Vintage homes for sale & real estate in 20650, MD

9 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in 20650, MD:
Welcome Home! This charming rambler offers approximately 1,200 square feet of comfortable one-level living situated on a level 0.60-acre lot. A covered front porch provides a welcoming entry, while inside, the home has a practical floor plan with new flooring throughout and new kitchen appliances. Outside, enjoy the deck for relaxing or entertaining. With no HOA, you’ll appreciate the added flexibility of homeownership without monthly association dues. Conveniently located near historic downtown Leonardtown and just a short commute to Naval Air Station Patuxent River. Schedule your private tour today!

$325,000

3 beds1.5 baths1,218 sq ft

42163 Blacksmith Shop Rd, Leonardtown, MD 20650

Covered front porch • Deck for relaxing • New flooring

(301) 862-2169

ABOUT THIS HOME
Vintage Home for sale in 20650, MD:
Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year. Perfectly positioned to capture breathtaking water views, this exceptional property offers a rare opportunity to own a private waterfront oasis with an expansive shoreline along both Breton Bay and Combs Creek, extending all the way to the point of its sandy beach peninsula. Enhanced riprap protection, extensive landscaping, and mature surroundings create a truly unforgettable setting. E

$1,590,000

5 beds3.5 baths2,993 sq ft

40115 Combs Creek Way, Leonardtown, MD 20650

Saltwater pool • Panoramic views • Expansive shoreline

(301) 862-2169

ABOUT THIS HOME
Vintage Home for sale in 20650, MD:
This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal retreat. Nestled on the serene shores of McKays Cove, several major exterior capital improvements are already complete. The structure features a brand-new Amish-built roof, new gutters, and premium new Andersen windows throughout. Personal Boat Ramp: Private ramp for seamless watercraft launching and only one in the community. Private Pier: Sturdy, deep-water access steps from your back door. New Rip Rap: Fresh shoreline reinforcement ensures long-term erosion protection. Large propane tank which is almost full for newly installed gas log fireplace & furnace. All supporting floor beams in the crawl

$465,000

3 beds2 baths1,667 sq ft

18800 Mckays Beach Rd, Leonardtown, MD 20650

New rip rap • Private ramp • Private pier

(443) 295-6123

ABOUT THIS HOME
Vintage Home for sale in 20650, MD:
Fully renovated. Move-in ready. Prime downtown location. Welcome to 41620 Church St — a rare opportunity to own a completely updated home in the heart of Leonardtown at an exceptional value. Step inside to discover brand new vinyl flooring throughout, a stunning kitchen featuring quartz countertops, and beautifully refreshed bathrooms that bring a modern, clean aesthetic to every corner of the home. Outside, enjoy a fully fenced yard surrounding the property — perfect for pets, gatherings, or private outdoor living. The detached two-car garage adds both convenience and versatility, offering space for vehicles, storage, or even a workshop. All the hard work has been done —

$399,000

3 beds2 baths1,728 sq ft

41620 Church St, Leonardtown, MD 20650

6,534 sq ft lot • 2 garage spots • Built 1940

(301) 840-8061

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in 20650, MD:
OPEN HOUSES BY APPOINTMENT. PLEASE COME AND TAKE A LOOK AT THIS MAGNIFICENT 500 ACRE ESTATE WHERE THE FOUNDING FATHER'S ONCE MINGLED! Mulberry Fields is one of those rare places where the land itself tells the story. The mile-long cedar avenue announces the approach, its rows planted at an ever-widening angle to draw the eye toward the Potomac below, a feat of 18th-century landscape design so precise it has appeared in gardening textbooks for centuries. At the end of that drive stands the last surviving Georgian manor house in St. Mary’s County, a ca. 1755 brick estate where the center hall, great room, and dining room are paneled in raised wood from floor to ceiling, the original mol

$15,000,000

6 beds4.5 baths5,500 sq ft

19700 Mulberry Fields Rd, Leonardtown, MD 20650

Kitchen garden • Georgian manor house • Mile long view

(202) 483-6300

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 Bayside Rd, Leonardtown, MD 20650, 4 beds, 2 baths

$1,750,000

4 beds2 baths2,130 sq ft

Bayside Rd, Leonardtown, MD 20650

(301) 686-0545

Property at 42700 Moll Dyer Rd, Leonardtown, MD 20650

$290,000

Land15.00 acres (lot)

42700 Moll Dyer Rd, Leonardtown, MD 20650

(301) 645-1700

Property at 39645 Sweetpea Ln, Leonardtown, MD 20650

$799,900

Land3.56 acres (lot)

39645 Sweetpea Ln, Leonardtown, MD 20650

(301) 609-9000

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

ABOUT THIS HOME
Vintage Home for sale in 20650, MD:
Escape to your own private waterfront retreat! Stunning panoramic views of the Patuxent River will greet you each day at this hilltop property where the water is visible from almost every window. Aptly named "Turtle Watch, " this almost 2-acre slice of serenity is tucked away from the hustle and bustle of daily life. With great spaces for entertaining or quiet contemplation, this desirable location is perfect for large gatherings, or intimate getaways. It's a unique spot to make memories and live life on the water, whether you're in residence year-round, or enjoying occasional weekends. The 350+ feet of water frontage feature deep, protected water on St Thomas Creek, just a stone'

