111 Live Oak Drive, Mount Pleasant, SC 29464
Local realty services provided by:Better Homes and Gardens Real Estate Palmetto
Listed by: nancy hoy843-779-8660
Office: carolina one real estate
MLS#:26029918
Source:SC_CTAR
111 Live Oak Drive,Mount Pleasant, SC 29464
$19,500,000
- 5 Beds
- 6 Baths
- 5,459 sq. ft.
- Single family
- Active
Price summary
- Price:$19,500,000
- Price per sq. ft.:$3,572.08
About this home
A rare piece of Charleston history, this extraordinary deepwater estate occupies a commanding high bluff overlooking Charleston Harbor, offering sweeping water views, exceptional boating access, and a remarkable connection to the Lowcountry's past. Set on nearly an acre in the heart of the Old Village of Mount Pleasant, the property is believed to be among the area's earliest surviving homes, offering an extraordinary blend of historic architectural integrity, timeless craftsmanship, and beautifully renovated living spaces.Rich in local history, the property is situated on Haddrell's Point, a historic settlement that supported a ferry operation from the mid-1700s through the mid-1800s. Local historical accounts also associate these shores with George Washington's visit to Charlestonin the 18th century. The residence retains an exceptional collection of period details, including hand-hewn structural timbers, distinctive dragon-beam bracing, remarkably wide 9- to 13-inch mill-sawn floors, and expansive cypress paneling--a rare testament to the craftsmanship of an earlier era.
Throughout the fully renovated main residence, historic character is complemented by modern comfort, with soaring ceilings, beautiful moldings, and seven working fireplaces creating an atmosphere that is both gracious and inviting. Full-length double porches frame breathtaking harbor views, while a covered ground-level loggia provides a natural transition to the infinity pool and outdoor entertaining spaces.
The main living level is designed for both comfortable everyday living and exceptional entertaining, with a beautifully appointed kitchen, dining area, inviting living room, and elegant bar. The second floor features a spacious primary suite with a generous closet and well-appointed bath, along with a second bedroom offering its own ensuite bath and oversized closet. Two additional guest bedrooms on the top floor share a full hall bath. The parterre of the home is in an X flood zone not requiring flood insurance and offers remarkable flexibility, with an expansive living area anchored by a beautiful masonry fireplace, a second kitchen, and a dedicated office or flex space, all opening directly to the covered loggia, pool house, and pool area which cascades to the dock. This area can easily function as a separate au pair or mother-in-law arrangement.
Beyond the main residence, the property includes a fully renovated guest house situated above the three-car garage. Thoughtfully arranged with an open-concept layout, the space features a kitchenette, living area, and sleeping quarters. An additional single-car garage provides even more storage and flexibility. The separate pool house offers further versatility for guests and outdoor entertainment.
The outdoor setting is every bit as impressive as the interiors. A stunning new pool and pool house (230sqft), beautifully executed with a park-like setting. This work was completed in 2025 to create a private waterfront oasis. The deepwater dock is equipped with railings on both sides and two new power lifts installed in 2023, offering exceptional access to Charleston Harbor and beyond.
Significant capital improvements include a new copper roof, gutters, and downspouts on the main residence and pool house in 2022; new HVAC systems and built-in dehumidifiers throughout all floors of the main residence in 2022; all new windows throughout the property (2025); and new lightning protection on the main house and guest house in 2023.
With extraordinary harbor views stretching along the Old Village waterfront toward Fort Sumter and the tip of Sullivan's Island as well as the Charleston coastline, 111 Live Oak Drive is an exceptionally rare offering. Combining a storied past, remarkable architectural details, extensive modern renovations, and premier deepwater amenities, this is a truly distinctive opportunity to experience the very best of historic Old Village and Lowcountry waterfront living, just minutes from downtown Charleston and the area's best beaches....
Contact an agent
Home facts
- Year built:1830
- Subdivision & Development:Old Village
- Listing ID #:26029918
- Added:4 day(s) ago
- Updated:November 09, 2026 at 04:39 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:6
- Full bathrooms:5
- Half bathrooms:1
- Flooring:Ceramic Tile, Stone, Wood
- Kitchen Description:Eat-in Kitchen, Kitchen Island
- Living area:5,459 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Heat Pump
- Central air:Yes
Structure and exterior
- Year built:1830
- Building area:5,459 sq. ft.
- Lot area:0.8 Acres
- Lot Features:.5 - 1 Acre, Marshview
- Architectural Style:Traditional
- Foundation Description:Pillar/Post/Pier, Raised
- Levels:4 Story
Schools
- High school:Lucy Beckham
- Middle school:Moultrie
- Elementary school:Mt. Pleasant Academy
Utilities
- Water:Public
Finances and disclosures
- Price:$19,500,000
- Price per sq. ft.:$3,572.08
Features and amenities
- Amenities:Ceiling Smooth, High Ceilings
Parking
- Total parking spaces:4
- Parking description:1 Car Garage, 3 Car Garage, Detached, Off Street
- Garage:Yes
- Garage spaces:4
New listings near 111 Live Oak Drive
- Coming Soon
$3,795,000Coming Soon6 beds 7 baths4,184 sq. ft.1490 Seminole Street, Mount Pleasant, SC 29464
MLS# 26030095Listed by: OAKMONT GROUP INC - Coming Soon
$700,000Coming Soon3 beds 3 baths1,952 sq. ft.3095 Sturbridge Road, Mount Pleasant, SC 29466
MLS# 26029960Listed by: CAROLINA ONE REAL ESTATE - New
$975,000Active3 beds 4 baths2,503 sq. ft.1949 Carolina Towne Court, Mount Pleasant, SC 29464
MLS# 26030265Listed by: CAROLINA ONE REAL ESTATE - New
$2,095,000Active3 beds 3 baths2,655 sq. ft.1457 Appling Drive, Mount Pleasant, SC 29464
MLS# 26030255Listed by: ENGEL & VOLKERS CHARLESTON - New
$3,995,000Active3 beds 3 baths2,312 sq. ft.833 Pitt Street, Mount Pleasant, SC 29464
MLS# 26030256Listed by: MAISON REAL ESTATE - New
$383,800Active1 beds 1 baths786 sq. ft.1600 Long Grove #Unit 1128, Mount Pleasant, SC 29464
MLS# 26030248Listed by: THE BOULEVARD COMPANY - New
$4,795,000Active6 beds 6 baths4,004 sq. ft.304 Bank Street, Mount Pleasant, SC 29464
MLS# 26030245Listed by: COMPASS CAROLINAS, LLC - New
$700,000Active3 beds 2 baths1,285 sq. ft.721 Harbor Lane, Mount Pleasant, SC 29464
MLS# 26030208Listed by: BEYCOME BROKERAGE REALTY LLC - New
$995,000Active3 beds 3 baths2,829 sq. ft.2216 Branch Creek Drive, Mount Pleasant, SC 29466
MLS# 26030195Listed by: EXP REALTY LLC - New
$699,000Active3 beds 3 baths1,928 sq. ft.3443 Yarmouth Drive, Mount Pleasant, SC 29466
MLS# 26030189Listed by: DANIEL RAVENEL SOTHEBY'S INTERNATIONAL REALTY
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.