Desirable end-unit, 3-story townhome located in the heart of Chestertown, just moments from downtown and adjacent to the new YMCA. This well-maintained home features newer carpet and paint, a one-year-old stove (purchased new for $4,000), and a hot water heater just two years old. A newer full-size stackable washer and dryer adds convenience. Enjoy both sunrise and sunset views with an east-facing front that fills the home with beautiful morning light and a west-facing rear offering stunning evening sunsets. The balcony has been recently stained, and the first-floor patio has been thoughtfully converted into a deck with built-in wood flower boxes—perfect for outdoor enjoyment. The versatile first level offers flexible space ideal for a bedroom, office, or exercise room, complete with a gas fireplace and sliding door access to the deck. The garage includes a built-in loft, workbench, and shelving for added storage and functionality. Upstairs, the primary suite features a vaulted ceiling and a spacious en-suite bath with soaking tub and walk-in shower. A mature maple tree enhances the backyard setting, providing charm and seasonal beauty. Move-in ready and ideally located—this home offers comfort, updates, and convenience all in one.
Sold for $295,000
Zestimate®
$295,000
107 Oak Leaf Dr, Chestertown, MD 21620
3beds
1,947sqft
Townhouse
Built in 2004
3,740 Square Feet Lot
$295,000 Zestimate®
$152/sqft
$2,271 Estimated rent
Home value
$295,000
Estimated sales range
Not available
$2,271/mo
Zestimate® history
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Gas fireplace
Zillow last checked:
Listing updated:
Listed by:
Kristina Hyland 410-725-9225,
Coldwell Banker Chesapeake Real Estate Company
Bought with:
Joseph Ciganek, 5005876
Coldwell Banker Chesapeake Real Estate Company
Source: Bright MLS,MLS#: MDKE2006114
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Basement
- Area: 0
Heating
- Heat Pump, Electric
Cooling
- Other, Electric
Appliances
- Included: Down Draft, Dishwasher, Dryer, Refrigerator, Stainless Steel Appliance(s), Washer, Water Heater, Electric Water Heater
Features
- Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Ceiling Fan(s), Combination Kitchen/Dining, Eat-in Kitchen, Kitchen Island, Kitchen - Table Space, Pantry, Primary Bath(s), Recessed Lighting, Cathedral Ceiling(s), Dry Wall, High Ceilings
- Flooring: Carpet, Ceramic Tile, Hardwood
- Has basement: No
- Number of fireplaces: 1
Interior area
- Total structure area: 1,947
- Total interior livable area: 1,947 sqft
- Finished area above ground: 1,947
- Finished area below ground: 0
Property
Parking
- Total spaces: 3
- Parking features: Storage, Built In, Garage Faces Front, Garage Door Opener, Inside Entrance, Oversized, Attached, Driveway
- Attached garage spaces: 1
- Uncovered spaces: 2
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Patio & porch: Deck
- Exterior features: Sidewalks, Street Lights, Other, Balcony
- Pool features: None
- Has view: Yes
- View description: Pond
- Has water view: Yes
- Water view: Pond
Lot
- Size: 3,740 Square Feet
- Features: Adjoins - Open Space, Corner Lot, Level, Corner Lot/Unit
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1504027442
- Zoning: R3/R4
- Special conditions: Standard
Construction
Type & style
- Home type: Townhouse
- Architectural style: Traditional
- Property subtype: Townhouse
Materials
- Brick, Concrete, Frame, Stick Built, Vinyl Siding
- Foundation: Slab
- Roof: Architectural Shingle
Condition
- Excellent
- New construction: No
- Year built: 2004
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Propane, Broadband
Community & HOA
Community
- Subdivision: Oak Hollow
HOA
- Has HOA: Yes
- HOA fee: $65 monthly
- HOA name: OAK HOLLOW
Location
- Region: Chestertown
- Municipality: Chestertown
Financial & listing details
- Price per square foot: $152/sqft
- Tax assessed value: $226,600
- Annual tax amount: $3,521
- Date on market: 2/27/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 3/31/2026 | Sold | $295,000$152/sqft |
Source:  Bright MLS #MDKE2006114 Report a problem | ||
| 3/8/2026 | Contingent | $295,000$152/sqft |
Source: Bright MLS #MDKE2006114 Report a problem | ||
| 2/27/2026 | Listed for sale | $295,000+25.5%$152/sqft |
Source: Bright MLS #MDKE2006114 Report a problem | ||
| 10/20/2021 | Sold | $235,000+37.5%$121/sqft |
Source: Bright MLS #MDKE2000198 Report a problem | ||
| 2/21/2012 | Sold | $170,857+3.6%$88/sqft |
Source: Public Record Report a problem | ||
| 11/3/2011 | Price change | $164,900-2.9%$85/sqft |
Source: foreclosure.com Report a problem | ||
| 10/2/2011 | Price change | $169,900-21.4%$87/sqft |
Source: foreclosure.com Report a problem | ||
| 9/21/2011 | Listed for sale | -- |
Source: foreclosure.com Report a problem | ||
| 4/30/2004 | Sold | $216,275$111/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $7,043 +113.7% | $224,700 +6.9% |
| 2024 | $3,295 +7.4% | $210,267 +7.4% |
| 2023 | $3,069 +8.6% | $195,833 +8% |
| 2022 | $2,825 +5.4% | $181,400 +6.1% |
| 2021 | $2,679 +6.5% | $170,933 +6.5% |
| 2020 | $2,515 +7.2% | $160,467 +7% |
| 2019 | $2,346 +0.6% | $150,000 |
| 2018 | $2,331 +3.3% | $150,000 |
| 2017 | $2,256 -14.2% | $150,000 -1.2% |
| 2016 | $2,629 | $151,800 |
| 2015 | $2,629 | $151,800 |
| 2014 | $2,629 | $151,800 -13.2% |
| 2013 | -- | $174,800 |
| 2012 | -- | $174,800 |
| 2011 | -- | $174,800 -39.1% |
| 2010 | -- | $287,060 +9.6% |
| 2009 | -- | $261,966 +10.6% |
| 2008 | -- | $236,873 +11.8% |
| 2007 | -- | $211,780 +4.5% |
| 2006 | -- | $202,636 +4.7% |
| 2005 | -- | $193,493 +4199.8% |
| 2004 | -- | $4,500 |
| 2003 | -- | $4,500 |
Find assessor info on the county website
Neighborhood: 21620
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Nearby schools
GreatSchools rating
- 7/10H. H. Garnett Elementary SchoolGrades: PK-5Distance: 1 mi
- 2/10Kent County Middle SchoolGrades: 6-8Distance: 0.8 mi
- 5/10Kent County High SchoolGrades: 9-12Distance: 4.2 mi
Schools provided by the listing agent
- District: Kent County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$295,000
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$295,000
- Maryland
- Kent County
- Chestertown
- 21620
- 107 Oak Leaf Dr
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