Courtesy: RE/MAX Classic Realty
914-243-5200
Charming Cape Cod on a private cul de sac right on the outskirts of the Village of Pawling yet located in the Town of Pawling. Walking distance to the Village, trains, golf, and easy access to the highways. The open country kitchen with bay window is open to the dining area, central a/c, screened in porch overlooks private yard, multiple decks, mature landscaping with lots of perennials, wood burning stove for those cold nights as well as a gas fireplace. Hardwood floors and laminate throughout. There are 3 bedrooms and 2 full baths on main level with master bath. Walkup stairs to finished storage area (additional 384 sq. ft.) has many potential uses. There is a full basement with a workshop, miscellaneous room, laundry, utilities, and 1 car garage. A warm and inviting home with no thru traffic on 2.2 private acres at the end of dead end street. Enjoy the charming Village of Pawling that offers boutique shopping, fine dining, casual eateries, bakeries, and a seasonal farmers market, while the Metro-North train offers an easy commute to NYC. Pawling is a wonderful place to live in with your very own private retreat.
Courtesy: McGrath Realty Inc
845-855-5550
Welcome to country living at its finest. Set on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential and timeless charm. A long tree-lined driveway leads to the 4 bedroom, 4 bathroom home surrounded by open fields, mature trees, and peaceful countryside views. The property includes a spacious 5-car garage (3 in front and additional 2 car tandum in back) with finished living space 1 bedroom, living room and a full bathroom above. Inside, much of the home’s original character remains with hardwood floors, crown molding, fireplaces, and hidden staircases throughout. The inviting main level features a quiet library or office with fireplace, a bright sunroom overlooking the yard and patio, a spacious living room with fireplace, and a large dining room ideal for entertaining. The kitchen is ready for your personal vision. Upstairs offers 4 unique guest bedrooms along with a spacious Primary Suite featuring hardwood floors, private staircase, large bath, and ample closet space. With room for horses, gardens, or simply enjoying the beauty and privacy of the outdoors, this special property is full of opportunity and old-world character.
Courtesy: Houlihan Lawrence Inc.
845-279-6800
This meticulously maintained 3-bedroom, 2-full-bath contemporary split-level home sits on over 2.33 acres of professionally landscaped property and has so much to offer, from its outstanding curb appeal to its open floor plan. The main level features an eat-in kitchen with oak cabinetry, granite countertops, and NEW state-of-the-art, top-of-the-line stainless steel Bosch appliances, including a coffee station. The dining area offers French doors leading to a large deck that spans the entire back of the house. The spacious living room features a pellet stove to help reduce heating costs and flows seamlessly into the highly desirable open-concept layout, perfect for entertaining. Also on this level is a huge great room with a propane stove for added efficiency and sliding glass doors leading to the back deck. A NEWLY renovated full bathroom and laundry room feature a laundry chute, folding area, and abundant storage, all meticulously finished with knotty pine, barn-style doors, and custom cabinetry. An extra refrigerator in the storage area is included. The upper level features a huge primary suite with an amazing custom-built walk-in closet/dressing room, a NEW full bathroom, and two additional bedrooms. Additional updates include NEW windows, NEW solid wood doors throughout, and ALL NEW flooring. The home also includes a new stainless steel washer and dryer, a roof only 6 years old, a driveway 7 years old, a water heater only 7 years old, NEW A/C units, a NEW heat pump, and a NEW whole-house water filtration system. The property also offers a partially fenced yard and an amazing workshop/shed for the handy person. Conveniently located just minutes from I-84.
Courtesy: McGrath Realty Inc
845-855-5550
Pure perfection! This beautifully and fully renovated 3-bedroom, 2-full-bath home offers modern luxury and total peace of mind. Step inside to an open, sun-drenched living space featuring high ceilings and gleaming hardwood floors throughout. The stunning kitchen boasts sleek quartz countertops, stainless steel appliances, and a spacious pantry for all your storage needs. Convenience is key with a dedicated laundry room, a linen closet, and additional closet space. Stay comfortable year-round with an efficient heat pump and central air. Outside, enjoy your private back deck overlooking just under an acre of park-like manicured lawn surrounded by a serene, partially wooded backdrop. Complete with a brand-new blacktop driveway offering plenty of parking. This gem offers easy access to I-684, I84, Thunder Ridge Ski Area, bike trails and Metro North. Just minutes from dining and shopping and a short drive to the Village of Pawling A truly turn-key property— Absolutely nothing to do but move right in and enjoy!
