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.

The "Mare's Nest" is a lovely 1890's equestrian property which has been home to the same family for the last 50+ years. The main house is a colonial featuring some fine original details with more recent additions of a greenhouse and a main floor bedroom wing that adds an additional kitchen, laundry and great room. There are a total of 4 fireplaces, 4 bedrooms and 5 bathrooms. The stables and a number of other outbuildings add a great deal of charm to the rolling 27 acres of lawn and pastures highlighted by the bucolic swimming pond. The heated inground pool is conveniently accessed from the great room and primary bedroom. There is a hot tub and a small pool house for storage of pool toys. The stable was home to many thoroughbred racehorses over the years and has 6 stalls and a fenced paddock. The 2 barns have 9 garage bays and lots of room for equipment storage. Conveniently situated near the village of Millerton NY and a 20 minute drive to the NY train at Wassaic.

Welcome to the Hartwell house of Spencer Corner. A home oozing with charm and history. A birth date that predates the birth of America this home circa 1769 offers the sense you have time traveled to 200 years ago with big views across the street of open fields and Winchell Mountain. Enjoy sunsets from your front yard as it sets behind the Taconic Mountains. Enter the home from the front door, a piece of living history. Made to protect the homeowners during the Revolution from intruders. Past the sturdy red door lies the dining room with beamed ceilings and hardwood floors. Also tucked in a corner is a little cupboard underneath the stairs. The living room offers a comfortable amount of space with antique wood detail, and views of Spencer Corner. The kitchen offers a large window allowing light to stream in, and open concept shelving. The primary on the first floor provides easy living with ample light, hardwood floors and a full bathroom with a walk in shower next door. Another structure connected by a carport or covered entertaining area could be used as a office, workspace, art/yoga studio or simply as storage. Enjoy spectacular sunset views of fields and Taconic Mountains from this property. An outdoor enthusiast delight: close to Rudd pond for swimming, Harlem Valley Rail Trail for walking and bike rides, and the Appalachian trail for hiking. Just a short drive to Catamount Mountain for skiing.

Beaver Mountain Farms. Picturesque c1900's farmhouse with multi-barn complex on 41+ acres with pond. Breathtaking vistas and pastoral farmland surround this extraordinary and well-maintained property. A lovely 3 bedroom/2 bath farmhouse is situated at the entrance of the property. Beautiful sun-filled eat-in kitchen overlooks pool surrounded by wildflower and perennial gardens. Living room with fireplace provides cozy seating. Generous-sized dining room with access to terrace on one side and enclosed porch on the other. Upstairs, primary bedroom en-suite and 2 bedrooms with full bath and laundry complete the second level. Wide hardwood floors throughout. The Northwest corner of the property boasts 2 large and newer Amish-built barns of exceptional quality with steel roofs. The first barn is approximately 180x80x20 (open span construction). Possible uses: Olympic-style horse arena. The second barn is a hay barn and roughly 160x50 with other potential uses. Near the farmhouse is an extraordinary 120x50' cow barn with gambrel roof and hay loft. Milkhouse has been converted to office with heat, electricity and bathroom. 40x25 Pole Barn with adjacent Pottery Shed located next to the cow barn. Enjoy the beauty of Columbia County from this exquisite setting. Close to Catamount Mountain Resort, Butternut Ski area, Appalachian Trail and Bash Bish Falls. Farm to table dining in Hudson and Rhinebeck.

