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 56 single-family homes for sale priced from $425,000 to $25,000,000. 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: 56
Average Price: $3,245,812
Highest Price: $25,000,000
Lowest Price: $425,000
Average Size: 3,405 ft²
Average Price Per Square Foot: $828 per ft²

Explore Other West of the Trail Communities

56 Homes for Sale West of the Trail

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Image 0: A4537433

2043 North Alameda Avenue, SARASOTA, FL - $25,000,000

Residential, Single Family Residence
  • 6 Beds
  • 9 Baths
  • 9,600 SQFT
  • 125 DOM
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Pre-construction. To Be Built. The Modern, Luxurious Bayfront Estate, Designed By World-renowned, Miami-based Architectural Firm Cheoff Levy Fischman, Will Be Located At 2043 Alameda Ave. N. In Sarasota, Florida. Cheoff Levy Fischman Is Renowned F...

Image 1: A4546357

1378 Harbor Drive, SARASOTA, FL - $14,000,000

Residential, Single Family Residence
  • 4 Beds
  • 8 Baths
  • 6,238 SQFT
  • 21 DOM
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Poised On Sarasota Bay Appreciating Enchanting Azure Views, The Epitome Of A Lavish Boating Lifestyle In Unrivaled Grandeur Is Defined Throughout This Gated Palatial Estate. Boasting Desirable Exclusivity In The Harbor Acres Community With Prestig...

Image 2: A4515981

1465 Hillview Drive, SARASOTA, FL - $9,575,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,654 SQFT
  • 234 DOM
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One Or More Photo(s) Has Been Virtually Staged. Under Construction. Crafted By The Award-winning Custom Home Builder, Dynan Construction, This Captivating West Indies-inspired Waterfront Residence Is Located In One Of The Most Sought-after Locatio...

Image 3: A4535001

309 Ringling Point Drive, SARASOTA, FL - $8,950,000

Residential, Single Family Residence
  • 5 Beds
  • 5 Baths
  • 7,009 SQFT
  • 132 DOM
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The Views Don’t Get Any Bigger Or Better! Commanding A Superior 270-degree Bayfront View, This Pristine Estate Bestows An Elegant And Sophisticated Waterfront Lifestyle For A Boating And Outdoor Aficionado. The Quality Is Obvious Throughout The 7,...

Image 4: A4525595

1507 Bay Point Drive, SARASOTA, FL - $8,499,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 7,350 SQFT
  • 150 DOM
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Tucked Between Harbor Acres & Downtown Sarasota, This Exquisite, Gated 1-acre Property On A Double Lot Features Deep Sailboat Water On 185 Ft. Of Bay Frontage. A Classical Revival Style With Coastal Southern Charm Begins With The Custom Made Mahog...

Image 5: A4520464

3300 Old Oak Drive, SARASOTA, FL - $8,495,000

Residential, Single Family Residence
  • 4 Beds
  • 7 Baths
  • 6,428 SQFT
  • 292 DOM
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Under Construction. Construction Has Begun... Mark Sultana Designed Waterfront Home On 1.5 Acres. Over 6400 Square Feet With 100 Ft On Sarasota Bay. 4/5 Bedrooms, 5 Bathrooms, 2 Half Baths, Gourmet Kitchen, 4 Car Garage, Elevator, Salt Water Pool ...

Image 6: A4541611

387 South Shore Drive, SARASOTA, FL - $7,500,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 5,540 SQFT
  • 68 DOM
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Sustained No Hurricane Damage This Sarasota Bayfront New Construction 2022 Home Was Built To Most Current Hurricane Code With Concrete Precast Floor System Throughout, Hurricane Doors And Windows And Bifold Interlocking Door System! This Sophistic...

1727 Bahia Vista Street, SARASOTA, FL - $4,750,000

Residential, Single Family Residence
  • 5 Beds
  • 5 Baths
  • 4,829 SQFT
  • 38 DOM
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Highly Coveted “west Of Trail” Custom Home With Two Story Guest-house, Designed By A Phipps Design Llc And Built By Colton Construction, Is Now Available And Ready For Immediate Occupancy! Opportunity Knocks With This Tastefully Updated Home With ...

Image 8: A4541554

1393 Harbor Drive, SARASOTA, FL - $4,699,999

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,316 SQFT
  • 78 DOM
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One Or More Photo(s) Has Been Virtually Staged. Recently Completed True Custom-built Home In Harbor Acres With Incredible Finishes. Built On Over A Third Of An Acre Of Land In A Lush, Tropical Setting And Possibly The Best Neighborhood In Sarasota...

