$450,000
$50K PRICE DROP
- 2 Beds
- 1 Bath
- 1,018 Sq Ft
20798 Waterside Dr, Leonardtown, MD 20650
Connie Fitzgerald
RE/MAX One
6,720
Leonardtown, MD Homes
-
20798 Waterside Dr, Leonardtown, MD 20650
-
Call for Price
- 2 Beds
44980 Hamptons Blvd, Leonardtown, MD 20650
44980 Hamptons Blvd, Leonardtown, MD 20650The Newest Apartment Community Serving Pax River. Luxury apartment homes in Leonardtown, MD. A Gated Community within walking distance to the town square, which features many restaurants, shops, entertainment venues and the Wharf Waterfront. Short drive to NAVAIR - Pax River Naval Air Station. 2 and 3 bedroom apartments...all with 2 bathrooms, gourmet kitchens, FREE CLIMATE CONTROLLED STORAGE
The Hamptons at Leonardtown
-
$655,000
Sold Apr 24, 202641497 Affirmed Way, Leonardtown, MD 20650
- 5 Beds
- 3.5 Baths
- 3,934 Sq Ft
- Built 2008
Last Sold Summary
- $166/SF
- 2 Days On Market
Current Estimated Value $653,952
Last Listing Agent Heather Foster RE/MAX One
41497 Affirmed Way, Leonardtown, MD 20650 -
Est $721,725
Not Listed For Sale21385 Fairwood Ct, Leonardtown, MD 20650
- 4 Beds
- 4 Baths
- 3,970 Sq Ft
- Built 2011
Last Sold Summary
- 24 Days On Market
Last Listing Agent Dawn Bell RE/MAX One
-
$650,000
$30K PRICE DROP Under Contract- 2 Beds
- 2.5 Baths
- 2,040 Sq Ft
40461 Old Breton Beach Rd, Leonardtown, MD 20650
40461 Old Breton Beach Rd, Leonardtown, MD 20650
Billy Rabbitt
The Southside Group Real Estate
-
$2,250 Per Month
- 3 Beds
- 2.5 Baths
- 1,684 Sq Ft
- House for Rent
21113 Arbor Ct, Leonardtown, MD 20650
21113 Arbor Ct, Leonardtown, MD 20650Welcome home to this beautiful 3-bedroom, 2.5-bath residence, ideally nestled just off Route 5 in a quiet, convenient location. Enjoy easy access to local schools, shopping, dining, and historic downtown Leonardtown while still benefiting from the privacy and comfort of a peaceful neighborhood.This spacious home features generous living areas, an attached two-car garage, and a private
Roland Mellies O'Brien Realty ERA Powered
-
$1,100,000
Sold May 15, 202620045 Tower Hill Rd, Leonardtown, MD 20650
- 5 Beds
- 7 Baths
- 7,376 Sq Ft
- Built 1973
Last Sold Summary
- 24% Below List Price
- $149/SF
- 12 Days On Market
Current Estimated Value $1,141,458
Last Listing Agent Barbara Stellway KW Metro Center
20045 Tower Hill Rd, Leonardtown, MD 20650 -
Not Listed For Sale
23664 Dragonfly Ln, Leonardtown, MD 20650
- 4 Beds
- 3.5 Baths
Last Sold Summary
- 0 Days On Market
Last Listing Agent Laura Lee Hefley RE/MAX One
-
$635,000
$15K PRICE DROP- 5 Beds
- 2.5 Baths
- 2,601 Sq Ft
40751 Merlin Way, Leonardtown, MD 20650
40751 Merlin Way, Leonardtown, MD 20650
Tracy Trammell
Metro City Realty
-
$4,000
Total Monthly Price
- 4 Beds
- 4 Baths
- 4,488 Sq Ft
- House for Rent
19968 Tower Hill Rd, Leonardtown, MD 20650
19968 Tower Hill Rd, Leonardtown, MD 20650Feel like you're vacationing every day in this gorgeous house in the serene woods with magnificent lake views from every room. As you step inside this 4500 sq foot house, you'll immediately fall in love with the soaring ceilings and the incredible views. The large windows allow natural light to flood in, and provide daily views of bald eagles, great blue herons, beavers, river otters, foxes,
-
$731,084
Sold Dec 04, 202540744 Fawns Rest Way, Leonardtown, MD 20650
- 4 Beds
- 3 Baths
- 3,313 Sq Ft
- Built 2025
Last Sold Summary
- $221/SF
- 0 Days On Market
Last Listing Agent Laura Lee Hefley RE/MAX One
40744 Fawns Rest Way, Leonardtown, MD 20650 -
Est $604,289