Welcome to this charming Farmhouse nestled on over 19 acres of picturesque landscape, boasting breathtaking sunrises and sunsets along a serene scenic route. Embracing classic elegance, this tastefully renovated home seamlessly blends timeless allure with modern comforts. The heart of this residence is its epic chef's kitchen, featuring soaring vaulted ceilings, carrara marble counters, deVOL fixtures and hardware, a spacious pantry, and a grand oversized window offering panoramic western views of Indian Mountain. Entertain effortlessly in the inviting living and dining areas, enhanced by Dutch doors, exposed beams, and cozy fireplaces, all showcasing both eastern and western vistas. The main level also presents a convenient bedroom and full bath, along with a generous den boasting its own fireplace -- an entertainer's dream. Ascend to the upper level to discover a luxurious master suite with a sumptuous private bath and custom walk-in closet, accompanied by three additional bedrooms, two additional full baths, and a separate laundry room, ensuring practicality and comfort. A versatile landing that serves as a media room completes the upper level. Step outside to discover the in-ground heated pool, thoughtfully positioned to capture the surrounding scenery and breathtaking sunsets. Adjacent, the pool house beckons with a built-in stone outdoor kitchen, a half bath, and a western-facing patio, perfect for alfresco dining and relaxation.

Step back in time while enjoying modern amenities in this beautifully restored 1860s American Federal home in the heart of charming Lakeville Village. With recent updates like central air and a chef's kitchen perfect for entertaining, this 4 bedroom, 3.5 bath residence seamlessly blends period details with contemporary convenience. Gleaming hardwood floors and abundant natural light showcase the home's stately yet intimate proportions. The expansive updated kitchen opens to a stunning two-story dining room, ideal for family gatherings and formal affairs. Retreat at day's end to one of four light-filled bedrooms, including a generous primary suite. Stroll just seconds to Lakeville Lake, town fields, and restaurants from this coveted in-village location. Entertain on the bluestone patio and enjoy leisurely days in the flat, private backyard. Historic charm meets modern comfort in this lovingly restored Lakeville treasure.

Private waterfront pied a terre with direct water access on Spring Lake just outside of Rhinebeck, NY, this is a rare find. Hot tub. Grandfathered deck allows for basking right on the water. Large screened in porch. Open plan, good natural light, ideal weekender within the private East Lake community. Available immediately to start enjoying the approach of spring and summer.

A remarkable opportunity to own and renovate a home across from Sharon Hospital in the Village of Sharon, Ct. This home is in the center of Sharon and all that offers, such as the restaurants, library, hospital and all the associated doctor's offices. This home is served with both Town water and sewer and is minutes away from the train station to NYC.

A diamond in the rough with endless potential! Embrace the challenge, roll up your sleeves, and make this house a home that reflects your unique style and preferences! All the elements of a coveted country classic"wrapped up in one property"now available at the peak of Salisbury's historic Bunker Hill. The viewshed for this 3,678-square-foot home on 8.50-plus acres is protected by conservation easements. The shingle-roofed house settles perfectly into its surroundings, with open fields, an expansive yard in the back, and an enclosed kitchen garden to the side of the house. Inside are 4 bedrooms and 4.5 bathrooms, a formal living room with fireplace, a full butler's pantry, a kitchen with a four-burner Viking range. The house faces south, offering light and views. The full, finished basement has its own bathroom and a separate entrance. The house and setting make this a blue-chip property"in one of Litchfield County's most sought-after towns. The views alone are worth the investment - the rest is up to you!

Enjoy breathtaking natural views from every window of this recently renovated 4-bedroom, 3-bathroom residence, conveniently situated a mere five-minute drive from the quaint town of Salisbury. Inside, the newly expanded layout boasts a grand double-height great room adorned with rustic reclaimed wood beams and a captivating wood-burning stone fireplace. Gleaming hardwood floors guide you into the freshly upgraded kitchen and dining spaces. A cozy den on the lower level provides an additional area for gatherings, complete with a toasty radiant heat floor and a charming gas-burning stone fireplace. The main floor also hosts a convenient ensuite bedroom and powder room, while a staircase leads to two additional guest bedrooms sharing a well-appointed bathroom with a tub. The primary suite on this level offers a serene retreat, featuring a spacious walk-in closet, a tranquil sitting room, and maple floors with a tasteful pickled finish. Revel in breathtaking sunset panoramas showcasing Lion's Head and Mt. Riga, while mornings greet you with the gentle glow of sunrise over verdant fields on federally protected land. Step out onto the all-weather deck, the perfect vantage point to savor the stunning surroundings. Nearby trails beckon outdoor enthusiasts, with access to the renowned Appalachian Trail for hiking adventures. Plus, with Salisbury just a short drive away, convenience and leisure are effortlessly combined.

