West of Trail Luxury Homes For Sale

Below are some of the most lavish homes available in Sarasota, Florida. West of the Trail neighborhoods are highly sought after for their charm, convenience and diversity. Some of the most expensive Sarasota real estate is found in these communities. Check back often as this website is updated every 15 minutes with the latest information from our MLS.

Luxury Homes for Sale West of Trail Sarasota

All Listings Over $1,000,000
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50 W Bay St, Osprey $3,680,000

  • 7 Beds
  • 7.0 Baths
  • 6,659 SqFt
  • 3.68 Acres

Discover A Once-in-a-lifetime Opportunity To Restore, Build, Or Develop On 3.68 Acres Directly On Sarasota Bay In Scenic, Historic Osprey Just South Of The Oaks. Dating Back To The Late 1800's And Known As One Of The First Properties To Be Settled, This Swe...

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1337 Vista Dr, Sarasota $3,150,000

  • 0.64 Acres

Amazing Premier Waterfront Estate Lot On Beautiful Vista Drive In Harbor Acres With Deep Water Dockage And A Permanent Sight Line Easement Allowing For Breathtaking Views Of The Yacht Basin, Bay And Ringling Bridge. Truly One Of The Finest Parcels Of Land I...

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3850 Tangier (lot 15) Ter, Sarasota $2,000,000

  • 0.79 Acres

Build Your Dream Home On This Beautiful Corner Lot In San Remo Estates (the Largest Lot In The Subdivision) With 100.75 Feet Of Frontage On The San Remo Sailboat Basin. Gorgeous Twin Banyan Trees In The Front Can Be Circled By A Driveway Which Will Give You...

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1400 Kenilworth St, Sarasota $2,250,000

  • 3 Beds
  • 3.0 Baths
  • 2,582 SqFt
  • 0.43 Acres

This Is A Rare Opportunity To Live On A Private Peninsula In Oyster Bay Landings, A Gated Community West Of Trail In Sarasota’s Exclusive Oyster Bay. Secluded, Quiet And Surrounded By Water, This One-of-a-kind Property Is A Haven Of Peace And Relaxation. Th...

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1400 Kenilworth St, Sarasota $2,250,000

  • 0.43 Acres

A Rare Opportunity To Purchase A Private Peninsula In Oyster Bay Landings, A Gated Community West Of Trail In Sarasota’s Exclusive Oyster Bay. Secluded, Quiet And Surrounded By Water, This One-of-a-kind Property Is A Haven Of Peace And Relaxation. The Prope...

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1874 Oleander St, Sarasota $1,495,000

  • 5 Beds
  • 4.0 Baths
  • 3,823 SqFt
  • 0.27 Acres

Fantastic West-of-trail Home...walk To "a" Rated Southside School! Wonderful Like-new Home, Built In 2008 With High-end Finishes And Attention To Detail! Hardwood Floors, One Consistent Paint Color, Volume Ceilings, Eight Foot Solid Wood Doors And Quality...

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1955 Oleander St, Sarasota $1,349,500

  • 3 Beds
  • 2.0 Baths
  • 2,470 SqFt
  • 0.27 Acres

Under Construction.....by Allegra Homes. Introducing The Buccaneer, A Modern One Story Home In Sarasota's Most Sought After Location, West Of Trail. Home Under Final Design, Please Call For Plan. This Open Concept Home Will Be Finished February/march Of 2...

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95 Osprey Point Dr, Osprey $2,250,000

  • 5 Beds
  • 6.0 Baths
  • 7,500 SqFt
  • 0.74 Acres

French Chateaux With Guest House And 4+ (tandum) Car Garage In The Oaks Bayside. This Incredible Bo Macewen Designed Masterpiece Was Finished In 1997 And Major Renovations Were Done In 2001. As You Enter The Main House You Are Met With A Spectacular Wooden ...

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1732 North Dr, Sarasota $2,700,000

  • 5 Beds
  • 5.0 Baths
  • 4,468 SqFt
  • 0.34 Acres

This Under Construction 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 F...

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1233 N Gulfstream Ave #1403, Sarasota $1,290,000

  • 2 Beds
  • 3.0 Baths
  • 2,035 SqFt

Enjoy Life In This Urban Oasis High In The Sky From This Signature Downtown Building With Panoramic Views Of Island Park, Sarasota Bay And The Gulf Of Mexico Past The Barrier Islands. Entering The Foyer With A Starlight Ceiling Sets The Stage. The Expansive...

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1654 Landings Blvd, Sarasota $2,195,000

  • 5 Beds
  • 8.0 Baths
  • 6,531 SqFt
  • 0.42 Acres

The Newer Smart Home Features Offered At This Stunning Traditional-style, 6-bedroom Estate, Create A Level Of Convenient Luxury For The Modern Family, Providing Access To Everything At The Touch Of A Button. Situated On More Than A Quarter-acre In A Prime L...

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505 S Orange Ave #1503, Sarasota $1,675,000

  • 3 Beds
  • 4.0 Baths
  • 3,003 SqFt

Spacious Penthouse With One Of The Best Views In Downtown Sarasota! The Unit Is In The Final Phases Of An Extensive Updating. The Updating Will Be Complete On Or About The First Week Of August. I Will Be Adding Updated Pictures As To The Progress Every Week...

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1727 Hyde Park St, Sarasota $1,299,000

  • 4 Beds
  • 5.0 Baths
  • 3,134 SqFt
  • 0.20 Acres

West Of Trail Southside Village - Perfection At Its Best. A Casually Sophisticated Residence With Luxurious High-end Finishes In One Of Sarasota's Most Desirable Neighborhoods. Impeccable 4-bedroom, 4.5 Bath Home To Enjoy The Extensive Updates The Curren...

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4153 Camino Real, Sarasota $1,200,000

  • 4 Beds
  • 5.0 Baths
  • 4,775 SqFt
  • 0.29 Acres

Surrounded By Lush, Tropical Foliage, This West Of Trail, Four-bedroom Home Expresses A Sense Of Serene Comfort And Style. An Open And Inviting Main Floor Makes It Enjoyable To Host Social Occasions With Panache From The Dining Room Or Relax In The Cozy Gre...

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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 July 24th, 2017 at 12:03am EDT.