Southside Homes for Sale

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  $2,000,000

  • Land
  • 20,037 Sq Ft
  • $4,347,826 per Acre

  1759 Cherokee Dr, Sarasota, FL 34239

  An exceptional 100X200 lot in historic Cherokee Park awaits your dream home, with Fergeson Brothers design/construction as the designatedbuilder; this west-of-the-trail neighborhood is located on Sarasota Bay in the City of Sarasota; The adjoining lot MLS A4686830 is also for sale.

  Rogers Moore COLDWELL BANKER REALTY

  1759 Cherokee Dr, Sarasota, FL 34239
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  $1,099,900

  $350K PRICE DROP

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

  1958 Morris St, Sarasota, FL 34239

  Virtually Staged. Now offering buyer incentives and priced below appraised value! This exceptional single-family pool home offers the perfect blend of space, flexibility, and prime Sarasota location. Featuring 4 bedrooms and 3 full bathrooms, this residence is thoughtfully designed to accommodate a variety of living arrangements, including two primary suites, each with its own en suite

  Jon Patella WAGNER REALTY

  1958 Morris St, Sarasota, FL 34239
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  /24

  $275,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 976 Sq Ft

  3711 Almeria Ave Unit 3-N, Sarasota, FL 34239

  Discover this hidden gem 1st floor 2 BR, 2BA condo in Sarasota’s historic Granada neighborhood along Siesta Drive. Walkable to Red Rock Park, Publix, Southside Elem. Easily accessible to Sarasota Memorial Hospital and the restaurants, shops and entertainment of Southside Village and the nearby national award winning Siesta Key Beach, Marie Selby Botanical Gardens and The Bay. Enjoy southwest

  Anita McGillin WEICHERT REALTORS HALLMARK PRO

  3711 Almeria Ave Unit 3-N, Sarasota, FL 34239
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  $2,095,000

  $150K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,105 Sq Ft

  1714 South Dr, Sarasota, FL 34239

  Virtually Staged. Tucked beneath a canopy of mature trees in one of Sarasota’s most coveted neighborhoods, 1714 South Drive presents a rare opportunity to secure a prime homesite in Cherokee Park, West of the Trail and moments from the very best of Sarasota living. Set on a beautifully established lot with lush, mature landscaping, a paver driveway, and a combination of garage and carport

  Joel Schemmel DOUGLAS ELLIMAN

  1714 South Dr, Sarasota, FL 34239
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  $2,100,000

  • 4 Beds
  • 4 Baths
  • 3,148 Sq Ft

  1850 Magnolia St, Sarasota, FL 34239

  In the heart of Southside Village, this exceptional home offers one of Sarasota’s sought-after lifestyles. Just west of Tamiami Trail in Poinsettia Park’s charming Flower Streets, the neighborhood is known for its tree-lined streets, diverse architectural character, and proximity to restaurants, boutiques, gourmet markets, Sarasota Memorial Hospital, Southside Elementary, downtown Sarasota and

  CARMEN BASKIND PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1850 Magnolia St, Sarasota, FL 34239
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  $2,595,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,200 Sq Ft

  1731 Siesta Dr, Sarasota, FL 34239

  Under Construction. Brand new construction with ultra-luxury finishes, estimated for completion end of July 2026. This is the one. A statement home in one of Sarasota’s most desirable “West of the Trail” locations, designed with intention, elevated finishes, and a level of detail you simply don’t see every day. Be the first to live in it! Featuring 3 bedrooms, 2.5 bathrooms, plus a separate

  Lyndsey Kaplan THE KAPLAN GROUP RE LLC

  1731 Siesta Dr, Sarasota, FL 34239
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  /84

  $2,995,000

  $105K PRICE DROP

  • 4 Beds
  • 6 Baths
  • 3,727 Sq Ft

  1537 Siesta Dr, Sarasota, FL 34239

  Welcome to 1537 Siesta Drive—an exceptional custom coastal contemporary residence ideally positioned between Downtown Sarasota and world-renowned Siesta Key Beach. Built in 2023, this stunning luxury home offers 4 bedrooms, 4 full baths, 2 half baths, a dedicated office, and over 3,700 square feet of thoughtfully designed living space.From the moment you enter, you’re greeted by soaring

