111 Live Oak Drive : The Brennaman Group

The Brennaman Group > Mount Pleasant > Old Village > 111 Live Oak Drive

111 Live Oak Drive, Mount Pleasant, SC 29464 $19,500,000

At about 6,150 square feet, 111 Live Oak Drive is the largest home for sale in the Old Village neighborhood of Mount Pleasant (by total heated square feet).

Bedrooms 5

Full Bathrooms 5

SqFt 6,150

Updated 11/04/2026

Half Bathrooms 2

Price/SqFt $3,171

General Features

Category Residential

Water Marshfront, Waterfront - Deep

Style Traditional

Stories 4

Lot Description Marshview,.5 - 1 Acre

County Charleston

City Mount Pleasant

Subdivision Old Village

MLS number 26029918 (Active)

Address 111 Live Oak Drive, Mount Pleasant, SC 29464 US

Listing Provided by Carolina One Real Estate

Sale Type Not an Auction

MLS Area 42 - Mt Pleasant S of IOP Connector

Waterfront Property

Marshfront, Waterfront - Deep

Description : 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.

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, 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.

Exterior Features

Exterior Wood Siding

Foundation Raised,Pillar/Post/Pier

Roof Copper

Misc. Exterior Boatlift,Dock - Existing,In Ground

Interior Features

Fireplace Bedroom,Family Room,Kitchen,Living Room,Three +

Flooring Ceramic Tile,Wood,Stone

Master Bedroom Walk-In Closet(s)

Cooling Central Air

Heating Heat Pump

Amenities

• Tennis Court(s)

• Trash

Schools

Elementary School
Mt. Pleasant Academy

Middle School
Moultrie

High School
Lucy Beckham

111 Live Oak Drive is listed for sale at $19,500,000 and is in the 29464 zip code, in the Old Village neighborhood of Mount Pleasant. Nearby schools include Mt. Pleasant Academy, Moultrie and Lucy Beckham, and amenities include Tennis Court(s) and Trash. The best way to learn about this home for sale is to come and view it in person, all you have to do is call and ask me, to set up your complimentary showing of 111 Live Oak Drive.

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111 Live Oak Drive is a waterfront single family detached 5 bedroom property in Old Village in the city of Mount Pleasant which is listed for $19,500,000. The total heated square footage is about 6,150 sq ft, and this translates to $3,171 per sq ft. This home was built in 1830 and has 5 full and 2 half bathrooms. Exterior features include Boatlift,Dock - Existing,In Ground.

Properties marked with the Broker Reciprocity logo are provided courtesy of Charleston Trident Multiple Listing Service, Inc. The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the Charleston Trident Multiple Listing Service. Real estate listings held by brokerage firms other than the website owner are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. The broker providing this data believes it to be correct, but advises interested parties to confirm them before relying on them in a purchase decision. Information is provided exclusively for consumers' personal, non-commerical use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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