$1,604,817Average Value$722Average Price per Sq Ft42Homes For Sale
Take your pick of housing, retail, dining and watersports
Architecturally diverse and filled with retail and dining options, Southside is an eclectic neighborhood that provides a unique slice of life on Sarasota’s waterfront. The neighborhood is anchored by Southside Village, a walkable commercial district that is home to an array of popular eateries and boutique shops. Additional convenience is provided by the neighborhood’s location – bordered on the west by Sarasota Bay and on the east by the buzzy Tamiami Trail corridor. Residents also enjoy proximity to a highly rated neighborhood elementary school with a rich history and the main campus of Sarasota Memorial Hospital.
Decorative Spanish-style homes highlight the architectural diversity
The neighborhood’s single-family housing is a colorful mix of shapes, sizes and styles. Large Spanish Mediterranean homes with easily recognizable terra cotta roofs and ornate facades stand out among the collection of homes that line Southside’s narrow, tree-lined streets. A handful of smaller Spanish Mission-style dwellings also can be found. In contrast, modern-style homes and smaller contemporary homes feature clean lines and muted colors. Additional architectural diversity is represented by Colonial Revival homes and their window-heavy asymmetrical facades, traditional Florida ranch-style homes on spacious lots and cozy, colorful shotgun-style homes. The majority of homes occupy a price range between $700,000 and $4 million, although the largest waterfront homes can list for as much as $12 million. Multi-family options include condominiums starting in the mid-$200,000s.
Historic homes line the streets of the Southside neighborhood in Sarasota.
Southside homes often have large old growth live oak trees covered in spanish moss.
Early Colonial style homes can be found sprinkled throughout the Southside neighborhood.
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Southside Village anchors a variety of retail and dining options
At the southern edge of the neighborhood along Tamiami Trail is a Publix-anchored shopping center. On the northern edge is the commercial heart of the neighborhood, Southside Village. The quaint district is home to Morton’s Market, a family owned community staple since 1969, and a variety of boutique shops that include Marmalade Salon and Beautiful You consignment store. Among the many eateries located at Southside Village are popular spots such as Libby’s Neighborhood Brasserie, Veronica Fish and Oyster, Origin Craft Beer & Pizza Café and Perq Coffee Bar. Located immediately north and also considered part of Southside Village is the Sarasota campus of Sarasota Memorial Hospital. Caddy corner to the hospital complex is the Sarasota Art Museum. Governed by the Ringling Board of Trustees, the world-renowned contemporary art museum advertises itself as a “platform for education, exposure and experimentation.” In addition to the dedicated exhibition space, the 15,000-square-foot facility also features an auditorium for educational and performing arts presentations and a sculpture courtyard.
Mortons Market in Southside Village has large assortments of fresh and organic foods.
The popular Veronica Fish and Oyster House is located in quaint Southside Village.
Sarasota Memorial Hospital is located at the north end of Southside on Tamiami Trail.
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Living on the waterfront makes for fun in the sun
In addition to the myriad fishing and boating opportunities afforded by living along Sarasota Bay in close proximity to the open waters of the Gulf of Mexico, residents also can access Siesta Key via Siesta Drive on the community’s south side. Just across the Siesta Key North Bridge is Nora Patterson Bay Island Park, a tranquil island green space known for the native birds that populate its shores. Nearby Bonita Park is part of a network of neighborhood green spaces featuring public art, including the nearly 100-year-old Granada Fountain at Bonita Park. The other network parks, all of which feature statuary amid peaceful residential settings, are San Remo Park, McClellan Park and Seminole Linear Park.
The bridge to Siesta Key is located at the South end of the Southside neighborhood in Sarasota.
Nora Paterson Bay Island Park is in the Southside neighborhood of Southside on the waterfront.
Red Rock Park is an excellent place to take a walk in the Southside neighborhood.
