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559 Rutledge Avenue, Charleston
$1,278,000
2 Beds ⋅ 2.5 Baths ⋅ 26028224 MLS ⋅ Westside SubDv. ⋅ Active Status
Settle into an authentic Charleston lifestyle in this timeless period house located at 559 Rutledge Avenue. This elegant property blends the soul of a bygone era with modern livability. Defined by its soaring ceilings, original moldings, a striking staircase, heart pine floors, bold fireplace mantels, large windows and French doors, double piazzas, plus an additional upstairs rear porch overlooking the surrounding Charleston gardens. From morning until evening natural light, from the North, East, South and West exposures, filter through large windows into the well proportioned rooms.Each room on the first floor is bright and stylish The impressive front stair hall opens into the living room with built in bookcases and a distinctive fireplace. From the living room the view unfolds across the spacious kitchen to the garden beyond. The thoughtfully designed kitchen is both roomy and functional with abundant cabinetry and stainless steel appliances. The kitchen includes a built in banquet dining area overlooking the garden. Off of the kitchen is an elegantly paneled dining room. The ground floor pantry and laundry room also open onto the Charleston garden. In addition, a generously sized powder room is located on the ground floor. Upstairs the two bedrooms with ensuite bathrooms offer both comfort and privacy, each having high ceilings, large closets and their own private piazzas to enjoy throughout the year. Exterior features include one off street parking space and a charming potting shed in the garden. The Westside - Hampton Park neighborhood is often described as the "Brooklyn of Charleston". A multigenerational historic neighborhood with a buzzing culinary scene, a farmers market, hip bakeries and coffee bars, craft breweries and wine bars are all anchored by Hampton Park, a 60 acre historic green space reminiscent of a smaller New York City Central Park. This part of Charleston is considered one of the most walkable areas in the city with sidewalks and live oak trees lining the streets. The sense of community involvement and connection is ever apparent and welcoming to all. The warmth of historic character, a private garden and breezy piazzas is what makes original Charleston houses so sought after. This property has it all.

