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: 136
Average Price: $1,241,292
Highest Price: $14,000,000
Lowest Price: $203,900

Real Estate For Sale West of Trail Sarasota

136 Properties Found. Page 1 of 3.
Photo of Listing #A4489183

Welcome to the highly sought out Central Park II condominiums, located in the heart of downtown Sarasota. This community offers a luxurious resort lifestyle at a fraction of the cost you would expe...

Photo of Listing #A4488799

Location and Pricing is Everything for this Clean & Well Conditioned End Unit Condo in the Gorgeous Landings Development! Privacy is key as the home backs up to the Preserve for no rear neighbors. ...

Photo of Listing #A4487940

One or more photo(s) has been virtually staged. Welcome to The Landings and this move-in-ready two bedroom, two bathroom “West of the Trail” home. Upon entering this gated community, experience lus...

Photo of Listing #A4487521

A two bedroom and two bath condominium with a dock on Philippi Creek. This unit has great views of the creek and the inter-coastal waterway. The private elevator allows easy access. Large kitchen ...

Photo of Listing #A4489029


Photo of Listing #A4487121

BAYFRONT home built in 1967.... 2 bedrms. 2-1/2 bath w/1/2 bath downstairs. It has a large, deep, open pool w/paver decking. An oversized lanai wraps around the back of the home. It has a long d...

Photo of Listing #A4488935

Pre-Construction. To be built. Heritage Builders is pleased to unveil the Cayman. Thoughtfully designed, this West Indies inspired custom home presents a rare combination of quality and elegance se...

Photo of Listing #A4485824

Classic 1920s craftsman cottage located west of the Trail located in one of the most popular parts of town. This 2 bed, 2 bath + den + guest house has retained its original character and oozes cha...

Photo of Listing #A4488079

Natural light filled, private, and peaceful canopy living in sub-tropical landscape. Treehouse section of the Landings community is located West of the Trail and offers 3 Bedrooms/2.5 baths with op...

Photo of Listing #A4488583

Inviting and comfortable 3-bedroom Coachhouse in the coveted Landings community. The desirable upper floor end-unit provides extra light and views of the lush preserve. Sold Turnkey furnished, thi...

Photo of Listing #A4487911

Mid-Century Modern that will truly delight fans of this architectural style. Lovely setting west of the trail with easy access to Siesta Key, Southside school and village, Sarasota Memorial and al...

Photo of Listing #A4488112

Get ready to fall in love with this stunning Modern Farmhouse design located on one of the best West of Trail streets nestled between Cherokee Park and Harbor Acres. From the moment you turn down ...

Photo of Listing #A4488644

The Villas at Eagle’s Point in The Landings. One of just four lakefront villas. Rarely available end unit. All on one level: 3 bedrooms and 3 full bathrooms, open plan living area with high cei...

Photo of Listing #A4487824

Enjoy the convenience of downtown living, boating, kayaking, shopping and outdoor lifestyle at your very own oasis on Hudson Bayou in downtown Sarasota. This light and airy 2/2 condo boasts beautif...

Photo of Listing #A4488596

Bring your boat and live downtown. West of the trail waterfront condo on the Hudson Bayou. Beautifully renovated 3 bedrooms, 2 bathrooms, a deeded dock and a garage, this condo is an incredible opp...

Photo of Listing #A4487508

Under Construction. Currently under construction by renowned, award-winning Platinum Coast Construction with expected completion Summer 2021, this modern masterpiece has been planned with uncomprom...

Photo of Listing #A4488438

This stunning West of the Trail home features everything you need for your family at an incredible value for this coveted address. The newer construction home encompasses over 3,500 square feet of ...

Photo of Listing #A4487573

Gorgeous home in Harbor Acres.

Photo of Listing #A4488083

Unlike any Treehouse you have ever seen. Owners have redesigned this freestanding townhouse to create amazing living space. There is almost nothing that has not been updated. A true 3 bedroom 3 ...

Photo of Listing #A4485960

Located West of the Trail in Granada Park, an alluring maintenance-free gated community, this delightful residence combines the feeling of small-town charm with relaxed Florida living. Surrounded b...

Photo of Listing #A4487838

Directly across Tamiami Trail from the newly revived Sarasota Arts Museum, this distinctive West of Trail home resides on an exclusive street known as, High Point Circle! Here homes are full of Sar...

Photo of Listing #A4487518

Meticulously maintained, “Custom West of Trail Pool Home”, with three car garage, on a cozy cul-de-sac. The high ceiling height and tray ceilings, combined with the abundant strategically placed wi...

Photo of Listing #A4487700

Build your dream home in this desirable North Siesta Key location, only two blocks to Shell Road Beach. Building lots on Siesta Key are becoming rare - this large building lot in the exclusive isla...

