5499 Anderby Hall Rd

Royal Oak, MD 21662

$5,000,000
Price
3
Beds
5,921 Sq. Ft.
$844 / Sq. Ft.
5,921
Sq. Ft.
$844
per Sq. Ft.
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Virtual Tour
Virtual Tour
aerial view of the main house on Irish Creek
front view of main residence
front view of main house
aerial view of water side
pool
entrance
living room AI photo
living room AI photo
kitchen AI photo
kitchen AI photo
dining area & kitchen AI photo
1st floor - primary bedroom AI photo
primary bathroom AI photo
walk-in closet
walk-in closet with vanity
sunroom
1st floor - full bath #2
1st floor - full bath #3
utility room
2nd floor - office over primary bedroom
2nd floor - bedroom #2
2nd floor - bedroom #3
2nd floor - full bath #4
Guest house
front view
detached 1 car garage/workshop
circular drive
foyer
great room
kitchen
utility room
primary bedroom - 1st floor
primary bathroom
2nd floor - family or game room
2nd floor - bedroom #2
2nd floor - bedroom #3
2nd floor - full bath #2
aerial view of entire property
aerial view of main house
dock
view of yard
aerial view of tennis court
3 car detached garage
aerial view of tidal pond & bridge
bridge over tidal pond
aerial view of guest house
main house - 1st floor
2nd floor above living room
2nd floor above primary bedroom
main house
guest house - 1st floor
guest house - 2nd floor
guest house

Description

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...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, 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.
  1. Listed by Valerie P Brown • Coldwell Banker Realty
    P: (410)-463-3627 val.brown@cbrealty.com

Property Details for 5499 Anderby Hall Road

Tax ID Number
2102081636
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Colonial
Levels/Stories
2
Waterfront
Yes
LISTING UPDATED: 06/04/2026 01:17 PM

Property Details for 5499 Anderby Hall Road

StatusActive
MLS #MDTA2011958
Days on Market238
Taxes$19,089 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1980
Lot Size12.79 AC / 557,132 SF
CountyTalbot County
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Location

Listing Courtesy of Coldwell Banker Realty
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Building Information for 5499 Anderby Hall Road

Stories2Year Built1980Building Size-Lot Size12.79 AC / 557,132 SF

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$26,506 per month

30 year fixed, 6.36% Interest

Principal and Interest

$24,916

Property Taxes

$1,591

HOA Dues

$0

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Property Information for 5499 Anderby Hall Road