  Tina Ellis COMPASS FLORIDA LLC

  1537 Siesta Dr, Sarasota, FL 34239
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  $8,750,000

  $1M PRICE DROP

  • 5 Beds
  • 5 Baths
  • 4,031 Sq Ft

  1500 Bayview Dr, Sarasota, FL 34239

  Nestled in the heart of Sarasota, Florida, "The Seathrough House" stands as a testament to timeless elegance and modern sophistication. Designed by the acclaimed architectural firm Sweet Sparkman and meticulously crafted by builder Josh Wynne, this mid-century marvel redefines luxury living. From the moment you step inside, the panoramic bay views captivate the senses, seamlessly blending the

  Thomas Cail RE/MAX ALLIANCE GROUP

  1500 Bayview Dr, Sarasota, FL 34239
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  $1,690,000

  New Construction

  • 5 Beds
  • 2.5 Baths
  • 3,032 Sq Ft

  1647 Siesta Dr, Sarasota, FL 34239

  Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,023 square feet of living space. Additional opportunity to add bathrooms with modification add-on with the builder. From the moment you enter, you'll be captivated by the open floor plan, pool view, and fantastic design. This dazzling property, boasts an open floor plan that features high ceilings,

  Faith Stutzman PHAM REALTY GROUP LLC

  1647 Siesta Dr, Sarasota, FL 34239
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  /55

  $2,750,000

  $145K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,239 Sq Ft

  1731 Cunliff Ln, Sarasota, FL 34239

  Hidden behind lush, curated gardens on a rare .34-acre parcel in McClellan Park, west of Osprey, this is more than a home—it’s a private in-town compound designed for those who value beauty, privacy, and a deeply connected lifestyle. A winding approach reveals a residence that unfolds with intention, where indoor and outdoor living exist in perfect harmony. At its heart, a 2024 architectural

  Andrew Tanner PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1731 Cunliff Ln, Sarasota, FL 34239
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  /55

  $489,500

  • 3 Beds
  • 1 Bath
  • 1,382 Sq Ft

  2065 Goldenrod St, Sarasota, FL 34239

  Nestled in the heart of Sarasota within the top A-rated school district, this charming 3-bedroom, 1-bath home offers a prime position near various amenities. Located close to Siesta and Lido Key Beaches, the inviting shops and restaurants of Southside Village, the cultural richness of Downtown Sarasota, the upscale allure of St. Armands Circle, and the convenient Sarasota Memorial Hospital, this

  Patrick Brogley KELLER WILLIAMS ON THE WATER S

  2065 Goldenrod St, Sarasota, FL 34239
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  /2

  $1,899,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,568 Sq Ft

  1719 Shoreland Dr, Sarasota, FL 34239

  This newly remodeled West of the Trail home sits on a rare spring-fed lake on a private street. The home has been tastefully updated and offers 2 en-suite guest bedrooms with a split-plan master bedroom. The home is complete with high ceilings, an open floor plan, new paint, new luxury plank flooring, contemporary fixtures, some new vanities, and other new features. Beautiful sliding doors and

  Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1719 Shoreland Dr, Sarasota, FL 34239
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  $4,100,000

  • 4 Beds
  • 3.5 Baths
  • 4,857 Sq Ft

  1829 Bougainvillea St, Sarasota, FL 34239

  Experience the timeless charm and distinctive elegance of this West of Trail luxury cottage, with modern finishes that remain true to its original allure, at 1829 Bougainvillea Street. Occupying three lots, it is nestled gracefully in Sarasota's most cherished neighborhood. Set on a tranquil, tree-lined avenue, moments from vibrant Southside Village, Sarasota Memorial Hospital, and the renowned

  Ryan Skrzypkowski COLDWELL BANKER REALTY

  1829 Bougainvillea St, Sarasota, FL 34239

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