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$364,900

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,936 Sq. Ft.
  • Updated 7 hours ago
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New Year, new home! No need to worry for years about the roof or mechanics!! Built in 2023 - this Smart Home is tucked into a quiet and friendly Chestertown community. Thoughtfully enhanced throughout, the kitchen shines with new quartz countertops, a stylish backsplash, upgraded sink and faucet, and added cabinetry with elegant hardware. Fresh light fixtures bring a warm glow to the living spaces, while the laundry room offers added function with quartz surfaces and extra storage. The powder room has been transformed with a stunning vanity and modern fixtures. The second floor offers four spacious bedrooms and two full baths. As a bonus, this property is a smart home, offering comfort and convenience at your fingertips. Just a short drive to multiple marinas in Rock Hall and an easy drive to Philadelphia and Washington, D.C.

Full Property Details for 108 Flying Cloud Dr

General

  • Price: $364,900
  • HOA FEE: $70/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $4,537 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2005928
  • Updated: 1/15/2026
  • Added to Site: 57 day(s) ago

Interior

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

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 4

Other Rooms

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

Exterior

  • Porch/Patio/Deck: Patio(s)

Parking

  • Parking Features: Concrete Driveway
  • Parking Type: Driveway

Location

  • Municipality: Chestertown
  • County: KENT
  • Subdivision: THE VILLAGE AT CHESTERTOWN
  • Cross Streets: Scheeler Road
  • Driving Directions: Follow GPS
  • Direction Faces: Northeast
  • City Limits: Yes

School Information

  • School District: Kent County Public Schools

Community

  • Association: Yes
  • Assoc. Fees Include: Common Area Maintenance, Lawn Maintenance, Road Maintenance

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Programmable Thermostat
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Contemporary
  • Structure Type: Detached
  • Builder: D.R. Horton
  • Model: Sidney
  • Construction: Batts Insulation, Blown-In Insulation, Concrete, Stick Built, Vinyl Siding
  • Foundation: Slab
  • Roof: Architectural Shingle
  • Walls/Ceilings: Dry Wall
  • Stories Description: Main, Upper 1
  • Square Feet: 1,936
  • Sq. Ft. Source: Assessor
  • Living Area: 1,936 Sq. Ft.
  • Finished Above Grnd: 1,936 Sq. Ft.
  • Year Built: 2023
  • Year Built Source: Assessor
  • Property Condition: Excellent

Lot Features

  • Lot Size (Acres): 0.09
  • Lot Size (Sq. Ft.): 4,000
  • Lot Size Source: Assessor
  • Zoning: R3/R4
  • Lot Description: Interior

Green Features

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

Financial Considerations

  • Price Per Sq. Ft.: $188.48
  • Association Fee: $210
  • Assoc Fee Freq.: Quarterly
  • Assessment Year: 2025
  • City/TownTax: $1,254
  • City/TownTax Freq: Annually
  • County Tax: $3,283
  • County Tax Freq: Annually
  • Tax w/Assessment: $289,500
  • Tax Amount: $4,537
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 1936

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 30

Listed by Cross Street Realtors LLC, Casey Scattergood

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Listing agent

— 108 Flying Cloud Dr —

  • Casey Scattergood

    Cross Street Realtors LLC

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 108 Flying Cloud Dr

School District:Kent County Public Schools
NameGradesDistance
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 Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 108 Flying Cloud Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/14/2025
Price Reduced
$364,900
-2.69%
MLS
11/19/2025
Listed
$375,000
17.19%
MLS
7/20/2023
Sold
$319,990
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 108 Flying Cloud Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,537
—
$289,500
—
2024
$4,537
774%
$289,500
—
2023
$519
—
$289,500
769%
2022
$519
-1%
$33,300
—
2020
$522
—
$33,300
—
2021
$522
—
$33,300
—
2020
$521
1%
$33,300
—
2019
$517
3%
$33,300
—
2018
$501
—
$33,300
—
2017
$501
307%
$33,300
—
2016
$123
-75%
$33,300
-26%
2015
$501
-26%
$45,300
—
2014
$681
—
$45,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Cross Street Realtors LLC, Casey Scattergood

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108 Flying Cloud Drive, Chestertown, MD 21620 (MLS# MDKE2005928) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 108 Flying Cloud Drive is currently listed for $364,900 and was received on November 19, 2025. Want to learn more about 108 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.

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