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For salePrice cut: $1M (9/25)
$4,000,000
3beds
5,921sqft

5499 Anderby Hall Rd, Royal Oak, MD 21662

3beds
5,921sqft
Single Family Residence
Built in 1980
12.79 Acres Lot
$676/sqft

What's special

Licensed shorelineSpectacular waterside poolTidal pondBrick walkwaysPrivate coveGated drivewayService shed

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.

399 days
229
2
Source: Bright MLS,MLS#: MDTA2011958MLS Logo
Travel times

Living Room

Kitchen

Dining Room

Zillow last checked:

Listing updated:

Listed by:

Val Brown 410-463-3627,

Coldwell Banker Realty 4105434545,

Listing Team: The Powell Legacy Group

Source: Bright MLS,MLS#: MDTA2011958MLS Logo

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 3
  • Bathrooms: 4
  • Full bathrooms: 4
  • Main level bathrooms: 2
  • Main level bedrooms: 1
Rooms
  • Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Sun/Florida Room, Office, Bathroom 2, Bathroom 3, Primary Bathroom
Primary bedroom
  • Features: Ceiling Fan(s), Fireplace - Wood Burning, Flooring - Carpet, Primary Bedroom - Dressing Area, Walk-In Closet(s), Window Treatments
  • Level: Main
  • Area: 486 Square Feet
  • Dimensions: 18 X 27
Bedroom 2
  • Features: Fireplace - Wood Burning, Flooring - Solid Hardwood, Window Treatments
  • Level: Upper
  • Area: 315 Square Feet
  • Dimensions: 15 X 21
Bedroom 3
  • Features: Ceiling Fan(s), Fireplace - Wood Burning, Flooring - Solid Hardwood, Window Treatments
  • Level: Upper
  • Area: 255 Square Feet
  • Dimensions: 15 X 17
Primary bathroom
  • Features: Soaking Tub, Bathroom - Walk-In Shower, Double Sink, Flooring - Ceramic Tile, Recessed Lighting
  • Level: Main
  • Area: 132 Square Feet
  • Dimensions: 11 X 12
Bathroom 2
  • Features: Bathroom - Walk-In Shower, Flooring - Vinyl, Recessed Lighting
  • Level: Main
  • Area: 110 Square Feet
  • Dimensions: 10 X 11
Bathroom 3
  • Features: Bathroom - Tub Shower, Flooring - Ceramic Tile
  • Level: Upper
  • Area: 60 Square Feet
  • Dimensions: 6 X 10
Dining room
  • Features: Flooring - Solid Hardwood, Lighting - Ceiling, Window Treatments
  • Level: Main
  • Area: 225 Square Feet
  • Dimensions: 15 X 15
Kitchen
  • Features: Breakfast Nook, Ceiling Fan(s), Granite Counters, Dining Area, Double Sink, Flooring - Other, Flooring - Solid Hardwood, Kitchen Island, Kitchen - Country, Kitchen - Propane Cooking, Lighting - Pendants, Recessed Lighting, Window Treatments
  • Level: Main
  • Area: 336 Square Feet
  • Dimensions: 14 X 24
Living room
  • Features: Fireplace - Wood Burning, Flooring - Solid Hardwood, Window Treatments
  • Level: Main
  • Area: 405 Square Feet
  • Dimensions: 15 X 27
Office
  • Features: Attached Bathroom, Attic - Access Panel, Cedar Closet(s), Flooring - Carpet, Skylight(s), Walk-In Closet(s)
  • Level: Upper
  • Area: 260 Square Feet
  • Dimensions: 13 X 20
Other
  • Features: Ceiling Fan(s), Flooring - Tile/Brick
  • Level: Main
  • Area: 403 Square Feet
  • Dimensions: 13 X 31
Heating
  • Central, Programmable Thermostat, Zoned, Propane
Cooling
  • Central Air, Ceiling Fan(s), Humidity Control, Programmable Thermostat, Zoned, Electric
Appliances
  • Included: Cooktop, Down Draft, Dishwasher, Dryer, Exhaust Fan, Extra Refrigerator/Freezer, Ice Maker, Microwave, Double Oven, Self Cleaning Oven, Oven, Oven/Range - Gas, Refrigerator, Washer, Water Conditioner - Owned, Water Heater, Water Treat System, Electric Water Heater
  • Laundry: Main Level
Features
  • Attic, Bathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Built-in Features, 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, Upgraded Countertops, Walk-In Closet(s), Beamed Ceilings, Cathedral Ceiling(s), Dry Wall, Vaulted Ceiling(s), Wood Ceilings, Wood Walls
  • Flooring: Carpet, Ceramic Tile, Hardwood, Slate, Tile/Brick, Vinyl, Wood
  • Doors: Sliding Glass
  • Windows: Skylight(s), Window Treatments
  • Has basement: No
  • Number of fireplaces: 5
  • Fireplace features: Brick, Equipment, Mantel(s), Screen, Wood Burning
Interior area
  • Total structure area: 5,921
  • Total interior livable area: 5,921 sqft
  • Finished area above ground: 5,921
  • Finished area below ground: 0
Video & virtual tour

