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

$363,500

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 1,936 sqft

108 Flying Cloud Dr, Chestertown, MD 21620

Est. Refi. Payment $2,255/mo*
Refinance Your Home
Currently Off Market - Sold Feb 26, 2026 for $364,900

Home Value

Trulia Estimate
$364K
Since last month
Decreased$2K (-0.5%)
Since last year
Increased$17K (+4.8%)
Since last sale
Decreased$1K (-0.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +6% in the last 10 years
MonthEstimated value
2026
September 2026$364K
August 2026$365K
July 2026$370K
June 2026$371K
May 2026$368K
April 2026$366K
March 2026$365K
February 2026$365K
January 2026$360K
2025
2024
2023

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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
102 Flying Cloud Dr, Chestertown, MD
0.03
Single-Family Home
$324,000
08/14/26
3
2.5
1,896
103 Flying Cloud Dr, Chestertown, MD
0.04
Single-Family Home
$339,900
04/21/26
3
2.5
1,724
107 Flying Cloud Dr, Chestertown, MD
0.02
Single-Family Home
$380,000
08/18/26
5
3.5
2,534
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
109 Cedar St, Chestertown, MD
0.36
Single-Family Home
$318,000
08/14/26
3
2
1,397
411 Greenwood Ave, Chestertown, MD
0.43
Single-Family Home
$415,000
01/07/26
3
2.5
1,676

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
103 Flying Cloud Dr, Chestertown, MD 21620
0.04
$339,900
3
2.5
1,724
Recently Sold
107 Flying Cloud Dr, Chestertown, MD 21620
0.02
$380,000
5
3.5
2,534
Recently Sold
102 Flying Cloud Dr, Chestertown, MD 21620
0.03
$324,000
3
2.5
1,896
Recently Sold
110 Flying Cloud Dr, Chestertown, MD 21620
0.01
$335,000
3
2.5
1,856
Recently Sold
206 Silver Heel Dr, Chestertown, MD 21620
0.04
$376,600
5
3.5
2,302
Off Market
107 Chester Arms Dr, Chestertown, MD 21620
0.05
$229,500
3
2
1,140
Off Market
110 Island Lark Way, Chestertown, MD 21620
0.10
$256,500
3
2.5
1,365
Off Market
108 Island Lark Way, Chestertown, MD 21620
0.10
$274,100
3
2.5
1,365
Off Market
116 Island Lark Way, Chestertown, MD 21620
0.11
$287,300
3
2.5
1,420
Off Market
118 Island Lark Way, Chestertown, MD 21620
0.11
$285,400
3
2.5
1,365
Off Market
112 Island Lark Way, Chestertown, MD 21620
0.11
$250,900
3
2.5
1,365
Off Market

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

Single-Family Home
Built in 2023
1,936 sqft
$188/sqft
Open Parking
HOA $70/mo

About this House

What's unique:Stylish backsplashSmart homeFour spacious bedroomsUpgraded sink and faucet
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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $363,500, with a rent estimate of $2,668/month.
Last check for updates: about 16 hours 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

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

Price and Tax history

DateEventPrice
Feb 26, 2026
Source: Bright MLS #MDKE2005928
Sold
$364,900
Feb 17, 2026
Source: Bright MLS #MDKE2005928
Pending
$364,900
Jan 25, 2026
Source: Bright MLS #MDKE2005928
Contingent
$364,900
Dec 14, 2025
Source: Bright MLS #MDKE2005928
PriceChange
$364,900
Price decreased by 3%
Nov 19, 2025
Source: Bright MLS #MDKE2005928
Listed For Sale
$375,000

Market trends in Chestertown

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

Around this home

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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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

Frequently asked questions about 108 Flying Cloud Dr

  • What is 108 Flying Cloud Dr estimated to be worth?
    Trulia's estimated value for 108 Flying Cloud Dr in Chestertown, MD is $363,500.
  • What is the price history for 108 Flying Cloud Dr?
    108 Flying Cloud Dr in Chestertown, MD last sold for $364,900 in February 2026.
  • Is Chestertown a buyer's or seller's market?
    Chestertown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chestertown?
    Residents describe Chestertown, MD as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Chestertown, MD.
  • Does 108 Flying Cloud Dr have air conditioning?
    Yes, 108 Flying Cloud Dr in Chestertown, MD has air conditioning.
  • Does 108 Flying Cloud Dr have laundry facilities?
    Yes, 108 Flying Cloud Dr in Chestertown, MD has in-unit laundry.

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