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 156 single-family homes for sale priced from $249,000 to $15,495,000. 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: 156
Average Price: $2,732,684
Highest Price: $15,495,000
Lowest Price: $249,000
Average Size: 2,925 ft²
Average Price Per Square Foot: $808 per ft²

Explore Other West of the Trail Communities

156 Homes for Sale West of the Trail

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Image 0: A4611675

1490 Hillview Drive, SARASOTA, FL - $15,495,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,587 SQFT
  • 266 DOM
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Under Construction. Completion Date Is End Of 2025. New Construction In The Highly Desirable Harbor Acres Estate Section. Situated On A ½ Acre With 100 Ft Of Waterfront And Southern Facing Open Bay Views. Beautifully Designed By Acclaimed Mhk Arch...

Image 1: A4615836

1610 North Lodge Drive, SARASOTA, FL - $14,700,000

Residential, Single Family Residence
  • 5 Beds
  • 8 Baths
  • 7,110 SQFT
  • 217 DOM
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This Stunning Three Story, Coastal Modern, Single-family Waterfront Home Is The Perfect Blend Of Comfort And Luxury Located In The Treasured Cherokee Park Neighborhood. Nestled On A Street Adorned With Majestic Oak And Canopy Trees, This Exception...

Image 2: A4608565

3336 Old Oak Drive, SARASOTA, FL - $12,900,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 5,932 SQFT
  • 295 DOM
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Nestled Within The Vibrant City Of Sarasota, Florida, This Exquisite Estate Offers An Unparalleled Blend Of Luxury, Privacy, And Natural Beauty. Situated On A Sprawling 2-acre Parcel Of Prime Bayfront Land, This Custom-built Residence Boasts Panor...

Image 3: A4629795

1336 & 1338 Harbor Drive, SARASOTA, FL - $11,995,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 4,366 SQFT
  • 86 DOM
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This Compound (1336 And 1338 Harbor Drive) Waterfront Estate In The West-of-the-trail Harbor Acres Community Offers A Perfect Blend Of Luxury, Privacy, And Serenity. The Chicago Brick Circular Drive Welcomes You To A Walled Property Framed By Lush...

Image 4: A4640544

1808 Flower Drive, SARASOTA, FL - $10,500,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 5,609 SQFT
  • 0 DOM
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A Masterclass In Refined Waterfront Living, This Newly Reimagined Fully Furnished Estate At 1808 Flower Drive In Harbor Acres Embodies The Pinnacle Of Modern Elegance. Envisioned As A Private Resort, This 5,609-square-foot Residence Underwent A Me...

Image 5: A4632433

3350 Old Oak Drive, SARASOTA, FL - $9,800,000

Residential, Single Family Residence
  • 7 Beds
  • 8 Baths
  • 7,181 SQFT
  • 60 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 6: A4632736

1430 Harbor Drive, SARASOTA, FL - $9,600,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 7,049 SQFT
  • 46 DOM
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Harbor House, Located At 1430 Harbor Drive, Stands As The Crown Jewel Of Harbor Acres, Sarasota’s Most Coveted Mainland Neighborhood Known For Record-breaking Sales Year After Year. This Extraordinary Waterfront Estate, Spanning Over 12,000 Total ...

Image 7: A4634377

1541 Bay Point Drive, SARASOTA, FL - $8,309,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 6,368 SQFT
  • 27 DOM
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Nestled On The Prestigious Street Of Bay Point Dr, This Georgian Colonial Home Is A Masterpiece Of Timeless Architecture And Modern Luxury. With Over 6,300 Square Feet Of High And Dry Living Space—untouched By The Recent Hurricanes—every Detail Of...

Image 8: A4627940

4511 Bay Shore Road, SARASOTA, FL - $7,650,000

Residential, Single Family Residence
  • 6 Beds
  • 8 Baths
  • 6,500 SQFT
  • 101 DOM
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Nestled On 1.1 Acres Of Pristine Bayfront Along Sarasota Bay, Etowah Stands As A Timeless Icon Of Sarasota's Rich Heritage. Originally Built In 1925, This Two-story Mediterranean Revival Estate Spans Over 6,500 Square Feet, Offering Captivating Vi...

1521 South Lake Shore Drive, SARASOTA, FL - $6,998,000

Residential, Single Family Residence
  • 4 Beds
  • 7 Baths
  • 4,866 SQFT
  • 12 DOM
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Pre-construction. To Be Built. The Windemere Ii Is An Extraordinary Luxury Custom Home Meticulously Crafted By Heritage Builders. This Coastal Contemporary Residence With Clean Lines Is Situated On A Very Rare West-of-trail Lakefront Estate Home S...

