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: 216
Average Price: $1,222,302
Highest Price: $7,500,000
Lowest Price: $219,000

Real Estate For Sale West of Trail Sarasota

216 Properties Found. Page 1 of 5.
Photo of Listing #A4448835

Pre-Construction. To be built. **Photos are of a prior model. Allegra Homes, your West of Trail builder. The selections for this home may vary**

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 #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 #A4451199

The charm of an older home with the upgrades and updates of a newer one. Positioned on a large corner lot affording privacy, this property is in a highly desirable west of the trail neighborhood an...

Photo of Listing #A4451404

One or more photo(s) has been virtually staged. Welcome Home to this fabulous 3 bedroom home with a 3 car garage in highly sought after nieghborhood of The Landings. This home has been recently up...

Photo of Listing #A4450683

This wonderful home of unmatched charm and quality was inspired by the unique architecture of Charleston and Sweden. Seldom does one find the combination of a special home, in a great neighborhood....

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 #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 #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 #A4444762

This beautiful, 2015-built, coastal contemporary five-bedroom + office home in exclusive Oyster Bay provides all the benefits of “new construction” without the delays, surprise costs and effort to ...

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 #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 #A4452832

***Multiple Offers Seller Requests Highest & Best offers by 12/13/2019 5:00 PM ( EST) *** San Remo Estates- Here’s a rare opportunity to own this executive style waterfront home in San Remo Est...

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 #A4447472

Great Location for this gorgeous fully remodel furnished condo in upscale waterfront gated community of Phillipi Landings. One of Sarasota's best kept secrets. Come and enjoy a luxurious lifestyle ...

Photo of Listing #A4449520

In Sarasota, THE LANDINGS is a much sought-after place to live. It is gated, beautifully landscaped, quiet and centrally located. Only six minutes from Sarasota Memorial Hospital and ten from the S...

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 #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 #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 #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 #A4451604

Charm and location combined with a beautiful renovation, make this special home an entertainer’s dream. West of Trail, offering 4 bedrooms plus an office, 2 full bathrooms plus powder room. Guest B...

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...

Photo of Listing #A4451331

Welcome to this West of the Trail hidden cottage. If you are looking for true Florida charm with a flair of mid-century style, you just discovered your dream home. This 2 bedroom 1 ½ bath cottage w...

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 #A4451383

Welcome home to this updated Landings beauty, offering exceptional indoor and outdoor space in a park like setting with tropical landscaping. You will also be amazed by centuries old mature oak tre...

Photo of Listing #A4451295

Imagine the "Landings" Lifestyle: Come home along winding roads with large shade trees. Enjoy neighborhood lakes, parks, tennis courts, nature trails, and access to Roberts Bay. At the same time ...

Photo of Listing #A4450267

A timeless renovation, this “Coastal Contemporary” West of Trail home in has been renovated to take full advantage of its picturesque natural setting. Light and bright, entering the home feels like...

Photo of Listing #A4451154

West of Trail in Historic Granada. In 1924, Charles Tyson had a vision for an ideally located section of Sarasota. Just three blocks from the bay, close to Siesta Key Beach and downtown Sarasota, T...

Photo of Listing #A4451167

This fantastic West of Trail lot is located in one of Sarasota's best neighborhoods - imagine building your dream home here! With a high level of walkability - you will find that on foot or by vehi...

Photo of Listing #A4450957

If you are looking for a touch of paradise with a dash of serenity look no further. This exquisite home is located in a highly desirable location, West of the Trail. Upon entering this coastal cont...

Photo of Listing #A4451582

Wonderful location in high demand area west of the trail. Move right in to your sprawling ranch style home or remove current home and build custom on this extremely large lot. Lot can also be spli...

Photo of Listing #A4450557

West of the trail waterfront luxury condo at its finest in the Hudson Bayou. Totally updated and turned key furnished 3 bedrooms, 2 bathrooms, a deeded dock/ lift and a garage, this condo is an inc...

Photo of Listing #A4450831

The charm of the old with the modern look and style of the new! This one-of-a kind, 1925 home on a quiet West of Trail lane, was recently renovated and remodeled from top to bottom with exquisite a...

Photo of Listing #A4450162

Hailed as one of the best lots in Harbor Acres, spectacular direct views of Sarasota Bay, John Ringling Bridge, downtown’s cityscape and sights of sailboats abound around every corner of this five-...

Photo of Listing #A4449969

Where else will you find a beautiful condo with tranquil water views that includes an oversized garage with ample space for your workbench and tools? This Eagles Point residence has it all. Expertl...

Photo of Listing #A4450246

Enjoy a relaxed, easy lifestyle in this 2,495 sq. ft. two story home in one of Sarasota's most beautiful and desired communities located west of the Trail and just moments from the shopping, dining...

Photo of Listing #A4450305

Under Construction. To be built. Expected completion Summer 2020. Coastal Craftsman meets Southern Charm in this brand-new home now underway! Located in Sarasota’s most sought-after area West of...

Photo of Listing #A4450425

Unquestionably the most desirable area of town only minutes to downtown where the epicenter of activity, restaurants, cultural offerings and the city buzz is located. Combine the 5- star tree lined...

Photo of Listing #A4450434

Located on a lush corner lot, this Craftsman style home is a testament to the grace and charm of yesteryear. An exceptional location only one street south of downtown Sarasota, a charm factor off t...

Photo of Listing #A4450069

If you are looking for Coastal style with a modern twist, you have found it. Built by Najjar Construction, this light and bright 3 bedroom (WITH OPTIONAL 4TH BEDROOM)/4 bath SOUTHERN EXPOSED pool h...

Photo of Listing #A4450061

Fabulous lifestyle awaits you at Phillippi Landings. Drive over the private bridge to your gated gorgeous condo that affords superb views over Phillippi Creek, the Intra-coastal Waterway and out t...

Photo of Listing #A4449922

Welcome to this lovely renovated Landings Carriagehouse- a true delight with wood floors throughout, new exterior sliding doors and windows, new solid core interior doors, updated fans and LED ligh...

Photo of Listing #A4449326

Price based on appraised value. Enjoy comfort, style, and functional design in this impressive “West of Trail” home. Sited on an oversized lot in McClellan Park, one of the area’s most sought after...

Photo of Listing #A4449499

Indulge in a “West of the Trail” lifestyle at this charming four-bedroom home. The sought-after Hudson Bayou neighborhood is in a central spot, just minutes from downtown Sarasota’s lively locale, ...

Photo of Listing #O5821514

Beautiful updated 3/2 with 1 car garage coach home with lake/fountain view in Sarasota’s finest west side community – The Landings. Tastefully updated throughout and move in ready. Cathedral ceilin...

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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 December 13th, 2019 at 5:30am EST.