NY
Dutchess
Pawling
12564
21 Overlook Drive
21 Overlook Drive, Pawling, NY 12564
Share Listing
Listing Type
Single Family
Listing Status
Coming Soon
47
$699,000

Home Details for 21 Overlook Drive

Price
$699,000
Type
Residential
Bedrooms
3
Total Bathrooms
3
Full Bathrooms
2
Half Bathrooms
1
Square feet
1460
Year built
1968
Lot size acres
4.52
County
Dutchess
Total rooms
8
Garage
2
Basement
Storage Space, Walk-Out Access
MLS Listing#
1029600
Property Description

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.

Property Features
  • Utilities
    • Cable Connected
    • Electricity Connected
    • Phone Connected
    • Propane
  • Parking
    • Driveway
    • Garage
    • Heated Garage
    • Oversized
  • Water Features
    • Private
    • Well
  • Basement
    • Storage Space
    • Walk-Out Access
  • Fire Place
    • Living Room
    • Wood Burning
  • Cooling Information
    • Central Air
  • Heating Information
    • Oil
  • House Interior
    • Beamed Ceilings
School Information
School Information for 21 Overlook Drive, Pawling, NY 12564
Elementary School
Pawling Elementary School
Middle School
Pawling Middle School
High School
Pawling High School
Listing Courtesy: McGrath Realty Inc - 845-855-5550
Presented by: Colleen McGrath
The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright ©2026 OneKey MLS. All Rights Reserved
Fair Housing Notice
Transportation
Check the walk, transit, and bike score for
Neighborhood Market Statistics
See average values in the proximity of this property
Median Listing Price
Median Days on Site
Median Square Feet
Market statistics compiled from data from OneKey MLS.
EXIT REALTY CONNECTIONS
2790 W. Main St., Wappingers Falls, NY 12590
Office
845 298 6034
Request more details
Code: