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 ListingsUnder $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$1,000,000 - $1,250,000
$1,250,000 - $1,500,000$1,500,000 - $1,750,000$1,750,000 - $2,000,000
$2,000,000 - $3,000,000$3,000,000 - $4,000,000$4,000,000 - $5,000,000
Over $5,000,000
431 Properties Found. Showing Page 1 of 21
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Under Construction. Inspired By The Understated...

$6,249,000
Sarasota, FL
5 br, 6 ba, 5,738 ft² Harbor Acres Sec 2 Residential
Address:
1333 Vista Dr
Price:
$6,249,000
City:
Sarasota
Beds:
5
Baths:
6
Subdivision:
Harbor Acres Sec 2
Type:
Residential
MLS® #:
O5446820

Under Construction. Inspired By The Understated Luxury Of A Caribbean Villa, This Brand New, Two-...

Photo of Listing #O5446820

Set In A Commanding Waterfront Location On Hill...

$5,595,000
Sarasota, FL
5 br, 7 ba, 7,074 ft² Harbor Acres Sec 2 Residential
Address:
1540 Hillview Dr
Price:
$5,595,000
City:
Sarasota
Beds:
5
Baths:
7
Subdivision:
Harbor Acres Sec 2
Type:
Residential
MLS® #:
A4197272

Set In A Commanding Waterfront Location On Hillview Drive, One Of The Most Prized Addresses In Sa...

Photo of Listing #A4197272

Stunning Sarasota Waterfront Property. Prime Lo...

$4,890,000
Sarasota, FL
5 br, 7 ba, 6,710 ft² San Remo Estates Residential
Address:
3544 San Remo Ter
Price:
$4,890,000
City:
Sarasota
Beds:
5
Baths:
7
Subdivision:
San Remo Estates
Type:
Residential
MLS® #:
A4174958

Stunning Sarasota Waterfront Property. Prime Location In Desirable West-of-trail San Remo Estates...

Photo of Listing #A4174958

Designer Finishes, Thoughtful Decor And Custom ...

$4,695,000
Sarasota, FL
5 br, 6 ba, 5,491 ft² Harbor Acres Sec 2 Residential
Address:
1505 Hillview Dr
Price:
$4,695,000
City:
Sarasota
Beds:
5
Baths:
6
Subdivision:
Harbor Acres Sec 2
Type:
Residential
MLS® #:
A4197135

Designer Finishes, Thoughtful Decor And Custom Construction Built To The Highest Standards Are Th...

Photo of Listing #A4197135

Located In Sarasota’s Favorite Mainland Baysi...

$3,995,000
Sarasota, FL
3 br, 4 ba, 4,373 ft² Harbor Acres Residential
Address:
1352 Harbor Dr
Price:
$3,995,000
City:
Sarasota
Beds:
3
Baths:
4
Subdivision:
Harbor Acres
Type:
Residential
MLS® #:
A4174153

Located In Sarasota’s Favorite Mainland Bayside Neighborhood Of Harbor Acres, This Gracious Hom...

Photo of Listing #A4174153

Looking For A Peaceful Home On A Large Lot, Ove...

$3,795,000
Sarasota, FL
4 br, 4 ba, 3,762 ft² Harbor Acres Sec 2 Residential
Address:
1329 Vista Dr
Price:
$3,795,000
City:
Sarasota
Beds:
4
Baths:
4
Subdivision:
Harbor Acres Sec 2
Type:
Residential
MLS® #:
A4193735

Looking For A Peaceful Home On A Large Lot, Overlooking The Boat Basin In Harbor Acres? One That ...

Photo of Listing #A4193735

A Gorgeous Waterfront Estate Located In The Des...

$3,793,000
Sarasota, FL
5 br, 6 ba, 6,101 ft² Harbor Acres Residential
Address:
1344 Harbor Dr
Price:
$3,793,000
City:
Sarasota
Beds:
5
Baths:
6
Subdivision:
Harbor Acres
Type:
Residential
MLS® #:
A4187925

A Gorgeous Waterfront Estate Located In The Desirable Bayfront Community Of Harbor Acres—saraso...

