Just Reduced!! Deerpond, originally settled in Revolutionary War era Maryland, is 5.4 acres of magnificent waterfront property for lovers of Eastern Shore charisma and modern luxury. The 4 bedroom, 4 bath Main Home and separate Carriage House with 1 bedroom, and 1 bath, offer a fantastic combined 5200 square feet of living space. Inside the updated 4,500 square foot home, the great room’s sky-high windows highlight expansive water views, gracefully milled moldings, hardwood floors, and soaring transitions. In the elegant kitchen, high-end appliances and custom cabinetry help create summer bites for the enclosed wood-clad screened porch, and for holiday meals in the formal dining room. Throughout the home, winter-warming fireplaces and conversation-sparking built-ins dot living spaces perfect for cheer, reading, and relaxing. In evening, the 3rd floor home-theater entertains, while four bedrooms, and four bathrooms pamper. Whether from the balconies, decks, or in-ground gunite pool, views will entice a swim, a visit to guests staying in your fully-independent carriage house, or to wander by sweeps of English and formal gardens. Lit at twilight, your private pier stretches across wetlands and is ready to launch floating adventures. Numerous upgrades include fiber internet, newer roof, thermal windows, and two Geothermal heating and cooling systems. From Deerpond, enjoy exploring Little Choptank River Sanctuary or take a short drive to historic Cambridge with local shops and dining.
Single-familyProperty Type
1997Year Built
5.4 acresLot Size
$420Est. Price/Sq.Ft.
2 car garageParking
Listed by Trey Rider• TTR Sotheby's International Realty
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Beds
—
Baths
4
Stories
2.5
Lot width
—
Lot depth
—
Lot size
5.4 Acres
Year renovated
—
Sq. Ft.
4,473
Year built
1997
Style
Single Family Residential
County
Dorchester County
APN
16 005789
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 17, 2026.
RR
Rural Residential District
The Rural Residential District is established to encourage and concentrate low- to medium-density residential development in limited areas of the county, near existing towns or in development corridors where public services can be efficiently provided, thereby helping to preserve Resource Conservation and Agricultural Conservation Districts. Rural Residential Districts are not to be served by public community water or sewer systems.
Permitted uses
Include but are not limited to:
Livestock production
Housing-Single unit
Housing-Student
Bed & breakfast
Public service
Recreation
Communications tower
Agriculture-Cropland
Park & open space
Timberland
Property details
Parking
Parking Information
# of Detached Garage Spaces: 2
Garage Features: Garage - Front Entry, Garage Door Opener
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Detached Garage
Interior
Virtual Tour
Bedroom Information
# of Bedrooms On 1st Upper Level: 4
# of Bedrooms On Main Level: 1
Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 2
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full) On All Upper Levels: 2
# of Bathrooms (Full): 4
Interior Information
Appliances: Dishwasher, Disposal, Microwave, Oven/Range - Gas, Refrigerator, Washer, Dryer, Central Vacuum, Intercom, Washer/Dryer Stacked, Water Heater
Flooring Type: Solid Hardwood
Interior Features: Central Vacuum, Chair Railings, Crown Moldings, Entry Level Bedroom, Family Room Off Kitchen, Formal/Separate Dining Room, Intercom, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen - Island, Kitchen - Table Space, Pantry, Master Bath(s), Recessed Lighting, Tub Shower, Stall Shower, Upgraded Countertops, Walk-in Closet(s), Wet/Dry Bar, Wood Floors, Built-Ins, CeilngFan(s)
Construction Materials: Brick, Batts Insulation, Vinyl Siding
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Balcony, Deck(s), Screened, Porch(es)
Roof: Architectural Shingle
Structure Type: Detached
Window Features: Energy Efficient
Other Structures: Carriage House, Storage Barn/Shed
Exterior Information
BBQ Grill, Exterior Lighting, Outbuilding(s), Flood Lights, Gutter System
Pool Information
Personal Pool
Gunite, In Ground, Pool/Spa Combo
Lot Information
Lot Features: Front Yard, Landscaping, Rear Yard, Rip-Rapped
Navigable Water
Has Water View
Water Frontage In Feet: 500
Tidal Water: Yes
Land Information
Land Assessed Value: $258,400
Dock Information
Dock Type and Features: Hoist/Lift Electric
Dock/Slip Conveyance: Physical Dock/Slip Conveys
# of Docks: 1
Dock/Slip Conveys: Yes
Above Grade Information
Finished Sq.Ft.: 4,473
Finished Sq.Ft. Source: Assessor
Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor
Financial
Tax Information
County Tax: $8,701
Tax Assessed Value: $782,500
Tax Year: 2021
Tax Annual Amount: $8,701
Assessments Information
Year Assessed: 2021
Utilities
Utilities Information
Fiber Optic
Central Air
Cooling Type: Geothermal, Heat Pump(s), Central A/C
Cooling Fuel: Geothermal, Electric
200+ Amp Service
Heat Pump(s), Zoned
Heating Fuel: Geo-thermal, Electric
Hot Water: Electric
Sewer Septic: Shared Septic
Cable TV Available, Electric Available, Propane
Water Source: Well
Location
School Information
School District Name: DORCHESTER COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent
Location Information
Outside City Limits
Directions: US-50E/Ocean Gateway, Turn right onto Woods Road, at the traffic circle, take the 1st exit onto MD-16, exit the traffic circle onto MD-16, Turn right onto Brooks Road
Mean Low Water Feet: 5
Waterfrontage Information
Water Access Features: Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Swimming Allowed, Waterski/Wakeboard, Sail
Water Access
Private Dock Site, Rip-Rap
On Waterfront
Water Oriented
Water Body Type: River
Water Body Name: Fishing Creek
Public facts
Beds: —
Baths: 4.0
Sq. Ft.: 4,473
Stories: 2.5
Lot Size: 5.4 acres
Style: Single Family Residential
Year Built: 1997
Year Renovated: —
County: Dorchester County
APN: 16 005789
Home facts updated by county records on Jul 17, 2026
Around this home
Schools
South Dorchester School
Public PreK-8 • Assigned • 9.6mi
8/10
Cambridge-South Dorchester High School
Public 9-12 • Assigned • 7.0mi
2/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
10/10 Flood Factor
Estimated 80%+ chance 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
9/10 Heat Factor
7 days above 104° expected this year, 16 days in 30 years
8/10 Wind Factor
80% chance of strong winds in next 30 years
4/10 Air Factor
4 unhealthy days expected this year, 5 days in 30 years
Provided by First Street
Historical weather
Woolford, MD • 21677
Average low and high temperatures (°F)
40
27
44
31
60
42
69
51
74
59
86
68
89
74
81
66
78
64
69
53
59
44
46
32
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 9.4 hours in
June and 4.9 hours in December, which is comparable to the
U.S. average for solar exposure.
9.4 hrs
4.9 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.79M – $2.16M
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