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

Real Estate For Sale West of Trail Sarasota

257 Properties Found. Page 1 of 6.
Photo of Listing #A4427077

Nestled under mature trees in the desirable community of The Landings, this 3-bedroom, 2-bath pool home is in pristine condition and ready for move-in. A split floorplan features two guest bedrooms...

Photo of Listing #A4425625

From award-winning Allegra Homes, this 2019 model home has a floor plan concept that showcases a combination of indulgence and practicality. Landmark location west of trail and just 3 blocks south...

Photo of Listing #A4427303

Situated on a cul-de-sac tucked behind majestic live oaks you will be enchanted by the charm of the setting of this custom home. A sprawling courtyard style family residence reminiscent of Cape Co...

Photo of Listing #A4425734

This is a shining example of impeccably-restored Colonial style. This exquisite property spans a 3-bedroom main home and 2-bedroom guest cottage, all nestled in one of downtown Sarasota’s most hist...

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 #A4421973

Deep sailboat water and the location in the prestigious Harbor Acres neighborhood highlight two of the many desirable attributes of this four bedroom, three-and-one-half bath residence set on more ...

Photo of Listing #A4427322

Come home to the Landings and this wonderful home built for a comfortable lifestyle. Situated on a cul-de sac on a circle drive this home has wonderful curb appeal. This stately look with shuttered...

Photo of Listing #A4427401

One or more photo(s) has been virtually staged. UPDATED with European style, and move in ready, Landings Carriagehouse 1 with Pond Views!! Villa updates include hurricane shutters, 24 inch tiles th...

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 #A4425029

The Landings is a highly desirable gated and deed-restricted community West of The Trail. Wrought iron gates welcome you into this well maintained 4 bedroom, 2 and a half bathroom home in the mids...

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 #A4424301

Art you can live in! World renowned and acclaimed architect, Guy Peterson, designed another modern masterpiece of remarkable craftsmanship and pure minimalist aesthetic. It all began with a vision,...

Photo of Listing #A4426631

Under Construction. Brand New West of Trail Construction- only two lots in from Orange Avenue. On the forefront of design, form and function, this custom-built one of a kind home is one you will n...

Photo of Listing #A4425602

Tranquil, private and in the heart of it all! Situated on the widest banks of the Hudson Bayou in Downtown Sarasota this remarkable custom home will simply take your breath away. Through the beauti...

Photo of Listing #A4426111

If you have been waiting for an updated coach home with a lake view, your wait is over. A renovated 3 Bedroom upstairs coach house with a lake view has just become available. Kitchen and bathroom r...

Photo of Listing #A4425835

Warm, Inviting and in a Stellar Location! Enter through the stunning, arched wood doorway, you will be met with a true sense of serenity. Every detail has been carefully thought of in this substant...

Photo of Listing #A4426411

Hands down, THE best location in Sarasota for those in love with the West of the Trail vibe combined with the 1-minute commute to the heart of downtown. This Monterey Colonial home built in 1939 is...

Photo of Listing #A4426295

Opportunity Knocks ... Private treehouse in the Landings. This spacious bank owned townhome with 3 bedrooms, 2.5 baths, over 2100 square feet of living space and separate 1-car garage. Master suite...

Photo of Listing #A4424526

Elegant and inviting home in the highly sought after community of The Landings. This tastefully updated and move-in ready 4 bedroom, 3 1/2 bath residence sits on a corner lot with mature trees and ...

Photo of Listing #A4426055

We introduce an exquisite waterfront tropical paradise, where panoramic water views surround you. Upon entering this home you will be captivated from the water views raining in on the Soaring 24 f...

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 #A4426157

The newest addition to Sarasota's iconic Harbor Acres has an impressive Sarasota pedigree — the result of a creative collaboration between Home Designer Brian Phipps, Interior Designer Tanya Burley...

Photo of Listing #A4426164

Tucked away in a prime position in Sarasota’s West of Trail area, this updated two-story home is a place for families to live well and make lasting memories. Surrounded by natural beauty and positi...

Photo of Listing #A4426130

Updated single family home with vaulted ceilings is both spacious and inviting. Featuring 3 bedrooms and 2-1/2 baths in a split floorplan, there is an additional office, 2 living areas. Oversized...

Photo of Listing #A4425575

Coastal contemporary, luxurious, and sophisticated best describes this new residence. Perfectly situated in the prestigious West-of-Trail area. The floorplan is a highly desirable layout, complete ...

