Pawling Homes for Sale

Pawling: A Charming Town in Dutchess County, NY

Nestled in the heart of Dutchess County, New York, lies the picturesque town of Pawling. Known for its small-town charm and natural beauty, Pawling offers a tranquil and welcoming atmosphere that attracts both locals and visitors alike.

With its convenient location just a short drive from New York City, Pawling provides the perfect escape from the hustle and bustle of city life. Surrounded by rolling hills, lush forests, and serene lakes, this town is a haven for nature enthusiasts. Whether you enjoy hiking, fishing, or simply taking a leisurely stroll through the countryside, Pawling has something to offer everyone.

When it comes to real estate in Pawling, there is a diverse range of options to suit various preferences and budgets. From cozy cottages and historic homes to modern townhouses and spacious estates, Pawling has it all. The town's real estate market boasts a mix of architectural styles, ensuring that there is something to cater to every taste.

Pawling's real estate market is known for its affordability, making it an attractive option for first-time homebuyers and those looking to invest in property. With a range of homes for sale, buyers can find the perfect place to call their own in this charming town.

In addition to its natural beauty and affordable housing options, Pawling is also home to excellent schools, a vibrant downtown area with local shops and restaurants, and a strong sense of community. Residents enjoy a high quality of life and a close-knit community that is welcoming and inclusive.

Whether you are looking to settle down or simply escape for a weekend getaway, Pawling offers a slice of small-town paradise in the heart of Dutchess County, NY. With its natural beauty, affordable housing options, and charming community, it's no wonder that Pawling is a sought-after destination for homebuyers.

Newest Pawling Homes for Sale

$695,000

4 Beds ⋅ 2 Baths ⋅ 1047901 MLS

Situated in the prestigious, historic hamlet of Quaker Hill, this exceptional property offers a rare blend of scale, privacy, & scenic beauty. Set well back from the road at the end of a long, sweeping driveway, the 6.57-acre setting borders the picturesque, rolling pastures of Akindale Thoroughbred Rescue. Offered for the first time in nearly 76 years, this is a rare opportunity to own a distinctive piece of Quaker Hill. The grounds feature soaring mature trees, a well-maintained lawn, & a stream running through the property, creating a beautiful pastoral setting & a truly tranquil retreat. For those seeking greater scale or additional investment potential, the adjacent 4.9-acre lot is also available, offering the opportunity to significantly expand the property’s footprint. Spanning 2,160 square feet, the classic 1950 Colonial features a four-bedroom, two-bath layout centered around a warm fireplace. An established vegetable garden sits just outside the door, ready for farm-to-table living, while a detached garage provides convenient parking & equipment storage. Pawling Village offers a walkable small-town center with local restaurants, shops, & community events just minutes away. Outdoor pursuits are equally close at hand, with Appalachian Trail access, local hiking, & the Harlem Valley Rail Trail all nearby. Metro-North service into New York City provides convenient access for commuters & weekend trips alike. Whether taking in quiet views of the resident rescue horses, tending the garden, or enjoying the stream, this home captures the character of the Hudson Valley—pairing serene country living with easy access to the village and surrounding amenities.

264 Quaker Hill Road, Pawling

$597,500

3 Beds ⋅ 3 Baths ⋅ 1047471 MLS

WELCOME TO DEERFIELD PONDS AND ALL ITS AMENITIES! THIS BEAUTIFUL COLONIAL HOME HAS SO MUCH TO OFFER, SUCH AS GORGEOUS PROPERTY WITH MATURE TREES, NUMEROUS PERENNIAL GARDENS, AND A SCENIC POND VIEW. THE COVERED FRONT PORCH WELCOMES YOU INTO THIS WONDERFUL HOME! SPECIAL FEATURES BEGIN WITH A FIRST-FLOOR PRIMARY SUITE. SPACIOUS, INVITING LIVING ROOM HAS HARDWOOD FLOORING & CROWN MOLDING, AS DOES THE LOVELY DINING ROOM. FANTASTIC KITCHEN FEATURES BEAUTIFUL CEILING-HEIGHT CABINETS, RICH GRANITE COUNTER TOPS, HARDWOOD FLOOR. GREAT FOR ENTERTAINING, THE KITCHEN IS OPEN TO THE SUNNY FAMILY ROOM, WHICH OFFERS A FIREPLACE, CROWN MOLDING AND HARDWOOD FLOOR. OFF THE FAMILY ROOM IS A DECK WITH A RETRACTABLE AWNING - A COOL SPOT ON A HOT DAY! ON THE 2ND FLOOR, YOU WILL FIND A BEAUTIFUL FULL BATH, LAUNDRY, TWO VERY NICE BEDROOMS, PLUS A DEN WITH HARDWOOD, WHICH HAS BEEN USED AS A GUEST ROOM/OFFICE. PAWLING IS A LOVELY, SOUGHT-AFTER TOWN WITH A PICTURESQUE VILLAGE, WHICH OFFERS A METRO-NORTH TRAIN STATION, RESTAURANTS, PUBS, BAKERIES, DUTCHER GOLF COURSE, QUAINT SHOPS, LIBRARY, DARYL'S HOUSE MUSIC CLUB & RESTAURANT, AND LAKESIDE TOWN PARK WITH BEACH, PICKLEBALL & PLAYGROUND. PAWLING OFFERS SOMETHING FOR EVERYONE!

