Recently Sold Southside Homes

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  /2

  $1,872,000 Sold Feb 10, 2025

  • 2,956 Sq Ft
  • $633/SF
  • 123 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2024

  3523 Jacinto Ct, Sarasota, FL 34239

  Brand new and just completed luxury block home. This 2,958 SQFT home features 4 ample sized bedrooms, 3 with walk-in closets, each bedroom has a full bath. Large 18x15 loft/bonus room with a slider and covered back porch (loft can accommodate a king size bed, bunk beds, or multiple twin beds), PGT impact windows, wood floors throughout, metal roof, first floor master bedroom, master bath - all

  Paul Defelice HOUSEMAX REALTY LLC

  3523 Jacinto Ct, Sarasota, FL 34239
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• 

  

  /2

  $1,600,000 Sold Feb 07, 2025

  • 2,426 Sq Ft
  • $660/SF
  • 98 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1943

  3616 Flores Ave, Sarasota, FL 34239

  True Vintage home from 1943. Charms abound throughout this wonderful, only second owner home. Original oak floors are only one of many features that await you when you enter the front door through the welcoming totally private courtyard. Present owners have done many upgrades through the years while maintaining the ambiance throughout. Legal, totally Furnished, self-contained, 5 room

  Sheryl Morris REALTY SERVICES INC

  3616 Flores Ave, Sarasota, FL 34239
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  /2

  $2,950,000 Sold Jan 31, 2025

  • 2,670 Sq Ft
  • $1,105/SF
  • 14 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2014

  2004 S Osprey Ave, Sarasota, FL 34239

  Experience the pinnacle of modern design and impeccable craftsmanship in this stunning architectural masterpiece West of the Trail. Perfectly situated in the heart of Southside Village, this extraordinary residence showcases a harmonious blend of streamlined concrete and warm mahogany, delivering a striking visual appeal that resonates with today’s discerning buyer. Designed with precision

  Nora Johnson MICHAEL SAUNDERS & COMPANY

  2004 S Osprey Ave, Sarasota, FL 34239
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  /2

  $2,825,000 Sold Jan 24, 2025

  • 2,844 Sq Ft
  • $993/SF
  • 14 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  1521 Bay Rd, Sarasota, FL 34239

  Move-in ready and easy to see! Welcome to 1521 Bay Road, a brand-new single-story masterpiece by Majestik Homes, known for their high-quality craftsmanship. Nestled West of the Trail, this home seamlessly combines modern design with thoughtful functionality to create a luxurious and inviting living experience.As you enter through the impressive double front doors, you’re greeted by a

  Charles Simons, III MAJESTIK REALTY

  1521 Bay Rd, Sarasota, FL 34239
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  /2

  $1,875,000 Sold Jan 24, 2025

  • 2,439 Sq Ft
  • $769/SF
  • 0 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1928

  1862 Prospect St, Sarasota, FL 34239

  ACCEPTING BACK-UP OFFERS. Welcome to 1862 Prospect Street, "Big Banya.” This rare find in Southside Village features three bedrooms and three bathrooms, combining old Florida allure with modern amenities. Built in 1928, (affective build date 2013) it offers 2,439 square feet of living space on a half-acre lot adorned with beautiful gardens and majestic trees. As you enter, you are greeted by a

  Georgia Salaverri COMPASS FLORIDA LLC

  1862 Prospect St, Sarasota, FL 34239
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  /2

  $2,200,000 Sold Jan 15, 2025

  • 2,617 Sq Ft
  • $841/SF
  • 8 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2013

  1815 Grove St, Sarasota, FL 34239

  Experience unparalleled luxury and comfort in this stunning home, located in the highly sought-after West of the Trail neighborhood. Built in 2013, this residence effortlessly blends sophisticated design with functional living. Featuring a spacious open floor plan, a first-floor primary suite, a chef-inspired kitchen, and a private backyard oasis with a sparkling pool and outdoor kitchen, this

