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

34 homes

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COMING SOON

ABOUT THIS HOME
Vintage 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
Vintage Home for sale in St. Mary's County, MD:
Welcome to 21660 N Essex Dr! With no HOA, a 2-car driveway, and a bonus detached 2-car garage, this property offers plenty of storage (in need of TLC). This home offers a total of 1,650 square feet, including 3 bedrooms and 2 full bathrooms, with a partially finished basement that is perfect for storage or future expansion. Sitting on a large, flat backyard with mature fruit trees, this property has tons of potential. Recent updates include a new roof (2023), new electric stove, and new refrigerator. The home is heated by oil and cooled with window A/C units. Flooring and paint are needed—ideal for buyers looking to add their personal touch and build equity. Located just 5 minutes fro

$240,000

3 beds2 baths1,568 sq ft

21660 N Essex Dr, Lexington Park, MD 20653

0.23 acre lot • 2 parking spots • Built 1947

(443) 771-8009

OPEN DEC 6, 10AM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in St. Mary's County, MD:
Endless Opportunities on a Historic Gem! This beautifully maintained 100+ year old home sitting on 11.82 acres, combines classic charm with modern amenities. Featuring a wrap-around porch, original craftsman staircase, 3 bedrooms, 2 baths, with fully finished attic perfect for an office. The main level bath includes jacuzzi tub and walk-in shower. Enjoy outdoor living with a new deck, in-ground pool and plenty of open space. A separate 1 bedroom 1 bath in-law suite offers rental income potential or guest accommodations-ideal for a B & B or wedding venue. Car enthusiasts will love the 5 garages/outbuildings with room for up to 12 vehicles, 1 with lift. Theres also outdoor storage and a

$725,000

3 beds2 baths2,055 sq ft

26669 Queentree Rd, Mechanicsville, MD 20659

11.83 acre lot • Pool • Built 1900

(540) 662-4500

ABOUT THIS HOME
Vintage Home for sale in St. Mary's County, MD:
Southern Maryland waterfront beach dreamhome! This stately cape-cod style cottage features 2 bedrooms, and a guest loft (easily used as a 3rd bedroom/sleeping quarter), 2 full bathrooms, an inviting open floor plan with formal dining, cozy living space, and a bright kitchen. Feel right at home the minute you walk through the door, taking in the breathtaking views from every window! Wide open, unobstructed views of the Potomac River, as well as surrounding forrest/creek. No shortage of space to entertain on the back, side and front yards, the large garage, and the perfect beach for beachdays, fishing, boating, and bonfires. Beautiful oversized detached garage with pull through bay doors, i

$598,000

3 beds2 baths1,440 sq ft

14005 Cornfield Harbor Dr, Scotland, MD 20687

Open floor plan • Large garage • Unobstructed views

(443) 968-9595

ABOUT THIS HOME
Vintage Home for sale in St. Mary's County, MD:
Discover the charm and tranquility of country living with this beautiful waterfront property offering breathtaking views of the Patuxent River and St. Thomas Creek. The open main-level floor plan of this 3BR 2FB home captures water views from most areas, as does the rear of the fully finished walkout-level basement. The spacious walk-up attic could potentially offer future expansion into a third floor—perhaps maybe with dormers—to further enhance living space and capture even more stunning panoramic views. Enjoy the outdoors from the large rear deck or take advantage of direct water access with a private pier, jet ski ramp, boat lift, pier-side storage shed, and small beach area

$599,900

3 beds2 baths3,140 sq ft

43979 Drum Cliff Rd, Hollywood, MD 20636

1.01 acre lot • 4 parking spots • Built 1945

(301) 609-9000

Property at 24984 Forrest Cove Way, Hollywood, MD 20636, 3 beds, 2 baths

$255,000

3 beds2 baths2,080 sq ft

24984 Forrest Cove Way, Hollywood, MD 20636

(571) 899-4949

Property at 41010 New Market Turner Rd, Mechanicsville, MD 20659, 3 beds, 2.5 baths

$414,900

3 beds2.5 baths1,735 sq ft

41010 New Market Turner Rd, Mechanicsville, MD 20659

(703) 378-8810

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 20798 Waterside Dr, Leonardtown, MD 20650, 2 beds, 1 bath

