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5499 ANDERBY HALL ROAD
About This Property
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.
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What does this mean?
Based on our analysis, the cap rate of this property is 1.25%. A negative cap rate indicates that the property might not be feasible as an income-producing asset. The median cap rate for a near zip code 11238 is 4.23%.
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Actual monthly rental income may vary between $4,760 and $7,140 depending on unit-specific characteristics. You can change the amount using the slider to further explore.
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Cap Rate = Net Operating Income (NOI) / Property Asset Value.
When calculating the cap rate, we assume 100% occupancy. Leverage (mortgage) is not considered.
Cap Rate provided by RealtyHop and RentHop, learn more about cap rate here.
Price History
| Date / Event | Date | Event | Price |
|---|---|---|---|
| Sep 25, 2026 | Price Decreased |
$4,000,000
↓ $1M
(20%) | |
| Price Decreased | |||
| Jun 4, 2026 | Price Decreased |
$5,000,000
↓ $500K
(9.1%) | |
| Price Decreased | |||
| Mar 9, 2026 | Price Decreased |
$5,500,000
↓ $500K
(8.3%) | |
| Price Decreased | |||
| Oct 11, 2025 | Listed by Coldwell Banker Realty | $6,000,000 | |
| Listed by Coldwell Banker Realty | |||
| Nov 29, 2024 | Listed | $6,000,000 | |
| Listed | |||
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Welcome to 5499 Anderby Hall, a stunning waterfront estate which is steeped in history dating back to a land grant given in 1680 to Richard Peacock , who at that time was the chief surveyor of Talbot County! Just shy of 13 beautiful acres on Irish Creek which is a tributary of the Choptank River, you will enjoy privacy along with serene and tranquil water views from every room of the Main Residence as well as from the spacious Guest House.
This very unique offering boasts a park-like setting, 3260' of shoreline, mostly rip-rapped, 3000+ sq. ft. Main Residence, private dock with 5' mlw, a 2693" sq. ft. waterfront Guest House with an additional 3 bedrooms, 2 baths and vaulted ceilings. Entertaining your family and friends will be so easy as they can enjoy the waterside inground Pool, brick Patio, Tennis Court and Gazebo not to mention fishing and boating the waterways!
To complete the estate's amenities are a 30' X 50' Detached 3 Car Garage, another Detached Single Car Garage & Workshop, Shed for extra storage, a bridged Tidal Pond and your very own peninsula to explore or simply enjoy the nature that abounds. Security Gates, landscaped grounds, paved circular drive & brick sidewalks and so much more compliment this beautiful estate. The Seller is conveying an historic album relating to the estate as well as another album he has prepared with the many improvements he has made over the 14 years of ownership.
This estate combines historic charm with modern elegance. It is not just a home - it's a legacy! Ideal for those seeking tranquility, outdoor recreation or an entertainer's paradise. Close to Easton and St. Michaels, this estate is your gateway to the best of Chesapeake Bay living. Now is the time to escape to the Eastern Shore and enjoy this unique offering as your primary residence or as an amazing getaway from the hustle and bustle of city life! Just imagine yourself on this private point! This could be your very own piece of paradise!
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Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017