Pine Plains NY Real Estate & Homes for Sale

Totally Private Top of the World Setting with Monster Catskill Views. 10-Min to the Center of Millerton NY/Sharon CT & 15-Min to Metro North Train. Graciously Scaled Rooms Throughout. 4 Fireplaces. The Ultimate Swimming Pool & Pool Area Complete with: Hot Tub; Outdoor Kitchen; Fireplace & Large Stone Terrace. Tennis Court. 3-Car+ Attached Garaging. 6 Paddocks with Run-In Sheds + Riding Ring & Barn. BIG Value for the Dollar!

Step into tranquility with this fully renovated Mid-Century gem tucked away on a private drive. Nestled on 5 acres of wooded bliss, this home offers the perfect blend of privacy and nature. Enjoy the serene surroundings from your brand new deck and porch, where every sunset feels like a moment of pure magic. With a finished basement offering additional space for entertainment or relaxation, this home is a true sanctuary for those seeking tranquility and style. Welcome home to your peaceful retreat.

Mare's Nest ~ Circa 1890's equestrian property once home to many thoroughbred racehorses. This charming Colonial has been a cherished family home for over 50 years. The estate showcases a combination of period details and recent additions including a primary bedroom wing on the main level and a greenhouse. The main house boasts 4 fireplaces, 4 bedrooms and 5 baths. Fabulous heated in-ground pool and pool house located off the great room. Across the 27 rolling acres of lawns and pastures, the pastoral beauty of the landscape unfolds, offering a pond and a serene escape into nature. Outbuildings add to the charm and functionality of the property, with garages, 6 stalls and a paddock ~ the latter 2 for equine pursuits. A few minutes to the vibrant village of Millerton with great farm to table restaurants, the movie house, and shopping. Easy access to the rail trail for walking and biking. 2 hours to NYC.

This historic 1845 Greek Revival estate, set on 11 acres of coveted Belgo Road in Lakeville, CT, offers a stunning blend of traditional design and modern conveniences. Fully restored in 2018, the primary residence features four ensuite bedrooms and is surrounded by bucolic views from each side. The first floor opens with an elegant entrance, leading to well-proportioned living areas that showcase meticulous craftsmanship. Award-winning landscaped gardens, designed by Renee Byers, create a seamless flow between indoor and outdoor spaces, featuring specimen trees, magnificent hardscaping, and kitchen and cutting gardens. The backyard invites relaxation with a swimming pool and outdoor shower, while the patio overlooks a wildflower meadow-perfect for entertaining and dining al fresco. A 3-bay garage, built in 2016, includes a sun-filled loft with high ceilings, oversized windows, and a bedroom with a full bath and kitchenette, adding versatility to the property. Sustainable features such as solar panels and an electric vehicle charger offer modern efficiency. The property is adjacent to Taconic State Park, part of one of the largest unfragmented forests between Virginia and Maine. A converted barn with two separate apartments and its own driveway provides ideal spaces for hosting guests or rental opportunities. Experience the best of country living in Litchfield County! Nearby amenities include Lakeville Lake, the towns of Salisbury, Sharon, and Millerton, a train to NYC.

Design and build your dream home with Welcome. This property pairs best with the Monaco Cabin model, but it pairs with 13 other Welcome models as well. Customize your new home-fully online-with guaranteed pricing. Estimated 12-18 months from construction start to move-in. Buildability and pricing have been confirmed by Welcome, with a promise of no overages or surprise costs during construction. The Monaco by Welcome is a luxurious spin on the traditional cabin. It features 3-4 bedrooms and 3 full bathrooms, as well as an array of luxury amenities for the modern lifestyle. The open-concept kitchen and living area provide easy access to the rear deck, offering an ideal space for entertaining or unwinding. Natural light floods the kitchen and living room areas through floor-to-ceiling windows. Once you've made your design selections and have an accepted offer on both the construction costs and the land, Welcome handles everything else, from permitting through construction and everything in between. (See MLS #2408038 for land-only information.)

Design and build your dream home with Welcome. This property pairs best with the Modern Cabin 3 home model, but it pairs with several other Welcome models as well. Customize your new home-fully online-with guaranteed pricing. Timing is estimated at 12 - 18 months from construction start to move-in. Buildability and pricing have been confirmed by Welcome, with a promise of no overages or surprise costs during construction. The Modern Cabin 3 by Welcome is a luxurious spin on the traditional cabin. It features 3 bedrooms and 2 full bathrooms, as well as an array of luxury amenities to meet the needs of even the most discerning owner. The open-concept kitchen and living area provide easy access to the rear deck, offering an ideal space for entertaining or unwinding. Upstairs, the loft space adds a touch of versatility and provides ample room for creative expression and personal design. Once you've made your design selections and have an accepted offer on both the construction costs and the land, Welcome handles everything else, from permitting through construction and everything in between. (See MLS #243314 for land-only information.)