559 Rutledge Avenue, Charleston
65 Carolina Street, Charleston
$2,495,000
3 Beds ⋅ 3.5 Baths ⋅ 26027394 MLS ⋅ Westside SubDv. ⋅ Active Status
Situated on desirable Carolina Street, this captivating downtown Charleston home has undergone a comprehensive, ground-up renovation - reimagining the floor plan from the foundation to the roofline while preserving its quintessential historic character. The property makes an immediate impression with striking curb appeal, mature professional landscaping, a custom bluestone and brick front porch, and a newly paved driveway with off-street parking for up to three cars and dedicated golf cart charging. Out back, a private backyard oasis awaits - anchored by an expansive ~300 sq. ft. screened porch, a custom Gunite pool and spa, a gas brick fireplace, and thoughtfully designed outdoor entertaining spaces.Through the entry, all-new white oak hardwood floors, pristine millwork, designer trim, and custom drywall set a sophisticated tone under Visual Comfort lighting fixtures. Off the hallway, double glass French doors open into a private main-floor space--currently styled as a home office/den, but easily utilized as a fourth bedroom. It features dramatic color-drenched blue-green walls, custom cabinetry, and light-filled windows overlooking the street. Beyond, the continuous main level opens into an expansive living space crafted for entertaining. At the heart of the home, the chef's kitchen features custom cabinetry by The Cabinet Store, a double island with exquisite marble finishes, a Perrin & Rowe kitchen sink, and a high-end Thermador appliance suite complete with built-in paneled refrigerator and integrated fridge/freezer drawers. The downstairs water system is equipped with an inline filter and dedicated water pressure booster system. Adjacent to the kitchen, a light-filled dining space flows into a full built-in bar and coffee station with custom cabinetry, glass display uppers, and an under-counter beverage fridge. The adjoining living area draws in natural light through expansive rear windows and double French doors leading directly out to the screened porch. Nearby, a jewel-box powder room features designer wallpaper, a warm wood vanity with stone countertops, unlacquered brass accents, and a woven shade. Unlacquered brass and polished nickel finishes elevate hardware throughout the home. The upper-level houses three light-filled bedroom suites, each featuring custom built-in closets and dedicated en suite bathrooms. Positioned conveniently near the primary suite is a second-floor laundry closet. The primary suite is a serene retreat wrapped in designer wallpaper. It boasts "his and hers" walk-in closets with integrated drawer banks, shoe display shelving, hanging storage, and a scalloped ceiling fixture. Double doors open to a spacious marble bathroom with dual vanities, polished nickel hardware, a private water closet, a glass-enclosed zero-entry wet room, and a freestanding soaking tub. The second bedroom pairs dark hardwood floors with a boutique-inspired bath featuring a soft-pink vanity, scalloped rattan mirror, walk-in shower, and pink mosaic tile. The third bedroom, currently used as a nursery, showcases delicate designer wallpaper and an en suite bath with a grey vanity and detailed mosaic tile. The second bedroom pairs dark hardwood floors with a boutique-inspired en suite bathroom featuring a soft-pink vanity, scalloped rattan mirror, walk-in shower, and pink mosaic tile. The third bedroom upstairs, currently utilized as a nursery, features delicate designer wallpaper and an en suite bathroom with a custom grey vanity and detailed mosaic tiling. Out back, a spectacular resort-style backyard blends indoor and outdoor living for both relaxation and entertaining. It begins on the screened porch, finished with Garapa decking and soaring ceilings. Below, a stone paver patio and a bluestone and brick planter bed surround a custom pool and spa (installed in 2025 by Aquatica), equipped with a gas heater and electric chiller for year-round use. The courtyard also features a gas brick and bluestone fireplace, integrated outdoor lighting, irrigated synthetic turf in front and back, and power outlets throughout the grounds. Behind the scenes, the home's complete structural and infrastructure restoration includes a newly engineered and leveled foundation, a fully encapsulated crawlspace with a dehumidifier, Rain Bird irrigation, recent exterior paint, roof repairs, and all-new electrical, plumbing, HVAC, and insulation. Located outside a flood zone, the home offers exceptional peace of mind within easy reach of the peninsula's premier dining, local boutiques, and vibrant parks.

65 Carolina Street, Charleston
9 Ashton Street, Charleston
$895,000
4 Beds ⋅ 2 Baths ⋅ 26027306 MLS ⋅ Westside SubDv. ⋅ Active Status
A Lowcountry Gem! Classic 1930's Craftsman with full front porch and charming wrought iron details, 4 bedrooms 2 bathrooms located in one of Charleston's most accessible downtown corridor, within walking distance to the Medical District (MUSC, Roper Hospital, VA), The Citadel and Ashley River Marina. Exceptional opportunity for investor or buyer seeking a traditional historic home with significant upside potential. This property has an expansive lot with off street parking and the opportunity for an accessory dwelling unit (ADU), carriage house or 3 car garage structure pending City/BAR approval. Offered AS-IS

9 Ashton Street, Charleston
27 Nunan Street, Charleston
$599,000
3 Beds ⋅ 1 Baths ⋅ 26025523 MLS ⋅ Westside SubDv. ⋅ Active Status
Here's an opportunity to reimagine a charming 3-bedroom, 1-bath Charleston cottage tucked along a quiet one-way street in Charleston's Westside neighborhood. At more than 1,450 square feet, this home offers generous space and a flexible footprint for its next owner's vision. The property is in need of a full renovation, presenting an opportunity to restore its character while creating a home tailored to your style and needs. There are three original fireplaces that are no longer in use but remain as a great architectural feature. Enclosed side and rear yards provide added privacy and room for gardening, entertaining, pets, or outdoor living. The outdoor space may also offer the potential for off-street parking-an especially desirable feature for peninsula living. Conveniently located near MUSC, The Citadel, Publix, Hampton Park and restaurants, the property combines a convenient location with the character of an established Charleston neighborhood. For a buyer ready to take on a renovation, this historic cottage offers space, outdoor potential, and the opportunity to bring a new vision to a classic Charleston home.