41 W Deer Trail, Pawling

$995,000

4 Beds ⋅ 3 Baths ⋅ 1045580 MLS

Set on over 3 beautiful acres, this spacious 4-bedroom, 3-full-bath home offers an impressive blend of classic character, generous living spaces, and modern conveniences. A welcoming wraparound front porch leads to a grand entry foyer with an open staircase and views to the second floor. The main level features a formal Living Room and Dining Room, both enhanced by large bowed windows, along with a comfortable front Sitting Room. The heart of the home is the expansive eat-in Kitchen, complete with center island, stainless steel appliances, and sliding glass doors leading to the rear deck. A spectacular Great Room boasts soaring ceilings, a fireplace, and additional sliders to the deck, creating an ideal space for entertaining or relaxing. A front mudroom entry, convenient Laundry Room, full tiled Bath with walk-in shower, and hardwood floors throughout complete the main level. The oversized garage offers both a double and single garage door for exceptional parking and storage. Upstairs, three spacious Bedrooms feature hardwood floors and double-door closets. The luxurious Primary Suite offers vaulted ceilings, beautiful bowed front windows, his-and-hers walk-in closets, a large linen closet, and a massive Primary Bath with dual vanities, Jacuzzi tub, and walk-in shower. A large Bonus Room with hardwood floors provides flexible space for an office, media room, playroom, or additional living area. The open upper hallway overlooks the Great Room below, adding to the home's dramatic sense of space. Additional highlights include an expansive unfinished basement, walk-up attic, central air, and central vacuum. Set amid peaceful acreage with plenty of room to enjoy the outdoors, this exceptional home offers space, privacy, and versatility both inside and out.

139 S Harmony Road, Pawling

$404,444

2 Beds ⋅ 1 Baths ⋅ 1045289 MLS

WELCOME TO YOUR OWN LITTLE PIECE OF HEAVEN IN SOUGHT AFTER PAWLING NY. PROPERTY HAS TWO SEPARATE LOTS WITH A TOTAL OF 23.50 ACRES AND HAS OUTSTANDING OUTSTANDING MOUNTAIN VIEWS. OWNER HAS NOT TRIED TO SUBDIVIDE, HOWEVER THERE ARE TWO WELLS ON PROPERTY. THERE IS A NEWLY CONSTRUCTED DECK OFF THE KITCHEN. LIVING ROOM HAS A PELLET STOVE WHICH WAS INSTALLED IN 2020 AND KEEPS THE WHOLE HOUSE WARM AND COZY!! HOME HAS AN UNFINISHED BASEMENT WITH RECENT BLOWN IN INSULATION INSTALLED. HOME WAS RENOVATED IN 2019 WHICH INCLUDES A NEW FURNACE. IF YOU LOVE NATURE, THIS IS THE PLACE TO BE, YOU WILL NOT BE DISAPPOINTED, COME TAKE A LOOK.

