cozy library and the formal dining room. Top of the line appliances, marble countertops, and a large butcher block clad island create the perfect chef's space. French doors from the eat-in kitchen and family room lead to a terrace with fireplace and Argentinian grill for al fresco dining. Upstairs, is the primary suite with balcony overlooking Stissing Mountain. An additional four bedrooms and three full baths are also on the second floor. The lower level offers laundry, an office and a full bath. Adding to the allure of this property is a 20' x 45' heated, gunite pool with a guest/pool house and a Har-tru tennis court. The guest/pool house features an additional loft bedroom, bath, kitchen and a gym with sauna. A fully stocked pond, garden and beautiful grounds on the 28.5 acres makes this the ideal place to unwind and enjoy the solitude of this property. Located just minutes to the quaint town of Pine Plains.

Come home to your lake front apartment !! Beautiful, unobstructed, year- round views of Twin Island Lake directly in front of the house. This 3- bedroom apartment with 2 full baths was fully renovated in 2022. All Updated Kitchen. New lighting fixtures throughout. Kitchen has new quartz stone counter tops, new dishwasher and microwave, nice stove & refrigerator. Bathrooms both have new fixtures and new ceramic tile. Large attic space to store all your extras. Separate entrance Nice back yard - plenty of room for swings for the kids. Situated up a hill with a great view of the beautiful Twin Lakes - 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!

Come Home To The Lake!! Beautiful, unobstructed, year-round views of Twin Island Lake directly in front of the apartment. Newly remodeled 1 Bedroom Apartment. Also has a Den/Office. All New Kitchen & Bath. Includes dishwasher, new state-of-the art gas range, new refrigerator and microwave. All new bathroom fixtures and tiled floor. Situated up a hill with a great view of the beautiful Twin Lakes - 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, Separate entrance, Outdoor space, 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!

Beautifully designed custom built 3 bedroom 2.5 bath home with pastoral views is reminiscent of a converted barn with modern amenities. This spacious home built in 2003 is full of special features and little details throughout its flowing design. A sizable custom kitchen presides in the center of the home and is any cook's dream, with large windows offering natural light and panoramic views as a backdrop and highlighting the antique beams in the cathedral ceilings throughout the home. Massive barn doors, hardwood floors, bonus loft space and built ins add to the home's unique touches. Making this even more desirable is the home's expansive first floor garage and workshop boasting room for 3+ cars and extra tall ceilings, allowing for the space to be outfitted for any enthusiast's needs and wants. With upgraded electrical capacity and radiant heating system, this property has plenty of opportunity for additional customizations. Sitting atop a lovely 2 acres parcel, this property is just minutes from the charming and historic hamlet of Pine Plains and area attractions. With so much to offer, you will not want to miss your chance to experience this property.

Contemporary farmhouse offers seasonal views of Stissing Pond. This 2023 residence offers 3280 fin. s.f. on 2.39 acres (2 parcels). Main level offers chef's EIK with Subzero; Thermador ovens, cooktop and DW; CaLefort wine cooler; and quartz counters and backsplash. Pantry has addtl. double drawer frig. DR has built-in oak server. The LR features 20' ceilings with fpl., oak hearth and opens to rear porch. Primary suite offers BR with tray ceiling; bath has soaker tub, glassed-in walk-in shower, privacy tinted window treatments, and heated floors. There is a WIC with W/D. Upper level has 3 BRs, 2 BAs, media room, office/gym, second laundry area and bonus room. Lower level is ideal for storage/mechanicals. There is a 2-car att. garage w/ EV charger. The residence is sited on one of 2 lots with BOHA vacant lot ideal for a studio/guest house and pool. Min. to center of Pine Plains with world class Stissing House restaurant, 10 min. to the TSP and about 20 min. to Rhinebeck/Red Hook.

The approach to this spectacular contemporary barn-style home takes you up a long, winding private driveway past open fields & woods that are part of this special 22+ acre property. At the top of the hill, sits this incredibly private, recently completed, custom, stick built, 3-bedroom, 3.5-bath, contemporary home boasting approximately 4,000 sf of total square footage. This stunning home is designed to take advantage of its exquisite surroundings and to be one with nature with lots of windows, an open floor plan, and soaring high ceilings. Features include a standing seam roof, a lovely in-ground gunite pool, 9' engineered European oak flooring, a fabulous loft office/den, custom cabinetry and vanities, bedrooms with baths en suite, beautiful tiling, a contemporary propane fireplace, high-end appliances and a full basement, the perfect place for a gym/media room/family room/ playroom. Through the trees that surround the home, you can see glimpses of the mountains and pastoral farmland, and with some clearing, the views would be truly unparalleled. Conveniently located in New York's scenic Hudson Valley, just 6 minutes to Millerton & Pine Plains, 20 minutes to Rhinebeck, Red Hook & Millbrook and under 2 hours to NYC. Additional options at additional cost include bluestone patio, decking, garage and much more. Agricultural exemption ensures ongoing tax advantages! A truly stunning and unique, must-see private property (not in a development).

