14401 Windy Oak Circle, Upper Marlboro, MD 20772Asking Price of: $635,000

Property Search Compliments of
Berkshire Hathaway HomeServices Homesale Realty

Primary property photo for 14401 Windy Oak Circle

View full listing details at http://www.homesale.com/lid=186074485

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.

Property Details

Address: 14401 Windy Oak Circle, Upper Marlboro, MD 20772
Bedrooms: 3
Bathrooms: 2 full1 partial
Size: 2,028 square feet
Type: Colonial,Farmhouse/National Folk
Subdivision: WINDY OAKS
Area: UPPER MARLBORO
School District: PRINCE GEORGES COUNTY PUBLIC SCHOOLS
MLS ID: MDPG2199126
Status: ACTIVE UNDER CONTRACT

Property School Information

High School: FREDERICK DOUGLASS
Middle School: GWYNN PARK
Elementary School: MATTAPONI
School District: PRINCE GEORGES COUNTY PUBLIC SCHOOLS

Property Features

Taxes: $4,725
Basement: Yes
Wooded: Yes
Roof Type: Architectural Shingle
Exterior: Frame
Special View Info: Trees/Woods
Lot Size: 2.23 Acres
Lot Dimensions: 2.23 Acre(S)
Heating: Forced Air,Heat Pump(s),Pellet Stove,Heat Pump - E
Fuel Type: Electric,Propane - Leased
Cooling: Central A/C,Ceiling Fan(s)
Year Built: 1915
Fireplaces: 2
Water: Well
Sewer: On Site Septic,Private Septic Tank
Stories: 3.0
Additional Structures: Above Grade,Below Grade
Location Description: Rural
Lot Description: Backs to Trees, Cleared, Front Yard, Landscaping, Open, Partly Wooded, Private, Secluded
Structure Type: Detached
Parking Features: Asphalt Driveway
Appliances: Oven - Wall,Dishwasher,Dryer,Refrigerator,Washer,Water Heater,Oven - Single,Stainless Steel Appliances
Rooms: Living Room,Dining Room,Primary Bedroom,Bedroom 2,Bedroom 3,Kitchen,Laundry,Bathroom 2,Primary Bathroom
Basement: Outside Entrance,Daylight, Partial,Heated,Interior Access,Partial,Poured Concrete,Sump Pump,Unfinished,Walkout Stairs
SQFT Total Finished: 2028
SQFT Above Finished: 2028
Exterior: Outbuilding(s)
Interior: 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
Fireplace: Wood,Other
Flooring: Hardwood,Ceramic Tile
Windows: Double Hung,Screens,Skylights

Property information as of Wednesday, April 22, 2026 at 12:29 AM America/New_York

Listed By

Agency Name: TTR Sotheby's International Realty
Agency Phone: 4102805600

Shown By

Agency Title: Berkshire Hathaway HomeServices Homesale Realty
Agency Phone: +18003833535

Real estate agents ready to serve you | Browse homes and real estate for sale

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/22/2026. The listing information on this page last changed on 04/22/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 04/22/2026 12:00:03 AM EST) or Bright MLS (last updated Tue 04/21/2026 11:49:46 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
Privacy Policy / DMCA Notice / ADA Accessibility

Corporate Office - 215 S Centerville Rd. Lancaster, PA 17603
James J Hafer - West Virginia Broker of Record

©2026 BHH Affiliates, LLC. An independently owned and operated franchisee of BHH Affiliates, LLC. Berkshire Hathaway HomeServices and the Berkshire Hathaway HomeServices symbol are registered service marks of Columbia Insurance Company, a Berkshire Hathaway affiliate. Equal Housing Opportunity.

Sitemap