Experience the quintessential village charm in this delightful Cape Cod-style cottage nestled in the heart of Copake, NY and picturesque Hudson Valley. Enjoy gatherings in the spacious great room featuring a welcoming gas fireplace, creating a perfect setting for relaxation and entertainment. Step out onto the charming screened porch, where you can savor the fresh air and tranquil surroundings, ideal for morning coffee or evening unwinding. Just a leisurely 2-hour drive from NYC.

VIEWS! PRIVACY! Through oversized windows in the Great Room of this beautiful antique barn is a sweeping, uninterrupted southern view to Mt. Riga. The view seems to fill the room which features hand hewn beams and a soaring 18' ceiling. The open plan offers two seating areas, dining area, office area, and still enough room for a large piano. When purchased, the owners did a complete renovation, bringing it into the 21st century but with an eye to preserving its original character. They added insulation, replaced the siding with cedar clapboard, installed new windows, hardwood floors, propane heating, French doors, and a blue stone terrace with a French drain and retaining wall. The fully equipped kitchen was reconstructed with high end appliances and adjacent to the kitchen is a separate pantry with plentiful shelving, double oven and extra refrigerator. At the other end of the main floor is the den/TV room. Upstairs is a sitting area that connects to the ensuite primary bedroom with a walk-in closet and renovated bathroom featuring a stall shower and claw foot tub. There are two more bedrooms with a connecting bath on that floor. A two car garage barn contains an enormous upstairs space, perfect for storage or future updates. Set back from the road, this gorgeous 11.5 acre property with open meadows and mature woods is in a perfect, central location. Close to restaurants, area lakes, hiking, private schools, and Metro North at Wassaic. A true gem in the Litchfield Hills!

39 Bunker Hill is a rambling property with stunning distant views, the residence is set back to the rear high elevation of the property, a long driveway bordered by a wildflowers meadow, gardens, and a pond at the bottom of the sloping meadow affording long southern views of the distant hills. The centerpiece of the property is the dramatic post and beam barn home created by reassembling the best features of four antique barns circa 1857 that were located on the property and using the best parts to create two attached barns containing 7,066 square feet of finished living area. This meticulously crafted luxury home is a treasure inside and out. The ambiance of this extraordinary home is faithful to its intimate history as a barn, while offering generous spaces with more-than-enough modern amenities to seduce the most discriminating of homeowners The absence of windows at the front of the house belies the wonder experienced upon entering foyer where the first thing you see on the opposite side is a large window giving a preview of the long view across the valley and distant mountains. In the great room, where visitors are immediately confronted with multiple windows on two walls high-and-low boasting panoramic views to the east and south. Opportunities like this one seldom come along. Offered on 8+- acres pending survey. The total property is 39.614+- acres , more land is available.

Discover the perfect blend of modern luxury and spacious living in Lakeville, Litchfield County. This exquisite property, nestled on over four acres, provides ample space for relaxation, entertainment, and enjoyment. It features a charming screened porch and an elegant bluestone patio, which lead to a delightful heated saltwater pool. The house, a 9-room masterpiece with 4 bedrooms and 3.5 bathrooms, has undergone meticulous renovations before the current owner. The home's design includes a convenient first-floor primary suite. Additionally, there's a separate barn/garage, which houses an office/studio on its second level, adding to the property's appeal. Located just minutes from Salisbury village, this home is a serene retreat that doesn't sacrifice convenience for tranquility.

Capture the history and grandeur of Great Elm, the unparalleled 19th century Georgian colonial estate that was once the childhood home of William F. Buckley Jr., author and influential political commentator. 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 8,872 sq ft 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 fireplace, 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 William F. Buckley Jr., author and influential political commentator. 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 8,872 sq ft 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 fireplace, 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.

