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West of the Trail Homes for Sale

West of the Trail Homes for Sale in Sarasota, FL

West of the Trail Real Estate

Located in Sarasota, this area is known as “West of the Trail”.   We call this area West of the Trail  to simply refer to any properties that are west of route 41 which is also called Tamiami Trail.
READ MORE about West of the Trail Homes for Sale .... View the West of the Trail Neighborhoods

"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
Harbor Acres Sec 2
O5446820
  • 5 Beds
  • 6 Baths
  • 5,738 SQFT
  • 581 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...

1337 Vista Dr

Sarasota, FL - $6,200,000

Residential, Single Family Home
Harbor Acres Sec 2
A4203772
  • 5 Beds
  • 6 Baths
  • 6,425 SQFT
  • 45 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...

1540 Hillview Dr

Sarasota, FL - $5,250,000

Residential, Single Family Home
Harbor Acres Sec 2
A4197272
  • 5 Beds
  • 7 Baths
  • 7,074 SQFT
  • 109 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...

1407 Tangier Way

Sarasota, FL - $4,950,000

Residential, Single Family Home
San Remo Estates
A4205960
  • 4 Beds
  • 6 Baths
  • 5,228 SQFT
  • 12 DOM
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A Remarkable Achievement In Concept And Design, This Residence Offers Exquisite Architectural Details Both Inside & Out. Located In San Remo Estates, This Sleek & Ultra-stylish California Contemporary Home Is Perfectly Poised On One Of The Deepest...

6420 Hollywood Blvd

Sarasota, FL - $4,595,000

Residential, Single Family Home
Pine Shores Estates
A4205092
  • 4 Beds
  • 6 Baths
  • 6,878 SQFT
  • 22 DOM
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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...

1352 Harbor Dr

Sarasota, FL - $3,895,000

Residential, Single Family Home
Harbor Acres
A4174153
  • 4 Beds
  • 4 Baths
  • 4,373 SQFT
  • 375 DOM
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With Its Resplendent Homes, Prime Mainland Bayfront Position, Air Of Discreet Luxury And An Enviable 5 Minutes To Downtown, Harbor Acres Has Long Been Regarded As The Best Neighborhood In Sarasota. Meander Along Distinguished Harbor Drive And You’...

1329 Vista Dr

Sarasota, FL - $3,795,000

Residential, Single Family Home
Harbor Acres Sec 2
A4193735
  • 4 Beds
  • 4 Baths
  • 3,762 SQFT
  • 164 DOM
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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...

1344 Harbor Dr

Sarasota, FL - $3,793,000

Residential, Single Family Home
Harbor Acres
A4187925
  • 5 Beds
  • 6 Baths
  • 6,101 SQFT
  • 234 DOM
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A Gorgeous Waterfront Estate Located In The Desirable Bayfront Community Of Harbor Acres—sarasota’s Most Coveted Location.originally Constructed In 1949, This Captivating Residence Underwent A Meticulous And Expansive Renovation In 2004. Its Class...

7697 Cove Ter

Sarasota, FL - $3,399,000

Residential, Single Family Home
Southpointe Shores Unit 2
A4185483
  • 4 Beds
  • 5 Baths
  • 4,797 SQFT
  • 250 DOM
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Possibly One Of The Finest Views Of Sarasota Bay, This Spectacular Gated Boating Estate Offers Stunning Views Of The Intracoastal Waterway From Nearly All Rooms. Located On A Quiet Cul-de-sac In A Convenient Mainland Community; Rear Southern Expos...

1449 Hillview Dr

Sarasota, FL - $3,350,000

Residential, Single Family Home
Harbor Acres Sec 2
A4189312
  • 5 Beds
  • 5 Baths
  • 4,982 SQFT
  • 212 DOM
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Exceptional And Incomparable Harbor Acres One Level Residence Was Completely Updated In 2015 For Unsurpassed Luxury. Privately Situated Back From The Street On This Estate Sized Lot, This Four-bedroom, Three-and-a-half-bath Main Residence Is In T...

1346 Harbor Dr

Sarasota, FL - $3,290,000

Residential, Single Family Home
Harbor Acres
A4203707
  • 4 Beds
  • 4 Baths
  • 3,975 SQFT
  • 45 DOM
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Deep Sailboat Water And The Location In The Prestigious Harbor Acres Neighborhood Highlight Two Of The Many Desirable Attributes Of This Four Bedroom, Three-and-one-half Bath Residence Set On More Than A Quarter Acre Near Southside Village And C...

1145 N Lake Shore Dr

Sarasota, FL - $2,995,000

Residential, Single Family Home
Oyster Bay Estates
A4205150
  • 5 Beds
  • 7 Baths
  • 6,963 SQFT
  • 28 DOM
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Huge Waterfront Estate In One Of Sarasota’s Most Exclusive Neighborhoods. This Is Your Chance To Own The Least Expensive Home On The Most Expensive Street. An Investor's Dream; Ideal For Full-time Or Seasonal Residents. Nearly 7,000 Sq Ft Of Luxur...

1412 Peregrine Point Dr

Sarasota, FL - $2,995,000

Residential, Single Family Home
The Landings
A4201855
  • 5 Beds
  • 5 Baths
  • 6,685 SQFT
  • 23 DOM
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Experience A Rare Combination Of Superlatives: An Open Bay Front Property With Good Boating Water And A Large, Elevated Modern Home In The Highly Desirable And Gated Landings Community. This Extraordinary Custom Home Embraces A Cinematic Panorama ...

