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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.

$1,495,000
2 Beds ⋅ 2.5 Baths ⋅ 26020692 MLS
Welcome to 1 Bennett Street, Unit 3--a beautifully renovated historic residence offering more than 2,000 square feet of refined Charleston living directly across from Cannon Park. Located in the heart of Harleston Village, this distinctive three-story condominium blends the architectural character of an 1890 home with the comfort and craftsmanship of a thoughtfully completed renovation. Inside, Brazilian cherry hardwood floors, soaring ceilings, custom millwork and abundant natural light create a warm and elegant setting. The spacious kitchen features oversized cherry cabinetry, granite countertops, a large island and a gas range, while multiple living areas provide flexibility for entertaining, working from home or welcoming overnight guests.The residence includes two bedrooms, two-and-one-half baths, generous closets, a gas-log fireplace, wet bar, full front porch and private deck. Step outside and enjoy one of downtown Charleston's most desirable neighborhoods, with Cannon Park just across the street and the city's renowned dining, shopping, universities and cultural attractions nearby. Historic character, impressive interior space and an exceptional Harleston Village location come together in a home that offers a truly distinctive Charleston lifestyle.

1 Bennett Bennett Unit #3, Charleston

Listing courtesy of Listing Agent: Joe Brown from Listing Office: AgentOwned Realty.

$2,100,000
5 Beds ⋅ 26020230 MLS
Prime Downtown Charleston Investment Opportunity with Exceptional Income Potential. Located in the heart of historic downtown Charleston, just two blocks from Broad Street and around the corner from Colonial Lake, this exceptional income-producing property offers an unbeatable location within walking distance of the city's premier restaurants, shopping, parks, and historic landmarks.Featuring three separate living units, this versatile property presents an outstanding opportunity for investors, owner-occupants, or multi-generational living with a proven rental history. Sold As-Is.

11 Smith Street, Charleston

Listing courtesy of Listing Agent: Yana Lynch from Listing Office: Fidei Real Estate Int'l LLC.

$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.

$710,000
2 Beds ⋅ 1.5 Baths ⋅ 26019993 MLS
Overlooking iconic Colonial Lake in the heart of Harleston Village, this beautifully renovated Baker House residence offers the quintessential Charleston lifestyle. With two bedrooms, one-and-a-half baths, and a coveted location just moments from King Street, award-winning restaurants, charming cafes, art galleries, and historic landmarks, this is an exceptional opportunity to own a sophisticated lock-and-leave residence in one of downtown Charleston's most desirable neighborhoods.Thoughtfully redesigned in 2017, the home showcases timeless finishes and meticulous craftsmanship throughout. The designer kitchen features custom shiplap detailing, elegant Calacatta quartz countertops, custom cabinetry, and updated appliances, creating a space that is as functional as it is beautiful.Both bedrooms are enhanced with custom built-in storage, maximizing style and efficiency. The full bath offers a spa-inspired feel with a custom vanity topped with Venato quartz, porcelain sinks, and a beautifully tiled walk-in shower, while the charming powder room features a Bianco Piedrafina countertop and porcelain sink. One of the property's most valuable amenities is its designated off-street parking space, complemented by eight additional guest parking spaces--a rare luxury in historic downtown Charleston. Whether you're searching for a full-time residence, a charming pied-à-terre, or an investment in one of the city's most coveted neighborhoods, this exceptional home offers effortless living in an unbeatable setting. Tennis courts and pickleball courts readily available nearby!

55 Ashley Avenue Unit #Apt 5, Charleston

Listing courtesy of Listing Agent: Nancy Hoy from Listing Office: Carolina One Real Estate. 843-779-8660
$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.

