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West of the Trail Sarasota

West of the Trail homesAsk any local Sarasota resident to identify the most valuable and desirable properties in town and you'll probably hear them say, “anything West of the Trail.” Sarasota real estate buyers considering this area are typically looking for one or more of the premium features that define West of Trail neighborhoods: that is, waterfront property and boating access, historic and/or restored homes, charming neighborhood character, low commute times, pedestrian and cycling-friendly traffic, and neighbors that put a high value on community, as well as thoughtful planning by its real estate developers. Browse the current listings below or learn more about West of the Trail Homes.

West of the Trail Homes for Sale

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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7922 S Holiday Dr, Sarasota, FL - $6,975,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 8,505 SQFT
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Auction: December 13th. Selling Without Reserve. Open Daily 1–4pm By Appointment. Sunset Preview Event November 15th From 4–7pm. Enjoy Indoor/outdoor Luxury At This Five Bedroom Bayfront Estate Featuring Modern Home Technology, A Large Chef's Kitc...

1333 Vista Dr, Sarasota, FL - $6,249,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,738 SQFT
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Under Construction. Inspired By The Understated Luxury Of A Caribbean Villa, This Brand New, Two-story Home This Custom Residence Offers Serene Water Views From Its Prime Location On 100 Ft Of Sarasota Bay. The Approximately 5,800 Sq. Ft. Of Inter...

Photo of Listing #A4203772

1337 Vista Dr, Sarasota, FL - $6,200,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 6,425 SQFT
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Pre Construction. To Be Built A Collaboration Of Sarasota's Finest Clifford M Scholtz, Architects, Murray Homes, Builder And Michael A. Gilkey, Landscape Architect Have Combined Their Talents To Create A M...

1540 Hillview Dr, Sarasota, FL - $5,595,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 7,074 SQFT
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Set In A Commanding Waterfront Location On Hillview Drive, One Of The Most Prized Addresses In Sarasota, This Simply Sublime Home Is Bestowed With Scenic Southern Exposure, Vast Yet Comfortable Living Spaces And Exceptional Quality. Panoramic Pers...

3544 San Remo Ter, Sarasota, FL - $4,890,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 6,710 SQFT
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Stunning Sarasota Waterfront Property. Prime Location In Desirable West-of-trail San Remo Estates, This Custom Built 6,700 Sq. Ft. Home Offers 2 Master Suites With Private Terraces, 3 Guest Suites, 2 Half Baths. Gourmet Kitchen Is Outfitted With V...

1479 Bay Point Dr, Sarasota, FL - $4,375,000

Residential, Single Family Home
  • 4 Beds
  • 3 Baths
  • 3,783 SQFT
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Rare Opportunity To Purchase Land In One Of The Most Exclusive, Waterfront, West Of Trail, Neighborhoods. This Bay Point Gem Is On The Market For The First Time Since Built In 1947. Breathtaking Views Of Sarasota Bay, Ringling Bridge And Golden Ga...

Photo of Listing #A4174153

1352 Harbor Dr, Sarasota, FL - $3,995,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 4,373 SQFT
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Located In Sarasota’s Favorite Mainland Bayside Neighborhood Of Harbor Acres, This Gracious Home Enjoys The Best Of Both Worlds…bay, City And Bridge Views Along With Protected Deep Water Harborage With Approximately 6-7’ Of Water Depth. Constructe...

1329 Vista Dr, Sarasota, FL - $3,795,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,762 SQFT
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Looking For A Peaceful Home On A Large Lot, Overlooking The Boat Basin In Harbor Acres? One That Is Perfect For Entertaining With A Large Refreshing Pool, Abundant Windows For Viewing The Beauty Of The Bay, Four Comfortable And Private Bedroom Sui...

Photo of Listing #A4187925

1344 Harbor Dr, Sarasota, FL - $3,793,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 6,101 SQFT
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A Gorgeous Waterfront Estate Located In The Desirable Bayfront Community Of Harbor Acres—sarasota’s Most Coveted Location.originally Constructed In 1949, This Captivating Residence Underwent A Meticulous And Expansive Renovation In 2004. Its Class...

7697 Cove Ter, Sarasota, FL - $3,399,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 4,797 SQFT
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Possibly One Of The Finest Views Of Sarasota Bay, This Spectacular Gated Boating Estate Offers Stunning Views Of The Intracoastal Waterway From Nearly All Rooms. Located On A Quiet Cul-de-sac In A Convenient Mainland Community; Rear Southern Expos...

Photo of Listing #A4189312

1449 Hillview Dr, Sarasota, FL - $3,350,000

Residential, Single Family Home
  • 5 Beds
  • 5 Baths
  • 4,982 SQFT
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Exceptional And Incomparable Harbor Acres One Level Residence Was Completely Updated In 2015 For Unsurpassed Luxury. Privately Situated Back From The Street On This Estate Sized Lot, This Four-bedroom, Three-and-a-half-bath Main Residence Is In T...

1346 Harbor Dr, Sarasota, FL - $3,290,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,975 SQFT
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Deep Sailboat Water And The Location In The Prestigious Harbor Acres Neighborhood Highlight Two Of The Many Desirable Attributes Of This Four Bedroom, Three-and-one-half Bath Residence Set On More Than A Quarter Acre Near Southside Village And C...

West of the Trail Homes

West of the Trail Sarasota real estateWest of the Trail homes offer special things for the homebuyer. A West of the Trail address means in-town living mingled with some of Sarasota's best shops and boutiques, markets, cafes, restaurants, schools and exceptional health care. 

The real estate market in West of the Trail is comprised of diverse and distinctive residences that may include small cottages and villas, Sarasota School of Architecture homes and condominiums, luxury estates, historic buildings and waterfront properties. If you are looking for a neighborhood with personality, taste, and sure-fire staying power on the market, you will find all of this and more in a West of the Trail home.

 Map of West of the Trail in Sarasota, FL

West of the Trail Real Estate News


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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 December 15th, 2017 at 2:35pm EST.