NO SHOWINGS UNTILL THE OPEN HOUSE MAY 24, SAT 11-2. Exceptional 5-Bedroom Home on 2 Acres. Welcome to this gorgeous 5-bedroom, 3.5-bath custom home, perfectly situated on a beautifully landscaped 2-acre lot. Impeccably maintained and thoughtfully designed, this property offers an ideal blend of luxury, comfort, and practicality. All five bedrooms are located on the upper level, including a stunning primary suite with a spacious sitting area and elegant French doors. The en-suite bath features a soaking tub, separate shower, and a double-sink, granite-top vanity, complemented by abundant walk-in closet. The upper level also includes a shared hall bath, linen closet, and an open staircase that enhances the airy layout. The main floor features a flexible den/office, formal dining room, charming parlor, and a bright, open-concept kitchen and family room. The kitchen is a cook's delight, equipped with a center island, eat-at counter, wall oven, additional stove/oven combo, beverage cooler, giant walk-in pantry, and sliding doors that open to a spacious deck overlooking the fenced backyard. The finished basement offers even more living space, featuring a large family room, a full bathroom, ample storage near the utilities, and convenient walkout access to the backyard. The exterior features a charming front porch, mature landscaping all around, fully fenced area in the backyard for the doggies and a separately fenced area for gardening. Besides an ample 2-car garage the driveway has parking for up to 6 vehicles. Roof replaced in 2019, HVAC system (2014 or newer), Brand-new hot water tank. Located just 15 minutes from St. Mary's River Park, a 2,000-acre nature reserve featuring a 250-acre fishing lake. Discover the charm and natural beauty of St. Mary's, a community rich in history and outdoor adventure.
Sold for $640,000
$640,000
44114 Woodmont Dr, Leonardtown, MD 20650
5beds
3,635sqft
Single Family Residence
Built in 1999
2 Acres Lot
$663,500 Zestimate®
$176/sqft
$3,481 Estimated rent
Home value
$663,500
$617,000 - $710,000
$3,481/mo
Zestimate® history
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List your homeWhat's special
Charming parlorFinished basementMature landscapingElegant french doorsAbundant walk-in closetSeparate showerSpacious deck
Zillow last checked:
Listing updated:
Listed by:
Lori Jean Buongiovanni 240-441-2934,
RE/MAX Realty Group
Bought with:
Jaymie Lewis, 669009
O'Brien Realty ERA Powered
Source: Bright MLS,MLS#: MDSM2023726
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Rooms
- Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Family Room, Foyer, Study, Laundry, Office
Primary bedroom
- Features: Flooring - Carpet
- Level: Upper
Bedroom 2
- Features: Flooring - Carpet
- Level: Upper
Bedroom 3
- Features: Flooring - Carpet
- Level: Upper
Bedroom 4
- Features: Flooring - Carpet
- Level: Upper
Bedroom 5
- Features: Flooring - Carpet
- Level: Upper
Dining room
- Features: Flooring - HardWood
- Level: Main
Family room
- Features: Flooring - Carpet
- Level: Main
Family room
- Level: Lower
Foyer
- Features: Flooring - HardWood
- Level: Main
Kitchen
- Features: Flooring - HardWood
- Level: Main
Laundry
- Level: Unspecified
Living room
- Features: Flooring - Carpet
- Level: Main
Office
- Level: Main
Study
- Level: Unspecified
Heating
- Heat Pump, Electric
Cooling
- Central Air, Electric
Appliances
- Included: Microwave, Built-In Range, Cooktop, Dishwasher, Disposal, Dryer, Oven, Washer, Water Heater, Electric Water Heater
- Laundry: Laundry Room
Features
- Breakfast Area, Kitchen Island, Dining Area, Primary Bath(s), Floor Plan - Traditional
- Flooring: Wood
- Windows: Screens, Window Treatments
- Basement: Connecting Stairway,Improved
- Number of fireplaces: 1
- Fireplace features: Screen
Interior area
- Total structure area: 3,765
- Total interior livable area: 3,635 sqft
- Finished area above ground: 2,902
- Finished area below ground: 733
Property
Parking
- Total spaces: 2
- Parking features: Garage Door Opener, Attached
- Attached garage spaces: 2
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck, Porch
- Pool features: None
Lot
- Size: 2 Acres
- Features: Backs to Trees, Stream/Creek
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1902037327
- Zoning: RNC
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Architectural Shingle
Condition
- New construction: No
- Year built: 1999
Details
- Builder name: ERRINGTON
Utilities & green energy
- Sewer: Septic Exists
- Water: Well
- Utilities for property: Electricity Available, Propane
Community & HOA
Community
- Subdivision: Chestnut Hills
HOA
- Has HOA: No
Location
- Region: Leonardtown
- Municipality: LEONARDTOWN
Financial & listing details
- Price per square foot: $176/sqft
- Tax assessed value: $469,900
- Annual tax amount: $4,271
- Date on market: 5/18/2025
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional,FHA,VA Loan,USDA Loan
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 6/29/2025 | Sold | $640,000+4.1%$176/sqft |
Source:  Bright MLS #MDSM2023726 Report a problem | ||
| 5/28/2025 | Contingent | $615,000$169/sqft |
Source: Bright MLS #MDSM2023726 Report a problem | ||
| 5/18/2025 | Listed for sale | $615,000+77%$169/sqft |
Source: Bright MLS #MDSM2023726 Report a problem | ||
| 7/3/2003 | Sold | $347,500+35.1%$96/sqft |
Source: Public Record Report a problem | ||
| 10/12/1999 | Sold | $257,300$71/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,803 +12.5% | $469,900 +5.6% |
| 2024 | $4,271 +5.9% | $444,967 +5.9% |
| 2023 | $4,031 +6.3% | $420,033 +6.3% |
| 2022 | $3,792 +0.4% | $395,100 +0.4% |
| 2021 | $3,776 +0.4% | $393,367 +0.4% |
| 2020 | $3,759 +0.4% | $391,633 +0.4% |
| 2019 | $3,742 +0.5% | $389,900 +0.5% |
| 2018 | $3,722 -0.4% | $387,800 +0.5% |
| 2017 | $3,737 -14% | $385,700 +0.5% |
| 2016 | $4,347 | $383,600 |
| 2015 | $4,347 | $383,600 |
| 2014 | $4,347 | $383,600 -7.4% |
| 2013 | -- | $414,400 |
| 2012 | -- | $414,400 |
| 2011 | -- | $414,400 -19.4% |
| 2010 | -- | $513,840 +7% |
| 2009 | -- | $480,396 +7.5% |
| 2008 | -- | $446,953 +8.1% |
| 2007 | -- | $413,510 +10.9% |
| 2006 | -- | $372,810 +12.3% |
| 2005 | -- | $332,110 +14% |
| 2004 | -- | $291,410 +3.2% |
| 2003 | -- | $282,266 +3.3% |
| 2002 | -- | $273,123 +3.5% |
| 2001 | -- | $263,980 |
Find assessor info on the county website
Neighborhood: 20650
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Nearby schools
GreatSchools rating
- 7/10Piney Point Elementary SchoolGrades: PK-5Distance: 4.4 mi
- 9/10Leonardtown Middle SchoolGrades: 6-8Distance: 4.3 mi
- 8/10Leonardtown High SchoolGrades: 9-12Distance: 4 mi
Schools provided by the listing agent
- 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.
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Estimated market value
$663,500
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Estimated market value
$663,500
- Maryland
- Saint Marys County
- Leonardtown
- 20650
- 44114 Woodmont Dr
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