Courtesy: Julia B Fee Sothebys Int. Rlty
914-234-0200
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 family 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 family 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 Japanese 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.
Courtesy: AI Realty Brokerage LLC
914-346-7674
Welcome to 2 Bridle Way, a rare opportunity to own a spacious 3-bedroom, 3.5-bath Colonial in one of Pawling’s most desirable and well-kept communities. Built in 1992, this young home offers an impressive layout with generous room sizes, abundant natural light, and endless potential for the next owner to bring their vision to life. Located in a sought-after HOA neighborhood, residents enjoy the convenience of included water, sewer, and professional landscaping services, creating a low-maintenance lifestyle with exceptional value. The main level features a traditional Colonial flow with ample living and dining space, while the upper level offers well-proportioned bedrooms, including a primary suite with its own bathroom. The full walk-out basement provides additional square footage ready to be finished—ideal for a family room, home office, gym, or guest area. This property does require updates and renovation, making it the perfect canvas for a buyer looking to customize a home to their personal taste or for an investor seeking a project with strong upside potential. Homes in this community are highly sought after, and opportunities like this do not come around often. Priced aggressively for a quick sale. Bring your vision and creativity—this home will not last!
Courtesy: McGrath Realty Inc
845-855-5550
Welcome to Country Living at Its Finest! Nestled on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential for those looking to restore a piece of history. A long, tree-lined driveway leads to this charming 4-bedroom, 4-bath home surrounded by open fields, mature trees, and peaceful country views. The property features a spacious 4-car garage with finished living space with Full bathroom bathroom above. Inside, the home retains much of its original character, with hardwood floors throughout, crown molding, and hidden staircases adding to its timeless charm. The inviting entry opens to a quiet library or office with a fireplace, a sunroom with two walls of windows overlooking the yard and patio, and a spacious living room anchored by a second fireplace. The large dining room, wrapped in glass and hardwood floors, is perfect for gatherings, while the kitchen awaits your personal touch. Upstairs, three bedrooms each offer unique character, while the large primary suite features hardwood floors, its own private staircase, a generous bath, and ample closet space. With room for horses, gardens, or simply relaxing in the peace and beauty of nature, this property offers the perfect blend of privacy, potential, and old-world charm.
Courtesy: McGrath Realty Inc
845-855-5550
Welcome to 16 Townsend Blvd, a lovely brick home set in the heart of picturesque Pawling, NY. On the end of a quiet, dead-end road, within walking distance of the historic Village of Pawling, this charming domicile will not last long. The Village of Pawling is home to the oldest public-golf course in the United States, George Washington's headquarters during the Revolutionary War, ample eateries and cafes, salons, shoppes, recreational parks, exceptional public and private schools, and more. The Metro North Train Station is a short meander away. The lawn is flat and lush and easily maintained. Bilco-doors make basement access easy and efficient and afford ample space to expand the living square footage of the house. The oil tank is brand-new and the house is freshly painted. Come check out this wonderful property and see what the neighborhood has to offer.
Courtesy: YourHomeSold Guaranteed Realty
718-324-6060
Welcome to 21 Kings Way, a charming 3-bedroom, 2.5-bathroom townhome nestled in a wonderful community in Pawling, NY. This beautifully maintained home offers a perfect blend of comfort, style, and convenience. Step inside to discover an inviting open floor plan with spacious living areas, perfect for both entertaining and everyday living. The large windows flood the space with natural light, creating a warm and welcoming atmosphere. The modern kitchen features updated appliances, ample cabinet space, and a breakfast bar that opens to the dining area — making it ideal for both meals and dinner parties. The master suite is a peaceful retreat, complete with a private en-suite bathroom and generous closet space. Two additional bedrooms provide plenty of room for guests, or a home office. The full and half bathrooms are beautifully designed, offering modern fixtures and finishes. Outside, enjoy a private patio — perfect for morning coffee, evening relaxation, or a small garden. The home is part of a well-maintained community, offering a sense of peace and privacy while still being close to shopping, dining, and recreational activities. With easy access to highways, commuting is a breeze. Don’t miss the opportunity to make this lovely townhome your own. Schedule a showing today!
