Skip main navigation
For sale
    • $649,000

    22400 Great Oak Landing Rd, Chestertown, MD 21620

    4beds
    2,864sqft
    : 
    $4,260/mo
    Get pre-qualified
    Single Family Residence
    Built in 2000
    1.03 Acres Lot
    $637,100 Zestimate®
    $227/sqft
    $8/mo HOA

    What's special

    Cozy propane fireplaceWalk-in closetBuilt-in cherry cabinetsSoaring two-story foyerPlantation shuttersFormal dining roomBrand-new refrigerator
    Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry cabinetry and a brand-new refrigerator. Hardwood floors run throughout the main living areas, while brand-new carpeting softens every bedroom. On the main level, the primary suite includes its own bathroom, a walk-in closet, and plantation shutters. A second main-floor bedroom (ideal as a guest room or home office) shares convenient access to the hall bath. Completing the first floor are a large walk-in pantry and a laundry room outfitted with a brand-new washer and dryer. Upstairs you’ll find two additional spacious bedrooms, each with its own walk-in closet, plus a full bathroom. An oversized walk-in attic provides abundant storage or the perfect opportunity to create a bonus room or extra living space. Dual zone HVAC provides comfort from a newer lower level unit and an upper unit replaced in 2026. Complete roof replacement was completed in 2026 as well. A voluntary HOA opens the door to the amenities of Safe Harbor Great Oak Landing Marina—private beach area, pool, 9-hole golf course, and more. Simply walk or hop in a golf cart to reach the marina and enjoy all the water-oriented lifestyle this community has to offer. You’re also minutes from Rock Hall, with its additional marinas, charter boats, shopping, and restaurants. Less than 10 minutes away lies Chestertown and Washington College, along with more shopping, dining options, a hospital, and a wonderful Saturday morning Farmers Market, and much more. Whether you’re seeking a full-time residence or a relaxing Eastern Shore getaway, this home delivers quality craftsmanship, flexible living spaces, and convenient access to the best of Great Oak Estates and the surrounding area.
    3 days
    |
    239
    |
    5
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Terri Kulp 301-462-9976,

