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Single family home for sale at 5499 Anderby Hall Rd, Royal Oak, MD 21662 | MLS# MDTA2011958 | Listing updated on 2026-09-25
Photo 1 of Single family home for sale at 5499 Anderby Hall Rd, Royal Oak, MD 21662 | MLS# MDTA2011958 | Listing updated on 2026-09-25
Photo 2 of Single family home for sale at 5499 Anderby Hall Rd, Royal Oak, MD 21662 | MLS# MDTA2011958 | Listing updated on 2026-09-25
Photo 3 of Single family home for sale at 5499 Anderby Hall Rd, Royal Oak, MD 21662 | MLS# MDTA2011958 | Listing updated on 2026-09-25
Photo 4 of Single family home for sale at 5499 Anderby Hall Rd, Royal Oak, MD 21662 | MLS# MDTA2011958 | Listing updated on 2026-09-25
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$4,000,000

Monthly Est:$19,909

  • Beds Icon3 Beds
  • Beds Icon
    4 Baths
  • Beds Icon5,921sqft

5499 Anderby Hall Rd, Royal Oak, MD 21662

$19,909/moEst:

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  • Single Family Residence

  • Built in 1980

  • $-- HOA

  • 12.79 acres lot

  • $676/sq.ft

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 eve
ry 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.

  • Houzeo last checked: 8 hours ago
  • Listing updated: September 25, 2026 at 12:56 pm
  • Listing Provided by: Valerie P Brown (410) 463-3627 | Coldwell Banker Realty (410) 543-4545
  • Source: Bright MLS-NJ | MLS#: MDTA2011958 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Talbot Md County

  • City

    Royal Oak

  • Neighborhood

    --

  • Year Built

    1980

  • HOA Fees

    -

  • Finished Area

    5,921 sqft

  • Lot Size

    12.79 acres lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    MDTA2011958

  • MLS Status

    ACTIVE-BRIGHT

  • Days on Market

    350

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 4

Interior

  • Flooring

    Carpet, Ceramic Tile, Hardwood, Slate, Tile/brick, Vinyl

  • Sewer

    Septic Exists

  • 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 Features

    Awning(s), Extensive Hardscape, Exterior Lighting, Outbuilding(s), Satellite Dish, Sidewalks, Tennis Court(s)

  • Interior Features

    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

  • Heating

    Central, Programmable Thermostat, Zoned

  • Cooling

    Central A/c, Ceiling Fan(s), Dehumidifier, Programmable Thermostat, Zoned

Construction

  • Year Built

    Year Built: 1980

  • Home type

    Single Family Residence

  • Foundation Details

    Crawl Space

  • Architectural Style

    Colonial

  • Construction Materials

    Brick, Stick Built

Utilities & Energy

  • Pool Features

    Heated, In Ground, Concrete

  • Fireplace Features

    Brick, Equipment, Mantel(s), Screen, Wood

  • Parking Features

    Asphalt Driveway, Circular Driveway, Private

  • Water Source

    Well

  • Security Features

    Exterior Cameras, Motion Detectors, Security Gate, Security System, Smoke Detector, Surveillance Sys

  • Utilities

    Propane, Under Ground

Other Features

  • Subdivision Name

    Royal Oak

  • Patio And Porch Features

    Balcony, Brick, Patio, Porch, Wrap Around

  • Lot Features

    Front Yard, Landscaping, Partly Wooded, Premium, Private, Rear Yard, Road Frontage, Secluded, Side Yard(s), Stream/creek, Trees/wooded, Pond

Price History

DateEventPrice

09/25/2026

Source: mls_logoBright MLS-NJ #MDTA2011958

Price Decreased

$4,000,000 -20.00%

$676/sqft

06/04/2026

Source: mls_logoBright MLS-NJ #MDTA2011958

Price Decreased

$5,000,000 -9.09%

$844/sqft

03/09/2026

Source: mls_logoBright MLS-NJ #MDTA2011958

Price Increased

$5,500,000 +37.50%

$929/sqft

10/11/2025

Source: mls_logoBright MLS-NJ #MDTA2011958

Listed for Sale

$4,000,000 -33.33%

$676/sqft

10/11/2025

Source: mls_logoBright MLS-NJ #MDTA2011958

Price Increased

$6,000,000 +160.87%

$1,013/sqft

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Based on information from Bright MLS through Oct 09, 2026, 02:30PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

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