Courtesy: Christie's Int. Real Estate
914-266-9200
A Bucolic Retreat in Prestigious Quaker Hill, nestled among grand equestrian estates in the coveted Quaker Hill community of Pawling, this magnificent country retreat artfully blends modern luxury with rustic charm. Set on five serene acres surrounded by rolling meadows, scenic horse farms, and distinguished country homes, 43 Meeting House Lane offers an inspiring escape that celebrates the best of Hudson Valley living. The property features a fully renovated three-bedroom main residence and a charming two-bedroom guest cottage, each with its own utilities—ideal for hosting guests, accommodating extended family, or providing a caretaker’s residence. Originally conceived as a classic log home, the main residence has been brilliantly transformed into an Art Deco-inspired haven, merging rustic warmth with sophisticated design. Inside, the home flows effortlessly from a modern chef’s kitchen to a banquet-sized dining area perfect for grand entertaining or intimate gatherings. Wide-plank oak floors, a steel-clad stairwell, and distinctive architectural details add character throughout. The primary suite impresses with vaulted 18 foot ceilings, skylights, and a private balcony overlooking the tranquil and lush grounds. Additional highlights include a sunroom, generously sized bedrooms, and a versatile library or office where the current owner once found inspiration to write several celebrated television shows. Step outside to discover your own private oasis. A wraparound deck overlooks the spring-fed pond, while the pool area, complete with an outdoor bar, cabana, and bathroom, sets the scene for relaxation and recreation. Whether enjoying morning coffee on the deck or sunset gatherings by the water, every vantage point frames the beauty of the property’s pastoral landscape. Equestrian possibilities abound, with ample acreage for paddocks or a small barn. Additional amenities include a heated two-car garage, whole-house generator, central vacuum, and integrated security and Sonos audio systems. Perfect as a full-time residence or weekend retreat, this country estate offers the tranquility of country living with the convenience of city access just minutes to the charming village of Pawling, golf, dining, and Metro-North’s Harlem Line, providing a direct connection to New York City in under 90 minutes. At 43 Meeting House Lane, rustic elegance meets refined artistry a truly one-of-a-kind property where inspiration and serenity thrive.
Courtesy: Houlihan Lawrence Inc.
914-962-4900
TO BE BUILT Welcome to Brady Brook falls, part of historic Quaker Hills one of Pawling's most distinguished country side. Enter onto freshly paved road and stone wall entrance. This beautiful lot is on 8.44 pastoral acres with amazing views of open sky and grassy meadows. When the days grow longer and temperatures rise or when the days grow shorter and temperatures drop , there is no better place to find solace than the cozy comforts of home in Brady Brook Falls. Make this your every day vacationing home. Brady Brook has 26 lots, each over 5 acres for privacy . This lot 6 is one of the only lots left available to construct your custom dream home. Board of Health Approved for up to 5 bedrooms, Includes 100 acres HOA shared land for trails, hiking ,cross country skiing and fishing. House shown, stunning new construction, each space is a sanctuary of serenity taste and equality, epitomized by 9 to 10 ft. ceilings, hard wood floors. Shown One story Modern Farm House showcasing open layout, Experience the best in this 3-4 bedrms, two and one half baths, fire place, full basement and 2 car garage. This remarkable home spans generously proportioned rooms perfect for both casual and formal entertaining OR select a different style such as a Colonial, Modern, Ranch etc. Will build to your specifications. Pawling Metro North train 5 min away. 45 min to city. Farmers market on seasonal weekends, near by public lake, Complete with village square shops, restaurants, beauty shop, golf courses, skiing, fitness and so much more. This exquisite property is ideal for equestrian and athletic pursuit. One horse per acre allowed. Plenty of room for a swimming pool, tennis court and outdoor seating arrangements. Custom Builders provided.