27 Nunan Street, Charleston
193 Line Street, Charleston
$1,025,000
4 Beds ⋅ 4 Baths ⋅ 26025511 MLS ⋅ Westside SubDv. ⋅ Active Status
Welcome to 193 Line Street, a completely renovated duplex offering modern comfort and flexible living. Renovated in 2024, this property features two separate residences, each with two bedrooms and two bathrooms. Both units feature open concept layouts with all new kitchens, bathrooms, flooring, HVAC systems, and appliances, plus off-street parking for 2 cars. With 4 bedrooms and 4 bathrooms total, this turnkey property is well suited for investors, owner occupants, or buyers seeking a flexible multi-generational living arrangement. This property combines the convenience of downtown living with the appeal of comprehensive renovations. Classic Charleston-style side porches add genuine Lowcountry charm. Minutes from MUSC, The Citadel, and the peninsula's best restaurants and shops.

193 Line Street, Charleston
4 Carolina Street, Charleston
$1,275,000
3 Beds ⋅ 2.5 Baths ⋅ 26025277 MLS ⋅ Westside SubDv. ⋅ Active Status
Beautifully restored and thoughtfully renovated, 4 Carolina Street pairs historic Charleston character with modern comfort. A recipient of the Preservation Society of Charleston's 2009 Carolopolis Award, the home features gas lanterns, hardwood floors, an exposed brick fireplace and original beams. Open living and dining areas flow into a spacious kitchen, while an updated pantry and laundry area lead to a private backyard with a deck, green space, bamboo-lined fencing and room for up to four off-street parking spaces. Upstairs, the primary suite offers ample closets and an updated ensuite bath, while two bright bedrooms share a full bath. Just blocks from King Street's shops and restaurants, this is Charleston living at its best.

4 Carolina Street, Charleston
174 Fishburne Street, Charleston
$1,575,000
4 Beds ⋅ 4.5 Baths ⋅ 26023439 MLS ⋅ Westside SubDv. ⋅ Active Status
*New Construction* located in downtown Charleston's historic Westside neighborhood! This home offers 4 bedrooms and 4.5 bathrooms, with each bedroom featuring its own ensuite bath. White oak floors throughout. Downstairs a bedroom with a full bathroom has its own separate entrance and can be rented independently, offering plenty of opportunities. The driveway along the home provides off-street parking for up to 4 vehicles, a rare downtown convenience. Fenced in yard with plenty of room for a pool, tennis or basketball court, truly whatever your heart desires!Whether as a primary residence or investment property, this home is a standout opportunity in a PRIME location. Walking distance to Charleston Riverdogs Stadium, The Citadel, MUSC & easy access to all major highways. There are also shops and restaurants located within walking distance.

174 Fishburne Street, Charleston
435 Race Street, Charleston
$895,000
4 Beds ⋅ 2 Baths ⋅ 26022679 MLS ⋅ Westside SubDv. ⋅ Active Status
Beautifully updated duplex in the heart of downtown Charleston, offering flexible living options and exceptional convenience. This 1,631 sq ft property features two mirrored 2BR/1BA units on a 0.1-acre lot--ideal for an owner-occupant seeking rental income, a multi-generational living setup, or continued short-term, long-term and mid-term rental use.Each unit has been thoughtfully improved with smooth ceilings, tankless water heaters, updated plumbing lines, and an industrial-grade washer/dryer. The property also includes off-street parking for up to three vehicles, a fenced yard, and professional landscaping for easy maintenance.Located just steps from Hampton Park and minutes to King Street dining, Colonial Lake, MUSC, and Charleston's beaches, this home offers the perfect blendof comfort, versatility, and prime Westside location. A rare opportunity to own a well-maintained duplex in one of Charleston's most desirable downtown neighborhoods.

