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Map location of 4 Winding Trail Lane, Hilton Head Island, SC 29926

$819,000

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4 Winding Trail Lane, Hilton Head Island, SC 29926

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3 Beds

3 Baths

2,088 Sq Ft

Welcome to 4 Winding Trail Lane in the highly desirable Headlands section of Hilton Head Plantation. This 3 bedroom, 2.5 bath home has a truly beautiful private lagoon and golf view. The 2088 square foot home has gorgeous new wainscotting and detailed trim with vaulted ceilings. New pipes & paint and Roof 2020. Gorgeous tile and glass enclosures in all bathrooms. Solid wood flooring throughout and new LED light fixtures and ceiling fans. Hilton Head Plantation is a gated community with low yearly fees and numerous amenities for their owners. This home has been meticulously cared for and well loved. This home needs to be seen in person!

Listing By: The Dacia Allen Team - Keller Williams Realty schhi Realty.com

MLS# 440522
Date Listed12/07/2023
Bedrooms 3
Bathrooms 2 Full baths, 1 Half baths
Lot Size -
Subdivision HEADLANDS
Property Type Single Family
County Beaufort
Year Built 1994
Water Public
Square Feet 2,088 sq. ft
Price Per Sq. Ft $392.24

Interior Features

Appliances Dryer, Dishwasher, Oven, Refrigerator, Washer
Flooring Carpet, Tile, Wood
Cooling Ceiling Fan(s), Central Air, Heat Pump
Heating Heat Pump, Central

Exterior / Lot Features

Exterior Rain Gutters
Roof Asphalt
Lot Size Acres -
Lot Size SQFT -
Lot Features -

Financial Considerations

Nearby Schools

Source: School Digger

Hilton Head Island International Baccalaureate Elementary School

Public • 1 - 5 • Serves this home

1.12 mi

Distance

Hilton Head Island Middle School

Public • 6 - 8 • Serves this home

1.12 mi

Distance

Hilton Head Island High School

Public • 9 - 12 • Serves this home

1.12 mi

Distance

Hilton Head Island International Baccalaureate Elementary School

Public • 1 - 5 • Serves this home

1.12 mi

Distance

Hilton Head Island School For The Creative Arts

Public • 1 - 5

1.12 mi

Distance

Hilton Head Early Childhood

Public • PK - KG

2.38 mi

Distance

Hilton Head Island Middle School

Public • 6 - 8 • Serves this home

1.12 mi

Distance

Hilton Head Island High School

Public • 9 - 12 • Serves this home

1.12 mi

Distance

Heritage Academy

Private • 06 - 12

7.24 mi

Distance

Sales & Tax History

Source: Public Records

Year	Total Assessments
2022	$16,368
2021	$16,368
2020	$16,368
2019	$14,660
2018	$14,660
2017	$12,740
2016	$12,740
2015	$19,120
2014	$318,600
2013	$19,120

Date	Event	Price
04/26/2024	Sold	$780,000.00 4.76%
03/11/2024	Pending	$819,000.00
03/06/2024	Active	$819,000.00 2.38%
02/01/2024	Active	$839,000.00 3.01%
01/10/2024	Active	$865,000.00 3.89%
12/14/2023	Active	$900,000.00

Street Address	Beds	Baths	Sold Date	List Price	Valuation Date	Valuation Price
9 Whispering Oaks Circle \| Listing	4	4	Nov 26, 2025	$416,101	Nov 28, 2025	-
6 Whispering Oaks Circle \| Listing	3	2	Nov 26, 2025	$370,656	Nov 28, 2025	-
13 Windy Cove Court \| Listing	3	3	Nov 26, 2025	$769,000	Jan 24, 2024	$775,710
8 Whispering Oaks Circle \| Listing	3	3	Nov 26, 2025	$392,990	Nov 28, 2025	-
7 Clove Hitch Court \| Listing	4	4	Nov 26, 2025	$1,350,000	Dec 28, 2020	$476,000
10 Whispering Oaks Circle	3	3	Nov 26, 2025	$399,990	Nov 28, 2025	-
87 Headlands Drive \| Listing	3	3	Nov 26, 2025	$925,000	Mar 21, 2024	$875,000
4 Leatherwood Court \| Listing	3	3	Nov 26, 2025	$865,000	Mar 21, 2024	$825,161
7 Whispering Oaks Circle	4	3	Nov 26, 2025	$414,990	Nov 28, 2025	-
10 Mangrove Street \| Listing	4	3	Nov 26, 2025	$749,900	Mar 21, 2024	$648,301

Population & Environment

Source: Sperling's Best Places

	Zip	City	County	National
Population	26,040	41,428	195,581	335,858,263
Population Density	920	1,002	339	95
People per Household	2.4	2.2	2.4	2.6
Median Age	49	51.3	42.6	39.1
Median Income	$85,093	$89,958	$71,086	$66,222
Average Income	$49,757	$58,090	$40,099	$35,475
Cost of Living Index	101	96	98	100

	Zip	City	County	National
January Avg. High Temp	37.3°F	37.3°F	37.3°F	22.6°F
July Avg. High Temp	88.2°F	88.2°F	88.2°F	86.2°F
Annual Precipitation	52.52"	52.52"	52.52"	38"

...

Walkability in SC / 29926

Source: Walkscore

31/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 9/100, Transit Score: 0/100, Bike Score: 39/100.

