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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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1435 Hillview Dr

Sarasota, FL - $4,995,000

Residential, Single Family Home
Harbor Acres
A4423245
  • 3 Beds
  • 5 Baths
  • 4,876 SQFT
  • 6 DOM
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Enter This Grand Harbor Acres Estate Through Antique Wrought Iron Gates And Proceed Down The Long Winding Paver Driveway To This Very Private Setting On 115 Ft Of Protected Yacht Basin. The Lushly Landscaped And Manicured Grounds Comprise Over Thr...

1509 S Lodge Dr

Sarasota, FL - $4,995,000

Residential, Single Family Home
Cherokee Park
A4416416
  • 5 Beds
  • 6 Baths
  • 5,800 SQFT
  • 70 DOM
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The Spectacular Location Of This Waterfront Home Is Quite Unique. Resting On Nearly 2/3-acre Of Property At The End Of A Quiet Cul-de-sac, Just One Parcel In From The Point-lot Location That Overlooks Sarasota Bay. There Are Aspects At This Custom...

3544 San Remo Ter

Sarasota, FL - $4,990,000

Residential, Single Family Home
San Remo Estates
A4403580
  • 5 Beds
  • 7 Baths
  • 6,710 SQFT
  • 721 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
  • 214 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...

1430 Harbor Dr

Sarasota, FL - $4,700,000

Residential, Single Family Home
Harbor Acres Sec 2
A4423407
  • 4 Beds
  • 6 Baths
  • 6,631 SQFT
  • 5 DOM
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Ideally Situated On Deep Boating Water In One Of Sarasota’s Most Desirable Neighborhoods, Harbor Acres, This Stunning 4 Bedroom, 4 Bathroom Residence Is One To Be Desired. Positioned For Awe-inspiring Views Of Sailboats And Sunsets, This Home Span...

3246 Old Oak Dr

Sarasota, FL - $4,600,000

Residential, Single Family Home
Shoreland Woods Sub
A4412754
  • 3 Beds
  • 4 Baths
  • 4,037 SQFT
  • 109 DOM
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Pre Construction. To Be Built. Are You Ready To Build Your Dream? Welcome To Le Rêve, A Tropical Bayfront Paradise In Sarasota, Florida. With Nearly 200’ Of Frontage On Sarasota Bay, This Beautiful Home Offers You A Look Into The Best Of Florida… ...

3850 Tangier Ter

Sarasota, FL - $4,500,000

Residential, Single Family Home
San Remo Estates
A4412183
  • 4 Beds
  • 5 Baths
  • 3,984 SQFT
  • 137 DOM
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Pre-construction. To Be Built. Imagine. Yes, Close Yourself From Distractions And Imagine The Next Great Waterfront Estate Proposed To Be Built On The Deepest Protected Yacht Basin In Sarasota. Visualize An Ultra-premium Custom Home With Lots Of S...

1807 Oleander St

Sarasota, FL - $4,499,000

Residential, Single Family Home
0364 Poinsettia Park 2
A4414354
  • 7 Beds
  • 9 Baths
  • 9,492 SQFT
  • 91 DOM
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Prepare To Be Enchanted. Imagine Being Swept Away To A Vine-covered French Chateau Nestled On A Hillside In The Wine Country Of France. Open Your Eyes And Realize You Are In This Walled, Gated Estate In The Coveted West Of Trail Neighborhood Just ...

1726 Questar Ln

Sarasota, FL - $4,000,000

Residential, Single Family Home
None
A4401320
  • 4 Beds
  • 7 Baths
  • 6,719 SQFT
  • 5 DOM
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Short Sale. Short Sale. Built In 2004, Home Has Been Pre-inspected To Confirm Its Top Condition. This Private, Gated, Resort Like Bayfront Property, Close To The City And Very Close To Area’s Most Beautiful Beach On Siesta Key, Offers Everything F...

6420 Hollywood Blvd

Sarasota, FL - $3,995,000

Residential, Single Family Home
Pine Shores Estates
A4422271
  • 5 Beds
  • 6 Baths
  • 6,878 SQFT
  • 7 DOM
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Experience The Best Of Waterfront Living In The Heart Of Sarasota Just West Of Trail In Pine Shores Estates. This Walled And Gated Bayfront Home Is Sited At The End Of A Quiet Tree-lined Street And Is In A Near Perfect Location Allowing For Easy A...

