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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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1717 Southpointe Dr

Sarasota, FL - $4,995,000

Residential, Single Family Home
Southpointe Shores
O5569288
  • 4 Beds
  • 9 Baths
  • 6,883 SQFT
  • 175 DOM
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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
San Remo Estates
A4403580
  • 5 Beds
  • 7 Baths
  • 6,710 SQFT
  • 574 DOM
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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...

1409 S Lake Shore Dr

Sarasota, FL - $4,950,000

Residential, Single Family Home
Oyster Bay Estates
A4405978
  • 4 Beds
  • 4 Baths
  • 5,193 SQFT
  • 67 DOM
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Pre-construction: To Be Built. This Incredibly Beautiful Home Will Be Built On Prestigious South Lake Shore Drive– A Long-established, Highly-regarded Oyster Bay Estates Neighborhood. Tucked Away On Sarasota’s Mainland, This Private Waterside Oas...

1540 Hillview Dr

Sarasota, FL - $4,500,000

Residential, Single Family Home
Harbor Acres Sec 2
A4197272
  • 5 Beds
  • 7 Baths
  • 7,074 SQFT
  • 321 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...

2231 Oriole Dr

Sarasota, FL - $3,495,000

Residential, Single Family Home
Mcclellan Park
A4405569
  • 5 Beds
  • 8 Baths
  • 8,162 SQFT
  • 66 DOM
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This Magnificent Estate Sits Gracefully On An Oversized Lot In One Of Sarasota’s Most Sought-after “west Of Trail” Neighborhoods, Mcclellan Park. Impressive From The Moment One Ascends The Limestone Walkway And Staircase To The Front Porch, This R...

1329 Vista Dr

Sarasota, FL - $3,400,000

Residential, Single Family Home
Harbor Acres Sec 2
A4193735
  • 4 Beds
  • 4 Baths
  • 3,762 SQFT
  • 376 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...

1503 Blue Heron Dr

Sarasota, FL - $3,200,000

Residential, Single Family Home
Paradise Shores
A4212851
  • 4 Beds
  • 4 Baths
  • 4,518 SQFT
  • 154 DOM
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Prime Location On Sailboat Water. Custom Built By Todd Johnston In 2015 In The British West Indies Style. Expansive Bay Views From The Infinity Pool, Spa And Open Patio. Enjoy Al Fresco Dining With Over-sized Gas Grill, Refrigerator, Sink And Ice ...

6438 Hollywood Blvd

Sarasota, FL - $3,199,900

Residential, Single Family Home
Pine Shores Est 7th Add
A4209878
  • 3 Beds
  • 3 Baths
  • 4,738 SQFT
  • 193 DOM
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Coucher Du Soleil (french For “sunset”): This Elegant Waterfront Home Is Reminiscent Of The 1920’s “gilded Age” In The French Style Of New Orleans Mansions. This Home Is A Craftsman’s Work Of Art, From The Skillfully Crafted Crown Moldings, Baseb...

1655 Bay Harbor Ln

Sarasota, FL - $3,099,000

Residential, Single Family Home
Stillwater On The Bay
A4404746
  • 5 Beds
  • 6 Baths
  • 6,402 SQFT
  • 77 DOM
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This Private Gated Enclave Of Six Homes Is Quiet And Relaxing. Close To Siesta Beaches And All Sarasota Has To Offer. This 6430 Square Foot Residence Has All The Upgrades Expected In A Bay Front Mansion. Five Bedrooms And Six And A Half Bathrooms ...

6322 Hollywood Blvd

Sarasota, FL - $3,000,000

Residential, Single Family Home
Emerald Harbor
A4401823
  • 6 Beds
  • 7 Baths
  • 6,051 SQFT
  • 111 DOM
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This Is The One! *built In 2014 This Ultimate Waterfront Estate Is Nearly Half An Acre With 105'of Bay Frontage Directly On Emerald Harbor & Boasts 6bed,3baths, & 2 1/2 Baths* Spectacular Hardwood Flooring Throughout Gives You A Feeling Of Grandeu...

1449 Hillview Dr

Sarasota, FL - $2,995,000

Residential, Single Family Home
Harbor Acres Sec 2
A4407215
  • 4 Beds
  • 5 Baths
  • 4,982 SQFT
  • 417 DOM
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You Will Love The Stunning Coastal Contemporary Updates (completed In 2015) Offered From Every Room Of This Harbor Acres Waterfront Home. Set Back Far From The Road And Surrounded By Privacy Walls Of Lush Manicured Vegetation. The Sprawling Interi...

