108 Flying Cloud Dr, Chestertown, MD 21620
Property image
Property image
SOLD
FEB 26, 2026

108 Flying Cloud Dr
Chestertown, MD 21620

  • 4 Beds
  • 2.5 Baths
  • 1,936 sqft

$364,900

Last Sold: Feb 26, 2026
$188/sqft
Est. Refi. Payment $2,187/mo*
Refinance Your Home

$364,900

Last Sold: Feb 26, 2026
$188/sqft
Est. Refi. Payment $2,187/mo*
Refinance Your Home
4 Beds
2.5 Baths
1,936 sqft

Local Information

  • Map ViewExplore the area around 108 Flying Cloud Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2023
Living Area
1,936 sqft
Price/Sqft
$188/sqft
Parking
Open Parking
HOA
$70/Monthly

About this House

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.
108 Flying Cloud Dr, Chestertown, MD 21620 is a 4 bedroom, 3 bathroom, 1,936 sqft single-family home built in 2023. It last sold for the $364,900 asking price on Feb 26, 2026. It is currently off market. The Trulia Estimate is $368,400, with a rent estimate of $2,567/month.

Home Details for 108 Flying Cloud Dr

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Laundry
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1936 Square Feet
Appliances & Utilities
Utilities: Fiber OpticAppliances: Dishwasher, Disposal, Dryer, Energy Efficient Appliances, Microwave, Oven/Range - Electric, Stainless Steel Appliance(s), Washer, Water Heater, Refrigerator, Electric Water HeaterDishwasherDisposalDryerLaundry: Dryer In Unit,Washer In Unit,Main Level,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,Programmable Thermostat,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Window TreatmentsFlooring: Carpet, Luxury Vinyl
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: 2+ Access ExitsFloors: Carpet, Luxury Vinyl
View
No View

Exterior Features

Exterior Home Features
Roof: Architectural ShinglePatio / Porch: PatioOther Structures: Above Grade, Below GradeFoundation: SlabNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Concrete,Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses
Finished Area
Finished Area (above surface): 1936 Square Feet

Property Information

Year Built
Year Built: 2023
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Contemporary
Building
Construction Materials: Batts Insulation, Blown-In Insulation, Concrete, Stick Built, Vinyl SidingNot a New ConstructionNo Additional Parcels
Property Information
Condition: ExcellentParcel Number: 1504338189

Price & Status

Price
List Price: $364,900Price Per Sqft: $188/sqft
Status Change & Dates
Off Market Date: Thu Feb 26 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: CHESTERTOWNCommunity: The Village At Chestertown
School Information
Elementary School District: Kent County Public SchoolsJr High / Middle School District: Kent County Public SchoolsHigh School District: Kent County Public Schools

Building

Building Details
Builder Model: SidneyBuilder Name: D.R. Horton
Building Area
Building Area: 1936 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: Common Area Maintenance, Maintenance Grounds, Road MaintenanceHas an HOAHOA Fee: $210/Quarterly

Lot Information

Lot Area: 4000 sqft

Listing Info

Special Conditions: Standard

Offer

Contingencies: Financing Approval, Home InspectionListing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDKE2005928Municipality: ChestertownAbove Grade Unfinished Area: 1936
Last check for updates: about 1 hour ago
Listed by Casey Scattergood, (201) 312-1230
Cross Street Realtors LLC
Bought with: Jenn Angel-Fuhlman, (443) 770-3383, Coldwell Banker Realty
Source: Bright MLS, MLS#MDKE2005928

Price History for 108 Flying Cloud Dr

DatePriceEventSource
02/26/2026$364,900Sold
Bright MLS #MDKE2005928
02/17/2026$364,900PendingBright MLS #MDKE2005928
01/25/2026$364,900ContingentBright MLS #MDKE2005928
12/14/2025$364,900PriceChange
Bright MLS #MDKE2005928
11/19/2025$375,000Listed For SaleBright MLS #MDKE2005928
07/20/2023$319,990Sold
Bright MLS #MDKE2002584
06/12/2023$319,990PendingBright MLS #MDKE2002584
06/02/2023$319,990PriceChange
Bright MLS #MDKE2002584
05/04/2023$347,070PriceChange
Bright MLS #MDKE2002584
04/24/2023$340,070PriceChange
Bright MLS #MDKE2002584
04/13/2023$329,990PriceChange
DR Horton
04/12/2023$337,990PriceChange
DR Horton
04/11/2023$329,990Listed For SaleBright MLS #MDKE2002584

Market trends in Chestertown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
5MoM
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Property Tax and Assessment

Year2025
Tax$9,074
Assessment$289,500
Home facts updated by county records

Comparable Sales for 108 Flying Cloud Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
110 Flying Cloud Dr, Chestertown, MD
0.01
Single-Family Home
$335,000
12/31/25
3
2.5
1,856
103 Flying Cloud Dr, Chestertown, MD
0.04
Single-Family Home
$339,900
04/21/26
3
2.5
1,724
206 Silver Heel Dr, Chestertown, MD
0.04
Single-Family Home
$375,000
08/13/25
5
3.5
2,302
112 Silver Heel Dr, Chestertown, MD
0.08
Single-Family Home
$379,900
01/21/26
5
3.5
2,615
126 Metcalf Rd, Chestertown, MD
0.09
Single-Family Home
$230,000
11/20/25
3
2
1,140
304 Hadaway Dr, Chestertown, MD
0.32
Single-Family Home
$300,000
07/30/26
4
2
1,325
411 Greenwood Ave, Chestertown, MD
0.43
Single-Family Home
$415,000
01/07/26
3
2.5
1,676
204 Rolling Rd, Chestertown, MD
0.47
Single-Family Home
$340,000
03/19/26
3
2
2,296
205 Pine St, Chestertown, MD
0.54
Single-Family Home
$296,337
09/30/25
3
1.5
2,212

Nearby homes

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Assigned Schools

These are the assigned schools for 108 Flying Cloud Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Chestertown

At least 34 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 84 % Say there's holiday spirit

  • 83 % Say it's dog friendly

  • 77 % Say people would walk alone at night

  • 77 % Say parking is easy

  • 76 % Say yards are well-kept

  • 74 % Say it's quiet

  • 61 % Say neighbors are friendly

  • 57 % Say there's wildlife

  • 56 % Say it's walkable to restaurants

  • 54 % Say there are sidewalks

  • 49 % Say kids play outside

  • 46 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

  • 41 % Say there are community events

  • 38 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
    1
    Flag
  • Trulia User
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
    1
    Flag
  • Trulia User
    "I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
    0
    Flag
  • Kesha C.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
    0
    Flag
  • Tracy W.
    "The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
    0
    Flag
  • Rancraw
    "This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
    9
    Flag
  • Acaldwell1297
    "I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
    1
    Flag
  • Guillermo A.
    "Good Community, friendly people, good services. "
    0
    Flag
  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
    5
    Flag
  • asso
    "Quiet - not for night owls. Nice farmer's market, good library. Easy acess for weekends in DC, Baltimore, Philly, & Ocean Beaches. College town, Chester River"
    0
    Flag
  • Dafoster
    "Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
    5
    Flag

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Homes for sale near 108 Flying Cloud Dr

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Off Market Homes Near 108 Flying Cloud Dr

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information