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$495,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 2,525 Sq. Ft.
  • 0.89 Acres
  • 2 Car Garage
  • Updated 2 hours ago
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Some houses are just houses. This one has a corded phone stretched across the kitchen cabinets, a Carolina room made for Sunday coffee, and a driveway that has seen a thousand bikes thrown down midsprint. Welcome to 44 Winding Trail a solid, all brick, four-bedroom home tucked into one of Whispering Pines' most coveted streets, sitting on a lot just over an acre where the kids actually have room to run. Inside, 2,525 square feet gives everyone their own corner, and a bonus room off the garage currently a home gym, flexes into whatever your family needs next: office, playroom, in-law space. Built in the early 2000s and constructed the way homes used to be built, this one isn't cutting corners to hit a price point. And then there's Whispering Pines itself Eight lakes, golf, walking trails, and the kind of neighborhood where everybody waves. This isn't just a place to live. It's a place your family's story gets told for years to come.

Full Property Details for 44 Winding Trail

General

  • Price: $495,000
  • HOA FEE: $6/month
  • HOA FEE FREQ.: Annually
  • Taxes: $3,103 (2024)
  • Status: Active
  • Type: Single Family
  • Source: 2253
  • MLS ID: 100597752
  • Updated: Today (8/20/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 9
  • Interior Features: Walk-in Closet(s), High Ceilings, Ceiling Fan(s), Reverse Floor Plan, Blinds/Shades, Eat-in Kitchen, Gas Log, Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Gas Log
  • Appliances: Built-In Microwave, Refrigerator, Dishwasher, Electric Range

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

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

Other Rooms

  • Eat-in kitchen: Yes

Additional Information

  • Shared Amenities: See Remarks

Exterior

  • Porch/Patio/Deck: Covered

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking Features: Garage

Location

  • County: Moore
  • Subdivision: Whispering Winds
  • Driving Directions: Airport road (beware of speed traps its 35 MPH) Turn L into Whispering Winds. Turn Right onto Winding Trail. Go down and the house is on the right.

School Information

  • High School District: Moore County Schools
  • Elementary School: Sandhills Farm Life
  • Middle School: New Century Middle
  • High School: Union Pines

Community

  • Association: Yes
  • Assoc. Name: Whispering Winds Lake Owners

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Central Air
  • Heating Type: Electric, Heat Pump

Utilities

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

Structural Information

  • Structure Type: Wood Frame, Stick Built
  • Construction: Brick, Wood Frame
  • Basement Desc.: None
  • Roof: Architectural Shingle
  • Entry Floor Number: 1
  • Square Feet: 2,525
  • Year Built: 2006

Lot Features

  • Lot Size (Acres): 0.89
  • Lot Size (Sq. Ft.): 38,768
  • Lot Dimensions: 78 x 244 x 154 x 315
  • Frontage: Paved, Paved
  • Zoning: R01
  • Fencing (Description): Back Yard

Financial Considerations

  • For Sale: Yes
  • Price Per Sq. Ft.: $196.04
  • Association Fee: $68
  • Assoc Fee Freq.: Annually
  • Assessment Amount: $464,940
  • Tax Amount: $3,103.47
  • Tax Year: 2024
  • Terms: Cash, Conventional, FHA, VA Loan

Disclosures and Reports

  • Special Conditions: Standard
  • Legal Description: WHISPERING WINDS LOT 44R
  • Property ID: 97000487

Listed by Love Pines Realty, Jennifer L Carlson and Love Pines Realty, Love Pines

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Listing agents

— 44 Winding Trail —

  • Jennifer L Carlson

    Love Pines Realty

  • Love Pines

    Love Pines 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 44 Winding Trail

School District:Moore County Schools
NameGradesDistance
McDeeds Creek Elementary
2953 Camp Easter Road, Southern Pines, NC 28387
K-52.6 mi
New Century Middle School
1577 Union Church Road, Cameron, NC 28326
6-85.3 mi
Union Pines High School
1981 Union Church Road, Cameron, NC 28326
9-124.9 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 44 Winding Trail Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/20/2026
Listed
$495,000
52.31%
MLS
8/30/2016
Sold
$325,000
—
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 44 Winding Trail

Year
Property Taxes
Change
Tax Assessment
Change
2026
$3,406
4%
$464,940
—
2025
$3,266
2%
$464,940
—
2023
$3,196
4%
$464,940
51%
2022
$3,063
-2%
$307,850
—
2021
$3,140
6%
$307,850
—
2020
$2,952
4%
$307,850
5%
2019
$2,832
12%
$293,380
—
2016
$2,538
—
$293,380
—
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 44 Winding Trail

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*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 Love Pines Realty, Jennifer L Carlson and Love Pines Realty, Love Pines

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44 Winding Trail, Whispering Pines, NC 28327 (MLS# 100597752) is a Single Family property with 4 bedrooms and 2 full bathrooms. 44 Winding Trail is currently listed for $495,000 and was received on August 20, 2026. Want to learn more about 44 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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