RARE WEST OF THE TRAIL OPPORTUNITY – TURNKEY FURNISHED & READY FOR IMMEDIATE INVESTMENT! Location, location, location! Discover this beautifully updated, turnkey furni...
Under Construction. Why choose between your perfect sanctuary and stunning sunsets when you can have both. Every evening, the horizon performs a breathtaking masterpiece ...
**Prime 2.73-Acre Development Site in the Waterside neighborhood in Lakewood Ranch, Sarasota** An exceptional opportunity in the heart of the Waterside/Lakewood Ranch ...
LOCATED WEST OF THE TRAIL IN A TROPICAL PARADISE. A charming 3-Bedroom, 2-Bath Cottage in Indian Beach–Sapphire Shores. Discover this adorable Cottage in Indian Beach...
Mid-Century Modern Gem with Pool, Character & Endless Potential in Indian Beach Sapphire Shores. Bring your vision and creativity to this mid-century modern home in th...
An exceptional opportunity to own a rare waterfront homesite in Cherokee Park, one of Sarasota’s most established neighborhoods. Encompassing an expansive 20,215 square f...
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...
Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,032 square feet of living space. Additional opportunity to add bathrooms w...
Impeccably maintained and thoughtfully designed, this custom-built John Cannon home offers an inviting blend of timeless elegance, spacious interiors, and relaxed Florida...
Introducing “Gatsby Manor,” set along Hillview Drive, one of Sarasota’s most coveted bayfront addresses, often compared to Port Royal for its exclusivity and waterfront l...
Pre-Construction. To be built. Introducing an exceptional new custom residence that redefines contemporary luxury in Sarasota's coveted West of Trail neighborhood. Though...
Under Construction. Exceptional New Construction | Sarasota Bayfront Living. Experience extraordinary waterfront living in this stunning new-construction residence, perfe...
Virtually Staged. Welcome to Cleary Cottage, a charming 1935 bungalow nestled in the highly sought-after Hudson Bayou neighborhood, West of Trail in the heart of Sarasota...
Discover the ultimate West-of-Trail canvas at 1605 N Lake Shore Drive, an extraordinary opportunity to design a custom architectural masterpiece in Sarasota’s prestigious...
Distinctive Architecture. Space to Unwind. West of Trail. Set on a tropically landscaped half-acre corner lot on a private dead-end street off Camino Real, this custom h...
Discover an exceptional opportunity in the Landings, one of Sarasota's most sought-after communities, ideally situated West of the Trail. Custom-built and lovingly mainta...
A storybook setting for your Sarasota dream home. As Sarasota continues to grow northward, this fabled little neighborhood becomes all the more desirable. Tucked along a ...
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...
House never flooded, including during Hurricanes Milton and Helene, and protected by a generator! Built as a solid concrete structure on concrete pilings, this home was e...
Virtually Staged. LOWEST-PRICED NEW CONSTRUCTION WEST OF TRAIL. Completed in 2026 and ideally located close to Siesta Key and downtown Sarasota, this modern 4-bedroom plu...
Pre-Construction. To be built. Completion anticipated in a few months. Situated West of the Trail, this exceptional estate represents the pinnacle of luxury living in Sar...
Eagles Point Villa | The Landings, West of the Trail Tucked behind The Landings’ 24 hour manned gatehouse in the coveted area West of the Trail, this Eagles Point villa ...
LOWEST-PRICED NEW CONSTRUCTION WEST OF TRAIL. Completed in 2026 and ideally located close to Siesta Key and downtown Sarasota, this modern 4-bedroom plus den, 4.5-bath re...
Imagine beginning your morning with coffee overlooking the water, spending the afternoon exploring Sarasota Bay by boat, and returning home for an evening beside the pool...
Excellent location in Sarasota's Southside Village. This beautifully maintained 3-bedroom, 2.5-bathroom residence offers an excellent combination of thoughtful design, pr...
A TRUE TRANSFORMATION in Sarasota’s coveted Indian Beach/Sapphire Shores neighborhood, 780 Indian Beach Circle has undergone a comprehensive, permitted reconstruction ext...
Welcome to this charming single-family residence located in the highly sought-after Granada neighborhood. Step inside to find a welcoming layout complete high ceilings, o...
