Welcome to 1711 Kenilworth Street, an exceptional opportunity to own a move-in-ready home in one of Sarasota’s most desirable West of the Trail neighborhoods. Located wit...
Virtually Staged. Tucked beneath a canopy of sweeping mature oaks in one of Sarasota's most coveted gated communities, this gracious two-story home strikes the perfect ba...
Imagine having your own private outdoor paradise designed for a relaxing life on the water. This custom designed Key West style residence in Southpointe Shores offers dee...
Located on approximately 200 feet of open Bay frontage in one of Sarasota's most prestigious neighborhoods, this remarkable property enjoys a postcard-worthy setting on m...
Modern architecture reaches an extraordinary new level at 1555 Eastbrook Drive, a newly completed 2025 estate offering nearly 4,000 square feet of sophisticated single-le...
Pre-Construction. To be built. Situated in San Remo Estates, one of Sarasota's most exclusive waterfront communities, this upcoming new construction home, designed and bu...
ATTENTION BOATERS!! Waterfront dream home – move-in ready! Just a quick (429 yard) boat ride to the ICW - no bridges - a straight shot to the water. Head out to the newly...
Welcome to a rare opportunity to own a spacious residence in the highly sought-after San Remo Estates, one of Sarasota's most desirable West of the Trail neighborhoods, i...
Experience the best of Sarasota living in the highly sought-after Indian Beach neighborhood, just minutes from Sarasota Bay, The Ringling Museum, Jungle Gardens and vibra...
Poised on one of the prettiest tree-lined West of Trail streets, this modern coastal residence offers the ideal blend of casual elegance, thoughtful design, and everyday ...
Fully renovated waterfront estate in Coral Cove, one of Sarasota’s most desirable West of Trail communities. Set on an elevated 0.59-acre corner lot directly across from ...
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 w...
This immaculate Sarasota Bay front estate is prominently positioned on the point of Harbor Drive. It embodies the pinnacle of luxury waterfront living, where timeless ar...
Virtually Staged. Exceptional West of Trail location! Nestled on a quiet cul-de-sac, this beautifully updated home offers the perfect blend of modern style and everyday c...
Welcome to this exceptional new construction, upgraded residence located West of Trail, featuring 5 bedrooms, 5 full bathrooms, and 3,640 square feet of thoughtfully cura...
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 b...
**This is the One!** Welcome to a beautifully renovated 3-bedroom, 2.5-bath pool home blending modern luxury with Sarasota charm in one of the area's most desirable locat...
Aggressively priced and ideally located West of the Trail just one block from Sarasota Bay, this spacious 4-bedroom, 4-bath residence offers exceptional value in one of ...
Build Your Dream Home on Sarasota Bay in Sapphire Shores! Set on an expansive 0.34-acre (14,665-sq.-ft.) waterfront lot, this property presents a rare opportunity to c...
Welcome to Indian Beach Sapphire Shores, one of Sarasota's most distinctive and sought-after neighborhoods. Known for its eclectic architecture, artistic character, matur...
Pre-Construction. To be built. Welcome to effortless coastal luxury in the coveted Harbor Acres neighborhood, where timeless glamour meets breezy, tropical elegance. The ...
Pre-Construction. To be built. Construction in progress, and opportunity for customizations. Situated West of the Trail, this exceptional estate represents the pinnacle o...
Virtually Staged. In the heart of Southside Village, this exceptional home offers one of Sarasota’s sought-after lifestyles. Just west of Tamiami Trail in Poinsettia Park...
Exceptional Sarasota bayfront homesite in Indian Beach/Sapphire Shores. A rare opportunity to build your custom waterfront home on one of Sarasota's most desirable bayfro...
One of the Last Remaining Legacy Properties on Golden Gate Point | Rare Trophy Ownership, Redevelopment & Strategic Hold Opportunity A truly rare offering in one of Saras...
This Spanish Mediterranean style home built in 1925 is nestled in the coveted "West of Trail" subdivision of DeSota Park in the South Poinsettia park Neighborhood just tw...
Located within Sarasota city limits in the Indian Beach/Sapphire Shores neighborhood, 2480 Alameda Ave offers a beautifully remodeled, move-in ready home with real flexib...
Experience modern luxury in this stunning new construction home located in Sarasota's highly sought-after West of Trail area. Offering 5 bedrooms, 5.5 bathrooms, and 4,16...