    Coldwell Banker Chesapeake Real Estate Company 410-778-0330

    Source: Bright MLS,MLS#: MDKE2006946MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 3
      • Main level bathrooms: 2
      • Main level bedrooms: 2
      Rooms
      • Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Foyer, Breakfast Room, Laundry, Bathroom 3, Attic, Primary Bathroom
      Primary bedroom
      • Features: Flooring - Carpet, Walk-In Closet(s), Ceiling Fan(s), Window Treatments
      • Level: Main
      • Area: 255 Square Feet
      • Dimensions: 15 X 17
      Bedroom 2
      • Features: Flooring - Carpet, Ceiling Fan(s)
      • Level: Main
      • Area: 168 Square Feet
      • Dimensions: 12 X 14
      Bedroom 3
      • Features: Flooring - Carpet, Walk-In Closet(s), Ceiling Fan(s)
      • Level: Upper
      • Area: 255 Square Feet
      • Dimensions: 15 X 17
      Bedroom 4
      • Features: Flooring - Carpet, Walk-In Closet(s), Ceiling Fan(s)
      • Level: Upper
      • Area: 210 Square Feet
      • Dimensions: 14 X 15
      Primary bathroom
      • Level: Main
      Bathroom 3
      • Level: Upper
      Other
      • Features: Attic - Floored
      • Level: Upper
      Breakfast room
      • Features: Flooring - HardWood, Built-in Features, Recessed Lighting
      • Level: Main
      • Area: 126 Square Feet
      • Dimensions: 9 X 14
      Dining room
      • Features: Flooring - HardWood, Recessed Lighting, Window Treatments
      • Level: Main
      • Area: 195 Square Feet
      • Dimensions: 13 X 15
      Family room
      • Features: Flooring - HardWood, Fireplace - Gas, Built-in Features
      • Level: Main
      • Area: 224 Square Feet
      • Dimensions: 14 X 16
      Foyer
      • Features: Flooring - HardWood
      • Level: Main
      Kitchen
      • Features: Flooring - HardWood, Recessed Lighting, Countertop(s) - Solid Surface, Double Sink, Kitchen - Gas Cooking
      • Level: Main
      • Area: 168 Square Feet
      • Dimensions: 12 X 14
      Laundry
      • Features: Flooring - Ceramic Tile, Pantry
      • Level: Main
      • Area: 96 Square Feet
      • Dimensions: 8 X 12
      Living room
      • Features: Flooring - Solid Hardwood, Recessed Lighting, Window Treatments
      • Level: Main
      Heating
      • Forced Air, Electric, Propane
      Cooling
      • Central Air, Electric
      Appliances
      • Included: Microwave, Dishwasher, Disposal, Dryer, Exhaust Fan, Extra Refrigerator/Freezer, Oven/Range - Gas, Refrigerator, Stainless Steel Appliance(s), Cooktop, Washer, Water Conditioner - Owned, Water Heater, Water Treat System, Electric Water Heater
      • Laundry: Main Level, Laundry Room
      Features
      • Breakfast Area, Floor Plan - Traditional, Attic, Built-in Features, Ceiling Fan(s), Entry Level Bedroom, Formal/Separate Dining Room, Eat-in Kitchen, Pantry, Primary Bath(s), Recessed Lighting, Walk-In Closet(s), Dry Wall
      • Flooring: Hardwood, Carpet, Ceramic Tile, Wood
      • Doors: Sliding Glass, ENERGY STAR Qualified Doors
      • Windows: Bay/Bow, ENERGY STAR Qualified Windows, Window Treatments
      • Has basement: No
      • Number of fireplaces: 1
      • Fireplace features: Screen, Gas/Propane
      Interior area
      • Total structure area: 3,464
      • Total interior livable area: 2,864 sqft
      • Finished area above ground: 2,864
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 8
      • Parking features: Garage Door Opener, Garage Faces Side, Built In, Inside Entrance, Gravel, Driveway, Attached
      • Attached garage spaces: 2
      • Uncovered spaces: 6
      • Details: Garage Sqft: 600
      Accessibility
      • Accessibility features: Accessible Approach with Ramp
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Patio
      • Exterior features: Private Beach
      • Pool features: None
      • Has view: Yes
      • View description: Garden, Pasture, Trees/Woods
      • Waterfront features: Swimming Allowed, Boat - Powered, Canoe/Kayak, Fishing Allowed
      • Body of water: Fairlee Creek
      Lot
      • Size: 1.03 Acres
      • Features: Backs to Trees, Front Yard, Landscaped, Wooded, Suburban
      Details
      • Additional structures: Above Grade, Below Grade
      • Parcel number: 1506025099
      • Zoning: RR
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Traditional
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Crawl Space
      • Roof: Architectural Shingle
      Condition
      • New construction: No
      • Year built: 2000
      • Major remodel year: 2026

      Utilities & green energy

      • Electric: 200+ Amp Service
      • Sewer: Private Septic Tank
      • Water: Well
      • Utilities for property: Cable Connected, Propane

      Community & HOA

      Community
      • Subdivision: Great Oak Estates
      HOA
      • Has HOA: Yes
      • Amenities included: Pool, Golf Course, Marina/Marina Club
      • HOA fee: $100 annually
      • HOA name: GERAT OAK COMMUNITY ASSOCIATION
      Location
      • Region: Chestertown

      Financial & listing details

      • Price per square foot: $227/sqft
      • Tax assessed value: $469,467
      • Annual tax amount: $4,695
      • Date on market: 8/23/2026
      • Listing agreement: Exclusive Right To Sell
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Road surface type: Black Top