Image 10: A4629452

309 Ringling Point Drive, SARASOTA, FL - $6,850,000

Residential, Single Family Residence
  • 5 Beds
  • 5 Baths
  • 6,918 SQFT
  • 90 DOM
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All Offers Considered.  priced $1,000,000 Below Recent Appraisal. This Elevated Fema Conforming Home Was Not Impacted By Recent Storm Activity. It Was Designed And Built In Excess Of Code. If You Want To Live On The Beautiful Shores Of Sarasota Ba...

Image 11: A4633705

4311 Bay Shore Road, SARASOTA, FL - $6,600,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 5,033 SQFT
  • 38 DOM
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Nestled On Nearly Three-quarters Of An Acre, This Meticulously Updated 1925 Mediterranean Revival Residence Offers Breathtaking, Panoramic Views Of Sarasota Bay, Encompassing The Downtown Skyline, Ringling Bridge And The Northern Tip Of Longboat K...

3350 Old Oak Drive, SARASOTA, FL - $6,500,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,263 SQFT
  • 60 DOM
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Rarely Does An Opportunity Like This Come To Market—a Chance To Own A Piece Of Old Florida On Over An Acre Of Lush, Private Grounds. Nestled In Total Seclusion, This Extraordinary Compound Offers Panoramic Views Of Sarasota Bay, Siesta Key, Bird K...

1429 North Lake Shore Drive, SARASOTA, FL - $5,995,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 4,545 SQFT
  • 16 DOM
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One Or More Photo(s) Has Been Virtually Staged. Under Construction. Welcome To A Life Of Unparalleled Luxury In An Unrivaled Location, Where Every Detail Has Been Meticulously Crafted To Create A Haven Of Sophistication And Comfort. Set Within Oys...

1804 North Lake Shore Drive, SARASOTA, FL - $5,800,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 6,854 SQFT
  • 14 DOM
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Designed By Esteemed Architect John Potvin, This Exceptional Home Combines Elegance With Casual Tropical Charm. Created With Flexibility In Mind, Its Three Distinct Structures—connected By Covered Lanais—provide Privacy And Grand Spaces For Social...

1686 North Drive, SARASOTA, FL - $5,750,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,128 SQFT
  • 11 DOM
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Welcome To This Stunning 2021-built Home In One Of Sarasota’s Most Iconic And Picturesque Historic Neighborhoods, Cherokee Park. Offering Luxurious Living With Thoughtful Design, This Spacious Residence Of Over 6000 Square Feet Features A Desirabl...

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

Residential, Single Family Residence
  • 6 Beds
  • 7 Baths
  • 4,769 SQFT
  • 322 DOM
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*one Or More Pictures Have Been Virtually Staged.* This Stunning Modern Home Is Located In A Lush, Mature-treed, Tropical Setting And Possibly The Best Neighborhood In Sarasota, Harbor Acres. Completely Walled For Privacy And Fronting On A Quiet S...

1827 Morris Street, SARASOTA, FL - $5,125,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,970 SQFT
  • 43 DOM
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The “st. Michael” Is Award-winning Allegra Homes’ 2025 Fully Furnished Model Home Supremely Located Just South Of Downtown Sarasota’s Cultural Epicenter In The Coveted West Of Trail Area Where Residents Know First-hand What A Wonderful Community T...

Image 18: A4638291

1519 Harbor Drive, SARASOTA, FL - $5,100,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,970 SQFT
  • 7 DOM
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Pre-construction. To Be Built. Harbor Acres, Sarasota's Ultimate Neighborhood In Downtown Living. The Highly-acclaimed Team Of Professionals At Allegra Homes Has Yet Again Created A Vision Of Luxury, Elegance And Simplistic Functionality. A Dynami...

Image 19: A4630678

320 South Shore Drive, SARASOTA, FL - $4,990,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 2,978 SQFT
  • 77 DOM
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Exquisite Sarasota Bayfront Estate And Iconic Modern Design With Unmatched Views. At The Apex Of Stephens Point, This Exceptional Property Offers One Of The Most Desired Locations In Sarasota, With Panoramic, 180-degree Views Of North Sarasota Bay...

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 February 14th, 2025 at 10:04pm EST.

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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