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.
Sold for $560,000
$560,000
23299 Jenifer Ct, Leonardtown, MD 20650
5beds
3,482sqft
Single Family Residence
Built in 2005
0.45 Acres Lot
$563,700 Zestimate®
$161/sqft
$3,238 Estimated rent
Home value
$563,700
$507,000 - $626,000
$3,238/mo
Zestimate® history
Owner options
List your home for rent
$3,238/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$3,238/mo
Rent Zestimate®
Refinance and save
$3,622/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$3,622/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Zillow last checked:
Listing updated:
Listed by:
Conor Loughran 301-904-1760,
CENTURY 21 New Millennium
Bought with:
Christie Burnett, 667746
RE/MAX One
Source: Bright MLS,MLS#: MDSM2029912
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 3
- Main level bathrooms: 1
- Main level bedrooms: 1
Rooms
- Room types: 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
Primary bedroom
- Features: Fireplace - Gas, Walk-In Closet(s)
- Level: Upper
Bedroom 2
- Features: Walk-In Closet(s)
- Level: Upper
Bedroom 3
- Features: Walk-In Closet(s)
- Level: Upper
Bedroom 4
- Features: Walk-In Closet(s)
- Level: Upper
Primary bathroom
- Level: Upper
Bathroom 1
- Level: Main
Bathroom 3
- Level: Upper
Other
- Features: Built-in Features, Flooring - Carpet
- Level: Upper
- Area: 165 Square Feet
- Dimensions: 11 X 15
Dining room
- Features: Chair Rail, Crown Molding, Flooring - HardWood
- Level: Main
Family room
- Features: Fireplace - Gas, Flooring - HardWood
- Level: Main
Foyer
- Level: Main
Other
- Features: Walk-In Closet(s)
- Level: Main
Kitchen
- Features: Granite Counters, Dining Area, Flooring - Tile/Brick, Kitchen - Gas Cooking, Pantry
- Level: Main
Laundry
- Level: Upper
Laundry
- Level: Main
Living room
- Features: Flooring - HardWood
- Level: Main
Heating
- Heat Pump, Propane
Cooling
- Heat Pump, Central Air, Electric
Appliances
- Included: Microwave, Built-In Range, Dishwasher, Disposal, Dryer, Ice Maker, Oven/Range - Gas, Refrigerator, Stainless Steel Appliance(s), Washer, Washer/Dryer Stacked, Water Heater, Gas Water Heater
- Laundry: Upper Level, Main Level, Laundry Room
Features
- Breakfast Area, Bar, Built-in Features, Ceiling Fan(s), Chair Railings, Crown Molding, Curved Staircase, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Open Floorplan, Formal/Separate Dining Room, Kitchen - Gourmet, Kitchen - Table Space, Pantry, Recessed Lighting, Bathroom - Stall Shower, Store/Office, Upgraded Countertops, Walk-In Closet(s), Other
- Flooring: Carpet, Wood
- Has basement: No
- Number of fireplaces: 2
- Fireplace features: Glass Doors, Gas/Propane, Mantel(s)
Interior area
- Total structure area: 6,964
- Total interior livable area: 3,482 sqft
- Finished area above ground: 3,482
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Front, Garage Door Opener, Attached, Driveway, Off Street
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Pool features: None
- Has view: Yes
- View description: Garden, Street, Trees/Woods
Lot
- Size: 0.45 Acres
- Features: Backs to Trees, Cul-De-Sac, Landscaped, Level, No Thru Street, Wooded, Pipe Stem, Rear Yard, SideYard(s)
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1903071677
- Zoning: R-MF
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Brick, Combination, Vinyl Siding, Other
- Foundation: Crawl Space
Condition
- New construction: No
- Year built: 2005
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Security: Carbon Monoxide Detector(s), Security System
- Subdivision: Estates At Singletree
HOA
- Has HOA: Yes
- HOA fee: $250 annually
- HOA name: ESTATES AT SINGLETREE HOME OWNERS ASSOCIATION
Location
- Region: Leonardtown
- Municipality: Leonardtown
Financial & listing details
- Price per square foot: $161/sqft
- Tax assessed value: $523,533
- Annual tax amount: $5,420
