Below are the current West of the Trail Sarasota real estate listings. Our website allows you to easily search through the 147 single-family homes for sale priced from $384,900 to $18,950,000. Our database is updated throughout the day from the Multiple Listing Service (MLS). BuySarasota.com is committed to providing you with the most up-to-date and freshest local listings on the Internet.
Allen Real Estate Services, Inc. is a full service, boutique real estate brokerage offering specialized service and expertise to customers selling and buying real estate in Sarasota. To learn more about any of these properties or receive email updates when new listings hit the market, simply give us a call at 941-544-6467 or send us an email. We are here to help!
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| Total Listings: | 147 |
| Average Price: | $2,881,643 |
| Highest Price: | $18,950,000 |
| Lowest Price: | $384,900 |
| Average Size: | 3,134 ft² |
| Average Price Per Square Foot: | $770 per ft² |
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World-renowned As Florida’s Cultural Coast, Sarasota’s Heritage Of Culture And The Arts Provides A Distinguished Backdrop For Its Newest Architectural Tour De Force – Lunara. Set In Sapphire Shores, One Of Sarasota’s Most Historic And Culturally R...
Pre-construction. To Be Built. Presenting 2046 Alameda Avenue, A 9,600-square-foot Architectural Masterpiece On Sarasota Bay Designed By The Internationally Renowned Firm Choeff Levy Fischman. Walls Of Glass And An Open, Light-filled Design Create...
Welcome To A Home That Lives Like A Resort, Set On Two Lots Consisting Of 1.8 Lush, Waterfront Acres In Sarasota’s Premier Neighborhood, Harbor Acres. Crafted For Laid-back Luxury And Everyday Ease, This Nearly 12,000-square-foot Estate Offers 249...
An Exquisite Jewel Of Contemporary Architecture With Almost 180ft On Sarasota Bay With Nearly Endless Water Views. This Contemporary Masterpiece Was Designed By Renowned Dsdg Architect Mark Sultana And Built By Voigt Brothers Construction, And It ...
An Architectural Masterpiece On Sarasota Bay. Commanding One Of Sarasota’s Most Spectacular Bayfront Settings, This Gated Estate Blends Cutting-edge Engineering With Timeless Coastal Living. Built On 55 Deep Concrete Piles Extending 30 Feet Underg...
One Of The Most Exceptional Bayfront Estates On Florida’s West Coast, Offering Sweeping Sarasota Bay Views And Unforgettable Sunsets Over Longboat Key. This Gated Waterfront Retreat Features A Private Beach, Lush Tropical Landscaping, And A Stunni...
Waterfront Modern Estate | Deep Water Dock | One Mile From Downtown Sarasota. Welcome To One Of Sarasota’s Most Desirable Waterfront Addresses. Built In 2017 To The Highest Structural Standards, This Modern Estate Was Engineered To Endure Florida’...
Welcome To 1808 Flower Drive, A Resort-style Masterpiece Located In The Highly Coveted Harbor Acres Neighborhood — One Of Sarasota’s Most Prestigious Addresses. This 4-bedroom, 6-bathroom Home Spans 5,450 Square Feet Of Meticulously Designed Livin...
Nestled In The Prestigious Harbor Acres, This Exceptional 4-bedroom Waterfront Estate Embodies The Pinnacle Of Luxury Living. Boasting 100 Feet Of Prime Bay Frontage With A Private Dock, This Masterpiece Offers Breathtaking, Unobstructed Views And...
Pre-construction. To Be Built. Why Choose Between Your Perfect Sanctuary And Stunning Sunsets When You Can Have Both. Every Evening, The Horizon Performs A Breathtaking Masterpiece And From Your Private Terrace At 3950 Red Rock Way, You Hold The B...
Nestled On The Prestigious Bay Point Dr, This Georgian Colonial Home Blends Timeless Architecture & Modern Luxury. With Over 6,300 Sq.ft Of High & Dry Living Space—untouched By Recent Hurricanes—every Detail Of This Four-bedroom, All-en-suite Resi...
A Sarasota Landmark For The First Time In Over 50 Years, This Extraordinary Bayfront Estate Is Available. Nestled Beneath A Canopy Of Hundred-year-old Oaks, This 2.1-acre Property Has Remained In The Same Family Since The 1970s—making It A True ...
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 Ex...
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, Fo...
Discover One Of Sarasota’s Best Bayfront Values With Sweeping 270° Views Of Sarasota Bay, Ca’d’zan (john Ringling's Estate) , Longboat Key, And Spectacular Sunsets. Located On A Private Cul-de-sac In Ringling Point, This 7,000 Sq. Ft. Estate Offer...
Being In The Same Family For 75 Years, This Is A Rare Opportunity To Own A Stunning, Nearly Half-acre Waterfront Lot In The Highly Desirable Bay Point Park Neighborhood Of Sarasota. Situated On Protected Sailboat Water With No Bridges To The Gulf ...
Stunning Bayfront Estate At An Incredible Price. Located In The Indian Beach–sapphire Shores Neighborhood, This 1925 Mediterranean Estate Sits On Nearly Three-quarters Of An Acre With Sweeping Views Of Sarasota Bay—from The Downtown Skyline And R...
Seller Financing Is Available At Bank Rates. Waterfront Opportunity. Nestled In The Heart Of The Exclusive Cherokee Park, This Charming Old Florida Traditional Home Offers A Rare Opportunity To Own A Piece Of Sarasota's History. With 100 Feet Of ...
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, ...
One Or More Photo(s) Has Been Virtually Staged. One Or More Photo(s) Has Been Virtually Staged. Nestled Just South Of The Ringling Museum, This Prestigious West Of Trail Estate Is Set In Sarasota’s Historic Indian Beach Sapphire Shores Neighborhoo...
All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.
Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.
Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on November 6th, 2025 at 10:39pm EST.
Sarasota's "West of the Trail" neighborhoods are all established communities west of US 41. Many of the homes in these highly desirable areas have been completely remodeled or torn down and rebuilt. This area offers an ideal location for jogging and biking. Many of Sarasota's best amenities are within walking distance including restaurants, shopping, Southside Elementary School and the Sarasota Memorial Hospital.
There are a wide range of architectural styles including Spanish Mediterranean, contemporary, and old-Florida. West of the Trail real estate prices range from the $400,000 to the millions.
Popular Neighborhoods West of US 41
Established neighborhood with homes from the $500,000s to over $5,000,000.
Located south of Stickney Point, Coral Cove is a favorite among many avid boaters.
This prestigious west of the trail waterfront neighborhood is a favorite of many physicians and downtown Sarasota professionals.
Gated community located just south of proctor and west of 41.
This Mature neighborhood features tropical vegetation and homes into the millions.
This south Sarasota boating community features 112 homes with about half directly on the water.
Do you have any questions or need more information on West of the Trail real estate in Sarasota? Contact me today so we can talk about your real estate needs.
