South Sarasota Houses for Sale

Located West-of-Trail in one of Sarasota’s sought-after neighborhoods, Oyster Bay Estates, this stunning waterfront home is designed for those who appreciate breathtaking views and effortless entertaining. With a prime position on Sarasota Bay, this gated estate captures panoramic vistas of the city skyline, preserve and mangrove islands, and beyond. Blending timeless elegance with modern

Joel Schemmel PREMIER SOTHEBY'S INTERNATIONAL REALTY

Designed by esteemed architect John Potvin, this exceptional home combines elegance with casual tropical charm. Created with flexibility in mind, its three distinct structures—connected by covered lanais—provide privacy and grand spaces for socializing. Stone columns, metal pergolas, and lush foliage enhance the serene atmosphere, while a stucco perimeter wall ensures ultimate privacy,

Bridget Spiess PREFERRED SHORE LLC

One or more photo(s) has been virtually staged. Welcome to The Islamorada—a 2017-built coastal contemporary residence by Heritage Builders, ideally located in the highly sought-after Oyster Bay neighborhood of Sarasota. Blending expert craftsmanship with elegant design, this exceptional home offers the rare combination of luxury, privacy, and convenience—just moments from The Field Club, Siesta

Kelly Baldwin COLDWELL BANKER REALTY

TOTALLY UPDATED & ALL NEW FULLY FURNISHED (2024), NOT IMPACTED BY STORMS- SPACIOUS ELEGANCE, BEST BEACHES, ARTS, SHOPPING & FINE DINING, OVERSIZED CORNER LOT, CHEF’S KITCHEN. You will love where you live!! and treasure each moment in this Tropical Paradise surrounded by mature plush landscaping, a home inspired by the colors, and beauty of Florida’s Gulf Coast and the glamour of one of the most

Frank Chaviano KW COASTAL LIVING III

BEST BUY WEST OF TRAIL FOR NEW CONSTRUCTION. Why build when you can move right in. Nearly brand-new custom contemporary masterpiece, completed in December of 2024 and thoughtfully designed with luxurious finishes and top-tier functionality. Located just minutes from world-renowned Siesta Key Beach and vibrant downtown Sarasota, this 4-bedroom, 4.5-bathroom home with a den and bonus room spans

Ryan Carson RE/MAX ALLIANCE GROUP

Location, Condition, Price! WEST OF TRAILDiscover the ultimate blend of location, luxury, and lifestyle in this exquisite custom home, built in 2021 in the heart of it all . Set on an oversized 13,000+ sq. ft. lot in a peaceful, tree-lined cul-de-sac, this architectural masterpiece offers privacy and tranquility.Boasting four bedrooms, including two owner’s suites, and 3.5 baths, this

Inbal August DOUGLAS ELLIMAN

Welcome to this beautifully updated 4-bedroom, 3.5-bathroom residence nestled in the highly sought-after Oyster Bay area. Perfectly positioned West of the Trail, outside of a flood zone, this charming residence offers the ideal blend of comfort, style, and convenience. Step inside to find a spacious and flexible floor plan designed for modern living, including two dedicated office spaces,

Ryan Carson RE/MAX ALLIANCE GROUP

Nestled among towering oaks and mature landscaping sits this mid-century modern home. On an oversized lot with a pavered circular driveway, a fully fenced yard that is perfect for pets, and a side entry oversized 2 car garage. This updated home exudes both charm and sophistication. Boasting 9 sets of sliding glass doors, the views of the tropical gardens and outdoors blend seamlessly with indoor

Janis Collier MICHAEL SAUNDERS & COMPANY

This exceptional custom-built residence with separate guest quarters is located in the highly sought-after Oyster Bay Estates on over half an acre of land and offers a private, luxurious lifestyle and a unique blend of modern upgrades. Situated in the desirable ‘West of Trail’ community near Sarasota Bay, the main house features 10-12 ft ceilings, travertine flooring, and surround sound

