South Sarasota Homes with Three+ Story Style

South Sarasota Homes with Three+ Story Style

Welcome to South Sarasota, a captivating gem nestled in the heart of Florida's stunning Gulf Coast. Known for its vibrant culture, lush landscapes, and sunny weather, South Sarasota offers an idyllic lifestyle for families, retirees, and everyone in between. This charming city boasts a rich tapestry of recreational opportunities, from pristine beaches to lush parks and scenic trails, ensuring that outdoor enthusiasts will never run out of things to do.

One of the most alluring features of South Sarasota is its diverse real estate market, particularly the stunning homes that rise three stories and beyond. These architectural marvels not only provide ample living space but also offer breathtaking views of the surrounding landscapes, including the shimmering waters of the Gulf and the lush greenery of nearby parks. Imagine waking up each morning to panoramic vistas and enjoying evening sunsets from your private balcony.

Homes in South Sarasota with three or more stories are designed for both comfort and luxury, featuring open floor plans, modern amenities, and spacious outdoor areas perfect for entertaining. Whether you’re looking for a family home or a vacation retreat, these properties provide the perfect blend of sophistication and relaxation.

In addition to the beautiful homes, South Sarasota is rich in cultural offerings, with art galleries, theaters, and fine dining options just a stone's throw away. With its warm climate, friendly community, and stunning real estate, South Sarasota is not just a place to live; it’s a place to thrive. Explore the possibilities and discover your dream home in this enchanting coastal paradise!

Newest South Sarasota Homes with Three+ Story Style

$1,200,000
5 Beds ⋅ 5 Baths ⋅ A4702315 MLS
**Rare Sarasota 4-Plex – No Flooding, Prime Location & Exceptional Investment Opportunity!** Don't miss this rare opportunity to acquire a well-located **4-unit multifamily property** in one of Sarasota's most desirable rental markets. A standout feature of this property is that **it has experienced no flooding**, providing added confidence for investors focused on long-term ownership. Ideally located just minutes from Siesta Key Beach, Gulf Gate, Downtown Sarasota, shopping, dining, hospitals, and major employers, this asset offers immediate rental income with excellent potential for future appreciation and rental growth. Whether you're adding to your portfolio, completing a 1031 exchange, or seeking a high-demand multifamily asset, this property offers the location and stability investors are looking for. With limited multifamily inventory available in Sarasota, opportunities like this are becoming increasingly scarce. **Schedule your private showing today—properties with this combination of location, income potential, and no flooding don't stay on the market for long.**

2741 Parma Street, South Sarasota
$1,795,000
6 Beds ⋅ 5 Baths ⋅ A4693403 MLS
You’ll love entertaining guests and embracing the tranquility of waterfront living in this one-of-a-kind classic Key West home on Philippi Creek Bayou. Enter through mahogany doors to soaring cathedral ceilings that fill the home with natural light and create an open, airy atmosphere. Expansive water views can be enjoyed in most rooms, while the outdoor deck provides the perfect setting to relax and take in stunning sunset skies. Inside, the Key West coral fireplace, luxury vinyl plank flooring and thoughtful architectural details create warmth and character throughout. The kitchen is designed for gathering and entertaining, featuring stainless steel appliances, a stainless-steel chef’s cooking area, quartz countertops and a wraparound bar that encourages memorable moments with family and friends. The enormous primary suite serves as a private retreat with its own water-view balcony, charming gas fireplace and bay windows. The spa-inspired en suite bath offers dual vanities and a relaxing spa tub. Dedicated office space provides flexibility for working from home or creating a quiet study area for the kids. Upstairs, you’ll find four bedrooms, a balcony and two full baths. The lower level features an expansive entertaining area ideal for a growing family, game room, gym or play space, along with a convenient pool bath for hosting guests. Outside, enjoy the private open pool area positioned at the water’s edge with long, peaceful canal views. The waterfront lifestyle continues with a kayak launch, Jet Ski floats and a newer composite boat dock with a 13,000-pound lift ready for boating adventures. Adding even more appeal for boating enthusiasts, the county is currently dredging the canal to further improve water access and navigation. The home has also been thoughtfully updated with a newer roof and freshly repainted interior and the property has been well maintained with no known storm-related damage or water intrusion. Just minutes from Philippi Shores Elementary and Riverview High School, this exceptional property is ideal for a growing family that loves the outdoors. A treasured Suncoast oasis where privacy, comfort and waterfront living come together beautifully.

