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: 230
Average Price: $1,214,237
Highest Price: $7,500,000
Lowest Price: $200,000

Real Estate For Sale West of Trail Sarasota

230 Properties Found. Page 1 of 5.
Photo of Listing #A4457657

Coveted water view at Landings Carriagehouse 1. With views down the full length of the pond this unit is waiting for the right buyer to make it his own. The larger 2 bedroom/den floor plan lives li...

Photo of Listing #A4459896

A Sarasota gem that is rarely available. This boutique British Colonial style condominium residence is located on Hudson Bayou with deep sailboat water access and deeded boat docks for each unit. E...

Photo of Listing #A4460200

Spacious and bright end unit at at Carriagehouse 2 in the Landings. The interior has been completely redesigned to maximize the living space. The large master bedroom suite includes two walk-in clo...

Photo of Listing #A4460206

West of the Trail and just 2 short blocks from Southside Village is where you will find this 2 bedroom, 2 bathroom, block construction, Florida ranch style home ready for either a complete renovati...

Photo of Listing #A4460210

West of the Trail and only 2 blocks from Southside Village is where you will find this 12,000 square foot parcel. This 100’ wide by 120’ deep lot currently with a 2 bedroom, 2 bathroom, block const...

Photo of Listing #T3205295

Short Sale. .

Photo of Listing #A4459791

Fabulous Lake View from this two bedroom two bath downstairs coach house. This is the ideal location across from the Landings Raquet Club with all the amenities. Enjoy sitting on the deck and wat...

Photo of Listing #A4459931

Situated in the heart of Harbor Acres, one of the most enviable addresses in all of Sarasota, sits a one-story mid-century ranch that has been extensively renovated. Sited on an oversized corner lo...

Photo of Listing #A4458538

This is a great investors opportunity. This property is located on the west side of the trail and has two separate properties. Must see to appreciate its potential.

Photo of Listing #A4459431

The "Move-In-Ready", bar has just been re-set! Nestled in the heart of one of Sarasota finest gated communities "The Landings", is where you will find this astonishing 3 bedroom, 2 bath gem. No exp...

Photo of Listing #O5843318

Beautiful 4 bed/2 bath pool home on a quiet west of the trail street so close to shopping restaurants and the beach. New granite tops, new stainless steel appliances, new vinyl plank flooring, new ...

Photo of Listing #A4459323

Take your place in the legacy of the Sarasota art colony. Nestled under whispering bamboo, this .42 acre estate includes the main residence, a garage, and an art studio. The house was designed in 1...

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 #A4459480

Delight in the waterfront living in a serene sanctuary with easy access to both Sarasota Bay by boat,Sarasota’s shopping, dining and cultural amenities and Siesta Key beaches just a short drive awa...

Photo of Listing #A4459528

Views of nature and Phillippi Creek abound from this 2nd floor, southwest-facing 2 bedroom + den / 2 bath condo in the coveted waterfront building at Phillippi Landings. The elevator opens directly...

Photo of Listing #A4457845

Contemporary 3 Bedroom plus media room pool-home below $600,000 west of the trail! Located in the 'A' rated Southside school district, this home will not be long on the market! Completely redone in...

Photo of Listing #A4457735

This mid-century contemporary residence, built in 2014, is ideally located just blocks to the Bayfront and downtown Sarasota with its endless offerings. The home exudes chic sophistication with its...

Photo of Listing #A4458491

Live close to it all and enjoy maintenance free living in this spacious 3 bedroom, 2 bath end unit Landings coach home with peaceful preserve views. Enter through the first floor foyer and walk up ...

Photo of Listing #A4459314

West of Trail family home in San Remo, Sarasota's gateway to Siesta Key. Centrally located with deeded access to Roberts Bay, this spacious 2,696 square foot home features 4 bedrooms, 3 baths, open...

Photo of Listing #A4458756

Location, Location, Location! Wow! West of Trail Waterfront under $1.5M! Calling all Boaters! No bridges to the Bay! Deep water dock with a 10,000 lb boat lift! Only one minute to the open waters o...

Photo of Listing #A4458878

Distinctive contemporary transformation of the original Treehouse in the Landings— nothing has been left untouched. Just installed 2 new HVAC systems. Beautiful tile and bamboo flooring throughout ...

Photo of Listing #A4458993

Looking for an end unit downstairs coach house on the Lake? Look no further your journey is over. This two bedroom , two bath, unit has fabulous lake views and a private setting. This coach house...

Photo of Listing #A4457740

Located in one of Sarasota's most desired areas, "West of the Trail" in the coveted Oyster Bay area, this fabulous family home boasts 4 large bedrooms with spacious closets, 4 and one half baths an...

Photo of Listing #U8073534

Completely updated affordable living in the heart of downtown Sarasota! This one bedroom two story condo is ideal for your home away from home or year round living. Low fees that provide complete a...

Photo of Listing #A4458911

Charming Spanish West of Trail ranch that is perfect for the buyer that wants a great location yet doesn't need a huge home. Very close to vibrant downtown Sarasota, bustling Southside Village and...

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 #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 #A4458735

One of the prettiest homes in Harbor Acres, this four bedroom custom home sits beautifully behind graceful gates on a large parcel of land. Warm & inviting the exterior may remind you of a French ...

Photo of Listing #A4457287

How do you describe the indescribable? In one word-sublime. This Spanish-retro pays homage to its 1920's Art-Deco heritage with lovingly restored vintage touches blended with modern sophistication....

Photo of Listing #A4458025

WEST OF TRAIL. Experience the casual but elegant custom built home on a private tropical landscaped lot over a half an acre on a quiet cul-de-sac. Location is close to all the wonderful amenities ...

Photo of Listing #A4458536

This has to be one of the best waterfront opportunities in the marketplace today. Located on a boat basin in the beloved neighborhood of Oyster Bay, its setting is magical with a large backyard an...

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 #A4457496

Modern meets Classic meets Waterfront! Welcome to your new home where a large front porch invites you to discover the coastal lifestyle that Sarasota is known for just seconds from downtown. Once i...

Photo of Listing #A4457958

This contemporary Landings Treehouse fuses form with function as bright, captivating spaces and light-filled living sets the stage for comfort and elegance. This two-story, three-bedroom residence ...

Photo of Listing #A4457978

Rare 175' wide lot in popular west of trail Granada subdivision. value for size, 3 ½ lots, not sub-dividable.

Photo of Listing #A4457885

Incredibly charming "West of Trail" home with detached guest quarters. This awesome family compound is situated in one of the areas most sought after communities encircled by A rated schools, down...

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 #A4457420

Newer West of the Trail home on rare over-sized lot is ready today! This 2014 Arthur Rutenberg masterpiece shows like a model paired with a spacious backyard and beautiful live oak centerpiece. The...

Photo of Listing #A4457460

Rarely available ground floor end unit with open water views across Hudson Bayou. This unit offers the convenience of downtown living on the waterfront. Easy walk to Selby Gardens, the bay front an...

Photo of Listing #A4457464

Own part of one of the best neighborhoods in Sarasota! This quarter acre lot is in a unique setting with 2 structures currently on the property- The meticulously maintained 1 Bedroom, 1 Bath cottag...

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 #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 #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

Move in Ready!! 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. . This West of Trail home is j...

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 #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...

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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 February 18th, 2020 at 8:45am EST.