435 Race Street, Charleston
435 Race Street Unit #A & B, Charleston
$895,000
4 Beds ⋅ 26017619 MLS ⋅ Westside SubDv. ⋅ Active Status
Prime investment opportunity in downtown Charleston with active STR! This updated duplex offers 1,631 sq ft across two mirrored 2BR/1BA units on a 0.1-acre lot--ideal for long-term, mid-term, or owner-occupied STR potential. The duplex features off-street parking for up to 3 vehicles, a fenced yard, and professional landscaping. Recent improvements include smooth ceilings, tankless water heaters for each unit, new plumbing lines, and an industrial washer/dryer unit. Located steps from Hampton Park, and minutes to King Street dining, Colonial Lake, and area beaches. A rare chance to secure a high-demand rental property in the notable Westside neighborhood.Current insurance $5650/yr Current rolling 12-month income- $57,616.88

435 Race Street Unit #A & B, Charleston
695 King Street, Charleston
$1,499,000
5 Beds ⋅ 26015941 MLS ⋅ Westside SubDv. ⋅ Active Status
A classic Charleston Single style (currently in dual residence mode) in the coveted location of charming and historic King Street! This home was beautifully modernized with new trim, cabinetry, countertops, and lighting yet retains the character of original 100 year old heart pine floors and you will LOVE the look of the old brick fireplaces as centerpieces in many rooms. Lots of options to use as long term investment property with its proximity to CofC and The Citadel, convert back to a single family home, or have the BEST of BOTH WORLDS and live in one unit and rent the other. The upstairs unit has 3 bedrooms/2 baths, kitchen, living, and laundry machines located in the 1 car garage, and downstairs has 2 beds/1 bath, kitchen, living and laundry in bath. Unique fenced back yard space.

695 King Street, Charleston
695 King Street, Charleston
$1,499,000
5 Beds ⋅ 3 Baths ⋅ 26015937 MLS ⋅ Westside SubDv. ⋅ Active Status
Classic Charleston Single style (currently in dual residence AIRBNB mode coveted location of charming and historic King Street! This property was beautifully modernized with new trim, cabinetry, countertops, and lighting yet retains the character of original 100 year old heart pine floors and you will LOVE the look of the old brick fireplaces as centerpieces in many rooms. Lots of options to use as long term investment property with its proximity to Cof C and The Citadel, convert to a single family home, or have the BEST of BOTH WORLDS and live in one unit and rent the other. Upstairs unit has 3 bedrooms/2 baths, kitchen, living, downstairs has 2 beds/1 bath, kitchen, living and laundry in bath. Unique private artistic, fenced back yard & entertaining space

695 King Street, Charleston
227/229/3 Fishburne/Woodall Street, Charleston
$1,210,000
5 Beds ⋅ 3 Baths ⋅ 25009662 MLS ⋅ Westside SubDv. ⋅ Active Status
THREE Properties! Rare Downtown Opportunity - 227 Fishburne St, 229 Fishburne St, and 3 Woodall Court. An incredible opportunity to own multiple properties in the heart of downtown Charleston! 227 Fishburne Street, 229 Fishburne Street, and 3 Woodall Court are available for purchase individually or together, offering endless possibilities for renovation, expansion, or a spacious development project.227 Fishburne Street: A livable home ready for updates or renovation.229 Fishburne Street: A vacant lot currently used for parking, adjacent to 227.3 Woodall Court: A gutted home ready for a full renovation or new vision, located directly behind 227 Fishburne.Located just minutes from Hampton Park, The Citadel, MUSC, and some of Charleston's best restaurants, this location is ideal for creating a one-of-a-kind property. Whether you're an investor, developer, or looking for your next downtown project, don't miss out on this rare chance to secure a sizable footprint in one of Charleston's most sought-after areas! No survey or plat. The permit for the removal of the large Sycamore tree can be found in the documents.