Courtesy: eXp Realty
888-276-0630
Welcome to one of the Hudson Valley's most extraordinary hidden treasures—a private island retreat nestled in the heart of Whaley Lake, where every day feels like a vacation and every arrival feels like an escape from the ordinary. Accessible only by boat, this remarkable waterfront residence offers an exceptionally rare opportunity to own a piece of paradise within an exclusive island co-op community where properties seldom become available. From the moment you leave the mainland behind and cruise across the sparkling waters to your own private dock, you'll experience a level of peace, privacy, and seclusion that is nearly impossible to find in today's world. Surrounded by panoramic lake views and embraced by nature, this charming island getaway captures the essence of lakefront living at its finest. Wake each morning to shimmering sunrises dancing across the water, spend your days boating, swimming, fishing, or simply relaxing lakeside, and unwind in the evening as spectacular sunsets paint the sky in brilliant colors reflected across the lake's glassy surface. Inside, the home exudes warmth, comfort, and timeless lake-house charm. Thoughtfully designed for both relaxation and entertaining, the residence features two bedrooms, a spacious sleeping loft, and two beautifully renovated full bathrooms. Comfortable gathering spaces invite friends to create lasting memories, while expansive lake views serve as the backdrop to nearly every moment. Whaley Lake is one of Dutchess County's premier motorboat lakes, offering endless recreational opportunities and year-round natural beauty. Located less than 90 miles from New York City, this unique property provides the perfect weekend sanctuary, summer retreat, or lifestyle investment for those seeking a truly one-of-a-kind waterfront experience. As an added bonus, the home is being offered almost fully furnished, allowing you to begin enjoying island life immediately. And the ultimate finishing touch? Included in the sale is a stunning 2021 Nautic Star 24-foot boat powered by a 250 HP engine—your gateway to exploring the lake and making every arrival home an unforgettable experience. Private island living. Private dock. Premier lakefront location. Turnkey convenience. Included boat. Opportunities of this caliber are extraordinarily rare. This isn't simply a home—it's a lifestyle, a retreat, and a legacy property that offers an experience few will ever have the chance to own. Schedule your private showing today and discover why life on Whaley Lake is unlike anywhere else.
Courtesy: Houlihan Lawrence Inc.
914-277-8040
Space, style, and convenience come together in this beautiful Squire Green home. Featuring a brand-new kitchen with granite countertops, gas stove and stainless steel appliances, spacious living areas, a cozy fireplace, and oversized bedrooms. Need space? This home delivers. The home continues to impress with a large unfinished basement offering endless potential for additional living space. Located just minutes from the charming town of Pawling, Metro-North, parks, schools, restaurants and shops, convenient commute to NYC while enjoying suburban tranquility. Don't miss this exceptional opportunity.