$450,000

2 beds1 bath1,018 sq ft

20798 Waterside Dr, Leonardtown, MD 20650

(410) 535-6291

Property at 22719 Lagoon Dr, Bushwood, MD 20618, 4 beds, 2 baths

$340,000

4 beds2 baths1,442 sq ft

22719 Lagoon Dr, Bushwood, MD 20618

(443) 975-7555

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 19717 Oak Ct, Lexington Park, MD 20653, 3 beds, 2 baths

$413,000

3 beds2 baths1,806 sq ft

19717 Oak Ct, Lexington Park, MD 20653

(855) 885-4663

Property at 22405 Indian Bridge Rd, California, MD 20619, 3 beds, 2 baths

$249,900

3 beds2 baths1,823 sq ft

22405 Indian Bridge Rd, California, MD 20619

(301) 862-4000

Property at 20436 Bowles Rd, Coltons Point, MD 20626, 2 beds, 2 baths

$355,000

2 beds2 baths896 sq ft

20436 Bowles Rd, Coltons Point, MD 20626

(443) 975-7555

Property at 20938 Olen Mattingly Rd, Avenue, MD 20609, 4 beds, 3.5 baths

$775,000

4 beds3.5 baths1,962 sq ft

20938 Olen Mattingly Rd, Avenue, MD 20609

(703) 581-8605

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 24691 Old Three Notch Rd, Hollywood, MD 20636, 3 beds, 1 bath

$335,000

3 beds1 bath3,234 sq ft

24691 Old Three Notch Rd, Hollywood, MD 20636

(301) 884-9493

Property at 47209 Lincoln Ave, Lexington Park, MD 20653, 5 beds, 2 baths

$364,000

5 beds2 baths1,456 sq ft

47209 Lincoln Ave, Lexington Park, MD 20653

(301) 445-1395

Property at 45044 Deagles Boatyard Rd, Tall Timbers, MD 20690, 4 beds, 3 baths

$419,999

4 beds3 baths2,106 sq ft

45044 Deagles Boatyard Rd, Tall Timbers, MD 20690

(301) 862-2169

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 17677 Three Notch Rd, Dameron, MD 20628, 3 beds, 2 baths

$299,000

3 beds2 baths2,614 sq ft

17677 Three Notch Rd, Dameron, MD 20628

(301) 684-4895

Property at 24313 Mervell Dean Rd, Hollywood, MD 20636, 3 beds, 1.5 baths

$369,900

3 beds1.5 baths1,626 sq ft

24313 Mervell Dean Rd, Hollywood, MD 20636

(703) 378-8810

Property at 24992 Sotterley Rd, Hollywood, MD 20636, 2 beds, 1 bath

$299,999

2 beds1 bath1,096 sq ft

24992 Sotterley Rd, Hollywood, MD 20636

(301) 862-4000

Property at 45991 Clarks Rd, California, MD 20619, 2 beds, 2 baths

$549,000

2 beds2 baths880 sq ft

45991 Clarks Rd, California, MD 20619

(410) 535-6291

Property at 19809 Point Lookout Rd, Lexington Park, MD 20653, 4 beds, 2.5 baths

$469,000

4 beds2.5 baths3,268 sq ft

19809 Point Lookout Rd, Lexington Park, MD 20653

(301) 884-9493

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 37420 River Springs Rd, Avenue, MD 20609, 2 beds, 1.5 baths

$577,000

2 beds1.5 baths2,112 sq ft

37420 River Springs Rd, Avenue, MD 20609

(301) 884-9493

Property at 25365 Point Lookout Rd, Leonardtown, MD 20650, 3 beds, 2 baths

$497,500

3 beds2 baths2,952 sq ft

25365 Point Lookout Rd, Leonardtown, MD 20650

(301) 862-2169

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 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 21744 Louden Ln, Lexington Park, MD 20653, 2 beds, 1.5 baths

$599,900

2 beds1.5 baths1,500 sq ft

21744 Louden Ln, Lexington Park, MD 20653

(540) 662-4500

$150,000

2 beds1 bath720 sq ft

18048 Trossbach Rd, Dameron, MD 20628

(301) 862-2169

Property at 39645 Sweetpea Ln, Leonardtown, MD 20650

$799,900

— beds— baths— sq ft

39645 Sweetpea Ln, Leonardtown, MD 20650

(301) 609-9000

$999,000

— beds— baths— sq ft

24699 Hollywood, Hollywood, MD 20636

(540) 374-1111

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Vintage Homes for Sale in St. Mary's County

There are currently 34 vintage 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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