STEP BACK IN TIME and experience the charm of "OLD FLORIDA" in this beautifully preserved bungalow located west of North Tamiami Trail in the highly sought after Ringling...
Experience the timeless charm and distinctive elegance of this West of Trail luxury cottage, with modern finishes that remain true to its original allure, at 1829 Bougain...
Nestled within the exclusive, 11-home Ringling Point enclave of Sarasota's coveted Sapphire Shores neighborhood, this exceptional waterfront residence offers the perfect ...
A rare opportunity within the coveted West of Trail enclave of Pine Bay, this beautifully renovated residence is nestled on a quiet dead-end street near the historic Fiel...
Perfectly positioned on approximately 130 feet of deep sailboat water, this exceptional waterfront estate offers an extraordinary opportunity to experience the very best ...
Under Construction. Situated on a prized 1/3-acre homesite in the prestigious Harbor Acres community, this extraordinary custom residence by the award-winning team at All...
NEW CONSTRUCTION - Experience the pinnacle of Sarasota luxury in this newly completed, move-in-ready residence, ideally located within the City of Sarasota and attractive...
Sophisticated gated living just moments from the heart of downtown Sarasota. Evoking the timeless elegance of Palm Beach with the warmth of Old Florida charm, this except...
Ultra-Prime Development Opportunity on Golden Gate Point with Unmatched Versatility. This exceptional 0.496-acre site consists of 3 parcels totaling 21,600 sq. ft. and of...
In the sought-after, historic neighborhood of Indian Beach, this large corner lot offers a canvas to design and build your dream home. Spanning nearly 16,000 square feet ...
Charming 3BR/2BA Home on a Quiet Cul-de-Sac in a Highly Sought-After Sarasota Location! Welcome to this inviting and well-maintained 3-bedroom, 2-bathroom home perfect...
An extraordinary opportunity to build a world-class waterfront estate on Sarasota Bay. This rare direct bayfront vacant parcel at 2043 Alameda Way spans 38,009 SQFT with ...
Positioned along the sparkling waters of Sarasota Bay, this extraordinary 1.7 acres of direct bayfront property presents a rare opportunity to create one or two landmark ...
Outstanding opportunity to build your dream home in an ideal location. Situated on an 80’ x 110’ corner lot in one of the most desirable areas of Hudson Bayou, this prope...
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 ...
Imagine owning one of Sarasota Bay’s most exciting waterfront properties, where panoramic views, deep water access, and resort-style living create the kind of lifestyle p...
One or more photo(s) has been virtually staged. Investor’s dream in the heart of Sarasota! Welcome to 1613 Idle Lane, a rare opportunity to create your own custom coastal...
Renovated 1150 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, Mor...
Welcome to 1537 Siesta Drive—an exceptional custom coastal contemporary residence ideally positioned between Downtown Sarasota and world-renowned Siesta Key Beach. Built ...
Welcome to 7503 Starfish Drive in desirable Sarasota, Florida—an exceptional opportunity to own a slice of paradise just minutes from world-renowned Siesta Key Beach. Nes...
Just three homes in from the open waters of Little Sarasota Bay, this beautifully updated waterfront residence in Southpointe Shores offers a rare combination of location...
Investor / Builder Alert! Exceptional WEST OF TRAIL opportunity in one of Sarasota’s desirable neighborhoods, Poinsettia Park. Located just steps from top-rated Southside...

View our featured West of the Trail Listings above or create a search with your own criteria.
One of the hottest Sarasota Real Estate areas is this area known as West of the Trail. Located between Route 41 and the shoreline, this area features homes varying in architectural style and price with many located directly on the water overlooking Sarasota Bay. New construction homes also continue to come on the market as do the occasional land or lot for sale.
Living in this area affords the homeowner the true meaning of the Sarasota lifestyle. With its close proximity to downtown, the beaches of Siesta Key and Lido Key and all the cultural attractions of this beautiful city, the area West of the Trail is truly one of Sarasota's premier locations.
The homes located West of the Trail in Sarasota range in styles from tastefully appointed estates to mid-century modern to historical mission style bungalows, but all have one thing in common: they enjoy an unmatched location.
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Below are all current Sarasota West of the Trail home listings on the MLS. These are sorted from lowest price to highest and are updated every 15 minutes by the official Realtor®’s database.
For new construction opportunities, contact us. I can provide you with floorplans, upgrade lists, site plans, unadvertised leaseback and spec home opportunities as well.
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