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: 218
Average Price: $1,204,965
Highest Price: $7,500,000
Lowest Price: $200,000

Real Estate For Sale West of Trail Sarasota

218 Properties Found. Page 1 of 5.
Photo of Listing #T3205295

Short Sale. .

Photo of Listing #A4464103

Home is vacant. Welcome to the only West of the Trail GATED COMMUNITY of Mandarin Park. This home is a few minutes' walk to Sarasota Memorial Hospital and is near to shops, Sarasota High School, ar...

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 #A4464087

Prime West of Trail single family home (buildable lot) located in the Oyster Bay Estates subdivision. Lot dimensions are 100' x 150' (.34 acre) Major renovation required to update this 1959 3BR/2BA...

Photo of Listing #A4464107

Prime West of Trail single family home (buildable lot) located in the Oyster Bay Estates subdivision. Lot dimensions are 100' x 150' (.34 acre) Major renovation required to update this 1959 3BR/2BA...

Photo of Listing #A4463927

This second story 3 bedroom, 2 bath Landings Coach house has the water view you have been waiting for. A north west exposure overlooking a lake with fountain. Volume ceilings in the combo living/...

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 #A4463832

The one you've been waiting for! Solar-Powered Zen 3BR/2 Full Baths/2 Half Baths + Den, Pool home with Massive Bonus 26'x28' air-conditioned space behind the two-car garage for your home-based bus...

Photo of Listing #A4460453

West of trail pool home on over 1/3 of an acre! This house is in the PRIME Sarasota location: Only a few blocks away from Sarasota Memorial Hospital and the Hillview District, less than a mile to D...

Photo of Listing #A4463688

Idyllic neighborhood living in a cul-de-sac community West of the Trail. This Westbrook home is ready for the next family to make it their own for decades to come. The property is over one-half an...

Photo of Listing #A4463411

Situated on a cul-de-sac tucked behind majestic live oaks, this enchanting custom residence blends gracious charm with everyday elegance. The sprawling courtyard home is reminiscent of the Cape Cod...

Photo of Listing #A4462512

This villa has a beautiful water view looking straight down the lake with a fountain. The Landings Carriage house villa is nestled among trees with a park like setting. This villa has 2 split bedro...

Photo of Listing #A4461312

Welcome to the Landings one of Sarasota’s most sought after gated neighborhoods “West of the Trail”. Rarely available is a unique opportunity to purchase one of the 6 Lakeview condominiums. Locat...

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 #O5851857

This condo in Sarasota offers 2 bedroom 2 baths, located on the ground level and features include kitchen with breakfast bar, good sized rooms and screened patio. The community offers a pool, clubh...

Photo of Listing #A4463211

An enchanting hideaway in desirable McClellan Park, this 5-bedroom plus den home surprises and delights with rare architecture, character-filled spaces and sweeping acreage. Stone walls enclose the...

Photo of Listing #A4463421

An enchanting hideaway in desirable McClellan Park, this 5-bedroom plus den home surprises and delights with rare architecture, character-filled spaces and sweeping acreage. Stone walls enclose the...

Photo of Listing #O5852288

West of trail Dual family, 2/1 front house plus 1/1 back cottage. Traditional style with quality Hardwood floors, woodburning brick fireplace, fully updated kitchen and bath in front house. New a...

Photo of Listing #A4463334

West of the Trail! Exceptional opportunity for a like new, furnished former Miah model home by award winning custom builder, John Cannon Homes. This spacious custom pool home offers 4BR, or 3BR an...

Photo of Listing #A4463165

5440 Eagles Point Circle is a hidden gem on Phillippi Creek at the south end of the Landings. With tranquil views over the creek, mangroves, the ICW and Siesta Key you’ll have views that are intere...

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 #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 #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 #A4463041

Only 3 properties off of Osprey Avenue in Sarasota's hot neighborhood, West Of Trail. Nice size build-able lot in the heart of it all. Home is a tear down and not able to be toured. Call for survey...

