107 Flying Cloud Dr, Chestertown, MD 21620
Property image
Property image
SOLD
AUG 18, 2026

$380,000

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 2,534 sqft

107 Flying Cloud Dr, Chestertown, MD 21620

Est. Refi. Payment $2,348/mo*
Refinance Your Home
Currently Off Market - Sold Aug 18, 2026 for $380,000 (1% above list price)

Home Value

Trulia Estimate
$380K
Since last month
Increased$6K (+1.6%)
Since last year
Decreased$7K (-1.9%)
Since last sale
Decreased$800 (-0.2%)
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 decreased by -2% in the last 10 years
MonthEstimated value
2026
September 2026$379K
August 2026$380K
July 2026$373K
June 2026$383K
May 2026$394K
April 2026$387K
March 2026$385K
February 2026$382K
January 2026$377K
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
112 Silver Heel Dr, Chestertown, MD
0.09
Single-Family Home
$379,900
01/21/26
5
3.5
2,615
108 Flying Cloud Dr, Chestertown, MD
0.02
Single-Family Home
$364,900
02/26/26
4
2.5
1,936
103 Flying Cloud Dr, Chestertown, MD
0.02
Single-Family Home
$339,900
04/21/26
3
2.5
1,724
110 Flying Cloud Dr, Chestertown, MD
0.03
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
126 Metcalf Rd, Chestertown, MD
0.12
Single-Family Home
$230,000
11/20/25
3
2
1,140
411 Greenwood Ave, Chestertown, MD
0.45
Single-Family Home
$415,000
01/07/26
3
2.5
1,676
109 Cedar St, Chestertown, MD
0.38
Single-Family Home
$318,000
08/14/26
3
2
1,397
204 Rolling Rd, Chestertown, MD
0.48
Single-Family Home
$340,000
03/19/26
3
2
2,296

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
0.02
$339,900
3
2.5
1,724
Recently Sold
102 Flying Cloud Dr, Chestertown, MD 21620
0.03
$324,000
3
2.5
1,896
Recently Sold
108 Flying Cloud Dr, Chestertown, MD 21620
0.02
$364,900
4
2.5
1,936
Recently Sold
110 Flying Cloud Dr, Chestertown, MD 21620
0.03
$335,000
3
2.5
1,856
Recently Sold
206 Silver Heel Dr, Chestertown, MD 21620
0.06
$376,600
5
3.5
2,302
Off Market
107 Chester Arms Dr, Chestertown, MD 21620
0.07
$230,400
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
$274,000
3
2.5
1,365
Off Market
116 Island Lark Way, Chestertown, MD 21620
0.10
$287,300
3
2.5
1,420
Off Market
118 Island Lark Way, Chestertown, MD 21620
0.10
$284,500
3
2.5
1,365
Off Market
112 Island Lark Way, Chestertown, MD 21620
0.10
$250,800
3
2.5
1,365
Off Market

Local Information

  • Map ViewExplore the area around 107 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
2,534 sqft
$150/sqft
2 Open Spaces
HOA $70/mo

About this House

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.
107 Flying Cloud Dr, Chestertown, MD 21620 is a 5 bedroom, 4 bathroom, 2,534 sqft single-family home built in 2023. It last sold for $380,000 on Aug 18, 2026 (1% above the $375,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $380,000, with a rent estimate of $3,301/month.
Last check for updates: about 15 hours ago
Listed by Cindy Gardner, (410) 703-9202
CENTURY 21 New Millennium
Bought with: Sharon Fisher, (443) 375-0689, RE/MAX Advantage Realty
Source: Bright MLS, MLS#MDKE2006510

Home Details for 107 Flying Cloud Dr

Interior Features

Beds & Baths
Number of Bedrooms: 5Main Level Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1Number of Bathrooms (main level): 4
Dimensions and Layout
Living Area: 2534 Square Feet
Appliances & Utilities
Utilities: Cable Available, Phone AvailableAppliances: Dishwasher, Disposal, Dryer, Energy Efficient Appliances, Microwave, Oven/Range - Electric, Refrigerator, Stainless Steel Appliance(s), Washer, Water Heater, Electric Water HeaterDishwasherDisposalDryerLaundry: Dryer In Unit,Main Level,Washer In UnitMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Programmable Thermostat,ElectricHas CoolingAir Conditioning: Central Air,Programmable Thermostat,ElectricHas HeatingHeating Fuel: Forced Air
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: 3Levels: ThreeAccessibility: 2+ Access ExitsFloors: Carpet, Luxury Vinyl
View
No View
Security
Security: Fire Alarm, Smoke Detector(s), Fire Sprinkler System, Security System

Exterior Features

Exterior Home Features
Roof: Architectural ShinglePatio / Porch: PorchOther Structures: Above GradeExterior: SidewalksFoundation: SlabNo Private Pool
Parking & Garage
Open Parking Spaces: 2No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Concrete,Driveway,On Street
Pool
Pool: None
Frontage
Road Surface Type: Black TopNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses
Finished Area
Finished Area (above surface): 2534 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: 1504338278

Price & Status

Price
List Price: $375,000Price Per Sqft: $150/sqft
Status Change & Dates
Off Market Date: Tue Aug 18 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

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

Building

Building Details
Builder Model: VeronaBuilder Name: D.R. Horton
Building Area
Building Area: 2534 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: Common Area Maintenance, Maintenance Grounds, Road MaintenanceHOA Name: VILLAGE AT CHESTERTOWNHas an HOAHOA Fee: $210/Quarterly

Lot Information

Lot Area: 4969 sqft

Listing Info

Special Conditions: Standard

Offer

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

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDKE2006510Municipality: ChestertownAbove Grade Unfinished Area: 2534

Additional Information

HOA Amenities: Common GroundsSource Internet Automated Valuation Display: NSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y

Price and Tax history

DateEventPrice
Aug 18, 2026
Source: Bright MLS #MDKE2006510
Sold
$380,000
Jul 20, 2026
Source: Bright MLS #MDKE2006510
Contingent
$375,000
Jul 6, 2026
Source: Bright MLS #MDKE2006510
PriceChange
$375,000
Price decreased by 3%
Jun 9, 2026
Source: Bright MLS #MDKE2006510
PriceChange
$385,000
Price decreased by 3%
May 16, 2026
Source: Bright MLS #MDKE2006510
Listed For Sale
$395,000

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

LGBTQ Local Legal Protections

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 107 Flying Cloud Dr

  • What is 107 Flying Cloud Dr estimated to be worth?
    Trulia's estimated value for 107 Flying Cloud Dr in Chestertown, MD is $380,000.
  • What is the price history for 107 Flying Cloud Dr?
    107 Flying Cloud Dr in Chestertown, MD last sold for $380,000 in August 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 107 Flying Cloud Dr have air conditioning?
    Yes, 107 Flying Cloud Dr in Chestertown, MD has air conditioning.
  • Does 107 Flying Cloud Dr have laundry facilities?
    Yes, 107 Flying Cloud Dr in Chestertown, MD has in-unit laundry.

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