Pawling Homes with Pawling School district

Welcome to Pawling, New York – a charming town nestled in the heart of Dutchess County. Known for its picturesque landscapes and vibrant community spirit, Pawling offers a unique blend of small-town charm and modern amenities. With its rich history dating back to the 18th century, Pawling boasts a quaint downtown area filled with delightful shops, cozy cafes, and a range of dining options that cater to every palate.

One of the standout features of Pawling is its commitment to education, highlighted by the highly regarded Pawling School District. Families looking to settle in this idyllic town will appreciate the district’s dedication to providing quality education, fostering a nurturing environment for students from kindergarten through high school. The schools are known for their strong academic programs, dedicated staff, and a wide array of extracurricular activities that encourage personal growth and community involvement.

Real estate in Pawling is as diverse as its residents. From charming historic homes to modern developments, there’s something for everyone. Many properties are situated on spacious lots, offering beautiful views and a sense of tranquility. Whether you’re searching for a cozy cottage or a contemporary family home, you’ll find a welcoming community that feels like home.

Outdoor enthusiasts will love Pawling’s proximity to nature, with numerous parks, hiking trails, and the scenic Appalachian Trail just a stone’s throw away. With its blend of natural beauty, strong community values, and excellent schools, Pawling, NY, is the perfect place to plant your roots and create lasting memories. Discover your dream home in Pawling today!

Newest Pawling Homes with Pawling School district

$699,000

3 Beds ⋅ 3 Baths ⋅ 1029600 MLS

A rare Pawling hilltop retreat with panoramic views & endless potential! Opportunities like this are extraordinarily hard to come by. Perched high to capture breathtaking, miles-long panoramic vistas, this true "sunset house" offers an idyllic Hudson Valley lifestyle centered around big skies, rolling hills, and complete tranquility. Imagine sitting on the expansive covered patio with your favorite beverage looking out into the vibrant sunset, or lounging by the crystal-clear in-ground pool, sunbathing while overlooking nearby farms and sparkling lakes. This property was built for unforgettable outdoor living and limitless entertaining. Inside, the home is a clean-cut, light-filled ranch featuring three bedrooms and two-and-a-half bathrooms. The expansive living room serves as the heart of the home with its classic brick wood-burning fireplace, two huge picture windows framing the valley skyline, and sliding glass doors that open directly onto the massive patio. Adjacent, the kitchen is outfitted with high-end cabinetry and modern stainless steel appliances, opening seamlessly to a bright dining area framed by another impressive picture window. The primary bedroom offers its own private half bath, while a hallway closet conveniently houses the main-level laundry. Downstairs, the finished walk-out basement expands your living space with two versatile rooms perfect for a home theater, gym, or guest quarters, complemented by a full bathroom and abundant storage space. Spanning over 4.5 acres, the grounds offer exceptional privacy along with rare long-term flexibility. Whether you envision expanding the existing home or exploring options to subdivide and sell or build a second residence, this property delivers a quintessential Pawling sanctuary where indoor ease meets endless horizon.

21 Overlook Drive, Pawling

$175,000

1022374 MLS

Beautiful Private 6.4-Acre Lot in the Town of Pawling – Build Your Dream Home, Discover the perfect setting for your dream home on this beautiful, private 6.4-acre parcel in the desirable Town of Pawling. Offering peace, privacy, and a picturesque natural setting, this property is an exceptional opportunity to create your own country retreat while remaining close to the conveniences of town. Just minutes away is Metro North Train Station in the charming Village of Pawling. The village features a variety of restaurants, pubs, boutique shops, and seasonal attractions, including the popular summer farmers market. Golf enthusiasts will enjoy the Dutcher Golf Course, while Lakeside Park offers swimming, scenic walking trails, and picnic areas for outdoor recreation. For nature lovers, the renowned Appalachian Trail is nearby, providing miles of hiking and breathtaking views. During the winter months, Thunder Ridge Ski Area offers skiing and snowboarding just a short drive away. Experience the best of country living with easy access to year-round recreation, local amenities, and small-town charm.

Woodin Lane, Pawling

$360,000

2 Beds ⋅ 3 Baths ⋅ 1028659 MLS

This immaculate, 1,413 SF 2 bedroom, 2 1/2 bath townhome sits in the highly sought-after Cedar Valley development, less than a mile from the charming Village of Pawling. Residents here enjoy a wonderful array of amenities, including a clubhouse, inground pool, and four brand-new pickleball courts, all within a community that perfectly balances privacy and convenience. Step inside to a welcoming entry with a vaulted ceiling that sets a spacious tone. The main level flows effortlessly into an expansive open-concept living and dining area—one massive, light-filled room anchored by French doors that open to a stone patio. Beyond the patio, mature woods create a serene, natural backdrop that feels worlds away from everyday hustle. The country kitchen is warm and functional, featuring updated appliances, generous cabinetry and counter space, a convenient pantry, and a pass-through window to the dining area. A double window bathes the space in sunlight, offering the perfect spot for a breakfast table. A powder room and mechanical closet complete the thoughtfully laid out first floor. Upstairs, the primary bedroom suite provides a peaceful retreat with a large walk-in closet and an attached bath boasting a walk-in shower and linen closet. The nicely sized second bedroom offers its own attached full bath with a fitted tub. Between the two bedrooms, the washer and dryer are tucked away for everyday convenience, while pull-down attic stairs provide excellent additional storage. The home also includes two unassigned parking spots with parking available in front of the complex. Located less than a mile from the heart of the Village of Pawling, this residence puts boutique shops, fine dining, casual eateries, pubs, and the seasonal farmers market right at your fingertips. Outdoor enthusiasts will love easy access to Lakeside Park, Pawling’s town park, the Appalachian Trail, and the Dutchess Rail Trail via the newly completed connector. Golf lovers will appreciate Dutcher Golf Course just across the road. Best of all, the Pawling Metro-North station is only a little over a mile away, offering a convenient 90-minute commute to NYC. This townhome truly delivers the ideal blend of modern comfort, community amenities, and an unbeatable Hudson Valley lifestyle.