Not Listed For Sale23650 Rocky Ridge Ct, Leonardtown, MD 20650
- 4 Beds
- 3.5 Baths
- 3,914 Sq Ft
- Built 1993
Last Sold Summary
- 20 Days On Market
Last Listing Agent Joseph Hawkins Hawkins Real Estate Company
-
$449,900
New Construction Open Sat 11:30AM - 3:30PM- 4 Beds
- 3.5 Baths
- 2,604 Sq Ft
Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650Laura Lee Hefley RE/MAX One
-
$1,650 Per Month
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
- House for Rent
39725 Lady Baltimore Ave Unit 1, Leonardtown, MD 20650
39725 Lady Baltimore Ave Unit 1, Leonardtown, MD 20650Fully Renovated 2-Bedroom Rental Available Now – Leonardtown, MD. $1650 monthly.Beautifully renovated 2-bedroom, 1-bathroom rental featuring convenient, single-level living. This unit is completely separate from the other rental unit and has its own private entrance.Property features:• Two bedrooms and one bathroom• Fully renovated throughout• All rooms located on one
Thomas Pilkerton Real Broker, LLC
-
$961,000
Sold May 28, 202640003 Tippit Rd, Leonardtown, MD 20650
- 3 Beds
- 3 Baths
- 2,490 Sq Ft
- Built 1900
Last Sold Summary
- 3% Below List Price
- $386/SF
- 23 Days On Market
Current Estimated Value $930,561
Last Listing Agent Charlotte Long EXP Realty, LLC
40003 Tippit Rd, Leonardtown, MD 20650 -
Est $529,172
Not Listed For Sale21158 Marigold St, Leonardtown, MD 20650
- 4 Beds
- 2.5 Baths
- 2,649 Sq Ft
- Built 2001
Last Sold Summary
- 6 Days On Market
Last Listing Agent Jarred Green Real Broker, LLC
-
$449,900
New Construction Pending- 4 Beds
- 3.5 Baths
- 2,604 Sq Ft
Lot 144 - 23635 Dragonfly Ln, Leonardtown, MD 20650
Lot 144 - 23635 Dragonfly Ln, Leonardtown, MD 20650Laura Lee Hefley RE/MAX One
-
$1,250 Per Month
- 1 Bed
- 1 Bath
- 800 Sq Ft
- House for Rent
23220 Spalding Ln, Leonardtown, MD 20650
23220 Spalding Ln, Leonardtown, MD 20650Basement apartment with one bedrooms, and a den/study, kitchen, dining and living room combo. One full bath, washer/dryer provided. House above is occupied. Max of two tenants with good credit. Yard available for enjoyment. No pets!!! Water.sewer and trash taken care of by owner. Just pay your electric and cable/wifi. $1250 for one person, $1300 for two occupants monthly rent
Jan Barnes CENTURY 21 New Millennium
-
$518,500
Sold Dec 05, 202522539 Landing Way, Leonardtown, MD 20650
- 3 Beds
- 3.5 Baths
- 2,764 Sq Ft
- Built 2005
Last Sold Summary
- $188/SF
- 12 Days On Market
Current Estimated Value $517,622
Last Listing Agent Trish Brow O'Brien Realty ERA Powered
22539 Landing Way, Leonardtown, MD 20650 -
Est $650,952
Not Listed For Sale22272 Orchard Ct, Leonardtown, MD 20650
- 4 Beds
- 3.5 Baths
- 3,745 Sq Ft
- Built 2004
Last Sold Summary
- 1 Day On Market
Last Listing Agent Christina Reed RE/MAX One
-
$435,000
Pending- 4 Beds
- 2.5 Baths
- 2,624 Sq Ft
40717 Lake and Breton View Dr, Leonardtown, MD 20650
40717 Lake and Breton View Dr, Leonardtown, MD 20650Farrah Fuchs Redfin Corp
-
$2,100 Per Month
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
- House for Rent
22805 Duke St, Leonardtown, MD 20650
22805 Duke St, Leonardtown, MD 20650Enjoy all that Downtown Leonardtown offers through out the year. Comfortable remodeled 3 BR, 1 BA home has hardwood floors, washer/dryer, stainless steel appliances, central a/c and oil heat. Home has a covered side porch, off street parking, and yard maintenance is included in rent. Other details: no pets, 700 credit score, 2 car maximum, no smoking on premises. Home will be available Nov. 7.
