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$1,150,000
3 Beds ⋅ 3 Baths ⋅ 26020890 MLS
Discover the rare combination of space, convenience and exceptional parking at 71 Gadsden Street. This three-bedroom residence offers desirable single-level living, with each generously sized bedroom featuring its own private en suite bath--an ideal arrangement for a full-time residence, second home or investment property.The home's spacious living areas provide plenty of room for relaxing and entertaining, while a dedicated laundry room adds everyday functionality.A newer roof and appliances installed in 2018 offer additional peace of mind. One of the property's most remarkable features is off-street parking for four to five vehicles, a true luxury in downtown Charleston. Perfectly positioned near the College of Charleston, MUSC and Roper Hospital, the property offers excellent potential for student or medical housing while remaining equally appealing as a comfortable primary residence. Enjoy easy access to Charleston's celebrated restaurants, neighborhood cafés, shopping, parks and the historic streets of the peninsula. With large rooms, private baths, single-level living and extraordinary parking, 71 Gadsden Street presents a versatile downtown opportunity that is increasingly difficult to find. Come experience the space, flexibility and Charleston lifestyle this property has to offer.

71 Gadsden Street, Charleston

Listing courtesy of Listing Agent: Lisa Patterson from Listing Office: Daniel Ravenel Sotheby's International Realty.

$3,499,000
4 Beds ⋅ 3.5 Baths ⋅ 26020111 MLS
Exceptional opportunity to purchase this historic Harleston Village property as-is and bring your vision to life. Whether you're a buyer looking to customize your dream home or an investor seeking your next signature project, this property offers incredible potential. Situated on a rare double lot, the home already features a pool and pool house, with the interior fully demolished and ready for construction to begin. Construction plans provide the opportunity to expand to approximately 5,000 square feet, blending functionality with Charleston's timeless character. The renovation is designed to preserve the home's historic architecture while incorporating all new major systems, including electrical, plumbing, HVAC, and structural improvements. Buyers have the flexibility to work with the seller's experienced in-house builder or bring their own licensed contractor to complete the project. A unique chance to create a one-of-a-kind historic residence in one of downtown Charleston's most desirable neighborhoods

18 Trumbo Street, Charleston

Listing courtesy of Listing Agent: Eric Davis from Listing Office: EXP Realty LLC.

$5,695,000
4 Beds ⋅ 4.5 Baths ⋅ 26019552 MLS
Reimagined in the heart of Harleston Village, this restored residence blends Charleston architecture with an elevated floor plan designed for today's lifestyle. The home was raised, allowing for additional ground floor square footage & creating flexibility for a private gym, theatre, wine room, office, game room, &/or additional entertaining space.BAR Approved Pool & ADU in hand - Seller willing to complete for additional cost. The residence features an expansive chef's kitchen with oversized island, premium Thermador appliances & scullery. Elegant wall paneling, refined architectural details & beautifully restored historic elements can be found throughout the home. The luxurious primary suite offers a spa like bath with an oversized double shower &large private porch overlooking the gated backyard. Standout exterior features include double piazzas, two additional porches in the rear, a large backyard with room for a pool & driveway parking for multiple vehicles. ***BAR Approved Pool & Permit. BAR Approved ADU (~444 sqft, detached). Seller willing to complete either or both of the above projects for an additional cost. Seller is also willing to further customize & build out the extensive ground floor flex space for an additional cost.*** May 2026 Appraisal lists valuation at $5.9m ($250k less than list price). Ideally located just moments from Charleston's many restaurants, shops, Colonial Lake & King Street, this is a rare opportunity to own a like new, fully restored historic home with modern functionality in one of downtown Charleston's most desirable neighborhoods.

