24 Overlook Drive, Pawling, NY

$689,000

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3

Beds

4

Baths

3,175

Square feet

1.95

Acres

About 24 Overlook Drive

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!

Features of 24 Overlook Drive

MLS® # 995102
Price $689,000
Sold Price $735,000
Date Sold July 21st, 2026
Bedrooms 3
Bathrooms 4.00
Full Baths 3
Half Baths 1
Square Footage 3,175
Acres 1.95
Taxes $14,389
Year Built 1964
Type Residential
Sub-Type Single Family Residence
Style Contemporary
Status Closed

Community Information

Address 24 Overlook Drive
City Pawling
County Dutchess County
State NY
Zip Code 12564
Adult 55+ Community No

Amenities

Utilities Electricity Connected, Trash Collection Private
Parking Spaces 20
Parking Attached, Driveway, Garage, Oversized, Private
# of Garages 2
Is Waterfront No
Has Pool No

Interior

Interior Hardwood, Laminate, Tile
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)
Appliances Cooktop, Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Cooktop, Gas Oven, Microwave, Refrigerator, Washer
Heating Baseboard, Forced Air, Oil
Cooling Central Air
Has Basement Yes
Basement Finished, Full, Storage Space, Walk-Out Access
Fireplace Yes
# of Fireplaces 1
Fireplaces Pellet Stove

Exterior

Exterior Features Playground
Lot Description Back Yard, Front Yard, Level, Near Golf Course, Near Public Transit, Near School, Near Shops, Private, Views, Wooded
Windows Blinds, Double Pane Windows, Insulated Windows, Oversized Windows, Skylight(s), Wall of Windows
Exterior Frame

School Information

District Pawling
Elementary Pawling Elementary School
Middle Pawling Middle School
High Pawling High School

Additional Information

Date Listed May 5th, 2026
Days on Market 118
Short Sale No
RE / Bank Owned No
Levels Three Or More

Listing Details

OfficeKeller Williams NY Realty

Listing Map

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