An opportunity to curate a spectacular 10 acre parcel located on the NY/CT border with majestic views to the East and the West. The property is partially cleared and is board of health approved with an existing 4 bedroom septic, electric service, and well. There is currently a 1 bedroom home which could serve as a guest cottage for your three bedroom home or it could be raised and you can build your 4 bedroom dream home. The location is private and quiet and nestled within an area of prime estates, farms and stunning pastoral vistas. Minutes to the pristine town of Sharon, Ct and Amenia, with Metro North just a short drive. Property like this, in a perfect location is extremely hard to come by.

Country Home In Private Location - This home is located on a private road in Lakeville and features a first-floor primary, a large living room with wood wood-burning fireplace, and a screened-in porch overlooking the grounds. The eat-in kitchen has a separate laundry room, wood cabinets with granite countertops, and sliding glass doors that open to the back deck perfect for outdoor dining or relaxing. The gunite swimming pool has plenty of room for seating and includes an outdoor dining area under a wisteria-covered pergola. Conveniently located near the local private schools, shopping, restaurants, the Sharon Playhouse, and Wassaic train station. Enjoy country living at its best!

Design and build your dream home with Welcome. This property pairs best with the Modern Farmhouse 4 Grand home model, but it pairs with several other Welcome models as well. Customize your new home-fully online-with guaranteed pricing. Timing is estimated at 12 - 18 months from construction start to move-in. Buildability and pricing have been confirmed by Welcome, with a promise of no overages or surprise costs during construction. The Modern Farmhouse 4 Grand by Welcome features the perfect balance between rustic country style, with contemporary and bold, yet sophisticated, finishes. This 4-bedroom, 4-and-a-half bathroom, one-story home, with an expansive loft, invites lots of natural light and boasts an L-shaped layout that enables a sprawling view of the backyard from almost every room. Once you've made your design selections and have an accepted offer on both the construction costs and the land, Welcome handles everything else, from permitting through construction and everything in between. (See MLS #24018663 for land-only information.)

Almost paradise!..lure of the good life in Taylor Brook Hollow. A most coveted location with parklike grounds, statuesque hardwoods, a wildflower meadow & a crystal clear brook nourishing an abundance of watercress is a nature lovers setting for this countryside cape. The home has been well maintained, has 4 bedrooms, 2 full baths, (one recently renovated) large formal living room with a fireplace, eat in kitchen, formal dining room and family room with sliders to the rear deck. Full dry basement a plus, lots of sunlight and a lantern lit driveway. Covered Bridge is a private road with only 9 residences. Situated in the beautiful Litchfield Hills you'll be in close proximity to the Berkshires MA & Hudson Valley NY and all that is offered in fine dining with farm to table fare, theatre, hike the AT, cycle or walk the rail trail, ski the slopes, play in our many lakes and rivers. Medical facilities, public & private schools, shopping are all nearby. 1-2 hrs to Bradley Int and NYC airports respectively.

Welcome to this stunning hilltop retreat in the heart of Sharon, Connecticut, built by Denmark-based Trelleborg. Nestled on a sprawling 1 acre property, this 4-bedroom, 3.0 bath (town card says 3BR 2.5BA but is wrong) contemporary Spanish-tiled cape home offers a tranquil escape with breathtaking views and Japanese gardens amongst unprecedented seclusion. Upon entering, you're greeted by an open-concept living space that features natural pine ceilings, hardwood floors throughout, luxurious upholstered walls, and floor-to-ceiling windows that allow natural light to flood the home and highlight the serene landscape. The spacious first floor includes a gourmet kitchen with granite countertops, stainless steel appliances, and custom cabinetry flows seamlessly into a dining area with cathedral ceilings and a wood burning stove, perfect for relaxing on chilly evenings. Rounding out the first floor is a breathtaking 2-story library wing, perfect for large parties or quiet evenings with a book. Upstairs, the primary suite is a private haven, with two walk-in closets and a spa-like ensuite bathroom with a soaking tub and separate shower. Two additional bedrooms upstairs are generously sized, and there is a 4th bedroom (town card says 3 bedrooms) on the main level. Step outside onto the expansive patio - a gardeners dream dotted with exotic plantings and framed by elaborate landscaped stonework in a peaceful, nature-filled setting.

