14401 Windy Oak Cir, Upper Marlboro, MD 20772
Local realty services provided by:CENTURY 21 Charles Smith Agency, Inc.
14401 Windy Oak Cir,Upper Marlboro, MD 20772
$645,000
- 3 Beds
- 3 Baths
- - sq. ft.
- Single family
- Sold
Listed by: bradley r kappel, christian schou
Office: ttr sotheby's international realty
MLS#:MDPG2199126
Source:BRIGHTMLS
Sorry, we are unable to map this address
Price summary
- Price:$645,000
About this home

Set on 2.23 private acres in Upper Marlboro, 14401 Windy Oak Circle presents a rare opportunity to enjoy space, privacy, and versatility without sacrificing proximity to Washington, D.C. and Annapolis.
Originally rooted in classic farmhouse character, the home was thoughtfully reimagined in 2019 with a generously sized addition, updated mechanical systems, and refined finishes that support modern living. The result is a warm and inviting three-bedroom, two-and-a-half-bath residence that feels both timeless and move-in ready. Recent upgrades include a new roof, solar panels, a brand-new HVAC system, and a water softener with reverse osmosis—offering both peace of mind and lasting value.
Inside, the layout is intuitive and highly livable, with a natural flow between spaces that supports both everyday living and entertaining.
Outdoors, the property truly distinguishes itself. The 2.23 acres of usable land offer flexibility for a variety of lifestyles, while an expansive rear deck creates an ideal setting for gatherings, outdoor dining, or quiet evenings. The well-maintained grounds provide endless opportunities for recreation, gardening, or future expansion.
The barn introduces an additional layer of utility and possibility, well-suited for storage, workshop use, or hobby farming, and adaptable to meet a range of needs depending on your lifestyle.
This is a property defined by optionality—space to expand, space to create, and space to unwind. A setting that offers a sense of retreat while remaining connected to the region’s most desirable destinations.
For those seeking land, privacy, and a thoughtfully updated home, 14401 Windy Oak Circle represents a turnkey opportunity with enduring appeal....
Contact an agent
Home facts
- Year built:1915
- Listing ID #:MDPG2199126
- Added:44 day(s) ago
- Updated:June 01, 2026 at 05:58 AM
Rooms and interior
- Bedrooms:3
- Total bathrooms:3
- Full bathrooms:2
- Half bathrooms:1
- Flooring:Ceramic Tile, Hardwood
- Dining Description:Dining Area, Dining Room, Formal/Separate Dining Room
- Bathrooms Description:Bathroom 2, Primary Bath(s), Primary Bathroom
- Kitchen Description:Built-Ins, Dishwasher, Kitchen - Eat-In, Kitchen - Island, Kitchen - Table Space, Oven - Single, Oven - Wall, Pantry, Refrigerator, Stainless Steel Appliances, Water Heater
- Bedroom Description:Primary Bedroom
- Basement:Yes
- Basement Description:Daylight, Heated, Interior Access, Outside Entrance, Partial, Poured Concrete, Sump Pump, Unfinished, Walkout Stairs
Heating and cooling
- Cooling:Ceiling Fan(s), Central A/C
- Heating:Electric, Forced Air, Heat Pump - Electric BackUp, Heat Pump(s), Humidifier, Propane - Leased, Zoned
Structure and exterior
- Roof:Architectural Shingle
- Year built:1915
- Lot Features:Backs to Trees, Cleared, Front Yard, Landscaping, Open, Partly Wooded, Private, Rural, Secluded
- Architectural Style:Colonial, Farmhouse/National Folk
- Construction Materials:Frame
- Exterior Features:Deck(s), Outbuilding(s), Porch(es)
- Levels:3 Story
Schools
- High school:FREDERICK DOUGLASS
- Middle school:GWYNN PARK
- Elementary school:MATTAPONI
Utilities
- Water:Well
- Sewer:On Site Septic, Private Septic Tank
Finances and disclosures
- Price:$645,000
- Tax amount:$4,725 (2023)
Features and amenities
- Laundry features:Dryer, Laundry, Washer
- Amenities:Built-Ins, Ceiling Fan(s), Double Hung Windows, Security System
Parking
- Parking description:Asphalt Driveway
New listings near 14401 Windy Oak Cir
- Coming SoonOpen Sat, 1 to 3pm
$425,000Coming Soon5 beds 3 baths5014 Woodford Ln, UPPER MARLBORO, MD 20772
MLS# MDPG2201840Listed by: COMPASS - New
$400,000Active2 beds 2 baths1,469 sq. ft.13407 Leesburg Place, UPPER MARLBORO, MD 20774
MLS# MDPG2205132Listed by: FAB REALTY LLC - Open Sat, 11am to 1pmNew
$599,999Active5 beds 4 baths2,073 sq. ft.13952 Bishops Bequest Rd, UPPER MARLBORO, MD 20772
MLS# MDPG2205170Listed by: OWN REAL ESTATE - Open Sat, 1 to 3pmNew
$419,900Active3 beds 3 baths1,790 sq. ft.10720 Presidential Pkwy, UPPER MARLBORO, MD 20772
MLS# MDPG2205202Listed by: SAMSON PROPERTIES - Coming Soon
$434,000Coming Soon3 beds 4 baths8700 Sweet Lauren Ct, UPPER MARLBORO, MD 20772
MLS# MDPG2205186Listed by: OWN REAL ESTATE - New
$825,000Active4 beds 4 baths5,049 sq. ft.3602 Winterbourne Dr, UPPER MARLBORO, MD 20774
MLS# MDPG2204812Listed by: WEICHERT, REALTORS - New
$205,000Active2 beds 1 baths894 sq. ft.13560 Lord Sterling Pl #9-4, UPPER MARLBORO, MD 20772
MLS# MDPG2205166Listed by: WEICHERT, REALTORS - Coming Soon
$425,000Coming Soon3 beds 2 baths3907 91st Ave, UPPER MARLBORO, MD 20774
MLS# MDPG2205126Listed by: SAMSON PROPERTIES - New
$194,999Active2 beds 2 baths1,071 sq. ft.10239 Prince Pl #26-102, UPPER MARLBORO, MD 20774
MLS# MDPG2205134Listed by: SAMSON PROPERTIES - New
$1,500,000Active1.28 Acres15109 Marlboro Pike, UPPER MARLBORO, MD 20772
MLS# MDPG2205094Listed by: SAMSON PROPERTIES