104 Oak Leaf Dr, Chestertown, MD 21620
Property image
Property image
OFF MARKET

104 Oak Leaf Dr
Chestertown, MD 21620

  • 3 Beds
  • 3.5 Baths
  • 1,840 sqft

$286,400

Trulia Estimate
as of Aug 5, 2026
Est. Refi. Payment $1,738/mo*
Refinance Your Home

$286,400

Trulia Estimate
as of Aug 5, 2026
Est. Refi. Payment $1,738/mo*
Refinance Your Home
3 Beds
3.5 Baths
1,840 sqft

Local Information

  • Map ViewExplore the area around 104 Oak Leaf Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Townhouse
Year Built
2003
Living Area
1,840 sqft
Price/Sqft
$156
Parking
1 Car Garage
HOA
$55/Monthly

About this House

Welcome to your new home in the vibrant community of Chestertown! This beautiful 3-bedroom, 3.5-bath townhome features an open layout perfect for modern living. The heart of the home is the stylish kitchen, equipped with contemporary finishes and ample storage. Enjoy relaxing in the spacious living area or step outside to your private deck—ideal for entertaining or soaking up the sun. The attached garage offers convenience and additional storage. Located just minutes from the new YMCA and other local amenities, this home is perfect for those seeking an active lifestyle. Plus, with solar panels installed, you'll enjoy energy efficiency and lower utility bills. Don't miss this opportunity to own a piece of Chestertown’s growing charm! Schedule your tour today!
104 Oak Leaf Dr, Chestertown, MD 21620 is a 3 bedroom, 4 bathroom, 1,840 sqft townhouse built in 2003. It last sold for $283,000 on Feb 19, 2025 (2% below the $289,000 asking price). More recently, it was listed as a rental in September 2024 with an asking price of $3,000 per month. That rental listing was removed on October 1, 2024. It is currently off market. The Trulia Estimate is $286,400, with a rent estimate of $2,278/month.

Home Details for 104 Oak Leaf Dr

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1840 Square Feet
Appliances & Utilities
Appliances: Electric Water Heater
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
No Fireplace
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: None
View
No View

Exterior Features

Exterior Home Features
Other Structures: Above Grade, Below GradeFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 1Parking: Garage Faces Front,Attached,Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1840 Square Feet

Property Information

Year Built
Year Built: 2003
Property Type / Style
Property Type: ResidentialProperty Subtype: TownhouseStructure Type: Interior Row/TownhouseArchitecture: Colonial
Building
Construction Materials: Brick, Aluminum SidingNot a New Construction
Property Information
Parcel Number: 1504027752

Price & Status

Price
List Price: $289,000
Status Change & Dates
Off Market Date: Wed Feb 19 2025Possession Timing: Immediate

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: CHESTERTOWNCommunity: Oak Hollow
School Information
Elementary School District: Kent County Public SchoolsJr High / Middle School District: Kent County Public SchoolsHigh School District: Kent County Public Schools

Building

Building Area
Building Area: 1840 Square Feet

Community

Not Senior Community

HOA

Has an HOAHOA Fee: $55/Monthly

Lot Information

Lot Area: 2160 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Agency

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDKE2004584Municipality: ChestertownAbove Grade Unfinished Area: 1840
Last check for updates: about 1 hour ago
Listed by Krystal Zellner, (443) 877-9565
Crown Homes Real Estate
Bought with: Jordan Larigan, (215) 801-1939, VYBE Realty
Source: Bright MLS, MLS#MDKE2004584

