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Single family home for sale at 14401 Windy Oak Cir, Upper Marlboro, MD 20772 | MLS# MDPG2199126 | Listing updated on 2026-04-18
Photo 1 of Single family home for sale at 14401 Windy Oak Cir, Upper Marlboro, MD 20772 | MLS# MDPG2199126 | Listing updated on 2026-04-18
Photo 2 of Single family home for sale at 14401 Windy Oak Cir, Upper Marlboro, MD 20772 | MLS# MDPG2199126 | Listing updated on 2026-04-18
Photo 3 of Single family home for sale at 14401 Windy Oak Cir, Upper Marlboro, MD 20772 | MLS# MDPG2199126 | Listing updated on 2026-04-18
Photo 4 of Single family home for sale at 14401 Windy Oak Cir, Upper Marlboro, MD 20772 | MLS# MDPG2199126 | Listing updated on 2026-04-18
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$635,000

Monthly Est:$3,161

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,028sqft

14401 Windy Oak Cir, Upper Marlboro, MD 20772

$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 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Prince Georges Md County

  • City

    Upper Marlboro

  • 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

DateEventPrice

04/17/2026

Source: mls_logoBright MLS-NJ #MDPG2199126

Listed for Sale

$635,000 +18.69%

$313/sqft

02/06/2024

Source: mls_logoBright MLS-NJ #MDPG2078460

Price Increased

$535,000 +24.42%

$264/sqft

10/09/2020

Source: mls_logoBright MLS-NJ #MDPG580276

Price Increased

$430,000 +17.81%

$212/sqft

06/30/2011

Source: mls_logoBright MLS-NJ #1004369540

Sold

$365,000

$180/sqft

Getting Around 14401 Windy Oak Cir

Bike Score®

Bike Score

Somewhat Bikeable

3/100

Walk Score®

Walk Score

Car-Dependent

0/100

Data provided by Redfin

Nearby Homes

Based on information from Bright MLS through Oct 09, 2026, 02:30PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

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