Magnificent Spacious Colonial with Rocking Chair Front Porch. Slider off Dining Room over looking Large Deck with Retractable Awning. This is a Impressive 2.21 Level Property. This Beautiful Home is on a Cul-De-Sac. This Rare Find Home with Central Air has a lot to offer. This 3 Bedrooms,, Eat In Kitchen, Large Living Room, Family Room and Full Finish Basement is 20 x 20. Garage and a shed and so much more. New Roof, Washer and Dryer n 2024, New Oil Tank and Water Softer in 2026. Near Rte 84. Minutes to R/R.
Well maintained raised ranch offering 4 bedrooms and 2 bathrooms. This inviting home features spacious bedrooms, hardwood floors, and a bright living room filled with natural light. The finished lower level provides additional living space and laundry room, perfect for guests, a home office, or recreation. Sliding doors from the dining room lead to a deck overlooking a spacious backyard, ideal for entertaining and outdoor activities. Conveniently located right by the beautiful Whaley Lake, where you can enjoy private beaches, fishing, swimming, kayaking, boating, and motor boats are allowed. Just minutes from the charming Town of Pawling, with easy access to dining, shopping, Metro north train station, Thunder Ridge Ski Area, Trails to Walk, Bike or Hike. A wonderful opportunity to enjoy both comfort and outdoor living!
Welcome to 6 Martingale Way, an impressive 4-bedroom, 3.5-bathroom colonial offering nearly 4,700 square feet of living space in the highly sought-after Highlands community of Pawling, NY. From the moment you step inside, you'll be greeted by beautifully refinished hardwood floors that flow throughout the entire first floor, setting the tone for the quality and care found throughout this exceptional home. The main level features a spacious eat-in kitchen, a formal dining room perfect for entertaining, a warm and inviting living room with sky-high vaulted ceilings, a wood-burning fireplace, a generous family room, and a truly unique sunken bonus room bathed in natural light from its stunning skylights. Off the kitchen and through the French doors, you'll find a large screened in porch leading to an expansive deck - perfect for summer grilling! The finished basement expands your living options even further, offering a 6-seater wet bar, walk-out access through sliding glass doors, abundant natural light, and a dedicated gym, a rare and versatile space ideal for recreation, work, or relaxation. Upstairs, the carpeted second floor is home to a massive primary suite that serves as a true retreat, complemented by three additional well-appointed bedrooms and a hall bathroom featuring dual sinks. Whether you're hosting guests or growing into the space, this home delivers the room and flexibility to do it all. Set within The Highlands, a beautifully maintained community complete with a sparkling in-ground pool and tennis courts, residents enjoy a lifestyle that blends suburban comfort with resort-style amenities. The home is serviced by public water and sewer for added convenience and peace of mind. Located just minutes from grocery stores, the charming Village of Pawling, vibrant local dining, and the Pawling Metro-North train station, with NYC less than two hours away, this is the perfect home for those seeking a serene escape without sacrificing connectivity. 6 Martingale Way is a rare opportunity; don't miss your chance to call The Highlands home!
Welcome to 978 W Dover Road in Pawling, NY—where comfort, space, and scenic beauty come together effortlessly. This inviting home features 3 generously sized bedrooms, 3 full bathrooms, and a dedicated home office, making remote work both productive and enjoyable. The open-concept main level creates a seamless flow between living spaces, perfect for hosting gatherings or simply spending quality time together. The finished basement, complete with a full bath, offers incredible flexibility—whether you envision a recreation area or private workspace, the possibilities are endless. Step outside and take in the stunning mountain views. The expansive back deck stretches the length of the home, providing the perfect setting for outdoor entertaining, while the fire pit adds a cozy, magical touch to evenings under the stars. Conveniently located just minutes from Metro-North, Route 22, local shops, restaurants, and schools, this home strikes the ideal balance between accessibility and tranquility. Enjoy nearby hiking trails, rail trails, and a wide range of outdoor activities—all right at your doorstep. A perfect blend of modern convenience and natural beauty awaits you here.