Location
Location
  • In City Limits: No
  • School District Name: TALBOT COUNTY PUBLIC SCHOOLS
  • School District County ID: 121138072466
  • SchoolDistrictSource: Listing Agent
  • County: TALBOT
Waterfront / Water Access
Waterfront / Water Access
  • Water View: Yes
  • Water Access: Yes
  • Water Access Features: Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access
  • Water Oriented: Yes
  • Navigable Water: Yes
  • Tidal Water: Yes
  • Water Body Name: Irish Creek
  • Water Body Type: Creek
  • Water Frontage In Feet: 3050.0
  • Riparian Rights Y/N: Yes
  • Docks Count: 1
  • Dock Type and Features: Multiple Slip, Private
  • Dock/Slip Conveys Y/N: true
  • Dock/Slip Conveyance: Deeded
  • Slips Count: 2
  • Mean Low Water Feet: 5.00
Association / Community Info
Association / Community Info
  • Senior Community: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Tax Assessed Value: $2,265,000
  • Year Assessed: 2025
  • County Tax: $19,089
  • Improvement Assessed Value: $1,061,700
  • Land Assessed Value: $1,203,300
  • Clean Green Assessed: No
  • Land Use Code: R
  • Zoning: RC
  • School Tax: $0
  • Automatically Update Tax Values Y/N: Yes
Rooms
Main
  • # Bedrooms Count Main Level: 1
  • # Bathrooms Count Main Level: 2
  • # Bathrooms Full Main Level: 2
  • # Bathrooms Half Main Level: 0
All Upper Levels
  • # Bedrooms Count All Upper Levels: 2
  • # Bathrooms Count All Upper Levels: 2
  • # Bathrooms Full All Upper Levels: 2
Upper Level 1
  • # Bedrooms Count Upper Level: 2
  • # Bathrooms Count Upper Level: 2
  • # Bathrooms Full Upper Level: 2
Rooms
  • Room List: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Sun/Florida Room, Office, Bathroom 2, Bathroom 3, Primary Bathroom
  • Stories: Main, Upper 1
Rooms Information
Room 1
  • Room Type: Bathroom 2
  • Room Length: 11.0
  • Room Width: 10.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Bathroom - Walk-In Shower, Flooring - Vinyl, Lighting - Recessed
Room 2
  • Room Type: Living Room
  • Room Length: 27.0
  • Room Width: 15.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Fireplace - Wood Burning, Flooring - Solid Hardwood, Window Treatments
Room 3
  • Room Type: Dining Room
  • Room Length: 15.0
  • Room Width: 15.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Solid Hardwood, Lighting - Ceiling, Window Treatments
Room 4
  • Room Type: Kitchen
  • Room Length: 24.0
  • Room Width: 14.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Breakfast Nook, Ceiling Fan(s), Countertop(s) - Granite, Dining Area, Double Sink, Flooring - Other, Flooring - Solid Hardwood, Island, Kitchen - Country, Kitchen - Propane Cooking, Lighting - Pendants, Lighting - Recessed, Window Treatments
Room 5
  • Room Type: Primary Bedroom
  • Room Length: 27.0
  • Room Width: 18.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Ceiling Fan(s), Fireplace - Wood Burning, Flooring - Carpet, Primary Bedroom - Dressing Area, Walk-In Closet(s), Window Treatments
Room 6
  • Room Type: Primary Bathroom
  • Room Length: 12.0
  • Room Width: 11.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Bathroom - Soaking Tub, Bathroom - Walk-In Shower, Double Sink, Flooring - Ceramic Tile, Lighting - Recessed
Room 7
  • Room Type: Sun/Florida Room
  • Room Length: 31.0
  • Room Width: 13.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Ceiling Fan(s), Flooring - Tile/Brick
Room 8
  • Room Type: Bedroom 2
  • Room Length: 21.0
  • Room Width: 15.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Fireplace - Wood Burning, Flooring - Solid Hardwood, Window Treatments
Room 9
  • Room Type: Bedroom 3
  • Room Length: 17.0
  • Room Width: 15.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Ceiling Fan(s), Fireplace - Wood Burning, Flooring - Solid Hardwood, Window Treatments
Room 10
  • Room Type: Office
  • Room Length: 20.0
  • Room Width: 13.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Attached Bathroom, Attic - Access Panel, Cedar Lined Closet, Flooring - Carpet, Skylight(s), Walk-In Closet(s)
Room 11
  • Room Type: Bathroom 3
  • Room Length: 10.0
  • Room Width: 6.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Bathroom - Tub Shower, Flooring - Ceramic Tile
Building Info
Building Info
  • Total Finished SQFT: 5,921.00
  • Total Finished SQFT Source: Assessor
  • Tax Total Finished SQFT: 5,921.00
  • Total SQFT: 5,921.00
  • Total SQFT Source: Assessor
  • Construction Materials: Brick, Stick Built
  • Ext Main Mid-res: http://bright-media02.prd.brightmls.com/bright/images/0000/8042/3067/2742/804230672742_512_384_WM_bF2CMqolLAXHInbh.jpg
  • Wall and Ceiling Types: Beamed Ceilings, Brick, Cathedral Ceilings, Dry Wall, Vaulted Ceilings, Wood Ceilings, Wood Walls
  • Flooring Type: Carpet, Ceramic Tile, Hardwood, Slate, Tile/Brick, Vinyl
  • Foundation Details: Crawl Space
  • Room and Floor: Bedrooms-Main Level-1, Bathrooms Full-Main Level-1, Bathrooms Full-Main Level-2, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2
  • # Bathrooms Full: 4
  • # Bathrooms Half: 0
  • Other Structure: 2nd Garage, Gazebo, Guest House, Shed, Other, Shed Shop
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Lot Features: Front Yard, Landscaping, Partly Wooded, Premium, Private, Rear Yard, Road Frontage, Secluded, SideYard(s), Stream/Creek, Trees/Wooded, Pond
  • Fencing: Partially, Split Rail
  • Location Type: Creek/Stream
  • Parcel ID: 5293061
Parking
Parking
  • Type Of Parking: Detached Garage, Driveway
  • Num of Detached Garage Spaces: 3
  • Total Garage Spaces: 3
  • Parking Features: Asphalt Driveway, Circular Driveway, Private
  • Garage Features: Garage - Front Entry, Garage Door Opener, Oversized, Additional Storage Area
Interior Features
Interior Features
  • 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
  • Fireplace: Yes
  • Fireplaces Count: 5
  • Fireplace Features: Brick, Equipment, Mantel(s), Screen, Wood
  • 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
  • Accessibility Features: Level Entry - Main
  • Security Features: Exterior Cameras, Motion Detectors, Security Gate, Security System, Smoke Detector, Surveillance Sys
  • Door Features: Sliding Glass
  • Laundry Type: Main Floor
  • Virtual Tour URL Unbranded: https://youtu.be/zvemor-iJoE?si=qnuX5h8MD8C-CMQ8
Exterior Features
Exterior Features
  • Exterior Features: Awning(s), Extensive Hardscape, Exterior Lighting, Outbuilding(s), Satellite Dish, Sidewalks, Tennis Court(s)
  • Outdoor Living Structures: Balcony, Brick, Patio(s), Porch(es), Wrap Around
  • Pool: Yes - Personal
  • Personal Pool Features: Heated, In Ground, Concrete
Utilities
Utilities
  • Utilities: Propane, Under Ground
  • Heating: Yes
  • Cooling Type: Central A/C, Ceiling Fan(s), Dehumidifier, Programmable Thermostat, Zoned
  • Cooling Fuel: Electric
  • Heating Type: Central, Programmable Thermostat, Zoned
  • Heating Fuel: Propane - Owned
  • Hot Water: Electric
  • Water Source: Well
  • Sewer Septic: Septic Exists
Confidential Data
Listing Office
  • List Agent AOR: Mid-Shore Board of REALTORS

