South Windermere Homes

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  /39

  $965,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,911 Sq Ft

  3 Lord Ashley Dr, Charleston, SC 29407

  Nestled in the heart of highly sought-after South Windermere, this classic 3 bedroom, 2 bathroom ranch-style home blends timeless charm with tasteful updates. Built in 1955, the home showcases a beautiful mix of preserved mid-century character and modern comforts.Freshly painted inside and out, the home welcomes you with curb appeal and a warm, inviting feel. Step inside to find spacious mudroom,

  Nina Freeman Beach Residential

  3 Lord Ashley Dr, Charleston, SC 29407
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  /29

  $2,300 per month

  • 3 Beds
  • 1.5 Baths
  • Condo for Rent

  639 Windermere Blvd Unit B, Charleston, SC 29407

  Property Id: 1216824Spacious three bedroom, one and a half bath home located in highly sought after South Windemere neighborhood. Walk to Earth Fare, coffee, yoga, massage, and several other shops and restaurants. Three minute drive to downtown Charleston and 20 minute drive to Folly Beach. Large fenced in backyard with patio. Washer/dryer in shed out back. Off street parking and street

  639 Windermere Blvd Unit B, Charleston, SC 29407
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  /22

  $565,000 Sold May 28, 2025

  • 1,720 Sq Ft
  • $328/SF
  • 6 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2006

  626 Windermere Blvd Unit 4D, Charleston, SC 29407

  Beautifully maintained and ideally located, this spacious townhouse on Windermere Blvd offers both comfort and convenience. Just minutes from South Windermere and the Earth Fare Shopping Center, Avondale, and only 5 minutes from historic Downtown Charleston, the location is truly unbeatable. Featuring 3 bedrooms and 3 full bathrooms, the open-concept layout seamlessly connects the kitchen,

  Michael Falotico The Boulevard Company

  626 Windermere Blvd Unit 4D, Charleston, SC 29407
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  /45

  Est $1,496,992 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,140 Sq Ft

  324 Confederate Cir, Charleston, SC 29407

  324 Confederate Cir, Charleston, SC 29407
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  /51

  $900,000

  • 3 Beds
  • 2 Baths
  • 2,003 Sq Ft

  22 Charlestowne Rd, Charleston, SC 29407

  Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of South Windermere, one of West Ashley's most desirable neighborhoods. A versatile bonus space, converted from the garage with its own exterior access, provides extra room for guests,a mother-in-law suite, playroom, studio, or den. This stylish residence offers seamless flow between the living room, dining area, and kitchen,

  Jonathan Holt Keller Williams Realty Charleston West Ashley

  22 Charlestowne Rd, Charleston, SC 29407
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  /29

  $839,000 Sold May 08, 2025

  • 1,831 Sq Ft
  • $458/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1953

  105 Chadwick Dr, Charleston, SC 29407

  Discover Your Dream Home in South Windermere - Move-In Ready Luxury Awaits!Nestled in the heart of Charleston's prestigious South Windermere neighborhood, this stunning brick ranch blends timeless charm with modern updates. Just 7 minutes from bustling downtown Charleston and 15 minutes from Folly Beach's sandy shores, this prime location offers the ultimate in convenience and lifestyle. Walk to

  John Bell The Boulevard Company

  105 Chadwick Dr, Charleston, SC 29407
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  /40

  Est $1,511,688 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,132 Sq Ft

  236 Confederate Cir, Charleston, SC 29407

  236 Confederate Cir, Charleston, SC 29407
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  /45

  $8,500,000

  • 4 Beds
  • 4.5 Baths
  • 3,950 Sq Ft

  27 Rebellion Rd, Charleston, SC 29407

  A rare and exquisite opportunity to create your dream coastal retreat on one of the most coveted deepwater lots in the Charleston area. Perfectly positioned on the tranquil banks of Coburg Creek, this premier homesite offers panoramic marsh views, breathtaking sunsets, and unparalleled access to true deep water--with over 8 feet at the end of the newly constructed dock.This expansive, cleared and

  Ruthie Ravenel Daniel Ravenel Sotheby's International Realty

  27 Rebellion Rd, Charleston, SC 29407
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  /32

  $359,900 Sold Apr 30, 2025

  • 1,020 Sq Ft
  • $353/SF
  • 29 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1987

  270 Stefan Dr Unit 11D, Charleston, SC 29412

  Welcome to your beautifully updated townhouse nestled in one of the most desirable areas of James Island. You'll find this home offers the ideal blend of modern style & comfort as well as everyday convenience. This 2 Bed / 1.5 bath townhouse has been thoughtfully updated throughout, including sleek LVP flooring on the main floor, modern light fixtures, smoothed ceilings, updated kitchen cabinets