Photo of Listing #A4187925

Exceptional And Incomparable Harbor Acres One L...

$3,495,000
Sarasota, FL
5 br, 5 ba, 4,982 ft² Harbor Acres Sec 2 Residential
Address:
1449 Hillview Dr
Price:
$3,495,000
City:
Sarasota
Beds:
5
Baths:
5
Subdivision:
Harbor Acres Sec 2
Type:
Residential
MLS® #:
A4189312

Exceptional And Incomparable Harbor Acres One Level Residence Was Completely Updated In 2015 For...

Photo of Listing #A4189312

Possibly One Of The Finest Views Of Sarasota Ba...

$3,399,000
Sarasota, FL
4 br, 5 ba, 4,797 ft² Southpointe Shores Unit 2 Residential
Address:
7697 Cove Ter
Price:
$3,399,000
City:
Sarasota
Beds:
4
Baths:
5
Subdivision:
Southpointe Shores Unit 2
Type:
Residential
MLS® #:
A4185483

Possibly One Of The Finest Views Of Sarasota Bay, This Spectacular Gated Boating Estate Offers St...

Photo of Listing #A4185483

Experience A Life Of Sheer Waterfront Serenity ...

$3,250,000
Sarasota, FL
6 br, 4 ba, 4,121 ft² Vamo Amd Of Residential
Address:
1710 Vamo Dr
Price:
$3,250,000
City:
Sarasota
Beds:
6
Baths:
4
Subdivision:
Vamo Amd Of
Type:
Residential
MLS® #:
A4193717

Experience A Life Of Sheer Waterfront Serenity On Over 2 Pristine Acres In Sarasota. This Park-li...

Photo of Listing #A4193717

Perfectly Positioned For Maximum Enjoyment Of E...

$3,250,000
Sarasota, FL
5 br, 6 ba, 6,216 ft² Aqualane Estates 2nd Residential
Address:
1616 Stanford Ln
Price:
$3,250,000
City:
Sarasota
Beds:
5
Baths:
6
Subdivision:
Aqualane Estates 2nd
Type:
Residential
MLS® #:
A4177657

Perfectly Positioned For Maximum Enjoyment Of Everything Sarasota, This Remarkable Gated Mainland...

Photo of Listing #A4177657

Rarely Available Property On Almost Half Acre L...

$2,950,000
Sarasota, FL
4 br, 3 ba, 2,803 ft² Acreage & Unrec Residential
Address:
1500 Cunliff Ln
Price:
$2,950,000
City:
Sarasota
Beds:
4
Baths:
3
Subdivision:
Acreage & Unrec
Type:
Residential
MLS® #:
A4195876

Rarely Available Property On Almost Half Acre Lot With Panoramic Bay Views, To The South Siesta K...

Photo of Listing #A4195876

This Under Construction Home Is The Ultimate Il...

$2,700,000
Sarasota, FL
5 br, 5 ba, 4,468 ft² Cherokee Park 2 Residential
Address:
1732 North Dr
Price:
$2,700,000
City:
Sarasota
Beds:
5
Baths:
5
Subdivision:
Cherokee Park 2
Type:
Residential
MLS® #:
A4191053

This Under Construction Home Is The Ultimate Illustration Of British West Indies, Nestled On A Ma...

Photo of Listing #A4191053

Nestled Beautifully In Sarasota’s Most Covete...

$2,600,000
Sarasota, FL
4 br, 4 ba, 4,400 ft² Oyster Bay Residential
Address:
4509 Camino Real
Price:
$2,600,000
City:
Sarasota
Beds:
4
Baths:
4
Subdivision:
Oyster Bay
Type:
Residential
MLS® #:
A4185342

Nestled Beautifully In Sarasota’s Most Coveted Location, West Of The Trail, This Distinctive Ho...

