Pawling Homes with Oversized Parking features

Welcome to Pawling, New York, a charming town nestled in the heart of Dutchess County. Known for its picturesque landscapes and vibrant community, Pawling offers an exceptional quality of life, making it an ideal place for families and individuals alike. One of the standout features of this area is its highly regarded school district, which is dedicated to fostering academic excellence and personal growth. The Pawling Central School District is committed to providing a supportive and enriching environment for students, with a strong emphasis on innovative teaching methods and extracurricular activities that promote well-rounded development.

For those seeking a home in this delightful town, you'll be pleased to discover a variety of properties equipped with oversized parking features. Whether you have multiple vehicles, enjoy hosting family gatherings, or simply want extra space for your hobbies, these homes cater to your needs. Imagine coming home to a spacious driveway that accommodates your cars, RVs, or even a boat, providing you with the ultimate convenience and peace of mind.

Living in Pawling not only means having access to excellent educational opportunities but also enjoying the comforts of a home designed to fit your lifestyle. With its charming downtown, scenic parks, and a strong sense of community, Pawling is more than just a place to live; it’s a place to thrive. Explore the possibilities of finding your dream home here, where oversized parking is just one of the many features that enhance your living experience. Welcome to Pawling—where your ideal home awaits!

Newest Pawling Homes with Oversized Parking features

$655,000

3 Beds ⋅ 3 Baths ⋅ 1041481 MLS

Set on nearly two acres just a few miles from the village of Pawling, this log home offers space, privacy, and real potential for the right buyer. The in-ground concrete pool and detached three-car garage add value rarely found together at this price point. Inside, the open kitchen and vaulted wood ceilings give the home a warm, cabin-like character that is hard to find in newer construction. This home is being sold as is and priced to reflect its current condition and status. The space above the garage is finished but is permitted and approved for storage use only. It is not being represented as legal living space, and any potential alternate use should be independently verified by the buyer with the Town of Pawling. The lower level is currently the subject of an active permit application to be finished, and its status should also be verified directly with the Town prior to closing. A solar panel system is installed on the property but is not currently connected to the grid. Reinstallation and reconnection through Tesla is scheduled, and buyers should confirm current status and any associated costs or timelines directly with Tesla. Given the acreage, the pool, and the bones of this home, there is a lot here for a buyer willing to do some homework. Priced at $655,000 to reflect the property's current condition and open items.

12 Rebecca Drive, Pawling

$589,000

3 Beds ⋅ 3 Baths ⋅ 1037637 MLS

Discover this spacious 3-bedroom, 2.5-bath home ideally located just minutes from the train and downtown Pawling, offering the perfect combination of privacy, convenience, and room to grow. Step inside to an inviting open floor plan designed for comfortable everyday living and entertaining. The first-floor primary suite is a standout feature, offering a generously sized bedroom, private bath, and two large closets for plenty of storage. Enclosed Bonus Porch area with a pellet stove with wall-to-wall windows for endless natural light. The fully finished walk-out basement provides an incredible amount of additional living and entertainment space, complete with a bar area, wood burning stove and direct outdoor access. With plenty of room to customize and enhance, the possibilities are endless for creating a game room, home theater, gym, recreation area, or the ultimate gathering space. Situated on 1.86 acres surrounded by mature trees, the property offers wonderful outdoor space to relax and entertain. Enjoy evenings on the patio or deck while taking in the sunset and peaceful surroundings. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the impressive 1,260-square-foot detached garage, in addition to an oversized attached 2-car garage. With abundant parking and storage, there's room for vehicles, equipment, a workshop, and more. Minutes from the train and downtown yet offering nearly two acres of space, multiple garages, a first-floor primary suite, and a finished walk-out basement—this property offers a rare combination of location, versatility, and potential. Schedule your private showing today!

46 Harmony Hill Road, Pawling

$619,900

3 Beds ⋅ 2 Baths ⋅ 992269 MLS

Incredibly Private & Charming Home On 2.92 Acres At The Very End Of The Dead End Road! Updated Kitchens & Baths in 2013-14 & 2025 With An Expansive Kitchen That Has Amazing Storage, Granite Countertops, 7 Foot Island w/ Even More Cabinets, and Newer Stainless Appliances. This Home Has MEGA Possibilities -- Airbnb, Potential In-Law or Both (on the side of the property & in the basement), Additional Detached Garages With Or Without a Business Office. Looking To Have A Work Shop? A Garden Or A Mini Farm? A Garden Potting Shed? Flowers OR Vegetables OR Fruit Trees? There Is Plenty Of Sun Including Space To Plant Whatever Your Heart Desires And Whatever Your Vision Can Imagine! -- A Home To Create Your Dream! Build An Adjacent Supplemental Home On The Space To The Left Of The House, Which Is Part Of The Almost 3 Acres. OR Easy Ideas In The Already Finished Basement. Live For Free OR Almost Free. The Parking Is Ideal For A Contractor or Contracting Company With All The Extra Parking and Pull Off Areas and Commercial Zoning (HB Zone) OR Someone With A Boat, Jet Skis w/ Trailers. Park + or -- 30 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, Camper / RV, OR For Those Fantastic Summer Parties! This Private Haven Is Close To Everything And Room For All -- Shopping, Schools, Train Station/Commuting, Restaurants AND Still Be Home In 5 To 10 Minutes. Flexible Floor Plan To Create Rooms For You --- A 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 But Either Of These Rooms Could Become Something Else. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Also Ready For Your Ideas Without Having To Start With Unfinished Space. Both Bedrooms In The Upper Level Are Large and Check Out Those Unique Hardwood Floors! The House Has Room To Grow As Your Spatial Needs Grows -- The 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, The Upstairs Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Excited To Host Summer BBQs & Pool Parties? There is Plenty Of Room! Enjoy The Summer's Sun OR Moon's Reflection From The Salt Water Pool As You Sip Your Morning Coffee OR Your Evening's Glass Of Wine -- On The Deck Or On The Pool's Patio. Then, Cozy Up To The Fire In The Fall & Winter. Come! Relax, Unwind, & Enjoy Life! This Is The Perfect Home!

57 Buhleir Road, Pawling

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