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$1,250,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 2,600 Sq. Ft.
  • 2 Car Garage
  • Updated 5 days ago
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Welcome to Parаdіse! Τhіs ѕingle level 3br/3ba sanctuаry іs nestled high on a bluff along the River/Marsh on beautiful Callawassie Island. This home has been freshly re-imagined and offers you breathtaking Cove views with beautiful sunsets. The gourmet kitchen is a chef's kiss and opens to entertaining areas, Great Room and Carolina Room. Multiple rooms offer spectacular views to the Water and it is an exceptionally light and bright floorplan. It is perfectly positioned on a generous size, beautifully landscaped lot offering indoor/outdoor living and access to a rear pavered patio. Callawassie Island Club has some of the best amenities, including pickleball/tennis, optional golf, dining, multiple pool and spa services on site. This location is central to all things Lowcountry including the towns of Bluffton, Beaufort, Savannah and Hilton Head Island. Come LiveLowcountryLife...

Full Property Details for 66 Winding Oak Dr

General

  • Price: $1,250,000
  • Status: Active
  • Type: Single Family
  • Source: 2263
  • MLS ID: 513595
  • Updated: 10/18/2026
  • Added to Site: 7 day(s) ago

Interior

  • Interior Features: Attic, Bookcases, Built-in Features, Ceiling Fan(s), Carbon Monoxide Detector, Fireplace, Handicap Access, Main Level Primary, Multiple Closets, Pull Down Attic Stairs, Smooth Ceilings, Smart Thermostat, Window Treatments, Entrance Foyer, Eat-in Kitchen, New Paint, Pantry
  • Appliances: Convection Oven, Double Oven, Dryer, Dishwasher, Freezer, Disposal, Gas Range, Microwave, Refrigerator, Self Cleaning Oven, Washer
  • Furnishings: Unfurnished
  • Flooring: Luxury Vinyl, Luxury VinylPlank, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Shared Amenities: Bocce Court, Business Center, Clubhouse, Dog Park, Fitness Center, Gas, Golf Course, Barbecue, Playground, Pickleball, Pool, Restaurant, Guard, Spa/Hot Tub, Tennis Court(s), Trail(s)
  • Shared Pool: Yes
  • Pool: Yes
  • Pool Description: Lap, Community
  • Security/Safety: Smoke Detector(s)

Exterior

  • Exterior Features: Handicap Accessible, Irrigation Sprinklers, Propane Tank - Owned, Paved Driveway, Propane Tank - Leased, Patio, Rain Gutters
  • Porch/Patio/Deck: Patio

Parking

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

Location

  • County: Beaufort
  • Subdivision: CALLAWASSIE ISLAND

Community

  • Community Name: Callawassie Island
  • Pets Allowed: Yes

Heating & Cooling

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

Utilities

  • Water: Public

Structural Information

  • Architectural Style: One Story
  • Detached/Attached: Detached
  • Model: Custom
  • Construction: Synthetic Stucco
  • Roof: Asphalt
  • Windows: Other, Screens, Window Treatments
  • Stories/Levels: 1
  • Square Feet: 2,600
  • Living Area: 2,600 Sq. Ft.
  • Year Built: 1995

Lot Features

  • Property View: Marsh View, River
  • Lot Size: .53
  • Lot Features: 1/2 to 1 Acre Lot, Waterfront

Water Features

  • Water View: Yes

Financial Considerations

  • Terms: Cash, Conventional, VA Loan

Disclosures and Reports

  • Special Conditions: None
  • Lot Number: 89

Listed by RE/MAX Island Realty, Nonna Klinect (843) 593-0096

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Listing agent

— 66 Winding Oak Dr —

  • Nonna Klinect

    RE/MAX Island 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 66 Winding Oak Dr

School District:Beaufort County School District
NameGradesDistance
Okatie Elementary School
53 Cherry Point Road, Bluffton, SC 29909
PK-53.6 mi
Bluffton Middle School
30 New Mustang Drive, Bluffton, SC 29910
6-85 mi
May River High
601 New Riverside Road, Bluffton, SC 29910
9-129.6 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 66 Winding Oak Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/16/2026
Listed
$1,250,000
11.11%
MLS
7/25/2023
Sold
$1,125,000
—
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 66 Winding Oak Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$16,826
2%
$67,500
—
2024
$16,543
449%
$67,500
182%
2023
$3,013
-62%
$23,920
15%
2022
$8,019
24%
$20,800
-19%
2021
$6,442
5%
$25,530
—
2019
$6,143
6%
$25,530
—
2018
$5,822
2%
$25,530
6%
2017
$5,706
2%
$23,980
—
2016
$5,608
5%
$23,980
—
2015
$5,353
2%
$23,980
-94%
2014
$5,232
3%
$399,600
1566%
2013
$5,073
—
$23,980
—
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 66 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 RE/MAX Island Realty, Nonna Klinect (843) 593-0096

66 Winding Oak Drive, Okatie, SC 29909 (MLS# 513595) is a Single Family property with 3 bedrooms and 3 full bathrooms. 66 Winding Oak Drive is currently listed for $1,250,000 and was received on October 16, 2026. Want to learn more about 66 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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