Luxury homes for sale & real estate in St. Mary's County, MD

26 homes

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ABOUT THIS HOME
Luxury Home for sale in St. Mary's County, MD:
Beautiful 108-acre farm on Carroll Pond with limited access to the Chesapeake Bay. The original 1900s home has seen updates over the years and currently operates as an Airbnb (Trinity Oaks Farm). A hunter’s dream, private getaway, or ideal full-time homestead. The property includes 42 acres of forest, 33 acres of fields with 3 paddocks (with water and electric), and 32 acres of marsh and pond. Enjoy two ponds, wooded trails, abundant wildlife, and fenced areas for animals. The land is enrolled in a Preservation & Forestry Stewardship Plan. Several outbuildings provide additional utility. Kayak from the pond out to the bay and take in the peaceful, secluded setting. Cable has rec

$1,050,000

4 beds2.5 baths2,214 sq ft

49465 Demko Rd, Lexington Park, MD 20653

108.84 acre lot • 10 parking spots • Built 1900

(301) 862-2169

ABOUT THIS HOME
Luxury Home for sale in St. Mary's County, MD:
Welcome to your waterfront sanctuary and entertainers dream home! The custom craftmanship in this home will amaze you. This 4 bedroom 2 1/2 bathroom home has everything at your fingertips. Family room w/ fireplace and exposed beams. Built in bar and entertainment space off family room and kitchen. Large gourmet kitchen and formal dining room. Upper level with primary bedroom and primary bathroom. 3 additional bedrooms and a full bathroom. The detached garage has a loft style apartment with kitchen and full bathroom. Pier with both stair and path access . Sailboat depth with 6' MLW. Close to area amenities and access to Route 235. Schedule your online appointment today.

$1,200,000

4 beds2.5 baths2,671 sq ft

25890 Whiskey Creek Rd, Hollywood, MD 20636

1.07 acre lot • 2 garage spots • Built 2002

(301) 862-2169

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in St. Mary's County, MD:
Welcome to a luxuriously crafted waterfront home where design and comfort meet the tranquility of coastal living. Perfectly positioned to capture sweeping views of Cuckold Creek, this residence showcases exceptional finishes and attention to detail throughout. The Hardie board exterior, accented by lush landscaping and a charming gazebo overlooking the shoreline and pier, evokes a timeless Dutch Colonial aesthetic with modern coastal flair. Step inside and experience luxury and scenic water views at every turn — from the stunning owner’s suite to the showstopping kitchen featuring top-of-the-line appliances, including a Miele coffee system, and beautifully detailed cabinetry. Th

$1,675,000

3 beds3.5 baths4,241 sq ft

44850 Joy Chapel Rd, Hollywood, MD 20636

0.58 acre lot • Garage • Built 1973

(240) 925-2224

ABOUT THIS HOME
Luxury Home for sale in St. Mary's County, MD:
Bella Vista on the Patuxent River – An Elevated Waterfront Retreat Nestled on the banks of the Patuxent River in Esperanza Farms, Bella Vista is a five-bedroom, five-and-a-half-bath waterfront retreat where intentional design meets resort-style living. Every detail has been reimagined—interior renovation in 2023 and exterior transformation in 2024—to create a home that inspires awe, comfort, and connection. Inside, elegant craftsmanship defines each room: four spa-inspired primary suites, including one with a fireplace and coffee bar with sink and beverage refrigerator. The chef’s kitchen features a gas fireplace, high-end appliances, and generous workspace that flo

$2,975,000

5 beds5.5 baths5,003 sq ft

23396 Esperanza Cir, Lexington Park, MD 20653

1.25 acre lot • 2 garage spots • Pool

(301) 862-2169

ABOUT THIS HOME
Luxury Home for sale in St. Mary's County, MD:
Charming rustic 4-bedroom home on 14.31 acres in Mechanicsville. Interior includes 2 full baths, 2 half baths, all Amish-built cabinetry, an upper-level rec room, and 2 pellet stoves for added warmth and comfort. Enjoy outdoor living from the wrap-around porch overlooking the property. Exterior highlights feature a pool barn with —complete with a wood-burning stove—a new 30x40 pole barn with 10ftx40ft overhang, chicken coop with feed barn, walk-in freezer box, private trails, hunting opportunities, and a pool for summer enjoyment. Recent updates include a well pump less than 1 month old and a sewage pump less than 1 year old. This rustic property offers exceptional space, functi

