Skip to content
Photo 1 of 50
Photo 1 of 50 — 39 Winding Trail, Whispering Pines, NC 28327
View all 50 photos

39 Winding Trail, Whispering Pines, NC 28327

WHISPERING WINDS (PINEHURST) · Moore County

Key Facts

4Beds
3Baths
2,500Sq Ft
2005Year Built
2Garage
2Stories

Description

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!

Property Information

Property Type

Residential

Sub-Type

Single Family Residence

Style

Two Story

Year Built

2005

Stories

2

Living Area

2,500 sq ft

Garage Spaces

2

Ownership

More than a year

Days on Market

66

MLS® Listing#

762307

Property Features

Interior

Ceiling Fan(s)Cathedral Ceiling(s)Double VanityEntrance FoyerHigh CeilingsPantryVaulted Ceiling(s)Walk-In Closet(s)

Appliances

Convection OvenDishwasherDisposalMicrowaveRangeRefrigerator

Cooling

Ceiling Fan(s)Central Air

Heating

Fireplace InsertElectricForced AirFireplace(s)Heat PumpPropane

Flooring

CarpetHardwoodTile

Fireplace

Gas LogLiving RoomInsert

Basement

Crawl Space

Parking

AttachedGarage

Laundry

Washer HookupMain Level

Patio

PorchPatioCoveredFront Porch

Fencing

Back Yard

Construction

BrickConcreteVinyl SidingFrame

Windows

Window CoveringsBlinds

Other Structures

Shed(s)

Sewer

Holding TankSeptic Tank

Water Source

Public

Schools

Middle:
New Century Middle
High:
Union Pines High

Financial Details

HOA

$68 / Annually

Whispering Winds Lake Owners Association

Parcel Number

97000476

Affordability Calculator

$106,000

Estimated monthly payment

$2,821/mo

Principal $424,000 · Est. interest $591,518 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in Whispering Pines, NC

$510,448
Median Listing Price
61
Median Days on Market
2,266
Median Sq Ft
$232
Median Price / Sq Ft
196
Active Listings
  • This home’s price is 4% above the area median.
  • Its price per sq ft is 9% below the area median.

Market statistics compiled from active EXIT Realty® and MLS listings in Whispering Pines, NC.

Location

Map showing the location of 39 Winding Trail, Whispering Pines, NC 28327

Points of Interest in Whispering Pines, NC

Showing the Whispering Pines area map.

Nearby Schools

  • Sandhills Classical Christian School

    School · 2.1 mi away

  • Sandhills Farm Life Elementary

    Elementary · 2.4 mi away

  • St John Paul II Catholic School

    School · 2.4 mi away

  • McDeeds Creek Elementary

    Elementary · 2.5 mi away

  • Stars Charter School

    Secondary · 3.1 mi away

  • Sandhills Theatre Arts Renaiss

    School · 3.1 mi away

  • Covenant Preparatory School

    School · 3.2 mi away

  • Little Schoolhouse

    School · 3.5 mi away

  • Father Vincent Capodanno High

    School · 3.5 mi away

  • Vass-Lakeview Elementary

    Elementary · 4.1 mi away

  • Little People Loving & Learn

    School · 4.6 mi away

  • Union Pines High School

    Secondary · 4.8 mi away

  • Union Pines Marching Vikings

    School · 4.8 mi away

  • Crain's Creek Middle

    Secondary · 4.9 mi away

  • Moore County Schools

    School · 5.0 mi away

  • Fellowship Pre-School

    School · 5.2 mi away

  • New Century Middle School

    Secondary · 5.4 mi away

  • Calvary Christian School

    School · 5.4 mi away

  • Episcopal Day School

    School · 5.6 mi away

  • Pinecrest Women S

    School · 5.8 mi away

Commute Calculator

Travel mode

Nearby Homes

Similar Homes Nearby

Similar Home Values

Comparable nearby listings and their asking prices.

Moving Cost Estimate

EXIT Agents in Whispering Pines

Fayetteville Association of Realtors logo

Listing Courtesy: COLDWELL BANKER ADVANTAGE #3-SOUTHERN PINES - 9106933300

The information being provided by Longleaf Pine REALTORS is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. ©2026 Longleaf Pine REALTORS All rights reserved.
The listing broker’s offer of compensation is made only to participants of the multiple listing service where the listing is filed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of one or more Multiple Listing Services (MLS). Listing information is deemed reliable but is not guaranteed accurate. Copyright © EXIT Realty® and respective MLS providers.

Data provided by Longleaf Pine Realtors. MLS® Listing#762307. © 2026EXIT Realty®. All rights reserved.