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$1,299,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,500 Sq. Ft.
  • 2 Car Garage
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108 Winding Oak Drive, Okatie, SCVideo Tour of 108 Winding Oak Drive, Okatie, SC.
Completed in 2024, this custom Allison Ramsey-designed home sits on a 1.14-acre marshfront lot, created by consolidating part of a neighboring parcel to enhance privacy, space, and views. Designed to embrace its surroundings, the elevated home offers sweeping marsh views and a blend of Lowcountry charm and casual luxury. Built by CMS with top-tier finishes, it features approx. 2,500 sq ft, French oak floors, Andersen windows and doors, 10-foot ceilings, and a new elevator. A rare opportunity for buyers seeking a brand-new home without the time and hassle of building. The kitchen features Thermador and Bosch appliances, custom cabinetry, and a large island. Outdoor living includes a wraparound porch, tabby fireplace, gas lanterns, irrigation, and a tankless water heater.

Full Property Details for 108 Winding Oak Dr

General

  • Price: $1,299,000
  • Status: Active
  • Type: Single Family
  • Source: 2263
  • MLS ID: 500380
  • Updated: 3/6/2026
  • Added to Site: 242 day(s) ago

Interior

  • Interior Features: Attic, Elevator, Fireplace, Main Level Primary, Multiple Primary Suites, Multiple Closets, Entrance Foyer
  • Appliances: Dryer, Dishwasher, Gas Range, Refrigerator, Washer, Tankless Water Heater
  • Furnishings: Unfurnished
  • Flooring: Engineered Hardwood, Tile

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Shared Amenities: Clubhouse, Dog Park, Fitness Center, Fire Pit, Golf Course, Pickleball, Pool, Restaurant, Guard, Tennis Court(s)
  • Shared Pool: Yes
  • Pool: Yes
  • Pool Description: Community

Exterior

  • Exterior Features: Deck
  • Porch/Patio/Deck: Deck, Front Porch

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking Features: Garage, Two Car Garage

Location

  • County: Beaufort
  • Subdivision: CALLAWASSIE ISLAND

Community

  • Community Name: Callawassie Island

Heating & Cooling

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

Utilities

  • Water: Public, Private

Structural Information

  • Architectural Style: Two Story
  • Detached/Attached: Detached
  • Model: Custom
  • Construction: Composite Siding
  • Roof: Metal
  • Windows: Other
  • Stories/Levels: 2
  • Square Feet: 2,500
  • Living Area: 2,500 Sq. Ft.
  • Year Built: 2024

Lot Features

  • Property View: Marsh View
  • Lot Size: 1.14
  • Lot Features: 1-3 Acres

Financial Considerations

  • Terms: Cash, Conventional, VA Loan

Disclosures and Reports

  • Special Conditions: None
  • Lot Number: 40

Listed by Coastal Real Estate Solutions II (566), Emily Kearney (541) 420-5271

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Listing agent

— 108 Winding Oak Dr —

  • Emily Kearney

    Coastal Real Estate Solutions II (566)

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 108 Winding Oak Dr

School District:Beaufort County School District
NameGradesDistance
Okatie Elementary School
53 Cherry Point Road, Bluffton, SC 29909
PK-53.8 mi
Bluffton Middle School
30 New Mustang Drive, Bluffton, SC 29910
6-84.6 mi
May River High
601 New Riverside Road, Bluffton, SC 29910
9-129.5 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 108 Winding Oak Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/15/2026
Price Reduced
$1,299,000
-7.21%
MLS
10/14/2025
Price Reduced
$1,399,900
-4.7%
MLS
8/05/2025
Listed
$1,469,000
2348.33%
MLS
5/23/2022
Sold
$60,000
—
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 108 Winding Oak Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$15,232
1707%
$60,780
1657%
2024
$843
—
$3,460
—
2023
$843
106%
$3,460
131%
2022
$410
2%
$1,500
—
2021
$402
5%
$1,500
—
2019
$384
-56%
$1,500
-61%
2018
$876
10%
$3,800
15%
2017
$795
-43%
$3,300
-45%
2016
$1,403
-6%
$6,000
-10%
2015
$1,487
2%
$6,670
-94%
2014
$1,457
3%
$111,090
1566%
2013
$1,413
—
$6,670
—
View All
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 108 Winding Oak Dr

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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

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Listed by Coastal Real Estate Solutions II (566), Emily Kearney (541) 420-5271

108 Winding Oak Drive, Okatie, SC 29909 (MLS# 500380) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 108 Winding Oak Drive is currently listed for $1,299,000 and was received on August 05, 2025. Want to learn more about 108 Winding Oak Drive? Do you have questions about finding other Single Family real estate for sale in Okatie? You can browse all Okatie real estate or contact a Coldwell Banker agent to request more information.

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