  Atlas Fathalla EXP Realty LLC

  270 Stefan Dr Unit 11D, Charleston, SC 29412
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  /28

  Est $953,056 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,105 Sq Ft

  367 Confederate Cir, Charleston, SC 29407

  367 Confederate Cir, Charleston, SC 29407
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  /33

  $2,250,000

  • 4 Beds
  • 2.5 Baths
  • 3,480 Sq Ft

  28 Rebellion Rd, Charleston, SC 29407

  Welcome to 28 Rebellion Rd, a stunning home in the desirable South Windermere neighborhood. This Lowcountry gem offers breathtaking marsh and river views and an unparalleled Charleston lifestyle. With a brand-new roof installed this year, and new trex porches, this 4-bedroom, 2.5-bathroom home boasts a classic design with plenty of space and character. Inside, you'll find gleaming hardwood

  Robertson Allen The Cassina Group

  28 Rebellion Rd, Charleston, SC 29407
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  /46

  $3,850,000 Sold Mar 05, 2025

  • 3,700 Sq Ft
  • $1041/SF
  • 2 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1955

  92 Chadwick Dr, Charleston, SC 29407

  TRUE DEEP WATER just minutes from downtown Charleston! Live in the prestigious South Windermere neighborhood, where this fully renovated mid-century modern ranch-style home offers a unique chance to experience waterfront living at its finest. Enjoy deepwater access with panoramic views of Wappoo Creek and Elliott Cut, all on nearly half an acre of prime waterfront property. Originally built in

  Josh Broome The Cassina Group

  92 Chadwick Dr, Charleston, SC 29407
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  /61

  Est $1,420,376 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,584 Sq Ft

  363 Confederate Cir, Charleston, SC 29407

  363 Confederate Cir, Charleston, SC 29407
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  /17

  $799,500 Pending

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft

  148 Chadwick Dr, Charleston, SC 29407

  Live in the center of everything. This 3BR/2BA brick ranch is conveniently located in South Windermere. Minutes from downtown. Easy walking distance to shopping, elementary school, daycare, library, and restaurants. Just three blocks from the West Ashley Greenway and half a mile from the Wappoo Cut Boat Landing. Established live oaks and fruit trees add to the natural beauty of the corner

  David Fralix Harrison Creek Enterprises Inc

  148 Chadwick Dr, Charleston, SC 29407
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  /34

  $1,800,000 Sold Feb 03, 2025

  • 3,604 Sq Ft
  • $499/SF
  • 4 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1953

  63 Chadwick Dr, Charleston, SC 29407

  Welcome 63 Chadwick Dr, in the highly coveted neighborhood of South Windermere, less than 10 minutes to downtown and just 20 minutes to Folly Beach. This beautifully renovated and meticulously maintained 5-bedroom, 3.5-bathroom home was perfectly designed for both functionality and elegance, and offers a versatile floor plan ideal for any lifestyle. On the main level, you'll find a light and

  Valerie Weber The Boulevard Company

  63 Chadwick Dr, Charleston, SC 29407
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  /34

  Est $1,934,708 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,078 Sq Ft

  65 Rebellion Rd, Charleston, SC 29407

  65 Rebellion Rd, Charleston, SC 29407
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  /92

  $895,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,362 Sq Ft

  46 Chadwick Dr, Charleston, SC 29407

  Welcome to 46 Chadwick, a charming split-level home, nestled in the highly desirable South Windermere neighborhood, located only 5 minutes from downtown Charleston. This lovely 4-bedroom, 3.5-bathroom home offers a spacious floor plan that is ideal for both everyday living and entertaining.This lovely home welcomes you with a large front porch and a nicely sized foyer adorned with wood floors.

  Raina Rubin Carolina One Real Estate

  46 Chadwick Dr, Charleston, SC 29407
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  /21

  $660,000 Sold Dec 30, 2024

  • 1,610 Sq Ft
  • $410/SF
  • 12 Days On Market

  • 4 Beds
  • Built 1955

  631 Windermere Blvd, Charleston, SC 29407

  LOCATION! LOCATION! lOCATION! Rare opportunity to own an investment duplex in the coveted South Windermere subdivision. 2BR/1BA each side. 2006 - Central Air was added to the entire place - it was only heat. So duct work and condenser/evaporator added to both sides. New roof added 2016. Dishwashers added to both sides and Washer/Dryer connections moved to out buildings in back both sides. A lot

