Open Houses in 21620

Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre

Peter Heller Coldwell Banker Chesapeake Real Estate Company

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

Nestled in the natural serene of Great Oak Estates, this beautiful 5 bedroom, 3.5 bathroom Nanicoke Home offers a flexible floor plan, updated kitchen, spacious backyard, and brand new Florida/Sun room, designed for both relaxation and entertaining. The heart of the home feautures a gourmet kitchen with granite counter tops, SS appliances, custom built ins, and connects to the family room with an

Michele Palmer Doug Ashley Realtors, LLC

Welcome to 208 Central Drive, located in the desirable Chester Harbor community just minutes from historic Chestertown. This charming 3-bedroom, 1-bath home offers a wonderful blend of comfort, convenience, and value. It sits on 3 lots totaling approximately 0.55 acres, surrounded by mature trees and landscaping. Step inside to a bright, move-in-ready interior featuring brand-new wood flooring

Jennifer Pogoda Redfin Corp

Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. More details and pictures

Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

Beautiful, Well-Maintained 3BR/2.5BA Home with Upgrades – 215 Fairview Drive Owner pride shines inside and out in this exceptional home located in the charming town of Chestertown, nestled in Queen Anne's County. Built in 2004 and offering 1,784 sq ft of living space, this property blends comfort, functionality, and thoughtful updates—perfect for today’s lifestyle. This inviting home features 3

Mary Julie Long & Foster Real Estate, Inc.