107 Flying Cloud Dr Chestertown, MD 21620
Estimated payment $2,595/month
Highlights
- Open Floorplan
- Partially Wooded Lot
- Porch
- Contemporary Architecture
- Stainless Steel Appliances
- Eat-In Kitchen
About This Home
NEW PRICE – Exceptional value for over 2,500 square feet of newer construction in the Village of Chestertown! A stunning 2023-built home with well-designed architectural elevations; two tone complimentary shades which beautifully compliment these unique features. The curb appeal captures your attention and the welcoming front porch invites you to slow down and relax.. your home! Step through the Craftsman style front door into a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,535 square feet of thoughtfully designed living space. The main level features an open-concept layout with a spacious family room, dining area, and bright, well-appointed kitchen — perfect for both everyday living and entertaining. A convenient first-floor laundry room and powder room add to the home’s functionality. The kitchen is designed with today’s lifestyle in mind, featuring stainless steel appliances, a generous peninsula for gathering, and a large corner pantry providing abundant storage. Upstairs, the owner’s suite offers a peaceful retreat with a spacious walk-in closet and private en-suite bath complete with double vanity and walk-in shower. Three additional bedrooms share a full hall bath with double vanity, providing comfort and convenience for family or guests. The third level expands the home’s versatility with a fifth bedroom, full bath, and flexible bonus space ideal for a home office, playroom, media room, or fitness area! Ample closets throughout ensure exceptional storage options. Extras you’ll love: a modern Smart Home Package offering convenience, efficiency, and peace of mind. Thoughtfully positioned against a backdrop of mature trees rather than neighboring homes, this property offers a more private outdoor experience. Seller is offering a buyer credit toward allowable closing costs — an excellent opportunity to conserve cash for personalized backyard improvements such as fencing, shed or patio after settlement! This beautifully landscaped community common area features a scenic pond with fountain, creating a welcoming neighborhood setting. Located just minutes from downtown Chestertown — known for its charming shops, restaurants, parks, waterfront atmosphere, and Washington College — you’ll enjoy easy access to date nights, community events, and small-town charm at its best. This thoughtfully planned community is complete, offering a wonderful opportunity to become part of an established neighborhood. Don’t miss your chance to make this exceptional home your own!
Listing Agent
(410) 266-9005 alicia.jenkins@c21nm.com CENTURY 21 New Millennium Brokerage Phone: 4102669005 License #648469 Listed on: 05/16/2026
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
Map
Home Values in the Area
Average Home Value in this Area
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 |
|---|---|---|---|---|
| 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 |
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 |
|---|---|---|---|---|---|
| 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 |
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 |
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: Bright MLS
MLS Number: MDKE2006510
APN: 04-338278
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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.
Property information displayed is deemed reliable but is not guaranteed.
Copyright 2026 Bright MLS, Inc.
- 104 Flying Cloud Dr
- 102 Flying Cloud Dr
- 214 Silver Heel Rd
- 104 Conley Dr
- 103 Metcalf Rd
- 104 Acorn Dr
- 3 Haacke Dr
- 304 Hadaway Dr
- 2 Scheeler Rd
- 108 Pine St
- 956 Washington Ave
- 213 Byford Dr
- 1014 Twin Ct
- 222 Mount Vernon Ave
- 144 Prospect St
- 110 Prospect St
- 231 Richard Dr
- 139 Prospect St
- 100 Prospect St
- 234 N College Ave
- 102 Metcalf Rd
- 104 Cedar St
- 1010 Twin Ct
- 222 Mount Vernon Ave
- 101 Morgnec Rd
- 103 S Lynchburg St
- 128 N Queen St Unit 3
- 104 Maple Ave Unit 6
- 7501 Church Hill Rd Unit 5
- 7019 Church Hill Rd Unit B
- 27318 Morgnec Rd Unit 27318 Unit B
- 24731 Langford Rd Unit B
- 21324 Delaware Ave
- 13755 Shallcross Wharf Rd
- 722 Church Hill Rd
- 226 Phelps Ave
- 108 Little Kidwell Ave Unit B
- 212 Frederick Dr
- 25 2nd Ave
- 215 Thompson Ave
Ask me questions while you tour the home.