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!

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.

Experience the pinnacle of modern living with this spectacular and recently renovated 4 BDR/4.5 home off of Belgo Road in Lakeville, CT. Set on a very private 5.7-acre parcel, this property offers breathtaking views in a lightly wooded setting adorned with beautifully manicured lawns. Inside, the new finishings are impeccable, with clean lines and bright spaces that invite natural light to cascade through the impressive large windows from every vantage point. The main level boasts an open floor plan including a striking and spacious kitchen (equipped with a Wolf oven, Sub-Zero refrigerator, stunning island with quartz countertop, and a convenient walk-in pantry), as well as a dining area and living room offset by a tall center fireplace and flanked by large picture windows. A large room with full bath (currently used as an office/den) can also be used as a primary bedroom. Off of the open balcony on the second floor are 3 en suite bedrooms each beautifully positioned to capture the outdoor light ~ 2 bedrooms have their own porches. The home's design is a testament to elegance and sophistication, with landscaped grounds that complement a luxurious saltwater Gunite pool and cozy firepit, creating an idyllic outdoor oasis for relaxation and entertainment. 2 car garage offers ample space for vehicles and storage. Generator. Close to area private schools, hiking/biking/walking trails, and farm-to-table restaurants. Short drive to the Hudson Valley. 2 hours to NYC.

A wonderfully built home privately set atop a knoll with sensational (expandable if desired) distant views to the South and West, over the nearby hills, and into NY state. All on one floor, it was superbly built, with premium quality materials and mechanicals. It has a new roof, along with new flooring in many rooms, other interior decorative touches. It has an excellent living design, all on one floor, with wide hallways and doorways. There is a lot of invisible and perhaps overbuilt quality, from a concrete based foundation and, main level under-flooring, to its interior, from the basement to the roof. The site is sun filled and so is the residence, being built, and designed, with large windows and ceiling skylights, both to 'capture' the sun in the cold months, and 'deflect' it in the warm months. Every room has individual heating controls for the radiant heating that exists throughout the home. The home is fully airconditioned, and also is outfitted with business grade (by Comcast) whole house communication equipment, enabling excellent connectivity in every room. The land has a suitable location for a pool, if desired, but is otherwise easy to maintain in its current state. The cavernous basement is ideal for storage, a home theatre, or other, non-storage uses, with large spaces for any such use. There is a ground level exit. Rooms, hallways, and doors are all sized for easy movement throughout the home.

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!

Welcome to Peony Hill. A Hilltop Haven in Lakeville Perched at the crest of a long, private drive this Lakeville retreat is where timeless sophistication meets everyday comfort. Fully renovated in 2020 with no detail overlooked, the home is equal parts refined and relaxed-a quiet triumph of thoughtful design and modern convenience. Step into the heart of the home: a stunning new kitchen outfitted with top-of-the-line appliances, including a five-burner Bertazzoni gas range. Whether you're hosting brunch in the sun-drenched breakfast nook or gathering for a dinner party at the dining table, this kitchen was made for effortless entertaining. Just off the kitchen, a chic powder room wrapped in bold Cole & Son wallpaper and a practical laundry room add both flair and function. The open floor plan unfolds into a luminous living room, where sunlight streams through generous windows, illuminating new flooring and tasteful, understated finishes. Upstairs, four comfortable bedrooms-including a serene primary suite-offer peaceful respite. The primary bathroom is a true sanctuary, featuring a soaking tub, separate shower, and a smart mirror that reveals time and temperature with a touch of magic.

1st Time on Market in 40+ Years. Truly Wonderful 4 Bedroom, 4.5 Bath Totally Chic Period Home with Additions. Property is 12+ Acres & Encompasses Both Sides of a Lesser-Known Coveted Town Road. Less than 1-Minute to Mudge Pond Lake & the Town Beach. The Famous "Twin Oaks" Sharon Land Trust Field is Just Down the Street. Lots to be Discovered here including a Jaw-Dropping Great Room with Fireplace & 20' Ceilings. Main Level Primary Suite includes: Dressing Room, Office, Closeting & Screened Porch. Inviting Library with Fireplace & Antique Beams. Large Dining Room with Fireplace Speaks to an Eat-in Kitchen bathed in Light. Separate 600 Square Foot 1-bedroom Guest Quarters Above 2-Car Garage.

