55 Bay Street, Charleston, SC 29401 MLS #25024554 Home Real Estate Charleston Charleston 29401 55 Bay Street Share Ask Realtor Saving Save Saved55 Bay Street | #25024554 Under Contract - $8,995,000Charleston, SC 29401 55 Bay Street | #25024554 Under Contract - $8,995,000 Share Ask Realtor Saving Save Saved MLS ID: 25024554 Under Contract - $8,995,000 About this property Bedrooms 5 Baths 5 Half Baths 1 sq2 7343 Lot Size 0.1900 acres Year Built 1785 DOM 102AddressAddress:55 Bay StreetSubdivision: South of BroadCity: CharlestonZip Code: 29401County: CharlestonState: SCFeatures and AmenitiesExterior Lawn IrrigationCooling Central AirLaundry Features Laundry RoomInterior Features Ceiling - Cathedral/Vaulted, High Ceilings, Garden Tub/Shower, Walk-In Closet(s), Eat-in Kitchen, Family, Formal Living, Office, Pantry, Separate DiningUtilities Charleston Water Service, Dominion EnergyFireplace Features Three +Window Features Window TreatmentsLot Features 0 - .5 AcreStyle Charleston SingleOther Slate, Garden Tub/Shower, Multiple Closets, Walk-In Closet(s) Show all features Description This stunning c. 1785 four-story masonry home has been carefully preserved, exhibiting significant historical integrity. It has undergone an extensive renovation, elegantly updated to accommodate modern living and entertaining. Book-ended by Rainbow Row and High Battery, the Jonathan Simpson House was built within the original walled city by a wealthy merchant. Twelve-foot ceilings and grand rooms allow the house to be filled with light. The pine floors run the full extent of the house (28'). Much of the original molding, cypress paneling, doors, and interior shutters remain. The current owners created a hyphen to connect the original home and kitchen house under the direction of renowned Charleston architects Dufford Young, with construction by Artis, winning a 2019 Carolopolis Award.The project allowed for a new side garden design by Sheila Wertimer. The gourmet kitchen features a butler's pantry, mudroom, and floor-to-ceiling steel doors overlooking the side garden. The former kitchen house now features a spacious second-floor guest suite or office and a large secondary living room flanked by original fireplaces, as well as access to the screened porch overlooking the magnificent backyard that encompasses nearly a quarter of an acre of peace and tranquility. Plans were created for a 10' x 30' swimming pool and have been approved by the city. The existing custom-built "shed" could be easily converted to a pool house with bathroom.The original staircase remains, rising eloquently for all four flights, one of the tallest in the city. The second floor of the home has a 21x25 drawing room with five floor-to-ceiling windows. Across the hall, a primary suite with a fireplace and a private porch overlooking historic rooftops and palmetto trees. The third floor includes two spacious bedrooms, both with en-suite bathrooms, as well as a laundry room. The front bedroom offers clear views of Charleston Harbor. The back bedroom offers a private porch that's perched in the palmetto trees. The fourth floor is laid out as a two-room guest suite with a full bathroom and a living room, incredible historic and water views from every window.Of significant architectural interest is the cantilevered marble balcony, which projects from the second floor and is the only one in Charleston constructed in this manner. The elliptical fan light and the use of tall, glazed windows typify the work of the Adam period. Also of notable distinction is the detailed woodwork and roping around the door frame, which makes this one of the more attractive entrances in historic Charleston. The home retains architectural features of the late Georgian period, also embracing the ornamentation that more closely resembles the Adam style or the Federal period