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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
  • 273 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...

1364 Harbor Dr

Sarasota, FL - $6,995,000

Residential, Single Family Home
Harbor Acres
A4450162
  • 5 Beds
  • 6 Baths
  • 5,244 SQFT
  • 79 DOM
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Hailed As One Of The Best Lots In Harbor Acres, Spectacular Direct Views Of Sarasota Bay, John Ringling Bridge, Downtown’s Cityscape And Sights Of Sailboats Abound Around Every Corner Of This Five-bedroom Estate. Chic Upgrades, High-end Finishes A...

1814 Roland St

Sarasota, FL - $6,500,000

Residential, Single Family Home
Cedar Cove
A4452913
  • 6 Beds
  • 9 Baths
  • 10.6k SQFT
  • 44 DOM
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Weave Your Way Up To This Unassumingly Majestic ~2.5 Acre Gated Residence On Wide Water Of Sarasota’s Tranquil Intracoastal Waterway And Discover Easy Elegance And Coastal Comfort. Just Paces From The South Bridge Over To Siesta Key Sand, This Inv...

1441 Rebecca Ln

Sarasota, FL - $4,650,000

Residential, Single Family Home
Oyster Bay Landings
A4455314
  • 4 Beds
  • 6 Baths
  • 5,889 SQFT
  • 8 DOM
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Inspired Coastal Design. Located In The Private Gated Enclave Of Oyster Bay Landings, This Amazing Waterfront Residence Combines Unique Architecture And Incredible Interior Design To Create A Stunning Yet Comfortable And Functional Home. Set On A ...

3544 San Remo Ter

Sarasota, FL - $4,590,000

Residential, Single Family Home
San Remo Estates
W7819412
  • 5 Beds
  • 7 Baths
  • 6,710 SQFT
  • 1,041 DOM
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Stunning Sarasota Waterfront Property. Prime Location In Desirable West-of-trail San Remo Estates, With Spectacular Bay/inter-coastal Views, This Custom Built 6,700 Sq Ft Home Offers 2 Master Suites With Private Terraces, Plus 3 Guest Suites, 2 Ad...

1807 Oleander St

Sarasota, FL - $4,499,000

Residential, Single Family Home
0364 Poinsettia Park 2
A4414354
  • 7 Beds
  • 9 Baths
  • 9,492 SQFT
  • 423 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 ...

1525 Mallard Ln

Sarasota, FL - $4,100,000

Residential, Single Family Home
Paradise Shores
A4443475
  • 5 Beds
  • 6 Baths
  • 4,781 SQFT
  • 163 DOM
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Under Construction. Perfectly Sited On 123 Feet Of Protected Yacht Basin And The 3rd House In From The Open Bay Is Another Vision Of Beauty And Functionality From Notable Luxury Builder, Allegra Homes. This Stunning 2-story Residence Will Feature ...

1516 Sandpiper Ln

Sarasota, FL - $3,999,999

Residential, Single Family Home
Paradise Shores
A4442067
  • 5 Beds
  • 6 Baths
  • 5,014 SQFT
  • 181 DOM
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Newly Built. This Coastal Residence Captivates With Its Impeccably Designed Décor And Outdoor Living Spaces In A Scenic Waterfront Setting Only Seconds To The Open Waters Of Sarasota Bay. Located West Of Trail, Sandpiper Is A Quiet Street Situated...

6420 Hollywood Blvd

Sarasota, FL - $3,790,000

Residential, Single Family Home
Pine Shores Estates
A4449708
  • 5 Beds
  • 6 Baths
  • 6,878 SQFT
  • 64 DOM
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Unobstructed Bay Views And Endless Sunsets Are Just The Beginning For This Incredible Custom Estate. Completely Walled And Gated, This Bayfront Home Is Sited At The End Of A Quiet Tree-lined Street With Just Over 300 Feet Of Water Frontage. Its Ne...

1545 Hillview Dr

Sarasota, FL - $3,550,000

Residential, Single Family Home
Harbor Acres
A4449105
  • 4 Beds
  • 5 Baths
  • 4,625 SQFT
  • 97 DOM
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Extraordinary Estate Located In One Of Sarasota's Most Coveted Neighborhoods… Harbor Acres. This Premier Waterfront Property Features Two Levels Of Luxurious Living Offering Four Bedrooms, Four-and-a-half Baths, Library/den, Formal Dining, Chef’s ...

2610 Cardinal Pl

Sarasota, FL - $3,500,000

Residential, Single Family Home
Bay View Heights Add
A4426055
  • 5 Beds
  • 6 Baths
  • 4,605 SQFT
  • 316 DOM
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Introducing An Exquisite Waterfront, Tropical Paradise Where Panoramic Views Surround You. Tucked Behind The Barrier Islands With Your Own Dock And 16,000 Lbs. Boat Lift, The Home Offers Privacy With A View Over Open Water, Glistening Lights Refle...