4805 Riverwood Ave

Sarasota, FL - $2,995,000

Residential, Single Family Home
Riverwood Park
A4406276
  • 7 Beds
  • 8 Baths
  • 7,900 SQFT
  • 49 DOM
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Lushness Surrounds You As Old Florida Welcomes You Along Your Private Gated Drive Leading To A Greek Revival Estate That Has Been Lovingly And Intelligently Expanded And Updated To The 21st Century. While You Have The Old Charm Of A Formal Dining ...

1581 Hillview Dr

Sarasota, FL - $2,895,000

Residential, Single Family Home
Harbor Acres
A4183577
  • 4 Beds
  • 5 Baths
  • 4,508 SQFT
  • 494 DOM
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Under Construction. To Be Built. Under Construction In Harbor Acres, One Of The Most Desirable Areas In Sarasota. A Warm Contemporary, Built By Greenlife Luxury Homes, Offering An Exceptional Level Of Finishes And Attention To Detail. The Dramat...

7692 Cove Ter

Sarasota, FL - $2,795,000

Residential, Single Family Home
Southpointe Shores
A4401935
  • 3 Beds
  • 3 Baths
  • 2,640 SQFT
  • 112 DOM
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A Rarely Available Point Property With An Astounding 210 Feet Of Mainland Bayfront Located On A Cul-de-sac In Coveted Southpointe Shores. This Is An Opportunity To Moor A 50 ‘ Yacht, In Protected Deep Water Without Disturbing The Remarkable View! ...

1500 Cunliff Ln

Sarasota, FL - $2,750,000

Residential, Single Family Home
Acreage & Unrec
A4195876
  • 4 Beds
  • 3 Baths
  • 2,803 SQFT
  • 340 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...

1710 Vamo Dr

Sarasota, FL - $2,695,000

Residential, Single Family Home
Vamo Amd Of
A4193717
  • 6 Beds
  • 4 Baths
  • 4,121 SQFT
  • 553 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...

1606 North Dr

Sarasota, FL - $2,599,000

Residential, Single Family Home
Cherokee Park 2
U8009366
  • 6 Beds
  • 6 Baths
  • 5,538 SQFT
  • 52 DOM
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Elegant And Refined In Every Aspect, This Sarasota West Of Trail Home In Cherokee Park, Comprises Only The Highest End Custom Craftsmanship. This Home Was Built By The Award-winning Tony Ngai. Located In One Of Sarasota's Most Iconic Neighborhoods...

1427 Cedar Bay Ln

Sarasota, FL - $2,495,000

Residential, Single Family Home
The Landings
A4408881
  • 5 Beds
  • 6 Baths
  • 6,083 SQFT
  • 27 DOM
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Set In The Private, Gated Community Of The Landings With Views Over The Bay, This 5-bedroom Plus Den, 5.5-bath Family Home Is Offered To The Market For The First Time. From The Vaulted Entrance Hall, With Wooden Floors Inlaid With Marble, Opening ...

1235 N Lake Shore Dr

Sarasota, FL - $2,495,000

Residential, Single Family Home
Oyster Bay Estates
A4213972
  • 4 Beds
  • 3 Baths
  • 3,535 SQFT
  • 153 DOM
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Water Views In The Front And Back Of This 4br Plus Family And Bonus Rooms Oyster Bay Home Create An Idyllic Backdrop For An Easygoing Family Lifestyle. This Private Residence Is Surrounded By Lush Manicured Foliage, With A Charming Courtyard Entry...

7643 Cove Ter

Sarasota, FL - $2,399,900

Residential, Single Family Home
Southpointe Shores
A4403215
  • 4 Beds
  • 4 Baths
  • 4,320 SQFT
  • 95 DOM
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Experience The Allure Of Coasting Living At Casa Azul. Located West Of Trail, This Four-bedroom Residence Is Nestled In Southpointe Shores, A Waterfront Community With Some Of The Best Deep Boating Water In South Sarasota. Poised On 100’ Of Deep S...

3921 Red Rock Way

Sarasota, FL - $2,390,000

Residential, Single Family Home
Hansen
A4212223
  • 4 Beds
  • 5 Baths
  • 3,801 SQFT
  • 171 DOM
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Pre-construction - To Be Built - This Expansive Custom Home Is Situated On An Estate Sized Home Site In Sarasota's Coveted West Of Trail Area. Through A Striking Motor Court, Owners Are Greeted By A Wide Great Room With Expansive Views Of Stunning...





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 August 20th, 2018 at 2:46pm EDT.