$1,625,091Average Value$779Average Price per Sq Ft36Homes 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 and earns an A from Niche. 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. The latter two are rated A-minus. 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.
View GreatSchools Rating Methodology
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Southside Demographics and Home Trends
On average, homes in Southside, Sarasota sell after 124 days on the market compared to the national average of 55 days. The median sale price for homes in Southside, Sarasota over the last 12 months is $1,787,500, up 12% from the median home sale price over the previous 12 months.
A private garden retreat in one of Sarasota’s most coveted West of Trail locations.** Nestled among lush tropical gardens and mature landscaping, 3424 Old Oak Drive is a captivating Sarasota bungalow where privacy, character, and effortless coastal living come together.From the moment you arrive, the home unfolds through a collection of intimate, inviting spaces. A charming front patio
Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,023 square feet of living space. Additional opportunity to add bathrooms with modification add-on with the builder. From the moment you enter, you'll be captivated by the open floor plan, pool view, and fantastic design. This dazzling property, boasts an open floor plan that features high ceilings,
Investor / Builder Alert! Exceptional WEST OF TRAIL opportunity in one of Sarasota’s desirable neighborhoods, Poinsettia Park. Located just steps from top-rated Southside Elementary School, this property offers incredible potential for redevelopment.The existing structure is a grandfathered duplex that is in very poor condition and best suited for teardown. The true value lies in the land — a
Welcome to this beautifully refreshed, single-story residence in Bay View Heights, one of Sarasota’s most coveted West of Trail neighborhoods. Set on a generous 15,625-square-foot lot, the 3,675-square-foot home offers a gracious open layout, refined updates, and exceptional potential to tailor the remaining spaces to your personal vision. The main living areas feature Mexican tile and wood
NEW CONSTRUCTION - Experience the pinnacle of Sarasota luxury in this newly completed, move-in-ready residence, ideally located within the City of Sarasota and attractively priced for today's market. Offering 5 bedrooms, a private den, 4.5 baths, and 4,106 square feet of thoughtfully designed living space, this exceptional home seamlessly blends contemporary elegance with relaxed coastal
Wonderful home! Was used as an AirBNB/VRBO for years and now it's available for you! Furniture negotiable. Walk to Southside Elementary school! Superior location in Sarasota, west of trail for under $550K. WOW. Plenty of parking available for you, guests, a trailer, etc. This is a charming 1950's cottage home that was wonderfully maintained. With a metal roof, you'll enjoy discounts on your
Between North Siesta Key and Oyster Bay, this coastal craftsman contemporary residence offers the leisure of a maintenance-free lifestyle in a desirable location. Visit nearby shopping and dining, or just a quick drive to Siesta Key Beach or downtown Sarasota. Positioned across from the community pool, the home offers easy-care landscaping complemented by a charming herb garden. Built of solid
Andrew TannerPREMIER SOTHEBY'S INTERNATIONAL REALTY
Welcome to your perfect coastal escape—an inviting cottage offering charm, comfort, and an ideal location away from the hustle and bustle of city life. Just a few miles from Siesta Key Beach, you’re only a short bike or golf cart ride from the world-famous quartz sand shores.This beautifully renovated two-bedroom, one-bath home has been thoughtfully updated from top to bottom. Inside, you’ll
Welcome to 1406 Tangier Way, a breathtaking expression of coastal contemporary luxury in San Remo Estates in Sarasota, where architectural excellence meets waterfront serenity. This 3,294 sq. ft. home is a seamless blend of sophistication, innovation, and artisanal craftsmanship, offering four bedrooms, three full baths, and unparalleled views of Sarasota Bay.Every detail has been
Welcome to 1959 Wisteria Street – a beautiful New Construction Single Story home, West of the Trail, that your clients will love!This just-completed modern coastal single story home is located West of the Trail in preferred Flood Zone X, offering elevated storm protection and convenient access to Southside Village, Downtown Sarasota and Siesta Key beaches.Designed and built with Majestik
