For Sale
Open House
Single family home for sale at 18 Chestnut Ln, Pawling, NY 12564 | MLS# 1063978 | Listing updated on 2026-11-03
Photo 1 of Single family home for sale at 18 Chestnut Ln, Pawling, NY 12564 | MLS# 1063978 | Listing updated on 2026-11-03
Photo 2 of Single family home for sale at 18 Chestnut Ln, Pawling, NY 12564 | MLS# 1063978 | Listing updated on 2026-11-03
Photo 3 of Single family home for sale at 18 Chestnut Ln, Pawling, NY 12564 | MLS# 1063978 | Listing updated on 2026-11-03
Photo 4 of Single family home for sale at 18 Chestnut Ln, Pawling, NY 12564 | MLS# 1063978 | Listing updated on 2026-11-03
33+
Beds Icon

Street View

$739,900

Monthly Est:$3,683

  • Beds Icon4 Beds
  • Beds Icon
    3 Baths
  • Beds Icon3,277sqft

18 Chestnut Ln, Pawling, NY 12564

$3,683/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 2005

  • $423/mo HOA

  • 25,700 sqft lot

  • $226/sq.ft

Description

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 private in-ground 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 bas
ement 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. Water & Sewer included in HOA.

  • Houzeo last checked: 7 minutes ago
  • Listing updated: November 3, 2026 at 1:06 am
  • Listing Provided by: Joseph Matta (845) 803-3674 | X-Cap Realty LLC (929) 998-9227
  • Source: OneKey MLS-NY as distributed by MLS GRID | MLS#: 1063978 OneKey MLS-NY as distributed by MLS GRID

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Dutchess County

  • City

    Pawling

  • Neighborhood

    --

  • Year Built

    2005

  • HOA Fees

    $423/mo

  • Finished Area

    3,277 sqft

  • Lot Size

    25,700 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    OneKey MLS

  • MLS Number

    1063978

  • MLS Status

    Active

  • Days on Market

    15

  • Cumulative Days on Market

    11

Open House

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Location

HOA Management

J&J Management

HOA Fees

$423/ Monthly

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Tennis Tennis

Pool Pool

Snow Removal Snow Removal

Sewer Sewer

Water Water

Common Area Maintenance Common Area Maintenance

Other Other

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 3

Interior

  • Flooring

    Hardwood

  • Appliances

    Cooktop, Dishwasher, Dryer, Refrigerator, Stainless Steel Appliance(s), Washer

  • Interior Features

    Ceiling Fan(s), Chefs Kitchen, Eat In Kitchen, Entrance Foyer, Formal Dining, Kitchen Island

  • Sewer

    Public Sewer

  • Cooling

    Central Air

  • Heating

    Forced Air

Construction

  • Year Built

    Year Built: 2005

  • Home type

    Single Family Residence

  • Architectural Style

    Colonial

  • Construction Materials

    Frame, Vinyl Siding

Utilities & Energy

  • Water Source

    Shared Well

  • Laundry Features

    Inside

  • Parking Features

    Attached, Garage

  • Basement

    Full, Partially Finished

  • Association Amenities

    Pool, Snow Removal, Tennis Court(s)

  • Utilities

    Trash Collection Private

Other Features

  • Subdivision Name

    Highlands

Price History

DateEventPrice

10/22/2026

Source: mls_logoOneKey MLS-NY as distributed by MLS GRID #KEY1063978

Listed for Sale

$739,900

$226/sqft

10/19/2026

Source: mls_logoOneKey MLS-NY #KEY1063978

Coming Soon

$739,900 +13.83%

$226/sqft

07/09/2022

Source: mls_logoOneKey MLS-NY as distributed by MLS GRID #KEYH6171845

Sold

$650,000

$198/sqft

Nearby Homes

Based on information from OneKey MLS® through Nov 04, 2026, 05:31AM as submitted to and distributed by MLS GRID. 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. IDX information is provided exclusively for consumers’ personal non-commercial use. It 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. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 OneKey MLS. All rights reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

Skip to Main Content