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Under contract
    • Price cut: $10K (7/6)
    $375,000

    107 Flying Cloud Dr, Chestertown, MD 21620

    5beds
    2,534sqft
    : 
    $2,579/mo
    Get pre-qualified
    Single Family Residence
    Built in 2023
    4,969 Square Feet Lot
    $-- Zestimate®
    $148/sqft
    $70/mo HOA

    What's special

    Curb appealSpacious walk-in closetConvenient first-floor laundry roomPowder roomWell-designed architectural elevationsDining areaSpacious family room
    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.
    69 days
    |
    551
    |
    22
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    Zillow last checked:

    Listing updated:

    Listed by:

    Cindy Gardner 410-703-9202,

    CENTURY 21 New Millennium 4102669005

    Source: Bright MLS,MLS#: MDKE2006510MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      • Main level bathrooms: 4
      • Main level bedrooms: 5
      Heating
      • Forced Air, Programmable Thermostat, Electric
      Cooling
      • Central Air, Programmable Thermostat, Electric
      Appliances
      • Included: Dishwasher, Disposal, Dryer, Energy Efficient Appliances, Microwave, Oven/Range - Electric, Refrigerator, Stainless Steel Appliance(s), Washer, Water Heater, Electric Water Heater
      • Laundry: Dryer In Unit, Main Level, Washer In Unit
      Features
      • Bathroom - Stall Shower, Bathroom - Tub Shower, Combination Dining/Living, Open Floorplan, Eat-in Kitchen, Pantry, Primary Bath(s), Recessed Lighting, Walk-In Closet(s), Dry Wall
      • Flooring: Carpet, Luxury Vinyl
      • Windows: Window Treatments
      • Has basement: No
      • Has fireplace: No
      Interior area
      • Total structure area: 2,534
      • Total interior livable area: 2,534 sqft
      • Finished area above ground: 2,534

      Property

      Parking
      • Total spaces: 2
      • Parking features: Concrete, Driveway, On Street
      • Uncovered spaces: 2
      Accessibility
      • Accessibility features: 2+ Access Exits
      Features
      • Levels: Three
      • Stories: 3
      • Patio & porch: Porch
      • Exterior features: Sidewalks
      • Pool features: None
      Lot
      • Size: 4,969 Square Feet
      • Features: Backs to Trees, Interior Lot, Front Yard, Landscaped, Wooded
      Details
      • Additional structures: Above Grade
      • Parcel number: 1504338278
      • Zoning: R3/R4
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Contemporary
      • Property subtype: Single Family Residence
      Materials
      • Batts Insulation, Blown-In Insulation, Concrete, Stick Built, Vinyl Siding
      • Foundation: Slab
      • Roof: Architectural Shingle
      Condition
      • Excellent
      • New construction: No
      • Year built: 2023
      Details
      • Builder model: Verona
      • Builder name: D.R. Horton

      Utilities & green energy

      • Electric: 200+ Amp Service
      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available, Phone Available

      Community & HOA

      Community
      • Security: Fire Alarm, Smoke Detector(s), Fire Sprinkler System, Security System
      • Subdivision: The Village At Chestertown
      HOA
      • Has HOA: Yes
      • Amenities included: Common Grounds
      • Services included: Common Area Maintenance, Maintenance Grounds, Road Maintenance
      • HOA fee: $210 quarterly
      • HOA name: VILLAGE AT CHESTERTOWN
      Location
      • Region: Chestertown
      • Municipality: Chestertown

      Financial & listing details

      • Price per square foot: $148/sqft
      • Tax assessed value: $329,800
      • Annual tax amount: $5,390
      • Date on market: 5/16/2026
      • Listing agreement: Exclusive Right To Sell
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Road surface type: Black Top

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/20/2026Contingent$375,000$148/sqft
        Source: Bright MLS #MDKE2006510 Report a problem
        7/6/2026Price change$375,000-2.6%$148/sqft
        Source: Bright MLS #MDKE2006510 Report a problem
        6/9/2026Price change$385,000-2.5%$152/sqft
        Source: Bright MLS #MDKE2006510 Report a problem
        5/16/2026Listed for sale$395,000+14.5%$156/sqft
        Source: Bright MLS #MDKE2006510 Report a problem
        8/29/2023Sold$344,990$136/sqft
        Source: Bright MLS #MDKE2002770 Report a problem
        7/17/2023Pending sale$344,990$136/sqft
        Source: Bright MLS #MDKE2002770 Report a problem
        7/7/2023Price change$344,990-1.4%$136/sqft
        Source: Bright MLS #MDKE2002770 Report a problem
        7/5/2023Price change$349,990-9.3%$138/sqft
        Source: Bright MLS #MDKE2002770 Report a problem
        6/1/2023Listed for sale$385,945$152/sqft
        Source: Bright MLS #MDKE2002770 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$10,779 +100%$343,900
        2024$5,390 $343,900
        2023$5,390 +939.4%$343,900 +932.7%
        2022$519 -0.6%$33,300
        2021$522 $33,300
        2020$522 +0.2%$33,300
        2019$521 +0.6%$33,300
        2018$517 +3.3%$33,300
        2017$501 -55.9%$33,300
        2016$1,136 $33,300
        2015$1,136 $33,300 -26.5%
        2014$1,136 $45,300
        2013-- $45,300
        2012-- $45,300 -40%
        2011-- $75,500 -13.2%
        2010-- $87,000 +16.3%
        2009-- $74,832 +19.4%
        2008-- $62,666
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 21620

        Getting around

        31 / 100
        Car-Dependent
        30 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: H. H. Garnett
        • Middle: Kent County
        • High: Kent County
        • District: Kent County Public Schools

        Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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