Beautifully updated modern ranch house for rent near town center of Pine Plains, set back on quiet side street, within walking distance to Peck's Market and Stissing Lake Park . The interior is bright and open with refinished solid oak floors throughout, brand new shaker/quartz/stainless kitchen, white subway tile bathroom w/ Kohler cast iron tub, high-performance windows and doors and state of the art HVAC. Each of the 2 bedrooms are located in the rear corners of the house with 2 windows each and a good amount of closet space. Washer and dryer are included and located in the unfinished walk-out basement level. Expansive yard with enchanting large patio off kitchen for al fresco dining. The house is in immaculate condition with crisp and current style, this is not your typical house rental offering. No smoking. No services or utilities are included. Strong income, credit and references required.

Welcome to the Charming Cape style home located steps from Twin Island Lake in Pine Plains NY and enjoy outdoor activities as kayaking, fishing or relaxing in the peaceful screened in backyard porch. This adorable 1,296 sq ft. home offers on the first floor a living room bathed in natural light with Terracotta tile, an open functional kitchen that leads into the dining room, a full bathroom and conventionally large bedroom, making it an ideal spot for relaxation. The second half story offers two large bedrooms with one full bath. The basement offers a large media room, a workspace and washer/dryer. The property is graced with mature trees and a well-maintained landscaped lawn on .45 acres, offering ample space for outdoor activities, gardening, or simply enjoying the natural beauty in the backyard. 2018 a new roof with lifetime warranty, new front deck, new vanity & sink with fixtures, new front door and stamp concrete walkways. The Village of Pine Plains is a 10 min walk, Stissing Lake is an 8 min walk to the beach, playground, and tennis, pickleball, basketball courts. Stissing Mountain Multiple Use Area is 10 min drive, and opportunities for hiking, cross-country skiing, primitive camping, paddling, fishing for largemouth bass, yellow perch, chain pickerel, sunfish and brown bullhead. Millerton station (Metro-North) 13 min drive, Taconic State Parkway is 10 min drive, and the town of Rhinebeck is 20 min drive.

Welcome to the Charming Cape style home located steps from Twin Island Lake in Pine Plains NY and enjoy outdoor activities as kayaking, fishing or relaxing in the peaceful screened in backyard porch. This adorable 1,296 sq ft. home offers on the first floor a living room bathed in natural light with Terracotta tile, an open functional kitchen that leads into the dining room, a full bathroom and conventionally large bedroom, making it an ideal spot for relaxation. The second half story offers two large bedrooms with one full bath. The basement offers a large media room, a workspace and washer/dryer. The property is graced with mature trees and a well-maintained landscaped lawn on .45 acres, offering ample space for outdoor activities, gardening, or simply enjoying the natural beauty in the backyard. 2018 a new roof with lifetime warranty, new front deck, new vanity & sink with fixtures, new front door and stamp concrete walkways. The Village of Pine Plains is a 10 min walk, Stissing Lake is an 8 min walk to the beach, playground, and tennis, pickleball, basketball courts. Stissing Mountain Multiple Use Area is 10 min drive, and opportunities for hiking, cross-country skiing, primitive camping, paddling, fishing for largemouth bass, yellow perch, chain pickerel, sunfish and brown bullhead. Millerton station (Metro-North) 13 min drive, Taconic State Parkway is 10 min drive, and the town of Rhinebeck is 20 min drive.

AVAILABLE DECEMBER 1. Hudson Valley experiences await you with this bucolic setting at Picardy Farm. Once the home of one of the finest jazz musicians, composer, bandleader, actor and author, Artie Shaw, the 19th Century Greek Revival property includes The Garden House now available for lease. This 3 bedroom, 2.5 bath home is FULLY FURNISHED and ready for you to realign with nature and all that upstate New York has to offer. Entering the house from the rear of the property, the windowed, heated Foyer/Mudroom provides excellent storage. This leads into the 'Tavern Room', an open Living/Dining experience with wide board flooring and beamed ceilings. The fireplace is located on a wall of windows enabling wonderful light. The cozy kitchen includes a charming wall pantry and new appliances. There is a renovated bathroom with duel walk-in shower, clawfoot tub and a large laundry room on this level also. An office/den with more storage includes direct exterior access. Another bathroom and bedroom with exterior access are also here before we venture upstairs. There you will find the primary bedroom with vaulted ceiling, another bedroom and linen closet. Recessed lighting, security and thermostat control, mature landscaping, the use of a Yoga studio and gym are just a start to what you will find here. Located in serene Shekomeko Valley, nearby to the dining and shopping towns of Millbrook, Pine Plains Rhinebeck, Millerton and more. This is just two hours from New York City. Your peaceful Hudson Valley retreat is ready when you are. Available Dec. 1 . TENANT TO PAY AGENT FEE. Minimum 6 month lease ( 10% of total rental amount) OR One Year lease (One month fee)