265 Old Pawling Road, Pawling

$599,000

3 Beds ⋅ 2 Baths ⋅ 1042803 MLS

Set on over an acre and a half of pure enchantment, this charming predominantly one-level ranch-style home offers thoughtfully designed living space in a private and whimsical setting. A long paved driveway leads to the home, which sits high and well back from the road, creating a sense of seclusion from the moment you arrive. The backyard is truly an oasis, surrounded by lush landscaping, vibrant perennial gardens framed by a stone wall, and a recently renovated Lazy L heated inground pool. Whether envisioned as a weekend getaway or year-round sanctuary, this property offers outdoor living and relaxation at its finest. While the home presents a modest profile from the outside, the interior reveals a stylishly renovated kitchen featuring a center island with seating, crisp white cabinetry, quartz countertops, stainless steel gas range, refrigerator, dishwasher and microwave, subway tile backsplash, abundant storage, floating shelves, and a charming picture window with bench seating and storage below. The view of the pool from the kitchen is so picturesque, it feels like a living work of art. A wide hallway leads to an intimate dining room and a dramatic living room with vaulted ceiling and corner fireplace surrounded by stone. Another hallway leads to two bedrooms, including a comfortable second bedroom with pool views and a serene primary suite. The primary bedroom features French doors opening to a private deck, a bath with potential to expand by incorporating space from the adjacent walk-in closet, and three additional closets. A recently renovated hall bath with walk-in shower, full-size stacked washer and dryer tucked into a convenient laundry closet, and five additional closets of varying sizes complete the main level. From the living room, steps lead to a private third bedroom with charming sloped ceilings. Outside, the magic truly unfolds. The deck off the kitchen is an inviting spot for morning coffee, al fresco dining, or sunset cocktails. The heated inground pool is surrounded by a spacious patio finished with an exceptional concrete coating system, offering plenty of room for lounge chairs and patio furnishings. A stone patio provides the perfect setting for the gazebo, furnished for relaxing and entertaining. Beyond the gate, a custom circular fire pit creates a wonderful gathering place beneath the stars. The pool area is thoughtfully fenced, while a detached one-car garage and separate shed provide additional storage for gardening tools and equipment. Just under four miles from the charming Village of Pawling, you'll have easy access to fine dining, casual eateries, boutique shops, pubs, and the seasonal farmers market. Outdoor enthusiasts will appreciate nearby Lakeside Park, Pawling's town park, the Appalachian Trail, and the Dutchess Rail Trail, now conveniently accessible via the newly completed connector. Golf enthusiasts can choose between the public Dutcher Golf Course and the private Quaker Hill Country Club. For commuters, the Pawling Metro-North station is less than 10 minutes away, providing an approximately 90-minute train ride to New York City. A captivating private retreat with exceptional outdoor living, this enchanting property offers the perfect blend of tranquility, style, and convenience. Be sure to click the virtual tour icon and use your mouse to experience a full 360-degree tour of the sensational backyard and pool area.

140 Hurds Corners Road, Pawling

$655,000

3 Beds ⋅ 3 Baths ⋅ 1041481 MLS

Set on nearly two acres just a few miles from the village of Pawling, this log home offers space, privacy, and real potential for the right buyer. The in-ground concrete pool and detached three-car garage add value rarely found together at this price point. Inside, the open kitchen and vaulted wood ceilings give the home a warm, cabin-like character that is hard to find in newer construction. This home is being sold as is and priced to reflect its current condition and status. The space above the garage is finished but is permitted and approved for storage use only. It is not being represented as legal living space, and any potential alternate use should be independently verified by the buyer with the Town of Pawling. The lower level is currently the subject of an active permit application to be finished, and its status should also be verified directly with the Town prior to closing. A solar panel system is installed on the property but is not currently connected to the grid. Reinstallation and reconnection through Tesla is scheduled, and buyers should confirm current status and any associated costs or timelines directly with Tesla. Given the acreage, the pool, and the bones of this home, there is a lot here for a buyer willing to do some homework. Priced at $655,000 to reflect the property's current condition and open items.

12 Rebecca Drive, Pawling

$589,000

3 Beds ⋅ 3 Baths ⋅ 1037637 MLS

Discover this spacious 3-bedroom, 2.5-bath home ideally located just minutes from the train and downtown Pawling, offering the perfect combination of privacy, convenience, and room to grow. Step inside to an inviting open floor plan designed for comfortable everyday living and entertaining. The first-floor primary suite is a standout feature, offering a generously sized bedroom, private bath, and two large closets for plenty of storage. Enclosed Bonus Porch area with a pellet stove with wall-to-wall windows for endless natural light. The fully finished walk-out basement provides an incredible amount of additional living and entertainment space, complete with a bar area, wood burning stove and direct outdoor access. With plenty of room to customize and enhance, the possibilities are endless for creating a game room, home theater, gym, recreation area, or the ultimate gathering space. Situated on 1.86 acres surrounded by mature trees, the property offers wonderful outdoor space to relax and entertain. Enjoy evenings on the patio or deck while taking in the sunset and peaceful surroundings. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the impressive 1,260-square-foot detached garage, in addition to an oversized attached 2-car garage. With abundant parking and storage, there's room for vehicles, equipment, a workshop, and more. Minutes from the train and downtown yet offering nearly two acres of space, multiple garages, a first-floor primary suite, and a finished walk-out basement—this property offers a rare combination of location, versatility, and potential. Schedule your private showing today!