Juliet Brown Residential Plus Real Estate Services
-
$639,000
Sold Oct 30, 202541474 Charismatic Way, Leonardtown, MD 20650
- 5 Beds
- 3.5 Baths
- 3,647 Sq Ft
- Built 2015
Last Sold Summary
- $175/SF
- 57 Days On Market
Current Estimated Value $650,300
Last Listing Agent Laura Lee Hefley RE/MAX One
41474 Charismatic Way, Leonardtown, MD 20650 -
Est $769,004
Not Listed For Sale40801 Kiskadee Ln, Leonardtown, MD 20650
- 5 Beds
- 3 Baths
- 6,064 Sq Ft
- Built 2002
Last Sold Summary
- 8 Days On Market
Last Listing Agent Pattee McInerney Scott McInerney RE/MAX One
-
$449,900
New Construction Pending- 4 Beds
- 3.5 Baths
- 2,554 Sq Ft
Lot 158 - 23646 Dragonfly Ln, Leonardtown, MD 20650
Lot 158 - 23646 Dragonfly Ln, Leonardtown, MD 20650Laura Lee Hefley RE/MAX One
-
$2,500 Per Month
- 2 Beds
- 1.5 Baths
- 1,024 Sq Ft
- House for Rent
41603 Church St, Leonardtown, MD 20650
41603 Church St, Leonardtown, MD 20650Less house. More Leonardtown. Be the first to call this brand-new Leonardtown cottage home. Built by the same builder as 41577 Church Street and finished in the same fresh, modern style, 41603 Church Street offers two bedrooms, 1.5 baths and an easy, thoughtfully designed floor plan right in town. The main level includes comfortable living and dining spaces, a well-planned kitchen and a
Michelle Camaioni RE/MAX One
-
$720,000
Sold Jun 26, 202641395 Omaha Ct, Leonardtown, MD 20650
- 5 Beds
- 3.5 Baths
- 4,367 Sq Ft
- Built 2012
Last Sold Summary
- 1% Above List Price
- $165/SF
- 1 Day On Market
Current Estimated Value $711,947
Last Listing Agent Andrew Shemeta CENTURY 21 New Millennium
41395 Omaha Ct, Leonardtown, MD 20650 -
Est $537,667
Not Listed For Sale22186 Monterey Place, Leonardtown, MD 20650
- 4 Beds
- 2 Baths
- 2,935 Sq Ft
- Built 1975
Last Sold Summary
- 54 Days On Market
Last Listing Agent Barbara Stellway KW Metro Center
-
$609,900
New Construction- 4 Beds
- 2.5 Baths
- 2,701 Sq Ft
The Mattingly Plan at Meadows at Town Run - Single Family Homes, Leonardtown, MD 20650
23731 Dragonfly Ln Unit 41509706, Leonardtown, MD 20650Quality Built Homes Builder -
$2,200 Per Month
- 3 Beds
- 2.5 Baths
- 1,384 Sq Ft
- Townhouse for Rent
22758 Lawrence Ave, Leonardtown, MD 20650
22758 Lawrence Ave, Leonardtown, MD 20650Adorable duplex in the heart of downtown Leonardtown. This home has 3 bedrooms and 2 1/2 bathrooms. LVP in main living area and new flooring in kitchen. Kitchen is spacious with eat in area and laundry room. Easy walk to town square and access to shops, restaurants and area amenities. Rent includes water, sewer and trash.
