Pawling NY Real Estate & Homes for Sale

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Beds:
2
Baths:
3.00
Sq.Ft.:
1,723
Status:
NEW LISTING
MLS#:
980295
Type:
Single Family
Subdivision:
Squire Green
Lot size:
0.06 Acres
Year built:
1987
A broker reciprocity listing Courtesy: Howard Hanna Rand Realty 914-769-3584
View additional info

ADDITIONAL INFORMATION

Welcome to Squire Green, a charming 2 bed, 2.5 bath townhome that’s move-in ready and full of potential. A versatile den offers the flexibility of a third bedroom, making this home a perfect fit whether you’re growing, downsizing, or simply need extra space. Enjoy the convenience of an attached garage and private driveway, plus ample guest parking. The community offers an in-ground pool, tennis courts, playground, clubhouse, and fitness room. Out back, a private deck opens to a generous, tree-lined yard. Recent upgrades include: stove/oven (2025), garage door & opener (2025), water heater (2024), upstairs windows (2023), and vinyl flooring (2023). All that’s left is adding your personal touch. Close to restaurants, shops, and train! Schedule your showing today!

Open House:

Sunday, 4/12 2:30-4:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
2,104
Status:
NEW LISTING
MLS#:
978698
Type:
Single Family
Subdivision:
Deerfield Ponds
Lot size:
0.24 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Mark Seiden Real Estate Team 914-762-2200
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ADDITIONAL INFORMATION

Welcome to this beautifully maintained Victorian-style home, ideally situated in the highly sought-after Deerfield Ponds community at Squire Green in Pawling. From the inviting wraparound porch to the thoughtfully designed interior, this home offers timeless character paired with modern updates. The first floor features hardwood floors throughout, a formal dining room, and a sun-filled living room. The spacious kitchen is perfect for everyday living and entertaining, complete with a center island, stainless steel appliances, pantry closet, recessed lighting, and a cozy breakfast nook with a pellet stove. Sliding glass doors lead to an expansive rear deck overlooking the lush, level backyard. A versatile mudroom—ideal as a home office—provides convenient access to the attached two-car garage. Upstairs, the primary suite offers new carpeting, a walk-in closet, and an updated en-suite bath. Two additional bedrooms and an updated hall bathroom complete the second level, along with the convenience of second-floor laundry. Additional highlights include: full, unfinished basement with above-ground oil tank, updated roof and hot water heater, generous outdoor space perfect for entertaining. Residents of Deerfield Ponds enjoy exceptional amenities, including a clubhouse, outdoor pool, fitness center, playground, basketball courts, tennis and pickleball courts, plus scenic ponds and green spaces. Ideally located just minutes from the Village of Pawling, this home offers easy access to parks, shops, schools, transportation, and all the charm and attractions of the Hudson Valley. There are no audio recording devices inside this property.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,706
Status:
Active
MLS#:
978836
Type:
Single Family
Lot size:
2.87 Acres
Year built:
1979
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-855-5550
View additional info

ADDITIONAL INFORMATION

Tucked away at the end of a quiet cul-de-sac, this beautifully maintained home sits on 2.87 acres of mostly level, private property—offering the perfect blend of peaceful surroundings and everyday convenience. Step into a bright and welcoming main living area featuring a sun-filled living room with an oversized picture window framing peaceful views of the front lawn, and a dining room with sliding glass doors that open to a spacious Trex deck (2023) and tranquil backyard. The backyard is a completely private oasis where the only sounds are birdsong and the soft rustle of the trees—perfect for quiet mornings, firepit evenings, and effortless entertaining. The completely updated kitchen (2024) with stainless steel appliances flows seamlessly to the attached 2-car garage and backyard access. A few steps down, the expansive family room offers the perfect gathering space with laundry, generous storage, and easy walkout access to the yard. Warm, welcoming, and wonderfully friendly home is the perfect setting for everyday living, celebrations, and lasting memories. Upstairs, you’ll find three comfortable bedrooms, including a primary suite with a private half bath and its own charming deck—ideal for morning coffee overlooking the peaceful property. A beautifully updated full bath completes the upper level. Recent upgrades include brand-new central air (July 2025), new luxury vinyl flooring, fresh paint, a new well pump (2022), and a full-house generator-ready hookup. The backyard also features a patio perfect for firepit nights, a propane hookup for grilling, serene landscaping, and a transferable invisible fence throughout the property. Located just minutes from the charming Village of Pawling, enjoy the rare combination of privacy and convenience with a quick walk into town for coffee, restaurants, shops, and community events, plus easy access to hiking trails, Metro-North, schools, and a fantastic commuter location.