Fantastic weekend getaway or full time residence, hard to find Quaker Hill, situated on 5.00 secluded acres with babbling brook running through. Master bedroom with bath, walk in closet. 2 additional bedrooms & full bath. The living room, dining area & eat in kitchen are bright & spacious with hardwood floors throughout. Finished walkout basement with powder room. This property is mostly level, there is a storage shed. Room for expansion on this beautiful land. Only 90 minutes to NYC, close to trains and shops.
Tucked away on historic Quaker Hill - known for its picturesque horse farms and country estates - you will find this charming lodge-style home, offering a comfortable blend of character and rustic warmth. The 10.23 acre property is approached by a winding, level driveway that gently opens to a nature lovers dream. At the heart of the home lies an impressive great room, where a soaring stone fireplace, gleaming hardwood floors, and a sunlit bay window create an inviting atmosphere for both relaxed living and gatherings. The open-concept dining area is bright and airy, enhanced by French doors that open to a free-form, wrap-around deck. All rooms offer beautiful views of the tranquil landscape, lightly wooded property and neighboring horse pasture. Step out of the kitchen to a huge, wrap-around covered porch! First floor bedroom offers a walk-in closet and book shelves. Also on the first floor is a full bath, and a den accented by wide board floors. Upstairs, the primary suite features a private balcony, soaring ceiling, walk-in closet, and a full bath with a jetted tub. Full of natural light, a loft-style sitting room or home office overlooks the great room below. Whole house generator is another great feature! A rare offering on Quaker Hill, this property combines authentic lodge character, rustic charm. This home enjoys the beauty and privacy of country living—all within reach of the area’s equestrian trails, scenic vistas, golf course, more. The Village of Pawling is lovely, only 10 minutes away! You will discover great restaurants, bakeries, fun pubs, shops, library and Metro-North, Harlem Line.
Super Charming Cape On An Ultra Private 2.92 Acres At The Very End Of The Dead End Street! Close To Everything -- Shopping, Schools, Train Station/Commuting, Restaurants And Still Be Tucked Into Your Own Private Haven. Flexible Floor Plan To Create Rooms For You --- Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side. Current Owners Created His & Hers Living Rooms. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Ready For Your Ideas Without Having To Start With Unfinished Space. Very Flexible Space! Both Bedrooms In The Upper Level Are Very Large and The House Has Room To Grow As Your Spatial Needs Grows -- Bedroom On The Left Has 2 Very Deep Areas Currently Unfinished But Being Used As 2 Walk-In Closets. However, When It's Time To Grow Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Summers Are The Best While Enjoying The South Facing Deck Off The Kitchen That Leads To The In-Ground Pool In The Backyard. Excited To Host Summer BBQs & Pool Parties? You Could Pack + or -- 50 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, A Camper / RV, OR For Those Fantastic Summer Parties! To The Left Of The House Included As Part Of The <3 Acres, Is 1 Acre Of Land That Is Part Of The Privacy. It Could Be Turned Into An Additional Detached Garages, Cute Cottage To Rent Full or Part Time (Abnb) or House an In-Law, A Garden With A Garden Potting Shed, A Work Shop, Or Whatever Your Vision Can Imagine. Cozy Up To The Fire In The Winter OR The Summer's Sun & Moon's Reflection From The Pool As You Enjoy Your Morning Coffee & Your Evening's Glass Of Wine. Come! Relax, Unwind, & Enjoy Life!
