Southside Homes for Sale

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  /5

  $750,000

  • Land
  • 0.20 Acre
  • $3,750,000 per Acre

  1958 Bougainvillea St, Sarasota, FL 34239

  If you've been waiting to build in Sarasota's most popular neighborhood these opportunities are rapidly disappearing. Great West of Trail location on one of the neighborhood's favorite tree lined streets. Large beautiful lot with a deep back yard. Just a few blocks to Southside Village shops, markets and restaurants plus there is downtown Sarasota moments away, the bay front and of course

  Jenifer Schwell MICHAEL SAUNDERS & COMPANY

  1958 Bougainvillea St, Sarasota, FL 34239
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  /19

  $6,500,000

  • Land
  • 1.27 Acres
  • $5,118,110 per Acre

  3350 Old Oak Dr, Sarasota, FL 34239

  Rarely does an opportunity like this come to market—a chance to own a piece of Old Florida on over an acre of lush, private grounds. Nestled in total seclusion, this extraordinary compound offers panoramic views of Sarasota Bay, Siesta Key, Bird Key, the Ringling Bridge, and downtown Sarasota. The property features a Mid-Century modern home alongside a vacant lot, creating endless possibilities

  Nora Johnson MICHAEL SAUNDERS & COMPANY

  3350 Old Oak Dr, Sarasota, FL 34239
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  /35

  $3,300,000

  • Land
  • 0.52 Acre
  • $6,346,154 per Acre

  3348 Old Oak Dr, Sarasota, FL 34239

  Stunning Mid Century Masterpiece, close to beach and walk to Southside Village. Featuring cypress inside and out. High ceilings and open spaces offer comfort and airiness, while the walls of glass sliders and windows fill the interior with natural lighting while showcasing gorgeous views of the lush landscaping. The expansive great room features floor-to-ceiling sliders and a wood-burning

  Nora Johnson MICHAEL SAUNDERS & COMPANY

  3348 Old Oak Dr, Sarasota, FL 34239
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  /19

  $9,800,000

  • 7 Beds
  • 8 Baths
  • 7,181 Sq Ft

  3350 Old Oak Dr, Sarasota, FL 34239

  Rarely does an opportunity like this come to market, offering a piece of Old Florida on 2.1 lush acres and boasting breathtaking views of Sarasota Bay, Siesta Key, Bird Key, Ringling Bridge, and downtown Sarasota, this magnificent family compound features two custom-built Mid Century homes and a vacant lot, offering limitless possibilities. Designed to take advantage of the amazing views, the

  Nora Johnson MICHAEL SAUNDERS & COMPANY

  3350 Old Oak Dr, Sarasota, FL 34239
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  /37

  $1,499,000 Open Sun 12:30PM - 2:30PM

  • 4 Beds
  • 4 Baths
  • 2,853 Sq Ft

  1775 Stapleton St, Sarasota, FL 34239

  Would you like to be minutes to Siesta Key Beach with ease of access to downtown & other attractions? Look no further than in the family friendly, gated & hidden gem of a community - Granada Park. This "West of Trail" 4 bedroom, 4 bath sunny home is located 2.5 miles from downtown, 0.3 miles from Publix, 1 mile to Southside Elementary school, 1.5 miles to Southside Village and only 1.6 miles to

  Kate Taylor COLDWELL BANKER REALTY

  1775 Stapleton St, Sarasota, FL 34239
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  /51

  $1,799,000

  • 3 Beds
  • 3 Baths
  • 2,839 Sq Ft

  1616 North Dr, Sarasota, FL 34239

  One or more photo(s) has been virtually staged. Welcome to 1616 North Drive, Fourth in from the Bay in Coveted CHEROKEE PARK. EXCELLENT LOCATION to Build a New Home or Renovate the Existing Home on this Spacious 100' x 150' (15,000 Sq. Ft.) Lot. Boundary and Tree Survey Available upon Request.Walk Right Down the Sidewalk to Southside Elementary School. Over 2,800 Sq. Ft. of Living Area Including

