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5499 Anderby Hall Road, Royal Oak, MD 21662

$4,000,000
  • 5499 Anderby Hall Road, Royal Oak, MD 21662 Main Photo

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Price Reduced $1,000,000 on October 11th, 2026
BEDS3 BATHS4 full SQUARE FEET5,921 MLS#MDTA2011958
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONROYAL OAK SCHOOLTALBOT COUNTY PUBLIC SCHOOLS

Property Description

Exceptional opportunity to own a private Eastern Shore estate in Royal Oak. Anderby Hall, rooted in an original 1680 land grant, spans 12± breathtaking acres with over 3,260 feet of rip-rapped shoreline. Complete with a tidal pond, private cove, and an exclusive island peninsula connected by bridge, this estate offers unmatched privacy and natural beauty. Pass through the gated entrance to the 3,000± sq. ft. main residence featuring hand-hewn ceiling beams, antique pine floors, a great room with a fireplace, and a gourmet kitchen with a granite island. The main-floor primary suite boasts dual closets, while a second-floor office/den provides a quiet workspace. Nearly every room frames unobstructed views of Irish Creek. Step outside to brick walkways leading to a waterside custom pool. Boaters will appreciate the private deep-water dock (5' MLW) with two slips, offering quick access to the Choptank River. Outstanding property features include a 2,600 sq. ft. guest house, a tennis/pickleball court with a gazebo, a 30'x50' insulated 3-car garage, an additional 1-car garage/workshop, a new well, and a service shed. Enjoy an extraordinary coastal lifestyle surrounded by abundant wildlife, just minutes from St. Michaels and Easton.

5499 Anderby Hall Road | MLS# MDTA2011958

This single family home located at 5499 Anderby Hall Road, Royal Oak, MD 21662 is currently listed for sale with an asking price of $4,000,000. This property was built in 1980 and has 3 bedrooms and 4 full baths with 5921 sq. ft. Anderby Hall Road is located in the ROYAL OAK subdivision within the TALBOT COUNTY PUBLIC SCHOOLS school district. Search ROYAL OAK real estate on www.gilperrone.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central A/C, Ceiling Fan(s), Dehumidifier, Programmab
Fireplaces: 5
Fuel Type: Propane - Owned
Garage: 3
Heating: Central, Programmable Thermostat, Zoned
Home Style: Colonial
Lot Size: 12.79 Acres
Stories: 2.0
Taxes: $19,088
Year Built: 1980

Feature Descriptions

Accessibility: Level Entry - Main
Additional Structures: Above Grade, Below Grade
Appliances: Cooktop, Cooktop - Down Draft, Dishwasher, Dryer - Electric, Exhaust Fan, Extra Refrigerator/Freezer, Icemaker, Microwave, Oven - Double, Oven - Self Cleaning, Oven - Wall, Oven/Range - Gas, Refrigerator, Stove, Washer, Water Conditioner - Owned, Water Heater
Exterior: Brick, Stick Built
Exterior: Awning(s), Extensive Hardscape, Exterior Lighting, Outbuilding(s), Satellite Dish, Sidewalks, Tennis Court(s)
Fencing: Partially, Split Rail
Fireplace: Brick, Equipment, Mantel(s), Screen, Wood
Flooring: Carpet, Ceramic Tile, Hardwood, Slate, Tile/Brick, Vinyl
Interior: Attic, Bathroom - Jetted Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Built-Ins, Carpet, Cedar Closet(s), Ceiling Fan(s), Combination Kitchen/Dining, Dining Area, Entry Level Bedroom, Exposed Beams, Family Room Off Kitchen, Floor Plan - Traditional, Kitchen - Island, Primary Bath(s), Recessed Lighting, Skylight(s), Upgraded Countertops, Walk-in Closet(s), Water Treat System, Wood Floors, Window Treatments
Lake Name: Irish Creek
Location: Creek/Stream
Lot: Front Yard, Landscaping, Partly Wooded, Premium, Private, Rear Yard, Road Frontage, Secluded, SideYard(s), Stream/Creek, Trees/Wooded, Pond
Lot Dimensions: 12.79 Acre(S)
Parking Features: Asphalt Driveway, Circular Driveway, Private
Parking Notes: 3 Total Parking Spaces
Rooms: Living Room, Dining Room, Primary Bedroom, Bedroom 2,Bedroom 3,Kitchen, Sun/Florida Room, Office, Bathroom 2,Bathroom 3,Primary Bathroom
Sewer: Septic Exists
Special View Info: Creek/Stream, Water
SQFT Above Finished: 5921
SQFT Total Finished: 5921
Structure Type: Detached
Swimming Pool: Heated, In Ground, Concrete
Total Garage/Parking Spaces: 3
Utilities: Propane, Under Ground
Water: Well
Water Access: Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access
Waterfront: Private Dock Site, Rip-Rap
Wooded: Yes

Room Sizes

Living Room: 27 x 15 Level - Main
Dining Room: 15 x 15 Level - Main
Kitchen: 24 x 14 Level - Main
Primary Bedroom: 27 x 18 Level - Main
Primary Bathroom: 12 x 11 Level - Main
Sun/Florida Room: 31 x 13 Level - Main
Bathroom 2: 11 x 10 Level - Main
Bedroom 2: 21 x 15 Level - Upper 1
Bedroom 3: 17 x 15 Level - Upper 1
Office: 20 x 13 Level - Upper 1
Bathroom 3: 10 x 6 Level - Upper 1

Local Schools

School District: TALBOT COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Coldwell Banker Realty
Agency Phone: 4105434545

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Estimated Payment

$ 11,659.60 per month $8,902.27 Principal & Interest $1,590.67 Property Tax $1,166.67 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 10/29/2026. The listing information on this page last changed on 10/29/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 10/29/2026 12:00:08 AM EST) or Bright MLS (last updated Wed 10/28/2026 7:53:39 AM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Gilbert Perrone 

353 S. Main Street, Bel Air, MD 21014
410-697-8100

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