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$3,500,000
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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.
Full Property Details
Full Property Details for 45776 Boothe Rd
General
- Price: $3,500,000
- Taxes: $12,868 (2025)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDSM2032920
- Updated: 9/9/2026
- Added to Site: 69 day(s) ago
Interior
- Fireplace: Yes
- Number of Fireplaces: 2
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
- Upper Floor Baths: 1
- Upper - Full Baths: 1
- Main Floor Baths: 1
- Main - Full Baths: 1
Bedrooms
- Total Bedrooms: 3
- Bedrooms Upper: 2
- Bedrooms Main & Up: 1
Other Rooms
- Laundry: Main Floor
Parking
- Parking Type: Driveway
Location
- County: SAINT MARYS
- Driving Directions: From 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.
- Location Details: Creek/Stream
School Information
- School District: St. Mary's County Public Schools
Heating & Cooling
- Cooling Type: None
- Heating Type: Other
- Heating Fuel: Oil, Electric
- Water Heater: Electric, Oil
Utilities
- Sewer: On Site Septic
- Water: Well
- Utility Description: Electric Available, Other
Structural Information
- Architectural Style: Other
- Structure Type: Detached
- Construction: Frame
- Foundation: Other, Crawl Space
- Stories Description: Main, Upper 1
- Square Feet: 4,541
- Sq. Ft. Source: Assessor
- Living Area: 4,541 Sq. Ft.
- Finished Above Grnd: 4,541 Sq. Ft.
- Year Built: 1900
- Year Built Source: Assessor
Additional Structures
- Other Structures: Barn/Farm Building, Garage(s), Shed, Tenant House
Lot Features
- Lot Size (Acres): 189
- Lot Size (Sq. Ft.): 8,232,840
- Lot Size Source: Assessor
- Zoning: RPD
Water Features
- Water Front: Yes
- Navigable Water: Yes
- Water Access: Yes
- Water Access Desc: Private Access
- Water Front Type: Creek/Stream
- Water Front Name: School House Ck to St. George's Ck
Financial Considerations
- Price Per Sq. Ft.: $770.76
- Assessment Year: 2026
- County Tax: $12,868
- County Tax Freq: Annually
- Tax w/Assessment: $1,355,633
- Tax Amount: $12,868
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 4541
Disclosures and Reports
- Ownership: Fee Simple
- Multiple Parcels: Yes
Listed by Century 21 Redwood Realty, Sharon L Cox
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Schools
Schools serving 45776 Boothe Rd
School District:St. Marys County Public Schools
| Name | Grades | Distance |
|---|---|---|
Piney Point Elementary School 44550 Tall Timbers Road, Tall Timbers, MD 20690 | PK-5 | 2.6 mi |
Spring Ridge Middle School 19856 Three Notch Road, Lexington Park, MD 20653 | 6-8 | 6.4 mi |
Leonardtown High School 23995 Point Lookout Road, Leonardtown, MD 20650 | 9-12 | 10.2 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 45776 Boothe Rd
Date
Details
Price
Change
Source
8/04/2026
Listed
$3,500,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 45776 Boothe Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,827
—
$1,355,633
1%
2025
$14,827
8%
$1,340,700
4%
2023
$13,725
—
$1,289,333
4%
2023
$13,725
21%
$1,237,967
4%
2022
$11,389
29%
$1,186,600
9%
2019
$8,831
-21%
$1,090,267
10%
2021
$11,123
10%
$993,933
11%
2020
$10,097
2%
$897,600
2%
2019
$9,877
5%
$877,467
2%
2018
$9,408
2%
$857,333
2%
2017
$9,237
7%
$837,200
1%
2016
$8,644
1%
$830,167
1%
2015
$8,534
—
$822,933
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 45776 Boothe Rd
45776 Boothe Road, Drayden, MD 20630 (MLS# MDSM2032920) is a Single Family property with 3 bedrooms and 2 full bathrooms. 45776 Boothe Road is currently listed for $3,500,000 and was received on August 04, 2026. Want to learn more about 45776 Boothe Road? Do you have questions about finding other Single Family real estate for sale in Drayden? You can browse all Drayden real estate or contact a Coldwell Banker agent to request more information.

