Leonardtown, MD homes for sale & real estate

47 of 47 homes

Sort:

Recommended

View:

Photos

23075 Hollywood Rd, Leonardtown, MD 20650
23075 Hollywood Rd, Leonardtown, MD 20650
23075 Hollywood Rd, Leonardtown, MD 20650
ABOUT THIS HOME
Leonardtown, MD Homes for Sale
Built in 1942, this 5-bedroom, 2.5-bath home offers over 3,200 square feet of character-filled living space Original hardwood floors, arched openings, detailed trim work, and vintage glass door knobs are just a few of the timeless details that give this home its warmth and soul—while updates like a newer heating system, domestic hot water, roof, and refreshed bathrooms bring you everyday comfort. With natural light in all the right places highlighting the home’s spacious layout and warm, welcoming feel. A deep front porch sets the tone for quiet mornings, while the fenced backyard and two-car garage—with workshop space—add function to match the charm. And with coffe

$574,000

5 beds2.5 baths3,238 sq ft

23075 Hollywood Rd, Leonardtown, MD 20650

0.5 acre lot • 2 garage spots • Car-dependent

(301) 862-2169

COMING SOON

$843,000

5 beds4 baths4,648 sq ft

40738 Bobwhite Ln, Leonardtown, MD 20650

3.52 acre lot • $200 HOA • 2 garage spots

(301) 862-2169

COMING SOON

$479,000

3 beds3.5 baths2,645 sq ft

41326 Margrove Cir, Leonardtown, MD 20650

3,468 sq ft lot • $69 HOA • 2 garage spots

(301) 862-2169

$649,999

5 beds3.5 baths3,907 sq ft

41430 Whimsical Ct, Leonardtown, MD 20650

8,750 sq ft lot • $81 HOA • 2 garage spots

(443) 256-3773

OPEN SAT, 11AM TO 1PM

$615,000

4 beds3.5 baths3,850 sq ft

20540 Deer Wood Park Dr, Leonardtown, MD 20650

2.22 acre lot • $22 HOA • 2 garage spots

(410) 263-8686

Property at 23578 Pine Bluff Way, Leonardtown, MD 20650, 3 beds, 3.5 baths

$599,900

3 beds3.5 baths3,188 sq ft

23578 Pine Bluff Way, Leonardtown, MD 20650

(301) 862-2169

Property at 23275 Jenifer Ct, Leonardtown, MD 20650, 6 beds, 4.5 baths

$649,900

6 beds4.5 baths6,311 sq ft

23275 Jenifer Ct, Leonardtown, MD 20650

(301) 862-2169

Property at 44114 Woodmont Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$615,000

5 beds3.5 baths3,635 sq ft

44114 Woodmont Dr, Leonardtown, MD 20650

(301) 855-8600

Property at 18937 Hodges Ln, Leonardtown, MD 20650, 3 beds, 2 baths

$699,900

3 beds2 baths1,834 sq ft

18937 Hodges Ln, Leonardtown, MD 20650

(301) 609-9000

Property at 41402 Silver Charm Ct, Leonardtown, MD 20650, 5 beds, 3.5 baths

$715,000

5 beds3.5 baths4,046 sq ft

41402 Silver Charm Ct, Leonardtown, MD 20650

(301) 862-2169

Property at 40801 Kiskadee Ln, Leonardtown, MD 20650, 5 beds, 3 baths

$785,000

5 beds3 baths6,064 sq ft

40801 Kiskadee Ln, Leonardtown, MD 20650

(410) 535-6291

Property at 23730 Hicks Dr, Leonardtown, MD 20650, 3 beds, 2 baths

$425,750

3 beds2 baths1,992 sq ft

23730 Hicks Dr, Leonardtown, MD 20650

(833) 335-7433

Property at 21940 Maranatha Way, Leonardtown, MD 20650, 4 beds, 3.5 baths

$950,000

4 beds3.5 baths2,814 sq ft

21940 Maranatha Way, Leonardtown, MD 20650

(301) 684-4895

Property at 23687 Coventry Dr, Leonardtown, MD 20650, 6 beds, 4.5 baths

$700,000

6 beds4.5 baths4,650 sq ft

23687 Coventry Dr, Leonardtown, MD 20650

Property at 23266 Clarks Rest Rd, Leonardtown, MD 20650, 4 beds, 3.5 baths

$675,000

4 beds3.5 baths3,858 sq ft

23266 Clarks Rest Rd, Leonardtown, MD 20650

(301) 862-2169

Property at 23445 Grovewood Ct, Leonardtown, MD 20650, 3 beds, 3.5 baths

$444,900

3 beds3.5 baths2,379 sq ft

23445 Grovewood Ct, Leonardtown, MD 20650

(301) 862-2169

Property at 23055 Town Run Dr, Leonardtown, MD 20650, 4 beds, 3.5 baths

$699,900

4 beds3.5 baths4,019 sq ft

23055 Town Run Dr, Leonardtown, MD 20650

(443) 771-8009

Property at 40449 Breton View Dr, Leonardtown, MD 20650, 3 beds, 3.5 baths

$405,000

3 beds3.5 baths2,288 sq ft

40449 Breton View Dr, Leonardtown, MD 20650

(443) 771-8009

Property at 41505 Knight Rd, Leonardtown, MD 20650, 5 beds, 7 baths

$5,950,000

5 beds7 baths12,113 sq ft

41505 Knight Rd, Leonardtown, MD 20650

(443) 292-6767

Property at 21684 Potomac View Dr, Leonardtown, MD 20650, 3 beds, 2 baths

$490,000

3 beds2 baths1,504 sq ft

21684 Potomac View Dr, Leonardtown, MD 20650

(301) 475-8575

Property at 21897 Fairway Dr, Leonardtown, MD 20650, 5 beds, 2.5 baths

$649,000

5 beds2.5 baths3,664 sq ft

21897 Fairway Dr, Leonardtown, MD 20650

(240) 925-2224

Property at 23534 Belmar Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$669,900

