West of Trail Homes For Sale - Sarasota

West of Trail Homes

Browse today's new West of Trail homes for sale and real estate in Sarasota below! Cherokee Park and Harbor Acres are lovely, peaceful neighborhoods located in the West of the Trail real estate market which is located slightly south of the downtown area. Residents living here can enjoy easy access to St. Armand’s Circle with its world-class shopping and dining as well as premier golfing at Palmer Ranch. Siesta Key beach also situated within just a short distance of this community.

For buyers who are interested in living on the water, they should look no further than San Remo Estates. This cozy community features lush, mature landscaping and convenient access to amenities throughout the Sarasota area. The Indian Beach neighborhood is located within the highly desirable and popular Museum District located in North Sarasota. Buyers will find a wide range of different home styles here. Whether its a quaint cottage or a multi-million dollar showplace, homebuyers are sure to find something that suits their style of living and budget in the homes for sale around Indian Beach. To learn more about properties available in West of Trail neighborhood near Sarasota or to setup a private home showing, contact your local West of Trail real estate experts today. Read more about West of Trail homes.

Real Estate For Sale West of Trail Sarasota

All Listings $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

Market Statistics

Total Listings: 214
Average Price: $1,295,187
Highest Price: $7,500,000
Lowest Price: $215,900

Real Estate For Sale West of Trail Sarasota

214 Properties Found. Page 1 of 5.
Photo of Listing #A4456765

Imagine your new home nestled amongst a tropical paradise. Surrounded by live oaks and lush vegetation, enjoy peace and tranquility as you step inside this Landings Treehouse. The first level offer...

Photo of Listing #T3205295

Short Sale. .

Photo of Listing #A4451753

You will love the stunning coastal contemporary updates (completed in 2015) offered from every room of this Harbor Acres waterfront home.

Photo of Listing #A4455314

Inspired Coastal Design. Located in the private gated enclave of Oyster Bay Landings, this amazing waterfront residence combines unique architecture and incredible interior design to create a stunn...

Photo of Listing #A4456398

Under Construction. One of a kind Coastal Farmhouse from one of Tampa Bay's premier boutique builders,"Gray Family Homes". This home is unlike anything else in the area and it will be completed by ...

Photo of Listing #A4456425

Harbor Acres is a special neighborhood all about location! Just minutes from lively downtown’s city lifestyle, Sarasota Farmers Market, St. Armands Circle and the Gulf beaches of Siesta, Lido, Long...

Photo of Listing #A4456276

Extremely desirable , West of the trail, over a 1/4 of a acre, Corner lot!

Photo of Listing #A4455842

Do not miss the opportunity to own this fabulous home in the highly sought after community of The Landings. Imagine the peace and tranquility you will experience as you enter your new home through ...

Photo of Listing #A4454400

Great private custom boutique luxury Oyster Bay Estates residence on over half-an-acer! Plus, one of the best west-of-trail homes under a million dollars currently on the market! 10-12FT ceilings, ...

Photo of Listing #A4455905

The perfect blend of refined contemporary styling with the best in mid-century modern are featured in this one-story home. It is perfectly positioned at the "neck" of the large basin allowing for b...

Photo of Listing #A4456206

This condo is priced to sell! Amazing view! A rarely available & coveted 2 bedroom, 2 1/2 bathroom with views of the fountain and lake from the kitchen, dining room, living room, master bedroom and...

Photo of Listing #A4456125

Beautifully renovated West of the Trail home in the very desirable gated community of The Landings in Central Sarasota. A spacious and open floorplan with 3 bedrooms 3 1/2 bathrooms plus a large st...

Photo of Listing #A4455724

Allegra Homes former award winning model, located West of Trail in Southside Village (the hottest location in Sarasota). Just a few blocks from Hillview and Southside Elementary. This home won nume...

Photo of Listing #A4456117

Distinctive salt-water heated pool residence. This home sets in the sophisticated 'West of the Trail' address of quiet Eastbrook Dr. near the Oyster Bay and Field Club area. The house is nestled on...

Photo of Listing #A4456186

Tucked away in charming neighborhood and yet so close to all amenities. Quality Custom built and very private Home in amazing West of the Trail location. Close to great schools, Siesta Key and Down...

Photo of Listing #A4455549

Beautiful sunrise and sunset views of Phillippi Creek from this 3-bedroom 2-bathroom corner unit on the 5th floor. Open floor plan with an abundance of natural light throughout the entire condo. ...

Photo of Listing #A4455995

Rarely Available in Central Park. The waterfront community is located just steps from Downtown Sarasota, Selby Gardens, Bayfront Park and St Armand's Circle. This top floor unit highlights beautifu...

Photo of Listing #A4454318

Enjoy gorgeous sunsets overlooking serene mangroves abutting the Intracoastal Waterway from this updated 2nd floor condo in Eagles Point at The Landings. Just 3 miles to Siesta Key! Watch daily bir...