Ann Martin MICHAEL SAUNDERS & COMPANY

This spacious Sarasota home offers the perfect blend of location, layout, and livability, making it an exceptional choice for doctors and families. Doctors will appreciate the convenient proximity to Sarasota Memorial Hospital, while families benefit from easy access to top-rated schools such as Southside Elementary, Sarasota High, and Riverview High. Set on a half-acre lot along a spring-fed

Peter G. Laughlin PREMIER SOTHEBY'S INTERNATIONAL REALTY

Discover unparalleled luxury in this exceptional waterfront estate, ideally located West of the Trail, offering direct bay access with no bridges. This stunning home features four spacious bedrooms and four beautifully appointed bathrooms, along with a private cabana that includes a bedroom and half bath, providing the perfect guest retreat. Designed for seamless entertaining, the home boasts a

Denise Mei MICHAEL SAUNDERS & COMPANY

Pre-Construction. To be built. Modern Contemporary Farmhouse Style on just Over Half an Acre!This brand-new home is to be built and offers the perfect blend of clean and modern design with the warmth and charm of contemporary farmhouse style. Featuring high-end finishes, open concept living, and thoughtfully designed spaces, this is your chance to personalize your dream home from the ground up.

Samantha Jennen PREFERRED SHORE LLC

Location, updates, and freedom — all in one property! Situated in Flood Zone X (no flood insurance required), this beautifully updated 3-bedroom, 2-bath home offers both comfort and convenience just minutes from Siesta Key Beach, US-41, Sarasota Memorial Hospital, shopping, dining, and vibrant downtown Sarasota. No Hoa, No CDD. The home features a spacious primary suite complete with a

Travis Matthews PREFERRED SHORE LLC

Welcome to 4074 Redbird Cir—a home that has a LOT of personality and curb appeal. This stunning 4-bedroom, 2.5-bath has been completely renovated. This beautiful home combines classic farmhouse charm with the ease and sophistication of modern living. Nestled on an expansive third of an acre corner lot in one of Sarasota’s most desirable neighborhoods, this stunning home is a masterclass in light,

Desiree Doggett NEXTHOME EXCELLENCE

Welcome to 2320 James Lane—A private Sarasota escape with designer touches and resort-style outdoor living! Nestled on a peaceful street just minutes from the heart of Sarasota, this beautifully updated residence is a rare blend of elegant finishes, thoughtful design, and true indoor-outdoor Florida living. From the moment you arrive, you'll feel the warmth and charm that make this property stand

Clifford Howell KELLER WILLIAMS TAMPA PROP.

Escape to your own tropical paradise in this stunning bungalow style single-story home nestled in the heart of Sarasota, FL! This 3-bedroom, 2-bath coastal-inspired gem is enveloped by a breathtaking 360-degree garden, bursting with vibrant Floridian foliage—think lush palms, colorful hibiscus, and majestic oaks that create a secluded, verdant oasis. A wood privacy fence ensures the property

Joe Sussingham SERHANT

Stunning Beachy Retreat with Pool! No HOA & Prime Sarasota Location!Looking for a home near the beaches, shopping, dining, and downtown Sarasota? Look no further! Nestled in a private cul-de-sac with no HOA, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of style, comfort, and convenience.Inside, you'll find vaulted wood plank ceilings with skylights that flood the home

Nikola Zafirovski CENTURY 21 BEGGINS ENTERPRISES

Sited on nearly 1 acre of desirable, elevated land along the serene shores of Phillippi Creek, this single-family pool home presents a rare opportunity to own a private waterfront retreat in the heart of Sarasota. Tucked away in a quiet, established neighborhood and built at 16 ft above sea level in the X flood zone with great proximity to US 41 and amenities, this 4-bedroom, 3.5-bathroom plus

Lenore Treiman MICHAEL SAUNDERS & COMPANY

Welcome to this beautifully updated, mid-century bungalow, where vintage Florida charm meets modern convenience in the heart of Sarasota, Florida! This meticulously maintained home features stunning original terrazzo floors—recently cleaned and polished to showcase their timeless appeal. The fully renovated kitchen is a true highlight, offering crisp shaker cabinets, gleaming granite countertops,

