About this home

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 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. Water & Sewer included in HOA.

Facts and features

Schools

• Pawling Elementary School

  elementary · K-4 · 2.1 mi

  5

• Pawling Middle School

  elementary · 5-8 · 2.9 mi

  7

• Pawling High School

  high · 9-12 · 3.0 mi

  7

• Duane Lake Academy

  elementary · K-12 · 1.4 mi

• Mission Church Academy And Preschool

  elementary · PK-K · 1.9 mi

• Mizzentop Day School

  elementary · K-8 · 2.0 mi

Price history

• Oct 22, 2026 · Listed$739,900
• Sep 14, 2022 · Sold$650,000
• Apr 23, 2022 · Listing Removed—
• Mar 31, 2022 · Price Changed$650,000
• Mar 14, 2022 · Listed$675,000
• Aug 25, 2006 · Sold$672,278

Tax history

• 2026$15,871 tax · $225,000 assessed
• 2025$15,821 tax · $225,000 assessed
• 2024$15,590 tax · $225,000 assessed
• 2023$16,013 tax · $225,000 assessed
• 2022$15,676 tax · $225,000 assessed
• 2021$15,551 tax · $225,000 assessed
• 2020$13,927 tax · $225,000 assessed
• 2017$13,681 tax · $225,000 assessed

Home value

$756,500

• Cotality$756,500
• Collateral Analytics$785,000
• Quantarium$753,546

Where it is