Southside Homes for Sale

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  $295,000

  • 2 Beds
  • 2 Baths
  • 976 Sq Ft

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

  Nestled in a quiet and highly desirable Sarasota community west of Tamiami Trail, this charming condo offers unbeatable convenience with close proximity to Siesta Key Beach, Southside Village, Publix, dining, and everyday amenities. Featuring 2 bedrooms, each with its own ensuite bathroom, this 976 sq. ft. residence provides an efficient and comfortable layout ideal for both relaxation and

  Michelle Ward COMPASS FLORIDA LLC

  3711 Almeria Ave Unit 3-N, Sarasota, FL 34239
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  $1,650,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,910 Sq Ft

  1730 Wisconsin Ln, Sarasota, FL 34239

  One or more photo(s) has been virtually staged. Located West of the Trail, this newly built modern home offers exceptional value in one of Sarasota’s most desirable in-city neighborhoods. Built in 2024, the residence features 4 bedrooms, 4.5 baths, and approximately 2,900 square feet of thoughtfully designed living space. Positioned within city limits, it provides flexibility for rental

  Keith Kleppinger COLDWELL BANKER REALTY

  1730 Wisconsin Ln, Sarasota, FL 34239
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  $1,545,000

  • 5 Beds
  • 4.5 Baths
  • 3,033 Sq Ft

  3838 Flores Ave, Sarasota, FL 34239

  A premier West of Trail address in Granada. A property rarely duplicated in Sarasota. Casa de Flores is a 1920s Spanish Revival compound designed for modern flexibility — multi-generational living, private guest quarters, and exceptional indoor-outdoor entertaining — all set within one of Sarasota’s most coveted neighborhoods of Granada. The main residence offers two bedrooms and two baths,

  Pam Charron COMPASS FLORIDA LLC

  3838 Flores Ave, Sarasota, FL 34239
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  /47

  $6,990,000

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

  1504 S Lodge Dr, Sarasota, FL 34239

  First time available in 40 years! "Tween Bridges" is a rare bayfront property located in highly sought-after Cherokee Park, West of Trail. This 4-bedroom,3.5 bath residence offers unobstructed panoramic views of Sarasota Bay. The breathtaking sunsets and stunning vistas of Ringling Bridge, Siesta Key and downtown are truly mesmerizing. Boating enthusiasts will appreciate the brand-new dock with a

  Melody Davis COLDWELL BANKER REALTY

  1504 S Lodge Dr, Sarasota, FL 34239
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  $11,500,000 New Construction

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

  1610 N Lodge Dr, Sarasota, FL 34239

  Stunning waterfront 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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  $299,000

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

  3360 S Osprey Ave Unit 104B, Sarasota, FL 34239

  Move-in ready 2-bedroom, 2-bath tastefully decorated ground floor condo located in the desirable Oasis of Osprey, West of the Trail. This well-maintained unit features an upgraded kitchen with granite countertops and stainless steel appliances, along with updated bathrooms. Enjoy indoor-outdoor living with a screened lanai and brick paver patio, plus the added convenience of a private 6x6 storage

  Marlin Yoder HARRY ROBBINS ASSOC INC

  3360 S Osprey Ave Unit 104B, Sarasota, FL 34239
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  /22

  $224,900

  • 2 Beds
  • 1.5 Baths
  • 991 Sq Ft

  3700 S Osprey Ave Unit 219, Sarasota, FL 34239

  West of the Trail location perfect for going to the beach or Downtown. Perfect for a winter getaway or full time living. 2nd floor unit with enclosed patio. Beautiful gardens and trees surround the property. 2 bedroom 1 bath (room for another 1/2 bath), dual sinks, on-site laundry, elevator and pets are welcome! A Washer & Dryer may be installed in the unit.One designated parking spot and guest

  Kelly Anderson RE/MAX ALLIANCE GROUP

  3700 S Osprey Ave Unit 219, Sarasota, FL 34239
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  /2

  $2,000,000

  • Land
  • 0.46 Acre
  • $4,347,826 per Acre

  1749 Cherokee Dr, Sarasota, FL 34239

  This exceptional 100X200 lot in historic Cherokee Park awaits your dream home, with Fergeson Brothers design/construction as the designated builder; this west-of-the-trail neighborhood is located on Sarasota Bay in the City of Sarasota; The adjoining lot is also available.