Photo of Listing #A4487530

Pre-Construction. To be built. Awarding winning Allegra Homes in the sought after area of West Of Trail. Near the gateway to world famous Siesta Key, this one level home with 3 car garage is Florid...

Photo of Listing #A4487777

3D Matterport scan available, click virtual tour #1. Listed below January 2021 appraised value! West of the trail, seconds from the north bridge, to the voted #1 beach Siesta Key! Located in the c...

Photo of Listing #A4487930

Pre-Construction. To be built. *Photos used are of a previous Allegra Homes model but will have many similarities.

Photo of Listing #A4483701

Beautiful, sprawling ranch in the much sought-after Cherokee Park neighborhood, west of the Trail. This charming four-bedroom, three-and-a-half-bath home boasts many wonderful features, including u...

Photo of Listing #A4485906

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 #A4486876

Privately situated at the end of the street on a lush corner lot in the highly desirable Oyster Bay area, this home has a special charm. The gardener will love the large yard with meandering paths ...

Photo of Listing #A4487447

FANTASTIC LOCATION! Homeowners and Investors - Here's your chance to own a home within city limits, on one of Sarasota's most desirable "FLOWER" streets West of Tamiami Trail. This adorable 2 bdrm ...

Photo of Listing #A4487628

Ideally located in the heart of Sarasota, the Central Park I complex is only a block from Selby Gardens and another block from Marina Jacks. The Sarasota downtown area is right around the corner. I...

Photo of Listing #A4486284

The Cloisters is one of the most desired locations in The Landings A GATED COMMUNITY with 24 hour security. Visit #1 Siesta Key Beach only a 2 miles away or the great Gulf Gate Mall with all the sh...

Photo of Listing #A4486913

Positioned in the coveted neighborhood of Bay Point Park where very few homes come on the market this very desirable west of trail home is within walking distance of downtown, the bay front , South...

Photo of Listing #A4487110

Located in San Remo, this abundant property provides extraordinary privacy, waterfront views, and the premier opportunity to build your dream estate on deep sailboat water. Sprawling across more th...

Photo of Listing #A4486714

Welcome to Mandarin Park, a gated cul de sac of only eight distinct homes located in the highly desirable West of Trail location offers privacy with fabulous access to restaurants, shopping, hospit...

Photo of Listing #A4486955

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 o...

Photo of Listing #U8108131

Attention Investors! Incredible opportunity to renovate or build new construction West of the Trail in Hudson Bayou, Sarasota. 2020 has shown new construction sales on Prospect Street over $2.5 Mil...

Photo of Listing #A4485954

Tucked into a private, tropical setting, this Landings Treehouse embodies the true essence of a Treehouse. Tastefully updated yet in keeping with the rustic feel of the surroundings. A seamless flo...

Photo of Listing #A4486575

Old charm (1925) meets contemporary space (2012) on one of the most popular streets WEST of TRAIL. Enjoy a one block walk to the shops & restaurants of Southside Village & Morton's Market! This UNI...

Photo of Listing #A4486694

If you're the type of person who likes 'the best of both worlds,' this townhouse is for you: Imagine living in a resort setting--pool, hot tub, tennis court, gym, bike shed, dock, kayak launch, clu...

Photo of Listing #A4477606

The moment you step through the front door, you will recognize the resolute commitment to Quality, Detail and Design. With multiple Vignette's to explore, this home was Built for the most discernin...

Photo of Listing #A4485767

Under Construction. NEW Construction~ Relaxed Modern by award winning Allegra Homes is in Sarasota's most sought after area, West of Trail. Just a few blocks South of Southside Village and Sarasota...

Photo of Listing #A4484844

This is a fabulous sought after Oyster Bay home on almost ¾ of an acre boasting 5 bedrooms, 4 bathrooms and a 3-car garage. The home was extensively updated in 2012 to create a stunning open plan ...

Photo of Listing #O5911984

This West of the Trail hidden gem is nestled in the discrete Shoreland Woods neighborhood in the heart of Sarasota. It comprises of 1.43 gated acres with 100' of bay front. Live Oak trees provide a...

Photo of Listing #A4484439

This is one of the most in-demand communities in the Sarasota area--and rightfully so: You have the convenience of living adjacent to downtown while enjoying a wide variety of resort amenities. I...

Photo of Listing #A4484155

Tucked away amid the serene natural beauty of The Cloisters at The Landings, this two-story home provides the ultimate in privacy. The spacious and inviting five-bedroom home creates an immaculate ...

Photo of Listing #A4485065

Live nearby everything you love in one of Sarasota's most sought after locations the "West of Trail" area. Location is what it is all about - close to Southside Village, Morton's, Sarasota Memorial...

Photo of Listing #A4484942

This charming home delights all senses. Positioned on a premium lot with wide views of the lake and fountain and good separation from neighbors, this 3 bed 2 bath home offers 2500 sq ft of comforta...

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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 23rd, 2021 at 6:41pm EST.