175 1/2 Wentworth Street, Charleston

Listing courtesy of Listing Agent: Jennifer Snowden from Listing Office: The Cassina Group. 843-628-0008
$3,399,000
7 Beds ⋅ 5.5 Baths ⋅ 26019450 MLS
Introducing 41 Pitt Street, a rare 7 bedroom 5.5 bath home with 4 off street parking. One of downtown Charleston's most affordable luxury renovations, this property masterfully blends timeless historic character with sophisticated contemporary design in the heart of Harleston Village, one of Downtown Charleston's most desirable neighborhoods. Completely reimagined from top to bottom, this extraordinary residence has been thoughtfully redesigned to create an exceptional luxury lifestyle while preserving the architectural charm that makes Historic Charleston one of America's most celebrated destinations. Featuring 7 bedrooms, 5.5 bathrooms, and an exceptionally versatile floor plan, the home offers ideal balance of elegant entertaining, everyday comfort and outstanding investment potentialSurrounded with natural light, the main level showcases expansive open-concept living spaces where a designer chef's kitchen and scullery with ice maker, wine fridge, bar sink seamlessly connects to the spacious great room and dining area. Oversized walls of collective glass, soaring 11 ft up to 35 feet ceilings, integrated surround sound, and refined contemporary finishes and mahogany custom doors, create an atmosphere that is both sophisticated and inviting, perfect for intimate gatherings or large-scale entertaining. Every detail has been carefully curated, including beautifully restored heart pine flooring, custom cheery wood cabinetry, premium marble surfaces, professional-grade stainless appliances, designer lighting fixtures, designer tile, brass hardware, private study/office and elegant architectural details that elevate every room. A beautifully appointed kitchen scullery enhances both functionality and entertaining, offering additional preparation space, storage, and serving areas for effortless hosting. The luxurious primary suite is conveniently located on the main living level, creating a private sanctuary complete with a spacious walk-in closet and an elegant spa-inspired bath featuring dual vanities, an oversized walk-in shower, and carefully selected designer finishes. An additional private entry guest suite apartment on the first floor offers exceptional flexibility for visiting family or luxury guest accommodations with rental income opportunity. The second level has been recently expanded to include 2 additional bedrooms recently added and one full bath, creating generous accommodations that include 7 total bedrooms, a large entertainment lounge area that can easily be another bedroom in the main house and multiple flexible gathering spaces designed for today's modern lifestyle. Outside, the possibilities are equally impressive.The expansive side yards offers the perfect canvas for creating a spectacular resort-style pool and private outdoor retreat, complemented by covered veranda, spacious entertaining areas, and beautifully designed outdoor living spaces that embrace Charleston's year-round climate. There is also room to build a single car garage in the driveway. Striking architectural features including elevated construction, dramatic glass windows, standing-seam metal roof, and clean contemporary lines--create a home that is both architecturally distinctive and timelessly elegant. Beyond its appeal as an extraordinary primary residence or luxurious second home, 41 Pitt Street also represents an exceptional income-producing opportunity. Located just blocks from Medical University of South Carolina and College of Charleston, the property is ideally positioned for premium executive, medical, academic, or luxury vacation rental. The attached guest apartment with full kitchen further enhances its flexibility and income potential, with projected rental information available in the listing package. Residents will enjoy a truly walkable Charleston lifestyle, just moments from acclaimed restaurants, boutique shopping, neighborhood cafés, Colonial Lake, waterfront parks, marinas and the city's vibrant cultural and culinary scene. Recognized year after year as #1 of America's finest cities, Historic Charleston offers an unmatched combination of rich history, world-class dining, beautiful waterfronts, and timeless Southern elegance. 41 Pitt Street is more than a beautifully renovated home, it is an opportunity to own a signature residence that combines architectural beauty, exceptional craftsmanship, remarkable flexibility, and one of the finest downtown lifestyles Charleston has to offer.

41 Pitt Street, Charleston

Listing courtesy of Listing Agent: Kristen Krause from Listing Office: Remax Executive.