Sprawling Lakeville Compound On 21+ Acres - This idyllic gathering place boasts a 5-bedroom, 7-bath 6,261 sq. ft. Main House and a 3-bedroom, 2-bath, 1,987 sq. ft. Guest House overlooking a Heated 55-ft. Gunite Pool. The Main House was designed by renowned architect Alan Wanzenberg and landscaped by award-winning designer Susan Child. This compound offers peaceful seclusion and convenient access to local amenities and schools. The first floor of the Main House includes a chef's kitchen and a living room, dining room, family room, and screened porch 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 and a luxurious bathroom, an office with a fireplace, three additional ensuite bedrooms, a laundry room, and a den. The lower level offers a recreational room/gym, a wood-paneled wine cellar, and extensive storage. The property features mature trees, orchards, stonewalls, perennial gardens, and a half basketball court that could readily be converted to a pickleball court. The charming timber frame red barn built by New England Barn Company is an open canvas for car storage, golf simulator, party barn, or office/studio space. Enjoy privacy, comfort, and accessibility near Lakeville Lake, Salisbury, Sharon, Millerton, NYC train, Hotchkiss School, and Indian Mountain School.

Welcome to a peaceful country retreat in the heart of Amenia, NY. This spacious 4 bedroom, 3 full bath ranch home offers the perfect blend of comfort & privacy nestled in a quiet, rural neighborhood. Enter to a natural light filled LR/DR area with a cozy fireplace, and hardwood floors throughout most of the house. Kitchen is small & in need of updating, but there is potential to expand. Sliding glass doors open to a deck to enjoy the private backyard. A large bedroom with adjacent bath & shower stall has a separate entrance that allows for potential mother/daughter occupancy. Down the hallway from the combined LR/DR area are three good sized bedrooms that share a full bath w/tub. The finished basement adds additional living space, complete with a bath w/shower stall & washer & dryer. A walk out from the basement leads to a concrete patio and at the bottom edge of the property is a large shed providing an abundance of storage. Newer Oil Furnace, Brand New Water Softener. Located just minutes from the village of Amenia, NYC within 2 hrs by car, Wassaic Metro-North station within 5 miles, Rail Trail less than 1 mile, Border of Sharon, CT within 5 miles with nearby CT Private Schools, Sharon Playhouse, Hiking, Antiquing, Skiing all within close proximity making this property convenient to many cultural, athletic & enjoyable adventures & festivities. Agent/Owner related. Property is a trust & being sold "As Is".

Welcome to 36 Lincoln City. A beautiful, modern and chic renovation in bucolic Salisbury, CT. This remodel includes custom cabinetry, a high end kitchen with stainless appliances, and all new mechanicals to include HVAC. This stunning home has 3 bedrooms all in-suite with tiled showers. A powder room and mudroom/laundry area are located on the first floor. A large covered deck on the back of the house has views of the expansive lawn and seasonal town views. The house is near The Hotchkiss School, Salisbury School, Indian Mountain School and is conveniently located near Salisbury Central School.

Prime Opportunity in the Heart of Downtown Lakeville/Salisbury. A rare chance to own a distinguished Federal-era residence, seamlessly transformed into a versatile commercial space while maintaining the possibility of restoring it to a stately private home. Nestled in the vibrant center of Lakeville, this property blends historic charm with endless potential. Brimming with timeless character, the building showcases soaring ceilings, elegant wood moldings, and classic architectural details throughout. The main level features eight spacious rooms, allowing for customized configurations, while a half bath and laundry room add functional convenience. Upstairs, the owner's private residence offers additional flexibility, easily transitioning to expanded living quarters. This level boasts two bedrooms, an office, two inviting living areas, kitchen, and full bath-all bathed in natural light and rich in character. A standout feature is the expansive 670 sq. ft. deck-a serene retreat framed by specimen trees and overlooking the beautifully landscaped grounds. The .76-acre lot offers generous rear parking, a lush green lawn, mature trees, and a meandering brook, enhancing the peaceful setting. The 1,152 sq. ft. basement provides further versatility, complete with a full bath, workshop space, mechanical room, and ample storage. Positioned in the highly sought-after Northwest Corner of Connecticut, this exceptional property presents a unique opportunity to live and work in one of

