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$540,000 -$10,000 (-1.82%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,500 Sq. Ft.
  • 0.49 Acres
  • 2 Car Garage
  • Updated 11 hours ago
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Don't miss this incredible opportunity to own a beautifully updated home in one of the Sandhills' most beloved communities -- Whispering Pines! This stunning 2-story home has been thoughtfully updated from top to bottom since 2023 -- just move in and enjoy! The heart of the home is a beautifully remodeled kitchen (2025) featuring brand new GE Café appliances (2025), perfect for the home chef and entertainer alike. The open and inviting floor plan includes a spacious primary suite on the main level, a living room with soaring cathedral ceilings and a cozy fireplace, a formal dining room, and a charming Carolina/Bonus Room that overlooks the backyard and opens directly outside -- seamlessly blending indoor and outdoor living. Upstairs, three additional bedrooms offer space for family or guests, plus a versatile bonus room perfect for a home office, playroom, or extra storage. The upgrades speak for themselves -- brand new roof (2026, warranty transfers), freshly painted interior (2026), resodded backyard (2026), solar panels (2025, warranty transfers), remodeled kitchen with GE Café appliances (2025), all new flooring (2023), and both HVAC systems replaced (2023). A Level 2 EV charger is already in place, and the backyard patio is an entertainer's dream. The trampoline and playset convey! Please see MLS documents for solar panel installation details and cost-saving information. Whispering Pines residents enjoy access to scenic lakes, parks, trails, and three public golf courses. Conveniently located near Fort Bragg, Downtown Southern Pines, the Village of Pinehurst, schools, shopping, dining, and more. With this level of investment and transferable warranties, this one won't last long -- schedule your showing today!

Full Property Details for 39 Winding Trail

General

  • Price: $540,000
  • HOA FEE: $6/month
  • HOA FEE FREQ.: Annually
  • Taxes: $3,063 (2024)
  • Status: Active
  • Type: Single Family
  • Source: 2253
  • MLS ID: 100572040
  • Updated: 5/20/2026
  • Added to Site: 13 day(s) ago

Interior

  • Number of Rooms: 9
  • Interior Features: Master Downstairs, Walk-in Closet(s), Vaulted Ceiling(s), High Ceilings, Whirlpool, Ceiling Fan(s), Pantry, Walk-in Shower, Blinds/Shades, Gas Log, Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Gas Log
  • Appliances: Built-In Microwave, Refrigerator, Range, Disposal, Dishwasher, Convection Oven
  • Flooring: Carpet, Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Living Area

Other Rooms

  • Laundry: Dryer Hookup, Washer Hookup

Additional Information

  • Shared Amenities: Trash
  • Security/Safety: Smoke Detector(s)

Exterior

  • Porch/Patio/Deck: Patio, Front Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking Features: Concrete, Off Street

Location

  • County: Moore
  • Subdivision: Whispering Winds
  • Driving Directions: Airport Rd towards Niagra-Carthage Rd. Left into Whispering Winds subdivision on Lavendar Drive. Take immediate right onto Winding Trail. 39 Winding Trail is on the left.

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 Lake Owners Association

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Central Air, Heat Pump
  • Heating Type: Propane, Heat Pump, Fireplace Insert, Electric, Forced Air

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: Water Available

Structural Information

  • Structure Type: Wood Frame, Stick Built
  • Construction: Concrete, Brick, Vinyl Siding, Wood Frame
  • Roof: Composition
  • Entry Floor Number: 1
  • Square Feet: 2,500
  • Year Built: 2005

Additional Structures

  • Other Structures: Shed(s), See Remarks

Lot Features

  • Lot Size (Acres): 0.49
  • Lot Size (Sq. Ft.): 21,344
  • Lot Dimensions: 135 x 215 x 78 x 165
  • Frontage: City Street, State Road, Paved, Paved
  • Lot Features: Level
  • Zoning: RS
  • Fencing (Description): Back Yard, Wood, Fenced

Financial Considerations

  • For Sale: Yes
  • Price Per Sq. Ft.: $216
  • Association Fee: $68
  • Assoc Fee Freq.: Annually
  • Assessment Amount: $458,920
  • Tax Amount: $3,063.29
  • Tax Year: 2024
  • Terms: Cash, Conventional, FHA, USDA Loan, VA Loan

Disclosures and Reports

  • Special Conditions: Standard
  • Legal Description: WHISPERING WINDS LOT 50
  • Property ID: 97000476
  • Lot Number: 50

Listed by Coldwell Banker Advantage-Southern Pines, Leslie Riederer

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Listing agent

— 39 Winding Trail —

  • Leslie Riederer

    Coldwell Banker Advantage-Southern Pines

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 39 Winding Trail

School District:Moore County Schools
NameGradesDistance
McDeeds Creek Elementary
2953 Camp Easter Road, Southern Pines, NC 28387
K-52.5 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 39 Winding Trail Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/20/2026
Price Reduced
$540,000
-1.82%
MLS
5/07/2026
Listed
$550,000
15.79%
MLS
10/16/2023
Sold
$475,000
—
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 39 Winding Trail

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,224
2%
$458,920
—
2023
$3,155
5%
$458,920
53%
2022
$2,994
-2%
$300,860
—
2021
$3,069
6%
$300,860
—
2020
$2,885
4%
$300,860
7%
2019
$2,768
13%
$282,280
—
2016
$2,442
—
$282,280
—
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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Be ready to buy your new home!

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NMLS#: 1598647

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Listed by Coldwell Banker Advantage-Southern Pines, Leslie Riederer

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39 Winding Trail, Whispering Pines, NC 28327 (MLS# 100572040) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 39 Winding Trail is currently listed for $540,000 and was received on May 07, 2026. Want to learn more about 39 Winding Trail? Do you have questions about finding other Single Family 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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