1545 Mallard Ln

Sarasota, FL - $3,995,000

Residential, Single Family Home
Paradise Shores
A4415376
  • 4 Beds
  • 6 Baths
  • 5,279 SQFT
  • 101 DOM
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Perfectly Situated On A Corner Waterfront Lot In This Prime West Of Trail Location Sits This 3 Year New "voigt Brothers" Custom Built Home. Entering The Stunning Double Wood & Glass Doors, The Expansive Great Room With Water Views Sets The Tone Fo...

7350 Captain Kidd Ave

Sarasota, FL - $3,895,000

Residential, Single Family Home
Buccaneer Bay
A4415503
  • 3 Beds
  • 4 Baths
  • 4,608 SQFT
  • 84 DOM
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Why Wait For New Construction When You Can Have It All Right Now! Built In 2016, This Magnificent Gated Bayfront Estate With Over 160 Feet Of Frontage Is Idyllically Set At The End Of A Cul-de-sac To Deliver Panoramic Bay Views And Stunning Sunset...

1352 Harbor Dr

Sarasota, FL - $3,695,000

Residential, Single Family Home
Harbor Acres
A4412879
  • 4 Beds
  • 4 Baths
  • 4,373 SQFT
  • 105 DOM
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Exclusive Waterfront Living At Its Best From This Stunning, Newer Harbor Acres Home! Perfectly Positioned Just A Few Lots In From The Open Bayfront, Fall In Love With Impeccable Views Of Sarasota Bay And John Ringling Bridge From Nearly Every Room...

7799 Holiday Dr N

Sarasota, FL - $3,695,000

Residential, Single Family Home
Holiday Harbor
A4413641
  • 4 Beds
  • 5 Baths
  • 3,751 SQFT
  • 108 DOM
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Enjoy Unobstructed Bay Views And Endless Sunsets From This One-of-a-kind Bay Front Home Custom Built By Jonas Yoder Custom Homes In 2016. Perfectly Positioned To Take Advantage Of Its 273 Waterfront Feet And To Maximize The Water Views From Almost...

1640 Bay Harbor Ln

Sarasota, FL - $3,499,900

Residential, Single Family Home
Stillwater On The Bay
C7410015
  • 4 Beds
  • 6 Baths
  • 5,093 SQFT
  • 7 DOM
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Refined Elegance Meets Luxurious Quality In This One Of A Kind Mediterranean Home, Located In The Heart Of Sarasota’s Prestigious Intracoastal Waterway. Approaching Through The Iron Gates Towards The Private Culdesac, The Prodigious 25’ Entrance G...

2231 Oriole Dr

Sarasota, FL - $3,495,000

Residential, Single Family Home
Mcclellan Park
A4405569
  • 5 Beds
  • 8 Baths
  • 8,162 SQFT
  • 213 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
  • 521 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...

6438 Hollywood Blvd

Sarasota, FL - $3,199,900

Residential, Single Family Home
Pine Shores Est 7th Add
A4209878
  • 3 Beds
  • 4 Baths
  • 4,738 SQFT
  • 340 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...

4805 Riverwood Ave

Sarasota, FL - $2,995,000

Residential, Single Family Home
Riverwood Park
A4406276
  • 7 Beds
  • 8 Baths
  • 7,900 SQFT
  • 196 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 ...

1449 Hillview Dr

Sarasota, FL - $2,895,000

Residential, Single Family Home
Harbor Acres Sec 2
A4407215
  • 4 Beds
  • 5 Baths
  • 4,982 SQFT
  • 564 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...

1581 Hillview Dr

Sarasota, FL - $2,895,000

Residential, Single Family Home
Harbor Acres
A4183577
  • 4 Beds
  • 5 Baths
  • 4,508 SQFT
  • 641 DOM
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Under Construction. To Be Built. Spend Your Holiday Season In Your New Harbor Acres Home, To Be Completed Oct 2018. A Warm Contemporary, Built By Greenlife Luxury Homes, Offering An Exceptional Level Of Finishes And Attention To Detail. The Dramat...





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 16th, 2019 at 1:15am EST.