        Estimated market value

        $637,100

        $605,000 - $669,000

        $3,098/mo

        Price history

        DateEventPrice
        8/23/2026Listed for sale$649,000+18.2%$227/sqft
        Source: Bright MLS #MDKE2006946 Report a problem
        12/9/2022Sold$549,000$192/sqft
        Source: Bright MLS #MDKE2002054 Report a problem
        11/3/2022Contingent$549,000$192/sqft
        Source: Bright MLS #MDKE2002054 Report a problem
        11/2/2022Listed for sale$549,000+86.7%$192/sqft
        Source: Bright MLS #MDKE2002054 Report a problem
        7/7/2018Sold$294,000-2%$103/sqft
        Source: Public Record Report a problem
        5/26/2018Pending sale$299,900$105/sqft
        Source: Doug Ashley Realtors, LLC #1003980585 Report a problem
        5/9/2018Price change$299,900-6%$105/sqft
        Source: Doug Ashley Realtors, LLC #1003980585 Report a problem
        4/6/2018Price change$319,000-2.7%$111/sqft
        Source: Doug Ashley Realtors, Llc #1003980585 Report a problem
        12/7/2017Price change$327,900-0.3%$114/sqft
        Source: Doug Ashley Realtors, Llc #1003980585 Report a problem
        10/18/2017Price change$329,000-2.9%$115/sqft
        Source: Cross Street Realtors LLC #KE9918474 Report a problem
        9/16/2017Listed for sale$339,000$118/sqft
        Source: Cross Street Realtors LLC #KE9918474 Report a problem
        7/10/2017Pending sale$339,000$118/sqft
        Source: Cross Street Realtors LLC #KE9918474 Report a problem
        6/8/2017Price change$339,000-2.9%$118/sqft
        Source: Cross Street Realtors LLC #KE9918474 Report a problem
        4/17/2017Price change$349,000-5.7%$122/sqft
        Source: Cross Street Realtors LLC #KE9918474 Report a problem
        3/3/2017Price change$369,900-1.4%$129/sqft
        Source: Rock Hall Properties Real Estate #KE9624527 Report a problem
        8/31/2016Price change$375,000-1.1%$131/sqft
        Source: Rock Hall Properties Real Estate #KE9624527 Report a problem
        7/20/2016Price change$379,000-2.6%$132/sqft
        Source: Rock Hall Properties Real Estate #KE9624527 Report a problem
        4/12/2016Listed for sale$389,000+980.6%$136/sqft
        Source: Rock Hall Properties Real Estate #KE9624527 Report a problem
        9/23/1996Sold$36,000$13/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$9,510 +133.9%$414,033 +15.5%
        2024$4,067 +0.9%$358,600 +0.9%
        2023$4,030 +1.8%$355,400 -0.9%
        2022$3,959 +0%$358,600 +2.8%
        2021$3,958 $349,000
        2020$3,958 $349,000
        2019$3,958 -1.7%$349,000 -1.7%
        2018$4,028 $355,200
        2017$4,028 -11.1%$355,200
        2016$4,531 $355,200 -1.2%
        2015$4,531 $359,600
        2014$4,531 $359,600
        2013-- $359,600 -16.8%
        2012-- $432,300
        2011-- $432,300
        2010-- $432,300 -10.2%
        2009-- $481,570 +13.7%
        2008-- $423,700 +15.8%
        2007-- $365,830 +18.8%
        2006-- $307,960 +3.4%
        2005-- $297,976 +3.5%
        2004-- $287,993 +3.6%
        2003-- $278,010 +4%
        2002-- $267,302 +4.2%
        2001-- $256,596
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        See how much you could borrow to make a competitive offer.
        Get pre-qualified

        Climate risks

        Neighborhood: 21620

        Getting around

        9 / 100
        Car-Dependent
        35 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • High: Kent County
        • 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.

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes

              Nearby cities

              Nearby neighborhoods

              Nearby zip codes

              Other Chestertown Topics

                Search
                Updates
                Favorites
                Plan
                Inbox