- Date on market: 3/15/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
- Road surface type: Paved, Black Top
Price history
| Date | Event | Price |
|---|---|---|
| 4/24/2026 | Sold | $560,000+1.8%$161/sqft |
Source:  Bright MLS #MDSM2029912 Report a problem | ||
| 3/27/2026 | Contingent | $550,000$158/sqft |
Source: Bright MLS #MDSM2029912 Report a problem | ||
| 3/23/2026 | Listed for sale | $550,000+31%$158/sqft |
Source: Bright MLS #MDSM2029912 Report a problem | ||
| 5/22/2019 | Sold | $420,000$121/sqft |
Source: Public Record Report a problem | ||
| 3/23/2019 | Pending sale | $420,000$121/sqft |
Source: O Brien Realty #MDSM150618 Report a problem | ||
| 2/8/2019 | Listed for sale | $420,000+5.5%$121/sqft |
Source: O Brien Realty #MDSM150618 Report a problem | ||
| 7/2/2015 | Listing removed | $2,400$1/sqft |
Source: Long & Foster Real Estate, Inc. #SM8630270 Report a problem | ||
| 5/12/2015 | Listed for rent | $2,400$1/sqft |
Source: Long & Foster Real Estate, Inc. #SM8630270 Report a problem | ||
| 10/8/2014 | Listing removed | $398,000$114/sqft |
Source: CENTURY 21 New Millennium #SM8319007 Report a problem | ||
| 8/8/2014 | Price change | $398,000-2.7%$114/sqft |
Source: CENTURY 21 New Millennium #SM8319007 Report a problem | ||
| 7/3/2014 | Price change | $409,000-4.9%$117/sqft |
Source: CENTURY 21 New Millennium #SM8319007 Report a problem | ||
| 4/16/2014 | Listed for sale | $430,000-14%$123/sqft |
Source: CENTURY 21 New Millennium #SM8319007 Report a problem | ||
| 6/13/2009 | Listing removed | $499,900$144/sqft |
Source: Long and Foster Real Estate #SM6997776 Report a problem | ||
| 3/8/2009 | Listed for sale | $499,900+376.1%$144/sqft |
Source: Long and Foster Real Estate #SM6997776 Report a problem | ||
| 5/18/2005 | Sold | $105,000+23.5%$30/sqft |
Source: Public Record Report a problem | ||
| 1/14/2005 | Sold | $85,000$24/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $6,119 +21.3% | $501,800 +7.4% |
| 2024 | $5,046 +8% | $467,167 +8% |
| 2023 | $4,672 +8.1% | $432,533 +8.7% |
| 2022 | $4,323 +4.2% | $397,900 +4.2% |
| 2021 | $4,150 +4.3% | $382,033 +4.3% |
| 2020 | $3,978 +4.5% | $366,167 +4.5% |
| 2019 | $3,806 +1.2% | $350,300 +1.2% |
| 2018 | $3,761 +13.5% | $346,200 +1.2% |
| 2017 | $3,315 -7.8% | $342,100 +1.2% |
| 2016 | $3,594 | $338,000 |
| 2015 | $3,594 | $338,000 |
| 2014 | $3,594 | $338,000 -2.6% |
| 2013 | -- | $347,200 |
| 2012 | -- | $347,200 |
| 2011 | -- | $347,200 -18.2% |
| 2010 | -- | $424,330 +5.9% |
| 2009 | -- | $400,762 +6.2% |
| 2008 | -- | $377,196 +6.7% |
| 2007 | -- | $353,630 +4.5% |
| 2006 | -- | $338,462 +497.9% |
| 2005 | -- | $56,606 +10% |
| 2004 | -- | $51,470 |
Find assessor info on the county website
Neighborhood: 20650
Nearby homes
- $622,800-- bd2 ba3k sqft23295 Jenifer Ct, Leonardtown, MD 20650Off Market
- $669,9005 bd4 ba4.9k sqft23298 Jenifer Ct, Leonardtown, MD 20650Off Market
- $102,800-- bd-- ba-- sqft41584 Susie Ct, Leonardtown, MD 20650Off Market
- $500-- bd-- ba-- sqftCoach Ct, Leonardtown, MD 20650Off Market
- $602,400-- bd2 ba2.6k sqft41584 Susie Ct, Leonardtown, MD 20650Off Market
- $591,0004 bd4 ba4.6k sqft23285 Jenifer Ct, Leonardtown, MD 20650Off Market
- $94,200-- bd-- ba-- sqft23339 Greenbrier Rd, Leonardtown, MD 20650Off Market
- $499,1003 bd2 ba1.8k sqft23335 Greenbrier Rd, Leonardtown, MD 20650Off Market
Nearby schools
GreatSchools rating
- 7/10Leonardtown Elementary SchoolGrades: PK-5Distance: 0.8 mi
- 8/10Leonardtown Middle SchoolGrades: 6-8Distance: 2.7 mi
- 5/10Leonardtown High SchoolGrades: 9-12Distance: 3.1 mi
Schools provided by the listing agent
- High: Leonardtown
- District: St. Mary's County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$563,700
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$563,700
- Maryland
- Saint Marys County
- Leonardtown
- 20650
- 23299 Jenifer Ct
Nearby cities
Nearby zip codes
Other Leonardtown Topics