227/229/3 Fishburne/Woodall Street, Charleston
227 & 229 Fishburne Street, Charleston
$835,000
3 Beds ⋅ 2 Baths ⋅ 25009654 MLS ⋅ Westside SubDv. ⋅ Active Status
227 and 229 Fishburne Street - Combined Opportunity!Two prime properties in downtown Charleston, sold together. 227 Fishburne Street is a livable home ready for updates or a full renovation, while 229 Fishburne Street is a vacant lot currently used as parking by the adjacent property. Purchase both to expand your downtown footprint or add on 3 Woodall Court, located directly behind 227, for even more space and potential. All properties are also available for sale individually. Walkable to restaurants, The Citadel, MUSC, and Hampton Park--this is an excellent opportunity to create a standout project in a sought-after location! No survey or plat.The permit for the removal of the large Sycamore tree can be found in the documents.

227 & 229 Fishburne Street, Charleston
3 Woodall Court, Charleston
$375,000
2 Beds ⋅ 1 Baths ⋅ 25009637 MLS ⋅ Westside SubDv. ⋅ Active Status
Opportunity awaits at 3 Woodall Court! This gutted home is ready for renovation or a fresh vision. Located within walking distance to restaurants, The Citadel, MUSC, and Hampton Park, the possibilities are endless. Purchase individually or combine with 227 and 229 Fishburne Street for a larger downtown project. Don't miss this incredible chance to create something special in the heart of Charleston! No off-street parking for this property. No survey or plat. Permit for the removal of the large Sycamore tree can be found in the documents.UPDATE 5/26/2026: WE HAVE HAD A LOT OF INTEREST AND OFFERS ON THESE PROPERTIES. AT THIS TIME, THERE IS STILL NO ETA ON PROBATE AND NO CHANGES TO REPORT. SELLER IS NOT LOOKING TO ACCEPT ANY OFFERS UNTIL PROBATE IS FINALIZED AND WOULD LIKE TO SELL ALL THREE LOTS TOGETHER. PLEASE CALL ME BEFORE SUBMITTING ANY OFFERS. Each property & lot are also listed separately: 25009637, 25009635, 25009636. OR 227 & 229 Fishburne together: 25009654. Please schedule showings through Showingtime. Appointment Only. ATTENTION: Before submitting an offer PLEASE refer to Presentation Of Offers in Documents. All information herein is furnished to the best of the Listing Agent's knowledge, but the Buyer and their Agent shall verify square feet, schools, HOA, age, acreage, zoning, insurance and all other information deemed important to buyer. Inquire with preferred lender for additional information on incentives to use towards an interest rate buy down or a closing cost credit. This property has not flooded.

3 Woodall Court, Charleston
227 Fishburne Street, Charleston
$585,000
3 Beds ⋅ 2 Baths ⋅ 25009635 MLS ⋅ Westside SubDv. ⋅ Active Status
Opportunity knocks at 227 Fishburne Street! This home is currently livable and ready for your updates, full renovation, or future vision. Ideally located within walking distance to restaurants, The Citadel, MUSC, and Hampton Park. Purchase 227 on its own, combine it with the adjacent empty lot at 229 Fishburne, or expand your possibilities even further by adding 3 Woodall Court, located directly behind 227. (ALL THREE MLS LISTING 25009662) (227 Fishbunre & 229 Fishburne 25009654). A rare chance to create a spacious downtown project in the heart of Charleston! Permit for the removal of the large Sycamore tree can be found in the documents.No survey or plat

227 Fishburne Street, Charleston
229 Fishburne Street, Charleston
$250,000
25009636 MLS ⋅ Westside SubDv. ⋅ Active Status
Rare opportunity to own a vacant lot in downtown Charleston! 229 Fishburne Street is currently being used for parking by the adjacent property at 227 Fishburne Street. This lot can be purchased individually, combined with 227 Fishburne to expand your footprint, or grouped with 3 Woodall Court as well to create a spacious multi-property project. Located within walking distance to restaurants, The Citadel, MUSC, and Hampton Park A-- this is a prime location for your next downtown investment! No survey or plat

229 Fishburne Street, Charleston