Virtual Tour

$699,000

For Sale

21 days ago

21 Overlook Dr, Pawling, NY

House

MLS® 1029600

3 Bed

3 Bath

1460 sqft

4 Parking

Key Facts
Description
Rooms
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 1460 sqft

Garage Yes

Taxes $10,222

Days Active 19

Lot Size 4.52 Acres

Approx. Age 1968

Avg. Price Per Sqft $478

MLS® Number 1029600

Property Address: 21 Overlook Dr, Pawling, NY, 12564-2011

Average square foot calculated using Size range provided by listing agent.

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.

MLS® Number1029600

Laundry LevelEnsuite

Central VacNo

FireplaceYes

Acreage

Exterior

GarageYes

Approx. Age1968

BasementSee Remarks, Storage Space, Walk-Out Access

DrivewayDriveway, Garage, Heated Garage, Oversized

Garage Spaces

HeatOil

A/CCentral Air

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

Jul 28, 2026List Date

$699,000List Price

Commute

Commute

Starting Address

Destination Address

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