Julie Willett NEXTHOME BEACH TO BAY

Spacious & Nicely Renovated 3-Bedroom Home on Large Double Lot – Prime Location & New Roof!Discover this beautifully renovated home on a rare double lot, offering plenty of space and endless possibilities. Featuring 3 bedrooms, including one that could be used as a large flex space, this home is designed for comfort and versatility.Enjoy Florida living at its best with a bright and airy combined

Stacy Lyn Carlin PREFERRED SHORE LLC

One or more photo(s) has been virtually staged. We are so excited to offer this beautiful four-bedroom, fully remodeled home in the heart of South Sarasota, just minutes to Siesta Key and Turtle Beach. Featuring a lovely mature lot with an inground sprinkler system fed by a private well, on approximately 1/4 acre. With a seamless blend of comfort and style, meticulously designed with indoor

Rachel Tritschler RE/MAX ALLIANCE GROUP

3 bedroom pool home with attached 2/1 with full kitchen. 2 miles to Siesta Key, easy commute to downtown Sarasota. Has a screened in pool, storage shed, fenced in yard and generator. Offered fully furnished! Excellent rental income opportunity. Rent both , live in one /rent the other or make it your large single family home.

Terry Dorrity INTEGRITY INVESTMENTS REALTY

Located in one of Sarasota’s most prominent neighborhoods, this property enjoys a postcard-like setting featuring wide-open bay views on over an acre of land. Positioned in close proximity to The Field Club, the property enjoys approximately 200 feet of natural shoreline, a 150+ ft. long boat dock which is being restored, and a beautiful backyard with mature landscaping. There are Bay views from

Kim Ogilvie MICHAEL SAUNDERS & COMPANY

$70,000 Price Reduction! Own More For Less! Why go elsewhere when you can move right into a fully upgraded, better-than-new masterpiece designed for the way you really live? Welcome to this stunning 4-bedroom, 2.5-bath home by Majestik Homes—a builder known for blending timeless craftsmanship with contemporary flair. Set on a larger, meticulously landscaped corner lot, this residence offers

Derek Patti NEXTHOME EXCELLENCE

Welcome to this stunning single-story home in the heart of Sarasota with numerous updates. This inviting residence boasts 3-bedrooms, 2 baths plus office and bonus room. The office with it's own separate entrance is directly off of the master, has multiple closets and could conveniently serve as a nursery. Large bonus room includes a closet and Murphy bed, perfectly combined as a recreation room

Joseph Stephens ONE STEP AHEAD REALTY INC

A testament to timeless elegance and the tropical charm of coastal living, securely situated at or above base flood elevation and not impacted by the recent storms, this exceptional Bayfront estate rests on nearly one acre, boasting 180 feet of water frontage and effective year built 2016. Fully renovated and expanded in 2017, it offers breathtaking, uninterrupted views of Roberts Bay and the

Michael Hays MICHAEL SAUNDERS & COMPANY

One or more photo(s) has been virtually staged. Your Sarasota Dream Home Awaits: PRIME LOCATION Modern Elegance Near Siesta Key & Downtown! Welcome to your beautiful move-in ready home in a highly sought-after Sarasota neighborhood! Built in 2017, this stunning 4-bedroom, 3.5-bath residence offers the perfect blend of modern living and everyday comfort for those seeking sophisticated design,

Kimberly VanHerwynen KELLER WILLIAMS ST PETE REALTY

Renovated 1100 sq. ft. beach cottage west of trail with open floorplan. Updated plumbing, new electric, new metal roof, AC 2020. Golf cart to all your favorite spots, Mortons, Libby's, Publix, LA Fitness, Trader Joes, Walts Fish Market. 3 minute drive to Siesta Key bridge. Separate studio that can be used for office or in-law bedroom is not included in the listed square footage.