Courtesy: Four Seasons Sothebys Intl
518-822-0800
Farm Nord is a meticulously restored country estate, originally established in the 1700s as a dairy farm by the renowned Taber family of Rhode Island. The Tabers were stewards of the estate for five generations and two centuries, with only a few families since carrying on its legacy. The property’s idyllic 12 acres are peppered with endless stone walls, several-hundred-year-old trees, and rolling meadows. The seat of the estate, a traditional gentleman’s farmhouse, lies at the end of a long gravel driveway lined with historic sugar maples on both sides. The original barn has been renovated, with a charming cedar-shake roof and an attached fenced kitchen garden, and a sweet cottage nestled into the hills above the house has an interior wood-burning sauna and wellness space. The nearly 300 year old, three bedroom, three bath home has been thoughtfully preserved, without compromising the authenticity of the original details, including the wide board wood floors, long beams, and five wood-burning fireplaces. The kitchen was created in tandem with a masterful local craftsman and woodworker, featuring DeVOL fixtures, La Cornue sinks, a dual Wolf range, top-quality appliances, aged brass hardware, and entirely custom cabinetry. The kitchen connects to a light-filled family breakfast nook that overlooks, through walls of French doors, the property’s outdoor dining terrace and picturesque gardens. Off the kitchen, on one side, is the formal living room with a wood-burning stone fireplace, and on the other is the light-filled dining room with the original cooking hearth and a butler’s pantry. A wallpapered full bath and a quintessential mudroom finish the first floor. Upstairs, the family room has tall, vaulted ceilings with wood beams, a fireplace, built-in window benches with storage, and some of the prettiest views of the property from its tall windows and French doors. Off the family room is a richly colored office with custom cabinetry, paneled walls, and a skylight that streams in light throughout the day. The primary suite is tucked away in its own wing of the house, and has a hearth fireplace, a large walk-in closet with beautiful cabinets and extensive storage, and a tastefully appointed bathroom. The remaining two bedrooms look out over the meadows surrounding the home, and share the third bath with a claw-foot soaking tub. Farm Nord is bordered by hundreds of acres of conserved land, making for an abundantly peaceful setting. The original barn, fully restored, has a workshop/studio space, gym, and plenty of additional storage. There is an established herb garden with installed irrigation next to the barn and tall fencing. A small building nestled atop the property’s hills has been converted into a wood-burning sauna. Trails meander through the property’s twelve acres, and a truly incredible number of stone walls line the lush meadows. Farm Nord is conveniently located less than 90 minutes from New York City and just 10 minutes from the Metro North station in the quaint village of Pawling. The area is filled with bucolic farms, rolling hills, and stretches of the Appalachian Trail, making it an excellent area for anyone who loves hiking, wild swimming, and biking.
Courtesy: RE/MAX Classic Realty
914-243-5200
Rare Real Estate Opportunity! Character, Space, and Double the Potential! Bring your vision to this charming, expanded 1940s Cape style home! Set on a private, partially wooded level one-acre site perfectly situated directly across the street from the scenic Maybrook Trailway section of the Empire State Trail and minutes to the villages of Pawling & Patterson, Metro-North, Route 22, and I-84. The main house features 4 bedrooms and 2 full baths. The first floor offers an inviting living room, dining room, eat-in kitchen with rear yard access, and a first-floor bedroom and full bath. The expansive family room features an open raised ceiling and a brick fireplace. Upstairs, you will find three additional bedrooms, a full bath, and plenty of eave storage. An unfinished basement includes a convenient built-in garage space. The crown jewel of this property is the unique, pre-existing, non-conforming separate cottage! This detached bonus space is perfect for an income-producing rental, guest suite, or extended family. The home features some updates and some older systems and is being sold strictly in "As-Is" condition, making it the ultimate canvas for a buyer looking to remodel, renovate, and build instant equity. Bring your tools, your contractor, and your imagination to unlock the immense potential of this one-of-a-kind property!
Courtesy: Houlihan Lawrence Inc.
