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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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1309 Vista Drive

SARASOTA, FL - $18,000,000

Residential, Single Family Residence
HARBOR ACRES SEC 2
A4491997
  • 3 Beds
  • 6 Baths
  • 8,452 SQFT
  • 10 DOM
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Rarely Has Such An Unprecedented Opportunity Come Available For The Most Discerning Buyer In Search Of A Private Waterfront Gated Estate In Harbor Acres, A Premier Established Neighborhood Set On Sarasota’s Bay. An Architectural Masterpiece Set On...

1400 Ladue Lane

SARASOTA, FL - $7,850,000

Residential, Single Family Residence
NOT PART OF A SUBDIVISION
A4491567
  • 6 Beds
  • 8 Baths
  • 9,052 SQFT
  • 17 DOM
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A Storied Setting With Wide Open Bay Views And A Picturesque Boat House In The Ever-popular Field Club Area Is Comprised Of Over 1.2 Acres And 112.5 Feet Of Shoreline. This Gated Property Located At The End Of Ladue Ln. Represents A Great Opportun...

1604 Baywinds Lane

SARASOTA, FL - $6,490,000

Residential, Single Family Residence
BAYWINDS ESTATES
A4482748
  • 4 Beds
  • 7 Baths
  • 5,110 SQFT
  • 121 DOM
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This Magnificent Waterfront Estate Sits On Over 300 Feet Of Shoreline On Little Sarasota Bay And Offers Sweeping Views From Nearly Every Room. This Custom Home Was Built In 2018 And Offers Unparalleled Privacy, Views Over The Open Water, And Your ...

1640 Bay Harbor Lane

SARASOTA, FL - $4,495,000

Residential, Single Family Residence
STILLWATER ON THE BAY
A4490114
  • 4 Beds
  • 6 Baths
  • 5,093 SQFT
  • 31 DOM
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Come Live The Florida Lifestyle To Its Fullest In This Magnificent Mediterranean Style Waterfront Home Located Behind The Gates Of The Much Sought After Enclave Of Stillwater On The Bay. Luxurious, Elegant, With A Great Amount Of Opulence But Ye...

1807 Oleander Street

SARASOTA, FL - $4,399,000

Residential, Single Family Residence
POINSETTIA PARK
A4475067
  • 5 Beds
  • 9 Baths
  • 9,492 SQFT
  • 204 DOM
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Transport Yourself To The Countryside Of France Where You May Ensconce Yourself Behind The Ivy-covered Walls Of This Gated Multi-level French Chateau Amidst The Most Glorious Selection Of Plantings Anywhere. A Graceful Display Of Architectural Det...

1620 North Lodge Drive

SARASOTA, FL - $3,500,000

Residential, Single Family Residence
CHEROKEE LODGE
A4493153
  • 5 Beds
  • 4 Baths
  • 4,660 SQFT
  • 2 DOM
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Cherokee Park Waterfront House. This House Is One Of The Few With Water Access In This Sought After Neighborhood. Located 5 Houses From The Open Bay. House Sits On 1.5 Buildable Lots Totaling 26,813 Sf. There Is An Unique Opportunity To Purcha...

1610 North Lodge Drive

SARASOTA, FL - $3,500,000

Residential, Single Family Residence
CHEROKEE LODGE
A4493094
  • 6 Beds
  • 5 Baths
  • 3,057 SQFT
  • 2 DOM
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Cherokee Park Waterfront House. This House Is One Of The Few With Water Access In This Sought After Neighborhood. Located 4 Houses From The Open Bay. House Sits On 1.5 Buildable Lots Totaling 25,394 Sf. There Is An Unique Opportunity To Purcha...

2524 Pleasant Place

SARASOTA, FL - $2,850,000

Residential, Single Family Residence
BAY VIEW HEIGHTS ADD
A4490046
  • 3 Beds
  • 4 Baths
  • 3,399 SQFT
  • 34 DOM
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Welcome Home To This Spectacular Contemporary/coastal 3 Bedroom, 3.5 Bath Plus Office Home, Designed By Award-winning Dsdg Architects, Masterfully-built With Countless Customizations, And Beautifully Sited On A Picture-perfect Street In Bay View H...

1707 Caribbean Drive

SARASOTA, FL - $2,795,000

Residential, Single Family Residence
CORAL COVE
T3286735
  • 4 Beds
  • 4 Baths
  • 5,012 SQFT
  • 37 DOM
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A Property Such As This Does Not Come Onto The Market Often. A Jewel, Perfectly Located In One Of Sarasota's Most Sought After “west Of The Trail” Waterfront Communities, Coral Cove. Elegant Custom Waterfront Home, With Over 5,000 Square Feet Of ...

1421 North Lake Shore Drive

SARASOTA, FL - $2,595,000

Residential, Single Family Residence
OYSTER BAY ESTATES
A4487508
  • 4 Beds
  • 6 Baths
  • 4,217 SQFT
  • 49 DOM
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Under Construction. Currently Under Construction By Renowned, Award-winning Platinum Coast Construction With Expected Completion Summer 2021, This Modern Masterpiece Has Been Planned With Uncompromising Detail, Meticulous Attention To Architectura...

1518 Eastbrook Drive

SARASOTA, FL - $2,590,000

Residential, Single Family Residence
KENTWOOD ESTATES
A4490571
  • 4 Beds
  • 5 Baths
  • 3,884 SQFT
  • 28 DOM
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Pre-construction. To Be Built. The Martinique By Heritage Builders Is A Stunning Home Located On One Of The Oyster Bay Area's Most Desirable Streets, Eastbrook Drive. As You Approach The Clean Coastal Cottage Inspired Martinique, You Are Greeted B...

