Pawling Homes with Attached Parking features

Welcome to the charming town of Pawling, nestled in the picturesque Dutchess County, New York. Known for its scenic landscapes and tight-knit community, Pawling is more than just a place to live—it's a lifestyle. One of the standout features of this area is its highly regarded school district, which has a reputation for academic excellence and a commitment to fostering a supportive environment for students of all ages. The Pawling Central School District offers a variety of programs designed to cater to diverse learning needs, ensuring that every child has the opportunity to thrive. With dedicated teachers and a focus on innovative teaching methods, parents can feel confident that their children are receiving a top-notch education.

For those looking to call Pawling home, the real estate market offers an array of options, including charming homes with attached parking features. Imagine coming home to a beautifully designed residence, where convenience meets comfort. These homes not only provide easy access to your vehicle but also enhance your living experience by ensuring you’re protected from the elements. Whether you’re a first-time buyer or looking to relocate, Pawling’s real estate options cater to various lifestyles and budgets.

With its blend of small-town charm, quality education, and convenient living, Pawling is an ideal place to settle down and create lasting memories. Explore the opportunities that await you in this delightful community, where every day feels like a breath of fresh air. Your dream home in Pawling is just around the corner!

Newest Pawling Homes with Attached Parking features

$597,500

3 Beds ⋅ 3 Baths ⋅ 1047471 MLS

Welcome Home! You will fall in love with this beautiful, well-maintained Colonial! Relax on the covered front porch, which overlooks lovely park-like property, numerous perennial gardens, mature trees. Special features of this wonderful home are central air, a hard to find 1st floor Primary Suite with an updated full bath and walk-in closet. Off the large foyer is a spacious, warm & inviting Living Rm with hardwood, which is open to an equally inviting Dining Rm, also with hardwood. Fantastic Kitchen has beautiful, ceiling-height cabinets, granite counters, hardwood floor, tons of storage. Great for entertaining, the Kitchen is open to a large, sunny Family Rm, which has a fireplace, hardwood and sliders to a Deck with retractable awning. From the Deck you will enjoy a scenic pond view and the large, level back yard. The first floor offers crown molding, hardwood and an elegant half-bath. Upstairs you will discover a large, beautiful full bath with dual sink vanity & laundry area, two great Bedrooms, plus a Den or Guest Rm with hardwood. This home has been very-well maintained, the driveway is freshly sealed. Large unfinished basement has endless uses! Deerfield Ponds offers the community an inground Pool, Tennis, Basketball court and Clubhouse with Fitness Rm. Right down the road from Deerfield Ponds is Dykeman Farm, known for their delicious corn, tomatoes, more. Pawling is a lovely town which offers a large array of businesses on Route 22 and the picturesque Village, where you will find Metro-North Train Station (Harlem Line), wonderful Restaurants, Pubs, Bakeries, Shops, Clothing Boutique, Book & Antique store, Library, Museums... Dutcher Golf Course is the oldest public course in America! we also have Lakeside Park with sand beach & playground, Daryl's House Music Club & Restaurant, Gyms, so much more! Pawling has 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

$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

$1,475,000

4 Beds ⋅ 5 Baths ⋅ 1029458 MLS

**Do not walk or go to the property without an agent**Set privately on more than 22 acres just minutes from the quaint Village of Pawling, this exceptional country estate captures the essence of Hudson Valley living with breathtaking mountain views, extraordinary privacy, and timeless elegance. Designed for both sophisticated entertaining and comfortable everyday living, this exquisite Colonial showcases refined craftsmanship and beautifully appointed living spaces throughout. A dramatic two-story foyer welcomes you with a sweeping staircase, cathedral ceiling, gleaming ceramic tile flooring, and an elegant chandelier. Bathed in natural light, the gracious living room features a tray ceiling, oversized windows, hardwood floors, and a handsome wood-burning fireplace, while the formal dining room offers rich hardwood flooring, expansive windows, and a tray ceiling, creating an elegant setting for intimate dinners and memorable celebrations. The heart of the home is the open-concept kitchen and family room. The eat-in kitchen boasts abundant cabinetry, granite countertops, stainless steel appliances, recessed lighting, hardwood floors, and a large center island, making meal preparation and casual gatherings effortless. The adjoining sunken family room impresses with soaring ceilings, a dramatic floor-to-ceiling brick fireplace, wet bar, oversized windows, and glass doors leading to a freshly painted deck overlooking beautifully landscaped grounds, mature trees, and peaceful vistas. Whether hosting or enjoying a quiet evening at home, this inviting space offers warmth, comfort, and spectacular year-round views. The first-floor primary suite offers a luxurious retreat with a spa-inspired bath featuring a soaking tub, oversized glass-enclosed shower, dual marble vanities, and generous natural light. A private home office, powder room, laundry room, and access to the oversized three-car garage complete the main level. Upstairs, a spacious bonus room provides endless possibilities as a media room, playroom, library, or additional gathering space. Three generously sized bedrooms with hardwood floors and generous closets are served by two full baths, providing comfortable accommodations for all. The walk-out lower level offers exceptional flexibility with a recreation room featuring a full bar, den with walk-in closet, sitting area, exercise space, game room, full bath, and abundant storage—ideal for multigenerational living, extended guests, or an au pair suite. Beyond the beautifully maintained lawn, the property unfolds into acres of rolling countryside where open meadows, mature trees, and sweeping mountain views create an unforgettable backdrop. The expansive acreage offers endless possibilities for a pool, cabana, gardens, equestrian pursuits, or simply preserving the serenity and remarkable natural beauty that surrounds you. Spectacular sunsets paint the western sky, providing a breathtaking finale to each day. Additional amenities include hardwood flooring, recessed lighting, a generator, brick walkway, storage shed, tray ceilings, decorative columns, transom and bow windows, and dramatic floor-to-ceiling windows that beautifully frame the surrounding landscape. Conveniently located just 90 minutes from New York City with easy access to Metro-North, Routes 22, 311, I-684 and I-84, and just minutes from Thunder Ridge Ski Area, the Harlem Valley Rail Trail, golf, parks, shopping, dining, and the charming Village of Pawling. This extraordinary estate offers a rare opportunity to enjoy refined country living where timeless architecture, breathtaking scenery, and exceptional privacy create an unforgettable Hudson Valley retreat. Whether enjoyed as a full-time residence or an exceptional weekend escape, this is a place where luxury, nature, and tranquility exist in perfect harmony.

7 Herd And Tanner Road, Holmes

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