West of the Trail Sarasota Real Estate

  • Description
  • Listings
  • Map
  • Contact

Overview

Below are the current West of the Trail Sarasota real estate listings. Our website allows you to easily search through the 189 single-family homes for sale priced from $379,000 to $18,645,000. 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!

… Read More

MLS® Listing Statistics

Total Listings: 189
Average Price: $2,612,696
Highest Price: $18,645,000
Lowest Price: $379,000
Average Size: 2,958 ft²
Average Price Per Square Foot: $769 per ft²

Explore Other West of the Trail Communities

189 Homes for Sale West of the Trail

Map Save this Search
Sort listings by:Price, High to Low
Image 0: A4653958

1423 & 1435 Hillview Drive, SARASOTA, FL - $18,645,000

Residential, Single Family Residence
  • 6 Beds
  • 9 Baths
  • 11.6k SQFT
  • 15 DOM
View details More Photos Save

Welcome To A Home That Lives Like A Resort, Set On Two Lots Consisting Of 1.8 Lush, Waterfront Acres In Sarasota’s Premier Neighborhood, Harbor Acres. Crafted For Laid-back Luxury And Everyday Ease, This Nearly 12,000-square-foot Estate Offers 249...

Image 1: A4650403

4123 Bay Shore Road, SARASOTA, FL - $15,000,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 5,117 SQFT
  • 37 DOM
View details More Photos Save

An Exquisite Jewel Of Contemporary Architecture With Almost 180ft On Sarasota Bay With Nearly Endless Water Views. This Contemporary Masterpiece Was Designed By Renowned Dsdg Architect Mark Sultana And Built By Voigt Brothers Construction, And It ...

Image 2: A4654131

4035 Bay Shore Road, SARASOTA, FL - $12,000,000

Residential, Single Family Residence
  • 8 Beds
  • 9 Baths
  • 8,875 SQFT
  • 21 DOM
View details More Photos Save

Secure One Of Sarasota’s Rarest Waterfront Residences With This Newly Built, Bayfront Estate Redefining Modern Luxury With Nearly 20,000 Total Square Feet Of Entertaining Space, Overlooking The Glistening Waters Of Sarasota Bay And The Downtown Sa...

Image 3: A4656139

1610 North Lodge Drive, SARASOTA, FL - $11,900,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 7,110 SQFT
  • 1 DOM
View details More Photos Save

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 4: A4645599

1333 Vista Drive, SARASOTA, FL - $11,625,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,844 SQFT
  • 75 DOM
View details More Photos Save

On Pristine Boating Waters In Harbor Acres, 1333 Vista Drive Is A Luxurious And Inviting Retreat Designed For Those Who Appreciate Extraordinary Craftsmanship, Effortless Entertaining And Tranquility Of Coastal Living. From The Moment You Arrive, ...

Image 5: A4652447

1384 Harbor Drive, SARASOTA, FL - $11,475,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,027 SQFT
  • 28 DOM
View details More Photos Save

One Or More Photo(s) Has Been Virtually Staged. Under Construction. Opulent Bayfront Estate In Harbor Acres Where Timeless Elegance Meets Modern Resilience. Experience Unparalleled Luxury With This Reimagined, Reinspired Masterpiece, Nestled In Sa...

Image 6: A4632433

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

Residential, Single Family Residence
  • 7 Beds
  • 8 Baths
  • 7,181 SQFT
  • 183 DOM
View details More Photos Save

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 7: A4647101

1540 Hillview Drive, SARASOTA, FL - $8,850,000

Residential, Single Family Residence
  • 4 Beds
  • 7 Baths
  • 7,074 SQFT
  • 75 DOM
View details More Photos Save

Nestled In The Prestigious Harbor Acres, This Exceptional 4-bedroom Waterfront Estate Embodies The Pinnacle Of Luxury Living. Boasting 100 Feet Of Prime Bay Frontage With A Private Dock, This Masterpiece Offers Breathtaking, Unobstructed Views And...

Image 8: A4634377

1541 Bay Point Drive, SARASOTA, FL - $7,900,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 6,368 SQFT
  • 127 DOM
View details More Photos Save

Nestled On The Prestigious Bay Point Dr, This Georgian Colonial Home Blends Timeless Architecture & Modern Luxury. With Over 6,300 Sq.ft Of High & Dry Living Space—untouched By Recent Hurricanes—every Detail Of This Four-bedroom, All-en-suite Resi...

Image 9: A4627940

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

Residential, Single Family Residence
  • 6 Beds
  • 8 Baths
  • 6,500 SQFT
  • 222 DOM
View details More Photos Save

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
  • 137 DOM
View details More Photos Save

Under Construction. 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 Site. The Ex...

1365 Harbor Drive, SARASOTA, FL - $6,950,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,815 SQFT
  • 49 DOM
View details More Photos Save

Enjoy The Prestige Of Harbor Acres, Sarasota’s Premier Neighborhood, Just Minutes From Downtown And Its Vibrant Bayfront. This Like-new, Contemporary Estate Is More Than A Home—it’s A Statement Of Intent. Designed For Those Who Value Clean Lines, ...

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

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,263 SQFT
  • 183 DOM
View details More Photos Save

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...

2100 Mcclellan Parkway, SARASOTA, FL - $6,000,000

Residential, Single Family Residence
  • 5 Beds
  • 9 Baths
  • 4,450 SQFT
  • 92 DOM
View details More Photos Save

Pre-construction. To Be Built. Pre-construction, To Be Built. Situated West Of The Trail, This Exceptional Estate Represents The Pinnacle Of Luxury Living In Sarasota. Developed By M&j Pham Development, This Residence Is A Masterpiece Of Innovativ...

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

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 4,545 SQFT
  • 392 DOM
View details More Photos Save

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...

Image 15: A4629452

309 Ringling Point Drive, SARASOTA, FL - $5,990,000

Residential, Single Family Residence
  • 5 Beds
  • 5 Baths
  • 6,918 SQFT
  • 215 DOM
View details More Photos Save

Sarasota Bayfront Priced $2,200,000 Below Recent Appraisal!! Elevated Fema Conforming Home 17 Feet In Elevation. Designed And Built In Excess Of Code. 270-degree Views Of Open Water Taking In Lido And Longboat Key. If You Want To Li...

Image 16: A4633705

4311 Bay Shore Road, SARASOTA, FL - $5,945,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 5,033 SQFT
  • 163 DOM
View details More Photos Save

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...

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

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 6,854 SQFT
  • 139 DOM
View details More Photos Save

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...

Image 18: A4647998

1479 Bay Point Drive, SARASOTA, FL - $5,500,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 3,783 SQFT
  • 72 DOM
View details More Photos Save

Being In The Same Family For 75 Years, This Is A Rare Opportunity To Own A Stunning, Nearly Half-acre Waterfront Lot In The Highly Desirable Bay Point Park Neighborhood Of Sarasota. Situated On Protected Sailboat Water With No Bridges To The Gulf ...

Image 19: A4638710

1686 North Drive, SARASOTA, FL - $5,200,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,128 SQFT
  • 136 DOM
View details More Photos Save

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...

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 June 19th, 2025 at 3:06pm 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.

No image

The Landings

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

No image

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.

Map of West of the Trail

Save this Search
Sort listings by:Price, High to Low
Sort listings by: Price

Ask a Question. We are here to help!

Please provide a valid email address.