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Sale Pending at 21 Overlook Dr, Pawling, NY 12564 | MLS# 1029600 | Listing updated on 2026-08-29
Photo 1 of Sale Pending at 21 Overlook Dr, Pawling, NY 12564 | MLS# 1029600 | Listing updated on 2026-08-29
Photo 2 of Sale Pending at 21 Overlook Dr, Pawling, NY 12564 | MLS# 1029600 | Listing updated on 2026-08-29
Photo 3 of Sale Pending at 21 Overlook Dr, Pawling, NY 12564 | MLS# 1029600 | Listing updated on 2026-08-29
Photo 4 of Sale Pending at 21 Overlook Dr, Pawling, NY 12564 | MLS# 1029600 | Listing updated on 2026-08-29
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$699,000

Monthly Est:$3,479

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon1,460sqft

21 Overlook Dr, Pawling, NY 12564

$3,479/moEst:

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  • Single Family Residence

  • Built in 1968

  • $-- HOA

  • 4.5 acres lot

  • $479/sq.ft

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.

  • Houzeo last checked: 11 hours ago
  • Listing updated: August 29, 2026 at 7:11 am
  • Listing Provided by: Colleen McGrath (845) 803-4341 , Brian McGrath | McGrath Realty Inc (845) 855-5550
  • Source: OneKey MLS-NY | MLS#: 1029600 OneKey MLS-NY

Property Details

  • Status

    Pending

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Dutchess County

  • City

    Pawling

  • Neighborhood

    --

  • Year Built

    1968

  • HOA Fees

    -

  • Finished Area

    1,460 sqft

  • Lot Size

    4.5 acres lot

  • Basement Area

    - sqft

  • MLS Name

    OneKey MLS

  • MLS Number

    1029600

  • MLS Status

    Pending

  • Days on Market

    72

  • Cumulative Days on Market

    28

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 3

  • Kitchen

    Level: First

  • Family Room

    Level: First

  • Bedroom 1

    Level: First

  • Bedroom 2

    Level: First

  • Bedroom 3

    Level: First

  • Bonus Room

    Level: Basement

  • Bathroom 1

    Level: First

  • Bathroom 2

    Level: First

  • Bathroom 3

    Level: Basement

Interior

  • Appliances

    Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Indirect Water Heater

  • Exterior Features

    Garden, Mailbox, Rain Gutters

  • Interior Features

    First Floor Bedroom, First Floor Full Bath, Beamed Ceilings

  • Sewer

    Septic Tank

  • Window Features

    Casement, Oversized Windows, Skylight(s)

  • Cooling

    Central Air

  • Flooring

    Carpet, Hardwood, Tile

  • Heating

    Oil

Construction

  • Year Built

    Year Built: 1968

  • Home type

    Single Family Residence

  • Foundation Details

    Block

  • Architectural Style

    Ranch

  • Construction Materials

    Aluminum Siding, Block, Frame

Utilities & Energy

  • Basement

    See Remarks, Storage Space, Walk Out Access

  • Fireplace Features

    Living Room, Wood Burning

  • Utilities

    Cable Connected, Electricity Connected, Phone Connected, Propane, Trash Collection Private

  • Pool Features

    Diving Board, Fenced, In Ground, Outdoor Pool

  • Laundry Features

    In Hall, Inside

  • Parking Features

    Driveway, Garage, Heated Garage, Oversized

  • Water Source

    Well

Other Features

  • Patio And Porch Features

    Covered, Patio

  • 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

  • Disclosures

    Lead Paint, Seller Property Disclosure

Price History

DateEventPrice

08/28/2026

Source: mls_logoOneKey MLS-NY #KEY1029600

Pending

$699,000

$479/sqft

07/31/2026

Source: mls_logoOneKey MLS-NY #KEY1029600

Listed for Sale

$699,000

$479/sqft

07/28/2026

Source: mls_logoOneKey MLS-NY #KEY1029600

Coming Soon

$699,000

$479/sqft

Getting Around 21 Overlook Dr

Walk Score®

Walk Score

Car-Dependent

0/100

Data provided by Redfin

Nearby Homes

Based on information from OneKey MLS, through Oct 09, 2026, 02:32PM. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 OneKey® MLS. All rights reserved.

Advertising Broker: Derek Greene | The Greene Realty Group