107 Flying Cloud Drive
Chestertown, MD 21620

$395,000

Beds: 5
Baths: 3 full 1 partial
Sq. Feet: 2534
MLS ID: MDKE2006510
Subdivision: THE VILLAGE AT CHESTERTOWN
School Dist: KENT COUNTY PUBLIC SCHOOLS
Welcome to this stunning 2023-built home with well-designed architectural elevations! The curb appeal captures your attention and the moment you arrive, the welcoming front porch invites you to slow down, relax, and imagine enjoying a glass of iced tea from your favorite wicker chair. Step through the handsome front door into a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,535 square feet of thoughtfully designed living space. The main level features an open-concept layout with a spacious family room, dining area, and bright, well-appointed kitchen — perfect for both everyday living and entertaining. A convenient first-floor laundry room and powder room add to the home’s functionality. The kitchen is designed with today’s lifestyle in mind, featuring stainless steel appliances, a generous peninsula for gathering, and a large corner pantry providing abundant storage. Upstairs, the owner’s suite offers a peaceful retreat with a walk-in closet and private en-suite bath complete with double vanity and walk-in shower. Three additional bedrooms share a full hall bath with double vanity, providing comfort and convenience for family or guests. The third level expands the home’s versatility with a fifth bedroom, full bath, and flexible bonus space ideal for a home office, playroom, media room, fitness area, or additional storage. Ample closets throughout ensure exceptional storage options. Extras you’ll love: a modern Smart Home Package offering convenience, efficiency, and peace of mind. The backyard backs to trees for added privacy, with plenty of room to add a shed, garage, or play equipment to suit your lifestyle. The thoughtfully landscaped community common area features a scenic pond with fountain, creating a welcoming neighborhood setting. Located just minutes from downtown Chestertown — known for its charming shops, restaurants, parks, waterfront atmosphere, and Washington College — you’ll enjoy easy access to date nights, community events, and small-town charm at its best. This thoughtfully planned community is complete, offering a wonderful opportunity to become part of an established neighborhood. Don’t miss your chance to make this exceptional home your own! View this listing at: http://janecummingsrealtor.com/mls=MDKE2006510

Property Features

School Information

Printed May 10, 2026


Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 05/10/2026. The listing information on this page last changed on 05/10/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sun 05/10/2026 12:48:38 AM EST) or Bright MLS (last updated Sun 05/10/2026 12:36:53 AM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
Privacy Policy / DMCA Notice / ADA Accessibility
Federal Housing Equal Opportunity Realtor
Corporate Office - 215 S Centerville Rd. Lancaster, PA 17603
James J Hafer - West Virginia Broker of Record

©2026 BHH Affiliates, LLC. An independently owned and operated franchisee of BHH Affiliates, LLC. Berkshire Hathaway HomeServices and the Berkshire Hathaway HomeServices symbol are registered service marks of Columbia Insurance Company, a Berkshire Hathaway affiliate. Equal Housing Opportunity.


Agent License Information: 
Licensed in Maryland
Jane Cummings 

1425 Clarkview Road, Suite 700, Baltimore, MD 21209
410-583-0400