Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$550,000

  • For Sale
  • Under Contract
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 6,964 Sq. Ft.
  • 2 Car Garage
  • Updated 8 days ago
See This Home
Save This Home
See This Home
Save This Home
Beautiful 5BR, 3BA home with over 3,100 sq ft above grade tucked away on a peaceful ½-acre flag lot backing to trees in the heart of Leonardtown. Inside you'll find hardwood flooring, spacious living areas, and a warm, inviting family room perfect for everyday living or entertaining. The kitchen features granite countertops, stainless steel appliances, and plenty of workspace. The main level includes a private guest suite with full bath and second laundry, ideal for visitors, multigenerational living, or a home office. Upstairs offers a large primary suite with its own fireplace, generously sized bedrooms with large closets, and a 15x11 bonus room perfect for a playroom, rec room, or second family space. Enjoy the outdoors with a 10x10 screened porch, two patios, fenced garden/play area, and shaded backyard. Walk to Leonardtown Square, hospital, shopping, and restaurants. Short commute to NAS Pax River. Located in the highly sought-after Leonardtown school district.

Full Property Details for 23299 Jenifer Ct

General

  • Price: $550,000
  • HOA FEE: $21/month
  • HOA FEE FREQ.: Annually
  • Taxes: $5,420 (2026)
  • Status: Under Contract
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDSM2029912
  • Updated: 3/27/2026
  • Added to Site: 20 day(s) ago

Interior

  • Number of Rooms: 12
  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Foyer, 2nd Stry Fam Rm, In-Law/auPair/Suite, Laundry, Bathroom 1, Bathroom 3, Primary Bathroom
  • Interior Features: Breakfast Area, Bar, Built-Ins, Carpet, Ceiling Fan(s), Chair Railings, Crown Moldings, Curved Staircase, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Formal/Separate Dining Room, Kitchen - Gourmet, Kitchen - Table Space, Pantry, Recessed Lighting, Bathroom - Stall Shower, Store/Office, Upgraded Countertops, Walk-in Closet(s), Wood Floors, Other
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Fireplace - Glass Doors, Gas/Propane, Mantel(s)
  • Appliances: Built-In Microwave, Built-In Range, Dishwasher, Disposal, Dryer, Dryer - Electric, Icemaker, Microwave, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances, Washer, Washer/Dryer Stacked, Water Heater

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - Full Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 4
  • Bedrooms Main & Up: 1

Other Rooms

  • Laundry: Upper Floor, Main Floor

Additional Information

  • Security/Safety: Carbon Monoxide Detector(s), Security System

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Type: Attached Garage, Driveway, Off Street
  • Garage Description: Garage - Front Entry, Garage Door Opener

Location

  • Municipality: Leonardtown
  • County: SAINT MARYS
  • Subdivision: ESTATES AT SINGLETREE
  • Driving Directions: Miss Bessie to Jenifer. Driveway at the end of the Cul-de-sac
  • City Limits: Yes

School Information

  • School District: St. Mary's County Public Schools
  • High School: Leonardtown

Community

  • Association: Yes
  • Assoc. Name: ESTATES AT SINGLETREE HOME OWNERS ASSOCIATION

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Heat Pump(s), Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Propane - Owned
  • Water Heater: Bottled Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Colonial
  • Structure Type: Detached
  • Construction: Brick, Combination, Vinyl Siding, Other
  • Foundation: Crawl Space
  • Stories Description: Main, Upper 1
  • Square Feet: 6,964
  • Sq. Ft. Source: Estimated
  • Living Area: 3,482 Sq. Ft.
  • Finished Above Grnd: 3,482 Sq. Ft.
  • Unfin. Above Grnd: 3,482 Sq. Ft.
  • Year Built: 2005
  • Year Built Source: Assessor

Lot Features

  • Property View: Garden/Lawn, Street, Trees/Woods
  • Lot Size (Acres): 0.45
  • Lot Size (Sq. Ft.): 19,814
  • Lot Size Source: Assessor
  • Street/Road Desc.: Paved, Black Top
  • Zoning: R-MF
  • Lot Description: Backs to Trees, Cul-de-sac, Landscaping, Level, No Thru Street, Partly Wooded, Pipe Stem, Rear Yard, SideYard(s), Trees/Wooded

Financial Considerations

  • Price Per Sq. Ft.: $157.96
  • Association Fee: $250
  • Assoc Fee Freq.: Annually
  • City/TownTax: $603
  • City/TownTax Freq: Annually
  • Tax w/Assessment: $523,533
  • Tax Amount: $5,420
  • Tax Year: 2026
  • Tax Total Finished Sq. Ft.: 3482

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 20

Listed by CENTURY 21 New Millennium, Conor M Loughran

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 23299 Jenifer Ct —

  • Conor M Loughran

    CENTURY 21 New Millennium

Listing Office Email: tommy.higgins@c21nm.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 23299 Jenifer Ct

School District:St. Marys County Public Schools
NameGradesDistance
Leonardtown Elementary School
22885 Duke Street, Leonardtown, MD 20650
PK-50.8 mi
Leonardtown Middle School
24015 Point Lookout Road, Leonardtown, MD 20650
6-82.7 mi
Leonardtown High School
23995 Point Lookout Road, Leonardtown, MD 20650
9-123.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 23299 Jenifer Ct Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/15/2026
Listed
$550,000
30.95%
MLS
5/17/2019
Sold
$420,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 23299 Jenifer Ct

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,076
21%
$501,800
7%
2023
$5,019
—
$467,167
8%
2023
$5,019
16%
$432,533
9%
2022
$4,323
25%
$397,900
4%
2019
$3,446
-10%
$382,033
4%
2021
$3,818
4%
$366,167
5%
2020
$3,655
1%
$350,300
1%
2019
$3,611
2%
$346,200
1%
2018
$3,550
1%
$342,100
1%
2017
$3,524
1%
$338,000
—
2016
$3,485
1%
$338,000
—
2015
$3,441
-4%
$338,000
-3%
2014
$3,594
—
$347,200
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 23299 Jenifer Ct

