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

  • Price: $3,500,000
  • Est. Mortgage of $/month
  • 41 Days on Market
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$
%
$/month over payments
Federal 30-year interest rate: 6.76% last updated on Sep 10, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $3,500,000List Price
  • 3Bedrooms
  • 2Bathrooms
  • 4,541Square Feet
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.
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

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More Info

Location Information

  • Date Listed08/04/2026
  • ZoningRPD
  • UsmAreaDrayden

Parking

  • Parking TypesDriveway

Basic Information

Location

  • Address45776 Boothe Road
  • Area Total4,541
  • SubdivisionNone Available
  • TownDrayden
  • StateMD
  • Zip20630
  • CountySaint Marys

Utilities

  • UtilitiesElectric Available, Other
  • Water SourceWell
  • SewerOn Site Septic
  • Water HeaterElectric, Oil
  • Heating FuelOil, Electric
  • Heat SystemOther

Water Body

  • Waterfront FeaturesPrivate Dock Site, Navigable Water
  • WaterfrontYes
  • Water Body TypeCreek
  • Water Body NameSchool House Ck to St. George's Ck
  • Water FeaturesPrivate Access
  • Water AccessYes
  • Tidal Water YNYes

Basic Information

  • MLS NumberMDSM2032920
  • Ownership InterestFee Simple
  • List Price$3,500,000
  • Square Feet4,541
  • Acreage189
  • Year Built1900
  • MLS Property TypeResidential
  • StatusACT

Building

  • Water Oriented YNYes
  • High School DistrictSt. Mary's County Public Schools
  • LocationTypeCreek/Stream
  • Broker NameCentury 21 Redwood Realty
  • Building Number45776
  • DirectionsFrom Route 5 turn onto MD-249,3.3 miles turn left onto Drayden Road,1.9 miles take a right onto Cherry field Road,1.3 miles take a right on Boothe Road. Follow the dirt road to Timerity. Take a right at the T to go to the Main House. There are 3 rental homes on the property Cottage 1 is gray. Pass it on your right leaving the Manor house. Cottage 2, Continue on the road past Cottage 1 Take the left hand turn. Follow the road to the end. Leave Cottage 2 and take a left onto dirt road to Cottage 3.
  • Main Level Total Baths1
  • Main Level Bedrooms1
  • Main Level Full Baths1
  • Upper Levels Total Full Baths1
  • Upper Levels Total Bedrooms2
  • Upper Levels Total Baths1
  • Upper Level1 Bedrooms2
  • Upper Level1 Full Baths1
  • Upper Level1 Total Baths1
  • Story ListMain, Upper 1
  • Structure Design TypeDetached
  • Construction MaterialsFrame
  • Property StyleOther
  • Bedrooms3
  • Full Bath2
  • Bathroom2
  • Laundry TypeMain Floor
  • Levels1.5
  • Fireplace YNYes
  • Fireplace2

Tax Information

  • Total Taxes Payment FrequencyAnnually
  • Tax Total Finished Sq Ft4,541
  • Tax Assessment Amount1355633
  • Tax Year2025
  • Taxes$12,868
  • County Tax$12,868
  • County Tax Payment FrequencyAnnually
  • Assessment Year2026

Property

  • New Construction YNN

Interior

  • Heating YNYes
  • CoolingNone
  • Stories1

Exterior

  • FoundationOther, Crawl Space

Property Information

  • Lot Size Square Feet8,232,840
  • Above Grade Finished Area4541

Amenities

  • PoolNo Pool
  • PricePerSqFt771
  • Other AmenitiesFireplace, Waterfront, Dock

Other

  • Other Structures ListBarn/Farm Building, Garage(s), Shed, Tenant House
  • Additional Parcels Description15 acre lot on the left as you turn onto Boothe Road. Perc test has been ordered from the Health Dept.
  • Additional Parcels YNY
  • View Count4

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 September 14, 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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