14401 Windy Oak Circle Upper Marlboro, MD $ 635,000
14401 Windy Oak Circle
$ 635,000
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14401 Windy Oak Circle

Upper Marlboro, MD, 20772
$ 635,000
Bedrooms3 Baths2.1 Sq 2,028

Monthly Estimate*

$ 3,910

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Single Family Home for sale in Upper Marlboro, MD

for $635,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,028 square foot home was built in 1915 on a lot size of 2.23.

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 osmosisoffering 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 optionalityspace to expand, space to create, and space to unwind. A setting that offers a sense of retreat while remaining connected to the regions most desirable destinations. For those seeking land, privacy, and a thoughtfully updated home, 14401 Windy Oak Circle represents a turnkey opportunity with enduring appeal.

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Single Family Active

Price

$ 635,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 4,725

Style

Colonial,Farmhouse/National Folk

Lot Size

2.23

Year Built

1915

Town/City

Upper Marlboro

County/Region

Prince Georges

MLS | Web ID

MDPG2199126

Features
General
Living Area 2028
Sewer On Site Septic Private Septic Tank
Heating Forced Air Heat Pump(s) Pellet Stove Heat Pump - Electric BackUp Humidifier Zoned
Cooling Central A/C Ceiling Fan(s)
Possession Settlement 0-30 Days CD 31-60 Days CD
Roof Architectural Shingle
Appliances Oven - Wall Dishwasher Dryer Refrigerator Washer Water Heater Oven - Single Stainless Steel Appliances
Zoning RE
Patio/Porch Features Porch(es) Deck(s)
Architectural Style Colonial Farmhouse/National Folk
Security Features Security System
Construction Materials Frame
School District PRINCE GEORGE'S COUNTY PUBLIC SCHOOLS
Year Built 1915
View Trees/Woods
Levels 3
Tax Year 2023
Ownership Fee Simple
Cool Fuel Electric
Accessibility None
County PRINCE GEORGES
New Construction N
Property Type Residential
HOA N
Subdivision Name WINDY OAKS
Facing Direction East
Garage Y/N N
Water Access Y/N N
Other Structures Above Grade Below Grade
Full Baths 2
Status ACTIVE
Directions Heading south on Croom Rd take a right onto Wind Oak Drive. Take another right at the T intersection Windy Oak Circle. The house will be the first home on the left sitting on top of the hill.
City UPPER MARLBORO
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 97139.00
Tax Annual Amount 4725.0
Property Condition Very Good
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 0
Bathrooms Count Main Level 1.00
Price Per Sq Ft Total AG 313.12
Acceptable Financing Conventional FHA VA Cash
Vacation Rental Y/N N
Virtual Tour https://youtu.be/GeVDjM2n3ew
Location Type Rural
Standard Status Active
Year Built Source Assessor
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Interior
Interior Amenities 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
Heating Fuel Electric Propane - Leased
Basement Outside Entrance Daylight Partial Heated Interior Access Partial Poured Concrete Sump Pump Unfinished Walkout Stairs
Flooring Hardwood Ceramic Tile
Total Fireplaces 2
Fireplace Features Wood Other
Hot Water Electric
Basement (Y/N) Y
Heating Y/N Y
Window Features Double Hung Screens Skylights
Fireplace Y/N Y
Above Grade Finished Area 2028
Half Baths 1
Central Air Y/N Y
Total Bedrooms 3
Below Grade Finished Area 0
Room Type Living Room Dining Room Primary Bedroom Bedroom 2 Bedroom 3 Kitchen Laundry Bathroom 2 Primary Bathroom
Below Grade Finished Area Unit Type Square Feet
Laundry Type Main Floor
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 3
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Exterior
Exterior Amenities Outbuilding(s)
Pool No Pool
Parking Features Asphalt Driveway
Lot Features Backs to Trees Cleared Front Yard Landscaping Open Partly Wooded Private Secluded
Water Source Well
Inclusions see documents for inclusions/exclusions
Type of Parking Driveway
Foundation Details Other
Water View Y/N N
Lot Size Acres 2.23
Lot Size Source Assessor
Waterfront Y/N N
Land Assessed Value 122300.00
Navigable Water Y/N N
Water Oriented Y/N N
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Internal Only
Street Number 1 14401
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* Excluded Features
List By
Ttr Sotheby's International Realty

Broker

brad.kappel@sothebysrealty.com

Email

Affordability Calculator

$4,304
Per Month
91%
9%
0%
Monthly Principal & Interest
$3,910
Monthly Property Taxes
$394
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3533425 Elementary School
3533254 Middle School
Frederick Douglass High School High School
Pricing History
DatePricePrice ChangeDescription
4/18/2026$635,000 Listed Price

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14401 Windy Oak Circle, Upper Marlboro, MD, 20772 is a Single Family Home for sale at $635,000 with 2,028 sqft and a lot size of 2.23. 14401 Windy Oak Circle has 3 bedrooms, 2.1 baths, and was built in 1915. The property's zip code is 20772 which is in Upper Marlboro, MD