Property History for 5499 Anderby Hall Road

DateEvent & SourcePriceAppreciation
Jun 4, 2026

Price Change

BRIGHT #MDTA2011958

$5,000,000—
Mar 9, 2026

Price Change

BRIGHT #MDTA2011958

$5,500,000—
Oct 11, 2025

Listed (Active)

BRIGHT #MDTA2011958

$6,000,000—
DateEvent & SourcePrice
06/04/2026

Price Change

BRIGHT #MDTA2011958

$5,000,000
03/09/2026

Price Change

BRIGHT #MDTA2011958

$5,500,000
10/11/2025

Listed (Active)

BRIGHT #MDTA2011958

$6,000,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 5499 Anderby Hall Road

Taxable ValueLand$1,203,300Additions$1,061,700Total$2,265,000
Tax Record2023$16,618 ($1,385 / month)
Home Facts
Beds0Baths6Total Finished SqFt3,924 SqFtAbove Grade Finished SqFt3,924 SqFtStories2Lot Size557,132 SqFtStyleSingle Family ResidenceYear Built1980CountyTALBOTAPN02-081636Fireplace TypeHas Fireplace

Schools near 5499 Anderby Hall Road

This home is within Talbot County Public Schools.
Rating
School
Type
Grades
Distance
St. Michaels Elementary School
Public - PK to 5
St. Michaels Middle/High School
Public - 6 to 12
Easton High School
Public - 9 to 12
Rating
School
Distance
St. Michaels Elementary School
PublicPK to 5

St. Michaels Middle/High School
Public6 to 12

Easton High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 5499 Anderby Hall Road, Royal Oak, MD 21662

5499 Anderby Hall Road is a single family home for sale in Royal Oak, MD 21662. This property was listed for sale on October 11, 2025 by Coldwell Banker Realty, it's currently listed at $5,000,000. It has been on the market for a total of 238 days and was last sold on November 15, 2010. This listing's school district is Talbot County Public Schools. Nearby schools include St. Michaels Elementary School, St. Michaels Middle/High School and Easton High School. 5499 Anderby Hall Road is a 3-bed, 4-bath, 5,921 sqft single family home built in 1980.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Coldwell Banker Realty

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided 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. Data last updated on 06/04/2026 01:17 PM