This exquisite Chesapeake Bay Waterfront home is the definition of perfection! Stunning panoramic sunsets and broad water views are yours from nearly every room. An incredible four season room with large picture windows and tile floors flows into the gourmet kitchen and open dining area. The kitchen features a six-burner Viking gas range and double oven, granite counters, custom wood cabinetry, and large island. A two-story living room with double-sided gas fireplace allows access to the waterside deck with elevated views. Some of the best views are reserved for the beautiful Master suite, offering vaulted ceilings, a private balcony, and a large Master bath with tiled shower enclosure, double vanity and luxurious soaking tub. Three additional bedrooms and two full baths provide ample space for guests. Rounding out the complete package is the sizeable finished basement with premium sound, flat screen and projector and game area, as well as an attached 3-car garage. Bold, elevated views, a private beach, privacy, and a long list of amenities make this property one of a kind!
Single-familyProperty Type
2005Year Built
1.36 acresLot Size
$340Est. Price/Sq.Ft.
3 garage spacesParking
Listed by Sarah King• Cross Street Realtors, LLC
•410-643-3066 (broker)
Listed by Stacy L Kendall• Cross Street Realtors LLC
Click on Virtual Tours to Walk Through The Home or Watch Aerial Video - This home features a gourmet kitchen that will satisfy any culinary artist, open floor plan with centralized fireplace, floor to ceiling windows to appreciate the unobstructed views of the Bay, elegant master suite with private balcony, 3-bay garage + Great Oak amenities, sandy beach, tennis, pool, dining, and more!
Outdoor Living Structures: Balcony, Deck(s), Patio(s)
Roof: Asphalt
Structure Type: Detached
Window Features: Bay/Bow, Energy Efficient, Palladian, Screens
Exterior Information
Private Beach
Pool Information
Community Pool Features: Concrete, In Ground
Community Pool
Lot Information
Lot Features: Private, Rip-Rapped, Landscaping
Navigable Water
Has Water View
Water Frontage In Feet: 150
Tidal Water: Yes
Above Grade Information
Finished Sq.Ft.: 4,358
Finished Sq.Ft. Source: Estimated
Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Financial
Tax Information
Agricultural Tax Due: No
County Tax: $7,673
Tax Assessed Value: $750,767
Tax Year: 2018
Tax Annual Amount: $8,514
Assessments Information
Year Assessed: 2019
Lease Information
Lease Considered: No
Utilities
Utilities Information
Central Air
Cooling Type: Ceiling Fan(s), Central A/C, Zoned
Cooling Fuel: Electric
120/240V
Heat Pump(s)
Heating Fuel: Propane - Leased, Electric
Hot Water: Propane
Sewer Septic: On Site Septic
Fiber Optics Available, Phone, Propane
Water Source: Private, Well
Location
Homeowners Association Information
HOA/Condo/Coop Amenities: Beach, Golf Course, Pool - Outdoor, Swimming Pool, Tennis Courts, Water/Lake Privileges
HOA Fee: $60
HOA Fee Frequency: Annually
School Information
School District Name: KENT COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent
Location Information
Outside City Limits
Directions: From Chestertown circle take Route 20 toward Rock Hall, turn right onto Flatland Road (Route 514) and then turn left to stay on Flatland Road. Cross 298 onto Handy Point Road, then turn left onto Great Oak Landing Road and a slight right onto Cliff Road. Property is on the left, sign posted.
Location Type: Bayfront
Mean Low Water Feet: 2
Waterfrontage Information
Water Access Features: Boat - Powered, Canoe/Kayak, Private Access, Waterski/Wakeboard
Water Access
Rip-Rap, Sandy Beach
On Waterfront
Water Oriented
Water Body Type: Bay
Water Body Name: Chesapeake Bay
Public facts
Beds: —
Baths: 2.5
Sq. Ft.: 4,094
Stories: 3.0
Lot Size: 1.36 acres
Style: Single Family Residential
Year Built: 2005
Year Renovated: —
County: Kent County
APN: 06 017843
Home facts updated by county records on Aug 3, 2026
Around this home
Schools
Rock Hall Elementary School
Public PreK-5 • Assigned • 10.0mi
8/10
Kent County Middle School
Public 6-8 • Assigned • 8.5mi
3/10
Kent County High School
Public 9-12 • Assigned • 5.9mi
5/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
8/10 Heat Factor
7 days above 104° expected this year, 15 days in 30 years
6/10 Wind Factor
76% chance of strong winds in next 30 years
5/10 Air Factor
6 unhealthy days expected this year, 9 days in 30 years
Provided by First Street
Historical weather
Chestertown, MD • 21620
Average low and high temperatures (°F)
37
23
41
28
60
39
67
47
72
56
83
65
87
71
79
63
77
61
68
49
58
40
43
29
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 9.3 hours in
June and 4.6 hours in December, which is comparable to the
U.S. average for solar exposure.
9.3 hrs
4.6 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.41M – $1.71M
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