1447 Peregrine Point Drive

SARASOTA, FL - $2,400,000

Residential, Single Family Residence
THE LANDINGS
A4472549
  • 5 Beds
  • 7 Baths
  • 8,153 SQFT
  • 230 DOM
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Perfectly Situated On A Quiet Culdesac, This Exquisite Home Boasts Over 8,000 Square Feet Of Living Area. As You Approach This Custom Traditional Home, The Circular Drive, Lush Landscaping And Grand Entrance Will Take Your Breath Away. As You Ente...

1235 North Lake Shore Drive

SARASOTA, FL - $2,300,000

Residential, Single Family Residence
OYSTER BAY ESTATES
A4491607
  • 4 Beds
  • 3 Baths
  • 3,535 SQFT
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This Oyster Bay Home Sits In An Idyllic Quiet Cul-de-sac Of The Highly Sought After Oyster Bay Estates Community, Which Sits Just West Of Tamiami Trail And Mere Blocks South Of Siesta Key Drive. This Mediterranean Home Boasts Dual Views Of Saraso...

1554 Eastbrook Drive

SARASOTA, FL - $2,297,955

Residential, Single Family Residence
KENTWOOD ESTATES
A4487930
  • 3 Beds
  • 5 Baths
  • 2,975 SQFT
  • 55 DOM
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Pre-construction. To Be Built. Another Dazzling Display Of Award-winning Design And Construction To Be Built By The Notable Custom Homebuilding Team At Allegra Homes. Presenting The 2021 “kristi Ann” Model With An Exciting Array Of Amenities Throu...

4110 Camino Real Drive

SARASOTA, FL - $2,199,000

Residential, Single Family Residence
WESTBROOK
A4480796
  • 4 Beds
  • 5 Baths
  • 3,604 SQFT
  • 142 DOM
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Under Construction. Projected Completion By Summer Of 2021. Location And Luxury Meet On This Coastal Contemporary Home In The Exclusive Oyster Bay Area. This 4 Bedroom ( Could Easily Be A 5 Bedroom) 4.5 Bath Home Being Constructed By The Holli...

1427 Cedar Bay Lane

SARASOTA, FL - $1,999,995

Residential, Single Family Residence
THE LANDINGS
A4408881
  • 5 Beds
  • 6 Baths
  • 6,083 SQFT
  • 954 DOM
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Set In The Private, Gated Community Of The Landings With Views Over The Bay, This 5-bedroom Plus Den, 5.5-bath Family Home Is The Epitome Of Grand! From The Vaulted Entrance Hall, With Wooden Floors Inlaid With Marble, Opening Out To The Grandeur ...

1802 Magnolia Street

SARASOTA, FL - $1,999,900

Residential, Single Family Residence
POINSETTIA PARK 2
A4492992
  • 5 Beds
  • 6 Baths
  • 4,283 SQFT
  • 3 DOM
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One Of A Kind Coastal Farmhouse From One Of Tampa Bay's Premier Boutique Builders,"gray Family Homes". This Home Is Unlike Anything Else In The Area. This West Of Trail Home Is Just A Few Blocks From Southside Elementary And It Includes A Long Li...

2146 Mcclellan Parkway

SARASOTA, FL - $1,925,000

Residential, Single Family Residence
MCCLELLAN PARK RESUB
A4476936
  • 3 Beds
  • 4 Baths
  • 2,538 SQFT
  • 185 DOM
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Under Construction. Another Courtyard Simply Modern Design. West Of The Trail Address. Southside School. Walking Distance To Everything! Sarasota School Of Architecture Inspired Simply Modern Home... Concrete Tiled Flooring Throughout, Gorgeous Li...

1712 Shoreland Drive

SARASOTA, FL - $1,890,000

Residential, Single Family Residence
SHORELAND WOODS SUB
A4487530
  • 3 Beds
  • 4 Baths
  • 2,839 SQFT
  • 55 DOM
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Pre-construction. To Be Built. Awarding Winning Allegra Homes In The Sought After Area Of West Of Trail. Near The Gateway To World Famous Siesta Key, This One Level Home With 3 Car Garage Is Florida Living At Its Finest. Soaring Ceiling In The Liv...

1722 Shoreland Drive

SARASOTA, FL - $1,750,000

Residential, Single Family Residence
WEST OF TRAIL
A4485575
  • 5 Beds
  • 4 Baths
  • 3,790 SQFT
  • 87 DOM
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This Stunning, 2017 Built Modern Home Is Located In Sarasota’s Hottest Neighborhood- West Of Trail. Featuring Easy Access To The Legendary Gulf Beaches, The Sophistication Of Downtown Sarasota, And The Coveted Southside School District, You’ll Fal...

7767 Holiday Drive N

SARASOTA, FL - $1,750,000

Residential, Single Family Residence
HOLIDAY HARBOR
A4437534
  • 4 Beds
  • 3 Baths
  • 2,895 SQFT
  • 618 DOM
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Holiday Harbor New Construction Just Completed! West Indies Ranch Styled Home On Salt Water Canal To Sarasota Bay Leading To The Gulf Of Mexico. Dock Your Boat In Your Backyard Where There Is A Dock To Accommodate Your Boat Lift, Or Keep It At Th...





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 March 4th, 2021 at 11:09am EST.