Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$635,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,572 Sq. Ft.
  • Updated 1 day ago

Next open house:

Open House: 12:00 PM - 2:00 PM

Saturday 4/25 12:00 PM - 2:00 PM

14401 Windy Oak Circle,Upper Marlboro, MD 20772

14401 Windy Oak CircleUpper MarlboroMD20772

Get directions
See This Home
Save This Home
See This Home
Save This Home
14401 Windy Oak Circle, Upper Marlboro, MDVideo Tour of 14401 Windy Oak Circle, Upper Marlboro, MD.
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.

Full Property Details for 14401 Windy Oak Circle

General

  • Price: $635,000
  • Taxes: $4,725 (2023)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDPG2199126
  • Updated: 4/17/2026
  • Added to Site: 2 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Laundry, Bathroom 2, Primary Bathroom
  • 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
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Wood, Other
  • Appliances: Oven - Wall, Dishwasher, Dryer, Refrigerator, Washer, Water Heater, Oven - Single, Stainless Steel Appliances
  • Flooring: Hardwood, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 3

Other Rooms

  • Laundry: Main Floor

Additional Information

  • Security/Safety: Security System

Exterior

  • Exterior Features: Outbuilding(s)
  • Porch/Patio/Deck: Porch(es), Deck(s)

Parking

  • Parking Features: Asphalt Driveway
  • Parking Type: Driveway

Location

  • County: PRINCE GEORGES
  • Subdivision: WINDY OAKS
  • Driving 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.
  • Direction Faces: East
  • Location Details: Rural

School Information

  • School District: Prince George's County Public Schools
  • Elementary School: Mattaponi
  • Middle School: Gwynn Park
  • High School: Frederick Douglass

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Ceiling Fan(s)
  • Cooling Fuel: Electric
  • Heating Type: Forced Air, Heat Pump(s), Pellet Stove, Heat Pump - Electric BackUp, Humidifier, Zoned
  • Heating Fuel: Electric, Propane - Leased
  • Water Heater: Electric

Utilities

  • Sewer: On Site Septic, Private Septic Tank
  • Water: Well

Structural Information

  • Architectural Style: Colonial, Farmhouse/National Folk
  • Structure Type: Detached
  • Construction: Frame
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Outside Entrance, Daylight, Partial, Heated, Interior Access, Partial, Poured Concrete, Sump Pump, Unfinished, Walkout Stairs
  • Foundation: Other
  • Roof: Architectural Shingle
  • Windows: Double Hung, Screens, Skylights
  • Stories Description: Main, Upper 1
  • Square Feet: 2,572
  • Sq. Ft. Source: Assessor
  • Living Area: 2,028 Sq. Ft.
  • Finished Above Grnd: 2,028 Sq. Ft.
  • Year Built: 1915
  • Year Built Source: Assessor
  • Property Condition: Very Good

Additional Structures

  • Other Structures: Storage Barn/Shed

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 2.23
  • Lot Size (Sq. Ft.): 97,139
  • Lot Size Source: Assessor
  • Zoning: RE
  • Lot Description: Backs to Trees, Cleared, Front Yard, Landscaping, Open, Partly Wooded, Private, Secluded

Financial Considerations

  • Price Per Sq. Ft.: $313.12
  • Assessment Year: 2023
  • City/TownTax Freq: Annually
  • County Tax: $3,393
  • County Tax Freq: Annually
  • Tax w/Assessment: $344,900
  • Tax Amount: $4,725
  • Tax Year: 2023
  • Tax Total Finished Sq. Ft.: 2028

Disclosures and Reports

  • Ownership: Fee Simple
  • Inclusions: see documents for inclusions/exclusions

Listed by TTR Sotheby's International Realty, Bradley R Kappel and TTR Sotheby's International Realty, Christian Schou

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agents

— 14401 Windy Oak Circle —

  • Bradley R Kappel

    TTR Sotheby's International Realty

  • Christian Schou

    TTR Sotheby's International Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 14401 Windy Oak Circle

School District:Prince George's County Public Schools
NameGradesDistance
Mattaponi Elementary School
11701 Duley Station Road, Upper Marlboro, MD 20772
K-52.8 mi
Gwynn Park Middle School
8000 Dyson Road, Brandywine, MD 20613
6-87.2 mi
Frederick Douglass High School, Upper Marlboro, MD
8000 Croom Road, Upper Marlboro, MD 20772
9-121.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 14401 Windy Oak Circle Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/17/2026
Listed
$635,000
18.69%
MLS
2/05/2024
Sold
$535,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 14401 Windy Oak Circle

Year
Property Taxes
Change
Tax Assessment
Change
2023
$3,835
—
$401,500
8%
2023
$3,835
—
$373,200
8%
2023
$3,835
9%
$344,900
9%
2022
$3,521
-28%
$316,600
—
2019
$4,862
212%
$316,600
—
2021
$1,560
-69%
$316,600
-7%
2020
$5,057
10%
$339,500
11%
2019
$4,586
11%
$306,933
12%
2018
$4,116
13%
$274,367
13%
2017
$3,646
6%
$241,800
4%
2016
$3,426
6%
$232,900
4%
2015
$3,221
3%
$224,000
4%
2014
$3,142
—
$215,100
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 14401 Windy Oak Circle

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by TTR Sotheby's International Realty, Bradley R Kappel and TTR Sotheby's International Realty, Christian Schou

Similar Properties near 14401 Windy Oak Circle

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

16601 Candy Hill Rd, Upper Marlboro, MD 20772 - Photo 1
$625,000
Open House

16601 Candy Hill Rd  Upper Marlboro, MD 20772

  • Single Family
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 2,461
    Sq. Ft.
Listed by Weichert Realtors - Blue Ribbon, Thomas Allotta
13245 Croom Rd, Upper Marlboro, MD 20772 - Photo 1 Price Reduced
-$4,909 (-0.73%)
$665,000