$6,995,000
6 Beds ⋅ 6.5 Baths ⋅ 26012051 MLS
This spectacular home overlooking Colonial Lake was designed by noted architect Bradford Lee Gilbert and constructed by Dr. Manning Simons for his bride in 1902. Set along one of downtown Charleston's most distinguished and picturesque avenues, 22 Rutledge Avenue is a rare, fully reimagined historic residence that seamlessly blends timeless architecture with exceptional modern updates. Behind its stately facade lies a thoughtfully curated home offering elegant interiors and resort-style outdoor living creating a true turnkey opportunity in the heart of the city.Handsome black and white marble surround the entry fountain leading to the front door. The spacious entry foyer is complemented by all new interior and exterior lighting that enhances the home's classic architectural details. The main residence is comprised of 4 Bedrooms and 4 ½ Baths and includes living and dining rooms that are generously sized, along with a large den for family gatherings. Leaded glass windows add to the charm of these beautiful rooms. An adjacent wet bar completes the large area for entertainment and relaxation. A fully renovated kitchen serves as the centerpiece of activity and hosts easy flow for everyday living and comfort. A wall of windows from the kitchen overlooks the beautifully landscaped garden and pool area. The fourth bedroom is currently used as extra large closet but can be returned to its original use. A full house water filtration system and working fireplaces throughout complete the luxury downtown lifestyle. Complementing the property is a beautifully restored carriage house that offers remarkable living and entertaining flexibility. The early 19th century house contains 2 Bedrooms and 1½ Baths and features a fully restored kitchen, den, downstairs bathroom and laundry area. Updated systems throughout make the carriage house ideal for guests or extended living. With its exceptional level of renovation, refined finishes, and prime location, 22 Rutledge Avenue stands as a rare offering, gracefully honoring Charleston's architectural heritage while delivering the comfort, style, and ease of modern luxury living.

22 Rutledge Avenue, Charleston

Listing courtesy of Listing Agent: Robertson Allen from Listing Office: The Cassina Group. 843-628-0008
$7,998,000
6 Beds ⋅ 4.5 Baths ⋅ 26010056 MLS
Now Includes Full Addition, ADU, Pool, landscaping package, and full furniture package . 16 Trumbo Street present a unique opportunity in Harleston Village, just steps from Colonial Lake. The property is currently undergoing a full studs-out renovation with an addition, including a house lift to allow for a new foundation and enclosure space below. Conditioned enclosure space (option to ADD up to additional 1500 SF)Plans and design selections are in place but can be modified, offering flexibility for a buyer to make adjustments during construction. Opportunity to meet with the development team to review plans, selections, and overall scope.Golf cart to all your favorite restaurants

16 Trumbo, Charleston

Listing courtesy of Listing Agent: Eric Davis from Listing Office: EXP Realty LLC.

$8,995,000
4 Beds ⋅ 5.5 Baths ⋅ 26009816 MLS
Set on a rare double lot with historic ties to the original Roper Hospital, this exceptional Charleston single residence seamlessly blends architectural pedigree with inspired modern design. Originally constructed in 1995 by an architect for his own family, and honored with a 1996 Preservation Society of Charleston Carolopolis Award, this distinguished home has been completely reimagined through a meticulous, down-to-the-studs renovation in 2023 and 2024 addition, including a thoughtfully designed pool house and stunning new primary suite by architect Sebastian von Marschall. Beyond its classic stucco facade, the interiors are both sophisticated and expressive, artfully layering antique furnishings with bold contemporary elements--statement lighting, abstract art, richly saturated paintand striking wallpapers throughout. The reconfigured floor plan enhances flow and livability, with the kitchen and dining spaces repositioned to create a more intuitive connection for everyday living and entertaining. A gracious foyer sets the tone, flanked by elegant formal living and dining rooms. The dining room is a true showpiece, featuring panoramic Paul Montgomery mural wallpaper, a Regina Andrews chandelier, and an antiqued mirrored inset ceiling, with French doors opening to a charming brick terrace. The designer kitchen, centered around a marble island, flows seamlessly into a warm and inviting den, while a fully appointed butler's pantry - custom designed for china, glassware, and entertaining - adds both beauty and function. A wet bar with beverage refrigeration and soda fountain, a powder room, and a private office complete the main level. Upstairs, guest accommodations are equally curated, highlighted by richly layered color palettes and designer finishes, including Thibaut "Yukio" wallpaper paired with Farrow & Ball hues. The third floor offers a whimsical bedroom retreat with dormered ceilings, window seats, and a distinctive full bath centered around a glass-enclosed shower. Privately situated above the addition and connected by a hyphen, the primary suite is a serene sanctuary overlooking the gardens and pool. The suite features an extraordinary, boutique-style dressing room and closet with illuminated cabinetry, marble-topped island, and custom display storage. The primary bath is equally dramatic, anchored by a striking black-tiled shower and dual vanities. Designed as a seamless extension of indoor living, the pool house serves as both a stylish lounge and the heart of entertaining. Inspired by Dorothy Draper, the space features Brunschwig & Fils "Les Touches" wallpaper, marble checkerboard flooring, and vibrant textiles, creating a playful yet refined atmosphere. With a wet bar, dishwasher, and dual powder bathrooms, the pool house plays double duty for powerful party hosting. At the center of the property, the landscaped gardens are the true showpiece--anchoring the main house and addition with a resort-like setting that includes a pool, brick hardscaping, lush plantings, and curated outdoor living spaces. Entry is through iron gates framed by brick columns and gas lanterns, leading to a circular brick drive, fountain, and koi pond--an arrival experience that is both grand and unmistakably Charleston. This is a rare opportunity to own a deeply considered, design-forward residence where historic inspiration and modern luxury converge in one of Charleston's most distinctive settings. This spectacular property was recently featured in both television and print. Watch Season 3 Episode 6 of "Where We Call Home" on HBO Max and Apple TV. It was also featured in the April 2024 issue of Charleston Magazine, as well as the December 2025 holiday issue of Charleston Magazine, showcasing this very special home. Three private, deeded off-street parking spaces behind the property provide coveted downtown parking and security. Please see list of upgrades and design details.

