South Highland Real Estate

South Highland Real Estate

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

South Highland is characterized by its lush landscapes and friendly atmosphere, providing residents with a serene environment to call home. The meticulously maintained homes feature a variety of architectural styles, ensuring that there’s something to suit every taste. Whether you’re looking for a cozy single-family home or a spacious property with room to grow, South Highland has it all.

One of the standout features of this subdivision is its prime location. Residents enjoy easy access to some of the best amenities Sarasota has to offer. Just a short drive away, you’ll find pristine beaches, vibrant shopping districts, and a plethora of dining options that cater to every palate. Outdoor enthusiasts will appreciate the nearby parks and recreational facilities, perfect for weekend picnics, hiking, and family activities.

Education is also a top priority in South Highland, with several highly-rated schools within close proximity, ensuring that children receive a quality education. Community events and gatherings foster a sense of belonging, making it easy to connect with neighbors and create lasting friendships.

In South Highland, you’re not just buying a home; you’re investing in a lifestyle filled with warmth, community spirit, and the beauty of Florida living. Come discover the charm of South Highland, where your dream home awaits!

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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Bill Kilpatrick

Bill Kilpatrick is a licensed Florida Realtor® and real estate broker with more than 20 years of experience serving buyers, sellers, and investors throughout Lakeland, Tampa Bay, Winter Haven, and the greater Central Florida area. Since becoming licensed in 2002, he has built a reputation for strong negotiation skills, market expertise, and delivering exceptional service to hundreds of families across Florida. As the Managing Broker for the Keller Williams Realty Tampa Central office and the Keller Williams Realty Smart One office, Bill oversees more than 400 real estate agents and helps support offices that collectively generate billions of dollars in annual real estate sales volume. Bill also leads The Bill Kilpatrick Team at Keller Williams Realty, where his team has helped more than 800 families buy and sell homes throughout Central Florida. His experience spans luxury homes, residential sales, relocation, investment properties, and strategic pricing and marketing. Before real estate, Bill managed his family’s convenience store and gas station business, where he developed the customer service and leadership foundation that still drives his business today. Outside of real estate, Bill enjoys spending time with his wife Tiffany, his son Sebastian, and stepchildren Elle and Chase. He also enjoys boating, fishing, tennis, and snow skiing.

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