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5499 Anderby Hall Rd, 
Royal Oak, MD 21662

$4,000,000


3

Beds


4

Baths


5,921

Sq Ft


Single Family

Active

Last updated:

November 13, 2026, 03:01 PM

MLS#

MDTA2011958

Source:

BRIGHTMLS

Company Logo

About This Home

5499 Anderby Hall Rd

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.

Home Facts

Single Family

4 Baths

3 Bedrooms

Built in 1980

Subdivision & Development:

ROYAL OAK

Price Summary

4,000,000

$675 per Sq. Ft.

MLS #:

MDTA2011958

Last Updated:

November 13, 2026, 03:01 PM

Added:

a year 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:

$4,000,000

Price per Sq. Ft:

$675 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.