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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
  • 75 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...

1486 Hillview Drive

SARASOTA, FL - $13,950,000

Residential, Single Family Residence
HARBOR ACRES SEC 2
A4499907
  • 4 Beds
  • 6 Baths
  • 8,433 SQFT
  • 3 DOM
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One Or More Photo(s) Has Been Virtually Staged. Amid A Canopied Oasis, Resort-like Bliss Awaits You On Sarasota Bay, Surrounded By Magnificent Works Of Nature. Constructed In 2008, The Exquisitely Crafted Estate Pays The Utmost Attention To Elegan...

1400 Ladue Lane

SARASOTA, FL - $6,650,000

Residential, Single Family Residence
NOT PART OF A SUBDIVISION
A4491567
  • 6 Beds
  • 8 Baths
  • 9,052 SQFT
  • 82 DOM
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Herein Lies The Best Waterfront Opportunity That You Will Find In Sarasota. The Seller Is Offering A Flexible Sales Structure To Include Subdividing The Parcel With The Waterfront Lot/home Priced At $5,450,000 And The Easternmost Vacant 17,000+ Sq...

1604 Baywinds Lane

SARASOTA, FL - $6,490,000

Residential, Single Family Residence
BAYWINDS ESTATES
A4482748
  • 4 Beds
  • 7 Baths
  • 5,110 SQFT
  • 186 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 ...

1560 Hillview Drive

SARASOTA, FL - $5,750,000

Residential, Single Family Residence
HARBOR ACRES
A4494473
  • 4 Beds
  • 6 Baths
  • 4,637 SQFT
  • 10 DOM
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Under Construction. Rare Opportunity To Be On The Ground Floor Of A New Build In Harbor Acres. 100 Ft Of Waterfront Overlooking Deep Sailboat Water And Just 3 Houses From The Open Bay Front. Easy Walk To Southside Village Shops And Restaurants. Be...

1423 South Lake Shore Drive

SARASOTA, FL - $4,995,000

Residential, Single Family Residence
OYSTER BAY ESTATES
A4493808
  • 5 Beds
  • 6 Baths
  • 6,739 SQFT
  • 60 DOM
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One Or More Photo(s) Has Been Virtually Staged. Spectacular One-of-a-kind Location And Privacy Close To Downtown Sarasota And Minutes From The Gorgeous Award-winning Siesta Key Beach. A Truly Custom-designed Waterfront Home Built In 2016. 6,793 Sq...

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
  • 96 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...

2320 Wason Road

SARASOTA, FL - $4,200,000

Residential, Single Family Residence
PHILLIPPE PARK
A4499068
  • 4 Beds
  • 5 Baths
  • 4,791 SQFT
  • 8 DOM
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Designed For Relishing The Finer Things In Life While You Entertain Guests And Marvel At The Tranquility Of Water Views, This One-of-a -kind Home Epitomizes A Paradise Lifestyle. Surrounded By 1.8 Acres Of Lush Flora Envying Selbly Gardens, Variou...

1558 Sandpiper Lane

SARASOTA, FL - $4,100,000

Residential, Single Family Residence
PARADISE SHORES
T3294850
  • 4 Beds
  • 4 Baths
  • 4,942 SQFT
  • 58 DOM
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Listing Update: Brand New Barrel Tile Roof 4/2021. This Is A Rare Opportunity For Waterfront Living In Highly Sought Paradise Shores. For The Boating And Watersports Enthusiast, There Is 190 Feet Of Waterfront With A Newer ('19) Seawall, 20,000 L...

1145 North Lake Shore Drive

SARASOTA, FL - $3,650,000

Residential, Single Family Residence
OYSTER BAY ESTATES
A4498214
  • 5 Beds
  • 7 Baths
  • 6,963 SQFT
  • 18 DOM
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**almost 1/2 Acre Bayfront On Roberts Bay Adjacent To Intercoastal Waterway With 100 Feet Of Seawall, Boat Dock, And Boat Lift.** This Estate Size Home(6963sf) Located In The Beloved "oyster Bay" Community Was Built In Two Residences And Later Co...

