This beautifully maintained end-unit townhome, owned by its original owner, has been meticulously cared for and is now ready for its next chapter. The end-unit location provides additional natural light, creating a bright and inviting atmosphere throughout. The home has been freshly painted and features brand-new carpeting, while the ceramic tile and hardwood flooring in other areas are in excellent condition. The kitchen is equipped with a full set of newer appliances, offering both style and reliability, and the home also includes a newer washer and dryer—giving you the convenience of updated, move-in ready essentials from day one. Major systems have already been taken care of, including a new heating and cooling system (inside and out), a new hot water heater, and a newer roof and shutters. A flexible bonus room on the ground level currently houses the washer and dryer and can easily serve as a home office, TV room, or additional living space—whatever suits your needs. There is also an additional washer and dryer hookup on the upper level if preferred. Step out from the kitchen onto a private balcony, perfect for relaxing or entertaining. Truly move-in ready, this home offers a clean slate to make your own, along with the peace of mind that comes from years of thoughtful maintenance—making it feel like the perfect townhome.
Sold for $296,500
$296,500
108 Oak Leaf Dr, Chestertown, MD 21620
2beds
1,867sqft
Townhouse
Built in 2004
3,672 Square Feet Lot
$297,600 Zestimate®
$159/sqft
$2,186 Estimated rent
Home value
$297,600
Estimated sales range
Not available
$2,186/mo
Zestimate® history
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$1,551/mo
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List your homeWhat's special
Newer washer and dryerFreshly paintedNewer roof and shuttersBright and inviting atmosphereBrand-new carpeting
Zillow last checked:
Listing updated:
Listed by:
Grace Crockett 410-708-5615,
Doug Ashley Realtors, LLC
Bought with:
Maryn LeClair, RS-0036518
Chesapeake Real Estate Associates, LLC
Source: Bright MLS,MLS#: MDKE2006224
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Rooms
- Room types: Living Room, Kitchen, Other, Bonus Room
Bonus room
- Level: Lower
Kitchen
- Features: Cathedral/Vaulted Ceiling, Granite Counters, Balcony Access, Dining Area, Flooring - Ceramic Tile, Kitchen Island, Kitchen - Electric Cooking, Lighting - Ceiling, Lighting - Pendants, Pantry
- Level: Main
Living room
- Features: Flooring - HardWood
- Level: Main
Other
- Level: Lower
Heating
- Heat Pump, Electric
Cooling
- Ceiling Fan(s), Heat Pump, Electric
Appliances
- Included: Cooktop, Dishwasher, Dryer, Ice Maker, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer, Water Heater, Electric Water Heater
Features
- Bathroom - Stall Shower, Bathroom - Tub Shower, Ceiling Fan(s), Combination Kitchen/Dining, Crown Molding, Curved Staircase, Eat-in Kitchen, Kitchen - Table Space, Pantry, Upgraded Countertops, Other
- Flooring: Carpet, Ceramic Tile, Hardwood
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 1,867
- Total interior livable area: 1,867 sqft
- Finished area above ground: 1,867
- Finished area below ground: 0
Property
Parking
- Total spaces: 3
- Parking features: Oversized, Garage Faces Front, Garage Door Opener, Inside Entrance, Storage, Other, Concrete, 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, Lighting
- Pool features: None
Lot
- Size: 3,672 Square Feet
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1504027736
- Zoning: R3/R4
- Special conditions: Standard
Construction
Type & style
- Home type: Townhouse
- Architectural style: Traditional
- Property subtype: Townhouse
Materials
- Brick, Block, Concrete, Vinyl Siding, Stick Built, Blown-In Insulation
- Foundation: Block
- Roof: Architectural Shingle
Condition
- Excellent
- New construction: No
- Year built: 2004
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Security: Fire Sprinkler System
- Subdivision: Oak Hollow
HOA
- Has HOA: Yes
- HOA fee: $65 monthly
Location
- Region: Chestertown
- Municipality: Chestertown
Financial & listing details
- Price per square foot: $159/sqft
- Tax assessed value: $211,100
- Annual tax amount: $3,282
- Date on market: 4/16/2026
- Listing agreement: Exclusive Agency
- Listing terms: Cash,Conventional,FHA,USDA Loan,VA Loan
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 5/22/2026 | Sold | $296,500-1%$159/sqft |
Source:  Bright MLS #MDKE2006224 Report a problem | ||
| 5/4/2026 | Pending sale | $299,500$160/sqft |
Source: Bright MLS #MDKE2006224 Report a problem | ||
| 4/16/2026 | Listed for sale | $299,500+39.1%$160/sqft |
Source: Bright MLS #MDKE2006224 Report a problem | ||
| 3/3/2004 | Sold | $215,389$115/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $6,253 +100.2% | $209,400 +5.1% |
| 2024 | $3,123 +5.3% | $199,300 +5.3% |
| 2023 | $2,965 +6.3% | $189,200 +5.6% |
| 2022 | $2,789 +5.4% | $179,100 +6.1% |
| 2021 | $2,646 +6.5% | $168,833 +6.5% |
| 2020 | $2,485 +7.1% | $158,567 +6.9% |
| 2019 | $2,319 +0.6% | $148,300 |
| 2018 | $2,305 +3.3% | $148,300 |
| 2017 | $2,230 -14.2% | $148,300 -1.2% |
| 2016 | $2,600 | $150,100 |
| 2015 | $2,600 | $150,100 |
| 2014 | $2,600 | $150,100 -13.2% |
| 2013 | -- | $172,900 |
| 2012 | -- | $172,900 |
| 2011 | -- | $172,900 -39% |
| 2010 | -- | $283,440 +9.6% |
| 2009 | -- | $258,650 +10.6% |
| 2008 | -- | $233,860 +11.9% |
| 2007 | -- | $209,070 +4.6% |
| 2006 | -- | $199,950 +4.8% |
| 2005 | -- | $190,830 +4140.7% |
| 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
$297,600
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
$297,600
- Maryland
- Kent County
- Chestertown
- 21620
- 108 Oak Leaf Dr
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