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: 252
Average Price: $1,309,717
Highest Price: $5,750,000
Lowest Price: $239,900

Real Estate For Sale West of Trail Sarasota

252 Properties Found. Page 1 of 6.
Photo of Listing #A4432516

This property features a large lot with a home built in 1940 with wood floors throughout, two bedrooms, one bath, bonus room off the master bedroom that could be used as a den or office. The living...

Photo of Listing #A4433464

This custom built and meticulously cared for home sits West of the Trail, just steps from Morton’s Market and Libby’s Restaurant, plus more than a dozen more restaurants and retail shops. A wall of...

Photo of Listing #A4433895

West of the Tamiami Trail bungalow in the desirable Granada neighborhood. The historically designated Mediterranean Revival home located on a lovely treed street is minutes from downtown Sarasota, ...

Photo of Listing #U8042524

Darling light and bright 3-bedroom, 2-bath West of Trail home with causal ambiance and steps away from cafes, restaurants, grocery and Red Rock Park. Completely remodeled home in 2012 boasting a ne...

Photo of Listing #A4433333

Welcome to the Landings Carriagehouse II, a collection of condominium villas surrounded by majestic trees and mature landscaping. The Landings is a secure, gated community just south of downtown S...

Photo of Listing #A4430429

Views, Views, Views! The best view in Eagles Point at the Landings from this corner penthouse where you will enjoy panoramic south, west, and north views of the Intracoastal Waterway and Phillippi ...

Photo of Listing #A4430811

West of Trail! You'll know you're in the tropics, living in this beautiful stilt home with a wrap around porch, eye-level with the trees. Feel the breezes wafting through the elegant french doors i...

Photo of Listing #A4431982

This one of a kind 1925 Spanish Mediterranean home is in the highly sought after west of trail location. Within walking distance to Southside Village or Selby Gardens and just one mile from downto...

Photo of Listing #A4427269

Spanish Med style home built in Sarasota during the building boom of the 1920's. According to a recent appraiser, this dwelling due to size and functionality, has reach the end of its economic life...

Photo of Listing #A4432569

This home is the ultimate illustration of British West Indies, nestled on a mainland tree-lined Street in what is considered Sarasota’s best neighborhood, Cherokee Park. Between downtown Sarasota a...

Photo of Listing #A4426804

This newly constructed home is exceptional in every possible way from its private, deep, oversized West of the Trail lot, creates a unique sense of privacy. Attention to detail is seen throughout t...

Photo of Listing #A4433125

Superb West of Trail location within walking distance to popular Southside Village shops, restaurants, Sarasota Memorial Hospital and Southside Elementary School. Beautiful custom details and fines...

Photo of Listing #A4433140

A West of the Trail Cul de Sac home located in Sarasota's most desirable location. This home is close to Downtown Sarasota, Siesta Key Beach, and walking distance to Red Rock Park, Restaurants, Ban...

Photo of Listing #A4433261

MULTI OPTION USE PROPERTY. Great WEST OF THE TRAIL location near Red Rock Park. Located Next to Million Dollar New Homes under Construction. Situated on almost 1/2 Acre Lot at the End of a Cul-de-s...

Photo of Listing #A4431576

Located West of the Trail in the highly sought after historic Avondale, this enticing, beautifully appointed residence is now available for purchase. Presenting alluring curb appeal with extensive ...

Photo of Listing #A4432827

Begin your dream home West of the Trail. This charming four-bedroom pool home is situated on a corner parcel spanning nearly a quarter-acre of lush, manicured property. Waiting for you to renovate ...

Photo of Listing #A4432886

This picturesque homesite is located in one of Sarasota’s most sought-after West of Trail neighborhoods, Poinsettia Park. Located just a short walk or bike ride to Southside Village shops and dinin...

Photo of Listing #A4428627

Amazing opportunity to build your dream home West of Trail! The area of High Point is a small enclave just south of Downtown Sarasota. The lot is perfectly situated on a dead-end street offering tr...

Photo of Listing #A4432539

This BAYFRONT cottage, West of Trail, in-town location of distinction seems worlds away yet enjoys easy accessibility to the very best Sarasota has to offer. Hidden behind the gates of OYSTER BAY L...

Photo of Listing #A4432602

Looking for a fabulous 2/3 bedroom condo in downtown Sarasota? A small enclave of residential townhomes, this is a jewel. One of 12, this 1st level unit on a quiet no-through street on the Hudson B...

Photo of Listing #A4431400

Tucked away in the exclusive West of Trail area of Sarasota, Oyster Bay Landings is a secluded waterfront enclave of 14 homesites. Bring your own builder to this waterfront property and make your d...

Photo of Listing #A4432142

Perfectly located between downtown Sarasota and Siesta Key, this soft contemporary home is within easy reach of excellent schools and a world of cuisine, culture, shopping, beaches and waterfront. ...

Photo of Listing #A4431395

This West of Trail in-town location of distinction seems worlds away yet enjoys easy accessibility to the very best Sarasota has to offer. Hidden behind the gates of Oyster Bay Landings is a windin...