4414 Westwood Lane

SARASOTA, FL - $3,149,800

Residential, Single Family Residence
OYSTER BAY ESTATES
A4495936
  • 4 Beds
  • 5 Baths
  • 4,531 SQFT
  • 40 DOM
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Pre-construction. To Be Built. This Expansive Lakefront Custom Home Is Situated On An Estate Sized Home Site In Sarasota's Coveted West Of Trail Area. Through A Striking Entry Courtyard, Owners Are Greeted By A Wide Great Room With Expansive Views...

7693 Cove Terrace

SARASOTA, FL - $3,100,000

Residential, Single Family Residence
SOUTHPOINTE SHORES
A4499300
  • 3 Beds
  • 5 Baths
  • 4,636 SQFT
  • 5 DOM
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Sweeping Views Of The Bay And Intercoastal Greet You The Moment You Enter This Beautifully Updated Contemporary Home. Sitting On Almost A Half-acre With 123’ Of Waterfront, Deep Water Dockage, A Brand-new Seawall (2020) And A 16,000lb Lift Plus An...

1561 Blue Heron Drive

SARASOTA, FL - $2,995,000

Residential, Single Family Residence
MCCLELLAN PARK-PARADISE SHORES
A4499148
  • 4 Beds
  • 5 Baths
  • 4,118 SQFT
  • 5 DOM
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Delight In A Downtown Family Lifestyle At This Lovely Four-bedroom Waterfront Home In The Heart Of The City’s Center At Mcclellan Park/paradise Shores. A Low Stone Wall And Lush, Manicured Gardens Frame The Property That Spans More Than A Quarter-...

1865 Clematis Street

SARASOTA, FL - $2,900,000

Residential, Single Family Residence
DESOTA PARK
A4494732
  • 4 Beds
  • 5 Baths
  • 2,990 SQFT
  • 51 DOM
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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 Throughout The Open 2,975-square-foo...

1707 Caribbean Drive

SARASOTA, FL - $2,795,000

Residential, Single Family Residence
CORAL COVE
T3286735
  • 4 Beds
  • 4 Baths
  • 5,012 SQFT
  • 100 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 - $2,750,000

Residential, Single Family Residence
OYSTER BAY ESTATES
A4487508
  • 4 Beds
  • 6 Baths
  • 4,217 SQFT
  • 114 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...

2524 Pleasant Place

SARASOTA, FL - $2,695,000

Residential, Single Family Residence
BAY VIEW HEIGHTS ADD
A4490046
  • 3 Beds
  • 4 Baths
  • 3,399 SQFT
  • 99 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...

1447 Peregrine Point Drive

SARASOTA, FL - $2,350,000

Residential, Single Family Residence
THE LANDINGS
A4472549
  • 5 Beds
  • 7 Baths
  • 8,153 SQFT
  • 295 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...

1802 Magnolia Street

SARASOTA, FL - $2,241,000

Residential, Single Family Residence
POINSETTIA PARK 2
A4492992
  • 5 Beds
  • 6 Baths
  • 4,283 SQFT
  • 68 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...

2330 Mietaw Drive

SARASOTA, FL - $2,195,000

Residential, Single Family Residence
MCCLELLAN PARK
A4494479
  • 5 Beds
  • 3 Baths
  • 3,267 SQFT
  • 54 DOM
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Under Construction. Custom New Construction Home West Of The Trail In Mcclellan Park That Will Be Walking Distance To A Rated Southside School, Close To Great Shops And Restaurants In Southside Village And Minutes To Downtown Sarasota, Siesta Key ...

1851 Oleander Street

SARASOTA, FL - $2,099,000

Residential, Single Family Residence
POINSETTIA PARK 2
A4500086
  • 4 Beds
  • 3 Baths
  • 3,738 SQFT
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This Elegant West Of The Trail Estate Home With Large Homesite Is Located On One Of The Most Attractive Flower Streets. Walking Distance To Southside Elementary, Blocks To Southside Village With Morton's Gourmet Market And Many Local Favorite Rest...





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 May 8th, 2021 at 6:45am EDT.