$1,300,000

23155 Greenstone Dr 3, Leonardtown, MD 20650

Estimated payment $7,917/month

Total Views 26,646
6 Beds
3.5 Baths
5,888 Sq Ft
$221 Price per Sq Ft

Highlights

  • Filtered Pool
  • Gourmet Kitchen
  • Dual Staircase
  • Leonardtown Middle School Rated A-
  • Open Floorplan
  • Colonial Architecture

About This Home

Luxury, Space, and Sophistication – All in One Remarkable Property! Prepare to be impressed by this meticulously maintained almost 7,000 sq ft estate—a rare gem that blends luxury, comfort, and functionality in every detail. If your current home lacks character or space, this extraordinary residence will exceed all your expectations! Interior Highlights: • Gourmet Kitchen with oversized island, walk-in pantry featuring a second island and refrigerator • Wet bar/Coffee station and recessed lighting throughout • Main-level office with custom built-in desk and counters • Spacious dining room and large breakfast area perfect for gatherings • Stainless steel appliances and cozy propane fireplace •Under cabinet lighting • Cat 6 wiring throughout for seamless connectivity and hard wired ethernet cables in every room• Wifi access point on every floor •Laundry rooms on all three levels for ultimate convenience • Two staircases provide easy access to the second floor Owner’s Retreat: • Expansive Owner’s Suite with a massive walk-in closet featuring an island with built-in cabinetry • Spa-like ensuite bath with rain shower head, dual sprayers, and tiled ledge Bedroom Features: • 6 spacious bedrooms, 5 equipped with custom closet organizers Entertainment & Lifestyle: • Sunroom leading to a covered porch—perfect for year-round relaxation • Theatre room with projector, 7.1 surround sound with 150" screen and projector and bar in the basement • 20’ x 40’ chlorinated pool with a 9” deep sundeck, automatic cover, and expansive patio • Blink security system with cameras and spotlights and alarm contacts and glass break sensors • Safe area under front porch • Stunning foyer chandelier that makes a grand first impression Garage & Storage: • Oversized gutters with leaf guards •Attached 3-car side load garage with remote door openers • Detached 42’ x 38’ garage/workshop—ideal for storage, hobbies, or a man cave with 960 sq ft of conditioned space Bonus Features: • Fully insulated floors and interior walls for sound control •Tankless water heater & whole house dehumidifier• Full 18-zone yard irrigation system • Gutters piped underground • Includes an additional 4+ acre lot—a rare opportunity to expand or enjoy added privacy This home truly has everything—and it’s all been immaculately maintained. Private showings available by appointment only with a minimum of one hour notice.

Listing Agent

Jimmy Hayden

RE/MAX Realty Group Listed on: 06/10/2025

RE/MAX Realty Group

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $7,781

Year Built

  • Built in 2020

Lot Details

  • 1.52 Acre Lot
  • Sprinkler System
  • Property is in excellent condition
  • Property is zoned RPD

HOA Fees

  • $75 Monthly HOA Fees

Parking

  • 5 Garage Spaces | 3 Attached and 2 Detached
  • Parking Storage or Cabinetry
  • Side Facing Garage
  • Garage Door Opener
  • Driveway

Home Design

  • Colonial Architecture
  • Vinyl Siding
  • Concrete Perimeter Foundation

Interior Spaces

  • Property has 3 Levels
  • Open Floorplan
  • Wet Bar
  • Dual Staircase
  • Sound System
  • Built-In Features
  • Bar
  • Ceiling Fan
  • Recessed Lighting
  • Gas Fireplace
  • Family Room Off Kitchen
  • Dining Area

Kitchen

  • Gourmet Kitchen
  • Breakfast Area or Nook
  • Butlers Pantry
  • Double Oven
  • Electric Oven or Range
  • Down Draft Cooktop
  • Built-In Microwave
  • Dishwasher
  • Stainless Steel Appliances
  • Kitchen Island
  • Upgraded Countertops
  • Disposal

Flooring

  • Engineered Wood
  • Carpet
  • Ceramic Tile

Bedrooms and Bathrooms

  • En-Suite Bathroom
  • Walk-In Closet
  • Walk-in Shower

Laundry

  • Laundry Room
  • Laundry on main level
  • Electric Dryer
  • Washer

Finished Basement

  • Interior and Exterior Basement Entry
  • Laundry in Basement
  • Basement Windows

Home Security

  • Home Security System
  • Exterior Cameras
  • Motion Detectors

Pool

  • Filtered Pool
  • In Ground Pool

Utilities

  • Zoned Cooling
  • Heat Pump System
  • Well
  • Tankless Water Heater
  • Propane Water Heater
  • Septic Tank