Courtesy: Douglas Elliman Real Estate
914-273-1001
Private Lake House on a Private Lake! Little Whaley Lake, a serene 46-acre spring-fed, motor-free lake with only six homes offers unparalleled tranquility. This lot offers 150 feet of lake frontage and a private dock; ideal for peaceful swimming, fishing, kayaking, and reconnecting with nature. There are only 6 homes on this lake, with no public access, creating a quiet and peaceful environment. Bring your architect and your imagination. The 2-story cabin, built in 1906, retains its original character and needs either a re-fresh or use this chance to create your own dream country home. Located in Pawling, NY, just 70 miles from NYC, the property is easily accessible by car or via Metro-North station in town. Many great restaurants and shopping, close access to the Empire Rail Trail for biking. Showings by appointment only.
Courtesy: Compass Greater NY, LLC
914-238-0676
Welcome to 16 Anderson Road — a beautifully crafted modern home perched atop the prestigious Quaker Hill in Pawling. Built in 2023, construction completed in 2024, this thoughtfully designed residence blends contemporary elegance with exceptional functionality, offering over 3,000 square feet of refined living space. From the moment you arrive, the home's charm is undeniable — lush landscaping frames a classic rocking-chair front porch, inviting you into a warm and stylish interior. Inside, the open-concept layout is bathed in natural light and finished with upscale details throughout. The gourmet kitchen is a chef’s dream, featuring a Bertazzoni range, French-door refrigerator, honed quartz countertops, and custom cabinetry. It flows seamlessly into the dining/gathering area where built-ins and a wet bar create the perfect setting for entertaining. The first floor also includes a full bathroom and a cozy flex space ideal for a home office or reading nook. Upstairs, soaring vaulted ceilings enhance the sense of space and light. The primary suite offers a serene retreat with a private en-suite bath, while a second spacious bedroom and additional full bath provide comfort and convenience. The fully finished walkout lower level dramatically expands your living options, with a private entrance, two additional bedrooms, two full bathrooms, washer and dryer, a sleek kitchenette, built-in cabinetry, and so much more. While the space is beautifully finished, it also presents a range of possibilities — from a comfortable mother/daughter arrangement to private guest quarters, or a flexible area that can be tailored to suit your unique needs and vision. Step outside to enjoy a Trex deck overlooking extensive bluestone hardscaping and a custom fire pit area — an idyllic setting for outdoor entertaining or quiet evenings under the stars. Enhancing the property is a beautifully designed detached two-car garage with a spacious upstairs artist’s studio. Featuring soaring vaulted ceilings, abundant natural light, a kitchenette, and a full bath, this exceptional space offers an inspiring setting for creative work, a private office, or a peaceful personal retreat. Ideally located minutes from the Quaker Hill Country Club, Thunder Ridge Ski Area, scenic hiking trails, and the charming Village of Pawling, 16 Anderson Road offers the rare combination of modern construction, stylish upgrades, flexible living space, and boundless lifestyle potential. A unique opportunity to own a turnkey home in one of Pawling’s most sought-after locations.
Courtesy: Hillside Realty & Development
845-519-9165
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.
Courtesy: HomeSmart Homes & Estates
845-547-0005
Back on the market, the deal fell through from the buyer side. 9/17/2025 This house is owned by a church and in New York a sale has to be approved by the Attorney Generals office which can take up to six months. This can work to your benefit depending on your own timeline. This can also be set up a s a short term rental as well while waiting for the approvals WITH PORTION OF RENT GOING TOWARDS THE COST OF THE SALE. . This charming, expansive ranch home is thoughtfully designed to suit a variety of living arrangements, whether for a large family, extended family, or a mother-daughter setup. With 4-5 bedrooms and 4 full bathrooms (3 of which are en suite), this home offers both space and privacy for everyone. The kitchen,featuring elegant soapstone countertops, a copper sink, and distressed cabinetry, along with a breakfast island that invites casual dining. The central dining area flows seamlessly into the cozy living room, where tongue-and-groove cedar walls and a brick wall create a warm, inviting atmosphere. Two additional bedrooms on this side complete the main living space along with a smaller room which can host a variety of needs. The home's flexibility shines through with a unique door separating one wing that offers an entirely self-contained living area. This includes two bedrooms, each with its own full bathroom, as well as a private living room, laundry, and dining area — perfect for extended family, guests, or even rental potential. Multiple sliding doors lead to small, private decks around the home, offering easy access to the outdoors. The basement, accessible through a Bilco door, houses the mechanical systems, electrical panel, oil tank, and offers additional storage space. A standout feature of the property is the separate, two-level building originally built as a one-car garage with an attic for storage. This structure has been beautifully converted into a studio ( was a professional recording studio ) on the second floor, with the finished first floor providing a versatile space with a half bath — ideal for a home office, gym room, workshop, or guest suite. Renovated and designed in 2022 along with heat and A/C system . Adding much value to this property . Recent updates include a new $40K septic system installed in 2021, adding peace of mind for years to come. All of this is nestled on 6 acres of private, serene land, offering plenty of space and privacy. This home is truly a versatile gem, ready to adapt to your lifestyle.