140 Queen Street, Charleston

Listing courtesy of Listing Agent: Leslie Turner from Listing Office: Maison Real Estate.

$5,450,000
10 Beds ⋅ 10.5 Baths ⋅ 26009115 MLS
A renewed opportunity to pursue one of Harleston Village's rare historic compounds. The prior buyer elected not to proceed at no fault of the seller. Tucked within the heart of Harleston Village, 49 Smith Street presents an extraordinarily rare opportunity to own one of downtown Charleston's most distinctive historic compounds. Originally anchored by a circa 1860 main residence (5000sf) and complemented by a separate circa 1880 carriage house (2500sf), this landmark European villa-style estate blends architectural pedigree, private compound living, and exceptional long-term potential across approximately 7,525 square feet.Behind its striking two-tone English Flemish brick façade, the property unfolds as a true multi-structure estate--an offering seldom found in one of Charleston's most sought-after neighborhoods. The sprawling three-story main residence encompasses over 5,000 square feet. It is currently configured as seven independent residences, many of which feature original fireplaces, stately wood interiors, hand-poured glass windows, and an abundance of natural light that pours through the historic façade. Complementing the main house is a fully private two-story carriage house exceeding 2,500 square feet, accessed through its own gated entry and complete with a garage, expansive porch, and elevated rooftop terrace. This secluded secondary residence offers an extraordinary living experience--ideal as a luxurious guest residence, private office, studio, or boutique retreat. What sets 49 Smith apart is the extraordinary balance of immediate utility and future vision. The opportunity to thoughtfully reimagine the main residence into one of Harleston Village's most compelling private homes has already been carefully explored, with preliminary architectural and construction guidance reinforcing the extraordinary potential of the estate. For the right buyer, this presents a rare chance to create a grand three-story historic residence while preserving the carriage house as a private, design-forward complement--an offering that would be exceptionally rare within the downtown Charleston market. Equally compelling is the lifestyle this property affords today. Morning light filters through the hand-poured glass windows, illuminating preserved historic interiors and rich architectural details. Evenings unfold across the veranda patios and rooftop terrace, creating a layered indoor-outdoor living experience that feels both private and deeply connected to the rhythm of downtown Charleston. Just moments from Colonial Lake, King Street, Broad Street, and the iconic Wentworth Mansion, the location offers a walkable lifestyle surrounded by Charleston's most celebrated architecture, dining, shopping, and cultural landmarks. Whether envisioned as a legacy private residence, a multi-generational compound, or an income-producing hold with exceptional upside, 49 Smith Street offers a level of scale, flexibility, and architectural significance that is rarely available. This is more than a property--it is a once-in-a-generation opportunity to steward one of Harleston Village's most remarkable estates into its next chapter.

