West of the Trail Sarasota Real Estate

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Overview

Below are the current West of the Trail Sarasota real estate listings. Our website allows you to easily search through the 121 single-family homes for sale priced from $399,900 to $14,950,000. Our database is updated throughout the day from the Multiple Listing Service (MLS). BuySarasota.com is committed to providing you with the most up-to-date and freshest local listings on the Internet.

Allen Real Estate Services, Inc. is a full service, boutique real estate brokerage offering specialized service and expertise to customers selling and buying real estate in Sarasota. To learn more about any of these properties or receive email updates when new listings hit the market, simply give us a call at 941-544-6467 or send us an email. We are here to help!

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MLS® Listing Statistics

Total Listings: 121
Average Price: $2,704,434
Highest Price: $14,950,000
Lowest Price: $399,900
Average Size: 2,938 ft²
Average Price Per Square Foot: $822 per ft²

Explore Other West of the Trail Communities

121 Homes for Sale West of the Trail

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Image 0: A4588632

3000 Southwest Drive, SARASOTA, FL - $14,950,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 8,125 SQFT
  • 156 DOM
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Discover The Perfect Blend Of Elegance And Privacy On This 1.6-acre Estate Nestled Within Cherokee Park, One Of The Most Sought-after Mainland Neighborhoods In Sarasota. Tucked Away On A Small Street At The End Of Southwest Drive, This Double Lot ...

Image 1: A4590940

1378 Harbor Drive, SARASOTA, FL - $12,400,000

Residential, Single Family Residence
  • 4 Beds
  • 8 Baths
  • 6,238 SQFT
  • 131 DOM
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Poised On The Pristine Waters Of Sarasota Bay, This Luxurious Palatial Bayfront Estate Boasts Breathtaking Panoramic Views And A Spectacular Waterfront Lifestyle. Indulge In A Life Of Unrivaled Grandeur In This Gated Architectural Wonder Nestled W...

Image 2: A4595100

3350 Old Oak Drive, SARASOTA, FL - $11,500,000

Residential, Single Family Residence
  • 7 Beds
  • 8 Baths
  • 7,181 SQFT
  • 98 DOM
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Rarely Does An Opportunity Like This Come To Market, Offering A Piece Of Old Florida On 2.1 Lush Acres And Boasting Breathtaking Views Of Sarasota Bay, Siesta Key, Bird Key, Ringling Bridge, And Downtown Sarasota, This Magnificent Family Compound ...

Image 3: A4599458

1500 Bay View Drive, SARASOTA, FL - $11,499,000

Residential, Single Family Residence
  • 5 Beds
  • 5 Baths
  • 4,031 SQFT
  • 61 DOM
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Nestled In The Heart Of Sarasota, Florida, "the Seathrough House" Stands As A Testament To Timeless Elegance And Modern Sophistication. Designed By The Acclaimed Architectural Firm Sweet Sparkman And Meticulously Crafted By Builder Josh Wynne, Thi...

Image 4: A4593532

309 Ringling Point Drive, SARASOTA, FL - $7,900,000

Residential, Single Family Residence
  • 5 Beds
  • 5 Baths
  • 6,918 SQFT
  • 111 DOM
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Location, Location, Location Is What Makes Villa Di Amore So Special. Come And See For Yourself How To Escape The Crowds And Traffic On The Barrier Islands But Still Be On Sarasota Bay Just Minutes To All The Amenities Our Vibrant Community Has To...

4431 Camino Real, SARASOTA, FL - $7,500,000

Residential, Single Family Residence
  • 6 Beds
  • 7 Baths
  • 5,557 SQFT
  • 208 DOM
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Pre-construction. To Be Built. Welcome To The Epitome Of Sarasota Luxury Living At 4431 Camino Real—a Prestigious, Modern Custom-built Residence Where Elegance Meets State-of-the-art Living In The Heart Of Sarasota’s Exclusive Oyster Bay Estates. ...

Image 6: A4592554

1515 Hillview Drive, SARASOTA, FL - $7,250,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 5,424 SQFT
  • 125 DOM
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Price Improvement. Imagine Living In A Gorgeous, Brand New Waterfront Home On One Of Sarasota's Most Desirable Streets...presenting Another Stunning Design By Coastal Luxury Homes. This Magnificent Contemporary Has Water Views From Almost Every R...

Image 7: A4594149

4311 Bay Shore Road, SARASOTA, FL - $6,500,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 5,033 SQFT
  • 99 DOM
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Conveniently Located In Indian Beach And Sapphire Shores, This Updated 1925 Mediterranean Revival, On Nearly .75-acres Offers Sweeping Views Of Sarasota Bay From The Downtown Skyline And Ringling Bridge To The Tip Of Longboat Key. While Retaining ...

Image 8: A4600257

1449 Hillview Drive, SARASOTA, FL - $6,500,000

Residential, Single Family Residence
  • 5 Beds
  • 5 Baths
  • 4,982 SQFT
  • 50 DOM
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Outstanding Opportunity In The Harbor Acres Estate Section, One Of The Most Coveted Neighborhoods In Sarasota. Situated On A Sprawling .69-acre Lot With 105 Feet Of Waterfront On The Bay, This Home Is Set Back From The Street And Surrounded By Mat...

Image 9: A4607277

1804 North Lake Shore Drive, SARASOTA, FL - $6,295,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 6,854 SQFT
  • 2 DOM
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This Unique Home Is Designed To Assemble Your Family And Friends, To Share Good Food, And To Enjoy The Good Life. Esteemed Architect John Potvin Imagined Three Separate Buildings Connected By Covered Lanais To Provide Complete Privacy When Desired...