Property

Parking
  • Total spaces: 3
  • Parking features: Garage Faces Front, Garage Door Opener, Oversized, Storage, Asphalt, Circular Driveway, Private, Detached, Driveway
  • Garage spaces: 3
  • Has uncovered spaces: Yes
Accessibility
  • Accessibility features: Accessible Entrance
Features
  • Levels: Two
  • Stories: 2
  • Patio & porch: Brick, Patio, Porch, Wrap Around
  • Exterior features: Awning(s), Extensive Hardscape, Lighting, Satellite Dish, Sidewalks, Tennis Court(s), Balcony
  • Has private pool: Yes
  • Pool features: Heated, In Ground, Concrete, Private
  • Has spa: Yes
  • Spa features: Bath
  • Fencing: Partial,Split Rail
  • Has view: Yes
  • View description: Creek/Stream, Water
  • Has water view: Yes
  • Water view: Creek/Stream,Water
  • Waterfront features: Private Dock Site, Rip-Rap, Creek/Stream, Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access
  • Body of water: Irish Creek
  • Frontage type: Road Frontage
  • Frontage length: Water Frontage Ft: 3050
Lot
  • Size: 12.79 Acres
  • Features: Front Yard, Landscaped, Wooded, Premium, Private, Rear Yard, Secluded, SideYard(s), Stream/Creek, Pond
Details
  • Additional structures: Above Grade, Below Grade, Outbuilding
  • Parcel number: 2102081636
  • Zoning: RC
  • Special conditions: Standard

Construction

Type & style
  • Home type: SingleFamily
  • Architectural style: Colonial
  • Property subtype: Single Family Residence
Materials
  • Brick, Stick Built
  • Foundation: Crawl Space
Condition
  • New construction: No
  • Year built: 1980

Utilities & green energy

  • Sewer: Septic Exists
  • Water: Well
  • Utilities for property: Propane, Underground Utilities

Community & HOA

Community
  • Security: Exterior Cameras, Motion Detectors, Security Gate, Security System, Smoke Detector(s)
  • Subdivision: Royal Oak
HOA
  • Has HOA: No
Location
  • Region: Royal Oak

Financial & listing details

  • Price per square foot: $676/sqft
  • Tax assessed value: $2,265,000
  • Annual tax amount: $19,088
  • Date on market: 10/11/2025
  • Listing agreement: Exclusive Right To Sell
  • Ownership: Fee Simple

Price history

DateEventPrice
9/25/2026Price change$4,000,000-20%$676/sqft
Source: Bright MLS #MDTA2011958 Report a problem
6/4/2026Price change$5,000,000-9.1%$844/sqft
Source: Bright MLS #MDTA2011958 Report a problem
3/9/2026Price change$5,500,000-8.3%$929/sqft
Source: Bright MLS #MDTA2011958 Report a problem
10/11/2025Listed for sale$6,000,000$1,013/sqft
Source: Bright MLS #MDTA2011958 Report a problem
2/12/2025Listing removed$6,000,000$1,013/sqft
Source: Bright MLS #MDTA2009468 Report a problem
11/29/2024Listed for sale$6,000,000+160.9%$1,013/sqft
Source: Bright MLS #MDTA2009468 Report a problem
11/17/2010Sold$2,300,000+36.5%$388/sqft
Source: Public Record Report a problem
9/9/2010Sold$1,685,000-11.3%$285/sqft
Source: Public Record Report a problem
6/5/2010Price change$1,900,000-11.6%$321/sqft
Source: Benson & Mangold, LLC #TA7310681 Report a problem
4/17/2010Listed for sale$2,150,000$363/sqft
Source: Benson & Mangold, LLC #TA7310681 Report a problem

Public tax history

YearProperty taxesTax assessment
2026$20,074 +5.2%$2,356,300 +4%
2025$19,089 -2.5%$2,265,000 +4.5%
2024$19,575 +10.5%$2,167,800 +4.7%
2023$17,712 +13%$2,070,600 +4.9%
2022$15,669 +8.6%$1,973,400 +2.5%
2021$14,423 +2.6%$1,925,133 +2.6%
2020$14,061 +2.6%$1,876,867 +2.6%
2019$13,700 +4.3%$1,828,600
2018$13,131 +5.2%$1,828,600
2017$12,486 +1%$1,828,600 -5.2%
2016$12,360 -1.2%$1,928,400 0%
2015$12,513 +1.2%$1,928,500
2014$12,360 $1,928,500 -12.9%
2013-- $2,214,200
2012-- $2,214,200
2011-- $2,214,200 -22.2%
2010-- $2,845,720 +10%
2009-- $2,586,550 +11.1%
2008-- $2,327,380 +12.5%
2007-- $2,068,210 +9.6%
2006-- $1,886,440 +10.7%
2005-- $1,704,670 +11.9%
2004-- $1,522,900 +14%
2003-- $1,335,562 +16.3%
2002-- $1,148,226 +19.5%
2001-- $960,890
Find assessor info on the county website

Monthly payment

Est. payment
$23,083/mo
Principal & interest
$20883
Property taxes
$2200
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Estimated market value

Not available

Estimated sales range

Not available

Not available

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: 21662

Nearby schools

St. Michaels Elementary School
Grades PK-5 • 5.5 miles
8/10
GreatSchools® Rating
Test Score Rating
6/10
Student Progress Rating
9/10
St. Michaels Middle/High School
Grades 6-12 • 5.5 miles
6/10
GreatSchools® Rating
Test Score Rating
6/10
College Readiness Rating
8/10
Student Progress Rating
3/10

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