107 Flying Cloud Drive

Chestertown MD 21620

2534 sq. ft.

4969 sq. ft.

Single-Family

Last sold for $380,000

Cynthia Gardner, last sold this property on 18 August 2026 after 94 days on market.

Overview

NEW PRICE – One of Chestertown's Best Values! Over 2,500 square feet of 2023 construction priced comparably to many older Chestertown homes with just 1,200–1,800 square feet. If you're looking for maximum living space, modern design, and exceptional value, this home deserves a closer look. This move-in ready, three-story home offers 5 bedrooms, 3.5 baths, and 2,535 square feet of thoughtfully designed living space. The inviting front porch welcomes you into an open-concept main level featuring a spacious family room, dining area, and a bright kitchen designed for everyday living and entertaining. Highlights include stainless steel appliances, a generous peninsula, large corner pantry, first-floor laundry, and convenient powder room. The private owner's suite features a spacious walk-in closet and en-suite bath with double vanity and walk-in shower. Three additional bedrooms share a full bath with double vanity, while the finished third level provides a fifth bedroom, full bath, and flexible bonus space perfect for a home office, media room, playroom, fitness area, or guest suite. Ample closet space throughout provides exceptional storage. Unlike many homes in the community, this property backs to mature trees rather than neighboring homes, offering a more private backyard setting. Additional features include a modern Smart Home Package for convenience, efficiency, and peace of mind. Seller is offering a buyer credit toward allowable closing costs, helping conserve cash after settlement for future backyard enhancements such as a patio, fencing, or shed. Enjoy the beautifully landscaped community pond with fountain and the convenience of being just minutes from historic downtown Chestertown, Washington College, waterfront parks, restaurants, shopping, and year-round community events. The Village of Chestertown is now a completed community with no future construction—offering the opportunity to enjoy an established neighborhood from day one. Compare the square footage, age, and features, then come see why this home represents one of the best values currently available in the Chestertown market.

Features

5 bedrooms

4 bathrooms

2 carspaces

2534 sq. ft. floor area

4969 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Chestertown over the last 12 months, the estimated median property value of 107 Flying Cloud Drive is $1.1m.

Median value

$1.1m

Estimated value range

$379.9k - $4.22m

Median days on market

Estimated value trend

83%

increase over the last 12 months

Average days on market is based on recent, comparable sales in Chestertown. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 107 Flying Cloud Drive

2026

Sold

$380,000

18 Aug 2026 by Cynthia Gardner, of CENTURY 21 New Millennium

2023

Sold

$344,990

29 Aug 2023 by Kathleen Cassidy, of DRH Realty Capital, LLC.

Happy sellers in Chestertown

We have insufficient information to provide an overview of customer satisfaction for Chestertown. Viewing the agent profiles, reviews and sales for Chestertown can provide insights for this location.