  Mairead Smialek COLDWELL BANKER REALTY

  1815 Grove St, Sarasota, FL 34239
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  /2

  $2,350,000 Sold Jan 08, 2025

  • 2,762 Sq Ft
  • $851/SF
  • 0 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1941

  1750 Seminole Dr, Sarasota, FL 34239

  Welcome to this timeless gem in the highly sought after McClellan Park neighborhood, West of Trail. Originally built in 1941 and thoughtfully remodeled in 2012, this lovely home seamlessly blends historic charm with modern luxury. As you step inside, you'll be greeted by the stunning original pecky cypress, high ceilings, and an abundance of natural light. The floor plan offers a perfect balance

  Alison Elizalde MICHAEL SAUNDERS & COMPANY

  1750 Seminole Dr, Sarasota, FL 34239
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  /2

  $4,450,000 Sold Jan 02, 2025

  • 4,215 Sq Ft
  • $1,056/SF
  • 5 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2020

  1623 North Dr, Sarasota, FL 34239

  We can’t remember the last time a home made us feel this way. Walking through this property, you instantly sense something extraordinary. Bringing a home like this to market is a rare privilege. Located in Cherokee Park, one of Sarasota’s most sought-after neighborhoods, this 4-bedroom, 4.5-bath home is a sanctuary of thoughtful design and unmatched craftsmanship. The oversized lot

  Ryan Skrzypkowski COLDWELL BANKER REALTY

  1623 North Dr, Sarasota, FL 34239
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  /2

  $518,000 Sold Dec 31, 2024

  • 1,468 Sq Ft
  • $353/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  1742 Wisconsin Ln, Sarasota, FL 34239

  Fixer-upper investment opportunity near Siesta Key! Welcome to 1742 Wisconsin Lane in sunny Sarasota, an investor's dream just minutes from world-famous Siesta Key Beach. This single-family home boasts good bones and a spacious layout, ready for your vision! Featuring three bedrooms, and an expansive two-car garage, this property has endless potential to transform into a modern, coastal retreat

  Roberta Tengerdy, PA PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1742 Wisconsin Ln, Sarasota, FL 34239
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  /2

  $679,000 Sold Dec 30, 2024

  • 1,658 Sq Ft
  • $410/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  1905 Jasmine Dr, Sarasota, FL 34239

  West of the Trail this amazing location is convenient to restaurants, shopping, Southside Elementary, a short drive to Southside Village and downtown Sarasota. Siesta key public beach is only 10 minutes away! This well equipped, well cared for 3 bedroom, 2 bath home is move in ready, with all furniture included. There are tiled floors throughout the home (no carpeting). Two of the bedrooms have

  Chet Zoltak COLDWELL BANKER REALTY

  1905 Jasmine Dr, Sarasota, FL 34239
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  /2

  $1,500,000 Sold Dec 13, 2024

  • Land
  • 0.33 Acre
  • $4,545,455 per Acre

  • 57 Days On Market

  2155 Oriole Dr, Sarasota, FL 34239

  Presenting a rare opportunity to build your dream estate on a stunning vacant lot in the prestigious west of trail neighborhood of McClellan Park. This exclusive and private parcel boasts 13,198 SF and an enviable location between Harbor Acres and Cherokee Park, on a quiet street just one block from Sarasota Bay but with an X500 flood zone buildable footprint. Surrounded by multi-million-dollar

  Mackenzie Longueuil MICHAEL SAUNDERS & COMPANY

  2155 Oriole Dr, Sarasota, FL 34239
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  /2

  $3,400,000 Sold Dec 06, 2024

  • 3,569 Sq Ft
  • $953/SF
  • 150 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2020

  1555 Sandpiper Ln, Sarasota, FL 34239

  This stunning West of The Trail 4BR/4BA plus office and bonus room with gas heated pool residence from Award winning Allegra Homes offers the expanded two-story “Gloria” model complete with an elevator. Coastal and casual elegance describe this light and beautiful home with 20 ft. beamed ceilings. Engineered hardwoods are featured on the main living area which seamlessly flows into the spacious