Community Details

  • The Preserve At Big Chestnut HOA
  • Big Chestnut Subdivision

Listing and Financial Details

  • Tax Lot 21
  • Assessor Parcel Number 1903077160

Home Details

Home Type

Single Family

Est. Annual Taxes

$7,781

Year Built

Built in 2020

Lot Details

0

HOA Fees

$75 per month

Parking

5

Listing Details

  • Property Type: Residential
  • Structure Type: Detached
  • Architectural Style: Colonial
  • Ownership: Fee Simple
  • New Construction: No
  • Story List: Lower 1, Main, Upper 1
  • Expected On Market: 6/13/2025 12:00:00 AM
  • Year Built: 2020
  • Remarks Public: Luxury, Space, and Sophistication – All in One Remarkable Property! Prepare to be impressed by this meticulously maintained almost 7,000 sq ft estate—a rare gem that blends luxury, comfort, and functionality in every detail. If your current home lacks character or space, this extraordinary residence will exceed all your expectations! Interior Highlights: • Gourmet Kitchen with oversized island, walk-in pantry featuring a second island and refrigerator • Wet bar/Coffee station and recessed lighting throughout • Main-level office with custom built-in desk and counters • Spacious dining room and large breakfast area perfect for gatherings • Stainless steel appliances and cozy propane fireplace •Under cabinet lighting • Cat 6 wiring throughout for seamless connectivity and hard wired ethernet cables in every room• Wifi access point on every floor •Laundry rooms on all three levels for ultimate convenience • Two staircases provide easy access to the second floor Owner’s Retreat: • Expansive Owner’s Suite with a massive walk-in closet featuring an island with built-in cabinetry • Spa-like ensuite bath with rain shower head, dual sprayers, and tiled ledge Bedroom Features: • 6 spacious bedrooms, 5 equipped with custom closet organizers Entertainment & Lifestyle: • Sunroom leading to a covered porch—perfect for year-round relaxation • Theatre room with projector, 7.1 surround sound with 150" screen and projector and bar in the basement • 20’ x 40’ chlorinated pool with a 9” deep sundeck, automatic cover, and expansive patio • Blink security system with cameras and spotlights and alarm contacts and glass break sensors • Safe area under front porch • Stunning foyer chandelier that makes a grand first impression Garage & Storage: • Oversized gutters with leaf guards •Attached 3-car side load garage with remote door openers • Detached 42’ x 38’ garage/workshop—ideal for storage, hobbies, or a man cave with 960 sq ft of conditioned space Bonus Features: • Fully insulated floors and interior walls for sound control •Tankless water heater & whole house dehumidifier• Full 18-zone yard irrigation system • Gutters piped underground • Includes an additional 4+ acre lot—a rare opportunity to expand or enjoy added privacy This home truly has everything—and it’s all been immaculately maintained. Private showings available by appointment only with a minimum of one hour notice.
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Appliances: Built-In Microwave, Cooktop, Cooktop - Down Draft, Dishwasher, Disposal, Dryer - Electric, Oven - Double, Oven/Range - Electric, Refrigerator, Stainless Steel Appliances, Washer, Water Heater, Water Heater - Tankless
  • Flooring Type: Ceramic Tile, Carpet, Engineered Wood
  • Interior Amenities: Bar, Bathroom - Walk-In Shower, Breakfast Area, Built-Ins, Butlers Pantry, Carpet, Ceiling Fan(s), Dining Area, Double/Dual Staircase, Family Room Off Kitchen, Floor Plan - Open, Kitchen - Gourmet, Kitchen - Island, Pantry, Primary Bath(s), Recessed Lighting, Sound System, Sprinkler System, Upgraded Countertops, Walk-In Closet(s), Wet/Dry Bar
  • Fireplace Features: Gas/Propane
  • Fireplaces Count: 1
  • Fireplace: Yes
  • Foundation Details: Concrete Perimeter
  • Levels Count: 3
  • Room List: Laundry
  • Basement: Yes
  • Basement Type: Daylight, Full, Fully Finished, Improved, Interior Access, Outside Entrance, Windows
  • Laundry Type: Basement, Main Floor, Upper Floor, Dryer In Unit, Washer In Unit
  • Total Sq Ft: 6932
  • Living Area Sq Ft: 5888
  • Price Per Sq Ft: 277.30
  • Above Grade Finished Sq Ft: 4688
  • Below Grade Finished Sq Ft: 1200
  • Below Grade Sq Ft: 1044
  • Total Below Grade Sq Ft: 2244
  • Above Grade Finished Area Units: Square Feet
  • Street Number Modifier: 23155