$1,315,000
3 Beds ⋅ 3 Baths ⋅ 26018888 MLS
Welcome to Downtown living at its absolute finest! Located in highly desirable Harleston Village, this stunning and exceptionally spacious 1,794 sq ft condo features 3 bedrooms and 3 baths across a bright, light-filled layout. Enjoy quintessential historic charm with beautiful heart pine floors, handsome built-ins, Carrara marble kitchen countertops and fireplaces. Relax or entertain on your massive private piazza while soaking in beautiful treetop and rooftop views. The unbeatable location is just steps away from local favorites like Merci, a quick 6-minute walk to the College of Charleston, and blocks from premier King Street shopping. Complete with rare off-street parking. Don't miss this Harleston Village gem!

25 Montagu Street Unit #Apt C, Charleston

Listing courtesy of Listing Agent: Jayson Wingfield from Listing Office: Redfin Corporation.

$1,275,000
2 Beds ⋅ 2 Baths ⋅ 26017686 MLS
Price Reduction - Luxury Charleston Living in the Heart of Harleston Village! This stunning newly renovated in 2026 first-floor residence, is a 2 bedroom 2 bath with the ability to convert front room into a 3rd bedroom and 3rd bath. The designer kitchen and spa-inspired baths feature premium finishes, custom millwork, wide-plank flooring, high-end fixtures, and luxury stainless appliances throughout. Thoughtfully selected to deliver a truly turnkey living experience. Enjoy the convenience of 2 off-street parking spaces, a private rear porch and entrance, and an unbeatable walkable location just steps from Colonial Lake, King Street shopping and dining, world-class restaurants, cafes, and Charleston's iconic historic downtown lifestyle.This is a exceptional opportunity to own a luxury condo. Whether you are seeking a primary residence, luxury second home, or investment rental opportunity, Unit A offers the perfect combination of elegance, location, and effortless Charleston living.

63 Montagu Street Unit #A, Charleston

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

$2,895,000
26016962 MLS
112 Rutledge Avenue presents a rare opportunity to acquire a beautifully renovated, mixed-use investment property in the heart of Harleston Village. Positioned in one of Charleston's most sought-after neighborhoods, this asset offers a strong blend of stable income and future upside. The ground-floor medical office space is secured by a long-term lease through December 2029 at attractive market rates, providing consistent and reliable cash flow. Above, the second and third floors feature three residential units totaling nine bedrooms and four bathrooms. The residential component is nearly fully leased, with one recently renovated unit (Unit D) currently available--ideal for an owner-occupant or to be leased at market rates to further enhance income. There are ten (10) dedicated parking spa112 Rutledge Avenue presents a rare opportunity to acquire a beautifully renovated, mixed-use investment property in the heart of Harleston Village. Positioned in one of Charleston's most sought-after neighborhoods, this asset offers a strong blend of stable income and future upside. The ground-floor medical office space is secured by a long-term lease through December 2029 at attractive market rates, providing consistent and reliable cash flow. Above, the second and third floors feature three residential units totaling nine bedrooms and four bathrooms. The residential component is nearly fully leased, with one recently renovated unit (Unit D) currently available--ideal for an owner-occupant or to be leased at market rates to further enhance income. There are ten (10) dedicated parking spaces, a highly desirable amenity in this area. Six spaces are leased to the medical office tenant, while the remaining four are allocated to the residential units, generating additional rental income. Excellent Downtown Charleston location in the Historic District and adjacent to the hospital district, walking distance to the College of Charleston, Medical University of South Carolina and many retail sites. With recent renovations, strong in-place income, and the flexibility of a vacant unit, 112 Rutledge Avenue offers investors a compelling, turnkey opportunity in a premier location. TMS #: 457-03-02-120, 457-03-02-162, 457-03-02-163, 457-03-02-165, 457-03-02-165.

112 Rutledge Avenue, Charleston

Listing courtesy of Listing Agent: Jenna Philipp from Listing Office: Palmetto Commercial Prop, LLC.