GRANDVIEW FARM ~ one of Sharon's most Iconic barns with legendary views and sunsets! Recently renovated, the interior showcases a unique blend of the original 1920s barn with wood beams and gorgeous refinished floors, new appliances, upgraded utilities, new roof and so much more! Situated on 28+ pastoral acres with scenic pond and pastures, the large picture windows from the barn-house capture the most magnificent western views rivalling a movie set. The residential portion of the barn features cathedral ceilings and an impressive open floor plan including the kitchen, living room and dining area with access to deck. Fabulous Great Room with wood stove and loft area, serving as an exercise room or study. 3 comfortably-sized bedrooms (primary en suite) and 2 full baths complete the main level. The Piece de Resistance is the 2022 installation of an 18' x 42' Saltwater Pool and spectacular 850 sqft Pool House. The tastefully built pool house possesses gorgeous European imported cobblestones with radiant floors, wood stove, kitchen by Devol, full bath and laundry. Large basement ~ great for storage. Enjoy this one-of-a kind property and its fantastical features that are simply unforgettable. Minutes to the villages of Sharon and Lakeville, and area private schools (Hotchkiss, Salisbury, Indian Mountain School and Berkshire School). Across from 181 acres and 2.5 miles of hiking trails at the Mary Moore Preserve (Sharon Land Trust). Once seen, the Grand View will not be forgotten.

Outstanding Salisbury Multi-Use Property An incredible Barn that was just renovated as a beautiful residence with 2 Great Rooms, a fabulous Kitchen, 4 Bedrooms, 3.5 Baths, 2 Offices/Dens, Central Air, beautiful original wood floors, a huge Attic and Basement. There is potential for a second Kitchen upstairs and for the 2 levels to be independent living spaces. Also, included is a 3-Bedroom Farmhouse with a Garage, as well as two open lots, which give the property a total of over 2 acres in 4 separate parcels. This Commercially Zoned edge-of-Town location is just down the street from the Scoville Memorial Library, the grocery market, restaurants and shops, and the Bike Path which runs from the east side of Salisbury to near Lakeville Lake. Town water and Town Sewer provide this property with endless opportunities!

Welcome to 42 Horse Shoe Lane! Built in 1960, this beautiful single-floor living ranch sits on a quiet cul-de-sac road in the Lakeville section of Salisbury. This well maintained ranch boasts hardwood floors throughout most of the home as well as a charming fireplace in the large, open living room. Large country, eat-in kitchen with lots of cabinets and storage space, two full baths. The basement has ample storage and a walk out to the back yard. The primary bedroom has a full bath and door to the sun porch. The office area could easily be used as a 3rd bedroom or play room The 2-Car attached garage leads into a large mud room with washer/dryer. The yard is a sanctuary of wildlife

Charming Cape in Ideal Location - This lovely Cape Cod home located on an amazing lot in idyllic Sharon CT is now available for sale. Cross the threshold of the extra deep wrap-around porch and enter the home with hardwood floors and generous proportions. The light-filled kitchen has a dining area with a large bay of bowed windows overlooking the side yard. A laundry room/mudroom is adjacent. The living room features an extra large double-height stone fireplace that has doors to a heated sunroom with wrap-around windows and access to the back patio with gorgeous views. The main floor primary bedroom has its own stone fireplace, a private sunroom, an en-suite bath, and ample closet space. Ascend to the second floor to discover two guest bedrooms and a full bath, providing comfortable accommodations for family or visitors. A detached two-car garage with loft storage space accompanies the property, featuring an attached room housing an exercise pool, perfect for relaxation and fitness. Enjoy the peaceful ambiance of country living, with convenient proximity to local amenities including in-town shopping, the Sharon Playhouse, Indian Mountain School, Hotchkiss School, and easy access to NYC train transportation. Don't miss the opportunity to make this tranquil retreat your own.

Welcome to 1 Jackson Hill Road. With its refinished wood floors and rustic ceiling beams this home blends modern comfort with historic details. The spacious living room with its cozy fireplace, flows naturally into the well-appointed kitchen and formal dining room. Natural light pours into this delightful cottage from the dining room bay window and the sky lights in the renovated bathrooms. Set off the main living area is the first floor primary en suite with ample closet space and soaring ceiling height. Upstairs the second bedroom boasts sturdy built-ins. The enchanting curb appeal is created by mature landscaping and flourishing perennials. A detached garage provides additional storage.

