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.
2,028 Sq Ft
2.23 Private Acres Lot Size
other
$394 Monthly Tax
Built in 1915
MLS/Listing ID MDPG2199126
Cooling - Ceiling Fans
Cooling - Central Air
Construction - Frame
Style - Colonial
Dishwasher
Stainless Steel Appliance(s)
Ceiling Fans
Lot - Partly Wooded
Dryer
Refrigerator
Washer
Water Heater
Double Hung
Screens
Lot - Cleared
Lot - Front Yard
Lot - Private
Lot - Secluded
Dining Area
Fireplace
Hardwood
Ceramic Tile
Heating - Electric
Pantry
Skylights
Septic System
Well
Out Buildings
Kitchen Island
The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the BrightMLS. Real estate listings held by brokerage firms other than Douglas Elliman of VA are marked with the Internet Data Exchange logo and information about them includes the name of the listing brokers. Some properties listed with the participating brokers do not appear on this website at the request of the seller. Listings of brokers that do not participate in Internet Data Exchange do not appear on this website.
All information deemed reliable but not guaranteed. Last date updated: 06/23/2026.
Source: Bright Multiple Listing Service, Inc.
© 2026 Bright Multiple Listing Service, Inc. All rights reserved.