Open House:

Sunday, 4/12 11:00-1:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
1,639
Status:
Active
MLS#:
977687
Type:
Single Family
Subdivision:
Cedar Valley
Lot size:
0.03 Acres
Year built:
1987
A broker reciprocity listing Courtesy: Briante Realty Group, LLC 845-225-2020
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ADDITIONAL INFORMATION

Welcome to Cedar Valley! This bright corner unit offers the perfect blend of comfort and convenience, with potential for easy one-floor living. The main level features both bedrooms, while a spacious loft upstairs provides flexible bonus space—ideal for a home office, gym, guest area, or additional living space. Enjoy the ease of just two steps from the parking lot to your front door, with two conveniently located unassigned spaces right out front. Natural light fills the home, enhancing the open layout and inviting feel throughout. The kitchen features a functional layout with a pass-through to the living room, space for a small table, ceramic tile flooring, and newer stainless steel appliances, including an oven/stove less than one year old. A nearby pantry closet adds extra storage. The living room offers laminate flooring, a fireplace, and access to a private patio—perfect for relaxing outdoors. The primary bedroom includes a generous walk-in closet and a beautifully renovated en-suite bath with a shower stall. A second full bathroom with a tub/shower is located in the hallway. Additional closets throughout the home provide ample storage, along with a main-level laundry closet for added convenience. Upstairs, the expansive loft offers a versatile, airy space that easily adapts to your needs—whether as a home office, guest retreat, media room, or creative studio. Its generous size allows for multiple uses while maintaining an open, comfortable feel. The loft also offers excellent storage, including a dedicated closet housing the water heater and cooling system. Additional highlights include a brand new roof (March 2026) and a spacious exterior storage closet. Cedar Valley residents enjoy community amenities including a pool, tennis courts, and clubhouse. Ideally located less than a mile from the train station and the charming Village of Pawling, with its shops, restaurants, and bakeries. Dutcher Golf Course is just across from the main entrance, and live entertainment is minutes away at Daryl’s House. More photos expected soon.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,942
Status:
Active
MLS#:
965662
Type:
Single Family
Subdivision:
Quaker Hill
Lot size:
247 Acres
Year built:
1860
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-855-5550
View additional info

ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,567
Status:
Active
MLS#:
965344
Type:
Condo
Lot size:
0.09 Acres
Year built:
1987
A broker reciprocity listing Courtesy: Hudson Property Services, LLC 845-345-4477
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ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,413
Status:
Active
MLS#:
960733
Type:
Condo
Subdivision:
Cedar Valley Townhouses
Lot size:
0.02 Acres
Year built:
1988
A broker reciprocity listing Courtesy: Howard Hanna Rand Realty 914-723-8700
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ADDITIONAL INFORMATION

~ 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.

Beds:
2
Baths:
2.00
Sq.Ft.:
2,196
Status:
Active
MLS#:
954200
Type:
Single Family
Lot size:
2.2 Acres
Year built:
1776
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-855-5550
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ADDITIONAL INFORMATION

Step into the very year our nation was born and own a piece of American history! Originally constructed in 1776, this iconic stone residence later became the "Pawling Toll Gate and Toll House," serving as a vital gateway for travelers, a general store, a post office, and a legendary tavern. It is even whispered that George Washington himself once proved his strength within these walls, winning a bet by lifting a 400lb hogshead of beer. Inside, the home breathes character. Hand-hewn beams stretch across the ceilings, deep-set windows welcome the southern sun, and original fireplaces with wood stove inserts serve as the heart of the home. You’ll walk on wide-plank "King’s Wood" floors (massive boards harvested in colonial defiance of the British Crown) that have felt the footsteps of figures like Emilio "Dee" DaBramo. While the history is meticulously preserved, the convenience is modern, featuring a kitchen with custom wood cabinetry, granite countertops and sleek stainless-steel appliances. With 2 bedrooms and 2 full baths, the layout is both intimate and versatile. The lower level offers a private sanctuary perfect for an artist’s studio, a quiet writer’s retreat, or a distinctive guest suite. Outside, the 2.2 acre property is a nature lover’s dream. Groomed trails wind through the land, passing dramatic natural stone features and leading directly to New York State land and the Appalachian Trail. Enjoy direct access to vast untouched nature while ensuring your backyard remains a private, wooded vista forever. Directly across the road, the Maybrook Trailway offers miles of adventure for cyclists and explorers. A two-story, two-car detached garage sits perched on the hill, offering even more potential for storage or creative conversion. Find yourself less than 10 minutes away from boutiques, restaurants, Pawling train station and the grocery store. This isnt just a house; it’s a legacy in a great location. From storied stone walls to the premium modern finishes, every inch of this home has been meticulously maintained to honor it’s 250-year legacy. From its revolutionary roots to its modern-day charm, this is a property without equal.

