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Land with Home for Sale in Pawling, New York

21 Overlook Dr, Pawling, NY 12564

$699,000
4.52 acres
Active sale
ago
Est $4,423/mo

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.

1,460
Sq feet
3
Beds
2
Full baths
1
1/2 bath
1968
Built

Location

Street address
21 Overlook Dr
Zip code
12564
School district
Pawling
Elevation
799 feet
Coordinates
41.5555, -73.6216

Property details

Acreage
4.52 acres
MLS #
MLSLI 1029600
Posted

Property taxes

2025
$10,222

Parcels

  • 134089-6956-00-470746-0000

Open houses

DateBeginsEndsAppt neededRemarks
Aug 2, 202610:00 AM12:00 PMNo

Details and features

Listing

Type
Residential
Subtype
Single Family Residence
Franchise
Independent

Lot

Features
Back Yard, Cleared, Front Yard, Garden, Landscaped, Near Golf Course, Near Public Transit, Near School, Near Shops, Part Wooded, Private, Secluded, Sloped, Split Possible, Sprinklers in Rear, Stone/Brick Wall, Views

Exterior

Parking Spaces
4
Parking
Driveway, Garage, Oversize
Pool
Patio
Features
Mailbox, Rain Gutters

Structure

Style
Ranch
Stories
1
Basement
Storage Space, Walk-Out Access
Water
Well
Sewer
Septic Tank
Heating
Oil
Cooling
Central Air
Materials
Aluminum Siding, Block, Frame
Windows
Skylight(s)

Interior

Room Count
8
Rooms
Basement, Bathroom x 3, Bedroom x 3, Bonus Room, Family Room
Flooring
Carpet, Hardwood, Tile
Fireplaces
Yes
Appliances
Dishwasher, Dryer, Electric Range, Indirect Water Heater, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
Features
Beamed Ceilings, First Floor Bedroom, First Floor Full Bath

Property utilities

CategoryTypeStatus
GasPropaneConnected

Nearby schools

NameTypeDistrict
Pawling Elementary SchoolElementaryPawling
Pawling Middle SchoolMiddlePawling
Pawling High SchoolHighPawling

Listing history

DateEventPriceChangeSource
July 31, 2026New listing$699,000MLSLI
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This 4.52-acre property is located at 21 Overlook Dr in Pawling, NY 12564. The property is available for sale, priced at $699,000. It has a 1,460 square foot 3-bedroom, 2.5-bath house built in 1968.

Listed by McGrath Realty, (845) 855-5550

Checked 1 hour agoUpdated Source

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