Riverside at Pear Tree Point--Waterfront Escape

Welcome to Pear Tree Point, a peaceful waterfront retreat near historic Chestertown, Maryland. Perfect for families, couples, and small groups, this relaxing getaway offers beautiful river views, spacious gathering areas, and the perfect setting to unwind, reconnect, and enjoy the Eastern Shore.

The home features comfortable living spaces, modern amenities, and plenty of room for everyone to spread out and relax. The main level includes an open living area, fully equipped kitchen, and water views throughout the home. Step outside to enjoy the peaceful outdoor spaces, morning coffee by the river, or evenings spent relaxing with family and friends.

The walkout lower level offers a second family room with built-in bunk beds and a full bathroom, creating a fun and flexible sleeping and hangout area that’s perfect for kids or additional guests. Two separate living areas make the home especially comfortable for families and groups traveling together.

Guests can enjoy nearby pickleball, basketball, and tennis courts located less than a half-mile away, or explore the shops, restaurants, waterfront, and small-town charm of nearby Chestertown just a short drive away.

Whether you're visiting for a relaxing waterfront escape, a family getaway, boating and outdoor activities, or a peaceful weekend on Maryland’s Eastern Shore, Pear Tree Point provides the perfect place to slow down and make lasting memories.

PROPERTY HIGHLIGHTS
• Waterfront setting with river views
• Spacious indoor and outdoor gathering spaces
• Walkout lower level with bunk bed area and second family room
• Fully equipped kitchen
• Multiple living areas perfect for families and groups
• Less than 1/2 mile to pickleball, basketball, and tennis courts
• Short drive to downtown Chestertown
• Quiet and private setting ideal for relaxing getaways

SLEEPING ARRANGEMENTS
• Bedroom 1 – [King/Queen bed]
• Bedroom 2 – [King/Queen bed]
• Lower level bunk area – Built-in bunk beds located in the lower-level family room

You’ll have full private access to the home during your stay. We’re happy to provide local recommendations to help you enjoy everything Chestertown and Maryland’s Eastern Shore have to offer.