  Jay Mitchell COLDWELL BANKER REALTY

  1555 Sandpiper Ln, Sarasota, FL 34239
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  /2

  $9,400,000 Sold Dec 02, 2024

  • 8,125 Sq Ft
  • $1,157/SF
  • 0 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 2003

  3000 Southwest Dr, Sarasota, FL 34239

  Owner has reduced price to a point creating an exciting opportunity to own one of Sarasota’s great estates. Discover the perfect blend of elegance and privacy on this 1.6-acre estate nestled within Cherokee Park, one of the most sought-after mainland neighborhoods in Sarasota. Tucked away on a small street at the end of Southwest Drive, this double lot estate is in a beautiful setting unlike any

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  3000 Southwest Dr, Sarasota, FL 34239
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  /2

  $775,000 Sold Nov 26, 2024

  • 1,110 Sq Ft
  • $698/SF
  • 16 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1948

  1617 Siesta Dr, Sarasota, FL 34239

  Look no further, as this charming bungalow awaits its new owner! Perfect home to live the Florida lifestyle while unlocking the potential of this exceptional offering - an expansive lot spanning nearly 12,000 square feet in the coveted West of Trail area, with the added benefit of city-approved subdivision into two 5,000+ square foot lots. Positioned for maximum flexibility, this property

  Liz Arme PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1617 Siesta Dr, Sarasota, FL 34239
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  /2

  $965,000 Sold Nov 22, 2024

  • 1,769 Sq Ft
  • $546/SF
  • 6 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1938

  1863 Bougainvillea St, Sarasota, FL 34239

  Discover this well-priced opportunity in the coveted Southside Village neighborhood: a charming 1938 cottage that combines classic character with modern amenities. Nestled on Bougainvillea Street, one of the most picturesque of Sarasota's beloved flower streets, this home features original wood floors, high ceilings, and a renovated kitchen, all while offering roomy storage uncommon for its

  Nick Gard COLDWELL BANKER REALTY

  1863 Bougainvillea St, Sarasota, FL 34239
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  /2

  $2,300,000 Sold Nov 20, 2024

  • 4,046 Sq Ft
  • $568/SF
  • 18 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2008

  3714 Flores Ave, Sarasota, FL 34239

  IF YOU ARE LOOKING FOR THE BEST WEST OF TRAIL PROPERTY WITHIN A 5 MINUTE WALK TO SOUTHSIDE VILLAGE, SARASOTA MEMORIAL HOSPITAL, SOUTHSIDE ELEMENTARY AND 2 MILES TO DOWNTOWN, THEN THIS IS THE ONE! Start your morning with a bike ride to Siesta Beach, ranked the number one beach in the USA. Enjoy the sugar-white sand or the turquoise waters of the Gulf of Mexico, and capture breathtaking sunsets in

  Marina Solo KW SUNCOAST

  3714 Flores Ave, Sarasota, FL 34239
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  /2

  $3,775,000 Sold Nov 06, 2024

  • 3,136 Sq Ft
  • $1,204/SF
  • 94 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2002

  1547 Sandpiper Ln, Sarasota, FL 34239

  This one-of-a-kind elegant retreat is in the heart of the well-established, historic neighborhood of McClellan Park and in the middle of it all steps from the waterfront, downtown Sarasota and Southside Village. Step inside and experience a world of exquisite interiors, where every detail has been thoughtfully curated to create a space that is visually stunning and effortlessly inviting. This

  Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1547 Sandpiper Ln, Sarasota, FL 34239
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  /2

  $1,400,000 Sold Nov 05, 2024

  • 2,345 Sq Ft
  • $597/SF
  • 136 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1953

  1600 Wewa Dr, Sarasota, FL 34239

  Must See Home in extremely desirable enclave of McClellan Park, a West of the Trail, 56 Acres large neighborhood established by the McClellan sisters in 1916. This area is within City limits, just a short drive to the Downtown Sarasota area and all that it has to offer including a large variety of restaurants, shopping, Opera House, Marie Selby Botanical Garden, Bay Park, Sarasota Memorial

