Below are the current West of the Trail Sarasota real estate listings. Our website allows you to easily search through the 118 single-family homes for sale priced from $260,000 to $22,000,000. 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: | 118 |
| Average Price: | $3,235,072 |
| Highest Price: | $22,000,000 |
| Lowest Price: | $260,000 |
| Average Size: | 3,274 ft² |
| Average Price Per Square Foot: | $846 per ft² |
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Three Dwellings Set On 2.4 Gated Acres With An Impressive 240 Feet Of Pristine Waterfront, This Rare Sarasota Compound Offers Over 10,000 Square Feet Of Pure Privacy, Serenity, And Elevated Coastal Living. Perfectly Positioned In The Heart Of The ...
2026 National Gold Nugget Award Of Merit Winner. Srq Magazine 2026 Home Of The Year. 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 For...
Pre-construction. To Be Built. Soon To Be Under Construction. Located On The Coveted Waterfront Of Bay Point Drive, This Extraordinary Custom Residence Represents A Rare Opportunity To Own A Truly Bespoke New-build In One Of Sarasota’s Most Desira...
One Of Sarasota’s Greatest Bayfront Estates, This Stunning 1.38 Acre Waterfront Home Has Recently Undergone A Comprehensive Renovation Throughout, Enhancing Every Room With Refined Finishes And Modern Systems While Preserving Its Timeless Architec...
Under Construction. Superb New Construction Opportunity In Harbor Acres, A One-third-acre Waterfront Property On The Widest Part Of The Neighborhood's Deep-water Harbor On Sarasota Bay. The Views Are Great And The Home Is Located On A Protected, S...
An Architectural Landmark Of Contemporary Design And Sustainable Luxury, This Award-winning Estate Redefines Coastal Living In Sarasota’s Coveted Museum Area. Honored As Srq Magazine’s Home Of The Year Across Multiple Categories In 2023, The Gated...
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...
Nestled In The Heart Of Sarasota, Florida, "the Seathrough House" Stands As A Testament To Timeless Elegance And Modern Sophistication. Designed By The Acclaimed Architectural Firm Sweet Sparkman And Meticulously Crafted By Builder Josh Wynne, Thi...
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 1.1 Acres Of Pristine Bayfront Along Sarasota Bay, Etowah Stands As A Timeless Icon Of Sarasota’s Rich Architectural Heritage, Offering Sweeping, Wide-open Bay Views To The North And South, From The Manicured Lawn At The Water’s Edge Al...
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 People Dream About But Rarely Find. Set On An Oversized 2/3-acre Lot With 172 ...
Dreaming Of Breathtaking Sunsets? This Property Is For You! A One Of A Kind Bayfront Lot Located In Highly Sought-after Cherokee Park, West Of Trail. Located In "x" Flood Zone This Property Offers Unobstructed Panoramic Views Of Sarasota Bay. The...
Where The World's Most Exclusive Resorts Inspire Everyday Living. Imagine Waking Each Morning In A Residence That Rivals The Refined Elegance Of An Aman Private Estate, The Clean Architectural Sophistication Of A Bulgari Resort, And The Effortl...
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 Re...
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 Allegra Homes Masterfully Blends Timeless Coastal Elegance With Modern Luxury. T...
Virtually Staged. Experience Luxury West-of-trail Living In Sarasota’s Coveted Oyster Bay Neighborhood. This Newly Built 2026 Custom Residence Offers 5 Bedrooms, 5 Full And 2 Half Baths—all On One Thoughtfully Designed Living Level—featuring 4,545...
Pre-construction. To Be Built. Welcome To Effortless Coastal Luxury In The Coveted Harbor Acres Neighborhood, Where Timeless Glamour Meets Breezy, Tropical Elegance. The Royal Palm Is Heritage Builder’s Latest Creation. The Palm Beach–style Reside...
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 ...
Under Construction. This Exceptional, Boater’s Residence Is Ideally Positioned On Hudson Bayou, Designed To Impress At Every Turn. Showcasing The Very Best Of Sarasota’s Waterfront Lifestyle, The Property Features Outstanding Boating Amenities, In...
Under Construction. Allegra Homes Presents The Custom-built Southside Iv In Harbor Acres—one Of Sarasota’s Signature Bayfront Enclaves. Designed For Elevated Everyday Living, This 5br/4.5ba Residence Balances Drama And Comfort With A Soaring Great...
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 August 11th, 2026 at 7:52am EDT.
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.
