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Sarasota "West of Trail" Homes

west_of_trail_mansion_400Sarasota’s “West of Trail” neighborhoods are comprised of an eclectic mix of Bay Front mansions and older 40s and 50’s style ranches. Because it follows the bay from north to south to the west of Tamiami Trail (US 41), you'll find some of Sarasota’s oldest and most historic neighborhoods. Many of the homes in these highly desirable neighborhoods have been torn down and rebuilt, while others have been substantially remodeled. At it’s center, you’ll find the Southside Village area where homes are within walking distance of Sarasota's best amenities, including Sarasota's Bay Front Park, Downtown Sarasota and village shops. On the north end, Ringling Museum anchors the historic “museum area”. Throughout the “West of Trail” area, you’ll find walkable neighborhoods and parks meant to enhance the urban lifestyle.

If you want more detailed information about a listing, just click on the VIEW DETAILS action button. Here you will find detail information about the property, including additional photos and virtual tours, when available. If you like what you see and want to come back to it easily, just click on the BOOKMARK button to save it to your favorites.

See below to view real estate listings in Sarasota's historic "West of Trail" neighborhoods

West of 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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7922 S Holiday Dr, Sarasota, FL - $6,975,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 8,505 SQFT
  • 43 DOM
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Auction: December 13th. Selling Without Reserve. Open Daily 1–4pm By Appointment. Sunset Preview Event November 15th From 4–7pm. Enjoy Indoor/outdoor Luxury At This Five Bedroom Bayfront Estate Featuring Modern Home Technology, A Large Chef's Kitc...

1333 Vista Dr, Sarasota, FL - $6,249,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,738 SQFT
  • 534 DOM
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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 - $6,200,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 6,425 SQFT
  • 3 DOM
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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...

2050 Benjamin Franklin Dr #ph-1102, Sarasota, FL - $5,995,000

Residential, Condo
  • 4 Beds
  • 5 Baths
  • 5,987 SQFT
  • 438 DOM
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This Is The Only Residence Available At The Exclusive Orchid Beach Club On Lido Key. It Is Also One Of The Only Penthouses In All Of Sarasota To Feature Views Of The Gulf By Day And City Lights By Night. Arrive To Your Personal 4-car Garage, Pract...

1540 Hillview Dr, Sarasota, FL - $5,595,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 7,074 SQFT
  • 60 DOM
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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...

1001 Tocobaga Ln, Sarasota, FL - $5,391,001

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,926 SQFT
  • 17 DOM
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Experience A Rare Perspective Sweeping From Sarasota Bay To Downtown– All In A Nearly New Waterfront Masterpiece Completed In 2017 To The Latest Construction/hurricane Codes. Tucked Away Behind The Private Gates Of Tocobaga Bay, The 5-suite Proper...

Photo of Listing #A352305

7660 S Tamiami Trl, Sarasota, FL - $4,995,000

Commercial
  • 3,850 DOM
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Wow! Large Price Reduction. 90% Seller Financing Available. Bring Creative Offers. Rarely Available Property Type! Current Use As 23 Unit Retail Ctr & 38 Boat Marina On Us41 In Sarasota Near Siesta. Commercial Center Includes Several Bldings & I...

3544 San Remo Ter, Sarasota, FL - $4,890,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 6,710 SQFT
  • 318 DOM
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Stunning Sarasota Waterfront Property. Prime Location In Desirable West-of-trail San Remo Estates, This Custom Built 6,700 Sq. Ft. Home Offers 2 Master Suites With Private Terraces, 3 Guest Suites, 2 Half Baths. Gourmet Kitchen Is Outfitted With V...

1479 Bay Point Dr, Sarasota, FL - $4,375,000

Land, Residential Development
  • 107 DOM
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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...

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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 December 16th, 2017 at 2:03am EST.