845-279-6800
Lakefront Cape Cod on beautiful Lake Dutchess awaits its new owner. With over 250 feet of lake frontage and set on more than half an acre of lush, landscaped property, this charming 1930s home offers sun-drenched interiors, exposed beam ceilings, a wood-burning fireplace, and breathtaking lake views throughout. Freshly painted, the home provides a perfect canvas for its next chapter. The main living space is warm and inviting, featuring hardwood floors, oversized windows, and an effortless flow from the kitchen to the dining room and living room. The wide galley kitchen offers abundant cabinetry, generous counter space, and stainless steel appliances. A passthrough window to the living room welcomes natural light and shimmering lake views. The light-filled living room is designed for year-round enjoyment, whether watching ducks glide across the lake or relaxing beside the stone fireplace on a crisp winter day. Just steps away, the dining room showcases beautiful water views and serves as an ideal setting for intimate dinners or larger celebrations. Adjacent to the dining area, the screened-in porch features a high wood-accented ceiling and ample room for al fresco dining while overlooking the lake. The main level also includes a private office, a tucked-away bedroom with hardwood floors and custom built-ins, and a full bath beautifully appointed with a glass-enclosed shower, pedestal sink, and soaking tub. With tranquil lake views, the bath creates a peaceful retreat to unwind at the end of the day. Upstairs, the home’s charm continues with a cozy landing perfect for a reading nook, a versatile skylit bonus room with hardwood floors, a second bedroom overlooking the lake, and a spacious bath with dual pedestal sinks and a large soaking tub. This upper level offers an ideal guest suite or private primary retreat. The outdoor spaces are equally inviting, featuring a stone patio, multiple private seating areas, beautiful mature shade trees, a greenhouse, and easy lake access for swimming, kayaking, and boating. An oversized outbuilding completes the property. Once used as an artist’s studio, its abundant natural light, high ceilings, and expansive windows make it ideal for a creative workspace, yoga studio, game room, or additional recreational use. Designed for both full-time living and weekend escapes, this home offers four seasons of enjoyment—from kayaking on summer mornings and vibrant autumn foliage to picturesque winter lake views and the renewal of spring. Conveniently located just 70 minutes from New York City and close to I-84, I-684, the Taconic Parkway, nearby Metro-North Railroad stations, shopping, walking trails, restaurants, and the charming Village of Pawling, this exceptional property is a rare opportunity to experience the best of Hudson Valley lakefront living.
Courtesy: Keller Williams Realty Partner
914-962-0007
Nestled on 3.37 picturesque, partially wooded acres, this beautifully maintained 3-bedroom, 3.5-bath residence offers an exceptional blend of privacy, comfort, and natural beauty. Surrounded by mature trees and tranquil landscapes, the property provides a peaceful retreat with expansive open areas perfect for outdoor recreation, entertaining, gardening, or simply enjoying the serene setting. Inside, a spacious and thoughtfully designed floor plan welcomes you with bright, inviting living spaces enhanced by abundant natural light and scenic views from nearly every window. Generously sized bedrooms provide comfortable accommodations, while three full baths and a convenient powder room offer both functionality and convenience for family and guests alike. The home's seamless connection to the outdoors creates an atmosphere that is both warm and refreshing, making it ideal for everyday living as well as memorable gatherings. Whether you're seeking a private country escape, a property with room to roam, or the perfect balance of wooded charm and usable open space, this exceptional home offers the versatility, tranquility, and lifestyle you've been searching for. With the added bonus of solar panels to keep utility costs down!
Courtesy: McGrath Realty Inc
845-855-5550
1564 Route 292 offers a rare opportunity to own a true lakefront retreat on Whaley Lake in the heart of the Hudson Valley. Set on an oversized parcel with adjacent open space that will never be built on, the property enjoys an uncommon sense of privacy and breathing room rarely found on the lake. The home underwent a major renovation and expansion in 2007, including the addition of a second-floor loft area and full bath, blending rustic lake house charm with modern functionality. A stylish kitchen renovation completed in 2019 adds updated finishes while maintaining the relaxed character of the home. One of the property’s standout features is the walk-out lower level, which opens directly to water level, creating an effortless connection to the lake for kayaking, swimming, entertaining, or simply enjoying the view. The setting feels tucked away and peaceful, yet remains accessible to Pawling, Metro-North, and the surrounding Hudson Valley destinations. Whether you’re looking for a weekend escape from the city or a year-round waterfront home, this is the kind of authentic lake property that rarely becomes available.
Courtesy: World Homes Realty
845-225-2888
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. The Primary Bedroom Suite has Full Bathroom and walk in Closet and 2 more Bedrooms over looking the Level Property. 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.
