South Highland Real Estate

South Highland Real Estate

Welcome to South Highland, a captivating subdivision nestled in the heart of South Sarasota, Florida. This charming community offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and everyone in between.

South Highland boasts a variety of beautifully designed homes, each reflecting the unique character and style of Florida living. With lush landscaping and manicured lawns, this neighborhood invites residents to enjoy the great outdoors. The homes here range from cozy single-family residences to spacious modern designs, catering to diverse preferences and lifestyles.

One of the standout features of South Highland is its prime location. Residents have easy access to the stunning beaches of Sarasota, renowned for their soft sands and crystal-clear waters. Enjoy a day soaking up the sun at Siesta Key Beach or take a leisurely stroll along the picturesque shoreline. For those who appreciate nature, the nearby Myakka River State Park offers hiking trails, wildlife viewing, and opportunities for kayaking and fishing.

In addition to its natural beauty, South Highland is conveniently located near shopping centers, dining options, and recreational facilities. Local parks provide ample space for outdoor activities, while top-rated schools ensure that families have access to quality education.

With its friendly atmosphere and vibrant community spirit, South Highland is more than just a place to live; it’s a place to thrive. Discover the charm of this delightful subdivision and make it your home today!

Newest Listings in South Highland

4 Beds ⋅ 2 Baths ⋅ South Highland SubDv. ⋅ 34231 Zip Code

Fully renovated, income-producing duplex in a prime Sarasota location, perfect for investors or owner-occupants! This property has been completely redone with all work permitted, offering true peace of mind and zero deferred maintenance. Major upgrades include a new shingle roof, new AC systems, full electrical rewire, new plumbing, and impact-rated windows and doors for hurricane protection. Both units feature modern, move-in-ready interiors with tile flooring throughout, new drywall, updated cabinetry, and stainless steel appliances, making this a turnkey opportunity ready for immediate occupancy or rental. Situated on a quiet dead-end street, this property offers privacy while still being close to everything. Conveniently located just 3.8 miles to the beach and only 2.4 miles to Sarasota Memorial Hospital, with easy access to shopping, dining, and popular local restaurants, an ideal setup for strong and consistent rental demand. Whether you're looking to house hack, short- or long-term rent, or expand your portfolio, this fully upgraded duplex checks every box.

1802 Robinhood Street, Sarasota

2 Beds ⋅ 2 Baths ⋅ South Highland SubDv. ⋅ 34231 Zip Code

Welcome to this bright and inviting 2-bedroom, 2-bath Sarasota home offering 1,395 square feet of living space and a desirable split-bedroom floor plan. The interior features laminate flooring throughout and an updated kitchen with quartz countertops, decorative backsplash, and ample cabinetry. There is an inside laundry room and a separate living room that provides additional flexible living space, while the Florida room offers another versatile area for enjoying the Florida lifestyle. The spacious layout and abundant natural light create a comfortable atmosphere throughout the home. Conveniently located near downtown Sarasota, area dining, shopping, cultural attractions, and the beautiful Gulf beaches, this property offers an excellent opportunity to enjoy all that Sarasota has to offer. Bring your personal touches to make this home your own! All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyer advised to verify.

1840 Glengary Street, Sarasota

2 Beds ⋅ 2 Baths ⋅ South Highland SubDv. ⋅ 34231 Zip Code

Renovated 1150 sq. ft. beach cottage west of trail with open floorplan. Updated plumbing, new electric, new metal roof, AC 2020. Golf cart to all your favorite spots, Mortons, Libby's, Publix, EOS, Trader Joes, Walts Fish Market. 3 minute drive to Siesta Key bridge. Separate studio that can be used for office or in-law bedroom is not included in the listed square footage.

1837 Worrington Street, Sarasota

South Highland SubDv. ⋅ 34231 Zip Code

This beautiful rental property is located in the middle of Sarasota off Tamiami Trail. Walking distance to shopping and great restaurants. Close to Siesta Beach as well. The property is zoned RSF3. Monthly rental, each two bedroom , 2 bath unit epitomizes coastal living at its best. The attention to detail is everywhere. All the conveniences are included with this turnkey investment property. Beautiful outside area to relax in. Completely fenced in back yard oasis, independent from each side. The photos lend a view of this beautiful property, but go look at it you will immediately realize there is more to this great space. Located on the end of the street with no thru traffic makes this a perfect get away.

1805 Ivanhoe Street, Sarasota

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Lauralyn Kazimir

Lauralyn "Laurie" Kazimir

Laurie Kazimir is the Licensed Real Estate Broker and Co-Founder of Four Sails Real Estate, working alongside her husband and business partner, Christian Kazimir. Known for her strategic mindset, steady presence, and attention to detail, Laurie provides clarity and structure throughout complex real estate transactions. With experience spanning thousands of transactions across multiple markets, Laurie brings a thoughtful, analytical approach to both buyers and sellers. She is particularly skilled in pricing strategy, market positioning, contract structure, and guiding clients through high-stakes decisions with confidence and perspective. Laurie’s background includes primary residences, waterfront and coastal homes, second properties, and residential development opportunities. She plays a key role in evaluating financial considerations, long-term value, and overall transaction strategy—ensuring each deal is not only well-executed, but aligned with a client’s broader goals. Clients value her calm guidance, clear communication, and ability to manage complexity while keeping the process focused and grounded

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Christian Kazimir Four Sails Real Estate

Christian Kazimir

Christian Kazimir is a Broker Associate and Co-Founder of Four Sails Real Estate, working alongside his wife and business partner, Laurie Kazimir. Known for his energy, responsiveness, and deal-driven mindset, Christian is highly engaged throughout every stage of a transaction. With experience spanning thousands of real estate transactions across multiple markets, Christian brings momentum and focus to buyers and sellers navigating competitive environments. He is proactive, decisive, and deeply involved in negotiations—helping clients move forward efficiently while staying aligned with their goals. Christian’s background includes primary residences, waterfront and coastal homes, second properties, and land with residential development potential. He is especially skilled at identifying site opportunities, understanding buildability, and helping clients evaluate how a property can be developed or improved over time. Today, his work is focused on residential and lifestyle-driven properties along Florida’s Gulf Coast. Clients value his drive, availability, and commitment to pushing transactions forward while protecting their interests.

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