Welcome to 844 Patterson Drive, a charming coastal retreat tucked away in Sarasota's beautiful Indian Beach–Sapphire Shores neighborhood! Situated on a spacious corner lo...
Virtually Staged. Step into the timeless character and charm of this beautiful 1940s home in highly sought-after Avondale, ideally situated West of the Trail on a corner ...
Downtown Waterfront Living with Direct Access to Sarasota Bay and the Gulf of Mexico. A rare opportunity to own a deeded boat slip with a 10,000-pound lift, accommodating...
Welcome to this immaculate, move-in ready Sarasota estate on a quiet, no-outlet cul-de-sac west of the Trail, just minutes from both the world-famous beaches of Siesta Ke...
Pre-Construction. To be built. To be complete in 3-4 months. Situated in San Remo Estates, one of Sarasota's most exclusive waterfront communities, this upcoming new cons...
Less than 2 miles from world-famous Siesta Key, this 4-bedroom, 3-bath, 3-car garage pool home in Aqualane Estates offers a rare combination of waterfront living, bold de...
Location, Location, Location! Ready to build, bring your architect and builder to this wonderful and oversized lot with an additional access easement to Bay Shore Rd. Sit...
Welcome to 1406 Tangier Way, a breathtaking expression of coastal contemporary luxury in San Remo Estates in Sarasota, where architectural excellence meets waterfront ser...
PRIME SARASOTA CITY LAND — CLOSE TO WATER & OUT OF FLOOD ZONE! Outstanding build opportunity. This 8,200 sq. ft. lot sits just steps from Sarasota Bay with 2-story design...
Discover an exquisite blend of Old-World charm and modern luxury in this custom Mediterranean jewel. Located in the heart of Sarasota’s Historic Museum Area in Sapphire S...
The West of Trail BEST BUY!! Located between Osprey Avenue and Orange Avenue. Rarely will you find a 2500+ square foot cement block home on an oversized corner lot (100' ...
*VIRTUALLY STAGED* Desirable West of the Trail location in the sought-after Southside school district! Welcome to 1881 Orchid Street, a beautifully updated 3-bedroom, 2-...
Welcome to Mandarin Park, one of Sarasota’s most desirable gated communities, where beautiful homes, privacy, and an unbeatable location come together in the heart of the...
Built in 1910, this original kit house offers a rare opportunity to own a remarkable piece of Sarasota history. Once ordered by mail from, the residence has been extensiv...
This is the one * LOCATED IN THE HIGHLY DESIRABLE AQUALANE ESTATES, JUST A MILE FROM WORLD FAMOUS SIESTA KEY BEACH, THIS CUSTOM HOME OFFERS AN INCREDIBLE OPPORTUNITY TO O...
Wonderful home! Was used as an AirBNB/VRBO for years and now it's available for you! Furniture negotiable. Walk to Southside Elementary school! Superior location in S...
Welcome to this stunning BRAND-NEW CONSTRUCTION home in Sarasota, offering 2,678 square feet of beautifully designed living space with 4 bedrooms, 4.5 bathrooms, a privat...
Nestled within the desirable West of Trail Southpointe Shores Community, this home benefits from top-rated school zones and a serene, upscale waterfront atmosphere. This ...
Wake up to the salt air. This gorgeous updated Indian Beach home is perfectly situated close to downtown, west of Trail/west of Bayshore. Take a 4-minute walk to see the ...
NOW PRICED BELOW RECENT APPRAISAL. Behind a private gate and beneath a canopy of tropical foliage, 1621 Bay Point Court offers a secluded waterfront retreat just moments ...
Rarely available in Cherokee Park, widely regarded as one of Sarasota’s most desirable West of Trail neighborhoods, 1722 North Drive presents an extraordinary opportunity...
Build something extraordinary in Sapphire Shores, one of Sarasota's most coveted bayfront neighborhoods, where canopied streets, custom architecture and the open water of...
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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.
Our website provides property information on listings in real time. That means as soon as they are entered into the the official Realtor®’s database, any search you've created on our website will be updated with notification. All information is updated every 15 minutes so you can be sure to have the most recent information available.
Customize your search for real estate throughout Sarasota and Manatee Counties in the Advanced Search. You can save searches, and get daily email alerts of new listings, price changes, sold data, and also perform market reports.
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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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