This distinguished 1880s Victorian residence in the heart of Lakeville village offers a masterful blend of period craftsmanship and contemporary luxury on 2.5 private acres. Located moments from both the town green and Lakeville Lake, this meticulously restored 5-bedroom estate presents refined living in one of Litchfield County's most sought-after locations. The welcoming wrap-around covered porch leads to an elegant entry hall featuring a striking curved staircase. Grand proportions define the formal rooms, where original wood-burning fireplaces, soaring ceilings, and oversized windows create an atmosphere of timeless sophistication. The gourmet kitchen showcases top-tier stainless appliances, substantial island, and bespoke wood cabinetry, with a bright dining area flowing to the generous rear deck overlooking the grounds. The second floor houses a bright primary suite with ensuite bath, three additional bedrooms, a dedicated home office, and a luxurious bathroom featuring custom marble, Waterworks fixtures, and radiant heat flooring. A stylish laundry room and thoughtful storage complete this level. The third floor provides a secluded guest retreat with original wood floors, flexible studio space, and cedar-lined storage. The property's exceptional amenities include a versatile two-story barn with basement-ideal for studio, workshop, or recreational pursuits-plus a detached one-car garage. The Serene grounds frame this village estate, offering the rare

Just in time for summer! Welcome to 21 Perry Street-a beautifully maintained home that perfectly blends country charm with in-town convenience. The spacious main level features a primary suite complete with a large walk-in closet and private bath, offering comfort and functionality for everyday living. Upstairs, you'll find two generously sized bedrooms and a full bath, ideal for family, guests, or a home office. The lower level offers more space with laundry, game room, work space or an in home gym. Spend sunny days lounging by the gunite in-ground pool, nestled in a well-kept and private yard-an ideal setting for summer entertaining. When the seasons shift, the cozy yet elegant living room becomes the perfect place to relax and take in the beauty of New England winters. This property is in excellent condition, reflecting the owners' exquisite style and offering true move-in readiness with timeless appeal. A rare opportunity to enjoy year-round comfort in a sought-after location-don't miss it!

Beautifully maintained four bedroom home with two full baths located on the corner of Perry Street and Farnum Road, just a short distance to Lake Wononscopomuc and downtown Lakeville. First floor offers a spacious country kitchen with great counter and cabinet space & laundry, large dining area with bright living space and woodstove, an additional living room space, two large bedrooms with double closets, office and a full bath. Upstairs are two more bedrooms and a full bath with a claw foot tub. Very nice hardwood floors throughout this home. Walkout basement with storage and a one car garage. This home has private parking on both Perry Street and Farnum Road. Relax outside on the slate patio. Nestled in the Northwest Corner, this home is just a short distance from Lakeville Lake, downtown Lakeville, Salisbury and Millerton. All room sizes are approximate.

Discover Timeless Elegance and Potential at 400 Gay Street, Sharon CT Situated on the edge of over 20 acres of picturesque land, this 1940 hand-built brick house awaits a visionary's touch to update the interior. There are several possible building sites that would accommodate a large Main house. This estate presents a rare chance to own a piece of Sharon's history and to craft a sanctuary tailored to your lifestyle. Property Highlights: * Historic Brick House: Built with care by the original owner, this home offers a solid foundation for restoration and customization. * Expansive Acreage: Over 20 acres of diverse landscapes, featuring open meadows and partially wooded areas with nature trails, perfect for outdoor enthusiasts. * Breathtaking Views: Enjoy serene long views of Mudge Pond, complemented by the enchanting spectacle of sunsets. * Privacy Meets Convenience: Positioned adjacent to protected lands, ensuring tranquility, yet conveniently close to the charming village of Sharon and the esteemed Hotchkiss School. * Additional Structures: Several outbuildings present on the property offer a multitude of uses, from workshops to storage or a number of garage bays. Whether you're drawn to the allure of a restoration project or the call of the land's natural beauty, 400 Gay Street is a canvas for your imagination.

1880's perfection, a true rare find in the heart of Sharon, CT. Magnificent seven bedroom, 5.5 bath estate, beautifully preserved and situated on a sprawling 4-acre lot with a pool. Large eat-in kitchen with massive center island. Screen porch overlooking the pool with beautiful hilltop views. 79 Hilltop masterfully combines historic charm with modern luxury, offering you the best of both worlds. Country living with complete privacy just steps from town.

