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

$391,900

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 2,302 sqft

104 Flying Cloud Dr, Chestertown, MD 21620

Est. Refi. Payment $2,329/mo*
Refinance Your Home
Currently Off Market - Sold Jun 16, 2023 for $345,000

Home Value

Trulia Estimate
$392K
Since last month
Decreased$700 (-0.2%)
Since last year
Increased$6K (+1.6%)
Since last sale
Increased$47K (+13.5%)
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 +3% in the last 10 years
MonthEstimated value
2026
August 2026$392K
July 2026$392K
June 2026$392K
May 2026$393K
April 2026$396K
March 2026$389K
February 2026$381K
January 2026$375K
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
0.07
Single-Family Home
$379,900
01/21/26
5
3.5
2,615
107 Flying Cloud Dr, Chestertown, MD
0.02
Single-Family Home
$380,000
08/18/26
5
3.5
2,534
108 Flying Cloud Dr, Chestertown, MD
0.02
Single-Family Home
$364,900
02/26/26
4
2.5
1,936
102 Flying Cloud Dr, Chestertown, MD
0.01
Single-Family Home
$324,000
08/14/26
3
2.5
1,896
110 Flying Cloud Dr, Chestertown, MD
0.03
Single-Family Home
$335,000
12/31/25
3
2.5
1,856
103 Flying Cloud Dr, Chestertown, MD
0.03
Single-Family Home
$339,900
04/21/26
3
2.5
1,724
126 Metcalf Rd, Chestertown, MD
0.10
Single-Family Home
$230,000
11/20/25
3
2
1,140
109 Cedar St, Chestertown, MD
0.38
Single-Family Home
$318,000
08/14/26
3
2
1,397
411 Greenwood Ave, Chestertown, MD
0.45
Single-Family Home
$415,000
01/07/26
3
2.5
1,676
204 Rolling Rd, Chestertown, MD
0.49
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
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
0.01
$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
0.04
$376,600
5
3.5
2,302
Off Market
107 Chester Arms Dr, Chestertown, MD 21620
0.05
$230,400
3
2
1,140
Off Market
110 Island Lark Way, Chestertown, MD 21620
0.08
$256,500
3
2.5
1,365
Off Market
108 Island Lark Way, Chestertown, MD 21620
0.08
$274,000
3
2.5
1,365
Off Market
116 Island Lark Way, Chestertown, MD 21620
0.09
$287,300
3
2.5
1,420
Off Market
118 Island Lark Way, Chestertown, MD 21620
0.09
$284,500
3
2.5
1,365
Off Market
112 Island Lark Way, Chestertown, MD 21620
0.09
$250,800
3
2.5
1,365
Off Market

Local Information

  • Map ViewExplore the area around 104 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
2,302 sqft
$170/sqft

About this House

The Verona, a 2,302 square foot, three-story move-in ready home, offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, classic white cabinets, a large corner pantry and a peninsula island with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers a fifth bedroom and a third full bathroom, as well as a flex room that could be used for storage. The Verona includes a washer and dryer, a white window treatment package, and the exclusive Smart Home® 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.
104 Flying Cloud Dr, Chestertown, MD 21620 is a 5 bedroom, 4 bathroom, 2,302 sqft single-family home built in 2023. It last sold for $345,000 on Jun 16, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $391,900, with a rent estimate of $3,101/month.

Home Details for 104 Flying Cloud Dr

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 3

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Other
Parking & Garage
Parking Spaces: 2

Property Information

Year Built
Year Built: 2023
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 4000 sqft

Price and Tax history

DateEventPrice
Jun 24, 2026
Source: Bright MLS #MDKE2006212
ListingRemoved
$394,900
May 14, 2026
Source: Bright MLS #MDKE2006212
PriceChange
$394,900
Price decreased by 1%
Apr 2, 2026
Source: Bright MLS #MDKE2006212
Listed For Sale
$399,900
Jun 16, 2023
Source: Bright MLS #MDKE2002582
Sold
$345,000
May 15, 2023
Source: Bright MLS #MDKE2002582
Pending
$378,945

Market trends in Chestertown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
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

Frequently asked questions about 104 Flying Cloud Dr

  • What is 104 Flying Cloud Dr estimated to be worth?
    Trulia's estimated value for 104 Flying Cloud Dr in Chestertown, MD is $391,900.
  • What is the price history for 104 Flying Cloud Dr?
    104 Flying Cloud Dr in Chestertown, MD last sold for $345,000 in June 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.
  • How big is the lot at 104 Flying Cloud Dr?
    The lot at 104 Flying Cloud Dr in Chestertown, MD is about 0.09 acres (4,000 sq ft).
  • Does 104 Flying Cloud Dr have parking?
    Yes, 104 Flying Cloud Dr in Chestertown, MD has on-site parking.

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