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45776 Boothe RoadDrayden, MD 20630Price: $3,500,000

  • Price: $3,500,000
  • Est. Mortgage of $/month
  • 17 Days on Market
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Federal 30-year interest rate: 7.32% last updated on Oct 22, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
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  • 189Acreage
  • AGRICULTUREZoning
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 serves the residence and a grandfathered previous pier depicted by the remaining pilings 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.
Listed by Sharon L Cox of Century 21 Redwood Realty

Driving Directions

Railey Vacations
Railey Vacations
Office: 301-387-2124
5 Vacation Way
McHenry, MD 21541

More Info

Location Information

  • UsmAreaDrayden

School Information

  • High School DistrictSt. Mary's County Public Schools

Parking

  • Parking TypesDriveway

Location

  • SubdivisionWestbury
  • Address45776 Boothe Road
  • Building Number45776
  • CountySaint Marys
  • DirectionsFrom Route 5 turn onto Md-249,3.3 miles turn left onto drayden Road,1.9 miles turn right onto Cherryfield Road,1.3 miles turn right onto Boothe Road ( also known as Mr Gees Way), Follow the dirt road to 45776 Boothe Road. Take a right at the T to go to the main house. There are 4 dwellings on the property. 1. main house (take a left at the T. 2. Cottage 1.Leaving the main house you will pass it on your right Gray siding) Cottage 2 follow the road past Cottage 1 and take the road to your left. Follow the road to Cottage 2. Cottage 3 Leave Cottage and take the left at the fork. Follow the road to Cottage 3.
  • Living Area SourceEstimated
  • StateMD
  • TownDrayden
  • Water Oriented YNYes
  • Zip20630

Utilities

  • CoolingNone
  • Heat SystemBaseboard - Hot Water, Baseboard - Electric
  • Heating FuelElectric, Oil
  • Heating YNYes
  • SewerSeptic Exists
  • Water HeaterElectric, Oil
  • Water SourceWell

Basic Information

  • Broker NameCentury 21 Redwood Realty
  • Habitable Residence YNY
  • List Price$3,500,000
  • MLS NumberMDSM2033824
  • MLS Property TypeLand
  • Price Per Square Foot771
  • StatusACT

Building

  • Bathroom2
  • Year Built1790
  • Bedrooms3
  • Construction MaterialsFrame, Combination, Vinyl Siding, Other
  • Fireplace2
  • Fireplace YNYes
  • FoundationCrawl Space, Other
  • Full Bath2
  • Levels1.5
  • Main Level Bedrooms3
  • Main Level Full Baths2
  • Main Level Total Baths2
  • Square Feet4,541
  • Stories1
  • Story ListMain
  • Structure Design TypeDetached

Interior

  • Interior FeaturesWood Floors, Floor Plan - Traditional, Entry Level Bedroom, Crown Moldings, Combination Kitchen/Dining

Amenities

  • Other AmenitiesFireplace, Waterfront
  • PoolNo Pool

Other

  • Crops Included YNN
  • Ground Rent Payment FrequencyAnnually
  • Other Structures List
    • 2nd House
    • Barn
    • Barn/Farm Building
    • Garage(s)
    • Shed
    • Storage Barn/Shed
    • Tenant House
  • View Count2

Tax Information

  • Assessment Year2026
  • Tax Assessment Amount1385500
  • Tax Year2026
  • Taxes$12,868
  • Total Taxes Payment FrequencyAnnually

Basic Information

Property

  • Acreage189
  • ZoningAGRICULTURE
  • Above Grade Finished Area4541
  • Above Grade Finished Area SourceEstimated
  • Above Grade Finished Area UnitsSquare Feet
  • Farm FeaturesOther Residence
  • Farm Land Area UnitsAcres
  • Farm OperationRow Crop, General
  • Farm RemarksFarm land is leased to a local farmer renewable on a yearly basis approximately 1/3 of property is currently farmland
  • Lot Size SourceEstimated
  • Lot Size Square Feet8,232,840
  • New Construction YNN

Property Information

  • Area Total4,541
  • Area Total SourceEstimated

Water Body

  • Water Body NameSt. Georg's Creek
  • Water AccessYes
  • Water Body TypeCreek
  • Water FeaturesSail, Private Access, Canoe/Kayak, Boat - Powered, Waterski/Wakeboard
  • WaterfrontYes
  • Waterfront FeaturesNavigable Water

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Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Railey Vacations participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated October 24, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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