$949,000
2 Beds ⋅ 1 Baths ⋅ 26016154 MLS
Nestled on charming Pitt Street in downtown Charleston, the fully renovated upstairs residence at 8 Pitt Street combines classic Charleston character with modern updates in an exceptional South of Calhoun location. Just a short walk from the College of Charleston, MUSC, King Street, Colonial Lake, and many of the city's most popular restaurants, coffee shops, and boutiques, this home offers the convenience and energy of downtown living with the charm of a historic neighborhood setting. With easy access to everyday essentials, local dining, and Charleston's vibrant downtown atmosphere, this location offers the ideal blend of comfort and convenience.Inside, soaring ceilings, refinished original hardwood floors, and abundant natural light create a bright and welcoming living environment. Two generously sized bedrooms are complemented by a dedicated office or flex space, offering versatility for remote work, studying, guests, or additional storage. The redesigned kitchen features quartz countertops, custom cabinetry, stainless steel appliances, and a large island ideal for entertaining. Additional improvements include new plumbing, updated gas lines, a tankless water heater, and a complete electrical rewire with a new panel. Restored historic windows, fresh exterior paint, and two dedicated off street parking spaces complete this beautifully updated downtown Charleston residence.

8 Pitt Street Unit #B, Charleston

Listing courtesy of Listing Agent: Carter Rowson from Listing Office: The Exchange Company, LLC.

$709,000
1 Beds ⋅ 1 Baths ⋅ 26015489 MLS
The Baker House in Harleston Village has long been regarded as one of the best-built condominium buildings in one of Charleston's most coveted neighborhoods, and Residence 17 is its most thoughtfully renovated unit.Completely reimagined in 2024 by acclaimed NYC interior designer Tina Ramchandani, the residence was rebuilt from the studs out -- new electrical, plumbing, HVAC, and ductwork -- and finished with materials and craftsmanship rarely seen at this scale. Oversized windows pour natural light into the home, where exposed brick meets European custom cabinetry & Visual Comfort & Co. lighting. The kitchen is built for amateur and professional chefs alike, with concealed Fisher & Paykel appliances, an induction cooktop, & a lockable winefridge. The primary suite is a quiet retreat with treetop views over Moultrie Park, all custom closets with extra-tall doors, and a spa-like bath finished in Italian terrazzo, handmade Spanish subway tile, and Grohe and Duravit fixtures. A full-sized washer and dryer are tucked into a hall closet with room to spare. For a downtown Charleston condo, the ownership details are exceptional. The HOA is financially sound. The unit comes with one deeded parking space and the ability to request a second -- a real advantage in a city where parking is becoming limited. Private storage and dedicated bike storage are included as well. Step outside and Colonial Lake, City Marina, tennis courts, Pilates studios, and Charleston's best restaurants are all within a short walk. Residence 17 offers something genuinely uncommon: a turnkey downtown pied-à-terre in a building that was built -- and is maintained -- to last.

55 Ashley Avenue Unit #17, Charleston

Listing courtesy of Listing Agent: Margaret Von Werssowetz from Listing Office: Maison Real Estate.

$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
$1,250,000
3 Beds ⋅ 2.5 Baths ⋅ 26012484 MLS
Nestled on a coveted corner lot in the heart of Harleston Village, this refined townhome offers a rare blend of historic charm and elevated modern living--just steps from Colonial Lake and a short walk to the Charleston Harbor. Welcome to your quintessential Charleston pied-a-terre--an elegant retreat designed for both effortless living and sophisticated entertaining.Within this exclusive eight-residence enclave, this is the only unit offering its own private off-street parking space, complemented by two additional shared spaces--an extraordinary convenience in downtown Charleston. Even more exceptional, there are no regime fees or HOA, providing unmatched flexibility and value.Inside, the home has been professionally staged, showcasing a thoughtfully curated aesthetic that highlights the home's natural light and refined finishes. The main level flows seamlessly from a gracious living room into a formal dining space and an updated kitchen featuring granite countertops and stainless steel appliances--perfect for intimate dinners or hosting guests in style. Upstairs, three well-appointed bedrooms offer comfort and privacy, while the recently remodeled bathrooms feature designer tile and elevated finishes, creating spa-like retreats throughout the home. A convenient powder room on the main level adds to the thoughtful layout. Step outside to your private downtown Charleston courtyard oasis, ideal for morning coffee or evening gatherings, complete with a storage shed/workshop for added functionality. There is also extensive, accessible attic storage space! This is a rare opportunity to own a beautifully upgraded, low-maintenance residence in one of Charleston's most desirable neighborhoods-- where timeless elegance meets modern convenience, all just steps from the best of downtown living.

