Pawling Homes with Driveway Parking features

Welcome to Pawling, New York – a charming town nestled in the heart of Dutchess County, where small-town charm meets natural beauty. Known for its picturesque landscapes and vibrant community, Pawling offers a unique blend of rural tranquility and urban convenience. With its rich history, delightful shops, and an array of outdoor activities, Pawling is the perfect place for families, retirees, and everyone in between.

As you explore this delightful town, you'll discover a variety of homes that capture the essence of Pawling living. One standout feature of many properties in the area is driveway parking. Imagine coming home to your own dedicated space, free from the hassle of street parking. Driveway parking not only adds convenience but enhances the overall appeal of your home, making it easier for you and your guests to come and go with ease.

Pawling's real estate market offers a diverse selection of homes, from charming historic houses to modern builds, all with the benefit of driveway parking. This feature is particularly prized in a community where outdoor activities abound, allowing for easy access to your vehicle after a day of hiking the nearby Appalachian Trail or enjoying a picnic at the scenic Lakeside Park.

Whether you’re looking for a cozy starter home or a spacious family residence, Pawling’s homes with driveway parking provide both comfort and accessibility. Come and experience the welcoming spirit of Pawling, where your dream home awaits!

Newest Pawling Homes with Driveway Parking features

$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

$499,000

3 Beds ⋅ 4 Baths ⋅ 1029865 MLS

Versatility, comfort, and an exceptional lifestyle come together in this charming Cape Cod-style home in Pawling Lake Estates, a picturesque lake community nestled atop West Mountain and bordering West Mountain State Forest. Offering 2,188 SF across the first two levels, plus an additional 320 SF finished recreation room in the basement, this thoughtfully designed home features three bedrooms, four full baths, and a flexible floor plan that adapts to your lifestyle. A two-story entry sets the stage for the inviting interior. The main level offers a living room warmed by a pellet stove, a country kitchen with pantry, laundry closet, and dining area with sliding glass doors opening to the expansive walk-off rear deck. A den provides endless possibilities as a family room, home office, formal dining room, or could even be incorporated into the adjacent living room to create a more open layout. Completing the first floor is a full hall bath and a private ensuite bedroom featuring its own bath and two closets, making it an ideal primary suite. Upstairs, the oversized second ensuite bedroom spans from the front to the back of the home and includes two walk-in closets and a private bath. A third bedroom, full hall bath, and a separate study provide additional flexibility for a home office, craft room, recreation space, or whatever best suits your needs. The finished lower level expands the living space with a 320 SF recreation room boasting soaring ceilings. This level also includes a mechanical room, storage closet beneath the stairs, and direct access to the deep two-car garage with high ceilings and a convenient exterior door leading to the driveway, where abundant parking is available. Outdoor living is equally impressive with a sprawling 604 SF back deck overlooking a private, level, park-like backyard. The walk-off deck leads to a lower patio, creating the perfect setting for entertaining, relaxing, or enjoying the peaceful surroundings. Life in Pawling Lake Estates offers a true four-season lifestyle centered around its private, non-motorboat lake. Residents enjoy exclusive access to a sandy beach, docks, clubhouse, recreation area, playground, picnic areas, and year-round community events that foster the neighborhood's nostalgic charm. Spend your summers swimming, fishing, kayaking, paddleboarding, or simply soaking in the natural beauty. Beyond the community, you’ll find the Appalachian Trail, Lakeside Park, and the Dutchess Rail Trail via its newly completed connector just minutes away. Golf enthusiasts will appreciate nearby Dutcher Golf Course, while the quaint Village of Pawling offers boutique shopping, fun eateries, fine dining, a seasonal farmers market, and Metro-North service with an approximately 90-minute commute to New York City.

22 Hickory Lane, 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

$899,000

4 Beds ⋅ 4 Baths ⋅ 1015365 MLS

Beautifully situated on 5.5 private acres, this impressive home offers a gated entrance and a long private driveway leading to breathtaking mountain views and a peaceful setting. Relax on the charming rocking-chair front porch and enjoy the serenity of the surrounding landscaped front lawn. Step inside to a dramatic two-story foyer and an abundance of natural light. The spacious kitchen features granite countertops, ample cabinetry, and large windows that showcase the scenic mountain views and doors out to trex decking. Adjacent to the kitchen is a comfortable family room with access to the laundry room and the attached 3-car garage. A formal dining room and formal living room provide excellent spaces for entertaining, while numerous windows throughout the home bring the outdoor in. The main level also includes a convenient half bath. upstairs, the elegant staircase leads to the expansion primary suite that you enter through double doors. The primary bath features a jacuzzi, separate shower, and dual vanities, creating a private retreat. Additional 3 more bedrooms, one with its own bathroom. And one more bonus on the top floor enjoy your oversized great room down the hallway. Basement is waiting to be finished with 10 ft ceilings, a walk-out double door and regular size windows. 4.4 miles to Metro North and the Village of Pawling. Dover Schools. CT border is just down the road. Full house generator. Original Owners. "90 minutes from Manhattan.Mountain views. Work remotely, escape every weekend."