418 Acacia Drive, SARASOTA, FL - $5,995,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,904 SQFT
  • 121 DOM
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One Or More Photo(s) Has Been Virtually Staged. Pre-construction. To Be Built. Experience The Pinnacle Of Contemporary Luxury In This Meticulously Designed Cantilevered Home By The Globally Renowned Spanish Architect Fran Silvestre. Paired With It...

Image 11: A4561284

1479 Bay Point Drive, SARASOTA, FL - $5,875,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 3,783 SQFT
  • 425 DOM
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Rare Opportunity To Build Your "dream Home" In One Of The Most Exclusive Waterfront Areas West Of Trail Neighborhoods. The Property Offers Breathtaking Views Of Sarasota Bay And Golden Gate Point. Centrally Located Between Lido Key, Siesta Key, An...

1640 Waldemere Street, SARASOTA, FL - $5,775,000

Residential, Single Family Residence
  • 7 Beds
  • 8 Baths
  • 5,500 SQFT
  • 101 DOM
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Pre-construction. To Be Built. Make Appointment To See The Completed Model Home At 2163 Hillview To See All Finishes And Check The Plans For New Home Being Built Here At 1640 Waldemere. Great West Of Trail Lot 3 Homes Away From Harbor Acres... Cou...

Image 13: A4584482

1655 South Drive, SARASOTA, FL - $5,695,000

Residential, Single Family Residence
  • 5 Beds
  • 9 Baths
  • 6,355 SQFT
  • 160 DOM
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One Or More Photo(s) Has Been Virtually Staged. Located In One Of The Most Sought-after West Of Trail Neighborhoods In Sarasota, Cherokee Park, Encounter A Testament To A Bespoke Luxury Lifestyle, With Every Detail Considered For An Exceptional Li...

1607 Flower Drive, SARASOTA, FL - $5,590,000

Residential, Single Family Residence
  • 6 Beds
  • 7 Baths
  • 4,769 SQFT
  • 19 DOM
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This Stunning, Modern Home Is Nearly Completed. Located In A Lush, Mature-treed Lot Of Over A Third Of An Acre, In A Tropical Setting And Also In, Possibly The Best Neighborhood In Sarasota, Harbor Acres. Completely Walled For Privacy And Fronting...

Image 15: A4597533

907 Pomelo Avenue, SARASOTA, FL - $5,500,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,289 SQFT
  • 79 DOM
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West Of The Trail Waterfront… Welcome To This Elegant Classic Home With A Coastal Flair, Located Just Minutes From Downtown Sarasota. A Fabulous Location, A Smart Floor Plan, Views Of Hudson Bayou Create A Winning Combination. Over 4,200 Sf Of Bea...

Image 16: A4586511

1718 Bay Street, SARASOTA, FL - $4,925,000

Residential, Single Family Residence
  • 5 Beds
  • 4 Baths
  • 4,015 SQFT
  • 180 DOM
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One Or More Photo(s) Has Been Virtually Staged. The Downtown Sarasota Waterfront Setting Doesn’t Get Any Better. Located In A Federally Qualified Opportunity Zone, The Investment Opportunity For This Property Offers Significant Tax Benefits. This ...

Bay Shore Road, SARASOTA, FL - $4,500,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,410 SQFT
  • 51 DOM
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Pre-construction. To Be Built. This Modern Home Is Built For The Ease Of Living And Entertaining. Enjoy This Home With Exceptional Outdoor Living Space. The Home Features 4 Bedrooms, 4 Full And 1 Half Baths, Plus An Office, Along With A Huge Cover...

Image 18: A4607053

3528 Chapel Drive, SARASOTA, FL - $4,500,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,706 SQFT
  • 4 DOM
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Under Construction. This Is A Unique Opportunity To Purchase A Custom-designed Home That Allows You To Be Part Of The Creation Process, Offered At $4,500,000 And Scheduled For Completion Near July Of 2024. The Mid-century Modern Home Boasts 4,706 ...

1550 South Orange Avenue, SARASOTA, FL - $4,438,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,189 SQFT
  • 366 DOM
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Available Luxury Custom Home With Leaseback.welcome To The Epitome Of Luxury Living In The Coveted Harbor Acres Community! This Magnificent 2-story Custom Home Boasts Over 4,000 Square Feet Of Living Space, Featuring 4 Bedrooms, 5 And A Half Bathr...

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 April 17th, 2024 at 5:20pm EDT.

West of the Trail Description (continued)

Sarasota's "West of the Trail" neighborhoods are all established communities west of US 41. Many of the homes in these highly desirable areas have been completely remodeled or torn down and rebuilt. This area offers an ideal location for jogging and biking. Many of Sarasota's best amenities are within walking distance including restaurants, shopping, Southside Elementary School and the Sarasota Memorial Hospital.

There are a wide range of architectural styles including Spanish Mediterranean, contemporary, and old-Florida. West of the Trail real estate prices range from the $400,000 to the millions.

West of the Trail Home

Popular Neighborhoods West of US 41

Cherokee Park

Cherokee Park

Established neighborhood with homes from the $500,000s to over $5,000,000.

Coral Cove

Coral Cove

Located south of Stickney Point, Coral Cove is a favorite among many avid boaters.

Harbor Acres

Harbor Acres

This prestigious west of the trail waterfront neighborhood is a favorite of many physicians and downtown Sarasota professionals.

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The Landings

Gated community located just south of proctor and west of 41.

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Oyster Bay Estates

This Mature neighborhood features tropical vegetation and homes into the millions.

Southpointe Shores

Southpointe Shores

This south Sarasota boating community features 112 homes with about half directly on the water.

Do you have any questions or need more information on West of the Trail real estate in Sarasota? Contact me today so we can talk about your real estate needs.

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