Nestled on just over an acre of land, you'll find this lovely 2 bed 1 bath cottage, built on the back of the property allowing for a quiet and peaceful place to relax and unwind. This house has lots of natural light as there are lots of windows and skylights in nearly every room. The well landscaped property has mature trees, flower gardens and natural stone, a truly peaceful environment. The house is just as inviting, a walkway takes you through a small patio into the mud/dining room with a wall of windows, vaulted ceilings and brick floor. The kitchen is well laid out with breakfast bar and small center island, the vaulted ceilings and skylight make this a happy space. The living room is large with wood burning fireplace, vaulted ceilings, skylights and french doors to a terrace on the backside of the house. The primary bedroom also has vaulted ceilings, a skylight and a large closet. The 2nd bedroom is off the living room and has a large closet. The bathroom has natural light, a tub/shower combo and a stackable washer and dryer. Located just off Mudge Pond Road this property is minutes from downtown Sharon, Salisbury and Millerton NY. The location is a treasure trove of local charm with close proximity to shops and restaurants, Sharon Playhouse and Sharon Town Beach. Just 15 minutes to Metro North Train, and two hours train ride to NYC.

Modern Country Estate On 21+ Acres - Discover this idyllic 5 bedroom, 7 bath, 6,261 sq. ft. Modern Shaker Main House with a 3 Bedroom, 1,987 sq. ft. Guest House designed by renowned architect Alan Wanzenberg and landscaped by Susan Child. Located on 21+ acres in Lakeville, CT, this estate offers peaceful seclusion and convenient access to local amenities. The property features mature trees, orchards, stonewalls, and perennial gardens, exuding warmth and comfort. The main floor includes a living room, dining room, family room, and screened porch, each with wood-burning fireplaces-the dining room and chef's kitchen open to a bluestone terrace with Southern views. The first floor also has an ensuite bedroom and a mudroom. The second floor boasts a primary bedroom with a fireplace, a luxurious bathroom, an office, three additional ensuite bedrooms, a laundry room, and a den. The lower level offers a recreational room/gym and a wine cellar. The guest cottage overlooks the heated gunite pool and includes 3 bedrooms, 2 baths, a kitchen, and a living area. The property also features a 1/2 basketball court and a red barn for storage. Enjoy privacy, comfort, and accessibility near Lakeville Lake, Salisbury, Sharon, Millerton, NYC train, Hotchkiss School, and Indian Mountain School. Experience the beauty and tranquility of this exceptional Connecticut property. Schedule a viewing today!

Charming 1 bedroom, 1 bath lake cottage, just 2 hours from NYC and 10 minutes from the Wassaic Train Station. Nestled in beautiful Litchfield County with views of and access to Mudge Pond, enjoy year-round activities like swimming, boating, fishing, kayaking, and ice skating. This recently updated retreat features a new propane heating system and appliances. The den provides extra space for an office or guest room. Perfect for a weekend getaway or year-round living, it's close to the cultural and outdoor attractions of the southern Berkshires. Come see this special home today!

Put your personal touches on an in-town Lakeville home with an inground pool! Currently a one level home with home renovation plans that have been designed and approvals are in process. Proposed renovation is designed to include an open floor plan on the 1st floor. The proposed second floor will have three bedrooms including a primary ensuite, a second full bathroom and a laundry room. The proposed plan includes an attached screened porch and inground pool with bluestone patio. There is a wonderful large fenced in backyard perfect for play and hosting. Property is being offered for sale as-is with fully designed renovation plans & construction documents. Property is owned by a local contractor who can facilitate the renovation at an additional cost. Purchase now and work with the designer to add your personal touch! Work will start in 2025 either way - come take a look! All room sizes are approximate

Charming three bedroom two bath Antique Farmhouse situated in close proximity to the Historic Sharon Green with expansive private backyard. The recently renovated kitchen is light and bright with a vaulted ceiling, hardwood floors, contemporary appliances, elegant quartz countertops, and ample storage space, accommodating a kitchen table or center island with ease. The first floor also features a remodeled custom tiled full bathroom with laundry cupboard, a cozy bedroom, and a welcoming foyer. An expansive living room graces the home with high ceilings, custom built-ins, and fireplace. Upstairs, two additional bedrooms, and a full bath, complete the home, along with an attached garage and enclosed porch. A full deck off the kitchen offers pastoral views of the level backyard surrounded by mature trees, a detached garage and shed for additional storage. The location is a treasure trove of local charm, with close proximity to Sharon Town Green, shops and restaurants, Sharon Playhouse, Audubon Center and Sharon Town Beach, near the villages of Amenia and Millerton, NY, Salisbury CT., and Great Barrington MA,10 minutes to Metro North Train, and two hours drive to NYC.

