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5499 Anderby Hall Rd, 
Royal Oak, MD 21662

$5,000,000


3

Beds


4

Baths


5,921

Sq Ft


Single Family

Active

Last updated:

August 14, 2026, 01:59 PM

MLS#

MDTA2011958

Source:

BRIGHTMLS

Company Logo

About This Home

5499 Anderby Hall Rd

Now offered at an improved price of $5,000,000. Excellent opportunity to own your own private Eastern Shore estate in Royal Oak. Anderby Hall, part of an original 1680 land grant, spans a breathtaking 12+/- acre parcel featuring 3,260’+/- of rip-rapped shoreline. This exceptional property includes a tidal pond, a private cove, and an exclusive island peninsula accessed by bridge. Pass through the gated driveway to discover the main residence: a 3,000+/- sq. ft. Colonial showcasing a great room with a fireplace, charming old pine floors, hand-hewn ceiling beams, and a granite island kitchen. The luxury primary suite features his-and-her closets alongside a second-floor office/den. Nearly every room frames gorgeous, unobstructed views of Irish Creek. Outside, brick walkways lead to a spectacular waterside pool. Boaters will love the private dock offering 5' MLW, located just minutes from the Choptank River. Additional amenities include a 2,600 sq. ft. guest house, tennis courts (easily convertible to pickleball) with a gazebo, a 30x50 detached 3-car garage, an additional 1-car garage with a workshop, new well, and a service shed. Complete with a licensed shoreline and abundant local wildlife (geese, ducks, deer, and turkey), this estate is convenient to Easton and St. Michaels. Experience an unmatched lifestyle of luxury, privacy, and waterfront beauty at an incredible new value.

Home Facts

Single Family

4 Baths

3 Bedrooms

Built in 1980

Subdivision & Development:

ROYAL OAK

Price Summary

5,000,000

$844 per Sq. Ft.

MLS #:

MDTA2011958

Last Updated:

August 14, 2026, 01:59 PM

Added:

10 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

4

Interior

Living Area:

5,921 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial

Building Area:

5,921 Sq. Ft.

Year Built:

1980


Lot

Lot Size (Sq. Ft):

557,132


Finances & Disclosures

Finances

Price:

$5,000,000

Price per Sq. Ft:

$844 per Sq. Ft.

5499 Anderby Hall Rd
Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.