Architectural Mountain View Estate on 39+ Acres and Infinity Pool Magnificent architectural gem showcases breathtaking Berkshire Mountain panoramas from nearly every room. Original hand-hewn beams and soaring ceilings with sophisticated entertaining spaces designed to maximize the spectacular sunrise vistas that define this exceptional Litchfield County estate. The thoughtfully designed main level features an open-concept great room with a living area, dining space with a wood-burning fireplace, and a well-appointed gourmet kitchen. The primary suite offers unparalleled luxury with a private porch, spa-inspired bathroom featuring a soaking tub and shower with mountain vistas, a spacious walk-in closet, and a second-floor office and den. The owner's retreat continues to the garden level with a private gym and a convenient half bath adjacent to the infinity pool area. Additional accommodations include an ensuite bedroom on the second floor and two garden-level bedrooms sharing a large recreational room and full bathroom. Outdoor living reaches its pinnacle with a heated gunite infinity lap pool with integrated hot tub, complemented by a tranquil pond. Privacy and proximity, situated just minutes from Salisbury's charming village center. Nearby amenities: :Lakeville Lake, Public Tennis, Hiking, Private & Public schools

Enjoy estate living with the convenience and ease of a shared community. Amenities include a 70ft heated pool, tennis and separate paddle/pickle courts. Owned by a noteworthy family for over 100 years, this is a rare opportunity to reside in one of Sharon's most treasured properties. The home encompasses the majority of the original mansion and was thoroughly renovated in 2013 with tasteful choices that maintain and enhance the original character. 2 wings which once surrounded a courtyard are now covered with a magnificent 3 story glass ceiling and heated for year-round use. This New Orleans style atrium is adorned with wrought iron bannisters, stenciled beams, romantic tile fountain, and antique lanterns all accentuated by an exquisite array of plants/trees. The atrium is the highlight and heart of the home, hosting many elegant dinners and weddings. The plants have been thriving for decades and can be included in a sale. There is a plant caretaker in place. 8 total bedrooms include primary bedrooms on both floors. Many of the bedrooms open to the interior balcony overlooking the atrium. One is currently used as an office; a second as a gym. 7 Full baths and 2 powder rooms. The perfectly preserved vintage Art Deco bathroom tiles & William Morris wallpapers add to the elegance. The kitchen opens to a book-lined library with fireplace & eating table. Formal dining & living rooms, allowing for extensive entertaining spaces when hosting larger groups. 7 Fireplaces in total.

This well kept Sharon, CT home is one for the ages! From the stylish interior to the beautiful grounds, this property will grow on you and never disappoint. It's the perfect blend of tranquility and convenience - nestled in a serene setting and offering a peaceful retreat with the ease of being a short stroll from the local town amenities - shops, groceries, restaurants, even hiking. The residence boasts a pristine layout with two 1st floor bedrooms, two bathrooms, a cozy basement den, a screened porch, and a spacious primary suite upstairs. The outdoor grounds are a haven of beauty with manicured gardens, a partially fenced in rear yard, a cozy fire pit area, a versatile, heatable outbuilding, and a 2 car garage. The paradox - you'll want to be outdoors when the weather is good, and you'll be happy to be indoors when it's not. Situated near prestigious schools like Hotchkiss, Salisbury, and Indian Mountain, and with recreational activities like golf, tennis, hiking, and skiing nearby, this home is an idyllic, Litchfield Hills sanctuary for anyone to enjoy.

Nestled just a stone's throw from the heart of Sharon, this delightful home is set on a picturesque one-acre parcel With its classic New England ranch-style facade, yo will be surprised by the abundant space and comfort that this residence provides. The main floor measures 2216 sf, not including a finished lower-level den that adds an additional 480 sf of living area. This property boasts 10 well-appointed rooms, ensuring ample room for relaxation and personal enjoyment. The spacious kitchen features extensive counter space that caters to both chefs and sous chefs. Step outside onto the expansive deck for outdoor dining or open the French doors from the dining room to seamlessly blend indoor and outdoor eating experiences. The living room is bathed in natural light, thanks to its large picture window. For those seeking a quiet retreat, a bookcase-lined office is conveniently situated off the living room. On the main floor, you'll find four bedrooms and two full bathrooms. The lower level is a true highlight, showcasing a native stone fireplace, a wall of windows, and direct access to the side yard. This versatile space includes a spacious workout area, laundry room, workshop, and a generously sized storage room, significantly enhancing the home's overall layout. Beyond the impressive space and prime location, the home features elegant oak flooring, beautifully curved arch doorways, and a stunning Ipe wood deck that reflect a commitment to quality craftsmanship and style.

