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$1,495,000

  • For Sale
  • Under Contract
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 5,241 Sq. Ft.
  • 2 Car Garage
  • Updated 1 day ago
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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 a new roof, 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

Full Property Details for 10800 Cliff Rd

General

  • Price: $1,495,000
  • Taxes: $10,841 (2025)
  • Status: Under Contract
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2005898
  • Updated: 1/14/2026
  • Added to Site: 8 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Family Room, Foyer, 2nd Stry Fam Rm, Other, Bonus Room
  • Interior Features: Breakfast Area, Ceiling Fan(s), Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen - Island, Primary Bath(s), Primary Bedroom - Bay Front, Recessed Lighting, Bathroom - Stall Shower, Walk-in Closet(s), Window Treatments, Wine Storage, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Brick, Wood, Gas/Propane
  • Appliances: Built-In Range, Commercial Range, Dishwasher, Dryer, Energy Efficient Appliances, Microwave, Range Hood, Refrigerator, Stainless Steel Appliances, Six Burner Stove, Washer - Front Loading, Water Conditioner - Owned, Water Heater

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 3
  • Main - Full Baths: 2
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 2
  • Bedrooms Main & Up: 3

Other Rooms

  • Laundry: Main Floor

Exterior

  • Exterior Features: Exterior Lighting, Outbuilding(s)
  • Porch/Patio/Deck: Porch(es), Screened, Patio(s)

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Circular Driveway, Stone Driveway
  • Parking Type: Driveway, Attached Garage
  • Garage Description: Garage - Front Entry, Additional Storage Area, Inside Access, Oversized

Location

  • County: KENT
  • Subdivision: GREAT OAK ESTATES
  • Driving Directions: Google Map
  • Direction Faces: East

School Information

  • School District: Kent County Public Schools

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric, Propane - Owned
  • Water Heater: Electric

Utilities

  • Sewer: Private Sewer
  • Water: Private
  • Utility Description: Electric Available, Propane, Phone Connected

Structural Information

  • Architectural Style: Traditional
  • Structure Type: Detached
  • Construction: Block, Brick
  • Basement: Yes
  • Basement Desc.: Combination
  • Foundation: Block
  • Roof: Architectural Shingle
  • Windows: Energy Efficient, Double Pane, Screens
  • Stories Description: Main, Upper 1
  • Square Feet: 5,241
  • Sq. Ft. Source: Assessor
  • Living Area: 5,241 Sq. Ft.
  • Finished Above Grnd: 5,241 Sq. Ft.
  • Year Built: 1997
  • Year Built Source: Assessor

Additional Structures

  • Other Structures: Shed

Lot Features

  • Property View: Bay, Panoramic, Water, Pasture
  • Lot Size (Acres): 1.36
  • Lot Size (Sq. Ft.): 59,242
  • Lot Size Source: Assessor
  • Street/Road Desc.: Stone, Dirt
  • Zoning: CAR
  • Lot Description: Front Yard, No Thru Street, Rip-Rapped, Rural, Rear Yard

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Canoe/Kayak, Fishing Allowed, Private Access, Sail, Waterski/Wakeboard, Boat - Powered, Swimming Allowed
  • Water Front Type: Bay
  • Water Front Name: Chesapeake Bay

Financial Considerations

  • Price Per Sq. Ft.: $285.25
  • Assessment Year: 2025
  • City/TownTax Freq: Annually
  • County Tax: $10,841
  • County Tax Freq: Annually
  • Tax w/Assessment: $956,033
  • Tax Amount: $10,841
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 5241

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 51

Listed by Taylor Properties, Lona Sue Todd

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Listing agent

— 10800 Cliff Rd —

  • Lona Sue Todd

    Taylor Properties

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 10800 Cliff Rd

School District:Kent County Public Schools
NameGradesDistance
Rock Hall Elementary School
21203 West Sharp Street, Rock Hall, MD 21661
PK-59.9 mi
Kent County Middle School
402 East Campus Avenue, Chestertown, MD 21620
6-88.5 mi
Kent County High School
25301 Lambs Meadow Road, Worton, MD 21678
9-125.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 10800 Cliff Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/08/2026
Listed
$1,495,000
121.48%
MLS
9/26/2019
Sold
$675,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 10800 Cliff Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,901
4%
$956,033
4%
2024
$10,453
6%
$916,500
3%
2023
$9,858
—
$894,100
3%
2022
$9,858
5%
$871,700
3%
2020
$9,345
—
$849,300
4%
2021
$9,345
109%
$818,767
4%
2020
$4,469
-48%
$788,233
4%
2019
$8,652
—
$757,700
—
2018
$8,652
—
$757,700
—
2017
$8,652
3%
$757,700
-1%
2015
$8,420
4%
$764,000
—
2014
$8,062
—
$764,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Taylor Properties, Lona Sue Todd

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10800 Cliff Road, Chestertown, MD 21620 (MLS# MDKE2005898) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 10800 Cliff Road is currently listed for $1,495,000 and was received on January 08, 2026. Want to learn more about 10800 Cliff Road? Do you have questions about finding other Single Family real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.

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