3 beds1,460 sqft$479/sqft
21 Overlook Rd, Pawling, NY 12564
Est: $4,405/moGet pre-approved

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...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.
LISTING UPDATED: 08/04/2026 07:12 PM

  1. Listed by Colleen McGrath • McGrath Realty Inc
    P: (845)-855-5550 C: (845)-803-4341 cmcgrath@mcgrathny.com
  2. Listed by Brian McGrath • McGrath Realty Inc
    P: (845)-855-5550 C: (845)-721-0940 bmcgrath@mcgrathrealtyinc.com

Property Details for 21 Overlook Road

Status
MLS #
1029600
Days on Market
7
Taxes
$10,222 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
MLS Type
Single Family
Year Built
1968
Lot Size
4.50 AC / 196,020 SF
City/Township
Pawling
View
Mountain(s), Neighborhood, Panoramic, Skyline
Architectural Style
Ranch
Garage Spaces
2
Waterfront
No

Location

Listing Courtesy of McGrath Realty Inc
Add your commute

Building Information for 21 Overlook Road

Stories-Year Built1968Building Size-Lot Size4.50 AC / 196,020 SF

Payment Calculator

$4,405 per month

30 year fixed, 6.55% Interest

Principal and Interest

$3,553

Property Taxes

$852

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 21 Overlook Road

Summary
Location and General Information
  • Senior Community YN: No
  • Year Built Effective: 1968
  • Property Attached: No
  • Structure Type: Detached
  • Levels: One
  • Country: US
  • State Or Province: NY
School Information
  • School District: Pawling
  • Elementary School District: Pawling
  • Elementary School: Pawling Elementary School
  • Middle Or Junior School District: Pawling
  • Middle Or Junior School: Pawling Middle School
  • High School District: Pawling
  • High School: Pawling High School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Room Information
Room 1 Information
  • Room Level: First
  • Room Type: Kitchen
Room 2 Information
  • Room Level: First
  • Room Type: Family Room
Room 3 Information
  • Room Level: First
  • Room Type: Bedroom 1
Room 4 Information
  • Room Level: First
  • Room Type: Bedroom 2
Room 5 Information
  • Room Level: First
  • Room Type: Bedroom 3
Room 6 Information
  • Room Level: Basement
  • Room Type: Bonus Room
Room 7 Information
  • Room Level: First
  • Room Type: Bathroom 1
Room 8 Information
  • Room Level: First
  • Room Type: Bathroom 2
Room 9 Information
  • Room Level: Basement
  • Room Type: Bathroom 3
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 134089-6956-00-470746-0000
  • Tax Assessed Value: $137,600.00
  • Additional Fees: No
  • Tax Source: Municipality
  • Tax Year: 2025
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Beamed Ceilings, Carpet, Casement, Covered, Diving Board, Fenced, First Floor Full Bath, Garden, Hardwood Floors As Seen, In Ground, In Hall, Inside, Living Room, Mailbox, Mountain(s), Neighborhood, Outdoor Pool, Oversized Windows, Panoramic, Patio, Rain Gutters, Ranch, Shed(s), Sky Light, Skyline, Tile, Well, Wood Burning
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Beamed Ceilings
  • Appliances: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Indirect Water Heater
  • Total Rooms: 8
  • Basement: See Remarks, Storage Space, Walk-Out Access
  • Attic Description: None
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Fireplace Features: Living Room, Wood Burning
  • Location Amenities: Stainless Steel Appliances, Walk Out Basement, Hardwood Floors As Seen, 1st Fl Master Bedroom, Garden, Privacy, Brownstone, Scenic View, Heated Parking, Patio, In Ground Pool, Pool Outdoor, Mountain Views, Open View, Skyline View, Casement Windows, Oversized Windows, Sky Light
  • Laundry Features: In Hall, Inside
  • Spa: No
  • Window Features: Casement, Oversized Windows, Skylight(s)
  • Flooring: Carpet, Hardwood, Tile
  • Living Area: 1460
  • Foundation Details: Block
  • Basement: Yes
Exterior Features
  • Exterior Features: Garden, Mailbox, Rain Gutters
  • Exterior Property Features: Garden, Mailbox, Rain Gutters, Diving Board, Fenced, In Ground, Outdoor Pool, Covered, Patio, Driveway, Garage, Heated Garage, Oversized, Casement, Oversized Windows, Skylight(s), Back Yard, Cleared, Front Yard, 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
  • Elevation Certificate: No
  • Patio And Porch Features: Covered, Patio
  • Construction Materials: Aluminum Siding, Block, Frame
  • Road Frontage Type: Municipal
  • Road Responsibility: Public Maintained Road
  • Other Structures: Shed(s)
  • Horse: No
  • Pool Private: Yes
  • Pool Features: Diving Board, Fenced, In Ground, Outdoor Pool
  • Pool Details: Diving Board,Fenced,In Ground,Outdoor Pool
Lot Information
  • 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
  • Additional Parcel: No
  • Site 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
  • Building Area Units: Square Feet
Parking
  • Parking Features: Driveway, Garage, Heated Garage, Oversized
  • Parking Total: 4.00
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Oil
  • Heat Fuel Type: Oil
  • Sewer: Septic Tank
  • Water Source: Well
  • Utilities: Cable Connected, Electricity Connected, Phone Connected, Propane, Trash Collection Private
Green Features
  • Green Features: Casement, Oversized Windows, Skylight(s), Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Indirect Water Heater, Oil, Garden, Mailbox, Rain Gutters, Diving Board, Fenced, In Ground, Outdoor Pool
Agent
Payment and Rate
  • Down Payment Resource: Yes

Property History for 21 Overlook Road

DateEvent & SourcePriceAppreciation
Jul 31, 2026

Listed (Active)

ONEKEY #1029600

$699,000
DateEvent & SourcePrice
07/31/2026

Listed (Active)

ONEKEY #1029600

$699,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 21 Overlook Road

Taxable ValueLand$35,100Additions$102,500Total$137,600
Tax Record2025$10,155 ($846 / month)
Home Facts
Beds3Baths2Total Finished SqFt1,460 SqFtAbove Grade Finished SqFt1,460 SqFtStories1Lot Size196,020 SqFtStyleSingle Family ResidenceYear Built1968Year Renovated1968ZoningR-1CountyDUTCHESSAPN134089-6956-00-470746-0000

Schools near 21 Overlook Road

This home is within Pawling Central School District.
Rating
School
Type
Grades
Distance
Public - PK to 4
Public - 5 to 8
Public - 9 to 12
Private - PK to 8
Rating
School
Distance
Pawling Elementary School
PublicPK to 4

Pawling Middle School
Public5 to 8

Pawling High School
Public9 to 12

Mizzentop Day School
PrivatePK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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21 Overlook Road is a single family home for sale in Pawling, NY 12564. This property was listed for sale on July 31, 2026 by McGrath Realty Inc, it's currently listed at $699,000. This listing's school district is Pawling Central School District. Nearby schools include Pawling Elementary School, Pawling Middle School and Pawling High School. 21 Overlook Road is a 3-bed, 3-bath, 1,460 sqft single family home built in 1968.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of McGrath Realty Inc

Based on information submitted to the MLS GRID as of 08/04/2026 07:12 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.