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: $1,270,833
Highest Price: $7,500,000
Lowest Price: $229,900

Real Estate For Sale West of Trail Sarasota

230 Properties Found. Page 1 of 5.
Photo of Listing #A4438955

This rarely available ground level Landings Coachhouse is located directly across from the Landings nature trail. Enjoy leisurely strolls down to the Bay or the serene view of the fountain and pond...

Photo of Listing #A4434854

This custom home in The Landings is located at the end of a cul-de-sac on a beautiful large Tropically Landscaped lot. Enjoy entertaining with the magnificent indoor and outdoor living spaces in t...

Photo of Listing #A4432462

Spectacular and truly unique unit at Carriagehouse 2. This lovely home is one of a kind. Warm and inviting with every attention to detail. A light diagonally laid tile runs throughout the home and ...

Photo of Listing #T3181067

Beautiful 2-story custom built home in Historic Granada. Surrounded by rare lush tropical trees and plants, this home built in 2008 has 4 bedrooms, 4 baths and its own private elevator. It has a g...

Photo of Listing #A4438225

Pre-Construction. To be built. A modern vision to be built in McClellan Park by notable luxury homebuilder Allegra Homes, the “Kristi Ann” model features 4 en-suite bedrooms, a 3-car garage, a den/...

Photo of Listing #A4438342

SUNSET VIEWS WITHOUT PAYING THE PRICE! The Intracoastal Waterway and Siesta Key outline the bay vegetation that backdrops fountained lake vistas. This is an outstanding value on the second floor ...

Photo of Listing #A4437357

BUILD YOUR DREAM HOME! Rarely available, estate sized parcel located West of Trail in sought after Granada Park. This 1/2 acre property is being sold as one parcel, but can be subdivided into two...

Photo of Listing #A4437386

BUILD YOUR DREAM HOME! Rarely available, estate sized parcel located West of Trail in sought after Granada Park. This 1/2 acre property is being sold as one parcel, but can be subdivided into two...

Photo of Listing #A4427269

This home is a Historically Designated by the City of Sarasota & there are potential benefits provided by the City and County for approved additions to the structure. If you want to live in the cha...

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 #A4437882

This is the WEST OF THE TRAIL updated bungalow you have been waiting for! Oozing with character and charm, the main home features freshly refinished original hardwood floors, crown molding, built-i...

Photo of Listing #A4437176

Enjoy all that Sarasota has to offer from this great central location West of Trail, just minutes from Red Rock Park, The Field Club, Southside School, Southside Village, Siesta Key and Downtown Sa...

Photo of Listing #A4438373

From its quiet West of the Trail street and its sprawling, fenced yard shaded by mature trees, to the cozy woodburning fireplace and the rich, natural oak hardwood floors, this 3BR, 2.5-bath solid ...

Photo of Listing #A4437946

Location, landscaping, updated interiors—you can have it all! Known as the Bamboo Bungalow, this charming home is centrally located in a desirable west-of-the-trail neighborhood— less than 1 mile t...

Photo of Listing #A4435438


Photo of Listing #A4437740

A fantastic condo alternative giving you privacy, all the newer-high-end appointments, desirable great room living, a two car garage AND just a short stroll to Southside Village where you can enjoy...

Photo of Listing #A4437601

**HISTORY AND S-P-A-C-E AND LOCATION COLLIDE!!** 1936 Built unique home that was relocated from across the street in the 80's. This is a ONE-OF-A-KIND home. Amazing location on a spacious corner lo...

Photo of Listing #N6105856


Photo of Listing #A4437463

Private garden enclave, stately and spacious, open and airy, urban and interesting spaces. Vaulted ceilings grace the foyer of the front entrance, leading to formal dining and living areas. Several...

Photo of Listing #A4437393

LOCATION! LOCATION! LOCATION! Well Maintained Home in City Limits with Great Weekly Rental History, Professionally Managed, Repeat Satisfied Clients are booked into 2020. This property offers an op...

Photo of Listing #A4437407

Here it is! Absolutely adorable home in prime WEST OF TRAIL location on Siesta Drive, the gateway to Siesta Key! This is a perfect opportunity for a vacation rental, move in ready with prime locat...

Photo of Listing #A4437202

Welcome home to this sprawling and impeccably designed 3 bedroom plus office custom home on a 17,764 square foot cul-de-sac lot in the West of Trail and gated Landings community. The residence feat...

Photo of Listing #A4437028

Located West of the Trail, in the Oyster Bay area of Sarasota, sits this spacious 5 bedroom, 2-story home that was built new in 2013 and wonderfully maintained by its original owners. The property ...