49 Smith Street, Charleston

Listing courtesy of Listing Agent: Harrison Bocook from Listing Office: EXP Realty LLC.

$3,500,000
3 Beds ⋅ 3.5 Baths ⋅ 26008890 MLS
Welcome to 72 Halsey Boulevard, an exceptional residence in the coveted Halsey Park enclave - where classic Charleston character is seamlessly paired with refined contemporary design. This is a home that truly stands apart: timeless Lowcountry flair, elevated with modern appointments that make it a rare find in downtown Charleston.Situated along prestigious Halsey Boulevard, this 3-bedroom, 3.5-bath residence spans more than 2,900 square feet across three impeccably designed levels. From the moment you enter, the home feels bright, inviting, and effortlessly stylish. A light-filled foyer sets the tone, leading into a spacious living room anchored by a sleek linear fireplace - an elegant modern counterpoint to the home's traditional architectural details. Double piazza access on eitherside captures Charleston's signature breezes and creates a natural flow between indoor and outdoor living. A full-width covered piazza extends the living space outdoors, ideal for alfresco dining and entertaining, while a second upper porch offers an additional private retreat. Throughout the home, thoughtful details elevate everyday living: triple molding, integrated Sonos speakers, top-tier designer plumbing fixtures, Lutron lighting controls, and J. Geiger electric shades blend luxury with convenience in a way that feels both intentional and effortless. The main living level is completed by a beautifully appointed kitchen featuring high-end Thermador appliances, custom cabinetry, and a generous dining area that functions equally well for intimate dinners or gracious entertaining. A private elevator servicing all three floors, along with a home generator, adds a level of comfort and ease rarely found in downtown residences. The second floor is anchored by a serene primary suite with a spacious walk-in closet, spa-like bath with heated floors and direct access to its own private porch--perfect for morning coffee or quiet evenings overlooking Alberta Long Lake and the City Marina. Two additional En suite bedrooms and a dedicated laundry room round out the level, offering both comfort and practicality. The ground level is a standout, featuring an oversized garage, abundant storage, and a remarkable covered entertainment area with an open patio. Whether envisioned as a game-day gathering space, fitness studio, or private outdoor lounge, this level provides flexibility few Charleston homes can match. With low-maintenance living, abundant storage and an unbeatable location just minutes from the Battery, MUSC, and Charleston's finest dining and galleries, 72 Halsey Boulevard is more than a home--it is a rare opportunity to experience authentic Charleston living, thoughtfully reimagined for today.

72 Halsey Boulevard, Charleston

Listing courtesy of Listing Agent: Mary Lou Wertz from Listing Office: Maison Real Estate.

$2,225,000
3 Beds ⋅ 2.5 Baths ⋅ 26000878 MLS
Available for presale now and move in summer of 2026! We are in the finish selection phase. This home has undergone a complete studs-out renovation and has been professionally lifted with a new reinforced foundation, brand new electrical, plumbing, and finishes while blending modern construction integrity with timeless Lowcountry charm. Every detail has been thoughtfully curated, featuring high-end selections, custom millwork, refined materials, and elevated design throughout, while preserving the character and proportions that define Charleston's historic homes. Located just steps from the scenic paths of Colonial Lake, 10 Trapman Street offers a rare opportunity to own a fully reimagined historic Charleston residence in the heart of Harleston Village.The floor plan is both functional and elegant, ideal for modern living and entertaining. Perfectly positioned near Broad Street, MUSC, and the College of Charleston, this turnkey residence delivers walkability, craftsmanship, and long-term peace of mindan exceptional offering in one of downtown Charleston's most desirable neighborhoods. Proposed Elevations - Construction Started

10 Trapman Street, Charleston

Listing courtesy of Listing Agent: Christopher Smith from Listing Office: SERHANT.

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