Properties like this don't come along often! As you turn off the road, the world quiets. The driveway pulls you back through a canopy of mature trees, and by the time the house appears, you already feel the privacy with over five acres, buffered on all sides, thoughtfully expanded and upgraded far beyond its 1975 origins. Step inside to a living room anchored by a stone fireplace, original hardwood floors, and warm, inviting walls. As you keep going, the formal dining room opens up with vaulted ceilings and large exposed wooden beams built for long dinners and easy conversation. Then you reach the kitchen, and you stop. Cherry cabinetry, stone countertops, a center island and at the heart of it all, a professional Garland gas range with six burners, a 24" raised griddle, broiler, and two full ovens. A large walk-in pantry keeps everything within reach. This kitchen was built to match your food-inspired ambition. Down the hall, two bedrooms with sizeable closets and a full bathroom lead you to the primary suite. This space features soaring ceilings, hardwood floors, a primary bath with a freestanding copper soaking tub, a glass-enclosed tiled shower, and a custom walk-in closet with built-ins for two. The lower level offers a gym with shock-absorbing flooring and its own shower bath, a home office, an original wood stove, laundry, and finished flex space including a bar room ready for entertaining. Outside, 26 owned solar panels keep electricity costs between $0–$150/month. A three-car garage sits steps away, a whole-home generator has you covered, and a 2,400 SF steel barn on the southwest corner opens up possibilities as wide as the land itself. Minutes from the Village of Pawling and Metro-North, this is country living without compromise.
**Highest & Best 7pm Monday 4/27.** Set on nearly three private acres just minutes from Metro-North, this fully renovated country retreat delivers the space, privacy, and lifestyle buyers are searching for right now. Bright, open, and thoughtfully updated, the home is designed for both everyday living and easy entertaining. The kitchen features custom cabinetry, quartz countertops, and stainless steel appliances, flowing directly into the main living space anchored by a stone fireplace. Large windows and sliding doors open to a spacious deck overlooking the property. All three bedrooms and three full bathrooms are located on the main level, including a primary suite. The walk-out lower level offers additional flexible space with a full bath, ideal for a media room, guest space, or home office. Outside, a 900 sq ft covered patio creates a true indoor-outdoor living setup. The detached barn-style garage includes a 965 sq ft loft above, perfect for a studio, gym, or future expansion. Located minutes to Pawling Village, Metro-North, the Appalachian Trail, and local nature preserves, this is a turnkey country property with real flexibility and long-term upside.
Rare 5-Acre Quaker Hill Estate with Guest Cottage: Discover the ultimate sanctuary at the crest of Quaker Hill, where 43 Meeting House Road stands as a testament to refined country living. Situated on a lush 5-acre parcel and set well back from a scenic country road, this estate offers a rare degree of privacy and tranquility, surrounded by sweeping meadows, historic horse farms and prestigious neighboring estates. Originally a log home, the property has been masterly reimagined for the luxury buyer into an elegant, warmly welcoming residence where fine architectural details and high-end finishes are evident at every turn. The main residence is a study in sophisticated design, anchored by wide-plank oak flooring that flows through the living room, sunroom and commanding library-style study. At the heart of the home, a modern chef’s kitchen with radient heated floors, and a generous central island that serve as the perfect stage for both grand entertaining and quiet dinners. A striking steel-clad stairwell leads to the upper level, where the primary suite serves as a private retreat with soaring 18-ft ceilings, skylights, and a Juliet balcony that overlooks a picturesque landscape of mature plantings and rolling hills. Two additional bedrooms with full baths and a large dressing room, a possible fourth bedroom, complete this level. The lifestyle extends seamlessly outdoors, where a wraparound deck overlooks a serene, spring-fed pond. For summer entertaining, a separate deck surrounds a tranquil pool area, fully equipped with a bar, cabana and bathroom. Beyond its aesthetic beauty, the home is engineered for effortless living with a heated 2-car garage, whole-house generator, central vacuum, and integrated security and Sonos systems. Complementing the main house is a charming totally separate two-bedroom guest cottage built in 1920. Fully renovated with its own full kitchen, wood burning fireplace, full bath and lofted living space, utilities, and septic system, it offers a private haven for visitors, a dedicated professional workspace or caretaker's residence. The house has state of the art wi-fi, heating and cooling systems, and an Aprilaire full-house dehumidifier that is integrated with the HVAC system. Heat coils on the gutters and parts of the roof protect the home from ice-dams. Every detail has been attended to that makes this home a true treasure. Located just minutes from the historic Village of Pawling, and under 90 minutes to Manhattan via Metro-North, this property represents the pinnacle of the Quaker Hill lifestyle—a perfect weekend retreat or a permanent paradise.
Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct access to the OTA. The stunning equine compound is presided over by a circa 1860 main estate, masterfully renovated boasting 3,942 SF, 4 bedrooms, 4 bathrooms, 9 rooms, with an in-ground pool. Designed for year-round riding, training, and boarding indoors and out. With barns, indoor and outdoor rings all developed for the unique training needs for dressage, hunter-jumper, and polo. The main barn has 32 12' x12' stalls, center aisle, matted stalls, yoked windows, fire suppression system, automatic fly control system, climate-controlled tack room with kitchen and bathroom, feed storage, office and viewing room, bathrooms, 2 hot water wash stalls with heat lamps, 4 grooming stalls, hay loft with drop to each stall, and hay conveyor. An attached 200' x 90' indoor riding ring with equestrian sand with fiber footing, sound system, and retractable windows. Adjacent to the indoor, a 220' x 100' outdoor jumping ring and a 200' x 80' outdoor dressage ring. The second largest barn has 27 12' x 12'stalls, with a 200' x 90' indoor riding ring, and a 220' x 100' outdoor jumping ring with TraveLite dust free footings. The polo barn has 14 10' x 14' yoked stalls. The pony barn has 8 10' x 12' stalls and a fire suppression system. Buildings and additional structures on the property include a gated entry and guard house, manager's house, and a renovated barn, now a stylish clubhouse, which can accommodate up to 60 people with a fireplace, full kitchen and bathrooms, a 2-bedroom apartment above and a manager's office attached. A 3-bedroom, 4 bath cape cod guest house with tennis/basketball court. 3 1-bedroom guest cottages with thatched roofs. Groom quarters, equipment barn, fire suppression building with a 50,000 gallon underground water detention tank. Automatic hot-walker for horse conditioning. Wedding barn to host special events, 15 events a year, up to 120 guests. Boma outdoor BBQ area, skeet and trap range and helipad. For those looking to build another unparalleled estate, a homesite foundation exists with an infinity edge pool with the most sublime views. Additional features include 3 ponds on the property, judges and viewing gazebos, 2-week hay storage, irrigation systems, 3 generators, 7 wells, 7 septics, and 1 fire hydrant. Two parcels, 76-acres and 171-acres create this pastoral perfection in the heart of the Hudson Valley. This premier equestrian venue presents a truly remarkable opportunity just minutes to the Village of Pawling, a quaint upstate, bucolic 18th century village. The charming village offers fine dining, fun eateries, boutique shops, antique stores, cultural attractions and a seasonal farmer's market. Pawling has its very own Metro North station stop, just 90 minutes by train or car to NYC.
Nestled in the heart of historic Quaker Hill, this bucolic property offers timeless charm just a stone’s throw from the iconic Meeting House. Originally built in 1983, the home underwent a meticulous, top-to-bottom renovation in 2016, thoughtfully upgrading all major systems, finishes, and living spaces to modern standards while preserving its serene setting. The residence is exceptionally well-equipped with advanced infrastructure and comfort-driven features, including a state-of-the-art geothermal heating and cooling system, whole-house fresh air circulation, and spray foam insulation for optimal efficiency. Bathrooms are appointed with underfloor radiant heat, while a snow melt system beneath the front entry ensures year-round access. Additional highlights include a central vacuum system, laundry chute, fully finished basement, and a 60-amp EV charging station. Designed for both resilience and luxury, the property features a 100kW whole-house emergency generator powered by two buried propane tanks (1,000 and 500 gallons). Outdoors, a stunning infinity-edge in-ground pool overlooks the west-facing rear of the property, capturing breathtaking sunsets and enhancing the home’s tranquil, pastoral setting. A rare opportunity to own a thoughtfully modernized home in one of the region’s most storied and picturesque locations.
This great 2 bedroom 2.5 bath townhome is a must see. Many great amenities including attached garage, formal dining room, fireplace, rear deck and more. This is a Fannie Mae HomePath property.