107 Main Street is located in the heart of Sharon's Historic District - a tucked away convenient village setting. Originally the carriage barn to a neighboring home, it was reimagined by a previous architect owner. Brimming with character and charm, this 4 bedroom, 2 and a half bath home offers a spacious & historic layout. The ground floor has 2 entrances: a main entrance foyer, and a sun-lit mudroom with slate tiles which opens to a large kitchen with a central island and new appliances. Next to it, a separate formal dining room with a secondary staircase that leads to the upstairs bedrooms. The cozy family room has custom built-in cherry cabinets and bookshelves, a large double-flue fireplace and french doors that open to an expansive, peaceful cedar deck and a bluestone patio, providing ample outdoor gathering space. Impress your guests with the full-height great room ceilings from the main entrance, two large skylights and a second fireplace. Entertain in the sunny living room that overlooks an established perennial garden. Continuing upstairs by way of a wide formal staircase, you'll find a lofted second level with exposed wooden beams throughout. Off the loft is the primary bedroom with a Palladian window, high ceilings, and a walk-in closet. Through the opposite side of the loft, are 3 additional, and generously sized bedrooms with another full bath, newly renovated. This rich in character historic home off the Sharon Green is not to be missed.

HYDRANGEA COTTAGE - Perfectly picturesque c1740 English-style colonial in the heart of Sharon. This lovely 2-3 bedroom, 3.5 bath home has been meticulously renovated and adorned with Farrow & Ball paint, creating comfortable living spaces with modern luxuries. Of note, this in-town gem features a charming eat-in kitchen with high-end appliances and gorgeous soapstone sink. Dining room with fireplace provides access to large deck, ideally positioned to capture stunning mountain views and sunsets. Large living room and study with period details and beautiful wood floors. Upstairs: Primary Bedroom en-suite with glass shower and porcelain console sink. Second Bedroom and full bath with clawfoot tub. Downstairs: fabulous extra room on lower level with outside access. Great as a study/exercise room or as additional bedroom. Also on lower level ~ full bath with clawfoot tub and washer/dryer. Flower gardens surround this sweet and very chic country cottage. Close to area private schools (Hotchkiss, Kent, Salisbury School and Indian Mountain School). Walk to the Historic Sharon Green, Hotchkiss Library, Sharon Playhouse or Historical Society. 2 hours to NYC. Absolutely enchanting!

Welcome to Hilltop Road. This stunning property offers the perfect blend of country living and urban convenience, nestled on 4 picturesque acres with a pool. With seven spacious bedrooms and 4.5 luxurious baths, there's plenty of room for family and guests alike. Step into the heart of the home-a breathtaking kitchen that's a culinary dream, featuring a grand center island and a captivating window that frames your idyllic surroundings. Enjoy cozy evenings in the family room with a fire or unwind on the charming screened-in porch with a beautiful view, designed for relaxation and entertainment. Ideal for entertaining and social events, this home features an expansive master suite along with four additional bedrooms located on the second floor. Ascend to the third floor, where you'll find two more spacious bedrooms and a versatile and bright playroom or gym. This layout ensures that everyone can enjoy their own space while providing ample room for memorable gatherings. Step outside to discover beautifully landscaped grounds, complete with a heated pool, fenced-in garden and a large bluestone terrace ideal for grilling and gatherings. Designed for entertaining and luxurious living, this home is not just a place to live-it's a lifestyle. Come and experience Hilltop Road for yourself.

Welcome to Sharon Green Condos - Comfort and Convenience in a Coveted Locale. Discover this 2 bedroom 2 full bath second-level unit presenting a blend of comfort, convenience, and easy living. As you step inside, you're greeted by a warm and inviting living room, complete with a cozy fireplace and sliders to a private balcony that sets the tone for relaxed evenings and intimate gatherings. Features an ensuite primary bedroom, dining room, and large pantry with laundry. Included is a one-car garage, adding to the ease of this turnkey lifestyle. Situated close to the village, residents have the convenience of nearby shopping, dining, outdoor activities, and cultural events. The condo's proximity to private schools and the Metro-North train station makes it an ideal choice for those seeking a blend of suburban tranquility and commuter accessibility. Property being sold "AS IS". HOA= $305/mo Building acct =$195/mo.