$950,000

4 beds3 baths3,133 sq ft

26000 Sycamore Dr, Mechanicsville, MD 20659

Pellet stoves • Upper-level rec room • Wood-burning stove

(301) 862-2169

Property at 38888 Reeves Rd, Mechanicsville, MD 20659, 4 beds, 2.5 baths

$1,250,000

4 beds2.5 baths1,896 sq ft

38888 Reeves Rd, Mechanicsville, MD 20659

(301) 439-9500

Property at 18688 Hebb Rd, Valley Lee, MD 0, 5 beds, 3.5 baths

$859,900

5 beds3.5 baths3,127 sq ft

18688 Hebb Rd, Valley Lee, MD 0

(301) 843-5100

Property at 17203 Piney Point Rd, Piney Point, MD 20674, 6 beds, 3 baths

$874,900

6 beds3 baths2,683 sq ft

17203 Piney Point Rd, Piney Point, MD 20674

(202) 506-3674

Property at 23395 Esperanza Cir, Lexington Park, MD 20653, 5 beds, 3 baths

$899,000

5 beds3 baths2,483 sq ft

23395 Esperanza Cir, Lexington Park, MD 20653

(301) 862-2169

Property at 24754 Half Pone Point Rd, Hollywood, MD 20636, 5 beds, 5 baths

$1,650,000

5 beds5 baths4,857 sq ft

24754 Half Pone Point Rd, Hollywood, MD 20636

(301) 862-2169

Property at 16460 Sayre Point Ln, Piney Point, MD 20674, 4 beds, 2 baths

$875,000

4 beds2 baths2,322 sq ft

16460 Sayre Point Ln, Piney Point, MD 20674

(301) 862-2169

Property at 49716 Airedele Rd, Ridge, MD 20680, 6 beds, 3 baths

$864,998

6 beds3 baths4,000 sq ft

49716 Airedele Rd, Ridge, MD 20680

(888) 860-7369

Property at 19700 Mulberry Fields Rd, Leonardtown, MD 20650, 6 beds, 4.5 baths

$20,000,000

6 beds4.5 baths13,458 sq ft

19700 Mulberry Fields Rd, Leonardtown, MD 20650

(202) 483-6300

Property at 21210 Bernie Lawrence Ln, Abell, MD 20606, 4 beds, 4 baths

$899,900

4 beds4 baths2,544 sq ft

21210 Bernie Lawrence Ln, Abell, MD 20606

(301) 884-7000

Property at 44605 Old St. Andrew's Church Rd, California, MD 20619, 5 beds, 7 baths

$995,000

5 beds7 baths8,640 sq ft

44605 Old St. Andrew's Church Rd, California, MD 20619

(301) 862-2169

Property at Undisclosed address, Leonardtown, MD 20650, 4 beds, 2 baths

$1,750,000

4 beds2 baths2,130 sq ft

Undisclosed address, Leonardtown, MD 20650

(301) 686-0545

Property at 14623 C Way Dr, Scotland, MD 20687, 3 beds, 3 baths

$925,000

3 beds3 baths2,304 sq ft

14623 C Way Dr, Scotland, MD 20687

(571) 814-3002

Property at 37201 Gibson Rd, Bushwood, MD 20618, 4 beds, 2 baths

$2,950,000

4 beds2 baths2,349 sq ft

37201 Gibson Rd, Bushwood, MD 20618

(202) 234-3344

Property at 23794, 23790 Saint Clair Rd, California, MD 20619, 6 beds, 5.5 baths

$1,070,000

6 beds5.5 baths3,170 sq ft

23794, 23790 Saint Clair Rd, California, MD 20619

(240) 630-8689

Property at 40533 Breton Knolls Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$859,900

4 beds2.5 baths— sq ft

40533 Breton Knolls Ct, Leonardtown, MD 20650

(301) 843-5100

Property at 42520 Riverwinds Dr, Leonardtown, MD 20650, 4 beds, 2 baths

$1,999,999

4 beds2 baths2,744 sq ft

42520 Riverwinds Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 45410 Clarks Mill Rd, Hollywood, MD 20636

$899,000

— beds— baths— sq ft

45410 Clarks Mill Rd, Hollywood, MD 20636

(540) 374-1111

Property at Parcel 331 & 332, Willows Rd, Lexington Park, MD 20653

$2,895,000

— beds— baths— sq ft

Parcel 331 & 332, Willows Rd, Lexington Park, MD 20653

(410) 821-8585

Property at Three Notch Rd, Lexington Park, MD 20653

$4,500,000

— beds— baths— sq ft

Three Notch Rd, Lexington Park, MD 20653

(301) 870-5841

Property at 44405-5 LOTS K & R Way, Hollywood, MD 20636

$1,300,000

— beds— baths— sq ft

44405-5 LOTS K & R Way, Hollywood, MD 20636

(443) 771-8009

$999,000

— beds— baths— sq ft

24699 Hollywood, Hollywood, MD 20636

(540) 374-1111

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Luxury Homes for Sale in St. Mary's County

There are currently 26 luxury homes for sale in St. Mary's County at a median listing price of $465K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in St. Mary's County stay on the market for 49 days and receive 2 offers. This map is refreshed with the newest listings in St. Mary's County every 15 minutes.

In the past month, 133 homes have been sold in St. Mary's County. In addition to houses in St. Mary's County, there were also 17 condos, 54 townhouses, and 2 multi-family units for sale in St. Mary's County last month. Find your dream home in St. Mary's County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in St. Mary's County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in St. Mary's County. If you're looking to sell your home in the St. Mary's County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in St. Mary's County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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