Virtually Staged. Experience elevated coastal living in this nearly new Coastal Modern Farmhouse, thoughtfully built in 2025 by WG Homes with exceptional quality and craftsmanship. Constructed with solid block all the way up and topped with a standing-seam metal roof, this two-story residence offers five bedrooms, four-and-a-half baths, and a spacious, well-designed layout ideal for both everyday
Nestled in the heart of West of the Trail, this luxury single-story estate represents the pinnacle of modern living. Encompassing 3,262 square feet, the home features 4 bedrooms, 4 full bathrooms, and 2 half baths, all thoughtfully designed for both comfort and functionality. Set on an expansive 15,930-square-foot lot, the residence offers tranquility just moments from the shops and dining of
Find your sanctuary in this exquisite Allegra custom home, ideally located on one of the few non-throughfare streets in the highly coveted West of the Trail neighborhood. Serene and understated from the outside, the home opens to a breathtaking entry that reveals an extraordinary Great Room featuring soaring 21-foot beamed ceilings, a dramatic windowed rotunda, and an open-concept design bathed
The advertised rate of $8,681/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 24, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
The advertised rate of $7,133/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 24, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
Property Id: 2510072 2 bedroom, 2 bathroom open floor plan condo. Easy access to the community pool, designated parking and a fitness room. Fully furnished in coastal decor and minutes to Southside Village, Sarasota Memorial Hospital, Siesta Key Beach and Siesta Key Village.
The advertised rate of $4,468/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 23, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
Welcome to the Siesta Stunner! This 1950s pool home has been completely remodeled down to the studs w/ designer finishes & furnishings & high ceilings throughout. A short walk or bike ride will get you onto Siesta Key & the house is walkable to both Publix & the Siesta Key Mall! The space is light and bright thanks to the 10ft ceilings, abundant windows and southern exposure. Upon entering the
This gated beauty is IMPRESSIVE. It's easy to see why this home is an overall Parade of Homes winner! Five bedrooms and four and one half bathrooms of spectacular architecture filled with natural light. The great room has soaring beamed ceilings, built around a massive fireplace and open to the kitchen for easy family time and entertaining. The kitchen boasts solid wooden cabinetry topped with
Discover this beautifully renovated 2-bedroom, 2-bath corner unit located on the first floor in a private setting. Enjoy the convenience of assigned parking right outside your door and a spacious, light-filled interior featuring laminate flooring throughout. The eat-in kitchen showcases stainless steel appliances and ample storage, perfect for meal preparation and gatherings. The large living
GROUND FLOOR. NEW Carpet in bedrooms, tile in living room. Great Room floor plan with eat in kitchen. Kitchen is equipped with NEW APPLIANCES. Washer and dryer in this condo is a plus! Bathroom has granite counter and new fixtures. Addition access and sink area in master bedroom. Easy access to Siesta Key, Sarasota Memorial and Downtown Sarasota. Water sewer and basic cable included in the rent.
WEST OF THE TRAIL, BUILT IN 1926! Historic home near the north bridge going to Siesta Key. Cozy and quaint historical home minutes from the Siesta Key and Hillview. Step back in time in this cozy and relaxing home. Wonderful library. Enclosed garden/courtyard. Garage not available. Non smoking. No long term rentals available.
Enjoy this comfortable & spacious studio apartment located in wonderful Southside Village, recently renovated, 1 block to Sarasota Memorial Hospital. Brand new pool with large deck to enjoy the summer heat. Easy walk to so many wonderful restaurants and cute boutique stores. Siesta Key and Lido Key beaches 10 minutes away.
West of the Trail location with convenient access to downtown Sarasota and Siesta Key. Ground floor condo featuring a newly updated kitchen with new appliances and new carpet in the bedrooms. The enclosed lanai with vinyl windows opens directly to the parking area for easy access. Unit includes in-home washer and dryer and a Jack-and-Jill bathroom layout. Assigned parking space #56 located just
Escape the hustle and bustle while staying close to it all! Tucked away on a quiet dead end street, this charming 3 bedroom, 1 bathroom single family home sits on a spacious corner lot, offering the perfect balance of privacy, peace, and ultimate convenience. Whether you love world-class beaches or vibrant city life, you are ideally positioned just minutes away from the powdery sands of Siesta
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