128 Old Pawling Road, 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

$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

$629,900

3 Beds ⋅ 2 Baths ⋅ 992269 MLS

Super Charming Cape On An Ultra Private 2.92 Acres At The Very End Of The Dead End Street! Close To Everything -- Shopping, Schools, Train Station/Commuting, Restaurants And Still Be Tucked Into Your Own Private Haven. Flexible Floor Plan To Create Rooms For You --- Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side. Current Owners Created His & Hers Living Rooms. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Ready For Your Ideas Without Having To Start With Unfinished Space. Very Flexible Space! Both Bedrooms In The Upper Level Are Very Large and The House Has Room To Grow As Your Spatial Needs Grows -- Bedroom On The Left Has 2 Very Deep Areas Currently Unfinished But Being Used As 2 Walk-In Closets. However, When It's Time To Grow Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Summers Are The Best While Enjoying The South Facing Deck Off The Kitchen That Leads To The In-Ground Pool In The Backyard. Excited To Host Summer BBQs & Pool Parties? You Could Pack + or -- 50 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, A Camper / RV, OR For Those Fantastic Summer Parties! To The Left Of The House Is Included In The <3 Acres & Its 1 Acre Of Land That Is Part Of The Privacy. It Could Be Turned Into An Additional Detached Garages, Cute Cottage To Rent Full or Part Time (Abnb) or House an In-Law, A Garden With A Garden Potting Shed, A Work Shop, Or Whatever Your Vision Can Imagine. Cozy Up To The Fire In The Winter OR The Summer's Sun & Moon's Reflection From The Salt Water Pool As You Enjoy Your Morning Coffee & Your Evening's Glass Of Wine. Come! Relax, Unwind, & Enjoy Life!

57 Buhleir Road, Pawling

$14,995,000

4 Beds ⋅ 4 Baths ⋅ 965662 MLS

Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct access to the OTA. The stunning equine compound is presided over by a circa 1860 main estate, masterfully renovated boasting 3,942 SF, 4 bedrooms, 4 bathrooms, 9 rooms, with an in-ground pool. Designed for year-round riding, training, and boarding indoors and out. With barns, indoor and outdoor rings all developed for the unique training needs for dressage, hunter-jumper, and polo. The main barn has 32 12' x12' stalls, center aisle, matted stalls, yoked windows, fire suppression system, automatic fly control system, climate-controlled tack room with kitchen and bathroom, feed storage, office and viewing room, bathrooms, 2 hot water wash stalls with heat lamps, 4 grooming stalls, hay loft with drop to each stall, and hay conveyor. An attached 200' x 90' indoor riding ring with equestrian sand with fiber footing, sound system, and retractable windows. Adjacent to the indoor, a 220' x 100' outdoor jumping ring and a 200' x 80' outdoor dressage ring. The second largest barn has 27 12' x 12'stalls, with a 200' x 90' indoor riding ring, and a 220' x 100' outdoor jumping ring with TraveLite dust free footings. The polo barn has 14 10' x 14' yoked stalls. The pony barn has 8 10' x 12' stalls and a fire suppression system. Buildings and additional structures on the property include a gated entry and guard house, manager's house, and a renovated barn, now a stylish clubhouse, which can accommodate up to 60 people with a fireplace, full kitchen and bathrooms, a 2-bedroom apartment above and a manager's office attached. A 3-bedroom, 4 bath cape cod guest house with tennis/basketball court. 3 1-bedroom guest cottages with thatched roofs. Groom quarters, equipment barn, fire suppression building with a 50,000 gallon underground water detention tank. Automatic hot-walker for horse conditioning. Wedding barn to host special events, 15 events a year, up to 120 guests. Boma outdoor BBQ area, skeet and trap range and helipad. For those looking to build another unparalleled estate, a homesite foundation exists with an infinity edge pool with the most sublime views. Additional features include 3 ponds on the property, judges and viewing gazebos, 2-week hay storage, irrigation systems, 3 generators, 7 wells, 7 septics, and 1 fire hydrant. Two parcels, 76-acres and 171-acres create this pastoral perfection in the heart of the Hudson Valley. This premier equestrian venue presents a truly remarkable opportunity just minutes to the Village of Pawling, a quaint upstate, bucolic 18th century village. The charming village offers fine dining, fun eateries, boutique shops, antique stores, cultural attractions and a seasonal farmer's market. Pawling has its very own Metro North station stop, just 90 minutes by train or car to NYC.

15 Kirby Hill Road, Pawling

$1,250,000

5 Beds ⋅ 5 Baths ⋅ 811617 MLS

New construction 4 bedroom, 4.5 bathroom home on 5 acres. Don't miss this opportunity to customize your dream home. This home features a open floor plan with large kitchen, perfect for entertaining. The main living area has exposed beams and high ceilings. The primary bedroom has large walk in closet and ensuite. There is also a junior suite with ensuite. See attached floor plans for full detail. Great location, close to town of pawling, train station, dining and more! Pictures shown are from previous new builds to show style of home with exposed beams, etc.

120 Harmony Road, Pawling

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