Pawling, New York listings for sale

$14,995,000 - Pawling, NY

15 Kirby Hill Road Pawling, NY - 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, Grand Prix 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.

$1,500,000 - Pawling, NY

21 Brady Brook Farm Road Pawling, NY - Nestled within the prestigious Brady Brook Falls subdivision on sought-after Quaker Hill, this exquisite colonial offers an unparalleled blend of elegance, privacy, and modern convenience. Situated at the end of a serene cul-de-sac, the home is surrounded by picturesque horse farms and country estates. A long, private driveway leads to this stunning 6.65-acre retreat, complete with a heated saltwater inground pool, providing the ultimate sanctuary. With 4,683 SF of meticulously designed living space, this home boasts grand-scaled rooms, soaring ceilings, and expansive windows that invite natural light while offering seamless integration with the surrounding landscape. The craftsmanship is evident from the moment you step inside, with high-end finishes, an open-concept layout, and captivating spaces that elevate the home's sophistication. The first floor features a gracious entryway leading to a formal dining room with ample seating for ten, perfect for entertaining. A magnificent two-story great room with stone fireplace and interior balcony opens to a sunlit living room with French doors leading to a screened-in porch. From the great room, a wall of French doors leads to the poolside patio. Adjacent is the designer kitchen, a culinary dream with a center island that seats four, granite countertops, a quartz backsplash extending from counter to ceiling, and top-of-the-line Wolf, Subzero, and Miele appliances. The kitchen also includes a barista bar, abundant cabinetry, and a pantry. Completing the first floor is a private den/office, an inviting primary suite with an ensuite bath, a mudroom, and a stylish half bath. Upstairs, the second grand-sized primary suite is a true retreat, featuring a sitting room with a cozy fireplace, a private balcony, dual walk-in closets, and a spa-like bath. Two additional bedrooms share a well-appointed bath, while a convenient laundry room completes the level. The expansive 2,767-square-foot unfinished basement presents endless possibilities for future customization. This home is designed for both comfort and practicality, with a three-car garage equipped with a Tesla charger, a Generac 24 kW generator, a Culligan double osmosis water purity system, a Qolsys IQ wireless smart home security system with ADT monitoring, a Sonos system with speakers in the interior and exterior of the home, and an OmniLogic pool automation system. The outdoor spaces are equally impressive, featuring a covered mahogany porch, a screened-in porch, and a heated saltwater pool surrounded by a designer pressed concrete patio, BBQ island, fenced-in play area, extensive stonework, and lush, manicured lawns. Brady Brook Falls offers miles of winding woodland trails, with a tranquil pond and scenic bridge just across the street for easy access. While this private haven provides a serene escape, it is just minutes from the Village of Pawling, a charming 18th-century town known for its fine dining, boutique shops, antique stores, cultural attractions, and seasonal farmers market. With its very own Metro North station, Pawling offers a convenient 90-minute train or car ride to NYC, making this extraordinary estate the perfect blend of refined country living and accessibility.

$1,485,000 - Pawling, NY

604 N Quaker Hill Road Pawling, NY - Exceptional living awaits in this stately Georgian manor house sitting on 7 acres at the top of prestigious North Quaker Hill Road. This mostly original home offers 9’ ceilings, radiant heating and ownership that has changed hands only once. A Belgian cobblestone driveway has a center focal point awaiting your personal touch.The Living room opens to an elegant wraparound terrace, perfect for the most formal gathering or Sunday football. The library has built in mahogany cabinetry and a full wet bar adjoins the dining room. Open airy kitchen with 12’ island and two of each appliance, a true chef’s delight. Start your day in the cozy sunlit breakfast room where a huge bay window is host to expansive views of the lawns, French doors to the 25 x 50 pool, the perfect setting for outdoor fun and alfresco dining on a sunny day. Take the elevator,staff or main stairs up to 5 bedrooms each with its own ensuite bath,heating and cooling. The primary bedroom offers floods of sunshine, plenty of closets and is home to one of the five woodburning fireplaces.. The bonus lower level has an Italian cypress wood Game Room and entertainment room with wet bar, wine cellar and separate staff quarters. Two locker room style bathrooms complement the USTA regulation tennis court. Just an hour to NYC. Minutes to Metro North. Lower level offers an additional 2000+ sq feet of finished living space. Additional Information: Amenities:Pedestal Sink,Soaking Tub,Storage,Tennis,ParkingFeatures:3 Car Attached,

$1,100,000 - Pawling, NY

51 Estate Drive Pawling, NY - Don't miss this opportunity to have your dream home built and custom designed to your finishes. As you step inside, you're greeted by a grand foyer entrance with high ceilings open to the second floor. Discover a beautifully designed eat-in kitchen, complete with custom cabinetry, stainless steel appliances, quartz countertops, and center island. The oversized open floor plan seamlessly connects the kitchen and family room which features a cozy gas fireplace, creating a warm ambiance. The main level also includes a formal dining room and living room. Upper level continues to impress with an oversized primary bedroom with a mini bar, spa like bathroom, custom shower stall, tub, and oversized walk-in closet. Two additional bedrooms both include full bathrooms. The unfinished basement presents endless possibilities with plenty of room for your imagination to flourish. The bonus space over garage can be built out into two bedrooms with a shared full bathroom for an additional cost. Possible owner financing.

