
Land with Home for Sale in Pawling, New York
24 Overlook Dr, Pawling, NY 12564
Tucked away on nearly two private acres, this inviting and versatile home offers the perfect balance of everyday comfort and refined country living-just down the street from the heart of Pawling and less than five minutes to Metro-North via the Harlem Line, allowing for an easy commute to the city. Thoughtfully designed as a 3-bedroom home that lives like a 4-bedroom, the layout adapts naturally to today's lifestyle. The main level features two generously sized bedrooms, along with a flexible third room ideal as a home office, playroom, or additional bedroom, complemented by 1.5 baths. Completing the first floor, the updated kitchen finished with granite countertops flows effortlessly into the living room and opens to a spacious screened-in porch, creating a seamless indoor-outdoor connection optimized for both everyday living and long summer evenings. Upstairs, the primary suite spans the entire floor, providing a private, oasis-like setting with abundant natural light, large walk-in closet and its own en suite bath. On the lower level, the heated, finished walk-out adds exceptional functionality with extra storage options, a bar and lounge area, pellet stove, full bath, and an ideal setup for entertaining, guest quarters, or extended living. The outdoor living space is equally compelling, with Trex decking overlooking 1.95 acres of park-like grounds-providing the peace and tranquility so many are seeking. An attached two-car garage, storage shed, and oversized driveway with a roundabout complete the offering. With a few modern touches, this property can be elevated into something truly special-your own private retreat with the best of both worlds. Conveniently located near shops, dining, schools, and the train, this home presents a rare opportunity to enjoy both accessibility and escape. Don't miss this one!
Location
- Street address
- 24 Overlook Dr
- County
- Dutchess County
- School district
- Pawling
- Elevation
- 725 feet
Directions
Route 22 N to Route 55 W. Overlook Road on right - look for #24
Property details
- Acreage
- 1.95 acres
- MLS #
- MLSLI 995102
- Posted
Property taxes
- 2026
- $14,389
Parcels
- 134089-6956-00-471704-0000
Details and features
Listing
- Type
- Residential
- Subtype
- Single Family Residence
- Franchise
- Keller Williams Realty
Lot
- Features
- Back Yard, Front Yard, Level, Near Golf Course, Near Public Transit, Near School, Near Shops, Private, Views, Wooded
Exterior
- Parking Spaces
- 20
- Parking
- Driveway, Garage, Oversize
- Pool
- Deck, Patio, Porch
- Structures
- Storage
- Features
- Playground
Structure
- Style
- Contemporary
- Stories
- 3
- Basement
- Finished, Full, Storage Space, Walk-Out Access
- Water
- Well
- Sewer
- Septic Tank
- Heating
- Baseboard, Forced Air, Oil
- Cooling
- Central Air
- Materials
- Frame
- Windows
- Blinds, Double Pane Windows, Insulated Windows, Skylight(s)
Interior
- Room Count
- 8
- Rooms
- Basement, Bathroom x 4, Bedroom x 3
- Flooring
- Hardwood, Laminate, Tile
- Fireplaces
- Yes
- Appliances
- Cooktop, Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Cooktop, Gas Oven, Microwave, Refrigerator, Washer
- Features
- Breakfast Bar, Ceiling Fan(s), Chefs Kitchen, Double Vanity, Eat-In Kitchen, Entrance Foyer, First Floor Bedroom, First Floor Full Bath, Granite Counters, Open Floorplan, Primary Bathroom, Walk-In Closet(s)
Nearby schools
| Name | Type | District |
|---|---|---|
| Pawling Elementary School | Elementary | Pawling |
| Pawling Middle School | Middle | Pawling |
| Pawling High School | High | Pawling |
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| May 22, 2026 | Under contract | $689,000 | — | MLSLI |
| May 13, 2026 | Listing removed | $689,000 | — | Listing agent |
| May 7, 2026 | New listing | $689,000 | — | MLSLI |

















