Jonathan Minerick HOMECOIN.COM

Conveniently located West of the Trail, this 5-bedroom, 4.5 bath, 3619 sq foot residence was recently upgraded in 2022/2023 to meet the needs of the most discerning buyer. Featuring a center island and top-of-the-line appliances by Wolf, SubZero and Cove, the kitchen flows seamlessly to the living area where you are greeted by sliding glass doors that overlooks a backyard oasis. The heated pool

Victoria Turner MICHAEL SAUNDERS & COMPANY

Step into a stunning, double-story contemporary masterpiece, offering 4 spacious bedrooms and 4.5 impeccably designed bathrooms. Crafted with meticulous attention to detail, this home features sleek block walls and double floors, each boasting an impressive 10-foot ceiling height. The hurricane-proof windows ensure both safety and tranquility, while the luxury vinyl flooring flows seamlessly

Olga Smith IMPERIAL PROPERTY GROUP LLC

Now completed. Another masterpiece by Majestik Homes, Sarasota's Premier Homebuilder. Welcome to 2249 Oak Terrace, a modern gem thoughtfully designed for those who value style, comfort, and resilience. Enjoy easy access to grocery stores, restaurants, scenic trail parks, and top-rated schools.Impressive 10' ceilings and 9' impact-rated windows bring in tons of natural light while

Alesia Stirp ALESIA DEANNA STIRP

A One-of-a-Kind Modern Estate – Introducing 1555 Eastbrook Dr, an architectural triumph where modern elegance, high-performance design, and luxurious livability converge. This custom-built, single-story residence is a bold statement in style, showcasing a flat roofline, expansive open floor plan, and soaring ceilings that amplify light, volume, and contemporary sophistication. This smart home is

Daniel Dabrowski DALTON WADE INC

Stunning new construction by award-winning Trinity Custom Homes. Discover luxury and innovation in this remarkable four-bedroom-plus-den, 5.5-bath West of Trail home. This custom-designed residence showcases superior craftsmanship, offering a sophisticated blend of modern design and top-tier functionality. Every detail has been meticulously planned, from the gourmet kitchen, which features

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

Under Construction. The Windemere II is an extraordinary luxury custom home meticulously crafted by Heritage Builders. This coastal contemporary residence with clean lines is situated on a very rare West-of-Trail lakefront estate home site. The exquisite two-level residence redefines custom home living, flawlessly blending elegance, sophistication and comfort. As you step in the grand foyer, you

Sara Boudarga HB REALTY GROUP INC.

Under Construction. : Introducing The Sanibel II by Heritage Builders a distinguished estate-style custom home that exemplifies elegant design and fine craftsmanship. Situated on nearly half an acre in the coveted Oyster Bay area West of the Trail, this single-level 3,862 sq. ft. residence offers four bedrooms, four and a half baths, and an unmatched blend of sophistication and comfort. From the

Sara Boudarga HB REALTY GROUP INC.

Under Construction. Under ConstructionA Unique Opportunity to own a Nutter Custom Construction Home, Designed on an Expansive Lot in Field Club Estates. This 4000 sf, 1-Story home takes advantage of its location by offering a spacious layout while keeping a secluded, private feel. Upon entering the property, you will notice the gorgeous palms and mature vegetation, 3 car side load garage and

Terence Nutter NCC PROPERTIES LLC

Pre-Construction. To be built. Step into the pinnacle of modern luxury with this stunning home located in the prestigious Oyster Bay Estates built by The Holliday Group. Nestled on a generous 18,991 sq ft lot with 71 feet of serene lake frontage, this modern oasis offers a blend of style, comfort, and sophistication. This home is not located in a flood zone and everything is on one level (no

Ryan Carson RE/MAX ALLIANCE GROUP

One or more photo(s) has been virtually staged. Under Construction. Welcome to a life of unparalleled luxury in an unrivaled location, where every detail has been meticulously crafted to create a haven of sophistication and comfort. Set within Oyster Bay, just moments from downtown Sarasota and world-renowned beaches, this masterpiece of design and craftsmanship is currently under construction,

Ryan Ackerman COLDWELL BANKER REALTY