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
For sale
$1,495,000
10800 Cliff Rd, Chestertown, MD 21620
5beds
5,241sqft
Est.:
Single Family Residence
Built in 1997
1.36 Acres Lot
$-- Zestimate®
$285/sqft
$-- HOA
What's special
Chesapeake bay waterfrontElegant formal dining roomNew roofSpacious gathering room
- 6 days |
- 1,686 |
- 45 |
Zillow last checked: 8 hours ago
Listing updated: January 12, 2026 at 05:04am
Listed by:
Lona Sue Todd 410-310-0222,
Taylor Properties 301-970-2447
Source: Bright MLS,MLS#: MDKE2005898
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bathrooms: 3
- Main level bedrooms: 3
Rooms
- Room types: 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
Primary bedroom
- Features: Flooring - Carpet
- Level: Main
- Area: 266 Square Feet
- Dimensions: 14 X 19
Bedroom 2
- Features: Flooring - Carpet
- Level: Main
- Area: 156 Square Feet
- Dimensions: 12 X 13
Bedroom 3
- Level: Main
- Area: 182 Square Feet
- Dimensions: 13 X 14
Bedroom 4
- Features: Flooring - Carpet
- Level: Upper
- Area: 247 Square Feet
- Dimensions: 13 X 19
Bedroom 5
- Features: Flooring - Carpet
- Level: Upper
- Area: 247 Square Feet
- Dimensions: 13 X 19
Other
- Level: Upper
Bonus room
- Features: Attic - Floored
- Level: Upper
Dining room
- Features: Flooring - HardWood
- Level: Main
- Area: 234 Square Feet
- Dimensions: 13 X 18
Family room
- Features: Fireplace - Wood Burning, Flooring - HardWood, Cathedral/Vaulted Ceiling
- Level: Main
- Area: 551 Square Feet
- Dimensions: 19 X 29
Foyer
- Level: Main
- Area: 143 Square Feet
- Dimensions: 11 X 13
Kitchen
- Features: Double Sink, Kitchen - Propane Cooking, Kitchen Island
- Level: Main
- Area: 390 Square Feet
- Dimensions: 13 X 30
Living room
- Features: Flooring - HardWood, Fireplace - Gas
- Level: Main
- Area: 432 Square Feet
- Dimensions: 16 X 27
Other
- Features: Flooring - Concrete
- Level: Lower
- Area: 238 Square Feet
- Dimensions: 14 X 17
Heating
- Heat Pump, Electric, Propane
Cooling
- Central Air, Electric
Appliances
- Included: Built-In Range, Range, Dishwasher, Dryer, Energy Efficient Appliances, Microwave, Range Hood, Refrigerator, Stainless Steel Appliance(s), Six Burner Stove, Washer, Water Conditioner - Owned, Water Heater, Electric Water Heater
- Laundry: Main Level
Features
- Breakfast Area, Ceiling Fan(s), Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Open Floorplan, Formal/Separate Dining Room, Eat-in Kitchen, Kitchen - Gourmet, Kitchen Island, Primary Bath(s), Primary Bedroom - Bay Front, Recessed Lighting, Bathroom - Stall Shower, Walk-In Closet(s), Wine Storage
- Flooring: Wood
- Windows: Energy Efficient, Double Pane Windows, Screens, Window Treatments
- Basement: Combination
- Number of fireplaces: 2
- Fireplace features: Brick, Wood Burning, Gas/Propane
Interior area
- Total structure area: 5,241
- Total interior livable area: 5,241 sqft
- Finished area above ground: 5,241
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Front, Storage, Inside Entrance, Oversized, Circular Driveway, Driveway, Attached
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Accessible Hallway(s)
Features
- Levels: Two
- Stories: 2
- Patio & porch: Porch, Screened, Patio
- Exterior features: Lighting
- Pool features: None
- Has view: Yes
- View description: Bay, Panoramic, Water, Pasture
- Has water view: Yes
- Water view: Bay,Water
- Waterfront features: Rip-Rap, Private Dock Site, Canoe/Kayak, Fishing Allowed, Private Access, Sail, Waterski/Wakeboard, Boat - Powered, Swimming Allowed, Bay
- Body of water: Chesapeake Bay
- Frontage length: Water Frontage Ft: 150
Lot
- Size: 1.36 Acres
- Features: Front Yard, No Thru Street, Rip-Rapped, Rural, Rear Yard
Details
- Additional structures: Above Grade, Below Grade, Outbuilding
- Parcel number: 1506000428
- Zoning: CAR
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Block, Brick
- Foundation: Block
- Roof: Architectural Shingle
Condition
- New construction: No
- Year built: 1997
Utilities & green energy
- Sewer: Private Sewer
- Water: Private
- Utilities for property: Electricity Available, Propane, Phone Connected
Community & HOA
Community
- Subdivision: Great Oak Estates
HOA
- Has HOA: No
Location
- Region: Chestertown
Financial & listing details
- Price per square foot: $285/sqft
- Tax assessed value: $956,033
- Annual tax amount: $10,841
- Date on market: 1/8/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
- Road surface type: Stone, Dirt
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 1/8/2026 | Listed for sale | $1,495,000+121.5%$285/sqft |
Source:  Bright MLS #MDKE2005898 Report a problem | ||
| 11/1/2019 | Sold | $675,000-3.5%$129/sqft |
Source: Public Record Report a problem | ||
| 8/8/2019 | Pending sale | $699,500$133/sqft |
Source: Long & Foster Real Estate, Inc. #MDKE114924 Report a problem | ||
| 7/31/2019 | Price change | $699,500-3.5%$133/sqft |
Source: Long & Foster Real Estate, Inc. #MDKE114924 Report a problem | ||
| 7/29/2019 | Price change | $724,900-3.3%$138/sqft |
Source: Long & Foster Real Estate, Inc. #MDKE114924 Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $956,033 +4.3% |
| 2024 | $10,393 +2.5% | $916,500 +2.5% |
| 2023 | $10,139 +3.5% | $894,100 -2.4% |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$9,116/mo
Principal & interest
$7422
Property taxes
$1171
Home insurance
$523
Climate risks
Neighborhood: 21620
Nearby schools
GreatSchools rating
- 5/10Rock Hall Elementary SchoolGrades: PK-5Distance: 9.9 mi
- 2/10Kent County Middle SchoolGrades: 6-8Distance: 8.5 mi
- 5/10Kent County High SchoolGrades: 9-12Distance: 5.9 mi
Schools provided by the listing agent
- District: Kent County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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