Photo of Listing #A4455586


Photo of Listing #A4455411

Incredible value in prime West of Trail Granada Park. Beautifully situated on a 175 ft wide lot that is 106 feet deep, this 1939 charmer is pecky cypress on the exterior with vaulted pecky cypress ...

Photo of Listing #A4455544

Spectacular Compound located in the heart of Sarasota, West of the Trail, walking distance to Southside Elem. School & Hillview. This home is spread out across a triple lot, entirely walled, gated ...

Photo of Listing #A4455615

Step into the peace and tranquility of this Landings Treehouse gem where The Landing’s signature landscaping is brought into the home at every turn. Enjoy the End Unit privacy where the open plan o...

Photo of Listing #A4455419

Living in The Landings is living in the midst of everything that Sarasota has to offer. An established, gated, deed restricted community WEST of the trail in a premier school district. This recen...

Photo of Listing #A4455176

Luxuriate in modern green living in a central location, offering the convenience of newer construction. Built to the highest standards by GreenLife Luxury Homes and completed in 2017, this three-be...

Photo of Listing #A4455192

With more than a passing resemblance to Modernist design, this newer build home is a true masterpiece. Clean lines, functionality, accents of natural & industrial elements, technology, an open conc...

Photo of Listing #A4454346

Fall head-over-heels for this West of Trail historic home expertly transformed into a modern family oasis. This new “old” house retains its original character, while introducing up-to-date function...

Photo of Listing #A4453885

City living in a park-like setting. Own a piece of Sarasota’s past in this historic home set in a premiere location off Hudson Bayou and with close proximity to Selby Gardens, Sarasota Bay, and dow...

Photo of Listing #A4454217

Fresh and welcoming, this custom designed home located in the prestigious Oyster Bay Estates area is a textbook example of versatile Florida living. You’ll find the floor plan perfect for empty nes...

Photo of Listing #A4454568

1915 Tulip Drive is the West of the Trail Gem you've been waiting for. Tucked away on a quiet corner, but still just minutes from World Famous Siesta Beach, exciting Downtown Sarasota, Westfield Si...

Photo of Listing #A4452419

This Treehouse is set back from the main road and surrounded by live oaks and lush tropical vegetation. The living room is an open plan with vaulted ceilings and a wood burning fireplace. The end o...

Photo of Listing #A4454103

Prepare to say ‘wow’ upon entering this unique & one of a kind custom residence located in the heart of Sarasota’s West of Trail. Situated on an oversized corner lot, this home is a rare testament ...

Photo of Listing #A4452664

Under Construction. Under Construction. This coastal residence captivates with its impeccably designed décor and outdoor living spaces in a scenic waterfront setting only seconds to the open waters...

Photo of Listing #A4452478

Classic Bungalow, Old Florida Charm-Character Galore-Circus Heritage-4+++ car garage with room for a boat too! West of Trail-Prime mainland location. Original part of home was built in the 1920's....

Photo of Listing #A4452832

San Remo Estates- Here’s a rare opportunity to own this executive style waterfront home in San Remo Estates with just over ½ acre of mature and tropical landscping. Home has almost 4000 sq feet o...

Photo of Listing #A4453062

Have you ever dreamed of water view sunsets, luxurious finishes, boating access and outstanding amenities without having to drive over bridges and fight traffic? Phillippi Landings unit 606 is the ...

Photo of Listing #A4452968

Fantastic opportunity within the popular Treehouses of the Landings. This unit sits tucked into the trees at the end of a short dead-end street with only 3 other Treehouses. This 2-story, spacious ...

Photo of Listing #A4453285

Feel the comfort and charm as you enter this impeccably maintained 3 bedroom, 3 bath Landings home. Easy living and entertaining inside or out, sliding glass doors pocket from all main living areas...

Photo of Listing #A4452760

Looking for an end unit three bedroom upstairs coach house ? Take a look at this great opportunity that has wood floors and a tranquil wooded view. Volume ceilings, large living/dining room and spa...

Photo of Listing #A4452994

One of a kind West of Trail home that is minutes to Southside Elementary School, Westfield Siesta Key Mall, Downtown Sarasota and Siesta Key Beach. This Modern home was built in 2014 by Ampersand ...

Photo of Listing #A4452325

Ideally situated in the sought after WEST OF TRAIL Poinsettia Park neighborhood, this elegant D.R. Horton home shows like brand new construction! Once through the handsome leaded glass front door, ...

Photo of Listing #A4445676

Seller has priced aggressively at LAND VALUE for immediate sale. Located in Oyster Bay, one of Sarasota’s most revered neighborhoods and close to the Field Club. Located on a quiet cul-de-sac stre...

Photo of Listing #A4452303

Arguably, one of the most classic and unique homes to come on the market in Sarasota County in years. Located on a double lot (almost 3/4 of an acre) at the end of a dead-end street in the historic...

Photo of Listing #A4452304

This breathtaking 5 bedroom, 3.5 bath home is finally for sale. This home features two oversized master suites, one on each floor. The downstairs master includes an en-suite office/media area. The...