Photo of Listing #A4425999

Central Park 2 is a lush oasis just on the edge of downtown Sarasota. This lovely updated condo occupies one of the best locations in the complex, overlooking the tennis courts and pool beyond. The...

Photo of Listing #A4425794

You will enter Phillippi Landings over the bridge and though the gate west of US 41. This is waterfront luxury living in a location that provides convenient access to beaches, restaurants and down...

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 #A4425512

DISCOVER this great opportunity within the lush oasis of CENTRAL PARK II ! Ideally located in building 6 with west exposure - very private. This condo needs nothing which means inherent ADDED - V...

Photo of Listing #A4425869

Under Construction. This coastal residence captivates with its impeccably designed décor and outdoor living spaces in a scenic waterfront setting only seconds to the open waters of Sarasota Bay. Lo...

Photo of Listing #A4425853

West of Trail in Historic Granada. In 1924, Charles Tyson had a vision for an ideally located section of Sarasota. Just three blocks from the bay, close to Siesta Key beach and downtown Sarasota, T...

Photo of Listing #A4425900

Endless options exist for this special property in a very sought-after neighborhood close to Siesta beaches, downtown Sarasota, the hospital and good schools. With almost ½ an acre this beautiful p...

Photo of Listing #A4424862

A spectacular Landings Executive home. Designed and built for family entertaining. As you step into the foyer of this updated home, your eye is drawn to the expansive pool and brick lanai with sunn...

Photo of Listing #N6103967

Here it is. Looking for a close to downtown condo? This complex is conveniently located at US 41 and South Osprey Ave. It combines proximity to Sarasota's downtown and buzzing culture with a park-l...

Photo of Listing #A4424026

Oyster Bay, one of the most coveted mainland locations in all Sarasota. Over 18,000 square feet of land, with a back gate to the members only Field Club. This Rancho Santa Fe style home has been i...

Photo of Listing #A4425638

2 Buildable Lots! This property was recently rezoned from RSF2 to RSF3 approved 11/28/2018 with No Stipulations and Non-Binding. Lots can be 75’x142’ (2) or 70’x142’ (1) 80’x142’(1) There is a docu...

Photo of Listing #A4425374

Outstanding value in this extensively remodeled home in the West of Trail Landings community. With just under 5000 square feet on one level with no steps up or down, there are 5 ensuite bathrooms, ...

Photo of Listing #A4425340

Luxuriate in modern, green living at this centrally-located, new construction. Built to the highest standards by GreenLife Luxury Homes and completed in 2017, this three-bedroom plus den, “West of ...

Photo of Listing #A4424458

Set in a commanding waterfront location on Hillview Drive, one of the most prized addresses in Sarasota, this simply sublime home is bestowed with scenic southern exposure, vast yet comfortable liv...

Photo of Listing #A4425317

1915 Tulip Drive is the West of the Trail gem you've been waiting for. Tucked away on a quiet corner, but still just minutes from world famous Siesta Beach, exciting Downtown Sarasota, Westfield Si...

Photo of Listing #A4424954

1804 S Orange is being sold fully furnished and will check off everyone of your boxes! If your coming here to enjoy Sarasota's winters or raising your family in the popular "West of Trail". South...

Photo of Listing #A4424752

Overflowing with charm, this custom, family-inspired home in the heart of Sarasota is a rare find. Completed in 2000, the traditional yet whimsical architecture perfectly complements a modern farmh...

Photo of Listing #A4424955

Under Construction. Under Construction - Now Available. The Captiva by Heritage Builders is situated on nearly 1/2 acre in Sarasota's coveted West of Trail area will be complete in late 2019. The W...

Photo of Listing #A4424993

Beautiful West of the Trail contemporary home in the sought-after Oyster Bay area and walking distance to The Field Club. It’s situated on ½ acre with beautiful gardens surrounding the home featur...

Photo of Listing #A4424304

Sarasota West of Trail detached townhome in Granada Park. Located between North Siesta Key and Oyster Bay, this craftsman-coastal residence offers the leisure of a maintenance-free lifestyle in a h...

Photo of Listing #C7409851


Photo of Listing #A4424450

Come build your dream home on .60 acres “West of the Trail” sitting pretty on a lake in the heart of Sarasota… centrally located close to shopping, dining, entertainment, downtown Sarasota and shor...

Photo of Listing #A4423557

What a fabulous lifestyle this home affords. Enjoy life behind the gates of The Landings, a great centrally located community just minutes to downtown and Siesta Key's world famous beaches. The L...

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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 February 17th, 2019 at 4:45am EST.