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$3,500,000
3 Beds ⋅ 2 Baths
Welcome to a rare opportunity to acquire one of Southern Maryland's truly exceptional waterfront estates. Steeped in history that dates back to the mid-19th century, this remarkable property, historically known as Timerity Farm (also referred to as Westbury Farm), encompasses approximately 189 acres of farmland, mature woodland, and protected waterfront along School House Branch, with direct access to St. George Creek and the Potomac River. With approximately 5,000 linear feet of protected shoreline (GIS-derived estimate), the property offers an extraordinary combination of privacy, agricultural productivity, abundant wildlife, recreational boating, and timeless Chesapeake Bay character. The historic manor house is a charming one-and-one-half-story frame residence believed to date from the mid-1800s. The home retains much of its historic character, retaining rare historic pent chimneys, an increasingly uncommon architactural feature in Maryland. Designed on a traditional side-passage/double-parlor floor plan, the home features separate living and dining rooms, each with its own fireplace, hardwood flooring, and period painted moldings. The residence offers 3 bedrooms, including one on the main level and 2 upstairs along with two full bathrooms. The country kitchen adjoins a generous gathering area ideal for entertaining family and friends. A covered side porch overlooks the waterfront and provides the perfect setting for crab feasts, relaxing evenings, or simply enjoying the peaceful views across School House Branch. The private pier serving the residence extends into protected waters with an estimated water depth of approximately five feet at Mean Low Water (MLW) based upon available GIS mapping and aerial analysis, providing convenient access for a variety of recreational boats. The productive farmland is currently leased to a local farmer, providing agricultural income while preserving the property's rural heritage. In addition to the main residence, the property includes three cottages and four barns/outbuildings, offering numerous possibilities for agricultural operations, guest accommodations, storage, workshops, or future restoration. According to St. Mary's County Planning and Zoning, all Transferable Development Rights (TDRs) remain available and have not been exercised, presenting an important opportunity for future planning. Whether envisioned as a private family estate, working farm, sporting property, equestrian retreat, or waterfront sanctuary, this extraordinary offering combines historic significance, productive farmland, protected boating waters, and exceptional natural beauty into one remarkable Chesapeake Bay property. The protected waters of School House Branch provide easy access to St. George Creek and the Potomac River while offering a sheltered location for boating, fishing, kayaking, and paddleboarding. Disclaimer: Acreage is approximate. Shoreline footage (approximately 5,000 linear feet) and water depth at the pier (approximately 5 feet MLW) are estimates derived from publicly available GIS mapping, aerial imagery, and related public information and are not based on a boundary or hydrographic survey. Buyers should independently verify all measurements, water depths, development rights, zoning, and other material information to their satisfaction.

45776 Boothe Rd, Drayden

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279
$799,000
5 Beds ⋅ 3 Baths
Welcome to Hickory Landing Waterfront property. The tree-filled private and quiet 17+ acre property is located on a cove off of Cuckold Creek. Experience breathtaking views from both the living room and the upper level, offering a perfect backdrop for daily living and relaxation. Chef's kitchen features custom solid maple painted cabinets, providing timeless elegance and ample storage space for the discerning cook. This property was built in 1983 and expanded in 1990. This is a rare parcel of land offering privacy and natural beauty. The home has views of the water and abundant wildlife. The 17+ acres and house are on mostly level land, the rest of the land is wooded with walnut, poplar,oak, maple and cypress trees which you can view down the long driveway to the house. There is a pier on the property that is private for the neighbors use. There is 1 boat slip open. This water is good for a pontoon boat , Canoe, shallow drafted boats. The pier is being redone in August 2026. The home is approximately 2,727Sq.Ft. with 5 bedrooms and 3 baths. 2 outbuildings. NO HOA. Text listing agent for more information.

44908 Hickory Landing Way, Hollywood

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4103940990
$79,000
2 Beds ⋅ 1 Baths
Fantastic opportunity to purchase this charming single‑wide mobile home in the picturesque Langley Mobile Home Park on the St. Mary’s River. Features hardwood floors, a custom kitchen, 2 bedrooms, and a custom‑tiled full bath. Lot rent is $700 per month.

45813 Langley Park Way Unit #22, Lexington Park

Listing courtesy of Taylor Properties. Contact:

$430,000
4 Beds ⋅ 3 Baths
***Just 10 minutes away from Pax River Naval Base*** This property offers an effortless commute for military, contractors, and buyers looking for an easy commute. This almost new, built in 2025, townhouse comes packed with modern upgrades. Designed for premium comfort, the main level features built-in, in-ceiling speakers for seamless whole-house audio, a gorgeous designer kitchen complete with stainless steel appliances, and an EV charger in the garage. Walk right out to your private, screened deck; the perfect, insect-free spot to unwind or host a weekend gathering.Peace of mind comes standard with a fully integrated security system already in place. Tucked away in a quiet Great Mills pocket, this hidden gem keeps you close to local schools, neighborhood dining, and daily conveniences. Upgrade your lifestyle and your daily commute with this turn-key, like-new home. Schedule your tour today.