2 Gadsden Street Unit #D, Charleston

Listing courtesy of Listing Agent: Mikki Ramey from Listing Office: Healthy Realty LLC. 843-478-1684
$750,000
1 Beds ⋅ 1 Baths ⋅ 26011535 MLS
Step into timeless Charleston charm in this beautifully preserved 1855 residence, known as the Cooper-O'Conner House. Rich with character, the home features soaring ceilings, original gleaming heart pine floors, and two inviting fireplaces with gas logs. The kitchen opens to a private rooftop deck--perfect for relaxing or entertaining above the city.Additional highlights include off-street parking and an unbeatable location just steps from Colonial Lake and Burbage's Corner Store, with King Street's renowned shopping and dining only a few short blocks away. A rare opportunity to own a piece of history with modern comforts in the heart of downtown.

180 Broad Street Unit #E, Charleston

Listing courtesy of Listing Agent: Lois Lane from Listing Office: Lois Lane Properties.

$4,695,000
26011256 MLS
176-178 Broad includes 3 buildings that harmoniously blend historic charm with modern luxury. This exceptional property encompasses 9 units, (4) 1 bed/1 bath units, (4) 2 bed/2 bath units, & (1) 2 bed/1 bath unit totaling 14 bedrooms & 13 bathrooms. These units have been meticulously updated to provide modern comforts while preserving the historic elements that make Charleston properties so desirable. Residents will appreciate features such as exposed wood beams, decorative fireplaces, stunning wood floors, piazzas, & spiral staircases. Additionally, 9 off-street parking spaces are available & this property has the potential for a condo conversion. Perfectly situated close to Colonial Lake, this is an extraordinary blend of history, luxury, & prime location, making it an ideal investment.These properties have an approved condo conversion with HPR documents ready for filing if desired, offering the opportunity to keep as a cash flowing property or sell off units individually for highest & best return! Two commercial pools have been approved should a buyer wish to install pools.

176-178 Broad Street, Charleston

Listing courtesy of Listing Agent: Jonathan Holt from Listing Office: Keller Williams Realty Charleston West Ashley.

$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.

$950,000
2 Beds ⋅ 2.5 Baths ⋅ 26006116 MLS
HARLESTON VILLAGE PIED-A-TERRE! Imagine living in the heart of historic downtown Charleston, where your mornings begin with a stroll to Colonial Lake and your evenings end in the vibrant King Street shopping district. Tucked away ''Slightly North of Broad,'' 5 Trapman Street is more than just a home--it's your invitation to the ultimate Lowcountry lifestyle.This beautifully renovated townhome offers the rare ''lock-and-leave'' convenience without the constraints of HOA or regime fees. Inside, you'll find an airy, open-concept layout glowing with natural light, rich hardwood floors, and designer touches from the top-to-bottom renovation.The HVAC was recently replaced, so the next owner can feel confident the home will stay cool and comfy during the Charleston summer and warm during the winter for years to come. Whether you're hosting friends in your private outdoor living space or enjoying the quiet charm of the neighborhood, this move-in-ready sanctuary is a blank canvas just waiting for your personal touch. Parking downtown is no problem on this street. Plenty of available street parking and a dedicated bricked area that can easily fit a golf cart or moped.

5 Trapman Street Unit #Unit 2, Charleston

Listing courtesy of Listing Agent: Brian Beatty from Listing Office: Keller Williams Realty Charleston.

$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.