Courtesy: Serhant LLC
646-480-7665
Set high atop the storied crest of Quaker Hill, Elmwood Farm is a legacy estate where Hudson Valley history, architectural grandeur, and pastoral beauty converge. Approached by a long, winding gated drive, the property reveals itself gradually across 25.5 rolling acres before arriving at a striking Elizabethan style manor that has stood watch over the surrounding countryside for generations. Quaker Hill has long been known as one of the Hudson Valley’s most distinguished enclaves. For more than a century it has quietly attracted artists, writers, diplomats, and those seeking privacy, landscape, and a connection to history. Elmwood Farm stands among the hill’s most recognizable estates, shaped by generations of stewards who helped define the character of this remarkable hamlet. Owning Elmwood Farm is not simply about acquiring a home. It is about becoming part of the long story of Quaker Hill and carrying that legacy forward. The manor itself reflects the craftsmanship and romance of another era. Leaded glass windows cast soft light throughout the interior, while hand carved pilasters and hand painted plaster ceiling motifs reveal the artistry and attention to detail that defined the estate’s original design. Dramatic rooflines with carved timber fascia and Gothic inspired spires create a striking architectural silhouette that rises above the surrounding landscape. At the center of the home, a magnificent figured oak staircase ascends through the interior, its hand carved newel posts adorned with whimsical animal figures that speak to the individuality and charm of the residence. Gracious gathering rooms anchored by ten fireplaces provide spaces that feel both intimate and grand, equally suited for quiet evenings by the fire or lively gatherings with friends. A charming upper wing with hand painted storybook murals adds an unexpected and delightful layer of character that reflects the estate’s long and colorful history. Beyond the main residence, Elmwood Farm unfolds as a true country compound. The property includes two caretaker homes, a carriage house with groom’s quarters, a yoga studio, and a greenhouse, offering extraordinary flexibility for guests, staff, creative pursuits, or wellness focused living. The grounds themselves are equally compelling. Rolling lawns, mature trees, and sweeping views across the surrounding countryside create a sense of scale and serenity that is increasingly rare in today’s world. The landscape feels timeless, a place where mornings begin with mist rising over the hills and evenings conclude with golden sunsets stretching across the valley. For the next owner, Elmwood Farm offers something truly rare. It is an opportunity to become the next steward of one of Quaker Hill’s historic estates and to preserve a remarkable piece of Hudson Valley history while shaping its next chapter for generations to come.
Courtesy: Keller Williams Realty Partner
914-962-0007
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!
Courtesy: McGrath Realty Inc
845-855-5550
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!
Courtesy: Gillian Stewart Real Estate
845-855-5092
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.
Courtesy: Berkshire Hathaway HS NE Prop.
203-744-5544
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 Is Included In The <3 Acres & Its 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 Salt Water Pool As You Enjoy Your Morning Coffee & Your Evening's Glass Of Wine. Come! Relax, Unwind, & Enjoy Life!
Courtesy: McGrath Realty Inc
845-855-5550
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 with MAAX jacuzzi tub (with color and light therapy settings) lead you to the primary suite. This space features soaring ceilings, hardwood floors, a primary bath with a freestanding copper sleigh tub for two, a glass-enclosed tiled shower, and a custom walk-in closet with built-ins galore. 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, 27 owned solar panels keep electricity costs between $0–$150/month. The three-car garage sits steps away with an additional interior space for toys or lawn maintenance machinery, while just outside, you'll find a whole-home generator that has all your necessities covered. In the southwest corner of the property, there is a 2,400 square foot steel building featuring radiant floor heating, running water, and its own generator, providing endless possibilities limited only by the expanse of the land itself. Minutes from the Village of Pawling and Metro-North, this is country living without compromise.
Courtesy: Douglas Elliman Real Estate
914-234-4590
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.
Courtesy: McGrath Realty Inc
845-855-5550
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.
Courtesy: McGrath Realty Inc
845-855-5550
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.
Courtesy: Hudson Property Services, LLC
845-345-4477
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.
Courtesy: Dixon Smith Realty
914-489-7005
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.
Courtesy: Howard Hanna Rand Realty
845-358-7310
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.
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 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.
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.
