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$399,000

  • For Sale
  • Active
  • Townhouse
  • 3 Beds
  • 2 Full Baths
  • 2,008 Sq. Ft.
  • 2 Car Garage
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A rare townhouse find in coveted Whispering Pines! This single-level three-bedroom, two-full-bath townhome has been exceptionally maintained by the original owners. The open floor plan of the living and dining area offers a flexible layout and design options, complete with a built-in bookcase and a gas fireplace. The eat-in kitchen has a large bay window, tile floors, ample countertop space, plenty of storage and French doors leading to the bonus ''Carolina'' room. The large primary bedroom has an en-suite bath with a walk-in shower, separate commode closet, and a nicely sized walk-in closet. The second full bathroom features tile floors, a bathtub/shower combination and a linen closet for additional storage. Both bathrooms have solar tubes which bring in great natural light. Other features include: a private concrete back patio with a retractable awning, pull-down stairs in the two car garage to access bonus attic storage space. Mechanical updates: New roof installed in 2024 New 3-ton Trane air conditioner and gas furnace installed in 2023 with extended warranties Septic pumped in 2025 Enjoy a true lock-and-leave lifestyle in a tight-knit community. Whispering Winds HOA takes care of the landscaping and lawn maintenance as part of your HOA dues, allowing you more time to relax and enjoy the area. This exceptional property also boasts an unbeatable location. Conveniently situated just 10 minutes from Pinehurst Resort -- known as the ''Home of American Golf'' -- and only a few miles from the fine dining, boutique shopping, and entertainment of Southern Pines. For active-duty military families, 33 Winding Trail is located less than 30 minutes from Fort Bragg. For weekend getaways, you are approximately 2.5 hours from both the Appalachian Mountains and the beautiful North Carolina coast. Don't miss this opportunity--schedule your showing today!

Full Property Details for 33 Winding Trail

General

  • Price: $399,000
  • HOA FEE: $250/month
  • HOA FEE FREQ.: Annually
  • Taxes: $2,219 (2026)
  • Status: Active
  • Type: Townhouse
  • Source: 2253
  • MLS ID: 100576112
  • Updated: 5/26/2026
  • Added to Site: 45 day(s) ago

Interior

  • Number of Rooms: 8
  • Interior Features: Master Downstairs, Walk-in Closet(s), Tray Ceiling(s), High Ceilings, Entrance Foyer, Ceiling Fan(s), Blinds/Shades, Walk-In Closet(s)
  • Appliances: Built-In Microwave, Refrigerator, Dishwasher, Electric Range
  • Furnishings: Negotiable
  • Flooring: Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Living Area

Additional Information

  • Shared Amenities: Maintenance Common Areas, Maintenance Grounds, Management

Exterior

  • Porch/Patio/Deck: Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking Features: Garage Faces Front, Concrete, Garage

Location

  • County: Moore
  • Subdivision: Whispering Winds
  • Driving Directions: US HWY 1N: Take second exit for HWY 2 (Midland Rd), follow around and exit right at the traffic circle onto Airport Rd. Left onto Lavender Dr, Right onto Winding Trail. Around curve to the left, home on left hand side.

School Information

  • High School District: Moore County Schools
  • Elementary School: McDeeds Creek Elementary
  • Middle School: New Century Middle
  • High School: Union Pines High

Community

  • Association: Yes
  • Assoc. Name: Whispering Winds HOA

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Central Air, Ceiling Fan(s), Heat Pump
  • Heating Type: Propane, Gas Pack, Heat Pump, Fireplace(s), Electric, Forced Air

Utilities

  • Sewer: Septic Tank, Shared Septic
  • Water: Public
  • Utility Description: Cable Available, Water Connected, High Speed Internet

Structural Information

  • Structure Type: Townhouse, Wood Frame, Stick Built
  • Construction: Brick, Brick Veneer, Wood Frame
  • Roof: Shingle, Composition
  • Entry Floor Number: 1
  • Square Feet: 2,008
  • Year Built: 2004

Lot Features

  • Frontage: Maintained, City Street, State Road, Paved, Paved
  • Lot Features: Interior Lot
  • Zoning: RM
  • Fencing (Description): None

Financial Considerations

  • For Sale: Yes
  • Price Per Sq. Ft.: $198.71
  • Association Fee: $3,000
  • Assoc Fee Freq.: Annually
  • Assessment Amount: $332,450
  • Tax Amount: $2,219.11
  • Tax Year: 2026
  • Terms: Cash, Conventional, FHA, USDA Loan, VA Loan

Disclosures and Reports

  • Special Conditions: Standard
  • Legal Description: WHISPERING WINDS UNIT 6 TWNH
  • Property ID: 97000444

Listed by Keller Williams Pinehurst, Tony Barnes

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Listing agent

— 33 Winding Trail —

  • Tony Barnes

    Keller Williams Pinehurst

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 33 Winding Trail

School District:Moore County Schools
NameGradesDistance
McDeeds Creek Elementary
2953 Camp Easter Road, Southern Pines, NC 28387
K-52.4 mi
New Century Middle School
1577 Union Church Road, Cameron, NC 28326
6-85.4 mi
Union Pines High School
1981 Union Church Road, Cameron, NC 28326
9-125 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 33 Winding Trail Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/26/2026
Listed
$399,000
96.55%
MLS
1/28/2005
Sold
$203,000
—
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 33 Winding Trail

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,335
2%
$332,450
—
2023
$2,286
3%
$332,450
49%
2022
$2,227
-2%
$223,830
—
2021
$2,283
6%
$223,830
—
2020
$2,147
4%
$223,830
5%
2019
$2,059
12%
$213,000
—
2016
$1,842
—
$213,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Keller Williams Pinehurst, Tony Barnes

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33 Winding Trail, Whispering Pines, NC 28327 (MLS# 100576112) is a Townhouse property with 3 bedrooms and 2 full bathrooms. 33 Winding Trail is currently listed for $399,000 and was received on May 26, 2026. Want to learn more about 33 Winding Trail? Do you have questions about finding other Townhouse real estate for sale in Whispering Pines? You can browse all Whispering Pines real estate or contact a Coldwell Banker agent to request more information.

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