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- Description
- Property Details
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$635,000
Monthly Est:$3,161
3 Beds
- 3 Baths
2 full baths + 1 half bath
2,028sqft
14401 Windy Oak Cir, Upper Marlboro, MD 20772
$635,000
$3,161/moEst:
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Single Family Residence
Built in 1915
$-- HOA
2.23 acres lot
$313/sq.ft
Description
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.
- Houzeo last checked: 10 hours ago
- Listing updated: April 18, 2026 at 2:16 am
- Listing Provided by: Bradley R Kappel (410) 279-9476 , Christian Schou (443) 926-4509 | TTR Sotheby's International Realty (410) 280-5600
- Source: Bright MLS-NJ | MLS#: MDPG2199126

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1915
HOA Fees
-
Finished Area
2,028 sqft
Lot Size
2.23 acres lot
Basement Area
- sqft
MLS Name
Bright MLS
MLS Number
MDPG2199126
MLS Status
ACTIVE-BRIGHT
Days on Market
1

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 3
Bathrooms: 3
Interior
Heating
Forced Air, Heat Pump(s), Pellet Stove, Heat Pump Electric Back Up, Humidifier, Zoned
Appliances
Oven Wall, Dishwasher, Dryer, Refrigerator, Washer, Water Heater, Oven Single, Stainless Steel Appliances
Window Features
Double Hung, Screens, Skylights
Interior Features
Built Ins, Ceiling Fan(s), Dining Area, Floor Plan Traditional, Formal/separate Dining Room, Kitchen Eat In, Kitchen Island, Kitchen Table Space, Pantry, Primary Bath(s), Wood Floors
Flooring
Hardwood, Ceramic Tile
Cooling
Central A/c, Ceiling Fan(s)
Exterior Features
Outbuilding(s)
Sewer
On Site Septic, Private Septic Tank
Construction
Year Built
Year Built: 1915
Home type
Single Family Residence
Property Condition
Very Good
Foundation Details
Other
Construction Materials
Frame
Architectural Style
Colonial, Farmhouse/national Folk
Roof
Architectural Shingle
Utilities & Energy
Parking Features
Asphalt Driveway
Security Features
Security System
Basement
Outside Entrance, Daylight, Partial, Heated, Interior Access, Partial, Poured Concrete, Sump Pump, Unfinished, Walkout Stairs
Fireplace Features
Wood, Other
Water Source
Well
Other Features
Patio And Porch Features
Porch, Deck
Subdivision Name
Windy Oaks
Lot Features
Backs To Trees, Cleared, Front Yard, Landscaping, Open, Partly Wooded, Private, Secluded
Price History
| Date | Event | Price |
|---|---|---|
04/17/2026 Source: | Listed for Sale | $635,000 +18.69% $313/sqft |
02/06/2024 Source: | Price Increased | $535,000 +24.42% $264/sqft |
10/09/2020 Source: | Price Increased | $430,000 +17.81% $212/sqft |
06/30/2011 Source: | Sold | $365,000 $180/sqft |
Getting Around 14401 Windy Oak Cir
Bike Score®
Somewhat Bikeable
3/100
Walk Score®
Car-Dependent
0/100
Data provided by Redfin
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