$649,000
 $3,484 est/mo Sourced by Back At You

22400 Great Oak Landing Rd.,CHESTERTOWN, MD 21620

CHESTERTOWN, MD 21620

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Description

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.

Details

MLS #MDKE2006946
Listing TypeFor Sale
StyleHouse
HOA Dues$100
Sub-TypeResale
StatusActive-bright
Year2000
Days On Site22
Listing Provided ByColdwell Banker Chesapeake Real Estate Company | Terri L Kulp

Features

Bed(s)4
Bath(s) 3 Total
SQ Feet2,864
Garage2
Story(s)2
ZoningRR
Acreage1.03
Property ViewGarden, Lawn, Pasture, Trees, Woods

Interior

Rooms Total9
CoolingCentral A/C
Heating Yes / NoYes
HeatingForced Air
Interior FeaturesBreakfast Area, Floor Plan - Traditional, Attic, Built-Ins, Carpet, Ceiling Fan(s), Entry Level Bedroom, Formal/Separate Dining Room, Kitchen - Eat-In, Pantry, Primary Bath(s), Recessed Lighting, Walk-in Closet(s), Water Treat System, Window Treatments, Wood Floors
Window FeaturesBay/Bow, ENERGY STAR Qualified
AppliancesBuilt-In Microwave, Dishwasher, Disposal, Dryer - Electric, Dryer - Front Loading, Exhaust Fan, Extra Refrigerator/Freezer, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances, Stove, Washer, Water Conditioner - Owned, Water Heater

Exterior

Exterior FeaturesPrivate Beach
RoofArchitectural Shingle
Construction MaterialsVinyl Siding
Foundation DetailsCrawl Space
Lot FeaturesBacks to Trees, Front Yard, Landscaping, Partly Wooded

Parking

Garage Yes / NoYes
Parking FeaturesGravel Driveway

Utilities

UtilitiesCable TV, Propane

Taxes

Tax Annual Amount4695

Area Information

StateMD
CountyKENT MD
CityCHESTERTOWN
Zip Code21620
AreaKENT MD
Community NameGREAT OAK ESTATES
School DistrictKENT COUNTY PUBLIC SCHOOLS
High SchoolKENT COUNTY
Listing VS Median (in GREAT OAK ESTATES)
Price:
$649,000
low | high
Med:
$649,000
50% of Average
sqft:
2,864
low | high
Med:
2,864
50% of Average
$ / sqft:
$227
low | high
Med:
$227
50% of Average
On site:
22
low | high
Med:
22
100% of Average
Sourced by Back At You

Market Activity 21620

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Learn More About This Property

StateMD
CountyKENT MD
CityCHESTERTOWN
Zip Code21620
AreaKENT MD
Community NameGREAT OAK ESTATES
School DistrictKENT COUNTY PUBLIC SCHOOLS
High SchoolKENT COUNTY
Listing VS Median (in GREAT OAK ESTATES)
Price:
$649,000
low | high
Med:
$649,000
50% of Average
sqft:
2,864
low | high
Med:
2,864
50% of Average
$ / sqft:
$227
low | high
Med:
$227
50% of Average
On site:
22
low | high
Med:
22
100% of Average
Sourced by Back At You
Listing Updated: September 8, 2026 at 10:58:48 AM PDT