of architectural development.Schools 3-8 SPED PK-5 SPED K-8 Name Address Phone Type Grade Buist Academy 103 Calhoun Street 8437247750 Public 3-8 SPED Name Address Phone Type Grade Memminger Elementary 20 Beaufain Street 8437247778 Public PK-5 SPED Name Address Phone Type Grade Charleston Day School 15 Archdale Street 843-377-0315 Private K-8 Mason Preparatory School 56 Halsey Blvd. 843-723-0664 Private K-8 All Neighborhoods in Charleston ABCDEFGHIJKLMNOPQRSTUVWXYZ2 subdivision Active Listings Avg Days on Market Avg DoM Avg Price A ABCDEFGHIJKLMNOPQRSTUVWXYZ2 air harbor , Charleston 2235$511,987 ansonborough , Charleston 17251$2,514,056 arboretum , Charleston 1202$310,992 archdale , Charleston 2323$513,086 ardmore , Charleston 6202$396,977 ashcroft hall , Charleston 197$707,450 asheford place at canterbury woods , Charleston 1220$452,250 ashley forest , Charleston 2310$713,790 ashley hall manor , Charleston 3207$569,461 ashley hall plantation , Charleston 1236$592,800 ashley house , Charleston 6204$342,742 ashley park , Charleston 6212$392,217 ashley walk townes , Charleston 474$465,867 ashleytowne village , Charleston 4262$245,952 ashleyville , Charleston 3118$492,414 autumn chase , Charleston 157$575,000 avenue of oaks , Charleston 2151$1,064,975 avondale , Charleston 3259$873,161 B baker plantation , Charleston 1283$411,967 battery gaillard , Charleston 1249$695,301 battery haig on the stono , Charleston 3189$734,714 battery island , Charleston 120$2,250,000 battery point , Charleston 3167$619,675 bayfield manor , Charleston 1165$804,975 bayfront , Charleston 1306$750,200 beauregard house , Charleston 1438$677,000 bee street condominiums , Charleston 1146$459,000 bee street lofts , Charleston 6273$602,875 bel air , Charleston 2251$594,667 bennetts bluff , Charleston 1371$1,247,724 beresford commerce park , Charleston 2172$920,000 beresford commons , Charleston 2258$363,580 beresford creek landing , Charleston 4318$1,658,950 beresford hall , Charleston 3303$2,734,347 berkeley court , Charleston 1103$559,000 bermuda pointe towns , Charleston 4330$326,689 bolton , Charleston 1346$386,950 boltons landing , Charleston 8213$528,229 brigadier condominium , Charleston 2179$248,317 bull creek peninsula , Charleston 1131$1,900,000 byrnes downs , Charleston 8188$825,666 C camp road estates , Charleston 1195$1,048,333 cannonborough , Charleston 1264$1,422,000 cannonborough-elliotborough , Charleston 39339$1,840,327 canterbury woods , Charleston 2211$452,531 capri isles , Charleston 1367$1,274,661 carolina bay , Charleston 19227$599,143 carolina cove , Charleston 8127$260,215 castlewood , Charleston 3168$363,971 center park , Charleston 2131$1,141,667 centerville , Charleston 3114$587,621 central park , Charleston 10230$1,040,178 charlestowne est , Charleston 3229$672,664 charlestowne estates iii , Charleston 1277$578,333 cherokee hall , Charleston 3172$296,225 church creek , Charleston 2245$407,991 church creek landing , Charleston 2102$587,333 citadel woods , Charleston 3176$466,333 city of charleston , Charleston 23410$1,826,566 clarks point , Charleston 3132$1,052,714 clarks sound , Charleston 2321$527,000 clearview , Charleston 2153$895,818 cochran park , Charleston 1228$1,449,500 cocked hat point , Charleston 148$824,900 concord west of the ashley , Charleston 5259$348,213 country club ii , Charleston 3131$2,197,500 creek point , Charleston 5171$556,227 creekside , Charleston 288$1,550,000 croghan landing , Charleston 2253$1,058,167 D daniel island , Charleston 38229$1,855,650 daniel island park , Charleston 13263$3,711,460 daniel island smythe park , Charleston 3263$1,997,952 daniels landing , Charleston 3213$406,994 dockside , Charleston 8217$306,524 dogwood commons , Charleston 1279$526,000 dogwood park , Charleston 1161$1,030,000 dorchester terrace , Charleston 1133$258,000 douglas