16 Evergreen Way, Pawling

$365,000

3 Beds ⋅ 3 Baths ⋅ 1026446 MLS

Spacious and affordable. This expansive ranch style home sits on an approximately 3 acres that feature beautiful mountain views from the back of the home. Due to the layout of the home the possibilities are nearly endless. It currently sits as a 3 bedroom and 3 bath home but with proper approvals additional bedrooms are possible. The are two garages on the property. The garage next to the house can fit 2 cars and a second garage behind the house can accommodate 1 car or yard equipment, etc. The price of this home reflects the need for some sweat equity in the form of a deep clean and interior paint job. With a bit of effort this home will sparkle. As an added bonus, there are approximately 97 acres held by the same owner that are contiguous to the parcel on which the house sits. That acreage can be rolled into a package deal or it will be sold off separately. Multiple offers received. Please submit highest and best offers by noon on Thursday 7/23/26

357 W Dover Road, Pawling

$575,000

3 Beds ⋅ 2 Baths ⋅ 1022255 MLS

Welcome to 17 Spring Street, a beautifully maintained 1890 Victorian in the heart of the Village of Pawling. Rich in character and timeless charm, this inviting home features hardwood floors, crown molding, and a classic rocking chair front porch. The bright Living Room opens to an elegant Dining Room with bow windows, hardwood floors, chair rail, and a chandelier, creating the perfect setting for gatherings. Just off the Dining Room is a spacious Laundry Room with custom built-ins, abundant storage, and a full bath with a walk-in shower. The generously sized Kitchen offers plenty of workspace, a corner breakfast bar, and access to a mudroom/enclosed porch leading to a private rear patio.Upstairs, you'll find three bright bedrooms with hardwood floors, including a spacious primary bedroom with a walk-in closet. A beautifully appointed hall bath features a classic claw-foot tub and a separate walk-in shower. Additional highlights include a one-car garage, storage shed, and a private backyard. Ideally located within walking distance to the Pawling Village shops and restaurants, Metro-North, parks, and more, this charming Victorian offers the perfect blend of historic character and everyday convenience.

17 Spring Street, 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

$375,000

2 Beds ⋅ 1 Baths ⋅ 1020651 MLS

Welcome to 28 Birch Terrace, a charming 2-bedroom, 1-bath Ranch nestled on a private 0.79-acre cul-de-sac lot in the sought-after Pawling Lake Estates community. This move-in ready home features beautifully refinished hardwood floors throughout the Living Room, Dining Area, and bedrooms. The bright Kitchen offers new quartz countertops (2026), tiled floors, and a convenient washer and dryer. Enjoy the sun-filled enclosed sunroom overlooking the peaceful backyard, perfect for relaxing year-round. The full bathroom includes a tub, and recent updates provide peace of mind, including a newly paved driveway (June 2026), propane furnace (2019), and new gutters (2025). Pawling Lake Estates residents enjoy access to a private beach, clubhouse, and dock, all surrounded by approximately 800 acres of protected New York State land, offering endless opportunities for hiking, fishing, kayaking, and enjoying nature. A wonderful year-round home or weekend retreat!

28 Birch Terrace, Pawling

$1,235,000

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

$600,000

4 Beds ⋅ 3 Baths ⋅ 945476 MLS

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.

5 Red Tail Court, Pawling

$3,100,000

3 Beds ⋅ 3 Baths ⋅ 1005064 MLS

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.

809 QUAKER HILL Road, Pawling

$2,250,000

1005925 MLS

Exceptional opportunity to own one of the most versatile and prestigious office properties in the Pawling market. Located at 515, 517 & 527 Route 22, this premier office campus offers over 11,000 SF of professional space on nearly 2 acres in a highly visible Route 22 location. Designed for flexibility and growth, the property features three levels with entrances and exits on all four sides, allowing for multiple occupancy configurations, private business operations, or a combination of owner-user and income-producing tenancy. The building offers an impressive mix of executive offices, conference rooms, kitchens, private and shared restrooms, reception areas, and multiple storage spaces above and below grade. High-end finishes, exceptional natural light, and thoughtful floor plans create an ideal environment for professional, medical, corporate, educational, creative, or administrative users. Separate utility services and multiple access points support easy subdivision and independent operation of various sections of the property. Well suited for an owner-user seeking to occupy a significant portion while generating income from additional tenants, the property also presents an outstanding investment opportunity with the ability to create multiple revenue streams. Ample parking, exterior yard areas, expansion potential, and excellent traffic exposure further enhance its appeal. Conveniently located within walking distance of shopping, restaurants, schools, and Metro-North rail service, this landmark property offers the rare combination of immediate functionality, future expansion potential, and long-term investment value. One of the most adaptable and expandable office campuses available in the Pawling submarket. Call for pricing, floor plans, and occupancy details.

527 Route 22, Pawling

$5,000,000

8 Beds ⋅ 13 Baths ⋅ 968589 MLS

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.

618 Quaker Hill Road, Pawling

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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.