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$679,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,871 Sq. Ft.
  • 2 Car Garage
  • Updated 2 days ago
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Under $700K and overlookіng thе Magnοlіa сourse's 3rd green, 49 Winding Οak οffers a move-in ready entry into one of South Carolina's most prestigious island communities. Set on approximately half an acre, this 2,867 square-foot single-level residence is filled with natural light and Lowcountry ease. Cathedral and tray ceilings rise above living spaces framed by oversized windows, creating an airy backdrop for both quiet evenings and gracious entertaining. A fireplace and wet bar warm the gathering areas, while formal dining invites long dinners with family and friends. The primary suite is a generous private retreat, and a dedicated office supports work from home with ease. Above the garage, a private bonus suite offers a welcoming space for guests or a flexible retreat of your own. Step out to the rear deck and the golf course becomes an extension of everyday living. Ready to enjoy from the day you arrive, with room to make it your own over time, this is an inspired beginning to your Callawassie Island story.

Full Property Details for 49 Winding Oak Dr

General

  • Price: $679,000
  • Status: Active
  • Type: Single Family
  • Source: 2263
  • MLS ID: 513676
  • Updated: 10/21/2026
  • Added to Site: 2 day(s) ago

Interior

  • Interior Features: Attic, Wet Bar, Bookcases, Tray Ceiling(s), Ceiling Fan(s), Cathedral Ceiling(s), Fireplace, High Ceilings, Main Level Primary, Multiple Closets, New Paint, Smooth Ceilings, Separate Shower, Smart Thermostat, Vaulted Ceiling(s), Window Treatments, Entrance Foyer, Pantry
  • Appliances: Dryer, Dishwasher, Disposal, Microwave, Oven, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Carpet, Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Shared Amenities: Bocce Court, Clubhouse, Dock, Dog Park, Fitness Center, Fire Pit, Golf Course, Garden Area, Barbecue, Playground, Pickleball, Pool, Restaurant, Guard, Tennis Court(s)
  • Shared Pool: Yes
  • Pool: Yes
  • Pool Description: Community
  • Equipment: Satellite Dish

Exterior

  • Exterior Features: Deck, Paved Driveway, Porch
  • Porch/Patio/Deck: Rear Porch, 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
  • Pets Allowed: Yes

Heating & Cooling

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

Utilities

  • Water: Community/Coop, Public

Structural Information

  • Architectural Style: One and One Half Story
  • Detached/Attached: Detached
  • Construction: Wood Siding
  • Roof: Asphalt
  • Windows: Insulated Windows, Window Treatments
  • Square Feet: 2,871
  • Living Area: 2,871 Sq. Ft.
  • Year Built: 1995

Lot Features

  • Property View: Golf Course
  • Lot Size: .51
  • Lot Features: 1/2 to 1 Acre Lot

Green Features

  • Indoor Air Quality: Ventilation

Financial Considerations

  • Terms: Cash, Conventional, VA Loan

Disclosures and Reports

  • Special Conditions: None
  • Lot Number: 25

Listed by Coastal Real Estate Solutions II, Joseph Kearney (541) 977-7373 and Coastal Real Estate Solutions II, Emily Kearney (541) 420-5271

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Listing agents

— 49 Winding Oak Dr —

  • Joseph Kearney

    Coastal Real Estate Solutions II

  • Emily Kearney

    Coastal Real Estate Solutions II

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 49 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
6-85.2 mi
May River High
601 New Riverside Road, Bluffton, SC 29910
9-129.8 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 49 Winding Oak Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/21/2026
Listed
$679,000
143.37%
MLS
11/25/2020
Sold
$279,000
—
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 49 Winding Oak Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,727
-43%
$15,040
-44%
2024
$6,581
18%
$27,016
—
2023
$5,596
13%
$27,016
107%
2021
$4,974
-2%
$13,080
—
2022
$5,080
2%
$13,080
-15%
2021
$4,974
186%
$15,340
—
2019
$1,737
3%
$15,340
—
2018
$1,688
15%
$15,340
14%
2017
$1,474
2%
$13,480
—
2016
$1,450
2%
$13,480
—
2015
$1,420
6%
$13,480
-96%
2014
$1,343
1%
$336,900
2399%
2013
$1,336
—
$13,480
—
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.

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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 Coastal Real Estate Solutions II, Joseph Kearney (541) 977-7373 and Coastal Real Estate Solutions II, Emily Kearney (541) 420-5271

49 Winding Oak Drive, Okatie, SC 29909 (MLS# 513676) is a Single Family property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 49 Winding Oak Drive is currently listed for $679,000 and was received on October 21, 2026. Want to learn more about 49 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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