5544 Dinah Lane, South Sarasota
$4,500,000
5 Beds ⋅ 6 Baths ⋅ A4693913 MLS
Welcome to Coucher du Soleil — French for "Sunset" — a magnificent gated waterfront estate styled after the grand French residences of New Orleans. Breathtaking views of Little Sarasota Bay, Siesta Key, and spectacular daily sunsets greet you from every room of this one-of-a-kind home. Impeccable craftsmanship is evident throughout, from the custom sapele mahogany front doors and hand-carved fireplace mantel to the handmade crown moldings and exotic sucupira hardwood floors. An elevator, exquisite lighting fixtures, exterior gas lanterns, and thoughtful hardware selections make this residence as functional as it is beautiful. The open-concept living and dining room flows seamlessly through numerous French doors onto an expansive covered balcony, also accessible from the guest suite and solarium. A custom library offers a tranquil retreat, while the entire top floor is dedicated to the primary suite, complete with a private office, morning kitchen, spacious dressing room, and private balcony with unsurpassed views. The carriage house provides an ideal in-law or guest suite with its own entrance, kitchen, bath, and balcony. Outdoors, enjoy the sprawling verandah overlooking the saltwater pool or head out on the water from your 50-foot composite dock with lift, electric, water, and sailboat access. Truly a one-of-a-kind Sarasota estate, do not miss this opportunity.

6438 Hollywood Boulevard, South Sarasota
$26,400,000
4 Beds ⋅ 6 Baths ⋅ A4673508 MLS
Welcome to Villa Meraviglia - A Home Beyond Imagination. An extraordinary Neo-Classical Italian Renaissance Estate set on 1.22 bayfront acres in Sarasota’s exclusive Oyster Bay Estates. Featuring 146 feet of pristine, direct frontage along the sparkling waters of Little Sarasota Bay, where sweeping panoramic views unfold, this walled and gated estate feels like a grand villa on the shores of Lake Como. A bold metallic gate, crowned with a striking Medusa head, sets the tone for the arrival experience, while two additional gold leafed gates - each equipped with electromagnetic openers - provide secure access, including a private entry to the neighboring yacht club. Encompassing more than 800 feet, the custom perimeter wall is more than a boundary: it’s a commanding architectural statement of luxury and artistry. Completely reimagined and expanded under the guidance of a classically trained Italian architect, the residence blends timeless European artistry with modern luxury. Inspired by Italy’s Villa del Balbianello and the iconic Casa Casuarina, the home showcases exquisite craftsmanship showcasing Venetian plaster walls, custom millwork gilded in 23-carat gold, hand-painted frescos, and pecky cypress ceilings. Spanning nearly 10,700 square feet of refined interiors, and over 4,000 square feet of air-conditioned space tailored for creativity and leisure, the home includes gracious entertaining areas, four ensuite bedrooms, four full and two half baths, and dual Clive Christian inspired kitchens designed for both family living and large-scale entertaining. Marvel at frescoed ceilings, stone-inlaid courtyards, and tranquil terraces that redefine elegance. Outside, lovely layered terraces and lush gardens frame peaceful, unobstructed bay views. A private dock with boat and jet-ski lifts anchors the waterfront lifestyle, while a resort style pool clad in shimmering mosaic tile, an octagonal pavilion, and a beautifully crafted summer kitchen elevate the outdoor experience to true luxury resort living. The sunken poolside kitchen is a beloved family gathering space ideal for relaxed al fresco dining. A large propane grill rises smoothly from its concealed appliance lift, while 100 year old Chicago reclaimed brick flooring, herringbone-pattern ceiling, and a beautiful maple wood dining set, create a warm, inviting ambiance. Thoughtfully curated seating areas capture breathtaking views in every direction, perfectly paired with spectacular year-round sunsets. Dive into luxury with the pool decking that elevates the iconic design of the Versace Property. Large, smooth marble stones imported directly from Italy weave a tapestry of geometric patterns that echo classic mythology. These intricate mosaics, true to Versace's legendary style, envelop the pool and its surroundings with a bold, artistic flair. A delicate Medusa mosaic graces the walkway, seamlessly connecting the pool area to the dock. Every element, from the imported Italian roof tiles to hand cast balustrades and hand painted frescos to the bespoke lighting and hardware reflects a deep commitment to authenticity, artistry, and permanence. Perfectly private yet ideally located near The Field Club and just minutes from Sarasota’s cultural scene, fine dining, and Gulf beaches, Villa Meraviglia stands as a rare masterpiece of design and craftsmanship. A world apart—where Old World elegance meets idyllic coastal living and every detail is a Living Gallery of beauty and craft.

