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$1,524,900
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Property Description
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
Full Property Details for 10800 Cliff Rd
General
- Sold For: $1,524,900
- Taxes: $10,841 (2025)
- Status: Closed
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDKE2005898
- Added to Site: 54 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
- Terms: Standard Sale
- Tax Total Finished Sq. Ft.: 5241
Disclosures and Reports
- Ownership: Fee Simple
- Lot Number: 51
Listed by Taylor Properties, Lona Sue Todd
Sold by RE/MAX Chesapeake, Jason M Zang
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Schools
Schools serving 10800 Cliff Rd
School District:Kent County Public Schools
| Name | Grades | Distance |
|---|---|---|
Rock Hall Elementary School 21203 West Sharp Street, Rock Hall, MD 21661 | PK-5 | 9.9 mi |
Kent County Middle School 402 East Campus Avenue, Chestertown, MD 21620 | 6-8 | 8.5 mi |
Kent County High School 25301 Lambs Meadow Road, Worton, MD 21678 | 9-12 | 5.9 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
Date
Details
Price
Change
Source
2/17/2026
Sold
$1,524,900
2%
MLS
1/08/2026
Listed
$1,495,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
10800 Cliff Road, Chestertown, MD 21620 (MLS# MDKE2005898) is a Single Family property that was sold at $1,524,900 on February 17, 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.