1352 Harbor Dr

Sarasota, FL - $3,449,000

Residential, Single Family Home
Harbor Acres
A4447026
  • 4 Beds
  • 4 Baths
  • 4,373 SQFT
  • 108 DOM
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The Best Of Luxurious Waterfront Living At This Stunning, Newer Harbor Acres Home! Perfectly Positioned Just A Few Lots In From The Open Bayfront, Abounding In Impeccable Views Of Sarasota Bay And John Ringling Bridge From Nearly Every Room Of Thi...

1640 Bay Harbor Ln

Sarasota, FL - $3,449,000

Residential, Single Family Home
Stillwater On The Bay
C7410015
  • 4 Beds
  • 6 Baths
  • 5,093 SQFT
  • 381 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 - $3,295,000

Residential, Single Family Home
Mcclellan Park
A4449326
  • 5 Beds
  • 8 Baths
  • 8,162 SQFT
  • 87 DOM
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Price Based On Appraised Value. Enjoy Comfort, Style, And Functional Design In This Impressive “west Of Trail” Home. Sited On An Oversized Lot In Mcclellan Park, One Of The Area’s Most Sought After Neighborhoods, This Residence Offers A Little Som...

6438 Hollywood Blvd

Sarasota, FL - $3,099,900

Residential, Single Family Home
Pine Shores Estate 7th Sec
A4449895
  • 3 Beds
  • 4 Baths
  • 4,282 SQFT
  • 70 DOM
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Styled After The French Residences Of New Orleans, This Magnificent Waterfront Home Aptly Named Coucher Du Soleil Simply Translates As "sunset." Glorious Views Of Little Sarasota Bay, Siesta Key, And Daily Sunsets Welcome You From Every Room Of Th...

1562 South Dr

Sarasota, FL - $2,999,000

Residential, Single Family Home
Cherokee Park 2
A4452303
  • 6 Beds
  • 6 Baths
  • 5,944 SQFT
  • 62 DOM
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Arguably, One Of The Most Classic And Unique Homes To Come On The Market In Sarasota County In Years. Located On A Double Lot (almost 3/4 Of An Acre) At The End Of A Dead-end Street In The Historic And Iconic Cherokee Park Neighborhood Sits A 5900...

1522 N Lake Shore Dr

Sarasota, FL - $2,995,000

Residential, Single Family Home
Oyster Bay Estates
A4442286
  • 4 Beds
  • 5 Baths
  • 4,783 SQFT
  • 176 DOM
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Tucked Away On Lakeshore Drive In A Storybook Lakefront Setting, This Exquisite Estate Embodies Tropical Elegance And Style. Luxurious Appointments, State-of-the-art Amenities, And A Romantic Water View Present An Artful Backdrop For Living. Beaut...

1534 Harbor Pl

Sarasota, FL - $2,995,000

Residential, Single Family Home
Harbor Acres
A4424649
  • 4 Beds
  • 6 Baths
  • 3,652 SQFT
  • 370 DOM
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Under Construction. Under Construction - Watch It Rise, Construction Is Underway! 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...

1658 Hawthorne St

Sarasota, FL - $2,495,000

Residential, Single Family Home
Lewis Combs Sub
A4451948
  • 3 Beds
  • 4 Baths
  • 2,939 SQFT
  • 66 DOM
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Nestled West Of The Trail In One Of The Most Sought-after Neighborhoods In Sarasota Is A Symphony Of Glass, Steel, And Concrete Woven Together With Light, Water And Natural Elements. This Poetic 3-bedroom Residence Was Designed By Architect Guy Pe...

1555 Sandpiper Ln

Sarasota, FL - $2,450,000

Residential, Single Family Home
Paradise Shores
A4436047
  • 5 Beds
  • 4 Baths
  • 3,498 SQFT
  • 252 DOM
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Under Construction. Master Builder Allegra Homes Expanded Two-story “gloria” Plan Infused With An Atmosphere Of Sophistication And Refinement. This 3,870-square-foot Residence Is Irresistible With 4 Bedrooms, 4 Baths, 4-car Garage, Bonus Room, Fab...

1818 N Lake Shore Dr

Sarasota, FL - $2,449,000

Residential, Single Family Home
Oyster Bay Estates
A4454495
  • 4 Beds
  • 6 Baths
  • 5,968 SQFT
  • 91 DOM
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Set In Oyster Bay Estates And Remarkable In Every Way Is Villa Lidia, A Stunning Example Of Architectural Mastery And Creatively Imagined By Acclaimed Architect Thorning Little. Impressive In Both Indoor And Outdoor Living Space As Well As Its Cla...





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 DBA Stellar MLS.

Listing information last updated on January 24th, 2020 at 8:15am EST.