1310 S Lake Shore Drive, South Sarasota
$169,000
A4666613 MLS ⋅ Phillippi Harbor Club BLDG.
Welcome to the exciting waterfront lifestyle at Phillippi Harbor Club in Sarasota! This rarely available 1st Level T-top height rack measures 28Lx9.5Wx17.3H. Fits Boats Up To: 28’ L x 8.5’ W x 15.3’ H, the tallest 28ft rack in the facility. Imagine the convenience of having your boat ready to go whenever you are, thanks to the friendly and efficient staff. Hurricane-protected building ensures that your boat stays safe and secure, while you enjoy peace of mind. With reasonable monthly fees, you can enjoy all the perks of the PHC without breaking the bank. But that's not all! Phillippi Harbor Club also offers valet services, discounted fuel, wash stations, shower room, service racks, full detailing services, and private assigned lockers. The location on protected waters with no bridges to the Intracoastal Waterway means that your boating adventures are just moments away. Nestled on the picturesque Philippi Creek, PHC offers more than just a place to keep your boat; it's a community of passionate boaters. This boat rack facility is approximately 4 minutes to the Intracoastal Waterway and about 20 minutes to the Gulf of Mexico.

1780 Phillippi Shores Drive Unit F1-44, South Sarasota
$579,000
3 Beds ⋅ 3 Baths ⋅ A4665433 MLS ⋅ 3 BLDG.
Beautiful luxury townhome with contemporary flair located only minutes from Siesta Key. This 3-story residence offers affordable luxury and maintenance-free living in a premier location on the shores of Phillippi Creek, where you are surrounded by 10 acres of stunning tropical foliage and landscaping. Rarely available, this is your chance to live in an open concept space with high ceilings, designer kitchen features, spectacular interior details and stylish bathroom fixtures. Upon entering this 3-bedroom, 3-bathroom home, you will fall in love with the bright, open floorplan featuring high-end finishes and an abundance of natural light. Enjoy relaxing on one of two lanais; one on the ground floor with outside access and another one upstairs with stunning views. There are stairs and a private elevator for your convenience as well as an oversized garage with plenty of room to store kayaks, golf clubs, beach chairs, fishing poles and more. The Phillippi Harbor Club Rackominium and Marina is right next door for your boating pleasures. There is also an onsite resort-style pool and kayak launch for active pursuits. Additional amenities include a clubhouse, dog park, fitness center and lighted boardwalk. You are minutes away from downtown Sarasota, fine dining, shopping, outdoor activities and the area’s famous beaches. Enjoy the best of Sarasota luxury living in the secluded, gated waterfront community of Phillippi Landings.

5560 Cannes Circle Unit 3-106, South Sarasota
$1,468,000
4 Beds ⋅ 4 Baths ⋅ A4654953 MLS
Live the Dream in Fishermen’s Bay – Private Bayfront Paradise with Deeded Boat Slip & Designer Touches. Welcome to a rare opportunity in the exclusive gated enclave of Fishermen’s Bay, a serene waterfront community of just 20 custom luxury homes, perfectly situated West of the Trail on the shimmering shores of Little Sarasota Bay. Tucked away at the end of a quiet cul-de-sac and nestled on a lush half-acre tropical estate, this Key West-style masterpiece offers over 3,200 square feet of elegant indoor living and expansive outdoor spaces designed for the ultimate Florida lifestyle. Enjoy Sarasota Bay views, water access, and a deeded boat slip, and private gate leading to Vamo Park for easy kayak launching just steps away. Crafted by renowned Yoder Construction, the home is a stunning blend of craftsmanship, comfort, and coastal sophistication. Step inside to discover wood floors, crown moldings, and stone countertops throughout. The chef’s kitchen is a dream, featuring a Viking range, Sub-Zero refrigerator, Fisher & Paykel dishwasher, quartz countertops ideal for entertaining. The main living and dining area opens through sets of French doors to a screened-in deck where you can relax and soak in the tranquil views of the bay and your private heated pool with sun shelf and 5-person spa (installed in 2020). Whether you’re enjoying your morning coffee or hosting sunset dinners, the setting is simply magical. The 3rd-floor master suite is a private sanctuary complete with a fireplace, dual walk-in closets, updated spa bath, and a private balcony offering serene water views. On the ground floor, a large bonus area opens to lush, Selby Garden-style landscaping with rambling paver walkways, and plenty of storage for kayaks and beach toys. Enjoy peace of mind with electric hurricane shutters, a 3-zone A/C system, engineered walls, and a sprinkler system fed by your own well. Additional Highlights: • Deeded boat slip with quick access to the Intracoastal • kayak launch • 2 fireplaces • Screened and covered porches for year-round enjoyment • 2-car garage with ample storage • Minutes to Siesta Key Beach, Pine View School, shopping, and dining This is more than a home—it’s a lifestyle. Discover the timeless charm of Old Florida with every modern luxury you could desire. Paradise is calling in Fishermen’s Bay!

8963 Fishermens Bay Drive, South Sarasota
Start Your Search