Pawling Homes with Heated Garage Parking features

Welcome to Pawling, NY – a charming town nestled in the heart of Dutchess County, where community spirit meets picturesque landscapes. Known for its rich history and vibrant local culture, Pawling is not just a place to live; it's a place to thrive. One of the standout features of this delightful area is its exceptional school district, which is renowned for its commitment to academic excellence and holistic development. Pawling Central School District prides itself on providing a nurturing environment where students are encouraged to explore their interests and reach their full potential. With a range of extracurricular activities, dedicated educators, and a focus on innovative teaching methods, families can rest assured that their children are receiving a top-notch education.

In addition to its educational offerings, Pawling boasts a variety of homes that cater to the needs of modern families. Among these, you'll find residences featuring heated garage parking – a luxurious convenience that adds an extra layer of comfort during the chilly winter months. Imagine coming home to a warm, inviting space where your vehicle is protected from the elements, allowing you to step out into a cozy home without the hassle of scraping ice off your windshield.

Whether you are drawn to the scenic beauty, the strong sense of community, or the excellent schooling options, Pawling is the perfect place to call home. Explore the real estate opportunities that await you in this enchanting town, and discover why so many are choosing to make Pawling their forever home.

Newest Pawling Homes with Heated Garage Parking features

$1,799,000

5 Beds ⋅ 6 Baths ⋅ 875119 MLS

A Quintessential Quaker Hill Estate with Guest Cottage Perched atop the storied hills of Quaker Hill, this exceptional five-acre estate embodies the romance and elegance of country living at its finest. Privately nestled amid sweeping meadows, renowned equestrian properties, and grand country estates, 43 Meeting House Road offers a rare combination of exclusivity, beauty, and refined luxury just 90 minutes from Manhattan. Thoughtfully reimagined from its original log-home roots, the residence seamlessly blends timeless character with sophisticated modern design. Wide-plank oak floors, gracious entertaining spaces, a sunlit library, and a beautifully appointed chef's kitchen with radiant-heated floors and an oversized island create an atmosphere of effortless elegance. The luxurious primary suite is a retreat unto itself, with soaring 18-foot ceilings, skylights, and a Juliet balcony overlooking rolling lawns, mature specimen plantings, and the pastoral landscape beyond. Additional ensuite bedrooms and flexible living spaces provide exceptional comfort for family and guests. Designed for an elevated indoor-outdoor lifestyle, the estate is surrounded by sweeping lawns ideal for grand-scale outdoor entertaining, garden parties, and relaxed afternoons in the countryside. Expansive decks overlook a tranquil spring-fed pond, while the resort-inspired pool area, complete with cabana, bar, and bath, evokes the atmosphere of a private countryside club. Every detail has been curated for comfort and convenience, from whole-house generators serving both residences and a heated two-car garage to integrated Sonos audio, security systems, advanced climate control, and state-of-the-art connectivity. Enhancing the estate is a beautifully renovated and completely independent two-bedroom guest cottage. Featuring its own kitchen, fireplace, lofted living area, utilities, and septic system, it offers luxurious accommodations for guests, extended family, staff, or a private home office. Rarely does a property combine such privacy, sophistication, and natural beauty. One of Quaker Hill's most compelling offerings, this remarkable estate is a turnkey country sanctuary where sweeping lawns, resort-caliber amenities, and timeless elegance create an unparalleled retreat.

41 and 43 Meeting House 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.