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$560,000
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Property Description
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
Full Property Details for 23299 Jenifer Ct
General
- Sold For: $560,000
- HOA FEE: $21/month
- HOA FEE FREQ.: Annually
- Taxes: $5,420 (2026)
- Status: Closed
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDSM2029912
- Added to Site: 69 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
- Terms: Standard Sale
- Tax Total Finished Sq. Ft.: 3482
Disclosures and Reports
- Ownership: Fee Simple
- Lot Number: 20
Listed by CENTURY 21 New Millennium, Conor M Loughran
Sold by RE/MAX One, Christie Burnett
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Schools
Schools serving 23299 Jenifer Ct
School District:St. Marys County Public Schools
| Name | Grades | Distance |
|---|---|---|
Leonardtown Elementary School 22885 Duke Street, Leonardtown, MD 20650 | PK-5 | 0.8 mi |
Leonardtown Middle School 24015 Point Lookout Road, Leonardtown, MD 20650 | 6-8 | 2.7 mi |
Leonardtown High School 23995 Point Lookout Road, Leonardtown, MD 20650 | 9-12 | 3.1 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
Date
Details
Price
Change
Source
4/24/2026
Sold
$560,000
1.82%
MLS
3/15/2026
Listed
$550,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
23299 Jenifer Court, Leonardtown, MD 20650 (MLS# MDSM2029912) is a Single Family property that was sold at $560,000 on April 24, 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.

