Southside Houses for Sale with Private Pool

Welcome to this stunning 2021-built home in one of Sarasota’s most iconic and picturesque historic neighborhoods, Cherokee Park. Offering luxurious living with thoughtful design, this spacious residence of over 6000 square feet features a desirable first-floor primary suite with a decadent bathroom with soaking tub, oversized marble shower, and access to the covered porch for your morning coffee.

Samantha Callaway RE/MAX ALLIANCE GROUP

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

Marlin Yoder HARRY ROBBINS ASSOC INC

**** $15,000 PRICE REDUCTION ****Right Where You Want to Be—With a Pool That’s Ready to Dive Into! Att:Investors - ARBNB Income is $75,000This well-cared-for gem is all about location and lifestyle. New Roof in 2025 and New Pool Heater in 2024. Tucked into the private, dead-end street but just minutes to Siesta Key Beach, the Village, Sarasota Memorial, and loads of great local

Steven Weiss REDFIN CORPORATION

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

Brian Partie ENGEL + VOELKERS SARASOTA

Nestled on one of Sarasota's most sought-after streets, this classic brick residence on South Drive presents a rare opportunity to own a truly special property in the heart of Cherokee Park. Lovingly maintained by its original owner, the home rests on an exceptional, oversized lot - enhanced by deeded access from South Lodge Drive, adding a unique level of privacy and convenience. The timeless

Kelly Quigley MICHAEL SAUNDERS & COMPANY

One or more photo(s) has been virtually staged. 3576 San Remo Terrace – A Waterfront Masterpiece in SarasotaDiscover the pinnacle of coastal luxury at this exquisite estate, nestled in the highly sought after San Remo Estates. Offering the best views over Roberts Bay, this 6,091-square-foot residence seamlessly blends timeless elegance, modern sophistication, and unparalleled waterfront

Nazare Edelson COMPASS FLORIDA LLC

Stunning Mid Century Masterpiece, close to beach and walk to Southside Village. Featuring cypress inside and out. High ceilings and open spaces offer comfort and airiness, while the walls of glass sliders and windows fill the interior with natural lighting while showcasing gorgeous views of the lush landscaping. The expansive great room features floor-to-ceiling sliders and a wood-burning

Nora Johnson MICHAEL SAUNDERS & COMPANY

Welcome to 1915 Tulip Drive – a beautiful Single Story home you will love!This just completed Modern Coastal Single Story home is located West of the Trail in the preferred Zone X (unshaded) with elevated storm protection and easy access to Siesta Key beaches, Southside Village and Downtown Sarasota. Built strong and stylish by Majestik Homes, this 4 bedroom 4 bathroom residence

Alesia Stirp ALESIA DEANNA STIRP

Experience refined coastal living in this newly constructed luxury residence located in the heart of Sarasota. This thoughtfully designed home offers over 3,600 square feet of living space, creating the perfect blend of comfort, privacy, and functionality for family and guests alike. From the moment you enter through the grand courtyard entryway, you are greeted with soaring ceilings and elegant

Domanic Calamese KW COASTAL LIVING III

One or more photo(s) has been virtually staged. Drive under the serene canopy of oaks, and you will arrive at 1658 Bonita Lane, a brand-new custom construction, classic Spanish design inspired by the refined and timeless architecture of Palm Beach, Florida. Connected to nature with a quiet elegance, this residence features just under 4,000 square feet of 5 bedrooms, 4.5 baths and lots of

Sasha Rosin HORIZON REALTY INTERNATIONAL

Pre-Construction. To be built. Construction in progress. Situated West of the Trail, this exceptional estate represents the pinnacle of luxury living in Sarasota. Developed by M&J Pham Development, this residence is a masterpiece of innovative, forward-thinking design and flawless craftsmanship. This home is 4,765 square feet, with 5 bedrooms, 7 baths and 2 half baths. Inside, you'll discover an

Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

Under Construction. This stunning 2-story “Palonia IV Coastal” floor plan is one of the newest additions to the Allegra Homes collection of exquisite luxury residences and is located in the prestigious West of Trail area near Siesta Drive, your direct pathway to Siesta Key. The cornerstone of the Allegra Homes’ vision is a dedication to excellence in custom home building and providing the very

Karen Greco GRECO REAL ESTATE

One or more photo(s) has been virtually staged. Welcome to this stunning 2-story luxury home built by M&J Pham Development, featuring 5 bedrooms, 5 bathrooms, and 3,595 square feet of living space. From the moment you step inside, you'll be captivated by the open floor plan, high-end finishes, and fantastic design. The home features a modern and elegant kitchen with top-of-the-line Viking

Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

Welcome to 3319 S Osprey Avenue, a glourious 2023 newly built home offering 4 bedrooms, 4.5 bathrooms, and over 3,500 sq. ft. of refined living. Blending elegance and functionality, the home features a gourmet chef’s kitchen with quartz countertops, custom cabinetry, and premium Fulgor Milano appliances, an inviting first floor primary suite with spa-like bath and walk-in California Closet, and

Austin Morris PLATINUM PALM PROPERTIES

Modern luxury meets Florida beach house style in this impeccably renovated residence, located in the highly sought-after “West of the Trail” enclave — just minutes from Siesta Key’s world-renowned beaches and Downtown Sarasota’s cultural district.This designer 3-bedroom, 2-bath home offers nearly 1,900 square feet of refined interior space, thoughtfully reimagined for both elegant living