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by CENTURY 21 New Millennium, Conor M Loughran

Similar Properties near 23299 Jenifer Ct

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

21767 Potomac View Dr, Leonardtown, MD 20650 - Photo 1
$555,000

21767 Potomac View Dr  Leonardtown, MD 20650

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 4,384
    Sq. Ft.
Listed by CENTURY 21 New Millennium, Jessica D Raley
23570 Myrtle Point Rd, California, MD 20619 - Photo 1
$569,900

23570 Myrtle Point Rd  California, MD 20619

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 1,860
    Sq. Ft.
Listed by Topside Realty, David C Norris Jr.

Just Listed near 23299 Jenifer Ct

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

43275 Waverly Ct, Hollywood, MD 20636 - Photo 1 Just Listed
$719,900

43275 Waverly Ct  Hollywood, MD 20636

  • Single Family
  • Active
  • Updated 5 hours ago
  • 5
    Beds
  • 3
    Total Baths
  • 6,382
    Sq. Ft.
Listed by CENTURY 21 New Millennium, Tammy Travers
45031 Irvin St, Hollywood, MD 20636 - Photo 1 Just Listed
$370,000

45031 Irvin St  Hollywood, MD 20636

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,508
    Sq. Ft.
Listed by Coldwell Banker Premier, Paul J Fenton and Coldwell Banker Premier, William A Harris
23256 Oak Crest Ln, California, MD 20619 - Photo 1 Just Listed
$450,000

23256 Oak Crest Ln  California, MD 20619

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,313
    Sq. Ft.
Listed by CENTURY 21 New Millennium, Andrew Shemeta
23232 Bent Tree Ln, California, MD 20619 - Photo 1 Just Listed
$349,000
Open House

23232 Bent Tree Ln  California, MD 20619

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,298
    Sq. Ft.
Listed by Goldmine Realty, Teila C. Thorne and Goldmine Realty, Tyra Freeman

Price Reduced near 23299 Jenifer Ct

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

23680 Three Notch Rd, Hollywood, MD 20636 - Photo 1 Price Reduced
-$1 (-6.25%)
$15

23680 Three Notch Rd  #103 & 104  Hollywood, MD 20636

  • Commercial Lease
  • Active
Listed by CENTURY 21 Commercial New Millennium, Mark A Frisco Jr.
23680 Three Notch Rd, Hollywood, MD 20636 - Photo 1 Price Reduced
-$1 (-6.25%)
$15

23680 Three Notch Rd  #201  Hollywood, MD 20636

  • Commercial Lease
  • Active
Listed by CENTURY 21 Commercial New Millennium, Mark A Frisco Jr. and CENTURY 21 New Millennium, Robby Kidwell II
25890 Whiskey Creek Rd, Hollywood, MD 20636 - Photo 1 Price Reduced
-$100,000 (-8.33%)
$1,100,000

25890 Whiskey Creek Rd  Hollywood, MD 20636

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,671
    Sq. Ft.
Listed by CENTURY 21 New Millennium, Edna R Wentworth and CENTURY 21 New Millennium, Kelly D Padgett
43907 Monterey St, California, MD 20619 - Photo 1 Price Reduced
-$10,000 (-1.6%)
$615,000

43907 Monterey St  California, MD 20619

  • Single Family
  • Active
  • Updated 4 days ago
  • 5
    Beds
  • 5
    Total Baths
  • 4,520
    Sq. Ft.
Listed by CENTURY 21 New Millennium, Jennifer L Mullennix

Recent Sales near 23299 Jenifer Ct

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

23261 Jenifer Ct, Leonardtown, MD 20650 - Photo 1 Sold
$565,000

23261 Jenifer Ct  Leonardtown, MD 20650

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 4,360
    Sq. Ft.
Listed by RE/MAX Realty Group, Gabriela Montgomery
Sold by RE/MAX United Real Estate, Delaney I Burgess
41635 Ferber Ct, Leonardtown, MD 20650 - Photo 1 Sold
$535,000

41635 Ferber Ct  Leonardtown, MD 20650

  • Single Family
  • Closed
  • Updated 12 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,170
    Sq. Ft.
Listed by Home Towne Real Estate, Alvin R Frazier
Sold by Berkshire Hathaway HomeServices PenFed Realty, Debbie Friedrich
41535 Singletree Dr, Leonardtown, MD 20650 - Photo 1 Sold
$510,000

41535 Singletree Dr  Leonardtown, MD 20650

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,262
    Sq. Ft.
Listed by JPAR Real Estate Professionals, Karen E Taylor and JPAR Real Estate Professionals, Melanie A Humphrey
Sold by Real Broker, LLC, Alice M Flerlage
41650 Matthew Ct, Leonardtown, MD 20650 - Photo 1 Sold
$475,000

41650 Matthew Ct  Leonardtown, MD 20650

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 3,126
    Sq. Ft.
Listed by Pax River Realty LLC, Paula A Turner
Sold by EXP Realty, LLC, Sarah M. Mulford-Martin

23299 Jenifer Court, Leonardtown, MD 20650 (MLS# MDSM2029912) is a Single Family property with 5 bedrooms and 3 full bathrooms. 23299 Jenifer Court is currently listed for $550,000 and was received on March 15, 2026. Want to learn more about 23299 Jenifer Court? Do you have questions about finding other Single Family real estate for sale in Leonardtown? You can browse all Leonardtown real estate or contact a Coldwell Banker agent to request more information.

Tour this property