The modern farmhouse in Lakeville, Connecticut, is a testament to the harmonious blend of contemporary design and serene rural living. With its expansive windows inviting the outside in, this home offers a living experience that celebrates the natural beauty of Lakeville's wetlands and meadows. The property's thoughtful layout, including three spacious bedrooms and a versatile loft workspace, provides ample room for relaxation and creativity. Future homeowners have the flexibility to convert space into a fourth bedroom or add a garage, tailoring the space to their needs. The interior's high ceilings and custom staircase accentuate the home's open feel, while the central fireplace and balcony offer cozy spaces to unwind. This residence is not just a house but a retreat that promises a lifestyle of peaceful elegance, moments away from local amenities and the scenic rail trail.

SPLENDID VINTAGE CAPE:No expense was spared in this modern revival of a classic, 1940's expanded cape and enchanting property. Its grandeur is enhanced by the intimate setting; nearly 3 acres of beautifully landscaped mature gardens designed to create separate environments for the gunite pool /patio area, cottage with bedroom, bath, living room, kitchen and the stone patio at the rear of the house, yet another richly designed private space. All is framed by ever-blooming specimen plants and evergreen trees that can be viewed from every room. The gracious primary suite; with a grand bath overlooking the glorious gardens, BR with fireplace, adjacent screen porch and richly paneled library completes a private wing with all the romantic flair of a 5-star country resort. A warmly inviting country, eat-in-kitchen with Smallbone cabinets, high-end appliances and fixtures, opens to a two-story family room with fireplace and French doors to access back and front yards/patios. The charming, original section of the home has a living room with fireplace and dining room on the main floor., 3 bedrooms 7 1.5 baths on the second floor, playroom in the basement and spacious laundry room on the main floor with mudroom access completes the main living areas. Hidden in the landscape, amid the most impressive estates of New England, in the heart of Sharon, Ct.this "Currier and Ives" picture perfect property, is a delight to the senses.

A simple ranch in a spectacular location...an opportunity to create your dream house in a secluded parcel in the Town of Sharon. The land was part of an older farm, so surrounded by meadows filled with wildflowers and wildlife. Long, views to the east over wind blown fields with mowed trails to walk. Beautiful sunrises and big skies to enjoy. The driveway is a quarter mile long with underground utilities for unspoiled landscapes.

Capture the history and grandeur of Great Elm, the unparalleled 19th century Georgian colonial estate that was once the childhood home of author and influential political commentator, William F. Buckley Jr. Nestled in the heart of Sharon, CT, this prestigious property is a rare opportunity to acquire a residence steeped in historical significance and architectural elegance. Great Elm boasts 8,072 sqft of luxurious living space, crafted with impeccable design choices throughout. From the art deco bathrooms to the William Morris wallpaper, every room exudes sophistication and meticulous care. William Buckley Sr. purchased the original 1812 house in 1923, expanding it over time to accommodate his growing family. The main level primary bedroom suite and gracious sitting rooms, each with gorgeous detail and wood burning fireplaces, open to the dramatic three-story Atrium, a year-round haven reminiscent of New Orleans. Upstairs are 7 beautifully appointed ensuite bedrooms, one of which is used as a gym; another as an office. This property is the anchor of a community of homes joined by an Association that manages the 50 magnificent, park-like acres and amenities, including a heated, Gunite pool, pool house, tennis and paddle/pickle courts. This spectacular property in the beautiful Litchfield Hills is more than just a residence; it's a chance to own a piece of U.S. history. Close to Hotchkiss, Salisbury, Indian Mountain and Millbrook Schools. Only 2 hours to New York City.

Capture the history and grandeur of Great Elm, the unparalleled 19th century Georgian colonial estate that was once the childhood home of author and influential political commentator, William F. Buckley Jr. Nestled in the heart of Sharon, CT, this prestigious property is a rare opportunity to acquire a residence steeped in historical significance and architectural elegance. Great Elm boasts 8,072 sqft of luxurious living space, crafted with impeccable design choices throughout. From the art deco bathrooms to the William Morris wallpaper, every room exudes sophistication and meticulous care. William Buckley Sr. purchased the original 1812 house in 1923, expanding it over time to accommodate his growing family. The main level primary bedroom suite and gracious sitting rooms, each with gorgeous detail and wood burning fireplaces, open to the dramatic three-story Atrium, a year-round haven reminiscent of New Orleans. Upstairs are 7 beautifully appointed ensuite bedrooms, one of which is used as a gym; another as an office. This property is the anchor of a community of homes joined by an Association that manages the 50 magnificent, park-like acres and amenities, including a heated, Gunite pool, pool house, tennis and paddle/pickle courts. This spectacular property in the beautiful Litchfield Hills is more than just a residence; it's a chance to own a piece of U.S. history. Close to Hotchkiss, Salisbury, Indian Mountain and Millbrook Schools. Only 2 hours to New York City.