Pawling Homes with Pool Amenities

Welcome to Pawling, New York—a charming town nestled in the picturesque Dutchess County. Known for its rich history and natural beauty, Pawling offers a serene escape from the hustle and bustle of city life while still being conveniently located just a short drive from metropolitan areas. With its quaint downtown, vibrant community events, and stunning landscapes, Pawling is a perfect blend of small-town charm and modern amenities.

One of the most appealing features of homes in Pawling is the availability of properties with pool amenities. Imagine spending your summer afternoons lounging by your own private pool, surrounded by lush greenery and the soothing sounds of nature. These homes provide the ultimate oasis for relaxation and entertainment, perfect for hosting family gatherings or enjoying a tranquil evening under the stars.

Properties with pool amenities in Pawling come in various styles and sizes, catering to diverse tastes and lifestyles. Whether you’re looking for a cozy cottage or a spacious family home, you’ll find options that fit your needs while offering the luxury of a private pool.

Beyond the allure of your own backyard retreat, Pawling boasts an array of outdoor activities, including hiking trails, parks, and nearby lakes, making it an ideal location for nature enthusiasts. With a strong sense of community and a wealth of recreational opportunities, Pawling is not just a place to live—it's a place to thrive. Discover the charm of Pawling and the joy of owning a home with pool amenities today!

Newest Pawling Homes with Pool Amenities

$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

$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

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