  Miriam Pearson COLDWELL BANKER REALTY

  1600 Wewa Dr, Sarasota, FL 34239
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  /2

  $2,650,000 Sold Nov 05, 2024

  • 3,547 Sq Ft
  • $747/SF
  • 578 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2023

  1912 Wisteria St, Sarasota, FL 34239

  Peace of mind can be yours while living your desirable Suncoast lifestyle. This move-in ready home is situated 20 feet above sea level and is designed to provide safety against the elements with durable materials and impact rated windows and doors. Nestled in the desirable ‘West of the Trail’ area, this newly constructed marvel offers precise attention to detail in its 3,547 sq ft. A

  Rudy Dudon MICHAEL SAUNDERS & COMPANY

  1912 Wisteria St, Sarasota, FL 34239
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  /2

  $711,900 Sold Oct 29, 2024

  • 1,524 Sq Ft
  • $467/SF
  • 143 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1950

  1966 Wisteria St, Sarasota, FL 34239

  Here's your opportunity to own a property "West of the Trail" on one of the highly coveted flower streets within the City of Sarasota! This incredibly unique three bedroom two bath home captures the very essence of what Sarasota living once was. There's gorgeous wood flooring throughout the original floorplan, oversized bedrooms, a vintage pink tile bathroom, original wood kitchen cabinets, and

  Daniel Flath COMPASS FLORIDA LLC

  1966 Wisteria St, Sarasota, FL 34239
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  /2

  $1,915,000 Sold Oct 23, 2024

  • 2,479 Sq Ft
  • $772/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 2001

  1827 Grove St, Sarasota, FL 34239

  Experience unparalleled luxury and comfort in this beautifully RENOVATED home in the highly desired prime location west of the trail. Meticulously updated, this residence seamlessly blends style with functionality. Enjoy a spacious open floor plan, a newly designed chef's kitchen, and a private backyard oasis featuring a serene, sparkling pool. Don't want a project - just bring your toothbrush!

  Mairead Smialek COLDWELL BANKER REALTY

  1827 Grove St, Sarasota, FL 34239
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  /2

  $416,300 Sold Sep 20, 2024

  • 1,391 Sq Ft
  • $299/SF
  • 39 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  2050 Bougainvillea St, Sarasota, FL 34239

  Welcome to the Arlington Park / Southgate Neighborhood of Sarasota. This property boasts a lot that is 62 X 145 X 62 X 146 along with being the 6th property to the East of US41.This 3 Bedroom 2 Full Bathroom home has the perfect Florida charm with tile throughout. You don't worry about bringing the Siesta Key Sand home. The property is located only 5 blocks North of Siesta Drive. Which, gives a

  Rodney Miles PRIVATE WEALTH REALTY INC

  2050 Bougainvillea St, Sarasota, FL 34239
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  /2

  $330,000 Sold Jun 04, 2025

  • 1,122 Sq Ft
  • $294/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  3360 S Osprey Ave Unit 211B, Sarasota, FL 34239

  Fully furnished Turnkey 2 bedroom 2 bath condo.

  Evan Weber MICHAEL SAUNDERS & COMPANY

  3360 S Osprey Ave Unit 211B, Sarasota, FL 34239
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  /2

  $850,000 Sold May 30, 2025

  • 1,845 Sq Ft
  • $461/SF
  • 0 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1966

  1834 Bougainvillea St, Sarasota, FL 34239

  CHARMING POINSETTIA PARK GEM WITH POOL & TIKI BAR. This delightful 3-bedroom, 3-bathroom home captures the essence of South Poinsettia Park's eclectic charm. Bring your imagination to this residence, envision your perfect lifestyle and reimagine this space as uniquely yours. The property showcases a magnificent grand oak as its centerpiece, lending timeless character to this reimagined ranch

  Mickey Kiernan MICHAEL SAUNDERS & COMPANY

  1834 Bougainvillea St, Sarasota, FL 34239

Showing Results 41 - 64, Page 2 of 2