Beds/Baths

  • Bedrooms: 6
  • All Lower Level Bedrooms: 2
  • Lower Level Bedroom: 2
  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Main Level Bathrooms: 1.00
  • Upper Level Bathrooms: 2
  • Lower Levels Bathrooms: 1
  • Upper Level Bathrooms: 2.00
  • Lower Levels Bathrooms: 1.00
  • Upper Level Full Bathrooms: 2
  • Lower Level Full Bathrooms: 1
  • Lower Level Full Bathrooms: 1
  • Main Level Half Bathrooms: 1

Exterior Features

  • Other Structures: Above Grade, Below Grade
  • Construction Materials: Concrete, Vinyl Siding
  • Pool Features: Filtered, In Ground
  • Water Access: No
  • Waterfront: No
  • Water Oriented: No
  • Pool: Yes - Personal
  • Tidal Water: No
  • Water View: No

Garage/Parking

  • Garage Spaces: 5.00
  • Garage: Yes
  • Garage Features: Additional Storage Area, Garage - Side Entry, Garage Door Opener, Oversized
  • Attached Garage Spaces: 3
  • Number Of Detached Garage Spaces: 2
  • Total Garage And Parking Spaces: 5
  • Type Of Parking: Attached Garage, Detached Garage, Driveway

Utilities

  • Central Air Conditioning: No
  • Cooling Fuel: Electric
  • Cooling Type: Heat Pump(s), Zoned
  • Heating Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating: Yes
  • Hot Water: Propane, Tankless
  • Security: Exterior Cameras, Motion Detectors, Security System
  • Sewer/Septic System: Septic Exists
  • Water Source: Well

Condo/Co-op/Association

  • HOA Fees: 900.00
  • HOA Fee Frequency: Annually
  • Condo Co-Op Association: No
  • HOA Name: THE PRESERVE AT BIG CHESTNUT
  • HOA: Yes
  • Senior Community: No

Schools

  • School District: ST. MARY'S COUNTY PUBLIC SCHOOLS
  • School District Key: 121138839208
  • School District Source: Listing Agent

Lot Info

  • Land Use Code: R
  • Lot Size Acres: 1.52
  • Lot Size Units: Square Feet
  • Lot Sq Ft: 66211.00
  • Property Condition: Excellent
  • Year Assessed: 2025
  • Zoning: RPD
  • In City Limits: No

Rental Info

  • Vacation Rental: No

Tax Info

  • Tax Annual Amount: 7781.00
  • Assessor Parcel Number: 1903077160
  • Tax Lot: 21
  • Tax Total Finished Sq Ft: 5888
  • County Tax Payment Frequency: Annually
  • Tax Year: 2024

MLS Schools

  • School District Name: ST. MARY'S COUNTY PUBLIC SCHOOLS

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2024 $8,665 $810,667 $0 $0
2023 $7,906 $761,733 $0 $0
2022 $7,406 $712,800 $132,600 $580,200
2021 $7,250 $697,600 $0 $0
2020 $7,093 $682,400 $0 $0
2019 $1,094 $107,600 $107,600 $0
2018 $1,077 $105,933 $0 $0
2017 $1,060 $104,267 $0 $0
2016 -- $102,600 $0 $0
2015 $1,146 $102,600 $0 $0
2014 $1,146 $102,600 $0 $0
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
06/10/2025 06/10/25 For Sale $1,300,000 +733.3% $221 / Sq Ft
10/04/2019 10/04/19 Sold $156,000 0.0% --
10/04/2019 10/04/19 Pending -- -- --
10/04/2019 10/04/19 For Sale $156,000 -- --
Source: Bright MLS

Purchase History

Date Type Sale Price Title Company
Deed $156,000 Titlemax Llc
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Closed $0 Credit Line Revolving
Open $510,400 New Conventional
Closed $500,000 Construction
Closed $124,800 Purchase Money Mortgage
Previous Owner $660,000 Stand Alone Refi Refinance Of Original Loan
Source: Public Records

About the Listing Agent

Jimmy Hayden

RE/MAX Realty Group

(240) 387-9601

Section Image

As a St. Mary’s County native, born and raised in the Hollywood / Leonardtown area, and a former self employed business owner that tripled the business sales, I have the drive to excel in helping you with your real estate needs.