  Chris Kernan RE/MAX ALLIANCE GROUP

  1616 North Dr, Sarasota, FL 34239
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  /45

  $650,000

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  3511 Camino Real, Sarasota, FL 34239

  MOTIVATED SELLER! Nestled in one of Sarasota's most sought-after West-of-Trail neighborhoods, this beautifully maintained single-family residence offers a perfect blend of coastal charm and modern convenience. Just minutes from Siesta Key and its world-renowned beaches, this home is surrounded by multi-million-dollar properties, making it an exceptional investment opportunity. This 2-bedroom,

  Dean Hinterstoisser KELLER WILLIAMS ON THE WATER S

  3511 Camino Real, Sarasota, FL 34239
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  /26

  $299,000

  • 2 Beds
  • 1 Bath
  • 991 Sq Ft

  3700 S Osprey Ave Unit 214, Sarasota, FL 34239

  Discover your ideal sanctuary at Plaza Gardens, a stunningly remodeled condo that perfectly balances tranquility and luxury. Nestled amidst lush tropical greenery and meticulously maintained gardens, this boutique-style residence offers a serene environment for those seeking a peaceful retreat. Conveniently located just southeast of Siesta Key's North Bridge and west of the trail, you'll have

  Andrea Cohen COLDWELL BANKER REALTY

  3700 S Osprey Ave Unit 214, Sarasota, FL 34239
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  /64

  $6,900,000

  • 5 Beds
  • 7 Baths
  • 7,960 Sq Ft

  3544 San Remo Terrace, Sarasota, FL 34239

  Crowning the esteemed West-of-Trail neighborhood of San Remo Estates, this grand 7,960 sq ft waterfront property, carefully positioned to capture only breathtaking views, epitomizes luxury waterfront living. Sprawling bay and inter-coastal views, only panoramic, and rarely available here. This estate is not just a home; it is a resort in its own right, offering a lifestyle of unparalleled

  Ryan Skrzypkowski COLDWELL BANKER REALTY

  3544 San Remo Terrace, 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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  /15

  $269,000

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft

  3360 S Osprey Ave Unit 102B, Sarasota, FL 34239

  BERMUDA ON OSPREY - OASIS ON OSPREY. 1st. Floor end unit 2BR/ 2 full Baths Condo. West of Trail. Home in very private location in bldg. Eat-In Kitchen with built-in features, granite countertops, wood cabinets, glass top range, microwave, refrigerator, dishwasher. (Eat-in area could be used as office, etc.) Living Room/Dining Room with sliding glass doors to screened lanai. Split bedrooms. Open

  Larry Haymore RE/MAX ALLIANCE GROUP

  3360 S Osprey Ave Unit 102B, Sarasota, FL 34239
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  /2

  $1,480,000

  • Land
  • 0.33 Acre
  • $4,484,848 per Acre

  2155 Oriole Dr, Sarasota, FL 34239

  This is a vacant lot

  Stephen Hachey FLAT FEE MLS REALTY

  2155 Oriole Dr, Sarasota, FL 34239
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  /41

  $2,725,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,237 Sq Ft

  1559 Bay Rd, Sarasota, FL 34239

  New Construction by Majestik HomesMove-In Ready | Easy to ShowWelcome to 1559 Bay Road, a new home by Majestik Homes, ideally located West of the Trail in Sarasota’s coveted Granada neighborhood. Just 4.6 miles from Siesta Beach, 6.0 miles from Lido Beach, and only 1.9 miles from Sarasota Memorial Hospital, this prime address places you near upscale restaurants, artisan deli

  Alesia Stirp ALESIA DEANNA STIRP

  1559 Bay Rd, Sarasota, FL 34239
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  /7

  $6,000,000 New Construction

  • 5 Beds
  • 9 Baths
  • 4,450 Sq Ft

  2100 Mcclellan Pkwy, Sarasota, FL 34239

  Pre-Construction. To be built. Pre-construction, to be built. Situated West of the Trail, this exceptional estate represents the pinnacle of luxury living in Sarasota. Developed by M&J Pham Development, this residence is a masterpiece of innovative, forward-thinking design and flawless craftsmanship. Inside, you'll discover an open floor plan that harmoniously blends expansive spaces with