~ Welcome to your spacious and cozy tri-level townhome in the desirable Cedar Valley Community. ~ This rare end unit provides you with an abundance of light and additional outdoor space. Featuring 2 spacious bedrooms and 2.5 bathrooms, this home boasts an open and versatile layout ideal for everyday living and entertaining. The dining area and bright living room with its cozy fireplace opens onto a generous first-floor deck that overlooks a private yard with room for outdoor activities and a view of beautiful natural surroundings. A half-bath is conveniently located on the main floor. On the second floor are two spacious bedrooms and a convenient laundry area which eliminates the need to carry heavy loads of laundry up and down stairs. The primary bedroom features a large closet and a renovated bathroom. The finished basement offers a versatile space that is ideal for a family room, home office, gym, or guest area. It also provides access to the patio thus further extending your sense of space. There is ample storage space throughout the entire home. ~ The perfect blend of comfort, functionality, and low-maintenance living. ~ Enjoy the privacy of your own home without the responsibility of doing outdoor maintenance. The low $400 monthly Association Fee includes a community pool, tennis courts, clubhouse, water, trash/snow removal, and lawn/road maintenance. Just minutes from Pawling Village and all its amenities: restaurants, shops, Farmer’s Market, professional services and Metro North. With easy access to major highways you can easily enjoy golfing, skiing and fishing. Whether you are looking for a full-time residence or a weekend escape, this townhouse is ideally located and full of potential.
Step into the year our nation was born and own a piece of living American history. Originally constructed in 1776 by a Scottish stone mason and frontiersman, who fought in two Revolutionary War battles, this enduring stone home is more than a residence; it’s a survivor. Once known as the Pawling Toll Gate and Toll House, it served as a gateway for travelers, a general store, a post office, and a gathering place woven into the early fabric of the region. Inside, the home carries its history with quiet strength. Hand-hewn beams stretch across the ceilings. Deep-set windows draw in southern light. Original fireplaces, now fitted with wood stove inserts, anchor the space. Wide-plank wood floors, laid in defiance of British colonial restrictions, remain underfoot, worn smooth by time, not replaced. The home offers 2 bedrooms and 2 full baths, with a layout that is both grounded and adaptable. The lower level provides a private, flexible space, ideal for a studio, retreat, or guest quarters. Outside, 2.2 acres open directly to the Empire State Trail and offer immediate access to the Appalachian Trail, putting miles of riding, hiking, and exploration right at your doorstep. This isn’t nearby, it’s connected. Behind the home, a substantial ~1,000 sq ft detached garage provides space for four or more vehicles, along with room for equipment, workshop use, or future conversion. It’s not an afterthought, it’s an asset. Located just minutes from the village of Pawling, Metro-North, shops, and dining, the property balances seclusion with accessibility. This is not just a home, it’s a piece of early American infrastructure that has endured, adapted, and remained. Built by hand, shaped by history, and still standing with purpose.
Welcome to your forever home, serene retreat and mini estate. Enjoy the 88 private acres with breath taking views. Mother Nature is at her best. Exceptional beauty for all four seasons. The unique and exquisite architectural design of this home lends to expansive living space, tucked behind gated entry. This home offers expansive living space, luxury and customize finishes throughout. A true combination of peaceful, comfortable living, spacious floor plan. Spanning approximately 6625 square feet, this custom-built home features 6 spacious bedrooms and 6 1/2 bathrooms, plus a 3-car attached garage with office, and or studio apartment above. A large grand foyer instantly feels like home. Its high ceilings, Brazilian cherry floors, glass walls lead you through sun-filled, open-concept living areas. The custom kitchen is a culinary dream, spacious design with the chef in mind. Top-of-the-line appliances, and custom cabinetry. Generous island perfect for casual meals or use the adjacent dining room for entertaining. Manicured grounds. Enjoy the beautiful in-ground pool, or the newly built Brazilian Ipe deck, lush landscaping and fenced-in privacy. The property also features newly renovated separate living quarters with walk-out entrance, French doors. Custom laundry room area, and even a-dog wash station — ideal for in-laws, guests, or animal lovers. Set back on the property is a fully powered structure equipped with electricity. Ideal for a workshop, home office, gym, or a creative studio. It offers the perfect blend of utility and solitude for any enthusiast. Direct access to scenic Adirondack trails for walking, biking, or horseback. Minutes from town, eateries, shops, and trains, this property has the perfect balance of convenience and seclusion. Whether you're hosting gatherings or seeking a peaceful escape, this extraordinary estate offers the lifestyle you've been dreaming of.