22503 E Maxine Way, Great Mills

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636
$1,450,000
1 Beds ⋅ 1 Baths
A rare opportunity to own an extraordinary 11.83-acre wooded property in the prestigious Half Pone Point community. Located directly across from the spectacular waterfront estate at 24730 Half Pone Point Rd, this versatile property offers endless possibilities for a private family compound, car collector, hobbyist, business owner, or recreational enthusiast. The property is improved with five buildings, including two stick-built structures, one featuring a second-floor one-bedroom, one-bath apartment with beautiful water views. Two metal buildings and an impressive airplane hangar-style garage with two oversized roll-up doors provide exceptional space for vehicle collections, RVs, boats, equipment, workshops, or storage. An additional A-frame building adds even more flexibility. Designed for convenience and functionality, the property features multiple 60-amp RV hookups, along with plumbing and electric throughout the buildings, making it ideal for a variety of residential, recreational, or commercial-style uses. This property is exceptional on its own, but when assembled with the waterfront estate across the street, it creates one of Southern Maryland's most remarkable legacy properties. Whether you're seeking privacy, expansive acreage, unmatched storage, or the opportunity to create a one-of-a-kind estate, this offering is truly unlike any other.

24715 Half Pone Point Rd, Hollywood

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$250,000
2 Beds ⋅ 2 Baths
Opportunity awaits on this beautiful 3.05-acre parcel tucked away on a quiet paved road in the heart of Callaway. Whether you're looking for a renovation project, a homesite to build your dream home or an investment property, this property offers incredible potential with existing infrastructure already in place. The current mobile home is in need of significant renovation or removal, making way for a fresh start on a spacious and private lot surrounded by mature trees. Existing improvements include a detached 16' x 18' garage with 100-amp electric service, an existing well and septic system, and a circular driveway for easy access and ample parking. Enjoy the convenience of a prime location just minutes from shopping, restaurants, schools, and Patuxent River Naval Air Station, while still enjoying the peace and privacy of country living.

20275 Jackson Rd, Callaway

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$279,000
3 Beds ⋅ 2 Baths
4 acres w/ trailer, trailer sold AS-IS. Possible 3 additional buildable lots - all percs approved.

48683 Beachville Rd, Saint Inigoes

Listing courtesy of RE/MAX One. Contact: 4437718009
$950,000
5 Beds ⋅ 4 Baths
Tucked away on 1.39 private acres with approximately 530 feet of waterfront, this exceptional retreat offers sweeping water views, spectacular sunsets, and direct access just around the bend from the Potomac River. A rare opportunity for boating enthusiasts, the property features a substantial pier with multiple deep-water slips, boat lift, electric, and excellent crabbing and fishing right from your backyard. The spacious home offers over 4,700 square feet with 5 bedrooms and 4 full baths, including multiple main-level bedrooms and flexible living spaces designed to capture the waterfront setting. Large windows frame serene water views throughout, while expansive indoor and outdoor entertaining areas create the perfect setting for gatherings, weekend escapes, or full-time waterfront living. Originally built in 1974 the property includes a waterside workshop/boathouse, generous parking, and beautifully maintained grounds with mature trees and a gently sloping lawn to the water’s edge. Whether you are looking for a peaceful private residence, a weekend retreat, or the ultimate boating lifestyle, this Southern Maryland waterfront property delivers an unmatched setting

20535 Golden Thompson Rd, Avenue

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169
$285,000
3 Beds ⋅ 4 Baths
Welcome to 22424 Greenview Ct in Great Mills—an updated and well-maintained home offering comfort, space, and convenience. This property features 3 bedrooms, 2 full bathrooms, and 2 half bathrooms, providing a functional layout for everyday living. Enjoy a fully finished walk-up basement that offers versatile use—ideal for extra storage, office, recreation space, or a large guest bedroom with an attached half bath. The home showcases a combination of LVP, laminate, and hardwood flooring, creating a clean, modern feel and easy maintenance. Step outside to a power-washed deck and a fully fenced backyard—perfect for relaxing, entertaining, or pets. Brand new water heater (May 2026). The property also includes 2 assigned parking spaces for added convenience. Located just minutes from Naval Air Station Patuxent River, shopping, dining, and everyday essentials, this home offers both accessibility and comfort.

22424 Greenview Ct, Great Mills

Listing courtesy of JPAR Real Estate Professionals. Contact: 3016844895
$100,000
Rare opportunity in the highly desirable 7th District of St. Mary’s County! This unique offering includes three separate waterfront lots totaling approximately 1.5 acres. Each lot currently contains existing structures that are in dilapidated condition and are likely tear-downs, offering a blank slate for buyers with vision. With its scenic waterfront setting and location in one of the county’s most sought-after areas, this property provides a rare chance to create something special. Buyer to perform all due diligence regarding zoning, permitting, building feasibility, septic/well requirements, and intended use of the property. Property is being sold strictly as-is. Opportunities like this in the 7th District do not come along often, bring your ideas and explore the possibilities this waterfront property has to offer!

20910 Olen Mattingly Rd, Avenue

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636
$115,000
3 Beds ⋅ 2 Baths
The value is in the land. 1.36 Acres in a rural setting with onsite utilities (private well & septic, electric). The property boasts a level lot with mature trees. Live in the mobile home while you begin the process of building your dream home. Or continue to use the mobile home, currently under a month to month lease, as income potential. *Note: Government backed loans may not support purchase of the mobile home as a residence.

40412 Medleys Ln, Mechanicsville

Listing courtesy of Coldwell Banker Premier. Contact: 5406624500