by RH Advisors

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Dutchess 12564
21 Overlook Drive
$699,000
● House - In Contract

21 Overlook Drive

Pawling, NY 12564
bedrooms
3 Beds
bathrooms
2 Baths, 1 Half Bath
square feet
1,460 Ft²
$4,285
Est. Monthly

About This Property

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.
Unit Size
1,460 Ft²
Days on Market
-
Land Size
4.52 acres
Price per sqft
$479
Property Type
House
Property Taxes
$852
HOA Dues
-
Year Built
1968

Listed By

BRIAN McGRATH
BHHS Hudson Valley Properties

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Last updated: 2 months ago (OneKey MLS #KEY1029600)

Price History

Date / Event Date Event Price
Aug 29, 2026 In contract -
In contract
Jul 28, 2026 Listed by McGrath Realty Inc $699,000
Listed by McGrath Realty Inc

Property Highlights

Garage
Air Conditioning
Fireplace
Parking Details
Has Garage
Has Open Parking
Parking Features: Driveway, Garage, Heated Garage, Oversized
Garage Spaces: 2
Interior Details
Half Bathrooms: 1
Full Bathrooms: 2
Interior Features: Beamed Ceilings, First Floor Bedroom, First Floor Full Bath
Appliances: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Water Heater
Flooring Type: Carpet, Hardwood, Tile
Laundry Features: In Hall, Inside
Rooms: 8
Has Fireplace
Fireplace Features: Living Room, Wood Burning
Fireplaces: 1
Basement: Storage Space, Walk-Out Access, See Remarks
Exterior Details
Square Footage: 1460
Square Footage Source: $0
Architectural Style: Ranch
Year Built: 1968
Building Area Total: 2908
Levels: One
Other Structures: Shed(s)
Building Area Units: Square Feet
Window Features: Skylight(s), Casement, Oversized Windows
Construction Materials: Aluminum Siding, Block, Frame
Patio and Porch Features: Covered, Patio
Pool Features: Diving Board, Fenced, In Ground, Outdoor Pool
Pool is Private
Lot Features: Back Yard, Cleared, Front Yard, Garden, Landscaped, Near Golf Course, Near Public Transit, Wooded, Private, Secluded, Sloped, Split Possible, Sprinklers In Rear, Views, Near School, Near Shops, Stone/Brick Wall
Lot Size Area: 196020
Lot Size Units: Square Feet
Lot Size Acres: 4.52
Lot Size Square Feet: 196020
Water Source: Well
Financial Details
Tax Assessed Value: $137,600
Tax Annual Amount: $10,222
Utilities Details
Cooling Type: Central Air
Heating Type: Oil
Sewer : Septic Tank

Building Info

Overview

    General

  • Year Built: 1968
  • Effective Year Built: 1968
  • Total Rooms: 5
  • Bedroom Count: 3
  • Bathroom Count: 2
  • Full Bathrooms: 2
  • Partial Bathrooms: 2
  • Building Condition: 3
  • Building Quality: 7
  • Construction Type: 0
  • Building Style: 11
  • Exterior Walls Type: 17
  • Interior Walls Type: 0
  • Roof Shape Type: 0
  • Roof Cover Type: 15
  • Floor Count: 100
  • Floor Cover: 0
  • Basement Type: 2
  • Basement Area: 0
  • Garage Type: 1
  • Garage Square Area: 72
  • Parking Space Count: 0
  • Patio Type: 0
  • Porch Type: 0
  • Pool Type: 0

    Dimensions

  • Lot Size Square Feet: 196,020
  • Total Building Area: 1,460
  • Building Area: 1,460
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 0
  • Heating: 10
  • Heated Square Feet: 1,460
  • Heating Fuel Type: 6

    Utilities

  • Sewer System: 4
  • Water Service: 5

Building

  • Building Type: 0
  • Property Class: R
  • Land Acres: 0000004500
  • Standard Land Use Code: 1001
  • County Land Use Code: 210
  • Legal Description 1: 4.5 AC.

Neighborhood

  • School District Name: Pawling Central School District
  • School Tax School District: PAWLING
  • Census Tract: 110003

Zoning

  • Zoning: R-1

Geography

  • Account Number: 11470746
  • District: 134089
  • Section: 6.956
  • Parcel: 134089 6956-00-470746-0000
  • Lot: 470.746
  • Municipality: PAWLING (TOV)
  • Latitude: 41.5554
  • Longitude: -73.6217

    Address

  • Full Address: 21 Overlook Dr
  • Address - House Number: 21
  • Address - Street Name: Overlook
  • Address - Suffix Type: Dr
  • State: NY
  • City Name: Pawling
  • Carrier Code: R002
  • 4-Digit Zip Code: 2011
  • Zip Code: 12564

Valuation

    Tax

  • Tax Year: 2023
  • Tax Amount: $966,325
  • Tax Rate Code Area: 134001

    Appraisal Valuation

  • Standard Deviation: 0.1584
  • Valuation Date: Feb 07, 2024
  • Confidence Score: 80
  • Final Value: 500,707
  • High Value: 580,056
  • Low Value: 421,357

    Market Valuation

  • Market Total Value: $419,800
  • Market Land Value: $107,086
  • Market Improvement Value: $312,714

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $137,600
  • Assessed Land Value: $35,100
  • Assessed Improvements Value: $102,500
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Dutchess


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Frequently Asked Questions

When was property at 21 Overlook Drive built and last sold?
The property at 21 Overlook Drive was built in 1968 and last sold on Jan 1, 1970 for $0.
How much is this home worth?
The estimated value of the home located at 21 Overlook Drive is $691,947.
What are some comparable homes to 21 Overlook Drive?
There are currently no comparable homes to 21 Overlook Drive.