I am very involved in my community. I am the past Vice President of the Hollywood Volunteer Fire Department and have held the offices of Treasurer and President. I stay locally involved to keep my home town a town that all want to live in as current Chair of the

Jimmy's Other Listings

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    • 2.5 Baths
    • 2,330 Sq Ft
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    Boast in the benefit of this cul-de-sac home on the outskirts of town that backs to a farm but with the closeness and convenience of being so close to area schools, restaurants, stores, and hospital. This home is ready for you to make it your own. The backyard privacy with deck and patio are great for enjoying the nature sounds. Large shed to keep the tools needed to keep the beautiful lawn

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  • 37420 River Springs Rd, Avenue, MD 20609

    $589,000

    • 2 Beds
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    • 2,112 Sq Ft
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    Unique waterfront property w/ guest house. New dock, w/ marine grade lumber and stainless-steel fasteners was raised to be higher than the avg. high tide. Enjoy crabbing and sunset views from the dock in spring, summer and fall. Property has 69' of shoreline with 2' at low tide and 4-5' at high tide. Open concept floor plan w/ lots of light and water views. 2 BR, 1.5 bath and bonus

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  • 21481 Indian Bridge Rd, California, MD 20619

    $539,900 Under Contract

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    • 2,924 Sq Ft
    • 21481 Indian Bridge Rd
    • California, MD

    Less than $185 sq ft and No HOA here. 1 acre home that backs to trees. Large deck off the back of the house with private setting. The home has been extremely well kept. Almost 3000 sq ft of living area with 4 bedrooms, 2.5 baths, huge bonus room that could be used as you like, and large 2 car garage. Propane fireplace insert. Paved driveway with ample parking for up to 8 vehicles and turn

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  • 38330 Hatchet Thicket Rd, Avenue, MD 20609

    $260,000 Sold Sep 20, 2024

    • 3 Beds
    • 1 Bath
    • 2,352 Sq Ft
    • 38330 Hatchet Thicket Rd
    • Avenue, MD

    Great for investor, 1st time homebuyer, or flip 3 BR 1 BA home on secluded 3 + acre lot. Home sold as is. Passing septic inspection in hand. Schedule your showing today.

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  • 24140 Wheatherby Dr, Hollywood, MD 20636

    $525,000 Sold May 30, 2025

    • 4 Beds
    • 2.5 Baths
    • 2,450 Sq Ft
    • 24140 Wheatherby Dr
    • Hollywood, MD

    You could be the best of the neighborhood in this beautiful well kept home on one of the largest lots (1.3acres) in the subdivision. Seller has replaced the carpet and doing some touch up painting to make this property pristine and move in ready. Cozy up in the Family Room with the gas fireplace or use as ambience with your beautiful kitchen. 4 Bedrooms, 2.5 Baths, 2 Car Garage with plenty of

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  • 25464 Allston Ln, Hollywood, MD 20636

    $400,000 Sold Sep 23, 2024

    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft
    • 25464 Allston Ln
    • Hollywood, MD

    Very well cared for home in small subdivision in North Hollywood. Newer Kitchen Makeover with quartz counter tops, stainless appliances and soft close cabinets, 2019 New HVAC and Water Heater, Above Ground Pool just 3 years old, and plantation shutters on the inside living room and dining room area. Enter on the main level living room, dining room, and kitchen area. Large Inviting Foyer

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  • 40265 Hidden Meadow Ln, Mechanicsville, MD 20659

    $479,900 Sold May 30, 2025

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • 40265 Hidden Meadow Ln
    • Mechanicsville, MD

    New construction ready to move in April/May timeframe. Renderings are for informational purposes but close to actual product. One level living with a full walkout unfinished basement. Basement has a rough in for future use. Property is on a sloped back woods lot.

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  • 27013 Dogwood Ln, Mechanicsville, MD 20659

    $300,000 Sold Nov 20, 2024

    • 3 Beds
    • 2.5 Baths
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    • 27013 Dogwood Ln
    • Mechanicsville, MD

    Great price on this split foyer with a huge 2 vehicle carport. Home has newer oil burner furnace and oil tank and roof has been replaced within last 5 years. Also a gas wood stove insert on the bottom level to ensure you stay warm. A large laundry room, family room, Full bath with shower, and an office that was being used as a bedroom on the lower level. Upgraded newer carpet within the last

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  • 44457 Three Coves Rd, Hollywood, MD 20636

    $405,000 Sold Jun 30, 2025

    • 3 Beds
    • 2 Baths
    • 1,591 Sq Ft
    • 44457 Three Coves Rd
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    Less than 1 mile (.3 tenths of a mile to be exact) from public boat ramp. One level, 3 BR, 2 BA, Rambler on a full basement. Home has a wood burning fireplace. HVAC less than 10 years old & serviced annually, new hot water heater, kitchen upgrade in 2013, on a great level lot with a 20' x 40' metal barn. This is a great property for someone that does not want to be part of a community and off

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Source: Bright MLS

MLS Number: MDSM2025294

Bright MLS

APN: 03-077160