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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 .... 


"West of the Trail" Homes for Sale by Price

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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1221 Hillview Dr

Sarasota, FL - $7,500,000

Residential, Single Family Home
Harbor Acres
A4434317
  • 4 Beds
  • 4 Baths
  • 4,187 SQFT
  • 29 DOM
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On Sarasota’s Shoreline And Most Desired Address Within Harbor Acres, Discover Unequivocal Excellence – Whether Building New Or Enjoying The Current And Impeccably Updated Residence. Surrounded By Undeniably The Area’s Most Luxurious Homes And As...

1333 Vista Dr

Sarasota, FL - $5,749,000

Residential, Single Family Home
Harbor Acres
A4426157
  • 5 Beds
  • 6 Baths
  • 5,768 SQFT
  • 112 DOM
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Of All Sarasota's Great Neighborhoods, Harbor Acres Is Considered The Best — Best Location, Best Waterfront, Best Appreciation, Best Pedigree, Best Neighbors. Residents Love Being Part Of The Close-knit Community & Being So Close To Downtown Saras...

3544 San Remo Ter

Sarasota, FL - $4,750,000

Residential, Single Family Home
San Remo Estates
A4403580
  • 5 Beds
  • 7 Baths
  • 6,710 SQFT
  • 851 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...

1509 S Lodge Dr

Sarasota, FL - $4,695,000

Residential, Single Family Home
Cherokee Park
A4416416
  • 5 Beds
  • 5 Baths
  • 5,800 SQFT
  • 200 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...

1435 Hillview Dr

Sarasota, FL - $4,595,000

Residential, Single Family Home
Harbor Acres
A4423245
  • 3 Beds
  • 5 Baths
  • 4,876 SQFT
  • 136 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...

1807 Oleander St

Sarasota, FL - $4,499,000

Residential, Single Family Home
0364 Poinsettia Park 2
A4414354
  • 7 Beds
  • 9 Baths
  • 9,492 SQFT
  • 221 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 ...

1404 Kenilworth St

Sarasota, FL - $4,385,000

Residential, Single Family Home
Oyster Bay Landings
A4424301
  • 4 Beds
  • 5 Baths
  • 5,428 SQFT
  • 105 DOM
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Art You Can Live In! World Renowned And Acclaimed Architect, Guy Peterson, Designed Another Modern Masterpiece Of Remarkable Craftsmanship And Pure Minimalist Aesthetic. It All Began With A Vision, An Ambitious Dream To Imagine And Design The Cons...

1430 Harbor Dr

Sarasota, FL - $4,300,000

Residential, Single Family Home
Harbor Acres Sec 2
A4423407
  • 4 Beds
  • 6 Baths
  • 6,631 SQFT
  • 135 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...

1726 Questar Ln

Sarasota, FL - $4,000,000

Residential, Single Family Home
None
A4401320
  • 4 Beds
  • 7 Baths
  • 6,719 SQFT
  • 120 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...

1744 Seminole Dr

Sarasota, FL - $3,995,000

Residential, Single Family Home
Mcclellan Park
A4424752
  • 7 Beds
  • 9 Baths
  • 10.3k SQFT
  • 122 DOM
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Overflowing With Charm, This Custom, Family-inspired Home In The Heart Of Sarasota Is A Rare Find. Completed In 2000, The Traditional Yet Whimsical Architecture Perfectly Complements A Modern Farmhouse Interior That Welcomes You Home. Despite Its ...

7350 Captain Kidd Ave

Sarasota, FL - $3,695,000

Residential, Single Family Home
Buccaneer Bay
A4415503
  • 3 Beds
  • 4 Baths
  • 4,608 SQFT
  • 214 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...

2610 Cardinal Pl

Sarasota, FL - $3,650,000

Residential, Single Family Home
Bay View Heights Add
A4426055
  • 5 Beds
  • 6 Baths
  • 4,605 SQFT
  • 112 DOM
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We Introduce An Exquisite Waterfront Tropical Paradise, Where Panoramic Water Views Surround You. As A Bonus You Will Have No Bridge Traffic To Your New Home Which Makes For Best Location. Upon Entering This Home You Will Be Captivated From The V...

1545 Mallard Ln

Sarasota, FL - $3,650,000

Residential, Single Family Home
Paradise Shores
A4415376
  • 4 Beds
  • 6 Baths
  • 5,279 SQFT
  • 231 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...

1640 Bay Harbor Ln

Sarasota, FL - $3,499,500

Residential, Single Family Home
Stillwater On The Bay
C7410015
  • 4 Beds
  • 6 Baths
  • 5,093 SQFT
  • 137 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...

1352 Harbor Dr

Sarasota, FL - $3,495,000

Residential, Single Family Home
Harbor Acres
A4412879
  • 4 Beds
  • 4 Baths
  • 4,373 SQFT
  • 235 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...

2231 Oriole Dr

Sarasota, FL - $3,495,000

Residential, Single Family Home
Mcclellan Park
A4405569
  • 5 Beds
  • 8 Baths
  • 8,162 SQFT
  • 343 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...

1534 Harbor Pl

Sarasota, FL - $2,995,000

Residential, Single Family Home
Harbor Acres
A4424649
  • 4 Beds
  • 6 Baths
  • 4,056 SQFT
  • 126 DOM
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Under Construction. Under Construction - Another Exceptionally Crafted Home By Coastal Luxury In Collaboration With Jonas Yoder Custom Homes. The Modern Farmhouse Design Will Be On An Oversized Lot In The Exclusive Neighborhood Of Harbor Acres. C...

1655 Bay Harbor Ln

Sarasota, FL - $2,990,000

Residential, Single Family Home
Stillwater On The Bay
A4427443
  • 5 Beds
  • 5 Baths
  • 6,402 SQFT
  • 310 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 ...

1581 Hillview Dr

Sarasota, FL - $2,895,000

Residential, Single Family Home
Harbor Acres
A4183577
  • 4 Beds
  • 5 Baths
  • 4,508 SQFT
  • 771 DOM
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Construction Complete On This Warm Contemporary Home Built By Greenlife Luxury Homes, Offering An Exceptional Level Of Finishes And Attention To Detail. The Dramatic 22’ High Ceiling Allows A Perfect Canvas For Art. The Kitchen Boasts State Of The...

1732 North Dr

Sarasota, FL - $2,850,000

Residential, Single Family Home
Cherokee Park 2
A4432569
  • 5 Beds
  • 5 Baths
  • 4,552 SQFT
  • 42 DOM
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This 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 Half Block From South...

1449 Hillview Dr

Sarasota, FL - $2,550,000

Residential, Single Family Home
Harbor Acres Sec 2
A4407215
  • 4 Beds
  • 5 Baths
  • 4,982 SQFT
  • 694 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...





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 May 24th, 2019 at 7:45pm EDT.