Property Change History

26 Nov 2025

Property Interior Features updated

View Changes

Previous Value:

Eat-in Kitchen, Pantry, Tray Ceiling(s), Ceiling Fan(s), Cathedral Ceiling(s), See Remarks, Entrance Foyer

Updated Value:

Vaulted Ceiling(s), Eat-in Kitchen, Pantry, Tray Ceiling(s), Ceiling Fan(s), Cathedral Ceiling(s), High Ceilings, Entrance Foyer

Points of Interest near 4 Winding Trail Lane, Hilton Head Island, SC 29926

Gullah Museum of Hilton Head Island, Hilton Head, SC, USA

Education • Entertainment

0.55 mi

Distance

Island Recreation Center, Hilton Head Island, SC, USA

Recreation • Education • Entertainment

0.75 mi

Distance

Hilton Head Middle School, Hilton Head, SC, USA

Education

0.76 mi

Distance

Hilton Head Island High School, Hilton Head, SC, USA

Education

0.81 mi

Distance

Hilton Head School for the Creative Arts, Hilton Head, SC, USA

Education

0.91 mi

Distance

Hilton Head International Baccalaureate Elementary School, Hilton Head, SC, USA

Education

0.91 mi

Distance

Skull Creek Boathouse, Hilton Head Island, SC, USA

Food • Retail • Nightlife

0.9 mi

Distance

Skull Creek Dockside, Hilton Head, SC, USA

Food • Retail • Nightlife

0.94 mi

Distance

Hudson’s Seafood House on the Docks, Hilton Head, SC, USA

Food • Retail • Nightlife

1 mi

Distance

Skull Creek Boathouse, Hilton Head Island, SC, USA

Food • Retail • Nightlife

0.9 mi

Distance

Skull Creek Dockside, Hilton Head, SC, USA

Food • Retail • Nightlife

0.94 mi

Distance

Circle K, Hilton Head Island, SC, USA

Retail

1 mi

Distance

Hudson’s Seafood House on the Docks, Hilton Head, SC, USA

Food • Retail • Nightlife

1 mi

Distance

Bear Creek Golf Club, Hilton Head, SC, USA

Recreation • Entertainment

0.38 mi

Distance

Gullah Museum of Hilton Head Island, Hilton Head, SC, USA

Education • Entertainment

0.55 mi

Distance

Island Recreation Center, Hilton Head Island, SC, USA

Recreation • Education • Entertainment

0.75 mi

Distance

Skull Creek Boathouse, Hilton Head Island, SC, USA

Food • Retail • Nightlife

0.9 mi

Distance

Skull Creek Dockside, Hilton Head, SC, USA

Food • Retail • Nightlife

0.94 mi

Distance

Hudson’s Seafood House on the Docks, Hilton Head, SC, USA

Food • Retail • Nightlife

1 mi

Distance

Bear Creek Golf Club, Hilton Head, SC, USA

Recreation • Entertainment

0.38 mi

Distance

Island Recreation Center, Hilton Head Island, SC, USA

Recreation • Education • Entertainment

0.75 mi

Distance

Boys & Girls Club, Hilton Head Island, SC, USA

Health

0.67 mi

Distance

Mount Calvary Church, Hilton Head Island, SC, USA

Religion

0.8 mi

Distance

Fairfield Station Post Office, Hilton Head Island, SC, USA

Government

1.01 mi

Distance

BP, Hilton Head Island, SC, USA

Transport • Professional

1.01 mi

Distance

BP, Hilton Head Island, SC, USA

Transport • Professional

1.01 mi

Distance

Jarvis Creek, Hilton Head Island, SC, USA

0.66 mi

Distance

Loblolly Pine, Hilton Head Island, SC, USA

0.73 mi

Distance

Private, Hilton Head Island, SC, USA

0.78 mi

Distance

Whooping Crane Pond, Hilton Head Island, SC, USA

0.8 mi

Distance

Fort Mitchel, Hilton Head, SC, USA

1.02 mi

Distance

Frequently Asked Questions for 4 Winding Trail Lane

Source: Realty.com

4 Winding Trail Lane, Hilton Head Island, SC 29926 is a Single Family 2,088 sq. ft. home listed for sale. Realty.com has 1 photos available of this 3 bed, 3 bath house, listed at $819,000. View sales and tax history, use our mortgage calculator and more on Realty.com

Our records indicate that 4 Winding Trail Lane was built in 1994.

The full address for this home is 4 Winding Trail Lane, Hilton Head Island, SC 29926.

4 Winding Trail Lane has been listed on Realty.com since Thu December 07, 2023

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 9/100, Transit Score: 0/100, Bike Score: 39/100.

There are 3 schools assigned to this home. Check out the schools near 4 Winding Trail Lane. Hilton Head Island International Baccalaureate Elementary School (Grades: 1 - 5), Hilton Head Island Middle School (Grades: 6 - 8), Hilton Head Island High School (Grades: 9 - 12)

Listing provided courtesy of: Keller Williams Realty (tel: 858-720-1900)
Listing agent: The Dacia Allen Team (tel: 234-575-1020) (#715322)

This content last refreshed on 2025-11-28 03:55:30. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

Export listing data of 4 Winding Trail Lane, Hilton Head Island, SC 29926 : MLS# 440522

4 Winding Trail Lane, Hilton Head Island, SC 29926

Interior Features

Exterior / Lot Features

Financial Considerations

Nearby Schools

1.12 mi

1.12 mi

1.12 mi

1.12 mi

1.12 mi

2.38 mi

1.12 mi

1.12 mi

7.24 mi

Sales & Tax History

Population & Environment

Walkability in SC / 29926

Bikable

Overview

Walkability averages in the surrounding area

Previous Value:

Updated Value:

Nearby Properties

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Nearby Locations

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Frequently Asked Questions for 4 Winding Trail Lane

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How long has this home been listed on Realty.com?

What is the Walkability around 4 Winding Trail Lane, Hilton Head Island, SC 29926?

What is the Walkability averages in the surrounding areas of Hilton Head Island?

What schools are assigned to this home?