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  2100 Mcclellan Pkwy, Sarasota, FL 34239
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  /96

  $4,875,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 4.5 Baths
  • 3,970 Sq Ft

  1827 Morris St, Sarasota, FL 34239

  The “St. Michael” is award-winning Allegra Homes’ 2025 fully furnished model home supremely located just south of downtown Sarasota’s cultural epicenter in the coveted West of Trail area where residents know first-hand what a wonderful community they live in. Prepare to be captivated by the seamless fusion of modern design, artful nuances, and stylish sophistication. Every detail has been curated

  Karen Greco GRECO REAL ESTATE

  1827 Morris St, Sarasota, FL 34239
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  /31

  $2,899,990 New Construction

  • 4 Beds
  • 4 Baths
  • 3,292 Sq Ft

  1876 Magnolia St, Sarasota, FL 34239

  Under Construction. This stunning 2-story “Palonia IV Coastal” floor plan is one of the newest additions to the Allegra Homes collection of exquisite luxury residences and is located in the prestigious West of Trail area near Siesta Drive, your direct pathway to Siesta Key. The cornerstone of the Allegra Homes’ vision is a dedication to excellence in custom home building and providing the very

  Karen Greco GRECO REAL ESTATE

  1876 Magnolia St, Sarasota, FL 34239
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  /58

  $11,900,000 New Construction

  • 5 Beds
  • 8 Baths
  • 7,110 Sq Ft

  1610 N Lodge Dr, Sarasota, FL 34239

  This stunning three story, coastal modern, single-family waterfront home is the perfect blend of comfort and luxury located in the treasured Cherokee Park neighborhood. Nestled on a street adorned with majestic oak and canopy trees, this exceptional property offers both privacy and grandeur. As you approach this generous lot, you'll be greeted by an electric gate entryway. Choose to park in

  Kelly Gettel COLDWELL BANKER REALTY

  1610 N Lodge Dr, Sarasota, FL 34239
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  /61

  $3,500,000 New Construction

  • 4 Beds
  • 6 Baths
  • 3,613 Sq Ft

  1783 Bayview Dr, Sarasota, FL 34239

  Welcome to an exquisite 3,613 sqft New Construction home nestled near a highly coveted and sought after location in Sarasota. Built by M&J Pham Development, this residence offers unparalleled combination of complete sophistication and designed for livable luxury. The warm and inviting palette is both trend-forward and timeless. As you enter, you will be greeted by a soaring 2 story great room

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  1783 Bayview Dr, Sarasota, FL 34239
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  /52

  $3,000,000 New Construction

  • 5 Beds
  • 5 Baths
  • 3,595 Sq Ft

  1805 Goldenrod St, Sarasota, FL 34239

  One or more photo(s) has been virtually staged. Welcome to this stunning 2-story luxury home built by M&J Pham Development, featuring 5 bedrooms, 4.5 bathrooms, and 3,595 square feet of living space. From the moment you step inside, you'll be captivated by the open floor plan, high-end finishes, and fantastic design. The home features a modern and elegant kitchen with top-of-the-line Viking

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  1805 Goldenrod St, Sarasota, FL 34239
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  /40

  $9,750,000 Open Sun 12PM - 3PM

  • 5 Beds
  • 7 Baths
  • 5,328 Sq Ft

  3621 San Remo Terrace, Sarasota, FL 34239

  Under Construction. Only a few weeks from completion, come and experience the epitome of luxury! Nestled on a quiet cul-de-sac west of Orange Avenue, this Florida Coastal masterpiece by Seaward Homes offers 5300 sq. ft. of prime waterfront living. With a bayou stretching almost 400 feet wide, enjoy direct access to the breathtaking Sarasota Bay and BIG WATER VIEWS that define coastal

  Patrick Dipinto, III COLDWELL BANKER REALTY

  3621 San Remo Terrace, Sarasota, FL 34239

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