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Colleen McDermond
REALTOR®
Cell: (443) 802-4095
Office: (410) 814-2400

45776 Boothe Road, Drayden, MD 20630

$3,500,000
  • 45776 Boothe Road, Drayden, MD 20630 Main Photo

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BEDS3 BATHS2 full SQUARE FEET4,541 MLS#MDSM2032920
STATUSACTIVE PROPERTY TYPEResidential - Single Family SCHOOLST MARYS COUNTY PUBLIC SCHOOLS

Property Description

Welcome to Timerity, a natural sanctuary tucked away on an 189-acre waterfront estate where Southern Maryland history, productive farmland, mature woods and protected tidal waters come together in one extraordinary property. Documented by the Maryland Historical Trust as Timerity Farm, the property reflects the agricultural and maritime heritage of the Drayden area and the historic St. George’s Hundred landscape of St. Mary’s County. The Trust identifies the residence as a mid-19th-century historic resource, while an earlier survey records an owner tradition suggesting 1790. At the heart of the farm stands a distinctive one-and-one-half-story frame residence with a traditional side-passage/double-parlor plan, hardwood floors, separate fireplaces, painted moldings and a rare historic brick pent chimney. The home offers three bedrooms, including one on the main level and two upstairs, along with two full baths. A working country kitchen opens to a generous gathering space, while the side porch provides a relaxed setting for entertaining, crab feasts and enjoying the surrounding waterfront views. The property unfolds across approximately 189 acres of open farmland, mature woodland and secluded shoreline, creating an exceptional sense of privacy. Roughly rectangular in shape, the land occupies the end of a peninsula and is surrounded on three sides by water, with the public road coming to an end at the entrance to the property. The 189 acres have approximately 1/3 open farmland and 2/3 mature woodland and secluded shoreline. The agricultural fields are presently leased to a local farmer, while the wooded portions provide habitat for the abundant wildlife for which Southern Maryland’s tidewater country is known. Approximately 5,000 linear feet of protected shoreline extend along School House Creek, with boating access through St. George Creek to the Potomac River. A private pier and a grandfathered previous pier depicted by the remaining pilings serves the residence with water depth estimated at approximately 6 feet at Mean Low Water further up School House Creek. The Schoolhouse Creek shore is historically protected waterfront sheltered from severe storms and is well suited for boating, fishing, kayaking and paddleboarding. In addition to the historic residence, the property includes three modest cottages and three barns/outbuildings, adding flexibility for agricultural use, storage, workshops, guest accommodations or future restoration. Transferable Development Rights “TDR” have not been exercised and remain available. Few properties combine this degree of acreage, waterfront, privacy and documented history in one setting. Whether envisioned as a private family estate, working farm, sporting retreat, waterfront sanctuary or legacy property to be preserved for generations, Timerity, offers a rare opportunity to own an exceptional piece of Southern Maryland’s Chesapeake tidewater landscape. This estate has seen a diverse history. Ownership allows you to write the next chapter adding to the growing legacy of this waterfront retreat.

45776 Boothe Road | MLS# MDSM2032920

This single family home located at 45776 Boothe Road, Drayden, MD 20630 is currently listed for sale with an asking price of $3,500,000. This property was built in 1900 and has 3 bedrooms and 2 full baths with 4541 sq. ft. Boothe Road is located within the ST MARYS COUNTY PUBLIC SCHOOLS school district. Search Drayden real estate on colleenmcdermond.homesale.com today.

Property Features

Property Type: Residential - Single Family
Cooling: None
Fireplaces: 2
Fuel Type: Oil, Electric
Lot Size: 189.00 Acres
Stories: 1.5
Taxes: $12,868
Year Built: 1900

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Exterior: Frame
Lake Name: St. George's Creek
Location: Creek/Stream
Lot Dimensions: 189.00 Acre(S)
Sewer: On Site Septic
SQFT Above Finished: 4541
SQFT Total Finished: 4541
Structure Type: Detached
Utilities: Electric Available, Other
Water: Well
Water Access: Private Access
Waterfront: Private Dock Site

Local Schools

School District: ST MARYS COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Century 21 Redwood Realty
Agency Phone: 3012082288

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Estimated Payment

$ 9,882.65 per month $7,789.48 Principal & Interest $1,072.33 Property Tax $1,020.83 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers 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 on this site was last updated 09/07/2026. The listing information on this page last changed on 09/07/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Mon 09/07/2026 12:11:28 AM EST) or Bright MLS (last updated Mon 09/07/2026 12:03:56 AM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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