Chestertown MD Real Estate & Homes for Rent

Exceptional home for rent in the quiet waterfront community of Great Oak Estates. Fully furnished. Multiple primary floor bedrooms. Open floor plan. Fantastic outdoor living space. Expansive river views from every room. Private dock on Fairlee Creek. Great access to Great Oak Marina, Par 3 Golf Course and the Chesapeake Bay. This is a short term rental from the end of October to the end of April. Owner occupied the rest of the year.

MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, flooring recently upgraded, beautifully tiled bathroom, Pergo wood flooring. Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings fireplace, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar. just a very quick trip to entertainment, dining or boating. Great location, just 10 minutes from downtown Chestertown or Rock Hall where you can enjoy shops, marinas, dining and regular events. Level lot with plenty of potential.

Beautiful cape in a peaceful setting. 3 bed and 2 baths. Updated kitchen. Fireplace with built in book shelves in the living room. Lovely screened in porch overlooking the private back yard. Credit score of at least 700 required. No pets. No smoking.

Immaculate 3 bedroom, 1.5 bathroom townhouse available for rent! Rent includes water/sewer and lawn care. All you have to do is move in! Apply using online rent spree link. To qualify applicants must have 580+ credit and gross income near 3X rent. No pets permitted. Tenant occupied until the end of July and will be available for occupancy by mid August.

Welcome home to historic Overbeck! This beautiful old home overlooks an expansive yard and on to the Chester River. The small beach is a perfect launch site for your paddle boards and kayaks. Inside find fireplaces, hardwood floors on main level along with brick floored sunroom. Great big fireplace in Kitchen then up a few stairs to formal dining room . Cozy living room with covered porch on waterside to sit and take in the gorgeous views. The Eastern Shores abundant wildlife surrounds this very private home.* There will be no hunting allowed.*This lease includes the property from the Chester Rivers waterline to include the tree lined lane. Call for details and availability. Do not enter property without an appointment!

Move in ready 2nd floor apartment in Downtown Chestertown. One spacious bedroom, full bathroom, living area and a step-up cove/office space. Conveniently located within walking distance to the Chester River. Utilities included with the exception of Internet/Cable. All applicants apply through Rent Spree.