jones , Charleston 1226$830,000 dovefield , Charleston 3213$221,217 downtown , Charleston 7239$1,525,434 drayton on the ashley , Charleston 4201$605,699 dupont , Charleston 197$255,000 E e f street , Charleston 1233$594,000 east oak forest , Charleston 2260$663,800 east oak forest ext , Charleston 3297$509,975 eastside , Charleston 22228$1,022,452 eastwood , Charleston 5135$1,431,809 edgewater park , Charleston 2158$1,494,800 edgewood gardens , Charleston 1203$508,725 elliotborough , Charleston 8224$1,376,880 essex village , Charleston 1195$603,000 F fairfield , Charleston 118$473,000 fairfield pines , Charleston 1227$586,000 fairfield plantation , Charleston 149$395,000 fairway villas , Charleston 1243$481,667 forest acres , Charleston 3203$512,450 forest lakes , Charleston 2202$528,867 forest lakes extension , Charleston 1166$513,490 fort johnson estates , Charleston 4226$1,164,090 fort lamar , Charleston 2233$919,856 french quarter , Charleston 9311$2,193,160 G gadsdenboro , Charleston 3249$1,081,007 garden hill , Charleston 2150$926,333 geddes hall , Charleston 2237$621,733 general lee , Charleston 1331$444,333 george and society , Charleston 4142$1,231,050 goat island , Charleston 1167$299,000 governors cay , Charleston 8223$675,151 grand bees , Charleston 8231$530,965 grand oaks plantation , Charleston 18219$455,940 grand terrace , Charleston 3224$478,571 grants court , Charleston 9128$1,016,101 greencrest , Charleston 2312$537,500 H hampton park , Charleston 164$1,025,000 hampton park terrace , Charleston 5215$2,043,083 harbor creek , Charleston 2189$626,750 harbor place , Charleston 1188$617,475 harbor view , Charleston 121$995,000 harbor woods , Charleston 1240$776,250 harborwalk , Charleston 1105$587,500 harleston green , Charleston 113$1,350,000 harleston village , Charleston 39252$2,099,882 harrison acres , Charleston 1291$799,667 heathwood , Charleston 1241$547,615 hickory farms , Charleston 1250$989,000 hickory hill plantation , Charleston 6177$580,082 hoff gardens , Charleston 3153$556,600 hunt club , Charleston 10163$620,944 hunt club phase ii , Charleston 1292$562,975 huntington woods , Charleston 2192$1,104,100 I inland court , Charleston 1240$294,500 island bluff , Charleston 1183$332,483 isle de nemours , Charleston 2254$1,200,000 J jackson heights , Charleston 1233$433,300 james island , Charleston 6253$641,476 jamestown estates , Charleston 2266$538,560 jamestowne village , Charleston 1192$588,000 K kings flats , Charleston 1181$847,000 kingsland , Charleston 144$435,000 L lake shore commons , Charleston 2147$671,250 lakeshore commons , Charleston 1136$779,500 lakeside , Charleston 1246$409,656 landings at sweetwater , Charleston 9301$851,255 landsdowne , Charleston 179$496,667 lantana , Charleston 2243$479,975 laurel oak , Charleston 1289$566,200 laurel park , Charleston 3216$756,117 lawton bluff , Charleston 8280$750,369 lawton harbor , Charleston 1168$665,857 lebby , Charleston 133$937,500 legares , Charleston 11,526$1,093,500 lenevar , Charleston 2186$614,142 lighthouse point , Charleston 4222$788,646 long branch on the creek , Charleston 449$518,800 longborough , Charleston 4145$2,175,250 longbranch , Charleston 1201$521,150 lynwood , Charleston 2275$581,667 M maclaura hall , Charleston 2310$827,250 magnolia , Charleston 2185$608,860 magnolia bluff , Charleston 2212$559,857 magnolia ranch , Charleston 3175$513,737 martins creek , Charleston 1229$1,074,667 maryville , Charleston 10164$408,845 mayflower ct , Charleston 2178$544,250 mccalls corner , Charleston 5184$617,823 mcintyre , Charleston 3119$454,500 mclaura bluff , Charleston 1192$615,580 melrose , Charleston 6200$550,347 melrose extension , Charleston 1148$433,300 melrose park townhomes , Charleston 4217$169,888 memminger hall , Charleston 1269$473,125 mepkin place , Charleston 7223$207,844 meridian