$899,000 - Pawling, NY

26 Rodina Drive Pawling, NY - Brand New Construction in a convenient location on a cul-de-sac with wooded views. Check out this modern and light-filled home with state-of-the-art features. Spray foam insulation throughout and high efficiency heating and central air with wifi thermostats for low heating and cooling costs. Covered front porch. Entrance foyer with 2 closets and custom modern railing with motion sensor stair case lighting. Hardwood flooring throughout. Formal living room open to family room with built in electric fireplace. Eat in kitchen with stainless steel appliances, induction cook top & pot filler, quartz counters with waterfall, center island, stainless steel farmhouse sink and oversized 12 ft wide European sliding door out to patio and rear yard. Formal dining room. Powder room on first floor. Master bedroom with tray ceiling, walk in closet. Master bath complete with soaking tub, shower with speakers and mood lights, backlit and fog free vanity mirrors, smart toilet and heated floors. 3 additional family bedrooms. All bedrooms have wifi lights and fans. Hall bath with double sinks, smart toilet and heated floors. Second floor laundry room and a 500 sq ft bonus room! Basement has high ceilings, recessed lighting and can add an additional 1300 square feet. Full insulated storage attic. 2 Car garage with door out and Smart garage door openers. Maintenance free exterior. There's still time to choose the stain color on floors, shower doors and to customize your closets. Built by JVR Homes,LLC "We don't just build houses, we build homes" ...

$889,000 - Pawling, NY

26 Rodina Drive Pawling, NY - Welcome to your brand new dream home! Nestled on a beautiful and peaceful two and half acres. Be the first to live in this stunning four bedroom, two and a half bath home. 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 with motion sensor lighting on staircase. 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 the train. 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!

$799,999 - Pawling, NY

94 S Quaker Hill Road Pawling, NY - Welcome to Sunset View! Nestled on 3.24 acres of picturesque private land, this sprawling 4-bedroom split-level home offers a perfect blend of spacious living and expansive outdoor amenities including a 20 x 50 salt water inground pool. As you approach along the freshly paved driveway, you'll be welcomed into your very own private oasis. Upon entering through the front door, you’ll step into a bright foyer with hardwood floors, leading to a generously sized dining room. This space features crown molding, a large bay window framing scenic views, and a seamless walk-through to the large eat-in kitchen. The kitchen is a chef’s dream, equipped with custom cherry cabinets, a double oven, and a propane cooktop with a down draft, providing ample storage and functionality. Upstairs, you'll discover a beautifully updated bathroom with a large tiled walk-in shower, plenty of storage, and a sleek marble countertop. This level also includes two cozy bedrooms with hardwood floors and plenty of closet space, a spacious office, and the impressive primary suite. The suite features two large closets, hardwood floors beneath the carpet, a spiral staircase leading to the lower living area, a dressing room with a sink, and an additional large closet. The en-suite bathroom includes a sunken tub for ultimate relaxation. The lower level is designed for comfort and entertainment. A spacious living room with a wood-burning stove and a built-in bar area sets the tone for gatherings. This level also includes a sitting room, a bedroom with double closets, a full bathroom, and a laundry area. From here, you can step out to the patio with a hot tub and a stone stairway leading to the spectacular 20x50 in-ground salt pool, featuring a brand-new liner. This stunning property also offers a whole-house generator, a large garage beneath the house, a detached garage, a treehouse, a chicken coop, mature landscaping, fruit trees, and sweeping views. With every detail thoughtfully planned, Sunset View is a truly exceptional place to call home!

$749,900 - Pawling, NY

28 Gobblers Knob Road Pawling, NY - Welcome to 28 Gobblers Knob Road – A Hudson Valley Equestrian Retreat! Nestled in the heart of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on a breathtaking 20+ acre property offering peace, privacy, and natural beauty in every direction. Whether you're looking for a serene country getaway or a horse property, this one-of-a-kind home is the perfect match. The charming residence features a warm and inviting layout with spacious living areas, abundant natural light, and tranquil views. Recent improvements include a roof replacement and a freshly painted exterior within the last few years, ensuring both durability and curb appeal. Step outside and take in the sweeping landscape—ideal for riding, relaxing, or simply enjoying the open skies and fresh air. Equestrian lovers will appreciate the large barn, perfect for housing horses, tack, and feed, as well as the expansive grounds ready for paddocks or training areas. A detached oversized 2-car garage offers ample room for vehicles, equipment, or workshop space. Located within close reach of local shops, dining, and outdoor recreation, and just under 2 hours from NYC, this is your chance to own a slice of Hudson Valley paradise. Don’t miss the opportunity to turn this dream property into your reality.

$699,000 - Pawling, NY

5 Red Tail Court Pawling, NY - Tucked away on a quiet cul-de-sac in the sought-after Deerfield Ponds community, 5 Red Tail Court is a beautifully maintained 5-bedroom, 2.5-bathroom Colonial offering space, style, and convenience. With 2,924 sq ft of living space, this home features an inviting floor plan, perfect for both everyday living and entertaining. Step inside to find a sun-filled living room with a cozy fireplace, a formal dining room, and an updated kitchen with stainless steel appliances, granite countertops, and ample cabinet space. The spacious primary suite boasts a walk-in closet and a private en-suite bath, while three additional bedrooms provide plenty of room for family, guests, or a home office. Outside, enjoy a beautifully landscaped yard, ideal for outdoor gatherings or quiet relaxation. The attached two-car garage and full basement offer plenty of storage. Located just minutes from Pawling’s charming village, Metro-North station, parks, and schools, this home provides an easy commute to NYC while offering the tranquility of Hudson Valley living. Don’t miss this incredible opportunity to own a stunning home in a prime location! Schedule your private showing today.

$650,000 - Pawling, NY

13 Rebecca Drive Pawling, NY - This Ranch home offers 6 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 Invesment until 2026 and thereafter utilized by the new owner. Generator included in sale. Sprinklers throughout the interior of the home. Upgraded and expanded Septic.

Pawling, New York listings for sale

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