Cindy Genther
Rock Hall Properties Real Estate
(667) 244-8305
135 Total Sales
7 in Chestertown
$178K - $700K Price Range
107 Flying Cloud Dr Chestertown, MD 21620
Chestertown Area
5
Beds
3.5
Baths
2,534
Sq Ft
4,969
Sq Ft Lot
Highlights
- Open Floorplan
- Partially Wooded Lot
- Porch
- Contemporary Architecture
- Stainless Steel Appliances
- Eat-In Kitchen
About This Home
As of August 2026NEW PRICE – One of Chestertown's Best Values! Over 2,500 square feet of 2023 construction priced comparably to many older Chestertown homes with just 1,200–1,800 square feet. If you're looking for maximum living space, modern design, and exceptional value, this home deserves a closer look.
This move-in ready, three-story home offers 5 bedrooms, 3.5 baths, and 2,535 square feet of thoughtfully designed living space. The inviting front porch welcomes you into an open-concept main level featuring a spacious family room, dining area, and a bright kitchen designed for everyday living and entertaining. Highlights include stainless steel appliances, a generous peninsula, large corner pantry, first-floor laundry, and convenient powder room.
The private owner's suite features a spacious walk-in closet and en-suite bath with double vanity and walk-in shower. Three additional bedrooms share a full bath with double vanity, while the finished third level provides a fifth bedroom, full bath, and flexible bonus space perfect for a home office, media room, playroom, fitness area, or guest suite. Ample closet space throughout provides exceptional storage.
Unlike many homes in the community, this property backs to mature trees rather than neighboring homes, offering a more private backyard setting.
Additional features include a modern Smart Home Package for convenience, efficiency, and peace of mind.
Seller is offering a buyer credit toward allowable closing costs, helping conserve cash after settlement for future backyard enhancements such as a patio, fencing, or shed.
Enjoy the beautifully landscaped community pond with fountain and the convenience of being just minutes from historic downtown Chestertown, Washington College, waterfront parks, restaurants, shopping, and year-round community events.
The Village of Chestertown is now a completed community with no future construction—offering the opportunity to enjoy an established neighborhood from day one. Compare the square footage, age, and features, then come see why this home represents one of the best values currently available in the Chestertown market.
Last Agent to Sell the Property
(410) 266-9005 alicia.jenkins@c21nm.com CENTURY 21 New Millennium Brokerage Phone: 4102669005 License #648469 Listed on: 05/16/2026
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Home Details
Home Type
- Single Family
Est. Annual Taxes
- $5,390
Year Built
- Built in 2023
Lot Details
- 4,969 Sq Ft Lot
- Southwest Facing Home
- Landscaped
- Interior Lot
- Partially Wooded Lot
- Backs to Trees or Woods
- Front Yard
- Property is in excellent condition
- Property is zoned R3/R4
HOA Fees
- $70 Monthly HOA Fees
Home Design
- Contemporary Architecture
- Slab Foundation
- Blown-In Insulation
- Batts Insulation
- Architectural Shingle Roof
- Vinyl Siding
- Stick Built Home
Interior Spaces
- 2,534 Sq Ft Home
- Property has 3 Levels
- Open Floorplan
- Recessed Lighting
- Window Treatments
- Combination Dining and Living Room
Kitchen
- Eat-In Kitchen
- Electric Oven or Range
- Microwave
- Dishwasher
- Stainless Steel Appliances
- Disposal
Flooring
- Carpet
- Luxury Vinyl Plank Tile
Bedrooms and Bathrooms
- 5 Main Level Bedrooms
- En-Suite Bathroom
- Walk-In Closet
- Bathtub with Shower
- Walk-in Shower
Laundry
- Laundry Room
- Laundry on main level
- Dryer
- Washer
Home Security
- Home Security System
- Fire and Smoke Detector
- Fire Sprinkler System
Parking
- 2 Parking Spaces
- 2 Driveway Spaces
- On-Street Parking
Schools
- H. H. Garnett Elementary School
- Kent County Middle School
- Kent County High School
Utilities
- 90% Forced Air Heating and Cooling System
- Programmable Thermostat
- 200+ Amp Service