Photo of Listing #A4451240

Charming and Classic American Cottage located West of the Trail with canopied tree lined streets and a lovely walkable neighborhood. From the moment you approach the warm and inviting front porch y...

Photo of Listing #A4451918

Come home to the Landings, a social gated community with an active lifestyle. A lovely three bedroom, two bath condominium with almost 2,000 square feet of living area, nestled in park like sett...

Photo of Listing #A4449947

Looking to downsize or perhaps to spend the winter in Florida? This Landings single family home is the answer. A well-maintained property with a split floor plan. The paver driveway and walkway ...

Photo of Listing #A4451948

Nestled West of the Trail in one of the most sought-after neighborhoods in Sarasota is a symphony of glass, steel, and concrete woven together with light, water and natural elements. This poetic 3-...

Photo of Listing #A4451784

This mid-century home in Oyster Bay Estates defines Florida living as it used to be. Lushly landscaped with oak trees, bamboo and exotic plants, you’ll be living in a tropical wonderland. As you ar...

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Want to purchase a home in West of Trail? Call your West of Trail real estate team, DWELL Real Estate, at (941) 822-0708. Your neighborhood West of Trail real estate agents are here to help with the West of Trail housing market.



Sarasota Bradenton Anna Maria Island Longboat Key Siesta Key Lido Key St. Armands Circle
Bird Key Casey Key Downtown Sarasota Lakewood Ranch West of Trail Palmer Ranch St. Petersburg



Suburbs Condo Living Luxury Properties Gated Communities Beach Condos Downtown Living
Waterfront Golf & Tennis Barrier Islands Master Planned Communities 55+ Communities Acreage


West of Trail Real Estate Market

Oyster Bay Estates is a neighborhood located in the West of the Trail real estate market and is situated directly on Sarasota Bay. A quick drive down streets such as South Lakeshore Drive, Field Road or Camino Real and buyers will see what makes this exclusive neighborhood so desirable. And for potential buyers who also happen to be boaters, they will certainly appreciate living so close to deep water canals and stunning bay views. Oyster Bay is also conveniently located near Siesta Key Beach as well as the downtown Sarasota restaurants, shopping and numerous cultural amenities. The Field Club is also located in Oyster Bay, offering tennis, boating, dining and pool facilities as well as social events.

Another neighborhood homebuyers should consider is The Landings. Those touring the area will find this neighborhood in central Sarasota complete with a retail shopping center, marina, racquet club and nature preserve. With meandering streets through lush natural tropical landscaping, this neighborhood is one of the most desirable in Sarasota. There are numerous choices for prospective homebuyers here, including waterfront condo properties, maintenance-free villas, and exclusive single family homes. 

No matter what type of neighborhood and amenities a buyer may be seeking, the right community for any lifestyle and budget can be found in the many fabulous communities located West of the Trail in Sarasota, Florida.

West of Trail Videos


Five Things You Should Know about West of the Trail Neighborhoods

 West of Trail is one of the most sought after housing markets in Sarasota, with most real estate selling very quickly. 

 Diverse selection of homes with an abundance of character for every lifestyle and budget.

 Residents enjoy the convenient location near Siesta Key beach, downtown Sarasota, St. Armands Circle and Lido Key. 

 Great for families, snowbirds, young professionals and empty nesters alike.

  A lot of older homes for sale are available in this area, allowing buyers the flexability of custom upgrades.  


West of Trail Community Highlights

  • As one of the older communities, this area features protected, historical neighborhoods such as Cherokee Park, Harbor Acres, McClellan Park, The Landings and more
  • Residents enjoy the walkability of the neighborhoods as well as interlinking parks
  • Popular nearby attractions include The Ringling Museum, Marie Selby Botanical Gardens, the Ca d’Zan Mansion, Mote Marine Laboratory and Aquarium and more
  • Major medical facilities to serve the area are Sarasota Memorial Hospital, Sarasota Urgent Care West, Doctors Hospital and more
  • Higher education institutions nearby include East West College-Natural Med, New College of Florida, Ringling College of Art and Design and others

West of Trail Real Estate Agents

If you're buying or selling a home in West of Trail, let our team of West of Trail real estate agents guide you through buying or selling your West of Trail property today. As local West of Trail real estate agents and experts, we have exclusive insider knowledge of West of Trail market dynamics. Let us help you today!

To learn more about agent representation while buying or selling your West of Trail home, contact DWELL Real Estate. Check out our comparative market analysis page to receive a free home value analysis in West of Trail. We'll get to work for you today!

Community Reviews

5 Based on 2 Ratings

Recent Ratings & Reviews

, Resident

Simply, the best area of Sarasota. Convenient, not stuck out on the barrier islands. Great families. Great diversity in houses. Great schools.


Expensive for what you get.


Love it here. No plans of leaving. I try to get all of my friends to move here.

, Resident

Super convenient to everything in Sarasota. A great diversity in homes - from tear downs to waterfront mansions. School district


Highly sought after = Expensive


West of the Trail is a wonderful place to live.

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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 DBA Stellar MLS.

Listing information last updated on January 19th, 2020 at 12:00am EST.