  Jenny Daly JPAR Magnolia Group

  631 Windermere Blvd, Charleston, SC 29407
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  /45

  Est $558,123 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,576 Sq Ft

  635 Windermere Blvd Unit 2A, Charleston, SC 29407

  635 Windermere Blvd Unit 2A, Charleston, SC 29407
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  /50

  $559,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 1,720 Sq Ft

  622 Windermere Blvd Unit D, Charleston, SC 29407

  Beautifully Maintained End Unit in Prime Windermere Location - 1,720 Sq Ft! This spacious 3-bed, 3-bath townhouse offers unbeatable convenience--just steps from South Windermere shops and restaurants, the West Ashley Greenway, and minutes to Avondale, Downtown Charleston, and Folly Beach. With 1,720 square feet of living space, the open-concept layout features hardwood floors, stainless steel

  Cade Brummett Realty One Group Coastal

  622 Windermere Blvd Unit D, Charleston, SC 29407
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  /24

  $970,000 Sold Dec 20, 2024

  • 1,900 Sq Ft
  • $511/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  8 Charlestowne Rd, Charleston, SC 29407

  Welcome to your dream home nestled in the picturesque neighborhood of South Windermere! This delightful ranch-style residence is close proximity to historic downtown Charleston and beautiful beaches, offering the best of both worlds! As you approach this charming home, you'll be greeted by its curb appeal, featuring a well-maintained landscape and a welcoming front porch. Step inside to discover

  Caroline Perkins The Cassina Group

  8 Charlestowne Rd, Charleston, SC 29407
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  /9

  Est $553,830 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,576 Sq Ft

  619 Windermere Blvd Unit 1B, Charleston, SC 29407

  619 Windermere Blvd Unit 1B, Charleston, SC 29407
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  /30

  $885,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  13 Charlestowne Rd, Charleston, SC 29407

  An all access lifestyle awaits at this classic South Windermere home. The location is unbeatable. You'll literally walk to shops, restaurants, the West Ashley Greenway and the highly rated St Andrews Elementary School of Math and Science. The floorplan truly 'lives larger' than the square footage with a generous kitchen that opens to both the dining room and sunroom/flex space that offers many

  Ed Boudolf Carolina One Real Estate

  13 Charlestowne Rd, Charleston, SC 29407
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  /73

  $1,205,000 Sold Dec 11, 2024

  • 2,471 Sq Ft
  • $488/SF
  • 21 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1955

  69 Chadwick Dr, Charleston, SC 29407

  This stunning four bedroom, two and half bath home in the highly sought after Windermere neighborhood offers the perfect blend of classic charm and modern luxury. The home has been fully renovated with impeccable attention to detail. The spacious primary bedroom is conveniently located on the main floor, providing privacy and comfort, and features an en-suite bathroom with marble tile and large

  Anna Gruenloh The Exchange Company, LLC

  69 Chadwick Dr, Charleston, SC 29407
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  /43

  Est $804,828 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft

  26 Charlestowne Rd, Charleston, SC 29407

  26 Charlestowne Rd, Charleston, SC 29407
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  /137

  $5,850,000 Under Contract

  • 4 Beds
  • 4.5 Baths
  • 4,667 Sq Ft

  333 Confederate Cir, Charleston, SC 29407

  If you are looking for the ultimate in a bespoke living experience, with every surface carefully curated and exquisitely designed, this incredibly sophisticated home is for you.This 1962 mid-century modern house exudes quiet luxury and was completely transformed in 2022, uniting impeccable craftsmanship with the finest finishes fused with functional design. This spectacular home sits on a scenic

  Leslie Turner Maison Real Estate

  333 Confederate Cir, Charleston, SC 29407
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  /51

  $1,065,000 Sold Oct 24, 2024

  • 2,581 Sq Ft
  • $413/SF
  • 21 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1955

  36 Tarleton Dr, Charleston, SC 29407

  Located in one of Charleston's most popular neighborhoods, this beautifully appointed 4 bedroom, 2.5 bath home is waiting for you. The open living area with gleaming wood floors has plenty of space for entertaining. The living room with wood burning fireplace has a lovely 200 year old re-claimed, redwood, mantle. The spacious dining room opens to the gourmet kitchen and lovely sunroom with

  Becky Johnston The Boulevard Company

  36 Tarleton Dr, Charleston, SC 29407
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  /32

  Est $1,080,709 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,765 Sq Ft

  10 Charlestowne Rd, Charleston, SC 29407

  10 Charlestowne Rd, Charleston, SC 29407
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  /23

  $367,000 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft

  270 Stefan Dr Unit 11C, Charleston, SC 29412

  Welcome to 270 Stefan Drive unit 11C, a charming two-story townhouse on James Island, featuring a private gated backyard with brick-lined tabby shell hardscaping. The renovated kitchen opens nicely to the dining and living space, and the convenient layout includes a half bath on the first floor and an updated full bath upstairs. The main living area features durable ceramic tile floors that