Thoughtfully reimagined by the acclaimed firm Hendricks Churchill, this stunning 1840 mixed-use building has been fully renovated to combine timeless New England character with refined modern living. Every detail has been carefully considered-from the preserved architectural features to the stylish, contemporary finishes that elevate the space. Inside, a showroom-quality kitchen and two full bathrooms with handcrafted Fireclay tile showers showcase the home's attention to luxury and craftsmanship. The flexible layout offers endless potential for both residential and commercial use, making it ideal for entrepreneurs, creatives, or anyone seeking a unique live/work environment. Set in the center of Salisbury Village, the property enjoys a prime location just steps from local shops, dining, and services. Rear access and two off-street parking spaces provide added convenience. This is a rare opportunity to own a beautifully restored piece of Salisbury's history-modernized to meet today's standards of style and functionality.

Meet Elizabeth: placed in the heart of Salisbury, this house is all about lifestyle. Situated in the center of town, this home offers both elegance and serenity in one effortless swoop. The wraparound porch beckons you to entertain behind a distinguished evergreen hedge, ensuring ultimate privacy. Upon entering, you are immediately struck by the home's beauty and understated elegance. The living room features a wood-burning fireplace adorned with artful hand-painted tiles, flanked by built-in bookshelves-providing ample space for your book and art collection. Wide-plank floors lead you into the kitchen, which was renovated in 2016. Designed for both function and efficiency, the kitchen boasts granite countertops, Wolf propane range,hewn beams, custom linen Roman shades, and ample pantry space. Adjacent to the kitchen is a generously sized laundry room with a sink. The dining room's most defining feature is its tall tray ceiling, which adds a sense of elegance and spaciousness. A Danish fireplace framed by stones sourced from a Brownstone in Lee, MA provides the perfect remedy for chilly New England days. A separate entrance connects the home to the studio (flex space), where tall ceilings and abundant light-both natural and track-create an inspiring atmosphere. Double doors lead outside to the manageable backyard, which is partially fenced and includes a meditation labyrinth. Recently renovated and thoughtfully maintained, this house includes 3 bedrooms and 2 full baths

The key to this Hidden Charm is location, privately tucked away in a cozy area with in town access and bike path access, you have the option to venture to all the amenities offered close at hand. A cozy single level 2 bed, 1 bath, home on .67 acres has much for the owner with a vision. See the upside potential, resale value, and or rental value. Nestled in a desirable area of Salisbury, Ct. enjoy all the amenities offered. Close proximity to area private schools, 2 hours from NY City, as well as the arts and entertainment of Great Barrington, Ma. for the avid outdoors adventurist, Twin Lakes Marina, Hiking and Fishing is an outdoor weekend delight!

Experience the convenience of playing golf at home on your .083 acre of land with views of the Connecticut and New York mountain ranges, surrounded by apple trees and away from city life. This ranch-style home features on the main floor: three bedrooms including a primary bedroom with full bathroom, powder room, laundry room, built-in 2-car garage, kitchen with designer 42-inch white cabinetry, granite countertops, all stainless steel appliances, and a center island with breakfast nook adorned with pendants. The home has been recently remodeled and offers an open concept layout with sliding doors leading to balconies, two wood-burning fireplaces accented by brick walls, HVAC, recessed lighting, and hardwood floors throughout the main floor. The lower level includes a full bathroom, luxury vinyl planks throughout, family room, recreational room, and sliding doors leading to the patio area. Sharon Connecticut has everything needed to have a pleasant & serene life style and much more.

Meticulously designed modern farmhouse set on 10.70 acres along one of Litchfield County's picaresque roads, featuring stunning views over protected land. This 2,880 sq ft light-filled home showcases natural materials and timeless architecture with an open floor plan organized around a commanding two-sided granite curbstone fireplace that unites the living room and chef's kitchen. The residence features white oak wide-board floors throughout, custom cabinetry, butcher block and honed Carrera marble countertops, five-burner cooktop, and large sheets of glass that eliminate barriers between indoors and out. The thoughtful layout includes an office/bedroom and half bath on the main level, with additional bedrooms including a primary suite with clawfoot tub upstairs - all finished with enameled wood floors and quality finishes.The property's historic character is enhanced by an 1880's three-bedroom, two-bath homestead with an artist studio, complemented by two long barns and a pair of distinctive silos. The impressive main 160'x40' barn has been transformed into an entertainment space with exposed trusses, polished concrete floors, private office area, and open workspace - all fully heated and cooled for year-round enjoyment. Conveniently located near Lakeville, Salisbury, Hotchkiss, Indian Mountain School, and Millerton with easy access to Metro-North trains. Conservation easement with Salisbury Land Trust ensures the preservation of this exceptional property's natural beauty.