- Electric Water Heater
- Phone Available
- Cable TV Available
Additional Features
- More Than Two Accessible Exits
- Energy-Efficient Appliances
- Porch
Listing and Financial Details
- Tax Lot 38
- Assessor Parcel Number 1504338278
Community Details
Overview
- $180 Capital Contribution Fee
- Association fees include common area maintenance, lawn maintenance, road maintenance
- Village At Chestertown HOA
- Built by D.R. Horton
- The Village At Chestertown Subdivision, Verona Floorplan
- Property Manager
Amenities
- Common Area
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 16, 2026
Closed on
Aug 19, 2026
Sold by
Jennifer Quagraine and Joseph Quagraine
Bought by
Seller's Agent
Cynthia Gardner
CENTURY 21 New Millennium
Buyer's Agent
Sharon Fisher
Coldwell Banker Realty
List Price
$395,000
Sold Price
$380,000
Premium/Discount to List
-$15,000
-3.8%
Views
178
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
35.93%
Original Mortgage
$368,600
Outstanding Balance
$368,600
Interest Rate
6.49%
Mortgage Type
New Conventional
Estimated Equity
$20,847
Purchase Details
Listed on
Jun 1, 2023
Closed on
Aug 29, 2023
Sold by
D R Horton Inc
Bought by
Quagraine Joseph and Quagraine Jennifer
Seller's Agent
Kathleen Cassidy
D R Horton Realty of Virginia LLC
Buyer's Agent
Cynthia Gardner
CENTURY 21 New Millennium
List Price
$385,945
Sold Price
$344,990
Premium/Discount to List
-$40,955
-10.61%
Views
129
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
3.31%
Original Mortgage
$244,990
Interest Rate
6.81%
Mortgage Type
New Conventional
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
-
Cindy Genther
-
Kristina Hyland
Kristina Hyland
Coldwell Banker Chesapeake Real Estate Company
(667) 243-9976
129 Total Sales
18 in Chestertown
$110K - $700K Price Range
-
Julie Strickler
Julie Strickler
Remax Vision
(484) 878-4460
109 Total Sales
1 in Chestertown
$475,000 Price
-
Edwina Rogers
Edwina Rogers
Brysis Realty International
(443) 565-4921
71 Total Sales
1 in Chestertown
$379,000 Price
-
Dustin Oldfather
Dustin Oldfather
Compass
(302) 393-2276
1,393 Total Sales
1 in Chestertown
$585,000 Price
-
Kara Leddy
Kara Leddy
Coldwell Banker Realty
(443) 494-8169
62 Total Sales
1 in Chestertown
$328,000 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 | $344,990 | Dhi Title Agency | |
| 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 | $244,990 | New Conventional |
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 |
|---|---|---|---|---|---|
| 08/18/2026 08/18/26 | Sold | $380,000 | +1.3% | $150 / Sq Ft | |
| 07/06/2026 07/06/26 | Price Changed | $375,000 | -2.6% | $148 / Sq Ft | |
| 06/09/2026 06/09/26 | Price Changed | $385,000 | -2.5% | $152 / Sq Ft | |
| 05/16/2026 05/16/26 | For Sale | $395,000 | +14.5% | $156 / Sq Ft | |
| 08/29/2023 08/29/23 | Sold | $344,990 | 0.0% | $150 / Sq Ft | View Prior Sale |
| 07/15/2023 07/15/23 | Pending | -- | -- | -- | |
| 07/07/2023 07/07/23 | Price Changed | $344,990 | -1.4% | $150 / Sq Ft | |
| 07/05/2023 07/05/23 | Price Changed | $349,990 | -9.3% | $152 / Sq Ft | |
| 06/01/2023 06/01/23 | For Sale | $385,945 | -- | $168 / 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 | $5,169 | $329,800 | $80,400 | $249,400 |
| 2025 | $5,390 | $343,900 | $80,400 | $263,500 |
| 2024 | $5,390 | $343,900 | $80,400 | $263,500 |
| 2023 | $5,390 | $343,900 | $80,400 | $263,500 |
| 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
-
Cynthia Gardner
Seller's Agent in 2026
Cynthia Gardner
Century 21 New Millennium
(410) 703-9202
42 Total Sales
-
Sharon Fisher
Buyer's Agent in 2026
Sharon Fisher
Coldwell Banker Realty
(443) 375-0689
65 Total Sales
-
Kathleen Cassidy
Seller's Agent in 2023
Kathleen Cassidy
DRH Realty Capital, LLC.
(667) 500-2488
3,523 Total Sales
Map
Source: Bright MLS
MLS Number: MDKE2006510
APN: 04-338278
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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.
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Copyright 2026 Bright MLS, Inc.
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