Search location…
102 Flying Cloud Drive photo 1
for sale
41 photos
1 / 41
102 Flying Cloud Drive photo 2
2 / 41
102 Flying Cloud Drive photo 3
3 / 41
102 Flying Cloud Drive photo 4
4 / 41
102 Flying Cloud Drive photo 5
5 / 41
102 Flying Cloud Drive photo 6
6 / 41
102 Flying Cloud Drive photo 7
7 / 41
102 Flying Cloud Drive photo 8
8 / 41
102 Flying Cloud Drive photo 9
9 / 41
102 Flying Cloud Drive photo 10
10 / 41
102 Flying Cloud Drive photo 11
11 / 41
102 Flying Cloud Drive photo 12
12 / 41
102 Flying Cloud Drive photo 13
13 / 41
102 Flying Cloud Drive photo 14
14 / 41
102 Flying Cloud Drive photo 15
15 / 41
102 Flying Cloud Drive photo 16
16 / 41
102 Flying Cloud Drive photo 17
17 / 41
102 Flying Cloud Drive photo 18
18 / 41
102 Flying Cloud Drive photo 19
19 / 41
102 Flying Cloud Drive photo 20
20 / 41
102 Flying Cloud Drive photo 21
21 / 41
102 Flying Cloud Drive photo 22
22 / 41
102 Flying Cloud Drive photo 23
23 / 41
102 Flying Cloud Drive photo 24
24 / 41
102 Flying Cloud Drive photo 25
25 / 41
102 Flying Cloud Drive photo 26
26 / 41
102 Flying Cloud Drive photo 27
27 / 41
102 Flying Cloud Drive photo 28
28 / 41
102 Flying Cloud Drive photo 29
29 / 41
102 Flying Cloud Drive photo 30
30 / 41
102 Flying Cloud Drive photo 31
31 / 41
102 Flying Cloud Drive photo 32
32 / 41
102 Flying Cloud Drive photo 33
33 / 41
102 Flying Cloud Drive photo 34
34 / 41
102 Flying Cloud Drive photo 35
35 / 41
102 Flying Cloud Drive photo 36
36 / 41
102 Flying Cloud Drive photo 37
37 / 41
102 Flying Cloud Drive photo 38
38 / 41
102 Flying Cloud Drive photo 39
39 / 41
102 Flying Cloud Drive photo 40
40 / 41
102 Flying Cloud Drive photo 41
41 / 41

$329,900

3beds
|
3baths
|
1,896sqft
|
2023built
102 Flying Cloud Drive,Chestertown, MD 21620

Est.$2,169/moCustomize payment

What's special

$174/sqft

Price per square foot

Newer construction

Built in 2023

Overview

Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an open 1st floor features a bright white kitchen and dining area open to a large living room for entertaining and a 1/2 bathroom. The 2nd floor features 3 bedrooms 2 full bathrooms. The primary feature private bath and large closet. The exterior has large backyard for friends and family concrete driveway and freshly manicured yard. Call today for private showing today.

Listing updated: June 20, 2026 at 2:27 AM

Listed by:

Daniel B Foster 4103103393, Long & Foster Real Estate, Inc.

Source: Bright MLS · MLS #MDKE2006586Bright MLS

Property details

Cost estimate

Est. monthly payment

$2,283/mo
Principal & interest
$1,729
Property tax
$373
Home insurance (est.)
$110
HOA fee
$70

Down payment

$65,98020% of list price
Adjust down payment20%
0%25%50%

Based on 20% down ($65,980), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.

Rates provided by Mable Loans.

Customize scenario

Price history

DateEventPrice
Jun 20, 2026Price reduced$329,900($10,000)
May 19, 2026Listed for sale$339,900

Location

102 Flying Cloud Drive, Chestertown, MD 21620

Recently sold nearby

Similar homes sold within 0.5 miles in the last 90 days.

This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

Nearby homes

$329,900

3 beds · 3 baths · 1,896 sqft

Bright MLS

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Samson Properties participates, and is provided by BRIGHT through a licensing agreement. © 2026 Bright MLS, All Rights Reserved. Information deemed reliable but not guaranteed. The information provided by this website is for the personal, non-commercial use of consumers and 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 this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Data last updated: 7/2/2026.