115 Flying Cloud Dr, Chestertown, MD 21620
OFF MARKET

$343,600

Trulia Estimate
  • Studio
  • 3 Baths
  • 1,930 sqft

115 Flying Cloud Dr, Chestertown, MD 21620

Est. Refi. Payment $2,044/mo*
Refinance Your Home
Currently Off Market - Sold Jul 11, 2023 for $319,990

Home Value

Trulia Estimate
$344K
Since last month
Decreased$4K (-1%)
Since last year
Decreased$5K (-1.5%)
Since last sale
Increased$24K (+7.6%)
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
August 2026$344K
August 2026$344K
July 2026$348K
June 2026$354K
May 2026$354K
April 2026$351K
March 2026$349K
February 2026$346K
January 2026$344K
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
103 Flying Cloud Dr, Chestertown, MD
0.06
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
0.06
Single-Family Home
$324,000
08/14/26
3
2.5
1,896
108 Flying Cloud Dr, Chestertown, MD
0.04
Single-Family Home
$364,900
02/26/26
4
2.5
1,936
107 Flying Cloud Dr, Chestertown, MD
0.04
Single-Family Home
$380,000
08/18/26
5
3.5
2,534
112 Silver Heel Dr, Chestertown, MD
0.12
Single-Family Home
$379,900
01/21/26
5
3.5
2,615
126 Metcalf Rd, Chestertown, MD
0.11
Single-Family Home
$230,000
11/20/25
3
2
1,140
109 Cedar St, Chestertown, MD
0.34
Single-Family Home
$318,000
08/14/26
3
2
1,397
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
0.31
Single-Family Home
$300,000
07/30/26
4
2
1,325

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
110 Flying Cloud Dr, Chestertown, MD 21620
0.03
$335,000
3
2.5
1,856
Recently Sold
113 Flying Cloud Dr, Chestertown, MD 21620
0.01
$332,400
3
2.5
1,646
Off Market
216 Silver Heel Rd, Chestertown, MD 21620
0.06
$360,900
3
2.5
1,724
Off Market
108 Flying Cloud Dr, Chestertown, MD 21620
0.04
$364,900
4
2.5
1,936
Recently Sold
117 Chester Arms Dr, Chestertown, MD 21620
0.07
$268,900
3
1.5
1,260
Off Market
115 Chester Arms Dr, Chestertown, MD 21620
0.07
$263,000
3
2
1,140
For Sale
107 Flying Cloud Dr, Chestertown, MD 21620
0.04
$380,000
5
3.5
2,534
Recently Sold
107 Chester Arms Dr, Chestertown, MD 21620
0.08
$230,400
3
2
1,140
Off Market
102 Flying Cloud Dr, Chestertown, MD 21620
0.06
$324,000
3
2.5
1,896
Recently Sold
206 Silver Heel Dr, Chestertown, MD 21620
0.08
$376,600
5
3.5
2,302
Off Market
103 Flying Cloud Dr, Chestertown, MD 21620
0.06
$339,900
3
2.5
1,724
Recently Sold
126 Metcalf Rd, Chestertown, MD 21620
0.11
$230,000
3
2
1,140
Recently Sold

Local Information

  • Map ViewExplore the area around 115 Flying Cloud Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2023
Living Area
1,930 sqft
Price/Sqft
$178

About this House

This single-family home is located at 115 Flying Cloud Dr, Chestertown, MD. 115 Flying Cloud Dr is in Chestertown, MD and in ZIP code 21620. This property has 3 bathrooms and approximately 1,930 sqft of floor space. This property has a lot size of 5392 sqft and was built in 2023.
115 Flying Cloud Dr, Chestertown, MD 21620 is a studio, 3 bathroom, 1,930 sqft single-family home built in 2023. It last sold for $319,990 on Jul 11, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $343,600, with a rent estimate of $2,466/month.

Home Details for 115 Flying Cloud Dr

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Other

Property Information

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

Community

Units in Building: 1

Lot Information

Lot Area: 5392 sqft

Price and Tax history

DateEventPrice
Jul 11, 2023
Source: Bright MLS #MDKE2003020
Sold
$319,990

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 115 Flying Cloud Dr

  • What is 115 Flying Cloud Dr estimated to be worth?
    Trulia's estimated value for 115 Flying Cloud Dr in Chestertown, MD is $343,600.
  • What is the price history for 115 Flying Cloud Dr?
    115 Flying Cloud Dr in Chestertown, MD last sold for $319,990 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.
  • How big is the lot at 115 Flying Cloud Dr?
    The lot at 115 Flying Cloud Dr in Chestertown, MD is about 0.12 acres (5,392 sq ft).

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