21 Overlook Drive, Pawling, NY 12564

• 3 beds |
• 3 baths |
• 1,460 sqft

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.

Listing Status:

Active

Data Last Updated:

August 10, 2026 at 11:22PM

Listing Office:

McGrath Realty Inc : 845-855-5550

MLS ID:

1029600

Interior

• General: First Floor BedroomFirst Floor Full BathBeamed Ceilings
• Appliances: DishwasherDryerElectric RangeMicrowaveRefrigeratorStainless Steel Appliance(s)WasherIndirect Water Heater
• Laundry: In HallInside
• Basement: See RemarksStorage SpaceWalk-Out Access
• Flooring: CarpetHardwoodTile
• A/C: Central Air
• Heating: Oil
• Fireplace: Living RoomWood BurningFireplaceFireplaces: 1

Exterior

• General: GardenMailboxRain Gutters
• Style: Ranch
• Other Structures: Shed(s)PatioCovered
• Pool: Diving BoardFencedIn GroundOutdoor Pool
• Parking: DrivewayGarageHeated GarageOversizedParking spaces: 4

Construction

• Windows: CasementOversized WindowsSkylight(s)
• General: One

Location

• Road/Access: Municipal
• Originating MLS: onekey2
• School District: Pawling
• County: Dutchess County

Lot

• Zoning: 134089-6956-00-470746-0000
• View: Mountain(s)NeighborhoodPanoramicSkyline

Utilities

• Utilities: Cable ConnectedElectricity ConnectedPhone ConnectedPropaneTrash Collection Private
• Water: Well
• Sewer: Septic Tank

Financial

• Source: onekey2