CHARIS REALTY GROUP

Traditional

22400 GREAT OAK LANDING RD.

CHESTERTOWN, MD 21620

MLS#: MDKE2006946

$649,000

Status: Active
Listing number: MDKE2006946
Listing provided by: Coldwell Banker Chesapeake Real Estate Company
Listing agent phone: None
Last update: 8 days ago
On site: 9 days ago
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GREAT OAK ESTATES - Residential

Property

Beds

4

Full Baths

3

1/2 Baths

None

Year Built

2000

Sq.Footage

2,864

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.

Features & Amenities

Interior

  • Other Interior Features

    Eat-in Kitchen, Ceiling Fan(s), Pantry, Recessed Lighting, Walk-In Closet(s), Built-in Features

  • Total Bedrooms

    4

  • Bathrooms

    3

  • Above Grade Finished Area

    2864.0

  • Basement YN

    NO

  • Cooling YN

    YES

  • Cooling

    Central Air, Ceiling Fan(s), Electric

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Exhaust Fan, Electric, Propane, Forced Air

  • Main Level Bedrooms

    2

  • Pet friendly

    Yes

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Vinyl Siding

  • Parking

    Garage Door Opener, Gravel, Garage, Driveway, Inside Entrance, Attached

  • Patio and Porch Features

    Patio

  • Pool

    No

  • Waterfront YN

    NO

  • View

    Pasture, Trees/Woods, Garden

Area & Lot

  • Lot Features

    Front Yard, Few Trees

  • Lot Size(acres)

    1.03

  • Lot Size(square feet)

    44,867

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Traditional

Price

  • Sales Price

    $649,000

  • Tax Amount

    $4,695

  • Financing Options

    Cash, Conventional, FHA, VA

  • Sq. Footage

    2,864

  • Price/SqFt

    $226

HOA

  • Association

    YES

  • Association Fee

    $100

  • Association Fee Frequency

    Annually

  • Association Fee Includes

    N/A

Property Resources

  • Horse Property

    NO

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    KENT COUNTY

Property Features

  • Stories

    2

  • New Construction

    NO

  • Association Amenities

    Golf Course, Marina

  • Senior Community YN

    NO

  • Sewer

    Septic Tank

  • Tax Lot

    65

  • Water Source

    Well

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Listing Courtesy of Terri L Kulp , Coldwell Banker Chesapeake Real Estate Company

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Agent Phil Herbert

AGENT

Phil Herbert

Call Phil today to schedule a private showing.

(240) 397-1779

phil@charisrealty.com


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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.

22400 GREAT OAK LANDING RD.

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