Welcome to 34 Jackson Hill Road, a recently remodeled retreat just a mile from the quintessential Sharon center. This ultra-chic haven is surrounded by apple trees and boasts captivating views of the CT/NY mountain range. Nestled into the rolling hillside, the black/white facade home features 3 full bedrooms, offering the sleeping capacity of 4. This residence is designed for sophisticated living, with an array of inviting spaces spread across both floors. Each floor presents real wood-burning fireplaces, access to balconies or patios, and full baths. The renovation includes new doors, trim, floors, plumbing, electrical, heating, and cooling systems. The main level seamlessly integrates the living, kitchen, and dining areas into an open floor plan. The kitchen is a culinary delight with white shaker cabinets adorned with brush gold hardware, stainless steel appliances, and a substantial 7-foot island. Recent upgrades encompass brand new hardwood floors with a rich dark chestnut stain, slate foyer tile, a new garage door, front walkway, and an architectural shingle roof. Conveniently situated just minutes away from shopping, restaurants, Route 4, and the metro north station, this property is accessible and commuter friendly. With its unparalleled combination of modern elegance and thoughtful updates, 34 Jackson Hill Road stands out as a distinctive and unmatched home in the current market. Welcome home to 34 Jackson Hill Road, where luxury meets tranquility.

Contemporary Farmhouse Masterpiece - Prepare to be amazed when you step foot on this exquisite 32-acre countryside retreat. A long, winding driveway beckons you toward a contemporary farmhouse masterpiece. Inside, breathe deep and take in the magnificent great room - soaring ceilings, walls of windows, and a 20-foot stone fireplace anchor this light-filled space overflowing with modern charm. The chef's kitchen is a culinary enthusiast's dream come true, flowing seamlessly into the sun-filled garden room and sprawling blue stone terrace. The first-floor primary suite offers complete privacy and tranquility, with a luxe bath, double walk-in closets, and a cozy terrace overlooking the gardens and glistening pond. Two more equally stunning bedrooms with ensuites are upstairs, along with a one-of-a-kind custom balcony overlooking the great room. With a separate one-bedroom guest house, this property provides ample space for both peaceful relaxation and gracious entertaining. Situated down a private drive and surrounded by protected conservation land, you're immersed in nature yet just minutes from the charming villages of Salisbury, CT, Millerton, NY, and Great Barrington, MA. Ideally situated near the many private & public schools, Catamount Ski Area and Aerial Park, and 20 minutes from the Wassaic Train Station. Make this modern farmhouse sanctuary your own personal retreat.

A Newly Renovated Iconic Salisbury Estate! - A stately Neo-Palladian 3,732 sq ft main house is perfectly sited on 28 acres surrounded by 300+/- acres of conserved land. This architecturally designed home has a perfectly proportioned living room with a wood-burning fireplace, and 3 sets of 10 ft French doors opening to the entertaining patio with sweeping mountain views. The newly renovated kitchen is light-filled and boasts Calcutta countertops and backsplashes, sleek fixtures, 2 dishwashers, and a bar area. The inviting dining room enjoys stunning views of the sprawling grounds and can easily seat 10-12. To round off the first floor there is an office off the living room with an adjacent newly renovated full bath. The second floor boasts 3 newly renovated ensuite bedrooms each with the beautiful Carrera marble bathrooms. The spacious primary suite has a wood-burning fireplace, a teak deck to gaze at the mountains and stars, a dressing room, and an expansive spa-like marble bathroom. Completing the upstairs is a sweet den ideal for watching TV, reading a book, or admiring the sunsets at this idyllic country setting on Salmon Kill Road, only one mile from the village of Salisbury. The property has a unique and important conifer collection of over 80 cone-bearing trees from around the world and has a creek rimming the property. This graceful Estate has spectacular 360-degree pastoral and mountain views.