South Highland Real Estate

South Highland Real Estate

Welcome to South Highland, a hidden gem nestled in the heart of South Sarasota, Florida. This charming subdivision offers a perfect blend of tranquility and convenience, making it an ideal destination for families, retirees, and anyone looking to embrace the vibrant Florida lifestyle.

South Highland is characterized by its picturesque tree-lined streets, well-maintained homes, and a strong sense of community. With a variety of architectural styles, from cozy single-family homes to modern designs, there’s something for everyone in this delightful neighborhood. Residents enjoy spacious yards, perfect for outdoor gatherings or simply soaking up the Florida sun.

One of the standout features of South Highland is its prime location. Just a short drive away, you’ll find some of the most beautiful beaches in the world, including Siesta Key and Lido Key, renowned for their soft white sands and crystal-clear waters. For those who enjoy the outdoors, the area is dotted with parks and recreational facilities, offering ample opportunities for hiking, biking, and picnicking.

Families will appreciate the proximity to highly-rated schools and local amenities, including shopping centers, restaurants, and healthcare facilities. The vibrant arts and culture scene in nearby Sarasota, including theaters, galleries, and music venues, adds to the appeal of living in South Highland.

Whether you’re looking to settle down or invest in a vacation home, South Highland offers a welcoming community and a lifestyle that’s hard to resist. Come experience the charm and warmth of South Highland—your perfect slice of paradise awaits!

Newest Listings in South Highland

$650,000
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
$329,900
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
$611,000
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
$999,000
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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