5 beds3.5 baths4,738 sq ft

23534 Belmar Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 40905 Knight Rd, Leonardtown, MD 20650, 3 beds, 2.5 baths

$449,900

3 beds2.5 baths1,820 sq ft

40905 Knight Rd, Leonardtown, MD 20650

(888) 860-7369

Property at 40827 Lake And Breton View Dr, Leonardtown, MD 20650, 4 beds, 2 baths

$460,000

4 beds2 baths2,524 sq ft

40827 Lake And Breton View Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 41517 Margrove Cir, Leonardtown, MD 20650, 3 beds, 3.5 baths

$424,900

3 beds3.5 baths2,306 sq ft

41517 Margrove Cir, Leonardtown, MD 20650

(240) 925-2224

Property at 41925 Nazareth Ct, Leonardtown, MD 20650, 3 beds, 3 baths

$469,990

3 beds3 baths2,512 sq ft

41925 Nazareth Ct, Leonardtown, MD 20650

(443) 771-8009

Property at 23348 Lindsay Dr, Leonardtown, MD 20650, 5 beds, 4 baths

$635,000

5 beds4 baths3,540 sq ft

23348 Lindsay Dr, Leonardtown, MD 20650

(301) 439-9500

Property at 22362 Armstrong Dr, Leonardtown, MD 20650, 3 beds, 3 baths

$449,900

3 beds3 baths2,028 sq ft

22362 Armstrong Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 41536 Fairwood Ct, Leonardtown, MD 20650, 4 beds, 3.5 baths

$649,900

4 beds3.5 baths3,080 sq ft

41536 Fairwood Ct, Leonardtown, MD 20650

(443) 968-9595

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

(301) 472-4422

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 20959 Redgate Ln, Leonardtown, MD 20650, 3 beds, 1 bath

$375,000

3 beds1 bath1,026 sq ft

20959 Redgate Ln, Leonardtown, MD 20650

(443) 660-9229

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

$535,000

3 beds2 baths2,952 sq ft

25365 Point Lookout Rd, Leonardtown, MD 20650

(301) 862-2169

Property at 22626 Chickadee Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$650,000

4 beds3.5 baths2,948 sq ft

22626 Chickadee Ln, Leonardtown, MD 20650

(301) 684-4895

Property at 41810 Chelsey Faye Ln, Leonardtown, MD 20650, 4 beds, 3 baths

$675,000

4 beds3 baths2,650 sq ft

41810 Chelsey Faye Ln, Leonardtown, MD 20650

(301) 684-4895

Property at Wathen Rd, Leonardtown, MD 20650, 5 beds, 4 baths

$831,025

5 beds4 baths4,700 sq ft

Wathen Rd, Leonardtown, MD 20650

(240) 224-8005

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 40552 Breton Knolls Ct, Leonardtown, MD 20650, 5 beds, 2.5 baths

$884,900

5 beds2.5 baths3,127 sq ft

40552 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 41815 Chelsey Faye, Leonardtown, MD 20650

$95,000

— beds— baths— sq ft

41815 Chelsey Faye, Leonardtown, MD 20650

(301) 684-4895

Property at 40624 Breton Oaks Ln, Leonardtown, MD 20650

$180,000

— beds— baths— sq ft

40624 Breton Oaks Ln, Leonardtown, MD 20650

(301) 862-2169

Viewing page 1 of 2

Redfin agent insights on Leonardtown, MD

Leonardtown is known for its historic charm, waterfront attractions, and cultural scene. Like a scene from a Hallmark Christmas movie, Historic Downtown features boutique shops, restaurants, and nightlife. The Wharf waterfront park on Breton Bay...
4 weeks ago • Leonardtown
Farrah Fuchs
Redfin Premier agent

Average home prices near Leonardtown, MD

Cities

Lusby homes for sale
$395,000
Prince Frederick homes for sale
$447,000
Montross homes for sale
$429,950
Aquasco homes for sale
$400,000
Mechanicsville homes for sale
$497,500
Charlotte Hall homes for sale
Great Mills homes for sale
Lexington Park homes for sale
$387,000
Solomons homes for sale
$598,427
Colonial Beach homes for sale
$364,900
Cobb Island homes for sale
$364,375
Huntingtown homes for sale
$775,000
Hughesville homes for sale
$615,450
St. Leonard homes for sale
$687,500
California homes for sale
$388,625

Zip Codes

Leonardtown, MD real estate trends

All Home Types trends in Leonardtown, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$428,750

-22.8% YoY | Feb 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Feb 2025

Growth

% YoY

Leonardtown, MD

$428,750

-22.8%

See more Leonardtown, MD market insights

More to explore in Leonardtown, MD

Featured
Price
Bedroom

How to buy a house in Leonardtown, 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

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

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Become a Lender Partner

Subsidiaries

Rent.

ApartmentGuide

Bay Equity Home Loans

Title Forward

Countries

United States

Canada

Updated January 2023: 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, TITLE FORWARD, 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

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.