Photo of Listing #A4462623

Beautiful, true mid-century modern in desirable San Remo Estates! Sought after classic modern architecture with open floor plan, clean lines, vaulted ceilings and pristine colorful terrazzo that's...

Photo of Listing #A4462797

Stunning Oyster Bay 4460 sq.ft. estate has been carefully designed to blend into the natural setting of this secluded ½ acre property. Beautifully imagined and masterfully constructed home features...

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 #A4462492

Perfect location for this three bedroom 2 bath coach home. The bright unit looks at the lake and the tennis courts. Volume ceilings and a cheery lanai to look over the lake/fountain and enjoy the...

Photo of Listing #A4461676

Iconic modern design by world-renowned architect Guy Peterson is combined with the quality of builder Murray Homes and the landscape artistry of Michael Gilkey to create this stunning compound on a...

Photo of Listing #A4461944

LOCATION, LOCATION, LOCATION! Prime 11,360 lot with existing traditional, block construction bungalow featuring two bedrooms, one bath located in the affluent West of the Trail Neighborhood. There ...

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 #A4462202

The West of Trail modern family home you’ve been waiting for! Move-in ready, better than new, 2 blocks to Southside Elementary and oh so close to everything downtown and the beaches. Live the Sar...

Photo of Listing #A4461200

Welcome to the ‘House on Rose Street’ where simplicity and character abound! One step through the stained-glass door of this 2-story historic home and you will fall in love! You can find your futu...

Photo of Listing #A4461904

Rare find in desirable Poinsettia Park. Elegant West of Trail home, completely rebuilt in 2003. Short distance to sought after Southside School. Minutes from top ranked Siesta Key Beach and St. Arm...

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 #A4461669

One of the most charming homes in Sarasota can now be yours. Step into "Casa de Flores" and experience this historic, romantic villa residence with two guest cottages, separated by fountains, court...

Photo of Listing #A4461409

Virtual Showing available, please, contact me and I’ll send you the video.Investors or remodeling Alert! Nestled in the historic McClellan Park district, West of the trail, this property is located...

Photo of Listing #A4461681

Ideally centrally located this 2/2 end unit provides close proximity to downtown. Enjoy the close proximity and ease of walk to Marie Selby Gardens, the Bayfront Park, Burns Court and fantastic ch...

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 #A4461020

“Good things come in small packages” – and this charming Pecky Cypress Cottage truly captures that age-old sentiment. Located just a hop, skip and jump from downtown in the desirable West of Trail...

Photo of Listing #A4461123

(Virtual showings are available upon request) Peaceful preserve and lake views of The Landings serve as the backdrop of this spacious, beautifully kept 3BR residence, known for its abundance of res...

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 #A4461083

WEST OF THE TRAIL.... Great location, so close to downtown!! Very cute home with 3 bedrooms plus den, 2 1/2 baths. Pretty fenced lot, great play area and paver patio. Remodeled in 2012 with new kit...

Photo of Listing #A4461052

3 Bedroom and 2 Bathroom home West of the Trail in beautiful Sarasota. This home is on an over sized lot (12,000 sq. ft.) There is plenty of space (1800+) for living with large great room and livin...

Photo of Listing #A4461066

Wonderful opportunity to build your DREAM HOME west of the trail. This 12,000 square foot over sized lot is available. Lot is able to accommodate up to 4000 square foot home. This lot is in walking...

Photo of Listing #A4460954

Mid-Century Modern, canal-front home on over 1/2 acre in desirable Oyster Bay Estates. Easy access to Roberts Bay/Intracoastal. Partial westerly views provide for breathtaking sunsets from the exp...

Photo of Listing #U8073534

Completely updated affordable living in the heart of downtown Sarasota! This one bedroom two story condo 100% updated and move in ready! Ideal for your home away from home or year round living. Low...

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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 March 30th, 2020 at 12:30am EDT.