Date
Details
Price
Change
Source
7/31/2026
Listed
$699,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$699,000
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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.
Full Property Details
Full Property Details for 21 Overlook Dr
General
- Price: $699,000
- Taxes: $10,222
- Status: Active
- Type: Single Family
- Source: Long_Island
- MLS ID: 1029600
- Updated: 7/31/2026
- Added to Site: 26 day(s) ago
Interior
- Number of Rooms: 8
- Interior Features: First Floor Bedroom, First Floor Full Bath, Beamed Ceilings
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Living Room, Wood Burning
- Appliances: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Indirect Water Heater
- Laundry Facilities: Yes
- Flooring: Carpet, Hardwood, Tile
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: In Hall, Inside
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Diving Board, Fenced, In-Ground, Outdoor Pool
Exterior
- Exterior Features: Garden, Mailbox, Rain Gutters
- Porch/Patio/Deck: Covered, Patio
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 4
- Parking Features: Driveway, Garage, Heated Garage, Oversized
Location
- County: Dutchess County
School Information
- High School District: Pawling
- Elementary School: Pawling Elementary School
- Middle School: Pawling Middle School
- High School: Pawling High School
Heating & Cooling
- Central air: Yes
- Cooling Type: Central Air
- Heating Type: Oil
Utilities
- Sewer: Septic Tank
- Water: Well
- Utility Description: Cable Connected, Electricity Connected, Phone Connected, Propane, Trash Collection Private
Structural Information
- Architectural Style: Ranch
- Detached/Attached: Detached
- Construction: Aluminum Siding, Block, Frame
- Basement: Yes
- Basement Desc.: See Remarks, Storage Space, Walk-Out Access
- Windows: Casement, Oversized Windows, Skylight(s)
- Building Size: 2908
- Square Feet: 2,908
- Sq. Ft. Source: Public Records
- Year Built: 1968
Additional Structures
- Other Structures: Shed(s)
Lot Features
- Property View: Mountain(s), Neighborhood, Panoramic, Skyline
- Mountain views: Yes
- Lot Size (Acres): 4.52
- Lot Size (Sq. Ft.): 196,020
- Frontage: Municipal
- Road Maintenance: Public Maintained Road
- 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
Financial Considerations
- Tax Amount: $10,222.34
Disclosures and Reports
- Special Conditions: None
- Property ID: 134089-6956-00-470746-0000
Listed by McGrath Realty Inc
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Listing agents
— 21 Overlook Dr —
McGrath Realty Inc
McGrath Realty Inc
845-855-5550
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 21 Overlook Dr
School District:Pawling Central School District
| Name | Grades | Distance |
|---|---|---|
Pawling Elementary School 7 Haight Street, Pawling, NY 12564 | K-4 | 1.5 mi |
Pawling Middle School 80 Wagner Drive, Pawling, NY 12564 | 5-8 | 2.6 mi |
Pawling High School 30 Wagner Drive, Pawling, NY 12564 | 9-12 | 2.5 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 21 Overlook Dr
Tax History
Tax History for 21 Overlook Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,155
1%
$137,600
—
2024
$10,076
322%
$137,600
—
2021
$2,385
-75%
$137,600
—
2020
$9,494
14%
$137,600
—
2018
$8,328
-11%
$137,600
—
2017
$9,377
-1%
$137,600
—
2016
$9,509
-2%
$137,600
—
2015
$9,729
-1%
$137,600
—
2015
$9,800
1%
$137,600
—
2013
$9,742
—
$137,600
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 21 Overlook Dr
21 Overlook Drive, Pawling, NY 12564 (MLS# 1029600) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 21 Overlook Drive is currently listed for $699,000 and was received on July 31, 2026. Want to learn more about 21 Overlook Drive? Do you have questions about finding other Single Family real estate for sale in Pawling? You can browse all Pawling real estate or contact a Coldwell Banker agent to request more information.