South Highland Homes under $750,000

South Highland Homes under $750,000

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 choice for families, retirees, and anyone looking to embrace the vibrant Florida lifestyle. With its lush landscapes and friendly community, South Highland is more than just a place to live; it’s a place to thrive.

One of the standout features of South Highland is its diverse selection of homes, particularly those priced under $750,000. Whether you're searching for a cozy single-family home or a spacious residence with modern amenities, you'll find a variety of options that cater to different tastes and budgets. Many of these homes boast open floor plans, updated kitchens, and beautiful outdoor spaces perfect for entertaining or enjoying the serene Florida sunshine.

Living in South Highland means you’re just moments away from the stunning beaches of Sarasota, world-class dining, and vibrant shopping districts. The area is also known for its excellent schools and recreational facilities, making it an attractive option for families.

As you explore the community, you’ll discover a friendly atmosphere where neighbors become friends and lifelong memories are made. With its ideal location, affordable homes, and welcoming vibe, South Highland is the perfect place to call home. Come and experience the charm of South Sarasota living today!

Newest South Highland Homes under $750,000

1802 Robinhood Street, Sarasota

1802 Robinhood Street, Sarasota

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

Don't delay, 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

1840 Glengary Street, Sarasota

1840 Glengary 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

1837 Worrington Street, Sarasota

1837 Worrington 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

Start Your Search

Mikel Chaffee

Mike understands that buying and selling your home is one of, if not the biggest, financial decisions you will make. He knows first-hand the unparalleled value of hard work, dedication and exemplary service. With 13 homes sold in 2025 alone, putting him in the top percentile across the nation. Mike often works with his mom, Debi Chaffee Rose, as a mother-son team. Clients love their collaborative work and combined focus. Mike has a degree in management and operations, and for a number of years held his PGA Golf Certification. This experience gives him an intimate knowledge of many diverse golf and country club communities that make up the Florida lifestyle. 13 Years licensed as a Realtor, he is ready to put his experience to work, for you in any facet. Mike spends his free time with his beautiful wife Meghan, and their 4 Kids here in the town he was raised in, Bradenton Florida. They enjoy going and exploring the sunshine state together as a family.

Learn More

How much is your home worth?

Get instant property value now!