Photo of Listing #A4185342

All About Location, All About Lifestyle, All Ab...

$2,499,900
Sarasota, FL
4 br, 4 ba, 4,750 ft² Harbor Acres Residential
Address:
1508 Flower Dr
Price:
$2,499,900
City:
Sarasota
Beds:
4
Baths:
4
Subdivision:
Harbor Acres
Type:
Residential
MLS® #:
A4198894

All About Location, All About Lifestyle, All About Comfort. Harbor Acres Is Probably The Most Env...

Photo of Listing #A4198894

Pre-construction. To Be Built. New Construction...

$2,495,000
Sarasota, FL
4 br, 4 ba, 4,108 ft² Harbor Acres Residential
Address:
1581 Hillview Dr
Price:
$2,495,000
City:
Sarasota
Beds:
4
Baths:
4
Subdivision:
Harbor Acres
Type:
Residential
MLS® #:
A4183577

Pre-construction. To Be Built. New Construction In Harbor Acres, One Of The Most Sought After And...

Photo of Listing #A4183577

Masterful Design And Modern Luxury Are Uniquely...

$2,395,000
Sarasota, FL
4 br, 3 ba, 3,372 ft² Holiday Harbor Residential
Address:
7794 Holiday Dr N
Price:
$2,395,000
City:
Sarasota
Beds:
4
Baths:
3
Subdivision:
Holiday Harbor
Type:
Residential
MLS® #:
A4156411

Masterful Design And Modern Luxury Are Uniquely Embodied In This 4 Bedroom 3 Bath Home. This Wate...

Photo of Listing #A4156411

Pre-construction To Be Built - Opportunities Li...

$2,300,000
Sarasota, FL
4 br, 4 ba, 3,100 ft² N/a Residential
Address:
1620 Memory Ln
Price:
$2,300,000
City:
Sarasota
Beds:
4
Baths:
4
Subdivision:
N/a
Type:
Residential
MLS® #:
A4195911

Pre-construction To Be Built - Opportunities Like This Are Rare Indeed. A Brand New Custom Home B...

Photo of Listing #A4195911

Located On Little Sarasota Bay, The View From T...

$2,295,000
Sarasota, FL
4 br, 4 ba, 4,195 ft² Baywood Colony Westport Sec 2 Residential
Address:
5816 Tidewood Ave
Price:
$2,295,000
City:
Sarasota
Beds:
4
Baths:
4
Subdivision:
Baywood Colony Westport Sec 2
Type:
Residential
MLS® #:
A4180808

Located On Little Sarasota Bay, The View From This West Facing Home Provides Magnificent Sunsets ...

Photo of Listing #A4180808

This Is A Rare Opportunity To Live On A Private...

$2,250,000
Sarasota, FL
3 br, 3 ba, 2,582 ft² Oyster Bay Landings Residential
Address:
1400 Kenilworth St
Price:
$2,250,000
City:
Sarasota
Beds:
3
Baths:
3
Subdivision:
Oyster Bay Landings
Type:
Residential
MLS® #:
A4191231

This Is A Rare Opportunity To Live On A Private Peninsula In Oyster Bay Landings, A Gated Communi...

Photo of Listing #A4191231

Beautiful Lake Front Address In Oyster Bay! Woo...

$2,250,000
Sarasota, FL
3 br, 4 ba, 4,642 ft² Oyster Bay Estates Residential
Address:
1615 S Lake Shore Dr
Price:
$2,250,000
City:
Sarasota
Beds:
3
Baths:
4
Subdivision:
Oyster Bay Estates
Type:
Residential
MLS® #:
A4198495

Beautiful Lake Front Address In Oyster Bay! Wooded Setting With Tall Pines And Old Oaks On Over ...

Photo of Listing #A4198495


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 October 24th, 2017 at 1:33am EDT.