Price History for 104 Oak Leaf Dr

DatePriceEventSource
02/19/2025$283,000Sold
Bright MLS #MDKE2004584
12/03/2024$289,000PendingBright MLS #MDKE2004584
11/07/2024$289,000PriceChange
Bright MLS #MDKE2004584
10/26/2024$295,000Listed For SaleBright MLS #MDKE2004584
10/01/2024$3,000ListingRemovedZillow Rentals
09/28/2024$3,000Listed For RentZillow Rentals
06/16/2023$272,500Sold
Bright MLS #MDKE2002560
05/18/2023$259,900PendingBright MLS #MDKE2002560
05/12/2023$259,900Listed For SaleBright MLS #MDKE2002560
03/15/2023ListingRemovedZillow Rentals
02/04/2023$2,250Listed For RentZillow Rentals
05/28/2021ListingRemovedZillow Rental Manager
05/25/2021$2,250Listed For RentZillow Rental Manager
02/26/2021ListingRemovedN/A
07/15/2020$2,250ListingRemovedN/A
07/08/2020$2,250Listed For RentN/A
08/26/2018$179,000ListingRemovedAgent Provided
08/20/2018$179,000PendingAgent Provided
08/09/2018$179,000Listed For SaleAgent Provided
07/01/2018$179,000ListingRemovedAgent Provided
05/25/2018$179,000Listed For SaleAgent Provided
01/16/2004$179,900Sold
N/A

Market trends in Chestertown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
5MoM
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Property Tax and Assessment

Year2025
Tax$6,065
Assessment$193,500
Home facts updated by county records

Comparable Sales for 104 Oak Leaf Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
107 Oak Leaf Dr, Chestertown, MD
0.03
Townhouse
$295,000
03/31/26
3
2.5
1,947
108 Oak Leaf Dr, Chestertown, MD
0.01
Townhouse
$296,500
05/22/26
2
2.5
1,867
115 Acorn Dr, Chestertown, MD
0.05
Townhouse
$290,000
06/04/26
2
2.5
1,864
107 Metcalf Rd, Chestertown, MD
0.15
Townhouse
$259,900
05/18/26
3
1.5
1,200
112 Metcalf Rd, Chestertown, MD
0.11
Townhouse
$250,000
04/10/26
3
1.5
1,280
109 Metcalf Rd, Chestertown, MD
0.14
Townhouse
$264,900
05/26/26
3
1.5
1,280
101 Metcalf Rd, Chestertown, MD
0.14
Townhouse
$264,900
12/05/25
3
1.5
1,280
100 Metcalf Rd, Chestertown, MD
0.13
Townhouse
$240,000
01/16/26
3
2
1,140
107 Conley Dr, Chestertown, MD
0.11
Townhouse
$150,000
05/15/26
3
1
1,140
423 Calvert St, Chestertown, MD
1.03
Townhouse
$190,000
06/26/26
3
1.5
1,136

Nearby homes

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Assigned Schools

These are the assigned schools for 104 Oak Leaf Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Chestertown

At least 34 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 84 % Say there's holiday spirit

  • 83 % Say it's dog friendly

  • 77 % Say people would walk alone at night

  • 77 % Say parking is easy

  • 76 % Say yards are well-kept

  • 74 % Say it's quiet

  • 61 % Say neighbors are friendly

  • 57 % Say there's wildlife

  • 56 % Say it's walkable to restaurants

  • 54 % Say there are sidewalks

  • 49 % Say kids play outside

  • 46 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

  • 41 % Say there are community events

  • 38 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
    1
    Flag
  • Trulia User
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
    1
    Flag
  • Trulia User
    "I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
    0
    Flag
  • Kesha C.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
    0
    Flag
  • Tracy W.
    "The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
    0
    Flag
  • Rancraw
    "This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
    9
    Flag
  • Acaldwell1297
    "I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
    1
    Flag
  • Guillermo A.
    "Good Community, friendly people, good services. "
    0
    Flag
  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
    5
    Flag
  • asso
    "Quiet - not for night owls. Nice farmer's market, good library. Easy acess for weekends in DC, Baltimore, Philly, & Ocean Beaches. College town, Chester River"
    0
    Flag
  • Dafoster
    "Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
    5
    Flag

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Apartments for Rent

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Homes for sale near 104 Oak Leaf Dr

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Off Market Homes Near 104 Oak Leaf Dr

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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. Click here for more information