13245 Croom Rd  Upper Marlboro, MD 20772

  • Single Family
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 2,900
    Sq. Ft.
Listed by Realty Navigator, Vincent J Payne and Realty Navigator, Petra Quinn
5742 Brooks Woods Rd, Lothian, MD 20711 - Photo 1
$639,900
Open House

5742 Brooks Woods Rd  Lothian, MD 20711

  • Single Family
  • Under Contract
  • 3
    Beds
  • 2
    Total Baths
  • 1,586
    Sq. Ft.
Listed by TTR Sotheby's International Realty, Erica K Baker
5101 Back Stretch Blvd, Upper Marlboro, MD 20772 - Photo 1
$659,000
Open House

5101 Back Stretch Blvd  Upper Marlboro, MD 20772

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,510
    Sq. Ft.
Listed by Fairfax Realty Select, Nadja Latchinian

Just Listed near 14401 Windy Oak Circle

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

9902 Angora Dr, Cheltenham, MD 20623 - Photo 1 Just Listed
$599,000

9902 Angora Dr  Cheltenham, MD 20623

  • Single Family
  • Active
  • Updated 13 hours ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,840
    Sq. Ft.
Listed by EXP Realty, LLC, Jonathan S Lahey and EXP Realty, LLC, Jennifer Chang
65 Cob Ct, Lothian, MD 20711 - Photo 1 Just Listed
$85,000

65 Cob Ct  Lothian, MD 20711

  • Mobile Home
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,200
    Sq. Ft.
Listed by RE/MAX Realty Group, Daniel Garcia
7209 Donnell Pl, District Heights, MD 20747 - Photo 1 Just Listed
$97,000
Open House

7209 Donnell Pl  #AA-7  District Heights, MD 20747

  • Condo
  • Active
  • Updated 3 days ago
  • 1
    Bed
  • 1
    Total Bath
  • 678
    Sq. Ft.
Listed by Keller Williams Capital Properties, Yvonne T Lee II
7602 Kipling Pkwy, District Heights, MD 20747 - Photo 1 Just Listed
$425,000

7602 Kipling Pkwy  District Heights, MD 20747

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,104
    Sq. Ft.
Listed by TTR Sotheby's International Realty, Melissa Terzis

Price Reduced near 14401 Windy Oak Circle

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

no-photo Coming Soon
$1,500,000
Open House

10613 Frank Tippett Rd  Cheltenham, MD 20623

  • Single Family
  • Coming Soon
  • 5
    Beds
  • 6
    Total Baths
  • 7,956
    Sq. Ft.
Listed by Sovereign Home Realty, Delores M Gassaway
10700 Wembrough Pl, Cheltenham, MD 20623 - Photo 1 Price Reduced
-$20,000 (-3.39%)
$569,900

10700 Wembrough Pl  Cheltenham, MD 20623

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,006
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., Pennye Green and Long & Foster Real Estate, Inc., Nadia Aminov
1174 Wrighton Rd, Lothian, MD 20711 - Photo 1 Price Reduced
-$5,000 (-14.29%)
$30,000

1174 Wrighton Rd  Lothian, MD 20711

  • Single Family
  • Active
  • Updated 2 days ago
  • 816
    Sq. Ft.
Listed by Ashland Auction Group LLC, Adam M Shpritz and Ashland Auction Group LLC, Lee M Shpritz
5485 Solomons Island Rd, Lothian, MD 20711 - Photo 1 Price Reduced
-$100 (-0.01%)
$728,900

5485 Solomons Island Rd  Lothian, MD 20711

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 3,841
    Sq. Ft.
Listed by Keller Williams Flagship, Christopher Staub

Recent Sales near 14401 Windy Oak Circle

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

12216 Westview Dr, Upper Marlboro, MD 20772 - Photo 1 Sold
$550,000

12216 Westview Dr  Upper Marlboro, MD 20772

  • Single Family
  • Closed
  • 6
    Beds
  • 3
    Total Baths
  • 3,180
    Sq. Ft.
Listed by Keller Williams Preferred Properties, Katrina O Benjamin
Sold by HomeSmart, Tamika E Brooks
10107 Grandhaven Ave, Upper Marlboro, MD 20772 - Photo 1 Sold
$615,000

10107 Grandhaven Ave  Upper Marlboro, MD 20772

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 4,856
    Sq. Ft.
Listed by RE/MAX United Real Estate, Donald L. Frederick
Sold by Long & Foster Real Estate, Inc., Michael P Mason
10208 Running Brook Ln, Upper Marlboro, MD 20772 - Photo 1 Sold
$555,000

10208 Running Brook Ln  Upper Marlboro, MD 20772

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 3,122
    Sq. Ft.
Listed by Samson Properties, DANIELLE SCOTT WILEY
Sold by Tower Executives Realty, Adesoji B Adewole
8405 Hardwick Ct, Upper Marlboro, MD 20772 - Photo 1 Sold
$700,000

8405 Hardwick Ct  Upper Marlboro, MD 20772

  • Single Family
  • Closed
  • Updated 1 day ago
  • 6
    Beds
  • 4
    Total Baths
  • 5,389
    Sq. Ft.
Listed by Amber & Company Real Estate, Wesley C Howard

14401 Windy Oak Circle, Upper Marlboro, MD 20772 (MLS# MDPG2199126) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 14401 Windy Oak Circle is currently listed for $635,000 and was received on April 17, 2026. Want to learn more about 14401 Windy Oak Circle? Do you have questions about finding other Single Family real estate for sale in Upper Marlboro? You can browse all Upper Marlboro real estate or contact a Coldwell Banker agent to request more information.

Tour this property