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Pawling, New York

Pawling, New York, Equestrian Properties

Made up of unique homes, sprawling vistas and a quaint town village, Pawling, New York is an abundant community. Resting in the foothills of the Berkshires and nestled between the Connecticut border and I-84, Pawling offers close proximity to interstate corridors and the convenience of two Metro-North train stations.

Located at the southern-most corner of New York’s Dutchess County, Pawling is a welcoming town, from the landscape and the locally owned shops right down to the residents. This is the epitome of small-town America. Although the town of Pawling spans a significant amount of land there are less than 10,000 residents here allowing for privacy.

Beautiful Country Life

While Putnam County is often referred to as the county where the country begins, Dutchess County exemplifies the progression of country life. Residents and visitors alike can find an array of opportunities to play outdoors including The Edward R Murrow Park, Lakeside Park with its sandy beach and swimming, The Nature Conservancy, and Ducher Golf Course, which is the oldest municipally owned course in the US.

All told, Pawling boasts two lakes and over 300 acres of accessible park land in addition to The Great Swamp, a 6000-acrea protected wetland and wildlife sanctuary. The Great Swamp traverses through Pawling and connects with The Appalachian Trail. Traveling from Maine to Georgia. The Appalachian Trail is famous for hiking although it can take most people roughly 6 months to cover the entire footprint. For those who prefer to simply enjoy the scenery for a few hours, the trail has several access points throughout Pawling which allow visitors to take in the beauty from the wetlands to the fields to the rivers and to the mountains.

Quaker Hill

Pawling is a fairly varied town; the majority of the local communities are close-knit and rather small. Quaker Hill for instance features larger homes and beautiful mountain-side properties. A peaceful suburb in Pawling, Quaker Hill is best known for horse farms, historic equestrian and country estates and the overall landscape. If you are looking for luxury estates in Dutchess County, horse farms in Pawling, NY or horse properties in Pawling, NY then Quaker Hill might be the perfect location to start your new home search.

With the Hudson River in the background and the panoramic landscape, Quaker Hill is one of the best places to enjoy the breathtaking views of Dutchess County. In close proximity to vineyards, restaurants, farmers markets and antique shops, Quaker Hill is located in the southern portion of the state which is referred to as “The Oblong” and is located on a twelve-mile-long ridge from which it borrows its name.

Equestrians Love It Here

Crisscrossing through Quaker Hill is the equestrian trail system, known as the Oblong Trail Association or the OTA. Formed in 2000, the OTA was created in effort to encourage both nature walking and equestrian activities. Rounding out the offerings in Pawling, NY are the community theater, a top-notch public and private school system and a myriad of community events.

The welcome mat is always out in Pawling so come explore this compelling community and see why you’ll soon be calling Dutchess County home.

Search for the Perfect New York Home


Shaylene found us the perfect home for our horses.

Shaylene is very knowledgeable of the Connecticut horse properties and she was very helpful in finding the right place for us. It was great pleasure to work with her throughout the transaction and keep in touch afterwards.

Bobby Tanev

Shaylene made the entire process stress-free.

Shaylene is the consummate professional.  She seeks to find the house that you are looking for, works hard but is never pushy. We worked with Shaylene for about 7 months and viewed a few houses with her that fit our criteria but were not perfect. One day she reached out to us with the perfect… Read more “Shaylene made the entire process stress-free.”

Susan & Frank McDermott

Finding a home you love with a barn is challenging.

My husband and I have been working with Shaylene to purchase a home that would allow us to have our horses at home. I really can’t say enough good things about her. She is personable, knowledgeable, endlessly patient, and incredibly generous with her time. She answers all our questions and is helping us to understand… Read more “Finding a home you love with a barn is challenging.”

Maria & Gary

We found our beautiful horse farm in Connecticut.

Just want to give a shout out to Shaylene Neumann on helping us find our beautiful horse farm in CT. Shaylene is a lifelong resident as well as growing up in the real estate industry and being an equestrian herself was most supportive in knowing what we were looking for and just how to find… Read more “We found our beautiful horse farm in Connecticut.”

Joan States

We were very particular customers…

We couldn’t be happier with the dream summer home Shaylene helped us we find on Candlewood Lake. I can say we were very particular customers and Shaylene thoroughly covered the landscape of options and presented great opportunities to us. It was also not an easy negotiation. Shaylene helped us get the best terms and price… Read more “We were very particular customers…”

John & Angie Dietrich