107 Flying Cloud Dr Chestertown, MD 21620
Chestertown AreaEstimated payment $2,578/month
Highlights
- Open Floorplan
- Partially Wooded Lot
- Porch
- Contemporary Architecture
- Stainless Steel Appliances
- Eat-In Kitchen
About This Home
NEW 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.
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 |
|---|---|---|---|---|---|
| 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 |
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
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