Ralf Michael Guensch EXP REALTY LLC

Welcome to 1856 Hyde Park Street, a delightful haven nestled in the heart of Sarasota’s Southside. This meticulously maintained three-bedroom, two + 1/2 bath home, complete with a dedicated office and an expansive flex space on the upper level, harmoniously blends comfort and convenience within one of the city's most coveted neighborhoods. On the main floor, you will discover a spacious primary

Terri Harrington VUE REALTY, LLC

Newer (2013) “West of Trail” offering with the perfect blend of charm and peace of mind — elevated 22 feet above sea level (X flood zone) with quick access to Siesta Key and zoned for the highly sought-after Southside Elementary. Thoughtfully designed for modern living, it features 3 bedrooms plus a flexible 4th bedroom, office, or gym, along with a versatile downstairs bonus room ideal for

Ryan Adamson COLDWELL BANKER REALTY

Welcome to one of Sarasota's most exclusive neighborhoods West of The Trail, where this charming home is nestled on an oversized double-wide lot measuring 12,500 sqft. This lot presents a unique opportunity for buyers looking to build their dream home, as it is one of the only corner lots available in the area. The existing home on the property is in need of demolition, making way for your vision

Vladislav Konatar KONA REALTY

**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

Jorge Zea BLUE LIGHTHOUSE REALTY INC

Experience the epitome of waterfront living in the sought-after San Remo neighborhood, ideally positioned at the tip of the peninsula. This exceptional 2022 custom-built residence offers sweeping panoramic views of Sarasota Bay and the city skyline, providing an unparalleled backdrop for everyday living. Boasting 4,359 square feet of thoughtfully designed living space, this home features 4

Barbara May MICHAEL SAUNDERS & COMPANY

Discover a rare, expansive property nestled in one of Sarasota’s most coveted “West of Trail” neighborhoods. This .35-acre property sits gracefully above special flood zones and offers convenient access to Downtown Sarasota, Siesta Key, and the prestigious Field Club. Located within the esteemed Southside Elementary School District, this home combines the quiet charm of the Granada neighborhood

Ryan Adamson COLDWELL BANKER REALTY

Rarely does an opportunity like this come to market, offering a piece of Old Florida on 2.1 lush acres and boasting breathtaking views of Sarasota Bay, Siesta Key, Bird Key, Ringling Bridge, and downtown Sarasota, this magnificent family compound features two custom-built Mid Century homes and a vacant lot, offering limitless possibilities. Designed to take advantage of the amazing views, the

Nora Johnson MICHAEL SAUNDERS & COMPANY

Located in the coveted West-of-Trail San Remo Estates, this rare double-lot, one-acre waterfront estate offers 200 feet of deep-water frontage with panoramic bay and Intracoastal views. Perfectly positioned near downtown Sarasota and Siesta Key, the property includes a protected boat basin for unmatched privacy and access.The gated 7,960 sq ft residence showcases modern Mediterranean

Charles & Gabe Buky COLDWELL BANKER REALTY

This newly remodeled West of the Trail home sits on a rare spring-fed lake on a private street. The home has been tastefully updated and offers 2 en-suite guest bedrooms with a split-plan master bedroom. The home is complete with high ceilings, an open floor plan, new paint, new luxury plank flooring, contemporary fixtures, some new vanities, and other new features. Beautiful sliding doors and

Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

One or more photo(s) has been virtually staged. Pre-Construction. To be built. ** LOT and CITY APPROVED PLANS.** Excellent Build/Development Opportunity **Experience the ultimate coastal lifestyle by building your custom dream home in Sarasota's coveted Granada Park. This is your chance to create a personal sanctuary just minutes from the pristine sands of Siesta Key Beach.This rare

Chad Fonder COLDWELL BANKER REALTY

Welcome to this stunning 3-story 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,

Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

The “St. Michael” is award-winning Allegra Homes’ 2025 fully furnished model home supremely located just south of downtown Sarasota’s cultural epicenter in the coveted West of Trail area where residents know first-hand what a wonderful community they live in. Prepare to be captivated by the seamless fusion of modern design, artful nuances, and stylish sophistication. Every detail has been curated

Karen Greco GRECO REAL ESTATE

Love where you live or rent it out! Now completed ( June 2025) perfect sun drenched vacation home or rental property.This beautiful new construction showcase home by Siesta Kay Properties has it all ! Peace of mind when it comes to hurricane proof estate! Solid masonry built thru two floors, impact windows and doors with heat and sound proof quadruple glass. Elevation 17.4 ft above the sea

Sylvia Nowicki PREFERRED SHORE LLC

3621 San Remo is complete and ready for occupancy, come and experience the epitome of luxury! Minutes from Siesta Key and Miles from Ordinary! Nestled on a quiet cul-de-sac west of Orange Avenue, this Florida Coastal masterpiece by Seaward Homes offers over 5300 sq. ft. of prime waterfront living. With a bayou stretching almost 400 feet wide, enjoy direct access to the breathtaking Sarasota Bay

Patrick Dipinto, III COLDWELL BANKER REALTY