Beds:
6
Baths:
7.00
Sq.Ft.:
6,625
Status:
Active
MLS#:
956656
Type:
Single Family
Lot size:
71.8 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Dixon Smith Realty 914-489-7005
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ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,088
Status:
Active
MLS#:
922875
Type:
Single Family
Lot size:
0.68 Acres
Year built:
1955
A broker reciprocity listing Courtesy: Howard Hanna Rand Realty 845-358-7310
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,434
Status:
Active
MLS#:
952512
Type:
Single Family
Lot size:
5.5 Acres
Year built:
2001
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 914-223-7623
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,200
Status:
Active
MLS#:
951810
Type:
Single Family
Lot size:
2.41 Acres
Year built:
2025
A broker reciprocity listing Courtesy: Home Sweet Home Properties 914-777-5900
View additional info

ADDITIONAL INFORMATION

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!

Beds:
9
Baths:
15.00
Sq.Ft.:
55,000
Status:
Active
MLS#:
936279
Type:
Single Family
Lot size:
1,337 Acres
Year built:
1987
A broker reciprocity listing Courtesy: Julia B Fee Sothebys Int. Rlty 914-234-0200
View additional info

ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,248
Status:
Active
MLS#:
930472
Type:
Single Family
Lot size:
24.53 Acres
Year built:
1910
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-855-5550
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,200
Status:
Active
MLS#:
811617
Type:
Single Family
Lot size:
5 Acres
Year built:
2025
A broker reciprocity listing Courtesy: Hillside Realty & Development 845-519-9165
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
5.00
Sq.Ft.:
2,361
Status:
Active
MLS#:
811537
Type:
Single Family
Lot size:
5 Acres
Year built:
1930
A broker reciprocity listing Courtesy: HomeSmart Homes & Estates 845-547-0005
View additional info

ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,080
Status:
Active
MLS#:
420091
Type:
Single Family
Subdivision:
V. Pawling
Lot size:
0.2 Acres
Year built:
1928
A broker reciprocity listing Courtesy: MCGRATH REALTY INC. PW
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,306
Status:
Active
MLS#:
419696
Type:
Single Family
Subdivision:
Pawling
Lot size:
1.34 Acres
Year built:
2000
A broker reciprocity listing Courtesy: BHHS HUDSON VALLEY PROPERTIES PW
View additional info

ADDITIONAL INFORMATION

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!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,768
Status:
Active
MLS#:
419595
Type:
Single Family
Subdivision:
V. Pawling
Lot size:
0.34 Acres
Year built:
1960
A broker reciprocity listing Courtesy: BHHS HUDSON VALLEY PROPERTIES PW
View additional info

ADDITIONAL INFORMATION

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

Beds:
4
Baths:
2.00
Sq.Ft.:
1,490
Status:
Active
MLS#:
417978
Type:
Single Family
Subdivision:
Pawling
Lot size:
0.18 Acres
Year built:
1965
A broker reciprocity listing Courtesy: HOULIHAN LAWRENCE INC. LG
View additional info

ADDITIONAL INFORMATION

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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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026, OneKey MLS, Inc. All Rights Reserved.
Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

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 2026 Mid-Hudson Multiple Listing Service, Inc. All Rights Reserved.



Pawling Real Estate

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.

Pawling Weather

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.

Pawling Map

Pawling Real Estate Market Conditions

  • Median sales price

    $523,750
    14%
    change since last quarter
  • # Active listings

    36
    30-day change

Pawling Schools and Demographics

Education near Pawling, NY

City County
High School Graduates 93.39 91.53
College Degree - 2 year 9.66 10.4
College Degree - 4 year 40.14 37.67
Graduate Degree 11.37 13.56
Expenditures per Student 28,380 28,380
Students per Teacher 12.5 12.5

Elementary Schools near Pawling, NY

Grades Students P/T Ratio ZIP
Beekman School KG - 05 512 14.3 12570
Matthew Paterson Elementary School KG - 04 537 15.1 12563
Pawling Elementary School KG - 04 441 11.6 12564
VAIL Farm Elementary School KG - 05 659 13.4 12540
Wingdale Elementary School KG - 02 311 12.2 12594

Middle Schools near Pawling, NY

Grades Students P/T Ratio ZIP
Lagrange Middle School 06 - 08 949 11.8 12540
Pawling Middle School 05 - 08 378 11.8 12564
Union Vale Middle School 06 - 08 1,113 13.3 12540

High Schools near Pawling, NY

Grades Students P/T Ratio ZIP
Arlington High School 09 - 12 3,219 17.5 12540
Pawling High School 09 - 12 394 13.8 12564

Demographics near Pawling, NY

City County
Neighborhood Type Small town
Population 8,024 296,012
Population Density 183 372
Median Age 47.9 42.5
People per Household 2.6 2.5
Median Household Income 106,806 87,112
Average Income per Capita 49,184 44,800

Real estate near Pawling