4-Bedroom Houses for Sale in Southside with Private Pool

Motivated Seller – bring your offers! Just Added a $150K Custom Pool & Spa! Live the ultimate Florida lifestyle in this luxury new construction home (2023) by acclaimed builder M&J Pham Development, located between Siesta Key and Downtown Sarasota in the highly sought-after Southside School District. This elegant 4-bedroom, 4.5-bathroom residence blends upscale design with modern comfort and

Laura Rode KELLER WILLIAMS ON THE WATER S

Welcome to this rarely available Cape Cod-style residence, a masterfully renovated home situated on an expansive 20,000 sq. ft. lot in Sarasota’s prestigious Cherokee Park. Perched 23 feet above sea level and nestled on a quiet extra wide tree-lined street with sidewalks in one of the area’s most coveted West of Trail neighborhoods in the top-rated Southside school district. This 4-bedroom, 3

Lenore Treiman MICHAEL SAUNDERS & COMPANY

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

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

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

Welcome to an exquisite 3,613 sqft New Construction home nestled near a highly coveted and sought after location in Sarasota. Built by M&J Pham Development, this residence offers unparalleled combination of complete sophistication and designed for livable luxury. The warm and inviting palette is both trend-forward and timeless. As you enter, you will be greeted by a soaring 2 story great room

Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

GREAT LOCATION – WEST OF THE TRAIL! This dazzling custom-built, single-level pool home is situated in the desirable "flower streets”, west of the trail in Sarasota. Featuring a new, 3 color clay tile roof and Mediterranean style design this home has timeless style combined with modern luxury. Upon entering the double doors of this one-story retreat, you will notice the open layout and quality

Jan Jordan BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

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 RE/MAX ALLIANCE GROUP

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

Welcome to this beautifully designed pool home in the West of the Trail Sarasota neighborhood. This four-bedroom, three full and two-half-bath residence offers 2,617 square feet under air, 4,188 total, and blends modern style and comfort, with an unbeatable location. Built in 2013, this move-in-ready home features soaring ceilings, crown molding, engineered hardwood floors throughout,

Elizabeth Snyder PREMIER SOTHEBY'S INTERNATIONAL REALTY

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

New Construction by Majestik HomesMove-In Ready | Easy to ShowWelcome to 1559 Bay Road, a new home by Majestik Homes, ideally located West of the Trail in Sarasota’s coveted Granada neighborhood. Just 4.6 miles from Siesta Beach, 6.0 miles from Lido Beach, and only 1.9 miles from Sarasota Memorial Hospital, this prime address places you near upscale restaurants, artisan deli

Alesia Stirp ALESIA DEANNA STIRP

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