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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 Drive

SARASOTA, FL - $6,249,000

Residential, Single Family Home
HARBOR ACRES SEC 2
O5446820
  • 5 Beds
  • 6 Baths
  • 5,738 SQFT
  • 673 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 Drive

SARASOTA, FL - $6,100,000

Residential, Single Family Home
HARBOR ACRES SEC 2
A4203772
  • 5 Beds
  • 6 Baths
  • 6,425 SQFT
  • 137 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...

1717 Southpointe Drive

SARASOTA, FL - $5,050,000

Residential, Single Family Home
SOUTHPOINTE SHORES
O5569288
  • 4 Beds
  • 9 Baths
  • 6,883 SQFT
  • 55 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 Terrace

SARASOTA, FL - $4,990,000

Residential, Single Family Home
SAN REMO ESTATES
W7637068
  • 5 Beds
  • 7 Baths
  • 6,710 SQFT
  • 455 DOM
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Built In 2009, Stunning Sarasota Waterfront Property. Prime Location In Desirable West-of-trail San Remo Estates, With Spectacular Bay/inter-coastal Views, Custom 6,700 Sq Ft Home Offers 2 Master Suites With Private Terraces, Plus 3 Guest Suites, ...

1540 Hillview Drive

SARASOTA, FL - $4,950,000

Residential, Single Family Home
HARBOR ACRES SEC 2
A4197272
  • 5 Beds
  • 7 Baths
  • 7,074 SQFT
  • 201 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...

6420 Hollywood Boulevard

SARASOTA, FL - $4,295,000

Residential, Single Family Home
PINE SHORES ESTATES
A4205092
  • 4 Beds
  • 6 Baths
  • 6,878 SQFT
  • 116 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...

1230 N Lake Shore Drive

SARASOTA, FL - $3,890,000

Residential, Single Family Home
OYSTER BAY ESTATES
A4210591
  • 4 Beds
  • 5 Baths
  • 4,111 SQFT
  • 67 DOM
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Public May Remark

1465 Hillview Drive

SARASOTA, FL - $3,815,000

Residential, Single Family Home
HARBOR ACRES SEC 2
A4213441
  • 3 Beds
  • 4 Baths
  • 4,037 SQFT
  • 32 DOM
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Pre-construction. To Be Built. The Sarasota Waterfront Address - Harbor Acres. Build This Luxury Residence On One Of The Largest "estate-sized" Lots In The Neighborhood. A Rarely Available Lot Size - 28,753 Sf, Measuring Approximately 297 X 10...

1352 Harbor Drive

SARASOTA, FL - $3,795,000

Residential, Single Family Home
HARBOR ACRES
A4213434
  • 4 Beds
  • 4 Baths
  • 4,373 SQFT
  • 458 DOM
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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...

1329 Vista Drive

SARASOTA, FL - $3,795,000

Residential, Single Family Home
HARBOR ACRES SEC 2
A4193735
  • 4 Beds
  • 4 Baths
  • 3,762 SQFT
  • 256 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...

1640 Bay Harbor Lane

SARASOTA, FL - $3,499,000

Residential, Single Family Home
STILLWATER ON THE BAY
A4212202
  • 4 Beds
  • 6 Baths
  • 5,093 SQFT
  • 51 DOM
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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...

1503 Blue Heron Drive

SARASOTA, FL - $3,200,000

Residential, Single Family Home
PARADISE SHORES
A4212851
  • 4 Beds
  • 4 Baths
  • 4,518 SQFT
  • 44 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 Boulevard

SARASOTA, FL - $3,199,900

Residential, Single Family Home
PINE SHORES EST 7TH ADD
A4209878
  • 3 Beds
  • 3 Baths
  • 4,738 SQFT
  • 73 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...

1346 Harbor Drive

SARASOTA, FL - $3,000,000

Residential, Single Family Home
HARBOR ACRES
A4203707
  • 4 Beds
  • 4 Baths
  • 3,975 SQFT
  • 137 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...

1449 Hillview Drive

SARASOTA, FL - $2,995,000

Residential, Single Family Home
HARBOR ACRES SEC 2
A4189312
  • 5 Beds
  • 5 Baths
  • 4,982 SQFT
  • 304 DOM
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Exceptional And Incomparable Harbor Acres One Level Residence Was Completely Updated In Coastal Style 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 R...

1581 Hillview Drive

SARASOTA, FL - $2,895,000

Residential, Single Family Home
HARBOR ACRES
A4183577
  • 4 Beds
  • 5 Baths
  • 4,508 SQFT
  • 374 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...

1412 Peregrine Point Drive

SARASOTA, FL - $2,750,000

Residential, Single Family Home
THE LANDINGS
A4201855
  • 5 Beds
  • 5 Baths
  • 6,685 SQFT
  • 115 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 ...

1500 Cunliff Lane

SARASOTA, FL - $2,750,000

Residential, Single Family Home
ACREAGE & UNREC
A4195876
  • 4 Beds
  • 3 Baths
  • 2,803 SQFT
  • 220 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 Drive

SARASOTA, FL - $2,695,000

Residential, Single Family Home
VAMO AMD OF
A4193717
  • 6 Beds
  • 4 Baths
  • 4,121 SQFT
  • 435 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...

1207 N Lake Shore Drive

SARASOTA, FL - $2,595,000

Residential, Single Family Home
OYSTER BAY ESTATES
A4207747
  • 5 Beds
  • 5 Baths
  • 5,043 SQFT
  • 82 DOM
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Absolutely Stunning Waterfront Estate In Exclusive Oyster Bay. Consistently Voted One Of The Most Desired And Exclusive Neighborhoods In All Of Sarasota, This Home Delivers The Quality You Demand In The Location You Deserve. Professionally Renovat...

1235 N Lake Shore Drive

SARASOTA, FL - $2,495,000

Residential, Single Family Home
OYSTER BAY ESTATES
A4213972
  • 4 Beds
  • 3 Baths
  • 3,535 SQFT
  • 35 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...





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 April 25th, 2018 at 8:18am EDT.