$1,225,000
3 Beds ⋅ 2.5 Baths ⋅ 25026090 MLS
Move-in ready, lock-and-leave, tastefully updated 2-story, top floor unit in the Baker House, along the banks of Colonial Lake in historic downtown Charleston's Harleston Village.Condo 23 is luxurious, bright and airy, with a living room anchored by a character-rich original exposed brick wall. The dining room is surrounded by distinctive arched windows overlooking Colonial Lake. The stylish kitchen has stainless steel appliances, quartz countertops, and a walk-in pantry. Upstairs, the master bedroom has an adjoining bath, dual closets for plenty of storage, and views of Colonial Lake. A second bedroom also has 2 closets and an en suite full bath with expansive views of the city. The third bedroom is currently used as an office and includes a full-sized washer and dryerColonial Lake. The stylish white-on-white kitchen has stainless steel appliances, quartz countertops, and a walk-in pantry. The open layout makes the home feel more like a private residence than an apartment. Whether used as a primary residence, a lock-and-leave second home, or an investment property, the setting is especially appealing for buyers who want historic charm without the maintenance demands of a single-family property. Upstairs are 2 comfortable bedrooms plus a flexible third room, currently used as an office, with a full-size stacked laundry closet. This space works beautifully as a dedicated work-from-home area, guest overflow, creative studio, or additional sleeping space, depending on your needs. The primary bedroom has dual closets for plenty of storage and an adjoining bath. The second bedroom also has 2 closets as well as an en suite full bath. Baker House ownership includes valuable downtown conveniences including 2 off-street parking spots, bicycle storage, and a secured storage locker. The building's comprehensive monthly regime supports the care and maintenance of the landmark building, offering a simplified ownership experience. Baker House sits directly across from Colonial Lake, providing access to its park, gardens, and walking/jogging paths. Beloved by Charlestonians for generations, Colonial Lake has been described as a "serene oasis nestled in the heart of Charleston" (Agoda travel guide) and a "treasure for us all" (Charleston Magazine). Residents gather here year-round for morning walks, evening strolls, dog walking, picnics, and some of the most picturesque views in the Historic District. A landmark $5.9 million restoration was completed in 2016, with an additional garden revitalization undertaken in 2025, ensuring the park remains one of Charleston's most beautiful and thoughtfully maintained public spaces. Today, the picturesque park is surrounded by grand old homes and attracts families, dog walkers, joggers, and visitors. Right behind the building is Moultrie Playground, with public tennis courts, pickle ball courts, basketball courts, a playground, and batting cages. These facilities make the area popular with families, outdoor enthusiasts, and fitness buffs alike. In the same block, you can walk to the shops and restaurants in The Jasper. Harleston Village is one of the most walkable areas of the city. Broad Street, King Street, MUSC, the College of Charleston, and some of the city's best dining and shopping are all within easy reach. For the buyer seeking a distinctive Charleston residence with history, views, parking, and location, 55 Ashley Avenue 23 offers a compelling alternative to both newer amenity buildings and higher-maintenance downtown homes. Note: Some images have been virtually staged to help illustrate the potential use and layout of the rooms. Care has been taken to represent the spaces as accurately as possible; however, furnishings, décor, and room presentation are for visualization purposes only. Buyers should verify all information deemed important, including room dimensions, layout, and square footage.

55 Ashley Avenue Unit #23, Charleston

Listing courtesy of Listing Agent: Joyce King from Listing Office: Disher Hamrick & Myers Res Inc.

$7,700,000
28 Beds ⋅ 17029456 MLS
Great location next to the College of Charleston campus. All four properties (31 Coming, 29 Coming, 1 Montagu and 1-1/2 Montagu) are contiguous and must be purchased as a package (will not be sold individually). Parking for approximately 20 cars. All properties are currently leased.

31 Coming Street, Charleston

Listing courtesy of Listing Agent: Doug Berlinsky from Listing Office: Disher Hamrick & Myers Res Inc.

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