1710 Vamo Dr

Sarasota, FL - $2,995,000

Residential, Single Family Home
Vamo Amd Of
A4193717
  • 6 Beds
  • 4 Baths
  • 4,121 SQFT
  • 341 DOM
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Experience A Life Of Sheer Waterfront Serenity On 3 Pristine Acres In Sarasota. This Park-like Setting On The Intracoastal Is Straight From The Pages Of A Fairytale, And Could Provide The Location For The Home Of Your Dreams. Two Existing Properti...

1581 Hillview Dr

Sarasota, FL - $2,895,000

Residential, Single Family Home
Harbor Acres
A4183577
  • 4 Beds
  • 4 Baths
  • 4,331 SQFT
  • 282 DOM
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Pre-construction. To Be Built. New Construction In Harbor Acres, One Of The Most Sought After And Desirable Areas In Sarasota. A Warm Contemporary Built By Greenlife Luxury Homes, Offering An Exceptional Level Of Finishes And Attention To Detail....

1500 Cunliff Ln

Sarasota, FL - $2,750,000

Residential, Single Family Home
Acreage & Unrec
A4195876
  • 4 Beds
  • 3 Baths
  • 2,803 SQFT
  • 128 DOM
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Rarely Available Property On Almost Half Acre Lot With Panoramic Bay Views, To The South Siesta Key And Siesta Key Bridge, To The North John Ringling Bridge And Lido Key. Certain Features Of Downtown Can Also Be Captured From This Property. Owne...

1732 North Dr

Sarasota, FL - $2,700,000

Residential, Single Family Home
Cherokee Park 2
A4191053
  • 5 Beds
  • 5 Baths
  • 4,468 SQFT
  • 197 DOM
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This Under Construction Home Is The Ultimate Illustration Of British West Indies, Nestled On A Mainland Tree-lined Street In What Is Considered Sarasota’s Best Neighborhood, Cherokee Park. Between Downtown Sarasota And Siesta Key This Home Is A Ha...

1508 Flower Dr

Sarasota, FL - $2,299,000

Residential, Single Family Home
Harbor Acres
A4198894
  • 4 Beds
  • 4 Baths
  • 4,750 SQFT
  • 89 DOM
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A $200,000 Price Reduction Makes This A Compelling Price For A Home In Harbor Acres, Probably The Most Enviable Location In Sarasota. It’s Mainland Living, Close To Downtown & The Hospital, A True Neighborhood, Short Walk To Southside Village Wit...

5816 Tidewood Ave

Sarasota, FL - $2,295,000

Residential, Single Family Home
Baywood Colony Westport Sec 2
A4180808
  • 4 Beds
  • 4 Baths
  • 4,195 SQFT
  • 312 DOM
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Located On Little Sarasota Bay, The View From This West Facing Home Provides Magnificent Sunsets And Tranquil Wildlife Activity. Enter Through Exquisite Pecky Cypress Doors With Expansive West Facing Views Of The Bay From Most Rooms. Superior Craf...

5824 Tidewood Ave

Sarasota, FL - $2,250,000

Residential, Single Family Home
Baywood Colony Westport Sec 1
A4205461
  • 4 Beds
  • 5 Baths
  • 4,619 SQFT
  • 18 DOM
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Spectacular Sunsets From This Stunning Home With Full Views Of Little Sarasota Bay, Directly Across From Siesta Key! Travertine Walkway Welcomes You To A Grand Front Entry, As You Enter, Enjoy A Cascade Of Upscale Finishes In This Well-appointed ...

1615 S Lake Shore Dr

Sarasota, FL - $2,250,000

Residential, Single Family Home
Oyster Bay Estates
A4198495
  • 3 Beds
  • 4 Baths
  • 4,642 SQFT
  • 226 DOM
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Beautiful Lake Front Address In Oyster Bay! Wooded Setting With Tall Pines And Old Oaks On Over ½ An Acre Sets The Scene For This Custom-built Home Fronting Onto A Peaceful Spring-fed Lake Where You Are Transported To The Carolinas. Contemporary S...





West of the Trail Neighborhood List


More About West of the Trail

West of the Trail real estate that is for sale is sometimes referred to as luxury homes, because a home in this area can range from $400,000 to well into the millions with many homes situated on the water with views of Sarasota Bay and the Intracoastal Waterway.
West of the Trail Homes for Sale

This is one of the most prestigious and oldest areas of Sarasota.  Classical Florida charm, large  luxury homes with distinct character.  This area includes the historical neighborhoods of Cherokee ParkHarbor AcresMcClellan ParkDesota Park  and  The Landings among others. 

These areas are typically enjoyed by professionals and families who enjoy the ease and access to downtown living with the old Florida neighborhood flavor.

This tranquil area offers narrow winding streets of older Florida homes with a historical look and feel.  Typically when visitors from the north see the homes that are West of the Trail their first comment is how much it reminds them of homes from the north or New England. 

With its close proximity to Sarasota Memorial Hospital it has made this area a favorite among medical professionals.  Please find above a list of all the current real estate for sale that is West of the Trail in Sarasota.  If you would prefer to view properties by community that is West of the Trail simply click onto a community of your choice.

If you are looking for something specific or have any questions about a home that is West of the Trail please call Sara at (941) 586-4790 or email her directly at Sara@SaraSellsSarasota.com




                                                                                                           
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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 January 20th, 2018 at 7:33pm EST.