  Rogers Moore COLDWELL BANKER REALTY

  1749 Cherokee Dr, Sarasota, FL 34239
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  $4,500,000

  • 3 Beds
  • 2.5 Baths
  • 4,660 Sq Ft

  1400 Siesta Dr, Sarasota, FL 34239

  Welcome to 1400 Siesta Drive, where refined waterfront living becomes your everyday reality. This home is quietly tucked away behind a gated entrance, with an additional secondary gate providing exclusive access to the residence. Thoughtfully designed to embrace breathtaking, unobstructed views of Sarasota Bay, this modern residence is a showcase of light, space, and coastal elegance. Expansive

  Matthew Voss PREFERRED SHORE LLC

  1400 Siesta Dr, Sarasota, FL 34239
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  /70

  $13,250,000

  • 5 Beds
  • 7 Baths
  • 8,125 Sq Ft

  3000 Southwest Dr, Sarasota, FL 34239

  One of Sarasota’s greatest bayfront estates, this stunning 1.38 acre waterfront home has recently undergone a comprehensive renovation throughout, enhancing every room with refined finishes and modern systems while preserving its timeless architectural character. Hidden away at the end of Southwest Drive within the coveted Cherokee Park neighborhood, this 5-bedroom home offers exceptional

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  3000 Southwest Dr, Sarasota, FL 34239
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  /51

  $1,100,000

  • 4 Beds
  • 4 Baths
  • 2,020 Sq Ft

  1761 Siesta Dr, Sarasota, FL 34239

  Siesta Key Triplex – High-Yield, Weekly Rental Zoned Investment! Concrete triplex in city limits featuring one 2BR/2BA and two 1BR/1BA units with long-term tenants in place...immediate cash flow from day one. Proven income of $65K–$85K annually with low overhead expenses (taxes, insurance, landscaping only). Tenants pay all utilities with separate electric & water meters for each unit. Weekly

  Danielle Dietrich COLDWELL BANKER REALTY

  1761 Siesta Dr, Sarasota, FL 34239
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  /2

  $2,000,000

  • Land
  • 0.46 Acre
  • $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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  $1,995,000

  • 5 Beds
  • 3.5 Baths
  • 3,790 Sq Ft

  1732 Shoreland Dr, Sarasota, FL 34239

  Welcome to modern West of Trail living — where space, style, and location come together in one of Sarasota’s most desirable family neighborhoods. Designed for the buyer who wants room to grow without sacrificing lifestyle or convenience, this stunning newer construction home offers the perfect balance of luxury, functionality, and everyday ease. From the moment you arrive, the quiet, tree-lined

  Mark Coppens EXP REALTY LLC

  1732 Shoreland Dr, Sarasota, FL 34239
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  $1,195,000

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

  1958 Morris St, Sarasota, FL 34239

  One or more photo(s) has been 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

  Jon Patella WAGNER REALTY

  1958 Morris St, Sarasota, FL 34239
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  $2,245,000

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

  1714 South Dr, Sarasota, FL 34239

  One or more photo(s) has been 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

  Joel Schemmel DOUGLAS ELLIMAN

  1714 South Dr, Sarasota, FL 34239
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  /66

  $1,300,000

  • 5 Beds
  • 4 Baths
  • 2,175 Sq Ft

  1760 Wisconsin Ln, Sarasota, FL 34239

  Siesta Key Triplex – Weekly Rental Zoned Investment Opportunity Concrete triplex in city limits featuring one 3BR/1BA unit with attached 1BR/1BA studio and two additional 1BR/1BA units. ALL units are tenant-occupied with immediate income potential; historical annual income reported at $80K–$100K. Zoned for weekly rentals in Siesta Key City Limits...allow short- or long-term rental flexibility.

  Danielle Dietrich COLDWELL BANKER REALTY

  1760 Wisconsin Ln, Sarasota, FL 34239
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  $9,750,000

  • 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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  /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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  /100

  $2,400,000

  • 10 Beds
  • 8 Baths
  • 4,435 Sq Ft

  1761 Siesta Dr, Sarasota, FL 34239

  7 Rentable Units | 10 Bed, 8 Bath Income Property – Prime Siesta Key Location! Exceptional opportunity to own a fully leased multifamily property just minutes from world-famous Siesta Key Beach. Located on Siesta Drive—the gateway to Siesta Key—this offering includes two adjacent triplexes on two separate lots, with potential to expand to 8 units. The property features a versatile mix of 1BR,

  Danielle Dietrich COLDWELL BANKER REALTY

  1761 Siesta Dr, Sarasota, FL 34239
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  $1,899,000

  • 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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  $449,000

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft

  1740 Wisconsin Ln, Sarasota, FL 34239

  OPPORTUNITY KNOCKS! Here is your chance to own the least expensive property in the most expensive neighborhood. It is all about location. This is a rarely available property and is situated in the highly desirable West of Osprey Ave. and just south of the Cherokee Park area. The home is a 76 year old Cracker style, one bedroom cottage built in 1949 on 50x104 lot. THIS HOME IS NOT LOCATED IN A

  Dan Heschmeyers GULF SHORES REALTY ERA POWERED

  1740 Wisconsin Ln, Sarasota, FL 34239

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