Login

21 Overlook Drive, Pawling, NY 12564

Pawling
Local realty services provided by:CENTURY 21 Elite Realty
21 Overlook Drive,Pawling, NY 12564
$699,000
Virtual Tour
  • 3 Beds
  • 3 Baths
  • - sq. ft.
  • Single family
  • Coming Soon
Upcoming open houses
  • Sun, Aug 02
    10:00 am - 12:00 pm
Listed by: colleen mcgrath, brian mcgrath
Office: mcgrath realty inc
MLS#:1029600
Source:OneKey MLS

Price summary

  • Price:$699,000

About this home

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...

Contact an agent

contact an agent

Yes, I would like more information. Please use and/or share my information with an independent agent affiliated with the CENTURY 21®  brand to contact me about my real estate needs. By clicking Send message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an independent agent affiliated with the CENTURY 21®  brand is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE® , Coldwell Banker® , Corcoran® , ERA® , Sotheby's International Realty® ). I acknowledge that I have read and agree to theTerms of useandPrivacy notice

Home facts

  • Year built:1968
  • Listing ID #:1029600
  • Updated:July 29, 2026 at 07:49 PM

Rooms and interior

  • Bedrooms:3
  • Total bathrooms:3
  • Full bathrooms:2
  • Half bathrooms:1
  • Rooms Total:8
  • Flooring:Hardwood
  • Kitchen Description:Dishwasher, Microwave, Refrigerator, Stainless Steel Appliance(s)
  • Bedroom Description:First Floor Bedroom
  • Basement:Yes
  • Basement Description:Walk-Out Access

Heating and cooling

  • Cooling:Central Air
  • Heating:Oil
  • Central air:Yes

Structure and exterior

  • Year built:1968
  • Lot Features:Cleared, Garden, Near Public Transit, Part Wooded, Private, Secluded, Sloped, Stone/Brick Wall, Views
  • Architectural Style:Ranch
  • Construction Materials:Aluminum Siding, Block, Frame
  • Levels:1 Story

Schools

  • High school:Pawling High School
  • Middle school:Pawling Middle School
  • Elementary school:Pawling Elementary School

Utilities

  • Water:Well
  • Sewer:Septic Tank

Finances and disclosures

  • Price:$699,000
  • Tax amount:$10,222 (2025)

Features and amenities

  • Appliances:Dishwasher, Dryer, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
  • Laundry features:Dryer, Washer
  • Pool features:In Ground, Outdoor Pool

Parking

  • Total parking spaces:4
  • Parking description:Driveway, Garage, Heated Garage
  • Garage:Yes
  • Garage spaces:2
Copyright 2026 OneKey MLS. All rights reserved. Listings courtesy of OneKey MLS as distributed by MLS GRID <lastMLSCheckTimestamp>. OneKey MLS provides content displayed here (“provided content”) on an “as is” basis and makes no representations or warranties regarding the provided content, including, but not limited to those of non-infringement, timeliness, accuracy, or completeness. Individuals and companies using information presented are responsible for verification and validation of information they utilize and present to their customers and clients. OneKey MLS will not be liable for any damage or loss resulting from use of the provided content or the products available through Portals, IDX, VOW, and/or Syndication. Recipients of this information shall not resell, redistribute, reproduce, modify, or otherwise copy any portion thereof without the expressed written consent of OneKey MLS.

New listings near 21 Overlook Drive