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Ruth Sobey
REALTOR®
(516) 796-8900
Broker/Sales Representative
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21 Overlook Drive, Pawling, NY 12564

$699,000
  • 21 Overlook Drive, Pawling, NY 12564 Main Photo

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New to the Market Active
BEDS3 BATHS2 full 1 partial SQUARE FEET1,460 MLS#1029600
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLPawling

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.

21 Overlook Drive | MLS# 1029600

This single family home located at 21 Overlook Drive, Pawling, NY 12564 is currently listed for sale with an asking price of $699,000. This property was built in 1968 and has 3 bedrooms and 2 full and 1 partial baths with 1460 sq. ft. Overlook Drive is located within the Pawling school district. Search Pawling real estate on ruthsobey.cbamhomes.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: See Remarks, Storage Space, Walk-Out Access
Cooling: Central Air
Fenced: Yes
Fireplaces: 1
Garage: 2
Heating: Oil
Home Style: Ranch
Lot Size: 4.50 Acres
Taxes: $10,222
Year Built: 1968

Amenities

First Floor Bedroom
First Floor Full Bath
Beamed Ceilings
Garden
Mailbox
Rain Gutters

Feature Descriptions

Appliances: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Indirect Water Heater
Building Area Total: 2908
Days on Site: 2
Exterior: Aluminum Siding, Block, Frame
Fireplace Features: Living Room, Wood Burning
Fireplace Y/N: Yes
Flooring: Carpet, Hardwood, Tile
GarageY/N: Yes
Laundry: In Hall, Inside
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
On Market Date: 2026-07-31
Other Structures: Shed(s)
Parcel Number: 134089-6956-00-470746-0000
Parking Features: Driveway, Garage, Heated Garage, Oversized
Parking Total: 4
Patio And Porch: Covered, Patio
Pool Features: Diving Board, Fenced, In Ground, Outdoor Pool
Rental Term: Monthly
Road Responsibility: Public Maintained Road
Rooms Total: 8
Sewer: Septic Tank
Skylight: Y
Special View Info: Mountain(s), Neighborhood, Panoramic, Skyline
Swimming Pool: Yes
Utilities: Cable Connected, Electricity Connected, Phone Connected, Propane, Trash Collection Private
Water: Well
Window Features: Casement, Oversized Windows, Skylight(s)
Wooded: Yes

Local Schools

High School: Pawling High School
Middle School: Pawling Middle School
Elementary School: Pawling Elementary School
School District: Pawling

Estimate Your Payment

Estimated Payment

$ 4,590.23 per month $3,534.52 Principal & Interest $851.83 Property Tax $203.88 Homeowner's Insurance

Change Payment Information

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(Payments are an estimate and may vary by lender)

Listed By / Shown By

Listing By

Agency Name: McGrath Realty Inc
Agency Contact: 845-855-5550

agent picture

Shown By

Agent Name: Ruth Sobey
Agent Phone: (516) 796-8900
Agency Title: Coldwell Banker American Homes

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