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$929,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,248 Sq. Ft.
  • 2 Car Garage
  • Updated 1 hour ago
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Rare opportunity in Leonardtown! Very private farmstead property with 18.03 acres and a horse barn. The owners have tastefully planted several fruit trees, installed soaker-hose irrigation throughout the orchard, and protected them with fencing so they can mature. The grounds are beautiful and level, with a raised garden with soaker-hose irrigation, also protected by fencing. A composting area is already established on the grounds. The well-built barn has room for 1 horse, a tack room, and 2 storage areas on the main level. The upper level could be used for hay or storage. The property has some fencing, but the new owner would need to complete it if they want to keep a horse. Also included is a storage shed, great for garden tools. This lovely brick-and-vinyl Colonial offers 2,959 sq. ft. of above-grade living space, including 9 ft. ceilings on the main level, 2 story foyer, hardwood on the main level, an upgraded kitchen with a 6-burner propane cooktop, double ovens (one is a convection oven), backsplash, quartz countertops, a center butcher-block island, a breakfast island, and a pantry. Side entry to a mud room in between the oversized 2-car garage. A spacious breakfast area off the kitchen has a French door leading to the massive screened-in porch. The family room is open to the kitchen and has built-in bookcases on each side of the gas fireplace. There's a formal dining room with decorative trim, a tray ceiling, and built-in display corner shelving. Also on the main level is a room that could be used as a library, office, music room, or sitting room. All the rooms have lots of windows that let in natural light. The upper level bedrooms are all spacious with either a walk in closet or double closets. Primary bedroom is massive in size with a cathedral ceiling, 3 walk in closets, large sitting area, primary bathroom with tile, soaking tub, shower, dual sinks, and water closet with a window. The walk-out lower level offers a full bathroom, a partially finished recreation room (exposed but painted ceilings), and a wonderful workshop with benches and a ventilation system. HVAC with propane heat backup on the main level, and a propane water heater. The property really is a hidden gem.

Full Property Details for 20945 Greenwell Way

General

  • Price: $929,900
  • Taxes: $6,100 (2026)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDSM2033970
  • Updated: 10/5/2026
  • Added to Site: 4 day(s) ago

Interior

  • Number of Rooms: 10
  • Rooms/Areas: Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Library, Laundry, Mud Room, Recreation Room, Workshop, Bathroom 2, Bathroom 3, Primary Bathroom
  • Interior Features: Bathroom - Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Breakfast Area, Built-Ins, Carpet, Ceiling Fan(s), Central Vacuum, Chair Railings, Crown Moldings, Family Room Off Kitchen, Floor Plan - Open, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Island, Kitchen - Table Space, Pantry, Primary Bath(s), Recessed Lighting, Wainscotting, Walk-in Closet(s), Upgraded Countertops, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Gas/Propane
  • Appliances: Cooktop - Down Draft, Dishwasher, Dryer - Front Loading, Exhaust Fan, Icemaker, Oven - Double, Oven - Wall, Refrigerator, Stainless Steel Appliances, Washer - Front Loading, Water Heater, Six Burner Stove
  • Flooring: Hardwood, Partially Carpeted, Concrete, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - 1/2 Baths: 1
  • Lower Floor Baths: 1
  • Lower - Full Baths: 1

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 4

Other Rooms

  • Laundry: Upper Floor

Exterior

  • Exterior Features: Outbuilding(s), Sidewalks
  • Porch/Patio/Deck: Deck(s), Enclosed, Porch(es), Screened

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 12
  • Parking Features: Gravel Driveway, Private
  • Parking Type: Attached Garage, Driveway
  • Garage Description: Garage - Side Entry, Garage Door Opener

Location

  • County: SAINT MARYS
  • Driving Directions: GPS
  • Direction Faces: North

School Information

  • School District: St. Mary's County Public Schools
  • Elementary School: Piney Point
  • Middle School: Leonardtown
  • High School: Leonardtown

Community

  • Pets Allowed: Yes
  • Pets: No Pet Restrictions

Heating & Cooling

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

Utilities

  • Sewer: On Site Septic
  • Water: Private, Well
  • Utility Description: Propane, Under Ground

Structural Information

  • Architectural Style: Colonial
  • Structure Type: Detached
  • Construction: Brick, Vinyl Siding
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Daylight, Partial, Interior Access, Outside Entrance, Sump Pump, Walkout Level, Workshop
  • Foundation: Block, Slab
  • Roof: Architectural Shingle
  • Walls/Ceilings: 2 Story Ceilings, 9'+ Ceilings, Cathedral Ceilings, T
  • Windows: Double Hung
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 4,248
  • Sq. Ft. Source: Estimated
  • Living Area: 4,248 Sq. Ft.
  • Finished Above Grnd: 2,959 Sq. Ft.
  • Finished Below Grnd: 1,289 Sq. Ft.
  • Year Built: 2008
  • Year Built Source: Estimated
  • Property Condition: Good

Unit Information

Unit 1

  • Bathrooms-Lower: 1

Additional Structures

  • Other Structures: Barn/Stable, Shed

Lot Features

  • Property View: Panoramic, Trees/Woods
  • Lot Size (Acres): 18.03
  • Lot Size (Sq. Ft.): 785,386
  • Lot Size Source: Estimated
  • Street/Road Desc.: Gravel
  • Zoning: RPD
  • Lot Description: Backs to Trees, Irregular, Private, Rear Yard, Rural, Secluded
  • Fencing (Description): Partially

Horse Property

  • Horse Property: Yes
  • Horse Facility Desc.: Stable(s)

Financial Considerations

  • Price Per Sq. Ft.: $314.26
  • Assessment Year: 2026
  • Tax w/Assessment: $635,600
  • Tax Amount: $6,100
  • Tax Year: 2026

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 3

Listed by O'Brien Realty ERA Powered, Dawn Dawn Wood

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Listing agent

— 20945 Greenwell Way —

  • Dawn Dawn Wood

    O'Brien Realty ERA Powered

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 20945 Greenwell Way

School District:St. Marys County Public Schools
NameGradesDistance
Piney Point Elementary School
44550 Tall Timbers Road, Tall Timbers, MD 20690
PK-56.2 mi
Leonardtown Middle School
24015 Point Lookout Road, Leonardtown, MD 20650
6-82.3 mi
Leonardtown High School
23995 Point Lookout Road, Leonardtown, MD 20650
9-121.9 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 20945 Greenwell Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/01/2026
Listed
$929,900
66.08%
MLS
7/25/2013
Sold
$559,900
—
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 20945 Greenwell Way

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,083
12%
$635,600
4%
2023
$5,421
—
$613,700
7%
2023
$5,421
—
$575,733
7%
2023
$5,421
13%
$537,767
8%
2022
$4,797
3%
$499,800
2%
2019
$4,637
-8%
$490,300
2%
2021
$5,043
2%
$480,800
2%
2020
$4,945
1%
$471,300
1%
2019
$4,909
1%
$467,900
1%
2018
$4,855
—
$464,500
1%
2017
$4,841
2%
$461,100
1%
2016
$4,752
3%
$457,100
1%
2015
$4,613
97%
$453,100
1%
2014
$2,345
—
$449,100
—
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.

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Listed by O'Brien Realty ERA Powered, Dawn Dawn Wood

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20945 Greenwell Way, Leonardtown, MD 20650 (MLS# MDSM2033970) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 20945 Greenwell Way is currently listed for $929,900 and was received on October 01, 2026. Want to learn more about 20945 Greenwell Way? 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.

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