• Buy
  • Rent
  • Sell
  • Agents
New DevelopmentWorld of Elliman
The latest in luxury property, lifestyle & culture, curated just for you.

Company

  • About Us
  • Leadership
  • Offices
  • Press & News
  • Elliman Cares
  • Join as an Agent
  • Careers
  • Elliman Global
  • Investors

Resources

  • World of Elliman
  • Elliman Insider
  • Magazines
  • Market Reports
  • Research Reports
  • Elliman Private Listings
  • New Elliman Exclusives
  • Featured Cities
  • Guides to Buying & Selling

Brand Portfolio

  • New Development
  • Commercial
  • Relocation
  • Sports & Entertainment
  • Farm & Ranch
  • Building Broker Specialists
  • Title Services
  • Estate, Trust & Probate
  • Elliman Yachts

  • California
  • Colorado
  • Connecticut
  • Florida
  • Massachusetts
  • Mid-Atlantic
  • Nevada
  • New Jersey
  • New York
  • New York City
  • Texas
  • Vermont
  • France
  • Monaco
  • Site Map
  • Terms
  • Privacy
  • Cookie Preferences
  • Do Not Sell or Share My Personal Information
  • NYS Housing Discrimination Disclosure Notice & Form
  • NYS Standard Operating Procedure
  • NYS Tenants' Rights to Reasonable Accommodations for persons with disabilities
  • California Consumer Privacy Act Notice
  • Texas Consumer Protection Notice
  • Texas Real Estate Commission Information About Brokerage Services
  • Text of NYC Human Rights Law
  • New York City Commission on Human Rights
  • NYC Source of Income Discrimination Information
  • NYC Source of Income Discrimination Tenant FAQs

THE SOURCE OF THE DISPLAYED DATA IS EITHER THE PROPERTY OWNER OR PUBLIC RECORD PROVIDED BY NON-GOVERNMENTAL THIRD PARTIES. IT IS BELIEVED TO BE RELIABLE BUT NOT GUARANTEED. FOR COLORADO VIEWERS, INFORMATION ABOUT NON-COMMERCIAL PROPERTIES IS PROVIDED EXCLUSIVELY FOR YOUR PERSONAL, NON-COMMERCIAL USE.

575 MADISON AVENUE, NEW YORK, NY 10022. 212.891.7000 © 2026 DOUGLAS ELLIMAN REAL ESTATE. EQUAL EMPLOYMENT OPPORTUNITY PROVIDER. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES, OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS, AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT, OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY. LISTING DATA REFRESHED ON AUG 5 2026 AT 1:41 PM.

DOUGLAS ELLIMAN IS A LICENSED REAL ESTATE BROKER IN CALIFORNIA WITH LICENSE # 01947727, COLORADO WITH LICENSE # EC100053892, CONNECTICUT WITH LICENSE # REB.0314827, THE DISTRICT OF COLUMBIA WITH LICENSE # REO40000160, FLORIDA WITH LICENSE # CQ1020232, MARYLAND WITH LICENSE # 645270, MASSACHUSETTS WITH LICENSE # 422764, NEVADA WITH LICENSE # 1454643, NEW JERSEY WITH LICENSE # 0572105, NEW YORK WITH LICENSE # 10991211812, TEXAS WITH LICENSE # 9008706, AND VIRGINIA WITH LICENSE # 0226035659.

SCAMMERS ARE IMPERSONATING REAL ESTATE AGENTS AND USING ACTIVE LISTINGS TO REQUEST FAKE DEPOSITS. SHOULD YOU HAVE A QUESTION ABOUT THE LEGITIMACY OF A DOUGLAS ELLIMAN AGENT OR LISTING, PLEASE CONTACT THE AGENT DIRECTLY VIA THE “AGENTS” LINK IN THE TOP MENU. DOUGLAS ELLIMAN WILL NEVER ASK FOR ANY PAYMENT TO RESERVE, HOLD, OR VIEW A PROPERTY. THESE CHARGES ARE PROHIBITED UNDER NEW YORK LAW. IF YOU RECEIVE A SUSPICIOUS REQUEST FOR MONEY, DO NOT SEND FUNDS. REPORT IT TO THE NYS DEPARTMENT OF STATE AND NOTIFY DOUGLAS ELLIMAN. YOU CAN READ THE NEW YORK STATE DEPARTMENT OF STATE'S CONSUMER ALERT HERE.

This website has been translated using automated software for convenience. While reasonable efforts have been made to ensure accuracy, machine translation may contain errors and is not a substitute for human translation. Translations are provided “as is,” without any express or implied warranty regarding their accuracy, reliability, or completeness. Some content (including images or videos) may not be translated accurately. The official version of this website is the English version. Any discrepancies in translation are not binding and have no legal effect; the English version controls.

POWERED BY PURLIN.AI

21 Overlook Dr

pawling, NY 12564

$699,000

  • 3 BR
    2 BA, 1 HALF BA
    approx. 1,460 SF

Interested? Let's Connect

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.

Details

1,460 Sq Ft

4.52 Private Acres Lot Size

single family home

$852 Monthly Tax

Built in 1968

MLS/Listing ID 1029600

Amenities & Features

Construction - Aluminum Siding

Construction - Block

Construction - Frame

Style - Ranch

Dishwasher

Dryer

Electric Range

Microwave

Refrigerator

Washer

Lot - Front Yard

Lot - Garden

Lot - Landscaped

Lot - Near Golf Course

Lot - Near Public Transit

Lot - Private

Lot - Secluded

Lot - Sloped

Lot - Split Possible

Lot - Sprinklers in Rear

Lot - Views

Inside

Pool - Diving Board

Pool - Fenced

Pool - Inground

Pool - Outdoor

Covered

Patio

Parking - Driveway

Parking - Garage

Parking - Heated Garage

Parking - Oversized

Lot - Cleared

Panoramic View

Neighborhood View

Mountains View

Casement Windows

Stainless Steel Appliance(s)

Lot - Back Yard

Lot - Near School

Lot - Stone/Brick Wall

Skyline View

Oversized Windows

Skylights

Septic System

Well

Cooling - Central Air

Rain Gutters

Garden

Wood Burning Fireplace

Living Room Fireplace

Tile

Hardwood

Carpet

Block

Heating - Oil

Beamed Ceilings

Estimate my mortgage

TOTAL MONTHLY COST

$0

  • PRINCIPAL & INTEREST

    $0

  • PROPERTY TAXES

    $0

  • Common Charges

    $0

HOME PRICE
DOWN PAYMENT
TERM
INTEREST

Interested In 21 Overlook Dr?