Photo of Listing #A4436942

Pre-Construction. To be built. Pre-Construction - The Coquina by Heritage Builders is ideally situated in West Bay, a private gated enclave of only 4 luxury single family residences in Sarasota's m...

Photo of Listing #A4436565

On one-half of an acre of boating water nestled in the private setting of Harbor Acres lies this Mid-Century home, originally built for Ken Thompson, Sarasota’s City Manager from 1950 to1988, and h...

Photo of Listing #A4436668

Build your dream property on prominent South Lake Shore Drive– a long-established, highly-regarded Oyster Bay Estates neighborhood. Tucked away on Sarasota’s mainland, this private waterside oasis ...

Photo of Listing #A4436601

Now priced below appraisal! Welcome home to this terrific West of Trail residence located a short walk to the bay and in the sought-after Bayview Heights neighborhood and Southside School district...

Photo of Listing #A4436483

VACANT LOT WEST OF TRAIL READY TO BUILD ON YOUR SLICE OF PARADISE - Choose your own builder on this West of Trail lot located on the way to Siesta Key beach. The lot is adjacent to 2 recently built...

Photo of Listing #A4435918

Charming and magical define this 1920’s 3BR/2 bath, plus Guest Cottage, west of the trail home. This craftsman influenced home, located close to Southside Village, is a one-of-a-kind, must-see! His...

Photo of Listing #A4436047

Pre-Construction. To be built. Master builder Allegra Homes expanded two-story “Gloria” plan infused with an atmosphere of sophistication and refinement. This 3,321-square-foot residence is irresis...

Photo of Listing #A4436221

Pre-Construction. To be built. A vision to be built in McClellan Park by notable luxury homebuilder Allegra Homes, the “Kristi Ann” model features 4 en-suite bedrooms, plus a half bath, a 3-car gar...

Photo of Listing #A4436336

Tastefully updated, move in ready ranch on very upscale West of Trail street. Million dollar homes line this street and this sits on one of the best lots at end of the street. Here is your op...

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 #A4436182

An easy move-in to this elegant 3 bedroom 3 bath great room floorplan home. Rarely is there a property that has been updated to this extent prior to listing. New circular paver driveway, new pool ...

Photo of Listing #N6105623

One or more photo(s) has been virtually staged. Welcome Home to one of Sarasota's Most Premier neighborhoods West of the Trail. Cherokee Park is highly sought and recognized as Sarasota's oldest an...

Photo of Listing #A4436235

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

Photo of Listing #A4434953

West of Trail newly renovated home by a local designer will leave you captivated by the state of the art, yet enduring finishes of this home. Updates include all new kitchen and appliances, two new...

Photo of Listing #A4433333

Price reduced $40,000. 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 ...

Photo of Listing #A4435864

3 bedroom 2 bath home in Poinsettia Park with a beautiful Oak Tree upon pulling into the driveway. This west of the Trail home is concrete block with new hardwood floors throughout the living areas...

Photo of Listing #A4435728

West of the Trail Retreat - Don't Delay! This great 2/3 Bedroom, 2 Bath remodeled home is ready for you NOW! List of updates include Wood burning fireplace, 17 inch Tile (with inlays), Carpet, Kitc...

Photo of Listing #A4438359

Cute and cozy one story single family home in highly sought after "west of trail." This home has been completely updated - new kitchen and solid surface counters tops, new appliances, all new floor...

Photo of Listing #A4432876

Experience privacy and elegance along the shores on the Hudson Bayou! Built to enjoy the seascape with a timeless relationship to the water, this custom home with over 4,000 sf of living space feat...

Photo of Listing #A4434816

Under Construction. From noted luxury home builder Allegra Homes is the ever popular “Kristi Ann” plan, an irresistible West of Trail haven of uncompromised construction standards, fabulous archite...

Photo of Listing #T3171206

This detached Treehouse condo is on a corner lot filled with lush landscaping and peaceful surroundings. Kitchen has been expanded by enclosing a front porch and adding an area for a breakfast room...

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 #A4434763

Investor Alert!!! Hard to find this location at this price! West of the trail, 0.5 miles from Southside Village, close to hospital, downtown, Siesta Key, etc, etc..Cute 1920's craftsman cottage (gr...

Photo of Listing #A4434489

Welcome to this centrally located, downtown living complex and all that it offers, that welcomes your pet! 2/2.5 updated with hardwood flooring throughout, granite kitchen, stainless steel applianc...

Photo of Listing #A4434317

On Sarasota’s shoreline and most desired address within Harbor Acres, discover unequivocal excellence – whether building new or enjoying the current and impeccably updated residence. Surrounded by...

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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 June 20th, 2019 at 3:30pm EDT.