place , Charleston 7249$398,439 middleton oaks , Charleston 267$1,174,500 middleton place , Charleston 3222$244,667 mira vista , Charleston 6188$380,072 moreland , Charleston 4168$1,018,909 myrtle grove , Charleston 1299$439,925 N nelliefield plantation , Charleston 1238$586,180 north central , Charleston 23238$871,222 north pine point , Charleston 1175$857,450 northbridge terrace , Charleston 1236$751,687 not within a subdivision , Charleston 1246$965,000 O oak bluff , Charleston 1541$741,215 oak island , Charleston 1216$1,426,000 oak view park , Charleston 1300$237,500 oakcrest , Charleston 1314$597,778 ocean neighbors , Charleston 5220$725,150 old towne acres , Charleston 1271$632,500 old towne villas , Charleston 5120$315,650 one cool blow , Charleston 3179$399,350 one vendue range , Charleston 5140$2,559,143 orange grove , Charleston 3361$507,667 orange grove estates , Charleston 11216$481,000 orange grove shores , Charleston 1174$433,333 orleans woods , Charleston 2314$334,200 other , Charleston 121$329,900 otranto club villas , Charleston 1226$260,000 P palm pointe condominiums , Charleston 1148$424,333 palmetto pointe , Charleston 2288$1,005,633 palmettos at folly , Charleston 116$379,500 park place , Charleston 1261$477,400 parkdale , Charleston 1304$296,633 parkside hpr , Charleston 2226$514,914 parkwood estates , Charleston 4165$636,817 parsonage point , Charleston 5247$287,308 patriots plantation , Charleston 240$844,950 pecan grove , Charleston 2197$502,483 pelican cove , Charleston 2173$323,980 pelican pointe villas , Charleston 4236$402,900 peninsula , Charleston 1251$241,633 pepperidge , Charleston 1173$314,613 perreyclear pointe , Charleston 3144$273,260 pier view , Charleston 3181$705,690 pierpont , Charleston 9289$713,852 pinecrest gardens , Charleston 4182$530,271 pinefield , Charleston 1854$989,800 point hope , Charleston 28235$927,475 point james , Charleston 10136$264,038 ponderosa , Charleston 2211$352,758 providence commons , Charleston 1234$540,286 Q queensborough , Charleston 3240$543,317 R radcliffe place , Charleston 4183$313,744 radcliffeborough , Charleston 9265$1,672,001 regatta on james island , Charleston 4243$316,694 rice hollow , Charleston 291$684,450 river bend , Charleston 144$1,015,000 river reach pointe , Charleston 2200$956,300 riverbend , Charleston 4165$1,044,440 riverfront , Charleston 4187$614,764 riverland crossing , Charleston 2251$574,500 riverland park , Charleston 2150$786,100 riverland place , Charleston 2215$469,363 riverland terrace , Charleston 8219$1,402,303 rivers bend , Charleston 3218$243,940 rivers point , Charleston 3175$669,111 rivers point row , Charleston 6195$266,671 rosemont , Charleston 3208$178,167 rotherwood estates , Charleston 1227$648,422 royal , Charleston 3289$444,725 S sable on the marsh , Charleston 2312$632,000 savage , Charleston 1173$347,833 schieveling plantation , Charleston 2234$642,500 seagate , Charleston 3277$333,833 seagate condos , Charleston 143$275,000 seagate village , Charleston 2310$338,650 seaside estates , Charleston 2131$1,358,150 seaside plantation , Charleston 10208$837,913 secessionville , Charleston 2403$801,000 secessionville acres , Charleston 14$1,050,000 shadowmoss , Charleston 25243$521,763 shaftesbury , Charleston 3185$389,500 shellring at st thomas island , Charleston 2185$889,816 sherwood forest , Charleston 2241$366,223 sol legare , Charleston 3240$323,500 south of broad , Charleston 41237$3,565,554 south riverview , Charleston 1335$689,250 south windermere , Charleston 6222$1,741,329 springfield , Charleston 8209$401,466 st thomas point , Array 2188$969,483 st thomas preserve , Array 4200$971,127 st. thomas island , Charleston 2399$692,500 stiles point , Charleston 2210$707,583 stiles point plantation , Charleston 2176$1,720,556 stone creek , Charleston 2223$707,160 stoneboro