112 Flying Cloud Dr, Chestertown, MD 21620
OFF MARKET

112 Flying Cloud Dr
Chestertown, MD 21620

  • 4 Beds
  • 2.5 Baths
  • 1,849 sqft

$352,100

Trulia Estimate
as of Jun 20, 2026
Est. Refi. Payment $2,051/mo*
Refinance Your Home

$352,100

Trulia Estimate
as of Jun 20, 2026
Est. Refi. Payment $2,051/mo*
Refinance Your Home
4 Beds
2.5 Baths
1,849 sqft

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

Move-in ready home in the Village at Chestertown! The Sidney is a 1,849 square foot open-concept two-story home, that features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your family to spend quality time together in the spacious family room, casual dining area and kitchen. The well-appointed kitchen showcases an abundance of classic birch cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room complete with a washer and dryer is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes the exclusive Smart Home® Package through ADT and a white window blind package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from July 29, 2023

Home Highlights

Parking
2 Open Spaces
Outdoor
Patio
A/C
Heating & Cooling
HOA
$60/Monthly
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 112 Flying Cloud Dr

Interior Features

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: 1849 Square Feet
Appliances & Utilities
Appliances: 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: Forced Air,Programmable Thermostat,ElectricHas CoolingAir Conditioning: Central Air,Programmable Thermostat,ElectricHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
No Fireplace
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 GradeFoundation: SlabNo Private Pool
Parking & Garage
Open Parking Spaces: 2No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Concrete,Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1849 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 SidingIs a New Construction
Property Information
Condition: ExcellentParcel Number: 1504338200

Price & Status

Price
List Price: $339,990
Status Change & Dates
Off Market Date: Sat Jul 29 2023Possession Timing: Negotiable

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: 1849 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: Common Area Maintenance, Maintenance Grounds, Road MaintenanceHas an HOAHOA Fee: $180/Quarterly

Lot Information

Lot Area: 4000 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDKE2002686Municipality: ChestertownAbove Grade Unfinished Area: 1849
Last check for updates: about 8 hours ago
Listed by Kathleen Cassidy, (667) 500-2488
D R Horton Realty of Virginia LLC
Bought with: Scott Schuetter, (410) 900-7668, Berkshire Hathaway HomeServices PenFed Realty
Source: Bright MLS, MLS#MDKE2002686

Price History for 112 Flying Cloud Dr

DatePriceEventSource
05/09/2026$2,500ListingRemovedZillow Rentals
04/22/2026$2,500PriceChange
Zillow Rentals
04/13/2026$2,700Listed For RentZillow Rentals
07/27/2023$319,990Sold
Bright MLS #MDKE2002686
06/15/2023$339,990PendingBright MLS #MDKE2002686
06/02/2023$339,990PriceChange
Bright MLS #MDKE2002686
05/09/2023$348,070Listed For SaleBright MLS #MDKE2002686

Market trends in Chestertown

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
1MoM
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Property Tax and Assessment

Year2025
Tax$9,378
Assessment$299,200
Home facts updated by county records

Homeowner tools

Estimated monthly rent$2,530/mo
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Homes for rent near 112 Flying Cloud Dr

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Comparable Sales for 112 Flying Cloud Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
108 Flying Cloud Dr, Chestertown, MD
0.02
Single-Family Home
$364,900
02/26/26
4
2.5
1,936
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
0.05
Single-Family Home
$339,900
04/21/26
3
2.5
1,724
206 Silver Heel Dr, Chestertown, MD
0.05
Single-Family Home
$375,000
08/13/25
5
3.5
2,302
112 Silver Heel Dr, Chestertown, MD
0.10
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
411 Greenwood Ave, Chestertown, MD
0.41
Single-Family Home
$415,000
01/07/26
3
2.5
1,676
304 Hadaway Dr, Chestertown, MD
0.30
Single-Family Home
$250,000
07/31/25
4
2
1,325
204 Rolling Rd, Chestertown, MD
0.45
Single-Family Home
$340,000
03/19/26
3
2
2,296
205 Pine St, Chestertown, MD
0.52
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 112 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 112 Flying Cloud Dr

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Off Market Homes Near 112 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
112 Flying Cloud Dr, Chestertown, MD 21620 is a 4 bedroom, 3 bathroom, 1,849 sqft single-family home built in 2023. This property is not currently available for sale. 112 Flying Cloud Dr was last sold on Jul 27, 2023 for $319,990 (6% lower than the asking price of $339,990). The current Trulia Estimate for 112 Flying Cloud Dr is $352,100.