Kelly Padgett Century 21 Redwood Realty
-
$575,000
Sold Mar 05, 202621060 Woodmere Dr, Leonardtown, MD 20650
- 5 Beds
- 3.5 Baths
- 3,075 Sq Ft
- Built 2001
Last Sold Summary
- 2% Above List Price
- $187/SF
- 18 Days On Market
Current Estimated Value $574,309
Last Listing Agent Sharon Cox Century 21 Redwood Realty
21060 Woodmere Dr, Leonardtown, MD 20650 -
Est $338,477
Not Listed For Sale23280 Hollywood Rd, Leonardtown, MD 20650
- 3 Beds
- 1 Bath
- 1,402 Sq Ft
- Built 1956
Last Sold Summary
- 7 Days On Market
Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty
-
$489,900
New Construction Pending- 4 Beds
- 3.5 Baths
- 3,095 Sq Ft
Lot 151 - 23790 Wisteria Ln, Leonardtown, MD 20650
Lot 151 - 23790 Wisteria Ln, Leonardtown, MD 20650Laura Lee Hefley RE/MAX One
-
$1,550 Per Month
- 1 Bed
- 1 Bath
- 900 Sq Ft
- House for Rent
39725 Lady Baltimore Ave Unit 2, Leonardtown, MD 20650
39725 Lady Baltimore Ave Unit 2, Leonardtown, MD 20650Fully Renovated 1-Bedroom Rental Available Now – Leonardtown, MD. $1550 monthly.Beautifully renovated 1-bedroom, 1-bathroom rental featuring convenient, single-level living. This unit is completely separate from the other rental unit and has its own private entrance.Property features:• One bedroom and one bathroom• Fully renovated throughout• All rooms located on one
Thomas Pilkerton Real Broker, LLC
-
$459,900
Sold Jun 17, 202640810 Meadow Dr, Leonardtown, MD 20650
- 3 Beds
- 2 Baths
- 1,368 Sq Ft
- Built 1963
Last Sold Summary
- $336/SF
- 14 Days On Market
Current Estimated Value $448,861
Last Listing Agent Cheryl Bare CENTURY 21 New Millennium
40810 Meadow Dr, Leonardtown, MD 20650 -
Est $343,874
Not Listed For Sale22798 Lawrence Ave, Leonardtown, MD 20650
- 3 Beds
- 1.5 Baths
- 1,160 Sq Ft
- Built 1978
Last Sold Summary
- 28 Days On Market
Last Listing Agent Barbara Click O'Brien Realty ERA Powered
-
$175,000
- Land
- 6.24 Acres
- $28,045 per Acre
0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650 -
$3,195 Per Month
- 4 Beds
- 2.5 Baths
- 2,262 Sq Ft
- House for Rent
41555 Singletree Dr, Leonardtown, MD 20650
41555 Singletree Dr, Leonardtown, MD 20650Luxurious 4BR 2.5FB Colonial style home on an unfinished walk-up basement with a 2 car garage in the Singletree community. You are welcomed home by the 2 story main entry foyer with the living room, family room, kitchen with table space and center island and separate dining room which all share an open floor plan. On the upper level are 3 bedrooms, hall full bath, laundry and a massive vaulted
Joycelyn Clark-Young CENTURY 21 New Millennium
-
$600,000
Sold Oct 01, 202543571 Bayberry Ct, Leonardtown, MD 20650
- 4 Beds
- 2.5 Baths
- 2,946 Sq Ft
- Built 1993
Last Sold Summary
- $204/SF
- 22 Days On Market
Current Estimated Value $614,828
Last Listing Agent Jenny Norris EXP Realty, LLC
43571 Bayberry Ct, Leonardtown, MD 20650 -
Est $542,698
Not Listed For Sale41412 Doctors Crossing Rd, Leonardtown, MD 20650
- 4 Beds
- 3.5 Baths
- 2,686 Sq Ft
- Built 2019
Last Sold Summary
- 67 Days On Market
Last Listing Agent Delaney Clarke RE/MAX United Real Estate
Showing Results 1 - 40, Page 1 of 18
Home Prices in Leonardtown, MD
The median home sale price in Leonardtown, MD is $529,900, down 3% year-over-year. Homes in Leonardtown sell in 38 days on average, compared to the national average of 55 days.
Home Price Trends
|
Median Sale Price
$529,900
|
Median Single Family Sale Price
$595,000
|
|
Median Townhouse Sale Price
$454,900
|
Median 2 Bedroom Sale Price
$315,000
|
|
Average Price Per Sq Ft
$189
|
Number of Homes for Sale
6,720
|
|
Last 12 months Home Sales
187
|
Months of Supply
3.00
|
|
Median List Price
$538,750
|
Median Change From 1st List Price
0%
|
|
Median Home Sale Price YoY Change
-3%
|
|
Copyright © 2026 CoStar Group