Courtesy: Briante Realty Group, LLC
845-225-2020
THIS HOME WILL NOT BE AVAILABLE FOR OCCUPANCY UNTIL DECEMBER 2026. THERE IS A RESIDENTIAL FACILTY IN PLACE AT THIS SITE UNTIL THEN. This Ranch home offers 5 bedrooms and 2 full baths. There is 2,856 sqft of living space above the walk-out basement. Home is currently being used as a Residential Facility and will be held as a Rental with existing Residents in the home until DECEMBER 2026. This is a unique situation where the home can be held as an investment until 2026 and thereafter utilized by the new owner. Generator included in sale. Sprinklers throughout the interior of the home. Upgraded and expanded Septic. Modular home. Walk out basement has plumbing set up for an apartment (bath and kitchen) but never built out.
Courtesy: MCGRATH REALTY INC. PW
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.
Courtesy: BHHS HUDSON VALLEY PROPERTIES PW
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!
Courtesy: BHHS HUDSON VALLEY PROPERTIES PW
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
Courtesy: Douglas Elliman Real Estate
914-234-4590
25.5-acre equestrian estate with a 43-room Elizabethan Style manor house, two caretaker homes, a carriage house with groom’s quarters, a yoga studio, a 12,000 sq. ft. stable, greenhouse and more. Situated on the crest of Quaker Hill, Elmwood Farm has stunning views and endless possibilities. The 3-story, 17-bedroom (7 of which are in the nursery wing and the caretakers' wing) 9-bath (plus 4 half-baths) mansion, with 10 fireplaces, sits at the end of a long gated drive, where a porte cochere provides gracious access to the sunset-facing veranda. The home features a wealth of exquisite details, including hand-carved pilasters, hand-painted plaster ceiling motifs and moldings, leaded glass windows, and variegated gables with carved vignette timber fascia and Gothic spires. The figured-oak grand staircase is enhanced by 30 newel posts with hand-carved whimsical animals. A separate wing on the second floor features hand-painted storybook murals. Additional Information: Amenities:Marble Bath,Pedestal Sink,Storage,Tennis,HeatingFuel:Oil Below Ground,ParkingFeatures:4+ Car Detached,
 |
| The data relating to real estate for sale or lease on this web site comes in part from the MHMLS. Real estate listings held by brokerage firms other than this broker', Realtors are marked with the MHMLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker. The information appearing herein has not been verified by the Mid-Hudson Multiple Listing Service, Inc. or by any individual(s) who may be affiliated with said entity, all of whom hereby collectively and severally disclaim any and all responsibility for the accuracy of the information appearing at this web site, at any time or from time to time. All such information should be independently verified by the recipient of such data. This data is not warranted for any purpose. Any use of search facilities other than by a consumer seeking to purchase or lease real estate is prohibited. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025 Mid-Hudson Multiple Listing Service, Inc. All Rights Reserved. |
Pawling is located in New York. Pawling, New York 12564has a population of 8,024. Pawling 12564 is more family-centric than the surrounding county with 32.83% 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 12564 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 12564 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.