Island Life in the Hudson Valley! Presently a very successful Airbnb ,3 separate parcels , a .25 acre island , .85 acre mainland , a 20x20 parcel on the East side of Twin Island Lake in Pine Plains. The island holds a Safari-like tent ,outdoor facilities, gazebo w firepit and cook grill .Access to island via canoe/kayak from the mainland that also holds a 2 story 1152 sq ft new Amish built barn that can be converted into living space . BOHA in process. Truly One of a Kind of property w limitless possibilities. Reconnect w nature running your own business or living lake life in this serene quiet town just 2 hours from NYC and 15 minutes from the TSP.

Over 177 acres of pristine, varied land, offering breathtaking western views of the Catskills, Stissing Mountain, and unforgettable sunsets. There is a drive in place with electric and well at the current house site, and easy access to the highest points of the property. There is over 2,000 feet of road frontage.

Investment opportunity in Pine Plains, NY. This is two buildings on two lots being sold together. 7788-7792 and 7794 South Main St. One 2 bedroom, two studio's and three 1 bedroom apartments. Six units in all. Fully occupied and has been for many years. One of the parcels has BOHA for an additional building with storefronts and offices. Two 2500 gallon drywells are already in place. These properties are located close to the town center. Plenty of off street parking. This is a great opportunity for turnkey rentals and future expansion. Second parcel is 7794 South Main St.

Bring your architect. This tranquil 24.95 acre property located above the Shekomeko Valley comes ready with a beautiful driveway and Dutchess County Board Of Health approval. The property has been prepped to build your dream estate. With its combination of open meadows, gracefully wooded areas, and pastoral views looking south towards Carpenter Hill and Stissing Mountain, you will have complete privacy. You will also be just minutes away from the villages of Pine Plains and Millerton and from Mashomack.

2 HOME PROPERTY! Lovingly cared for, tucked away in the town of Pine Plains! Conveniently located close to the center of town with a GORGEOUS view of the Stissing Mountain Fire Tower. Enjoy country living at its finest in this Cape Cod home situated on almost 25 acres of level land. The main house features hardwood floors, 3 bedrooms, 2.5 bathrooms and an unfinished 2nd floor with roughed in plumbing for a bathroom. This home is comfortable- with plenty of natural light to bask in and enough storage space to keep clutter out of sight! Large kitchen with island, breakfast nook and ample cabinet space. Downstairs you'll find full, unfinished space that only needs a touch of your imagination. On the same piece of property, you will find a guest or tenant's Ranch home with detached 1 car garage featuring hardwood flooring throughout, crown molding, 2 bedrooms, and more natural light. Both homes have whole-house, back-up generators. The property has 3 outbuildings: a feed barn, a horse stable and a garden shed. Other potential uses could be sheep farm, vineyard or Christmas Tree Farm. This estate offers you the ideal opportunity to lay down roots in the beautiful Hudson Valley.

Meticulously Maintained ELEVATED Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING Mountain Views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This is unquestionably the perfect entertainment perch which captures the expansive long views of the valley and hillsides. Fabulous open floor plan inside, with vaulted ceilings in living room with stone fireplace, large dining area, and light and bright gourmet eat-in kitchen with high-end appliances. Primary bedroom also has vaulted ceilings, stone fireplace, and large walk-in closet leading to primary bath. Den/study off of primary bedroom. Another great entertaining space is found downstairs including a large area perfect for games, exercise or media room with kitchenette. Also downstairs is a large second bedroom and updated bathroom. 3 car heated garage with massive storage space upstairs. 45KW generator. For the horse enthusiast, the property also includes a hay barn, paddock, 4 stall horse barn & tack room, equipment sheds and arena. Great riding trails abound. This exceptional property is move-in ready and utterly magical.

You always wanted a log cabin in the woods and this is your chance to own a 3 bedroom 1 bathroom home just outside the Village of Pine Plains NY. Close to Stissing Mountain, the polo grounds, everything outdoors and equestrian. The home features updated appliances, a new roof, updated, electrical service and a new boiler. This is a FannieMae Homepath Property.

Great opportunity for first time homebuyer or retirees. Great location, close to everything in Pine Plains Rhinebeck & Hudson. This won't last! One floor living, ranch style home, ready to move in.