24 Overlook Drive • Pawling, NY 12564

$689,000 Beds: 3 • Baths: 3 full 1 partial • Sq. Feet: 3175 • MLS ID: 995102 • Subdivision:School Dist: Pawling
Tucked away on nearly two private acres, this inviting and versatile home offers the perfect balance of everyday comfort and refined country living-just down the street from the heart of Pawling and less than five minutes to Metro-North via the Harlem Line, allowing for an easy commute to the city. Thoughtfully designed as a 3-bedroom home that lives like a 4-bedroom, the layout adapts naturally to today's lifestyle. The main level features two generously sized bedrooms, along with a flexible third room ideal as a home office, playroom, or additional bedroom, complemented by 1.5 baths. Completing the first floor, the updated kitchen finished with granite countertops flows effortlessly into the living room and opens to a spacious screened-in porch, creating a seamless indoor-outdoor connection optimized for both everyday living and long summer evenings. Upstairs, the primary suite spans the entire floor, providing a private, oasis-like setting with abundant natural light, large walk-in closet and its own en suite bath. On the lower level, the heated, finished walk-out adds exceptional functionality with extra storage options, a bar and lounge area, pellet stove, full bath, and an ideal setup for entertaining, guest quarters, or extended living. The outdoor living space is equally compelling, with Trex decking overlooking 1.95 acres of park-like grounds-providing the peace and tranquility so many are seeking. An attached two-car garage, storage shed, and oversized driveway with a roundabout complete the offering. With a few modern touches, this property can be elevated into something truly special-your own private retreat with the best of both worlds. Conveniently located near shops, dining, schools, and the train, this home presents a rare opportunity to enjoy both accessibility and escape. Don't miss this one! View this listing at: http://philiplaffey.laffey.com/mls=995102

Property Features

  • Garage: 2
  • Taxes: $14,389
  • Basement: Yes
  • Wooded: Yes
  • Exterior: Frame
  • Lot Size: 1.95 Acres
  • Heating: Baseboard,Forced Air,Oil
  • Cooling: Central Air
  • Year Built: 1964
  • Fireplaces: 1
  • Water: Well
  • Sewer: Septic Tank
  • On Market Date: 2026-05-07
  • Appliances: Cooktop,Dishwasher,Dryer,Exhaust Fan,Freezer,Gas Cooktop,Gas Oven,Microwave,Refrigerator,Washer
  • Basement: Finished,Full,Storage Space,Walk-Out Access
  • Exterior Features: Playground
  • Fireplace Features: Pellet Stove
  • Fireplace Y/N: Yes
  • Flooring: Hardwood,Laminate,Tile
  • GarageY/N: Yes
  • Interior Features: First Floor Bedroom,First Floor Full Bath,Breakfast Bar,Ceiling Fan(s),Chefs Kitchen,Double Vanity,Eat-in Kitchen,Entrance Foyer,Granite Counters,Open Floorplan,Primary Bathroom,Storage,Walk-In Closet(s)
  • Laundry: In Basement
  • Lot Features: Back Yard,Front Yard,Level,Near Golf Course,Near Public Transit,Near School,Near Shops,Private,Views,Wooded
  • Attic: Pull Stairs
  • Number Of Kitchens: 1
  • Heating Zones: 3
  • Other Structures: Shed(s)
  • Parcel Number: 134089-6956-00-471704-0000
  • Parking Features: Attached,Driveway,Garage,Oversized,Private
  • Parking Total: 20
  • Patio And Porch: Covered,Deck,Patio,Porch,Screened
  • Rental Term: Monthly
  • Rooms Total: 8
  • Skylight: Y
  • Utilities: Electricity Connected,Trash Collection Private
  • Window Features: Blinds,Double Pane Windows,Insulated Windows,Oversized Windows,Skylight(s),Wall of Windows

School Information

  • High School: Pawling High School
  • Middle School: Pawling Middle School
  • Elementary School: Pawling Elementary School
  • School District: Pawling
Printed May 10, 2026


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