18 Chestnut Lane Pawling, NY $ 739,900
18 Chestnut Lane
$ 739,900
Open House 10/24 11:30am - 1:30pm
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18 Chestnut Lane

Pawling, NY, 12564
$ 739,900
Bedrooms4 Baths3.0 Sq 3,277

Monthly Estimate*

$ 5,110

18 Chestnut Lane, Pawling, NY 12564 - Image 1

Single Family Home for sale in Pawling, NY

for $739,900 with 4 bedrooms and 3 full baths. This 3,277 square foot home was built in 2005 on a lot size of 0.59.

Welcome to 18 Chestnut Lane in the Highlands of Pawling! This four-bedroom, three-bath Colonial combines spacious interiors with a private in-ground pool and sought-after community amenities. Hardwood floors flow throughout the main level, featuring a formal dining room and an open kitchen with granite countertops, stainless steel appliances, a center island, and coffee bar. The deck overlooks the backyard and pool, creating an inviting setting for outdoor dining and entertaining. Upstairs, the primary suite offers a tray ceiling, walk-in closet, and private bath with dual sinks, alongside three additional bedrooms and a bonus room. The full walkout basement features high ceilings, full-size windows, and possibilities for a home gym or recreation space. An attached two-car garage adds everyday convenience. Enjoy access to the Highlands’ community pool, tennis courts, and pond for kayaking and fishing. Conveniently located near the Village of Pawling’s shops, restaurants, and Metro-North station, this home offers space, recreation, and connection to all Pawling has to offer.

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Open House

10/24/2026 11:30 AM - 1:30 PM
18 Chestnut Lane Pawling, NY
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Coming Soon

Price

$ 739,900

Bedrooms

4

Full Bath

3

Property Type

Single Family

Taxes

$ 16,943

Style

Colonial

Lot Size

0.59

Year Built

2005

Town/City

Pawling

County/Region

Dutchess

MLS | Web ID

1063978

Features
Interior
Interior Amenities Ceiling Fan(s) Chefs Kitchen Eat-in Kitchen Entrance Foyer Formal Dining Kitchen Island
Basement Full Partially Finished
Flooring Hardwood
Basement Features Full Partially Finished
Basement (Y/N) Y
Fireplace Y/N Y
Half Baths 0
Total Bedrooms 4
Total Baths 3
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General
Sewer Public Sewer
Heating Forced Air
Cooling Central Air
Utilities Trash Collection Private
Appliances Cooktop Dishwasher Dryer Refrigerator Stainless Steel Appliance(s) Washer
HOA Fee 423
Garage Spaces 2
Association Fee Includes Common Area Maintenance Other Sewer Snow Removal Water
Architectural Style Colonial
Construction Materials Frame Vinyl Siding
Year Built 2005
Property Subtype Single Family Residence
Tax Year 2026
Parcel Number 134089-6956-01-057906-0000
Assoc Fee Paid Per Monthly
County Dutchess County
Property Type Residential
HOA Y
Subdivision Name Highlands
Garage Y/N Y
Total Rooms 9
Full Baths 3
High School Pawling High School
City Pawling
Association Name J&J Management
Senior Community Y/N N
High School District Pawling
Carport Y/N N
Elementary School Pawling Elementary School
Property Attached Y/N N
Tax Annual Amount 16943
Middle/Junior High School Pawling Middle School
Building Area Units Square Feet
Standard Status Coming Soon
Middle/Junior School District Pawling
Elementary School District Pawling
Tax Assessed Value 225000
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Exterior
Parking Features Attached Garage Attached Garage
Water Source Shared Well
Waterfront Y/N N
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Internal Only
Street Number 1 18
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* Excluded Features
List By
Joseph Matta

Listing Agent

X-Cap Realty Llc

Broker

Joematta.re@gmail.com

Email

Affordability Calculator

$6,522
Per Month
78%
22%
0%
Monthly Principal & Interest
$5,110
Monthly Property Taxes
$1,412
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4100768 Elementary School
4099485 Middle School
Pawling High School High School
Pricing History
DatePricePrice ChangeDescription
10/20/2026$739,900 Listed Price

Map


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18 Chestnut Lane, Pawling, NY, 12564 is a Single Family Home for sale at $739,900 with 3,277 sqft and a lot size of 0.59. 18 Chestnut Lane has 4 bedrooms, 3.0 baths, and was built in 2005. The property's zip code is 12564 which is in Pawling, NY