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$380,000

  • Sold
  • Closed
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,534 Sq. Ft.
  • Updated 7 days ago
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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.

Full Property Details for 107 Flying Cloud Dr

General

  • Sold For: $380,000
  • HOA FEE: $70/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $5,390 (2026)
  • Status: Closed
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2006510
  • Added to Site: 102 day(s) ago

Interior

  • Interior Features: Bathroom - Stall Shower, Bathroom - Tub Shower, Carpet, Combination Dining/Living, Floor Plan - Open, Kitchen - Eat-In, Pantry, Primary Bath(s), Recessed Lighting, Walk-in Closet(s), Window Treatments
  • Appliances: Dishwasher, Disposal, Dryer, Energy Efficient Appliances, Microwave, Oven/Range - Electric, Refrigerator, Stainless Steel Appliances, Washer, Water Heater
  • Flooring: Carpet, Luxury Vinyl Plank

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Main Floor Baths: 4
  • Main - Full Baths: 3
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Main & Up: 5

Other Rooms

  • Laundry: Dryer In Unit, Main Floor, Washer In Unit

Additional Information

  • Shared Amenities: Common Grounds
  • Security/Safety: Fire Detection System, Smoke Detector, Sprinkler System - Indoor, Security System

Exterior

  • Exterior Features: Sidewalks
  • Porch/Patio/Deck: Porch(es)

Parking

  • Total Spaces: 2
  • Parking Features: Concrete Driveway
  • Parking Type: Driveway, On Street

Location

  • Municipality: Chestertown
  • County: KENT
  • Subdivision: THE VILLAGE AT CHESTERTOWN
  • Cross Streets: Scheeler Road
  • Driving Directions: Use GPS
  • Direction Faces: Southwest
  • Agricultural Dist: Kent County

School Information

  • School District: Kent County Public Schools
  • Elementary School: H. H. Garnett
  • Middle School: Kent County
  • High School: Kent County

Community

  • Association: Yes
  • Assoc. Name: VILLAGE AT CHESTERTOWN
  • Assoc. Fees Include: Common Area Maintenance, Lawn Maintenance, Road Maintenance
  • Pets Allowed: Yes
  • Pets: Cats OK, Dogs OK

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Programmable Thermostat
  • Cooling Fuel: Electric
  • Heating Type: 90% Forced Air, Programmable Thermostat
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Phone Available

Structural Information

  • Architectural Style: Contemporary
  • Structure Type: Detached
  • Builder: D.R. Horton
  • Model: Verona
  • Construction: Batts Insulation, Blown-In Insulation, Concrete, Stick Built, Vinyl Siding
  • Foundation: Slab
  • Roof: Architectural Shingle
  • Walls/Ceilings: Dry Wall
  • Stories Description: Main
  • Square Feet: 2,534
  • Sq. Ft. Source: Estimated
  • Living Area: 2,534 Sq. Ft.
  • Finished Above Grnd: 2,534 Sq. Ft.
  • Year Built: 2023
  • Year Built Source: Estimated
  • Property Condition: Excellent

Lot Features

  • Lot Size (Acres): 0.11
  • Lot Size (Sq. Ft.): 4,969
  • Lot Size Source: Estimated
  • Street/Road Desc.: Black Top
  • Zoning: R3/R4
  • Lot Description: Backs to Trees, Interior, Front Yard, Landscaping, Partly Wooded

Green Features

  • RFactor - Ceilings: R-38
  • RFactor - Walls: R-19

Financial Considerations

  • Price Per Sq. Ft.: $147.99
  • Association Fee: $210
  • Assoc Fee Freq.: Quarterly
  • Assessment Year: 2026
  • Tax w/Assessment: $329,800
  • Tax Amount: $5,390
  • Tax Year: 2026
  • Terms: Standard Sale

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 38

Listed by CENTURY 21 New Millennium, Cynthia F Gardner
Sold by RE/MAX Advantage Realty, Sharon Fisher

Listing agent

— 107 Flying Cloud Dr —

  • Cynthia F Gardner

    CENTURY 21 New Millennium

Listing Office Email: alicia.jenkins@c21nm.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 107 Flying Cloud Dr

School District:Kent County Public Schools
NameGradesDistance
H. H. Garnett Elementary School
320 Calvert Street, Chestertown, MD 21620
PK-51.1 mi
Kent County Middle School
402 East Campus Avenue, Chestertown, MD 21620
6-80.7 mi
Kent County High School
25301 Lambs Meadow Road, Worton, MD 21678
9-124.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 107 Flying Cloud Dr

Date
Details
Price
Change
Source
8/18/2026
Sold
$380,000
1.33%
MLS
7/06/2026
Price Reduced
$375,000
-2.6%
MLS
6/09/2026
Price Reduced
$385,000
-2.53%
MLS
5/16/2026
Listed
$395,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by CENTURY 21 New Millennium, Cynthia F Gardner
Sold by RE/MAX Advantage Realty, Sharon Fisher

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107 Flying Cloud Drive, Chestertown, MD 21620 (MLS# MDKE2006510) is a Single Family property that was sold at $380,000 on August 18, 2026. Want to learn more about 107 Flying Cloud Drive? Do you have questions about finding other Single Family real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.