shores , Charleston 1125$815,000 stonefield , Charleston 2160$698,233 stono terrace , Charleston 2288$703,750 stratton capers , Charleston 1184$150,000 sunday hill , Charleston 184$587,000 sylvan shores , Charleston 1322$633,243 T teal acres , Charleston 1183$484,500 terrabrook , Charleston 1216$854,124 the bluffs at pinefield , Charleston 12245$576,022 the colony at heron reserve , Charleston 4221$298,185 the cove at folly , Charleston 229$1,285,000 the crescent , Charleston 3275$4,580,809 the harborage at ashley marina , Charleston 7265$157,480 the marshes at cooper river , Charleston 5238$532,231 the marshes at daniel island , Charleston 380$2,411,667 the palmettos at folly , Charleston 260$392,500 the peninsula , Charleston 8234$466,598 the peninsula condominiums , Charleston 9226$268,491 the pointe at rhodes crossing , Charleston 3218$585,283 the ponderosa , Charleston 1254$388,088 the preserve at the clam farm , Charleston 211$962,500 the retreat at riverland , Charleston 3296$411,681 the riverside , Charleston 114$1,150,000 the savannah , Charleston 2175$208,317 the settlement , Charleston 3463$1,202,157 the slips at ripley , Charleston 2290$113,300 the village at stiles point , Charleston 2232$1,234,833 the villas of west ashley , Charleston 1142$420,000 the willows , Charleston 163$451,750 turkey pen , Charleston 13,366$250,000 twin rivers towns , Charleston 129$415,000 U university place , Charleston 4333$315,667 uptown , Charleston 1691$1,000,000 V vanderhorst , Charleston 3106$1,175,000 vendue range , Charleston 258$2,179,500 verdier pointe , Charleston 32362$482,152 village green , Charleston 7209$495,202 villas of west ashley , Charleston 2103$419,000 W wagener terrace , Charleston 15234$1,153,104 wando point , Charleston 1112$912,498 wando village , Charleston 6309$1,547,239 wappoo heights , Charleston 2207$1,468,800 wappoo shores , Charleston 1271$898,414 waterway south , Charleston 3127$431,650 wespanee place , Charleston 190$700,000 wespanee plantation , Charleston 2240$1,265,714 west ashley plantation , Charleston 6216$583,903 west oak forest , Charleston 3221$586,400 west oak forest ext , Charleston 1201$581,333 westborough , Charleston 4172$484,108 westchester , Charleston 4206$488,663 westside , Charleston 17248$960,051 wexford sound , Charleston 2227$758,536 white point estates , Charleston 1312$2,272,500 whitehall , Charleston 2169$486,083 whitehouse plantation , Charleston 5163$637,700 wildwood , Charleston 1173$227,000 wildwood town homes , Charleston 4144$262,914 willow bend , Charleston 114$300,000 willow oaks , Charleston 1257$313,725 willow walk , Charleston 3214$525,855 windsor hill , Charleston 1274$314,633 woodland shores , Charleston 5213$968,618 woodlands , Charleston 5267$465,215 wraggborough , Charleston 4211$1,991,700 Y yellow house place , Charleston 2210$970,000 2 200 river landing dr , Charleston 3196$698,343 254 seven farms drive , Charleston 5231$388,153 Price Change history $9,375,000 $1,277/SqFt 07, Sep. 2025 $8,995,000 $1,225/SqFt 14, Nov. 2025 Mortgage Calculator Price: $ Down Payment: $ % Term(*in years): Interest Rate in %: % Interest Rate as of: Thu, Dec. 18, 2025 $8,995,000Home Price $8,995,000Monthly payment $8,995,000Amount Financed $8,995,000Annual cost of Loan Get Approved Map SEE THIS PROPERTY James Schiller Realtor, Brand Name Real Estate Email: jameseschiller@gmail.com Live Chat: Reviews Your Email: Your Name: Phone: Subject: I WANT TO VIEW THIS PROPERTYI'D LIKE TO MAKE AN OFFERWHAT ARE THE FEES?ASK A QUESTION Message: Send Similar Listings Previus Next ©2025 CTMLS, GGMLS, CCMLS & CMLSThe information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS boards of the SC Realtors. Listing Provided by The Boulevard Company 55 Bay Street, Charleston, SC, 29401 MLS: #25024554 $8,995,000 Share Contact Realtor Saving Save Saved