22237 Bayside Rd, Leonardtown, MD 20650
OFF MARKET

22237 Bayside Rd
Leonardtown, MD 20650

  • Studio

$333,400

Trulia Estimate
as of Jul 27, 2026

$333,400

Trulia Estimate
as of Jul 27, 2026
Studio

Local Information

  • Map ViewExplore the area around 22237 Bayside Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home

About this House

This single-family home is located at 22237 Bayside Rd, Leonardtown, MD. 22237 Bayside Rd is in Leonardtown, MD and in ZIP code 20650.
22237 Bayside Rd, Leonardtown, MD 20650 is a studio single-family home. It last sold for $100,000 on Dec 6, 2019 (5,163% above the $1,900 asking price). More recently, it was listed as a rental in January 2025 with an asking price of $2,100 per month. That rental listing was removed on March 10, 2025. It is currently off market. The Trulia Estimate is $333,400, with a rent estimate of $2,168/month.

Home Details for 22237 Bayside Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For Details

Price History for 22237 Bayside Rd

DatePriceEventSource
03/10/2025$2,100ListingRemovedZillow Rentals
01/23/2025$2,100Listed For RentZillow Rentals
12/06/2019$100,000Sold
N/A
04/29/2002$119,000Sold
N/A

Market trends in Leonardtown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$540K
$19.15KMoM
Sale-to-List Price
100.0%
Price per sq ft
$199
$3MoM
Available listings
23
10MoM
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Property Tax and Assessment

Year2025
Tax$2,764
Assessment$248,600
Home facts updated by county records

Comparable Sales for 22237 Bayside Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
22175 Bayside Rd, Leonardtown, MD
0.12
Single-Family Home
$315,000
05/28/26
2
2
1,192
39944 Lady Baltimore Ave, Leonardtown, MD
0.13
Single-Family Home
$400,000
06/15/26
5
2.5
2,169
39885 Lady Baltimore Ave, Leonardtown, MD
0.23
Single-Family Home
$340,000
01/16/26
3
2
1,344
39771 Lady Baltimore Ave, Leonardtown, MD
0.45
Single-Family Home
$475,000
03/09/26
4
3
1,796
Breton St, Leonardtown, MD
0.56
Single-Family Home
$310,000
04/22/26
4
5
3,000
22305 Rocky Point Farm Ln, Leonardtown, MD
0.60
Single-Family Home
$336,000
08/26/25
2
2,300
22381 Cedar St, Leonardtown, MD
0.66
Single-Family Home
$335,000
07/07/26
3
2
1,287
22204 Nomoni St, Leonardtown, MD
0.71
Single-Family Home
$315,000
04/10/26
2
2
1,008
22317 Cedar St, Leonardtown, MD
0.71
Single-Family Home
$340,000
08/19/25
3
1.5
1,296
21920 Newtowne Neck Rd, Leonardtown, MD
0.63
Single-Family Home
$520,000
01/30/26
4
2.5
2,291

Nearby homes

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Assigned Schools

These are the assigned schools for 22237 Bayside Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Leonardtown

At least 38 Trulia users voted on each feature.

  • 91 % Say parking is easy

  • 91 % Say yards are well-kept

  • 86 % Say people would walk alone at night

  • 86 % Say kids play outside

  • 86 % Say car is needed

  • 85 % Say it's dog friendly

  • 75 % Say there's holiday spirit

  • 72 % Say it's quiet

  • 62 % Say there are sidewalks

  • 61 % Say streets are well-lit

  • 61 % Say they plan to stay for at least 5 years

  • 58 % Say there's wildlife

  • 51 % Say neighbors are friendly

  • 43 % Say it's walkable to restaurants

  • 42 % Say there are community events

  • 14 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Carrieibly
    "Don’t have one i’m a biz owner here. Many small businesses in town. Great for boaters and water enthusiasts "
    0
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  • Mybeachjeweler
    "The dogs are very happy and normally quiet when being walked on the sidewalk in Clark’s Rest Community "
    0
    Flag
  • Zddnpc8dsh
    "The downtown is a vibrant place, with piped in music and lots of community activities, like First Friday events every month."
    0
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  • Mybeachjeweler
    "You can walk your dogs on a lease in ease and children love to wave and pet the dogs if the owner allows. This is a great community for dogs as long as they are not barking all the time. "
    0
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  • Vmagostinelli
    "I love first Fridays! I love the town vibe! The wharf is amazing. Most people can’t walk to everything. I feel I’m fortunate!"
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  • Mybeachjeweler
    "Dog owners would like this neighborhood as many neighbors have dogs and walk them on leases daily. Dogs are friendly "
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  • Mybeachjeweler
    "I see people walking their dogs day and night. All dogs are on a lease and are most friendly to chi "
    0
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  • Vmagostinelli
    "It’s an amazing small town with entertainment and great restaurants within walking distance. Located on Breton Bay with great boating and fishing options. "
    0
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  • Keith H.
    "Great neighborhood with sidewalks and many families. Good schools and a library just outside the entrance. "
    0
    Flag
  • Mybeachjeweler
    "I see many walking their dogs on a daily path around the neighborhood everybody has their dog on a leash and we wave"
    0
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  • Keith H.
    "Good consistent drive. Traffic moves on major roads. About 15-20 min delay during morning and evening rush hours. "
    1
    Flag
  • Stillask8in
    "This is a very small town. Most people commute 45 mins to the military base for work. Longest commute of my life. "
    0
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  • Roy M.
    "Great schools in the Leonardtown area and lots of history as well. Many different food choices from Seafood Mexican AMERICAN Chinese and the olde town cafe. "
    0
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  • Roy M.
    "Local town events and close to water access. Great food lots of shopping and small businesses Everyone is polite and friendly Great schools and local parks Volunteer rescue squad and fire departments and local hospital Local beach communities Golfing "
    0
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  • Jennie C.
    "30 minutes from pax naval base, 40 min to Waldorf, 30-45 min from Calvert County. Some local buses available also."
    2
    Flag
  • Unspecified
    "Easy, multiple routes to the Naval Air Station. From Leonardtown it is easy to get to all restaurants, shopping and entertainment."
    0
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  • Unspecified
    "Perfect, close to the base and beautiful downtown Leonardtown. On the golf course with a few hundred yard walk to clubhouse (which has fantastic food and drinks), but most importantly, only a short walk to the Breton Bay Beach and playground which the children (and adults) love!"
    4
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  • Destiny A. M.
    "I have two dogs myself and walk them all the time. I like they have side walks for my dogs to walk on but I don’t like that there isn’t a dog park anywhere around here. I feel they should add dog parks around here to make it better for dogs to get the excerise they need and want. "
    0
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  • Destiny A. M.
    "Love leonardtown and love the area that I’m in. I love that everything is right here in the square and have so many nice people around me. Everyone in this area knows me and says hi even if they don’t know who you are. "
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  • dtscls
    "The townhomes at Breton Bay Landing are all excellently maintained by HOA standards; including the grounds and road maintenance. The community is family friendly and welcoming. The waterfront is beautiful and the nature friendly environment includes eagles, swans, geese and numerous beautiful birds."
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

7 pet-friendly rentals in Leonardtown, MD

Explore by feature - Air Conditioning

8 rentals with air conditioning in Leonardtown, MD

Homes for sale near 22237 Bayside Rd

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Off Market Homes Near 22237 Bayside Rd

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