NEW: Private hot tub available for stays beginning October 5, 2026!

Welcome to Pear Tree Point, a private waterfront retreat on the Chester River near historic Chestertown, Maryland. Relax in the 6-person hot tub on the covered deck, gather around the waterfront fire pit, or simply settle in and enjoy peaceful river views.

Perfect for families, couples, and small groups, the home offers plenty of space to be together while still giving everyone room to spread out.

Inside, the main level features a comfortable living area, fully equipped kitchen, and beautiful water views. Step outside onto the covered deck for morning coffee overlooking the river or an evening soak in the hot tub.

The walkout lower level provides a second family room with built-in bunk beds and a full bathroom, making it a great space for kids or additional guests. With two separate living areas, the home works especially well for families and groups traveling together.

Outside, enjoy the spacious waterfront property, fire pit, covered deck, and hot tub. Take in views of the Chester River on one side and horses grazing in the neighboring pasture on the other. Whether you're starting the morning by the water or winding down under the stars, it's a peaceful setting that feels removed from it all.

When you're ready to explore, pickleball, basketball, and tennis courts are less than half a mile away. Downtown Chestertown is just a short drive away, with local restaurants, shops, waterfront areas, and historic Eastern Shore charm.

Whether you're planning a family getaway, couples' weekend, or simply looking for a quiet waterfront escape, Pear Tree Point offers a comfortable home base for enjoying Maryland's Eastern Shore.

PROPERTY HIGHLIGHTS
• Private 6-person hot tub on the covered deck
• Waterfront setting with beautiful Chester River views
• Waterfront fire pit
• Covered deck and outdoor gathering spaces
• Two separate indoor living areas
• Walkout lower-level family room with built-in bunk beds
• Fully equipped kitchen
• Multiple bathrooms
• Less than 1/2 mile to pickleball, basketball, and tennis courts
• Short drive to historic downtown Chestertown
• Quiet, private setting

SLEEPING ARRANGEMENTS
• Primary bedroom – Queen Bed
• Bedroom 2 –Queen Bed
• Lower-level bunk area – Built-in bunk beds in the family room with Double Beds on the bottom level and single bunks above.

Guests have private access to the home and waterfront property during their stay. We're also happy to provide local recommendations for exploring Chestertown and Maryland's Eastern Shore.