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Neighborhood elementary is historic and highly rated
Southside Elementary School, a historically significant institution, is centrally located within the community. Built in 1926 as part of the Florida Land Boom, the Mediterranean Revival building was added to the National Register of Historic Places in 1984. Southside today is among three highly rated schools that neighborhood students can attend, along with Brookside Middle and Sarasota High. All three schools are rated A-minus by Niche. The high school is home to the Sailor Circus Academy, which offers a hands-on program for aspiring performers.
Southside Elementary School in Sarasota is an A+ rated school.
Brookside Middle School in Southside Sarasota is a great school with an excellent teaching staff
Sarasota High School has an outstanding faculty and staff who provide a first-class education.
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Travel the coast with ease via the Tamiami Trail
Residents have quick and easy access to points along the Gulf Coast via the Tamiami Trail, which also serves as one of the region’s most-traveled roadways. Venice to the south and Bradenton to the north are both located about 15 miles away along the trail. Interstate 275 can be accessed in Bradenton for travel to nearby St. Petersburg and Tampa. Closer to home, Tamiami Trail also is dotted with bus stops, providing convenient public transportation for work commutes or travel throughout the city.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Southside, Sarasota sell after 147 days on the market compared to the national average of 52 days. The median sale price for homes in Southside, Sarasota over the last 12 months is $1,600,000, up 10% from the median home sale price over the previous 12 months.
This newer West of the Trail residence combines timeless sophistication with modern upgrades and a thoughtfully designed floor plan. The spacious great room flows effortlessly into the kitchen and dining areas, creating the perfect setting for both relaxed daily living and elegant entertaining. The chef’s kitchen is appointed with granite countertops, rich wood cabinetry, stainless steel
This is one of the best values for a newer 2008-built, 2,700 sq. ft. home in the prime West of Trail location. Thoughtfully upgraded throughout, the home features high ceilings and beautifully finished open floor plan with an oversized kitchen island with seating area. The main level boasts wood floors, high-end appliances and custom cabinetry. The 3 bedroom, 3 bathroom home features a large
**Motivated Seller** 2015 magnificently updated home located WEST OF THE TRAIL 5 bedroom/3.5 bathroom plus office.. This gated residence is ready for you to move in. As you enter you will be greeted with beautiful porcelain large format tiles throughout the bright open first floor plan with 10-foot ceilings. You will find Florida living at its best with large sliders connecting the screened pool
This one-of-a-kind, fully renovated residence is nestled in the heart of Sarasota’s historic McClellan Park—just steps from the bayfront, downtown, and Southside Village. Set on an elevated lot, the home experienced no flooding or storm damage during last year’s storms. Originally built by a builder as his personal home and reimagined in 2022 by the previous owner, an interior designer, the
Nearly complete and ready to impress! This fully renovated 4 bedroom, 3 full bath residence offers 2,379 sq. ft. of modern living in Sarasota’s premier neighborhood—San Remo Estates. Just a short walk to the North Siesta Key Bridge, this sought-after location combines an idyllic community setting with unmatched convenience.Designed with an open floor plan, the home showcases a brand-new
Introducing a rare opportunity in Poinsettia Park II, one of the most desirable enclaves within Sarasota’s coveted West of Trail community. Built in 2023 by Voigt Brothers, this single-level custom residence offers 4,550 square feet of elevated living on an oversized .38-acre lot, where timeless design meets modern innovation. From the moment you enter, soaring ceilings and a flawless Stage 5
Luxurious Fully Furnished, 3-Bedroom Home with Elevator in Gated Sarasota Community – Now Available for Rent! Short Term and Long Term rental options. AVAILABLE 10/1/25Discover your sanctuary in one of Sarasota’s most desirable enclaves—West of the Trail—where homes are rarely available. Nestled in the exclusive, gated community of Granada Park, this stunning 3-bedroom, 3 full-bath, and 2
Annual rental - unfurnished. One step away from Siesta Key, Sarasota Memorial and Hillview. West of the trail. Beautiful condo in Oasis on Osprey. 2 bedrooms, 2 bathrooms. All tiled for easy maintenance. Granite countertop in kitchen. Vacant and move-in ready. Sorry no pets. Application fee $75 + HOA application fee $100
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