Photo of Listing #A4432440

This BAYFRONT, West of Trail, in-town location of distinction seems worlds away yet enjoys easy accessibility to the very best Sarasota has to offer. Hidden behind the gates of OYSTER BAY LANDINGS ...

Photo of Listing #A4432309

WATERFRONT LOT IN PARADISE SHORES...Located just minutes south of downtown Sarasota, this property is all about enjoying the Florida lifestyle. Located on a third of an acre, (15,000+ SF) and situa...

Photo of Listing #A4432063

This custom designed contemporary home is located one of the most sought after areas in Sarasota. Within one block of Southside Village and just minutes from Siesta Key and Downtown Sarasota, this ...

Photo of Listing #R4901457

West of the Trail Beautiful 2 Bedroom 1 bath Cottage in Granada, close to everything including Siesta Key Beach, Downtown Sarasota , original wood floors, marble floors in kitchen and bath very lar...

Photo of Listing #A4429293

West of Trail building opportunity on very upscale street. This real value here is in the land. But if you're looking for the hard to find 1 bedroom 1 bath home than you are in luck. The home...

Photo of Listing #A4431782

HUDSON BAYOU - WEST OF TRAIL HOME WITH GUEST HOUSE! The main house consists of 3 bedrooms and 2 full baths and the guest cottage has a living room, bedroom, full bath and kitchen area with a combin...

Photo of Listing #A4431841

Entering this Landings Treehouse and you are immediately met with a feeling of warmth and calm- updates are abundant starting with the wood flooring on the main level, updated sliding doors, “crisp...

Photo of Listing #A4430736

Located in desirable West of the Trail, this two story, unique, multifamily 1930's home is back on the market! This space has tons of character and with some work you can make it all your own. Main...

Photo of Listing #A4429273

One of the best locations in Sarasota with AMAZING unobstructed views, situated on a ¼ acre lot on the Sarasota Bay. Come see this Fabulous Home which is a only a few minutes away from such stores ...

Photo of Listing #N6104891

This Contemporary Coastal home can be found in the heart of one of Sarasota’s sought-after walking neighborhoods. Built in 2015 by Allegra this home is filled with vaulted ceilings, open living spa...

Photo of Listing #A4431129

One or more photo(s) has been virtually staged. You have fallen in love with the Landings, for its beauty, it’s security, it’s West of Trail location. If you have been waiting for a coveted single...

Photo of Listing #A4426115

Inspired by the traditional Dutch Colonial Caribbean influenced architecture found on the island of Bermuda, this 2011 built, LEED Platinium Certified dwelling, finds itself right at home in the c...

Photo of Listing #A4430885

Artfully redesigned and brilliantly executed in 2017/2018, this 3 bedroom + office, 3 bath home has been expertly renovated with a keen eye for beauty and functionality. A refreshing and vibrant 2,...

Photo of Listing #A4430615

** MUST SEE ** SELLER MOTIVATED, BRING AN OFFER ** Oyster Bay Estates Presents a Botanical Paradise in this Fantastic 2 Bed, 2 Bath Pool Home. Sitting on a 15,500ft2 (.35 acres) lot, native plantin...

Photo of Listing #A4430493


Photo of Listing #A4430790

Great Opportunity to own in highly desirable Poinsettia Park, this private, west facing home is just two blocks from Siesta Drive. Come check out a 3 Bedroom 2 Bathroom home with a side facing gara...

Photo of Listing #A4430287

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 #A4430053

This picturesque homesite is located in one of Sarasota’s most sought-after neighborhoods. Located in Poinsettia Park, this lot is a short walk or bike ride to Southside Village shops and dining an...

Photo of Listing #A4430280

Fantastic opportunity in the coach houses of Landings South VI. This spacious and bright second floor end unit has 3 Bedrooms and 2 Baths. The great room has high ceilings and sweeping views across...

Photo of Listing #A4429894

You won't want to miss this ready to move into, 2 story Figi model. "Resort Style Living Near Downtown Sarasota" This luxurious condo is located in a community loaded with amenities. This condo h...

Photo of Listing #A4429852

Separated from Osprey Avenue by a gate post adorned with a tiled Cherokee rose and a low, stucco wall, you’ll find Cherokee Park, an exclusive neighborhood with grand lots platted in 1926, situated...

Photo of Listing #A4425354

Ideally located with an overlook of Hudson Bayou and a glimpse of Sarasota’s night lights. You will look down onto the fishing pier and spacious grounds of Central Park. Enjoy the proximity and e...

Photo of Listing #A4429749

Elevate your level of relaxation; reawaken your childhood dreams and live in the trees. This treehouse is located in a gated, waterfront community, west of the trail (US 41) known as The Landings. ...

Photo of Listing #A4428276

Live your fabulous Sarasota lifestyle in this 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 squar...

Photo of Listing #A4429522

An impeccable balance of form and function, this new construction, contemporary home is located West of the Trail in the Granada neighborhood near Siesta Key, Southside Village, A-rated schools 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.

Listing information last updated on April 21st, 2019 at 8:30am EDT.