Image 9: A4540234

337 North Shore Drive, SARASOTA, FL - $4,200,000

Residential, Single Family Residence
  • 6 Beds
  • 3 Baths
  • 4,839 SQFT
  • 92 DOM
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Sarasota School Of Architecture. This 6 Bedroom, 3 Bath Home Sits Directly On The Sarasota Bay, And Intracoastal Waterway Offering Crystal Clear Views To The World-famous Ca D’zan. This Multi-level Home Sits On A Huge Double Lot Allowing For Deve...

1960 Boyce Street, SARASOTA, FL - $3,900,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,674 SQFT
  • 299 DOM
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Pre-construction. To Be Built. Construction Is Progressing On This Spectacular Home Featuring 4 Bedrooms, 4 1/2 Bathrooms, And A 3 Car Garage In The Highly Sought After Prime "west Of The Trail" Neighborhood. Ks Contracting Services And Del Vescov...

Image 11: A4545760

1620 North Lodge Drive, SARASOTA, FL - $3,784,000

Residential, Single Family Residence
  • 5 Beds
  • 4 Baths
  • 4,660 SQFT
  • 40 DOM
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Waterfront Vacant Lot. Pre-construction. Build Your Dream Custom Home With Skyline Custom Development, An Unmatched Luxury Waterfront Home Contractor/specialist. Quietly Nestled In One Of Sarasota’s Most Treasured Neighborhoods, Cherokee Park, Thi...

Image 12: A4536016

1718 Bay View Drive, SARASOTA, FL - $3,650,000

Residential, Single Family Residence
  • 6 Beds
  • 6 Baths
  • 4,644 SQFT
  • 100 DOM
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Perfectly Located In The Picturesque West Of The Trail Enclave Of Bay View Heights – Between Cherokee Park And Harbor Acres – This Thoughtfully Renovated Traditional Masterpiece Blends Classic Original Details And Charm With Modern Conveniences An...

Image 13: A4541870

1718 Prospect Street, SARASOTA, FL - $3,650,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,282 SQFT
  • 83 DOM
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An Enchanting Estate, Perfectly Positioned Within Sarasota’s Coveted West Of Trail Neighborhood. Effortless, Elevated, And Generous In Size, The Wonderfully Scaled Interiors Are Better Than New And Have Been Designed With Accountability For Every ...

1524 Pine Bay Drive, SARASOTA, FL - $3,500,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,186 SQFT
  • 82 DOM
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Located In The Stunning Oyster Bay Area, This Spectacular New Construction Majestik Homes Brings Together Modern Finishes With A Traditional Style. At Nearly 4,200 Sq.ft. And Boasting 5 Bedrooms, 4.5 Bathrooms, 1524 Pine Bay Drive Is Defined By L...

1919 Irving Street, SARASOTA, FL - $3,499,000

Residential, Single Family Residence
  • 6 Beds
  • 6 Baths
  • 4,956 SQFT
  • 29 DOM
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This Classic Remodeled Home Is Nestled In One Of The Most Desirable Areas In Sarasota. Imagine Being In Close Proximity To Southside Village, Morton’s Market, Top-ranked Southside School, Downtown Sarasota’s Arts And Cultural District, And World-r...

Image 16: A4544803

3127 Bay Shore Road, SARASOTA, FL - $3,485,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,219 SQFT
  • 50 DOM
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This Enviable Address, With Private Frontage On Sarasota Bay, Showcases Spectacular Water And Sunset Views. The Hurricane Shutter Protected Home Resides On A Beautifully Landscaped Lot. Concrete Garden Walls Surround The Property And A Stately Cus...

1615 North Lake Shore Drive, SARASOTA, FL - $3,295,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 3,383 SQFT
  • 306 DOM
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Under Construction. Luxurious Amenities Define This Fabulous New Residence In Oyster Bay Estates That’s Been Masterfully Planned And Executed With Attention To Detail That’s Second To None. The Enticing “kristi Ann Modern” Plan Is An Artful Creati...

1642 Bahia Vista Street, SARASOTA, FL - $2,998,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 2,938 SQFT
  • 26 DOM
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Pre-construction. To Be Built. Take Advantage Of This Ready-to-build Opportunity In One Of The Most Sought-after Locations In Sarasota. Located On A Quiet Street “west Of Trail” And Very Close To Downtown, This Lot And Home Package Are Being Sold...

1929 Morris Street, SARASOTA, FL - $2,950,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 3,035 SQFT
  • 272 DOM
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Pre-construction. To Be Built. From The Creative Minds Of The Award-winning Allegra Homes Team Of Professionals Is This Incredible 3,035-square-foot “kristi Ann Modern” Floor Plan To Be Built In One Of Sarasota’s Most Prized School Districts And L...

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 October 5th, 2022 at 1:03am 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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