10800 Cliff Road, Chestertown, MD 21620-4108 $1,495,000

Beds/Baths: 5/3.1
Interior Sq. Ft: 5,241
Acreage: 1.36
Age:29 years
Style:
Traditional
MLS#: MDKE2005898
Subdivision: Great Oak Estates
Design/Type:
Detached

Description

Coming Soon – Chesapeake Bay Waterfront with Breathtaking Views. Experience exceptional waterfront living in this custom-built 5,240 sq ft residence, beautifully situated on an elevated bluff in the sought-after Great Oak Community of Chestertown, Maryland. Offering 5 bedrooms and 3.5 baths, this remarkable home captures sweeping Chesapeake Bay views and unforgettable sunsets from nearly every room. The property features 150 feet of riprap-protected shoreline and direct water access via a brand-new private 140ft pier complete with lighting, water service in four locations, a 12,000-lb boat lift, and two jet ski lifts—perfect for boating and waterfront recreation. Inside, the home impresses with 9-foot ceilings and hardwood floors throughout most of the main level. Designed for entertaining, the gourmet kitchen showcases luxury appliances, a distinctive chef’s cutting-board countertop, and new LVP flooring. The grand great room is a true showpiece, featuring a floor-to-ceiling brick wood-burning fireplace, vaulted shiplap pine ceiling, exposed beams, and views of the Bay! Additional living spaces include an elegant formal dining room, a spacious gathering room, and a casual dining area highlighted by a gas fireplace. The first-floor primary suite offers privacy and comfort with a walk-in closet and an updated bath featuring new flooring, a corner soaking tub, and dual vanities. Two additional bedrooms, a full bath, and a laundry room complete the main level. The second floor provides two generously sized bedrooms, a large living area, a full bath, and an 18’ x 22’ unfinished bonus room/man cave with a separate staircase offering access to the garage or exterior—ideal for future expansion or customization. Notable features include an oversized two-car garage with workbench, a small basement housing a state-of-the-art temperature- and humidity-controlled wine cellar, a Culligan whole-house water filtration system, and two hot water heaters. One of the home’s most captivating spaces is the expansive screened-in porch, stretching across much of the waterfront side of the home. With three ceiling fans and panoramic Chesapeake Bay views, it offers the perfect setting for relaxing or entertaining year-round. Whether you’re seeking a serene waterfront retreat or a home designed for memorable gatherings, this exceptional coastal property delivers. Just minutes from historic Chestertown, home to Washington College, waterfront dining, farmers’ markets, parks, festivals, and river cruises. Conveniently located near Safe Harbor Great Oak Marina and approximately 90 minutes from Washington, D.C. and Philadelphia. Schedule your private showing and experience Chesapeake Bay living at its finest

Bedroom 4: 19 X 13 - Upper 1
Bedroom 5: 19 X 13 - Upper 1
2nd Stry Fam Rm: Upper 1
Bonus Room: Upper 1
Kitchen: 30 X 13 - Main
Dining Room: 18 X 13 - Main
Foyer: 13 X 11 - Main
Bedroom 3: 14 X 13 - Main
Family Room: 29 X 19 - Main
Bedroom 2: 13 X 12 - Main
Primary Bed: 19 X 14 - Main
Living Room: 27 X 16 - Main
Other: 17 X 14 - Lower 1

Taxes: $10,841
Home Assoc: No
Condo Assoc: No
Garage: Y
Basement: Y
Pool: No Pool
School Dist: Kent County Public Schools

Features

Water
Water Oriented: Yes; Water Front: Yes; Water Access: Yes; Water Body Name: Chesapeake Bay; Water Body Type: Bay; Waterfront: Rip-Rap, Private Dock Site; Types of Use: Canoe/Kayak, Fishing Allowed, Private Access, Sail, Waterski/Wakeboard, Boat - Powered, Swimming Allowed; Mean Low Water: 6; Navigable: Yes;

Utilities
Heat Pump(s), Electric, Propane - Owned, Central A/C, Electric, Hot Water - Electric, Private Water, Private Sewer, Main Floor Laundry, Electric Available, Phone Connected, Propane

Garage/Parking
Attached Garage, Driveway, Additional Storage Area, Garage - Front Entry, Inside Access, Oversized, Attached Garage Spaces #: 2;

Interior
Breakfast Area, Ceiling Fan(s), Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Combination Basement, Brick Fireplace, Gas/Propane Fireplace, Wood Fireplace, Accessibility - 36"+ wide Halls, Double Pane Windows, Energy Efficient Windows, Window Screens

Exterior
Block Foundation, Architectural Shingle Roof, Block Exterior, Brick Exterior, Patio(s), Porch(es), Screened Porch/Deck, Exterior Lighting, Outbuilding(s)

Lot
Front Yard, Non-Tidal Wetland Lot, Rear Yard, Rip-Rapped Lot, Rural Lot, Bay View, Panoramic View, Pasture View, Water View, Dirt Road, Stone Road

Select a school from the following list. Schools are grouped by school type.
The schools on this list are selected by their proximity of up to 5 miles to the property address. Proximity does not guarantee enrollment eligibility. Please contact the school directly for more information on enrollment requirements.
* If there are more than 5 schools of any type within a close proximity, click on the button to see additional schools of that type near the search address.

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This report is a detailed community overview for Chestertown (21620), Maryland.

Community Quick Facts

  • Average travel time to work for people in this community: 25
  • Average salary of people in this community: $45,273

Community Summary

  • Population Density (ppl / mile): 96
  • Household Size (ppl): 2.23
  • Households w/ Children: 37%

Housing Inventory

  • Owned: 3,311 (53.4%)
  • Rented: 1,775 (28.6%)
  • Vacant: 1,110 (17.9%)
  • Total: 6,196

Population Demographics

The population of the community broken down by age group. The numbers at the top of each bar indicate the number of people in the age bracket below.

Total: 12,850
Households: 5,086
Median Age: 44.00

Climate and Weather

The Temperature chart displays average high and low values for January and July, and is designed to provide an indication of both seasonal and daily temperature variability. The Weather Risk Index indicates the calculated risk of each type of weather event occurring in the future. This risk is based on historical localized storm events and weather patterns. The national average for each type of weather event equals a score of 100, so a score of 200 would represent twice the risk as the national average, and a score of 50 would represent half the risk of the national average.

Temperature

Education

Highest Level of Education Attained

  • Less than 9th Grade: 4.6%
  • Some High School: 6.1%
  • High School Graduate: 28.4%
  • Some College: 16.5%
  • Associate Degree: 5.8%
  • Bachelor's Degree: 19.2%
  • Graduate Degree: 19.4%

Income by dollar range

Median Income: $63,806

Fair Market Rents

The Fair Market Rents show average gross rent estimates based on figures provided by the U.S. Department of Housing and Urban Development (HUD).

  • One Bedroom: $578
  • Two Bedroom: $897
  • Three Bedroom: $1,260

© 2026 LiveBy. All Rights Reserved.

Contact Information

Listing Courtesy of: Taylor Properties

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 in which Patterson-Schwartz Real Estate participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information Deemed Reliable But Not Guaranteed.
Copyright BRIGHT, All Rights Reserved
Listing data as of 1/02/2026.

10800 Cliff Road, Chestertown, MD 21620-4108

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Broker Compensation

An offer of broker compensation or seller concession is not a guarantee. All compensation offers and concessions are negotiable and subject to written agreement between the parties. Please consult with your real estate agent for more information.