Fall in Love with this Charming Mediterranean Style Garden Home. A Private Oasis Hidden Away and Nestled among a Grove of Mature Trees. Follow meandering paths that lead to Splashes of Color from the Cultivated Perennial Gardens of a Lifetime and a Gentle Woodland Stream. This Home is Sparkling Clean, Freshly Polished, Newly Painted, Move-In Ready and awaits your Arrival. Tucked in at the end of a small Cul-de-Sac, this home is Convenient to the Lovely and Walkable town of Pawling, but Peaceful and a World Away... This home affords Living on one Level, with open areas leading to very Large Rooms. Enjoy Romantic Evenings by your Wood Burning Fireplace, surrounded by your favorite books. Entertain and Dine in your Large Living and Dining Rooms with Views of the Gardens through your two oversized Bay Windows. Downstairs, Double your Living Space with a Cozy Finished Basement that contains a second Full Bath, Rooms to Work, Relax, Exercise and Entertain. This Special Home is yours, with a 10 minute walk to the Metro-North Train Station, Wonderful Restaurants, Coffee Shops & Bakeries, Eclectic Shoppes and the Amazing Full Service Pia Anthony Salon. Nearby enjoy Concerts at the Exclusive Trinity Pawling School, Famous Music Venue of Daryl's House, Paddle through the Great Swamp by Kayak or Canoe, Ski down nearby Thunder Ridge Mountain, Join the Pawling Mountain Club, Hike the Appalachian Trail or find the Equestrian Pursuit of your choice. Pawling is a wonderful place to explore natural surroundings and live in your very own Private Retreat.
You finally have the opportunity to own a home with year-round mountain views set on an expansive property. A place where you can bring your vision to life and transform the space into a true masterpiece. 128 Old Pawling Road is a beautifully positioned property in Pawling, NY, offering a rare combination of scenic views, generous land, and the potential to create a truly special home. Set back from the road, the home is approached by a long private driveway and gated entrance, offering a sense of privacy while still being part of a neighborhood setting. Resting on over 5 acres, the property showcases stunning mountain views that create an impressive backdrop to everyday living year-round. Whether you’re relaxing on the porch, entertaining outdoors, or simply enjoying the peace of nature, the landscape makes for a desired full-time residence or weekend escape. Conveniently located near Pawling village, Metro-North, local shops, dining, and outdoor recreation like the Appalachian trail and ski , this home combines comfort, space, and natural beauty with everyday practicality. Discover the charm and views that make 128 Old Pawling Road a standout opportunity in the Hudson Valley.
Be the first to live in this stunning four bedroom, two and a half bath home nestled on a beautiful two and a half acre lot. This home is located on the border of Putnam and Duchess counties. Step onto the full length front porch and inside to a light, bright and airy interior boasting a modern open floor plan. Spacious entrance foyer with double coat closets and sleek iron railing staircase with motion sensor lighting. Formal living and dining rooms. Family room with built in electric fireplace and niche to install your flat screen tv. Enjoy the Chefs kitchen with quartz countertops, stainless steel appliances, induction cook top, built in wall oven and microwave, farmhouse sink, hidden backsplash outlets, pantry cabinets and large center island perfect for entertaining. Step outside from the oversized 12 ft wide European slider to the large patio ideal for relaxing while enjoy the gorgeous views and yard. First floor lavatory. The spacious primary bedroom is your personal retreat with a tray ceiling, walk in closet and primary bath with a custom tile shower, soaking tub, double sinks and vanity with smart mirrors, toilet and radiant heated bathroom floor. The three additional bedrooms offer plenty of space with large closets and natural light. Center hall full bath with double sinks, smart mirrors, tiled tub and heated flooring. The convenience of a second floor laundry room makes daily chores a breeze. The second story offers a five hundred square foot bonus room perfect for playroom, home office or gym. Hardwood floors throughout. The full basement and attic has endless storage or expansion possibilities. Built to last with a high-efficiency HVAC system, smart programable wifi thermostats and spray foam insulation for year round comfort. Still time to customize the hardwood floor stain color, closets and shower doors. This home is a rare gem that checks every box. Just minutes from major highways and train. Small town charm complete with a farmers market. The property offers the ideal combination of seclusion and accessibility. Don't miss your chance to own this private oasis. Schedule your private showing today!