46 Harmony Hill Road, Pawling

$1,400,000

4 Beds ⋅ 3 Baths ⋅ 1037768 MLS

Set on beautiful grounds next to the Akin Free Library, this one-of-a-kind Colonial offers a rare combination of privacy and charm. The property, including the adjacent BOHA 4 bed parcel, spans 7.48 acres of old-growth trees, a creek, and an open field overlooking Kirby Hill Farm. A gated, tree-lined driveway leads to a home that blends functional living with the timeless character of Quaker Hill.

392 Old Quaker Hill Road, Pawling

$639,000

4 Beds ⋅ 4 Baths ⋅ 1035919 MLS

Set on 3.2 picturesque acres in Pawling NY this meticulously maintained 1960s Colonial has been lovingly built and owned by the same family for many years, and by that family on this land for generations before that. It's a rare offering: a true multi-generational retreat with room to grow. The four-bedroom, two-and-a-half-bath home offers timeless original character throughout, with hardwood floors beneath the carpeting, protected for decades. Features an attached two-car garage and a pull-down attic for extra storage. Sunlight pours through nearly every window, with valley and mountain views on two sides and a view of your private pond on the other. Watch the sunrise and the sunset settle over your own grounds. This property offers sweeping, ever-changing views in every direction all year round. It simply can't be beat. Downstairs, a fantastic finished lower level adding even more living space: a retro-style bar complete with running water, a vintage refrigerator, and a two-burner electric stove, plus a full bathroom, an office, an additional bonus room and a pantry! Beyond the main house, a versatile outbuilding adding exceptional value as it houses an additional one-car garage, storage room, plus a dedicated ~700-square-foot workshop space, currently used for handcrafted Amish furniture-making; it is an ideal spot for a hobbyist, craftsperson, or anyone in need of serious workshop or studio space. And there's more…this offering includes the opportunity to purchase wo additional buildable parcels are available from the same family. MLS and MLS 1037481. Each zoned for a single-family home. Build for extended family, create a private enclave, or invest in future value, all connected to this storied piece of land. You will be surprised to learn that this home is just a few minute ride to the Pawling MetroNorth station to NYC, and the center of town, home to farmers markets, fine dining, coffee shops and boutiques.

3846 Route 55, Pawling

$525,000

3 Beds ⋅ 3 Baths ⋅ 1033232 MLS

Experience refined privacy in this light-filled 3-bedroom, 3-bath Hi-Ranch in a peaceful country setting. This property sits on a beautiful and level 3.19 acres in Pawling, NY, framed by evergreen trees and mature landscaping reflecting a gardener's legacy. The interior reflects a loving family’s touch; it is functional and comfortable, with great potential for modern updates. Its standout location offers easy access to Metro-North, the Taconic State Parkway, NYS Route 22, Route 55, I-84 and I-684 within a short drive. A long driveway, wrought-iron entry gates, a 2-car garage, and a fenced yard enhance privacy. With some work, this home can shine and fully capitalize on its exceptional setting and Pawling location. The main living area features vaulted ceilings, a living room with a pellet stove, an eat-in kitchen with a convenient laundry area leading to a dining room with sliders to a screened-in porch and large deck. There is also a primary bedroom with a full bath and double closets, plus 2 additional bedrooms and a full bath. The lower level offers flexible space with a summer kitchen area and a full bath, ideal for guests or extended family. Nearby, enjoy easy access to village amenities and outdoor recreation, including the Appalachian Trail, the Great Swamp, and Pawling Nature Reserve. This property combines privacy, space, and potential in a sought-after Pawling setting. Schedule an appointment today and start envisioning the possibilities.

66 Reservoir Road, Pawling

$619,900

3 Beds ⋅ 3 Baths ⋅ 1024161 MLS

TO BE BUILT – Build your dream home in the charming Village of Pawling! Ideally located just minutes from downtown Pawling, you'll enjoy convenient access to local shops, restaurants, schools, parks, and the Metro-North train station, making commuting and everyday living a breeze. The homesite is serviced by municipal water and sewer, offering added convenience and peace of mind. Pricing and listing details, such as square footage, bedroom count, etc., is based on LMD’s Bennet model. Looking for something different? Buyers have the opportunity to select from several of our available floor plans and personalize their home with structural options and designer interior finishes to create a space that fits their lifestyle. Whether you're looking for additional living space, a first-floor owner's suite, a gourmet kitchen, or upgraded finishes throughout, our team will guide you through the customization process. Don't miss this opportunity to build a brand-new home in one of Dutchess County's most desirable communities!

Prospect Street, Pawling

$1,199,000

5 Beds ⋅ 4 Baths ⋅ 1010537 MLS

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.

64 S Quaker Hill Road, Pawling

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . 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.