A rare chance to live in one of South Carolina's most prestigious island communities at a fraction of current market values. Set on approximately half an acre overlooking the Magnolia course's 3rd green, this 2,867 square-foot ranch offers a generous primary suite, dedicated office, formal dining, fireplace, wet bar + private bonus suite above the garage. Cathedral and tray ceilings w/ oversized windows bring natural light throughout the living spaces, while the rear deck connects the home directly to its golf setting. For buyers who value room, privacy and the ability to personalize rather than pay a premium for another's renovation, 49 Winding Oak presents a compelling entry point into Callawassie's Lowcountry lifestyle. Seller to offer buyer $37,500 in closing costs w/acceptable offer.
For sale
Price cut: $10K (9/3)
$689,900
49 Winding Oak Drive, Okatie, SC 29909
3beds
2,867sqft
Single Family Residence
Built in 1995
0.51 Acres Lot
$-- Zestimate®
$241/sqft
$-- HOA
What's special
Cathedral and tray ceilingsFormal diningDedicated officeWet barGenerous primary suite
- 237 days
- 842
- 36
Zillow last checked:
Listing updated:
Listed by:
Alec Smith 917-648-1704,
Charter One Realty
Source: REsides, Inc.,MLS#: 503347
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Level: First
Heating
- Central, Electric, Heat Pump
Cooling
- Central Air, Electric, Heat Pump
Appliances
- Included: Dryer, Dishwasher, Disposal, Microwave, Oven, Range, Refrigerator, Washer
Features
- Attic, Wet Bar, Bookcases, Tray Ceiling(s), Ceiling Fan(s), Cathedral Ceiling(s), Fireplace, High Ceilings, Main Level Primary, New Paint, Smooth Ceilings, Smart Thermostat, Vaulted Ceiling(s), Window Treatments, Central Vacuum, Entrance Foyer, Pantry
- Flooring: Carpet, Tile, Wood
- Windows: Insulated Windows, Window Treatments
Interior area
- Total interior livable area: 2,867 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Garage, Two Car Garage
- Garage spaces: 2
Features
- Patio & porch: Rear Porch, Deck, Front Porch
- Exterior features: Deck, Paved Driveway, Porch
- Pool features: Community
- Has view: Yes
- View description: Golf Course
- Water view: Golf Course
Lot
- Size: 0.51 Acres
- Features: 1/2 to 1 Acre Lot
Details
- Parcel number: R60001500A00860000
- Special conditions: None
- Other equipment: Satellite Dish
Construction
Type & style
- Home type: SingleFamily
- Architectural style: One and One Half Story
- Property subtype: Single Family Residence
Materials
- Wood Siding
- Roof: Asphalt
Condition
- Year built: 1995
Details
- Builder model: Other
Utilities & green energy
- Water: Community/Coop, Public
Green energy
- Indoor air quality: Ventilation
Community & HOA
Community
- Subdivision: Callawassie Island
HOA
- Amenities included: Clubhouse, Dock, Dog Park, Fitness Center, Barbecue, Playground, Pickleball, Pool, Restaurant, Guard, Tennis Court(s)
Location
- Region: Okatie
Financial & listing details
- Price per square foot: $241/sqft
- Tax assessed value: $675,400
- Annual tax amount: $1,687
- Date on market: 1/9/2026
- Listing terms: Cash,Conventional,VA Loan
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 9/3/2026 | Price change | $689,900-1.4%$241/sqft |
Source:  Lowcountry Regional MLS #193784 Report a problem | ||
| 5/26/2026 | Price change | $699,900-6.7%$244/sqft |
Source: Lowcountry Regional MLS #193784 Report a problem | ||
| 5/12/2026 | Price change | $749,900-6.1%$262/sqft |
Source: Lowcountry Regional MLS #193784 Report a problem | ||
| 3/29/2026 | Price change | $799,000-3.7%$279/sqft |
Source: Lowcountry Regional MLS #193784 Report a problem | ||
| 1/28/2026 | Price change | $830,000-7.7%$290/sqft |
Source: Lowcountry Regional MLS #193784 Report a problem | ||
| 1/9/2026 | Listed for sale | $899,000+222.2%$314/sqft |
Source:  REsides, Inc. #503347 Report a problem | ||
| 12/1/2020 | Sold | $279,000-6.7%$97/sqft |
Source: Lowcountry Regional MLS #166016 Report a problem | ||
| 10/14/2020 | Pending sale | $299,000$104/sqft |
Source: Coastal R. E. Solutions II #166016 Report a problem | ||
| 8/3/2020 | Price change | $299,000-6.3%$104/sqft |
Source: Coastal R. E. Solutions II #166016 Report a problem | ||
| 6/17/2020 | Price change | $319,000-5.9%$111/sqft |
Source: Coastal R. E. Solutions II #166016 Report a problem | ||
| 4/18/2020 | Listed for sale | $339,000$118/sqft |
Source: Coastal R. E. Solutions II #166016 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $1,687 -69.9% | $15,040 -33.3% |
| 2024 | $5,596 +0% | $22,560 |
| 2023 | $5,596 +10.2% | $22,560 +15% |
| 2022 | $5,080 +2.1% | $19,620 |
| 2021 | $4,974 | $19,620 +27.9% |
| 2020 | -- | $15,340 |
| 2019 | $1,737 +2.9% | $15,340 |
| 2018 | $1,688 +14.3% | $15,340 +13.8% |
| 2017 | $1,478 | $13,480 |
| 2016 | $1,478 | $13,480 |
| 2015 | $1,478 | $13,480 |
| 2014 | $1,478 | $13,480 |
| 2013 | $1,478 | $13,480 |
| 2010 | $1,478 +3.7% | -- |
| 2009 | $1,425 -22.1% | -- |
| 2008 | $1,828 +6.5% | $17,332 |
| 2007 | $1,716 -34.7% | $17,332 |
| 2005 | $2,626 +3.5% | $17,332 |
| 2004 | $2,537 +39.9% | $17,332 +84.1% |
| 2003 | $1,813 | $9,412 |
| 2001 | -- | -- |
| 2000 | -- | $285,300 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 29909
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