Welcome to Woodland Waters. Offered for the first time, this private estate is a secluded sanctuary where luxury and nature exist in perfect harmony. Over the course of five decades, the same owner has shaped and nurtured the property with remarkable care and attention, creating a setting that embodies both artistry and authenticity. With its vast landholdings, exceptional lifestyle offerings, it is a once-in-a-lifetime opportunity. Nestled in the heart of nature, this extraordinary private estate spans nearly 1,338 acres, offering unparalleled seclusion, natural beauty, and world-class amenities. Designed as a one-of-a-kind sanctuary, the retreat spans 23 tax lots and showcases breathtaking landscapes, luxurious accommodations, and distinctive architectural elements that blend seamlessly with the surrounding environment. The estate is best described with three large property zones. The Garden Parcel, with 17 lots and seven residences, totaling 751.51 acres, forms the centerpiece of the property. Purgatory Hill encompasses three lots and three residences across 337.61 acres. The Northwest Territory offers 248.63 acres of unspoiled vacant land across three lots. Together, these parcels create an estate of remarkable scale and diversity. balancing residential, recreational, and natural elements. At the heart of the Garden Parcel rises the 55,000-square-foot main residence-an architectural masterpiece surrounded by six additional homes. Within its walls are nine bedrooms, nine full baths, six half baths, and twenty fireplaces, each space crafted with extraordinary attention to detail. The grounds embrace the spirit of the Appalachian Trail, with native plantings and curated landscapes creating a harmonious environment. This grand residence is as functional as it is breathtaking. Designed for both everyday living and exceptional entertaining, it features an indoor pool and spa framed by the surrounding natural landscape, expansive gathering spaces, and an indoor basketball court complete with locker rooms. Two secure, climate-controlled art storage areas further reflect the home's thoughtful design and attention to detail. Complementing the main residence, the Garden Parcel also features a meticulously maintained 6,000-square-foot guest house with its own pool. Artfully designed, the Tea House further enhances the parcel, offering a peaceful space for both reflection and intimate gatherings. Over 20 miles of interior roads and trails wind through the landscape, inviting exploration by foot, bike, or vehicle. Comprehensive maps detail the extensive network of roads, streams, ponds, and structures. Anchoring the operational side of the estate, the Office Complex features a four-bay machine barn with a lift and wash pad, a multilevel office building, and a dedicated security outpost. This infrastructure ensures seamless management of the property's extensive resources. Beyond its natural beauty, this estate embodies versatility, solitude, and enduring grace - a true legacy property unlike any other in the Hudson Valley. Thoughtfully curated down to its meticulously appointed landscape, Woodland Waters now awaits its next steward to cherish and preserve for generations to come.
New construction 4 bedroom, 4.5 bathroom home on 5 acres. Don't miss this opportunity to customize your dream home. This home features a open floor plan with large kitchen, perfect for entertaining. The main living area has exposed beams and high ceilings. The primary bedroom has large walk in closet and ensuite. There is also a junior suite with ensuite. See attached floor plans for full detail. Great location, close to town of pawling, train station, dining and more! Pictures shown are from previous new builds to show style of home with exposed beams, etc.