  Beverly Burris William Means Real Estate, LLC

  270 Stefan Dr Unit 11C, Charleston, SC 29412
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  /65

  $1,850,000 Sold Aug 26, 2024

  • 3,264 Sq Ft
  • $567/SF
  • 0 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 1986

  37 Rebellion Rd, Charleston, SC 29407

  Welcome to 37 Rebellion Road, a contemporary marsh front oasis! Nestled in the established and desirable South Windermere neighborhood, this elevated gem offers a harmonious blend of modern design and natural beauty. Let's explore the highlights: ~Beautifully Landscaped: The lush greenery surrounding the property sets the stage for tranquility and serenity. ~Elevated Elegance: Step onto the

  Raina Rubin Carolina One Real Estate

  37 Rebellion Rd, Charleston, SC 29407
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  /54

  Est $1,083,041 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,368 Sq Ft

  6 Charlestowne Rd, Charleston, SC 29407

  6 Charlestowne Rd, Charleston, SC 29407
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  /10

  $1,500,000 Sold Aug 19, 2024

  • 3,749 Sq Ft
  • $400/SF
  • 21 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1961

  258 Confederate Cir, Charleston, SC 29407

  A Charleston traditional, one family owned home for over 60 years, on most desirable Confederate Circle, in the well established and sought after South Windermere. This home features five bedrooms, four full bathrooms and one half bathroom. A spacious foyer welcomes you to this most unique home. The living room is to the right and has a fireplace. The formal dining room, with a very large window

  Eve Sokol Elaine Brabham and Associates

  258 Confederate Cir, Charleston, SC 29407
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  /33

  Est $946,871 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,973 Sq Ft

  7 Charlestowne Rd, Charleston, SC 29407

  7 Charlestowne Rd, Charleston, SC 29407
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  /49

  $985,000 Sold Aug 01, 2024

  • 1,566 Sq Ft
  • $629/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1954

  18 Lord Ashley Dr, Charleston, SC 29407

  Welcome to 18 Lord Ashley Drive, located in the esteemed South Windermere neighborhood, offering the rare advantage of no HOA restrictions. This beautifully updated ranch home presents a harmonious blend of three bedrooms, two full bathrooms, and a seamless fusion of comfort and panache. Main home features 1566 square feet and detached home features garage and an additional 588 square feet of

  Jason Brown The Boulevard Company

  18 Lord Ashley Dr, Charleston, SC 29407
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  /64

  Est $1,012,009 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft

  18 Sheridan Rd, Charleston, SC 29407

  18 Sheridan Rd, Charleston, SC 29407
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  /27

  $965,000 Sold Jun 29, 2024

  • 2,032 Sq Ft
  • $475/SF
  • 86 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1959

  134 Chadwick Dr, Charleston, SC 29407

  Charming 4 bedroom 2 bath brick ranch on tidal creek with dock, located in one of Charleston's most beloved neighborhoods and only 2 traffic lights to historic downtown Charleston! Brand new metal roof in 2023. Large secluded back yard updated with huge new wooden deck and newly framed dock. Wood floors found throughout most of the living areas, spacious kitchen with granite counters. Additional

  Ian O'shea A House in the South Realty

  134 Chadwick Dr, Charleston, SC 29407
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  /36

  Est $1,127,569 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,137 Sq Ft

  118 Chadwick Dr, Charleston, SC 29407

  118 Chadwick Dr, Charleston, SC 29407
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  /44

  $1,955,000 Sold Jun 14, 2024

  • 3,807 Sq Ft
  • $514/SF
  • 5 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1967

  351 Confederate Cir, Charleston, SC 29407

  This Just May Be Your Dream Home... Step inside the double front doors to an expansive living space. On one side is an airy and open living room with a gas fireplace and built-in shelving; on the other a dining area and state-of-the-art kitchen, equipped with Thermador appliances and breakfast bar. There are gorgeous hardwood floors throughout. Glass all across the far wall opens to a

  Margaret Von Werssowetz Handsome Properties, Inc.

  351 Confederate Cir, Charleston, SC 29407
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  /29

  Est $920,786 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,160 Sq Ft

  1 Lord Ashley Dr, Charleston, SC 29407

  1 Lord Ashley Dr, Charleston, SC 29407
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  /59

  $950,000 Sold Jun 07, 2024

  • 1,800 Sq Ft
  • $528/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1955

  11 Jamaica Dr, Charleston, SC 29407

  Embrace this incredible opportunity to own in one of Charleston's most coveted neighborhoods of South Windermere. The current owners' love for this one-story home is evident in every detail and design element throughout the property. The skillfully planned renovations remain true to the character of the home by marrying historical elements and classic charm with modern updates. It is the perfect

  Laura Frawley The Boulevard Company

  11 Jamaica Dr, Charleston, SC 29407

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