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West of the Trail Sarasota

West of the Trail homes

Ask any local Sarasota resident to identify the most desirable properties in town and you'll hear them say, “anything West of the Trail.” The premium features that define West of Trail neighborhoods are waterfront property, charming neighborhood character, low commute times and pedestrian traffic.  Learn more about West of the Trail Homes.

West of the Trail Homes for Sale

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
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1333 Vista Dr, Sarasota, FL - $6,249,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,738 SQFT
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Under Construction. Inspired By The Understated Luxury Of A Caribbean Villa, This Brand New, Two-story Home This Custom Residence Offers Serene Water Views From Its Prime Location On 100 Ft Of Sarasota Bay. The Approximately 5,800 Sq. Ft. Of Inter...

Photo of Listing #A4203772

1337 Vista Dr, Sarasota, FL - $6,100,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 6,425 SQFT
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Pre Construction. To Be Built A Collaboration Of Sarasota's Finest Clifford M Scholtz, Architects, Murray Homes, Builder And Michael A. Gilkey, Landscape Architect Have Combined Their Talents To Create A M...

1717 Southpointe Dr, Sarasota, FL - $5,050,000

Residential, Single Family Home
  • 4 Beds
  • 9 Baths
  • 6,883 SQFT
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Full Bay Views & 10+ Car Garage. This House Is Different & Cool. The Owners Originally From La Jolla Wanted To Bring A Touch Of Southern California To South West Florida. The Classic Timeless Exterior Is Paired With A Soft Contemporary Interior. O...

3544 San Remo Ter, Sarasota, FL - $4,990,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 6,710 SQFT
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Lake Tahoe Came To Sarasota Bay In 2009…and They Built A House Together. This Spectacular, Custom-designed Home Offers 2 Full Master Suites, Each With Their Own Private Terrace, And 3 Guest Suites For Visiting Family Or Friends. Pulling In To Your...

Photo of Listing #A4197272

1540 Hillview Dr, Sarasota, FL - $4,950,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 7,074 SQFT
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Set In A Commanding Waterfront Location On Hillview Drive, One Of The Most Prized Addresses In Sarasota, This Simply Sublime Home Is Bestowed With Scenic Southern Exposure, Vast Yet Comfortable Living Spaces And Exceptional Quality. Panoramic Pers...

Photo of Listing #A4194135

1479 Bay Point Dr, Sarasota, FL - $4,295,000

Residential, Single Family Home
  • 4 Beds
  • 3 Baths
  • 3,783 SQFT
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Rare Opportunity To Purchase Land In One Of The Most Exclusive, Waterfront, West Of Trail, Neighborhoods. This Bay Point Gem Is On The Market For The First Time Since Built In 1947. Breathtaking Views Of Sarasota Bay, Ringling Bridge And Golden Ga...

Photo of Listing #A4205092

6420 Hollywood Blvd, Sarasota, FL - $4,295,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 6,878 SQFT
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Gorgeous Waterfront Gated Estate! This 6800 Sq Ft Home Is Situated On A Double Lot With Over 300 Ft Of Water Frontage & Highlights 4 Bdrms & 5 1/2 Baths. Tranquil Bay Views From Your Master Suite & Beautifully Remodeled Master Bath. Relax & Gaze A...

1541 Bay Point Dr, Sarasota, FL - $4,199,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 6,374 SQFT
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Refined Elegance Meets Luxurious Quality In This One Of A Kind Home Located In The Heart Of Sarasota’s Most Prestigious Street. Inspiring Timeless Architecture And Thoughtful Design Exude The Epitome Of Class And Comfort. The Dramatic Two-story F...

1230 N Lake Shore Dr, Sarasota, FL - $3,890,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 4,111 SQFT
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Public May Remark

1329 Vista Dr, Sarasota, FL - $3,795,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,762 SQFT
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Looking For A Peaceful Home On A Large Lot, Overlooking The Boat Basin In Harbor Acres? One That Is Perfect For Entertaining With A Large Refreshing Pool, Abundant Windows For Viewing The Beauty Of The Bay, Four Comfortable And Private Bedroom Sui...

1352 Harbor Dr, Sarasota, FL - $3,795,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 4,373 SQFT
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This Is Exclusive Waterfront Living At Its Best In Harbor Acres. Perfectly Positioned Just A Few Homes In From The Open Bayfront, With Stunning Views Of Sarasota Bay And John Ringling Bridge, This Newer Four-bedroom Waterside Home Is Ready For You...

1640 Bay Harbor Ln, Sarasota, FL - $3,499,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,093 SQFT
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A Builders Expose’ You Can Now Call Home Sweet Home. Hidden Behind Iron Gates, At The End Of A Private Street, Littered With Extravagant Details Throughout, Brings This Almost Castle Like Mediterranean Style Home To A New Level. Boasting Over 7,00...

West of the Trail Homes

West of the Trail Sarasota real estateWest of the Trail homes offer special things for the homebuyer. A West of the Trail address means in-town living mingled with some of Sarasota's best shops and boutiques, markets, cafes, restaurants, schools and exceptional health care. 

This area is comprised of diverse and distinctive residences that may include small cottages and villas, Sarasota School of Architecture homes and condominiums, luxury estates, historic buildings and waterfront properties. If you are looking for a neighborhood with personality, taste, and sure-fire staying power on the market, you will find all of this and more in a West of the Trail home.

 Map of West of the Trail in Sarasota, FL

West of the Trail Real Estate News

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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.

Listing information last updated on May 23rd, 2018 at 7:00am EDT.