105 Flying Cloud Dr, Chestertown, MD 21620
Property image
Property image
OFF MARKET

$354,000

Trulia Estimate
as of Sep 13, 2026
  • 4 Beds
  • 2.5 Baths
  • 1,849 sqft

105 Flying Cloud Dr, Chestertown, MD 21620

Home Highlights

Single-Family Home
1,849 sqft
$191/sqft

Local Information

  • Map ViewExplore the area around 105 Flying Cloud Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

A move-in ready 1,849 square-foot open concept two-story home, 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 stylish gray cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room 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.
* This is a NON-FURNISHED single family home.

- A non-refundable pet deposit will be collected at the time of lease signing.
-We will not accept a reusable tenant screening report and potential tenants will be required to pay for tenant screening report when requested to by landlord following their application.
-Tenants are required to carry renters insurance.
-There will be a non-refundable pet deposit of $250 per pet, collected at the time of lease commencement. Dogs can be up to 40.lbs unless otherwise agreed to by the landlord in writing and a maximum of two dogs. * if there is any urine damage, the flooring or carpet will be replaced in that room at the renters cost at the time of expiration of their lease from their security deposit.
-Person signing the lease must be the individual or individuals who will be residing in the property.
105 Flying Cloud Dr, Chestertown, MD 21620 is a 4 bedroom, 3 bathroom, 1,849 sqft single-family home. It last sold for $335,000 on Jul 28, 2023 (11,864% above the $2,800 asking price). More recently, it was listed as a rental in May 2025 with an asking price of $2,800 per month. That rental listing was removed on July 15, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $354,000, with a rent estimate of $2,658/month.

Home Details for 105 Flying Cloud Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Comparable Sales for 105 Flying Cloud Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
108 Flying Cloud Dr, Chestertown, MD
0.03
Single-Family Home
$364,900
02/26/26
4
2.5
1,936 sqft
103 Flying Cloud Dr, Chestertown, MD
0.01
Single-Family Home
$339,900
04/21/26
3
2.5
1,724 sqft
110 Flying Cloud Dr, Chestertown, MD
0.04
Single-Family Home
$335,000
12/31/25
3
2.5
1,856 sqft
102 Flying Cloud Dr, Chestertown, MD
0.02
Single-Family Home
$324,000
08/14/26
3
2.5
1,896 sqft
107 Flying Cloud Dr, Chestertown, MD
0.01
Single-Family Home
$380,000
08/18/26
5
3.5
2,534 sqft
112 Silver Heel Dr, Chestertown, MD
0.09
Single-Family Home
$379,900
01/21/26
5
3.5
2,615 sqft
126 Metcalf Rd, Chestertown, MD
0.12
Single-Family Home
$230,000
11/20/25
3
2
1,140 sqft
304 Hadaway Dr, Chestertown, MD
0.34
Single-Family Home
$300,000
07/30/26
4
2
1,325 sqft
109 Cedar St, Chestertown, MD
0.38
Single-Family Home
$318,000
08/14/26
3
2
1,397 sqft
411 Greenwood Ave, Chestertown, MD
0.45
Single-Family Home
$415,000
01/07/26
3
2.5
1,676 sqft

Nearby homes

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Rental Market Trends in Chestertown

Last updated Sep 2026
Trulia Rent Estimate$2,658/mo
Average rent
$1.82K
$103MoM
Available listings
4
View rental market trends in Chestertown, MD

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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Price and Tax history

DateEventPrice
Jul 15, 2025
Source: Zillow Rentals
ListingRemoved
$2,800
May 4, 2025
Source: Zillow Rentals
Listed For Rent
$2,800
Mar 7, 2025
Source: Zillow Rentals
ListingRemoved
$2,800
Feb 18, 2025
Source: Zillow Rentals
Listed For Rent
$2,800
Feb 7, 2025
Source: Zillow Rentals
ListingRemoved
$2,800

Frequently asked questions about 105 Flying Cloud Dr

  • What is 105 Flying Cloud Dr estimated to be worth?
    Trulia's estimated value for 105 Flying Cloud Dr in Chestertown, MD is $354,000.
  • What is the price history for 105 Flying Cloud Dr?
    105 Flying Cloud Dr in Chestertown, MD last sold for $335,000 in July 2023.
  • 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 105 Flying Cloud Dr have air conditioning?
    Yes, 105 Flying Cloud Dr in Chestertown, MD has air conditioning.
  • Does 105 Flying Cloud Dr have parking?
    Yes, 105 Flying Cloud Dr in Chestertown, MD has on-site parking.

Homes for rent near 105 Flying Cloud Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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