Welcome to this newly renovated home in the Village of Pawling! Walk up to the large wrap around deck (grill-ready for the summer) to the front door, offering bright open living space with fresh hardwood floors and split system air heat and cooling. The kitchen is equipped with new stainless-steel appliances and shiny granite countertops. Additionally, the main floor offers an updated full bathroom and laundry area. The second floor extends to three bedrooms with gleaming hardwood floors and split air units in each. The Village sidewalk ends right outside your door making Pawling boutique stores, restaurants and Metro-North extra convenient. Minutes to route 22, route 55, 84 and 684.
Welcome home to this Majestic Quaker Hill Colonial. Perfectly nestled on a private level parcel complete with mature trees, fieldstone walls, tranquil pond and an exquisite 24'x36'post & beam barn constructed in 2016. The house itself features a rocking chair covered porch, oversized mahogany back deck, 3 car attached garage and circular driveway. Once inside there's plenty of room to roam with over 4000 square feet of hardwood and tiled floors. The 1st floor boasts a huge kitchen with granite tops, SS appliances, pantry, mud/laundry room, powder room, formal dining room, family room and an open living room complete with fireplace, crown moldings and views of the private back yard. Adjacent to the living room is a private en suite with French doors allowing access to the spacious back deck. Moving upstairs you will find generously sized bedrooms, California closets, primary bath, hall bath, a library/sitting room and an oversized home office with a fireplace & an abundance of natural light. Moving upstairs once again to the 3rd floor you will be greeted by over 600 square feet of plushy carpeted media room perfect for entertaining or perhaps a night of theater. Other amenities include security system, heated garage with high ceilings, 2 year old boiler, recessed lighting, tiled backsplashes, fenced in garden with raised beds, dog pens and more. All this just minutes to the quaint Village of Pawling with charming boutique shops, eateries, a pub and the Pawling Metro North Train Station. Close to Thunder Ridge Ski Resort, Cranberry Mountain Preserve/Hiking and just 90 minutes to NYC by car or train. Come take a look, this property has it all!
A/O Home Inspection has been done -First time ever on the market! This 4-bedroom, 2 full bath home is located just minutes from the Village of Pawling and literally 1 minute from Route 22. This family built this home in 1960, raising their family here since then. That alone said something about this home and location. Very well-maintained neighborhood on a dead-end street. Home is a ranch style home of 1768 Sq Ft of Living Space. Living room has a cozy fireplace and Dining Room is right off the kitchen. It has a beautiful family room to hang in and right off that is a screen in porch that leads to a level .34 back yard. Full Bath in Main hallway and primary bedroom. Large unfinished Basement area is off of the 1 car garage that would make a beautiful playroom/workout room/man's cave/workshop. Home is a solid home looking for that next family. Minutes to Metro North - 1 1/2 hrs to NYC
Fantastic Whaley Lake raised ranch home with LAKE RIGHTS and FULL ACCESS to the only motorized lake in Dutchess County! Embrace year round, lake community living in this bright, roomy, meticulously maintained, 4 bedroom, 1 1/2 bath home. Scenic view of the lake from a spacious deck off the dining room, great for summer entertaining! With a 120ft. of lakeside road frontage there is also plenty of space in the yard to build and enjoy a fire pit! The walk-out, lower level offers an additional 450 sqft. of finished living which includes the fourth bedroom and half bath. This home has almost no wear and tear. You can move right in, get comfortable and update down the road. Only ten minutes to everything the charming Village of Pawling has to offer, including Lakeside Park for year-round recreational activities, pickleball and summer concerts. Metro-North is available with stations at Pawling and Southeast for a 90 minute commute to NYC. This home is in the Pawling Central School District. Hudson Valley and lake life at its best!

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Pawling is located in New York. Pawling, New York has a population of 8,024. Pawling is more family-centric than the surrounding county with 33.87% of the households containing married families with children. The county average for households married with children is 29.92%.
The median household income in Pawling, New York is $106,806. The median household income for the surrounding county is $87,112 compared to the national median of $69,021. The median age of people living in Pawling is 47.9 years.
The average high temperature in July is 81.5 degrees, with an average low temperature in January of 16.3 degrees. The average rainfall is approximately 49.5 inches per year, with 49.1 inches of snow per year.