$825,000

2 beds2 baths1,783 sq ft

44015 Drum Cliff Rd, Hollywood, MD 20636

Water frontage • Ipe wood decking • Panoramic views

(301) 862-2169

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 20650, MD:
Welcome home to 24861 Three Notch Road! This beautifully updated rambler offers seamless one-level living, modern upgrades, and the perfect blend of convenience and country charm. Step inside to discover a bright and inviting layout featuring a fully renovated kitchen equipped with updated cabinetry, sleek countertops, and modern finishes—ideal for daily living and entertaining. The functional floor plan includes three bedrooms and an updated full bathroom. Outside, enjoy the expansive 1-acre lot offering endless space for outdoor activities, gardening, or relaxing in your own private sanctuary. Unbeatably located in Hollywood, MD, you are just minutes from NAS Patuxent River, local s

$330,000

3 beds1 bath1,170 sq ft

24861 Three Notch Rd, Hollywood, MD 20636

Private sanctuary • Expansive 1 acre lot • 1 acre lot

(410) 286-1496

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in 20650, MD:
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. T

$3,500,000

3 beds2 baths4,541 sq ft

45776 Boothe Rd, Drayden, MD 20630

Waterfront estate • Private pier • Productive farmland

(301) 208-2288

ABOUT THIS HOME
Vintage Home for sale in 20650, VA:
RENOVATED WATERVIEW RIVER COTTAGE WITH ADDITIONAL LOT! VERY CLOSE TO MARINAS AND COLES POINT TAVERN. GREAT PLACE TO ENJOY THE POTOMAC RIVER AND GRAB A GREAT MEAL. HOME HAS REFINISHED PINE FLOORS, NEW APPLIANCES, 3 NEW MINI-SPLITS, NEW KITCHEN & BATHROOM FLOORS, FRESHLY PAINTED INTERIOR, NEW FRONT PORCH, NEW WIRING, GAS LOGS, NEW LIGHTS AND FANS, NEW WINDOWS, COMPLETE OVERHAUL OF HOME. HOME HAS NEWER METAL ROOF. FRONT PORCH IS A FANTASTIC PLACE TO ENJOY THE POTOMAC RIVER VIEWS!

$289,000

3 beds1 bath993 sq ft

809 Salisbury Park Rd, Hague, VA 22469

New kitchen • Close to marinas • Additional lot

(804) 436-1150

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 20650, MD:
Welcome to Mount Olive Farm! A breathtaking 39-acre horse farm featuring a beautifully restored manor home originally built in 1880. Rich in history and thoughtfully updated over the years, this exceptional estate seamlessly blends timeless character with modern amenities. The home features a stunning gourmet kitchen addition equipped with a commercial-grade range, Viking double ovens, a wood-burning fireplace, and French doors leading to a spacious 30' x 20' screened porch overlooking the picturesque farm. Additional living spaces include a library, private office, art studio, family room, sitting room, and an inviting grand front porch. Hardwood and brick flooring add warmth and charm thr

$2,250,000

4 beds3 baths4,228 sq ft

45433 Drayden Rd, Valley Lee, MD 20692

Private office • 39 acre horse farm • Screened porch

(301) 208-2288

ABOUT THIS HOME
Vintage Home for sale in 20650, MD:
PRICE ENHANCEMENT! Step into this ONE level, completely renovated home that was stripped down to the studs and everything was replaced from the roof to the floor, new well, and connected to public sewer in 2022. Expand without having to worry about where the septic or septic reserve area is. See and feel the craftsmanship that was put in with wood flooring, stainless appliances, sought after barn type door bedroom closets, Primary step in glass/tile shower, and tiled secondary bath. This is like getting a brand new home at a secondary home price. All of this so close to Leonardtown, the hospital, schools, and shopping. See it today!

$419,000

3 beds2 baths1,632 sq ft

23898 Speith Rd, Leonardtown, MD 20650

Wood flooring • New well • Public sewer

(443) 771-8009

Property at 25263 Sotterley Rd, Hollywood, MD 20636, 3 beds, 1.5 baths

$334,000

3 beds1.5 baths1,274 sq ft

25263 Sotterley Rd, Hollywood, MD 20636

(855) 885-4663

Property at 43732 Raspberry Ln, Hollywood, MD 20636, 2 beds, 2 baths

$598,000

2 beds2 baths1,226 sq ft

43732 Raspberry Ln, Hollywood, MD 20636

(571) 386-1075

Property at 24040 Hollywood Rd, Hollywood, MD 20636, 3 beds, 1 bath

$335,000

3 beds1 bath1,000 sq ft

24040 Hollywood Rd, Hollywood, MD 20636

(301) 645-1700

Property at 38819 Morris Point Rd, Abell, MD 20606, 3 beds, 2 baths

$559,900

3 beds2 baths1,800 sq ft

38819 Morris Point Rd, Abell, MD 20606

(443) 771-8009

Property at 43979 Drum Cliff Rd, Hollywood, MD 20636, 2 beds, 2 baths

$499,900

2 beds2 baths3,140 sq ft

43979 Drum Cliff Rd, Hollywood, MD 20636

(301) 609-9000

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 24699 Hollywood, Hollywood, MD 20636

$999,000

Land8.00 acres (lot)

24699 Hollywood, Hollywood, MD 20636

(540) 374-1111

Vintage Homes for Sale in 20650

There are currently 9 vintage homes for sale in 20650 at a median listing price of $590K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 20650 stay on the market for 34 days and receive 1 offers. This map is refreshed with the newest listings in 20650 every 15 minutes.

In the past month, 14 homes have been sold in 20650. In addition to houses in 20650, there was also 1 condo, 8 townhouses, and 0 multi-family units for sale in 20650 last month. Find your dream home in 20650 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 20650 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 20650. If you're looking to sell your home in the 20650 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 20650 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for 20650, MD

Nearby Zip Codes

Cities

Nearby Zip Codes with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in 20650, MD

How to buy a house in 20650, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

6 Redfin agents serving 20650

155

Deals*

4.7

Satisfaction

1280

Homes closed*

* Data from the last year

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.