Dustin Oldfather
Compass
(302) 393-2276
1,395 Total Sales
1 in Chestertown
$585,000 Price
102 Flying Cloud Dr Chestertown, MD 21620
Chestertown Area
3
Beds
2.5
Baths
1,896
Sq Ft
4,000
Sq Ft Lot
Highlights
- Colonial Architecture
- Property is in excellent condition
- Heat Pump System
- Central Air
About This Home
As of August 2026Welcome 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.
Last Agent to Sell the Property
(410) 479-3993 danbfoster@gmail.com Long & Foster Real Estate, Inc. Brokerage Phone: 4104793993 Listed on: 05/19/2026
Last Buyer's Agent
(410) 778-0330 kristina@cbchesapeake.com Coldwell Banker Chesapeake Real Estate Company
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Home Details
Home Type
- Single Family
Est. Annual Taxes
- $4,479
Year Built
- Built in 2023
Lot Details
- 4,000 Sq Ft Lot
- Property is in excellent condition
- Property is zoned R3/R4
HOA Fees
- $70 Monthly HOA Fees
Home Design
- Colonial Architecture
- Slab Foundation
- Architectural Shingle Roof
- Vinyl Siding
Interior Spaces
- 1,896 Sq Ft Home
- Property has 2 Levels
Kitchen
- Built-In Microwave
- Ice Maker
- Dishwasher
- Disposal
Bedrooms and Bathrooms
- 3 Bedrooms
Laundry
- Laundry on upper level
- Electric Dryer
- Washer
Parking
- Driveway
- On-Street Parking
Utilities
- Central Air
- Heat Pump System
- 200+ Amp Service
- Electric Water Heater
Community Details
- Association fees include common area maintenance, lawn maintenance
- The Village Of Chestertown HOA
- The Village At Chestertown Subdivision
Listing and Financial Details
- Tax Lot 27
- Assessor Parcel Number 1504338154
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
May 19, 2026
Closed on
Aug 14, 2026
Sold by
Rose Spada Amanda
Bought by
Seller's Agent
Dan Foster
Long & Foster Real Estate, Inc.
Buyer's Agent
Kristina Hyland
Coldwell Banker Chesapeake Real Estate Company
List Price
$339,900
Sold Price
$324,000
Premium/Discount to List
-$15,900
-4.68%
Views
72
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
44.78%
Original Mortgage
$307,800
Outstanding Balance
$307,800
Interest Rate
6.49%
Mortgage Type
New Conventional
Estimated Equity
$27,173
Purchase Details
Listed on
Apr 10, 2023
Closed on
Aug 29, 2023
Sold by
D R Horton Inc
Bought by
Spada Amanda Rose
Seller's Agent
Kathleen Cassidy
D R Horton Realty of Virginia LLC
Buyer's Agent
datacorrect BrightMLS
Non Subscribing Office
List Price
$314,990
Sold Price
$304,990
Premium/Discount to List
-$10,000
-3.17%
Views
286
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
2.06%
Original Mortgage
$279,294
Interest Rate
5.5%
Mortgage Type
FHA
Purchase Details
Closed on
Jul 14, 2022
Sold by
Ssa Properties Llc
Bought by
Dr Horton Inc
Purchase Details
Closed on
Nov 2, 2012
Sold by
Capstone Resdev Llc
Bought by
Chichester Landvest Llc
Purchase Details
Closed on
Jul 16, 2012
Sold by
Oak Street Llc
Bought by
Capstone Resdev Llc
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Chestertown, MD
-
Dustin Oldfather
-
Kara Leddy
Kara Leddy
Coldwell Banker Realty
(443) 494-8169
61 Total Sales
1 in Chestertown
$328,000 Price
-
Brenda Fornos
Brenda Fornos
Responds QuicklyTaylor Properties
(667) 230-5001
77 Total Sales
1 in Chestertown
$230,000 Price
-
John Burke
John Burke
Gunther-McClary Real Estate
(443) 252-2392
84 Total Sales
10 in Chestertown
$178K - $865K Price Range
-
Kimberly Taylor
Kimberly Taylor
Responds QuicklyAmerican Premier Realty, LLC
(667) 771-6705
123 Total Sales
1 in Chestertown
$499,900 Price
-
Frederick Golding
Frederick Golding
RE/MAX Advantage Realty
(667) 239-8179
107 Total Sales
1 in Chestertown
$275,000 Price
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $304,990 | Fidelity National Title | |
| Deed | $240,000 | None Listed On Document | |
| Special Warranty Deed | $357,000 | Bay National Title Co | |
| Trustee Deed | $850,000 | Bay National Title Company |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $279,294 | FHA |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 08/14/2026 08/14/26 | Sold | $324,000 | -1.8% | $171 / Sq Ft | |
| 06/19/2026 06/19/26 | Price Changed | $329,900 | -2.9% | $174 / Sq Ft | |
| 05/19/2026 05/19/26 | For Sale | $339,900 | +11.4% | $179 / Sq Ft | |
| 08/29/2023 08/29/23 | Sold | $304,990 | 0.0% | $185 / Sq Ft | View Prior Sale |
| 07/11/2023 07/11/23 | Pending | -- | -- | -- | |
| 07/07/2023 07/07/23 | Price Changed | $304,990 | -1.6% | $185 / Sq Ft | |
| 07/05/2023 07/05/23 | Price Changed | $309,990 | -3.1% | $188 / Sq Ft | |
| 06/02/2023 06/02/23 | Price Changed | $319,990 | -6.6% | $194 / Sq Ft | |
| 05/04/2023 05/04/23 | Price Changed | $342,480 | +2.1% | $208 / Sq Ft | |
| 04/24/2023 04/24/23 | Price Changed | $335,480 | +6.5% | $204 / Sq Ft | |
| 04/10/2023 04/10/23 | For Sale | $314,990 | -- | $191 / Sq Ft |
Source: Bright MLS
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2026 | $4,515 | $288,067 | ||
| 2025 | $4,479 | $285,800 | $80,300 | $205,500 |
| 2024 | $4,479 | $285,800 | $80,300 | $205,500 |
| 2023 | $4,479 | $285,800 | $80,300 | $205,500 |
| 2022 | $519 | $33,300 | $33,300 | $0 |
| 2020 | $522 | $33,300 | $33,300 | $0 |
| 2019 | $521 | $33,300 | $33,300 | $0 |
| 2018 | $1,035 | $33,300 | $33,300 | $0 |
| 2017 | $501 | $33,300 | $0 | $0 |
| 2016 | -- | $33,300 | $0 | $0 |
| 2015 | $1,136 | $33,300 | $0 | $0 |
| 2014 | $1,136 | $45,300 | $0 | $0 |
Source: Public Records
Agents Affiliated with this Home
-
Dan Foster
DF
Seller's Agent in 2026
Dan Foster
Long & Foster
(410) 310-3393
22 Total Sales
-
Kristina Hyland
Buyer's Agent in 2026
Kristina Hyland
Coldwell Banker Chesapeake Real Estate Company
(410) 725-9225
128 Total Sales
-
Kathleen Cassidy
Seller's Agent in 2023
Kathleen Cassidy
DRH Realty Capital, LLC.
(667) 500-2488
3,541 Total Sales
-
datacorrect BrightMLS
DB
Buyer's Agent in 2023
datacorrect BrightMLS
Non Subscribing Office
Map
Source: Bright MLS
MLS Number: MDKE2006586
APN: 04-338154
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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.
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Copyright 2026 Bright MLS, Inc.
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