24 Overlook Drive Pawling, NY $ 689,000
24 Overlook Drive
$ 689,000
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24 Overlook Drive

Pawling, NY, 12564
$ 689,000
Bedrooms3 Baths3.1 Sq 3,175

Monthly Estimate*

$ 4,242

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Single Family Home for sale in Pawling, NY

for $689,000 with 3 bedrooms and 3 full baths, 1 half bath. This 3,175 square foot home was built in 1964 on a lot size of 1.95.

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!

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Single Family Pending

Price

$ 689,000

Bedrooms

3

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 14,389

Style

Contemporary

Lot Size

1.95

Year Built

1964

Town/City

Pawling

County/Region

Dutchess

MLS | Web ID

995102

Features
Interior
Interior Amenities 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 Close
Basement Finished Full Storage Space Walk-Out Access
Flooring Hardwood Laminate Tile
Total Fireplaces 1
Fireplace Features Pellet Stove
Basement Features Finished Full Storage Space Walk-Out Access
Basement (Y/N) Y
Window Features Blinds Double Pane Windows Insulated Windows Oversized Windows Skylight(s) Wall of Windows
Fireplace Y/N Y
Half Baths 1
Total Bedrooms 3
Total Baths 4
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General
Sewer Septic Tank
Heating Baseboard Forced Air Oil
Cooling Central Air
Utilities Electricity Connected Trash Collection Private
Appliances Cooktop Dishwasher Dryer Exhaust Fan Freezer Gas Cooktop Gas Oven Microwave Refrigerator Washer
Garage Spaces 2
Patio/Porch Features Covered Deck Patio Porch Screened
Architectural Style Contemporary
Construction Materials Frame
Year Built 1964
Property Subtype Single Family Residence
Tax Year 2026
Parcel Number 134089-6956-00-471704-0000
County Dutchess County
Property Type Residential
HOA N
Garage Y/N Y
Other Structures Shed(s)
Total Rooms 8
Full Baths 3
Directions Route 22 N to Route 55 W. Overlook Road on right - look for #24
High School Pawling High School
City Pawling
Disclosures Lead Paint Seller Property Disclosure
Senior Community Y/N N
High School District Pawling
Carport Y/N N
Elementary School Pawling Elementary School
Property Attached Y/N N
Tax Annual Amount 14389
Middle/Junior High School Pawling Middle School
Property Condition Updated/Remodeled
Additional Parcels Y/N N
Virtual Tour https://reeltorzmedia.com/24-Overlook-Drive/idx https://reeltorzmedia.com/24-Overlook-Drive
Building Area Units Square Feet
Standard Status Pending
Middle/Junior School District Pawling
Elementary School District Pawling
Tax Assessed Value 193700
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Exterior
Exterior Amenities Playground
Parking Features Attached Driveway Garage Oversized Private Attached Driveway Garage Oversized Private
Water Source Well
Total Parking 20
Parking Spaces 20
Waterfront Y/N N
Door Features Storm Door(s)
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Internal Only
Street Number 1 24
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* Excluded Features
List By
Eric Staub

Listing Agent

Keller Williams Ny Realty

Broker

914-437-6100

Contact

Affordability Calculator

$5,441
Per Month
78%
22%
0%
Monthly Principal & Interest
$4,242
Monthly Property Taxes
$1,199
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4100768 Elementary School
4099485 Middle School
Pawling High School High School
Pricing History
DatePricePrice ChangeDescription
5/7/2026$689,000 Listed Price

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24 Overlook Drive, Pawling, NY, 12564 is a Single Family Home for sale at $689,000 with 3,175 sqft and a lot size of 1.95. 24 Overlook Drive has 3 bedrooms, 3.1 baths, and was built in 1964. The property's zip code is 12564 which is in Pawling, NY