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: 164
Average Price: $1,188,246
Highest Price: $5,750,000
Lowest Price: $204,999

Real Estate For Sale West of Trail Sarasota

164 Properties Found. Page 1 of 4.
Photo of Listing #A4474837

Tropical Paradise located West of the Trail within the Famous Flower Streets. Minutes to your own Southside Village for restaurants, shopping and Morton's specialty grocery store with bakery,wine r...

Photo of Listing #A4474852

Your private garden home in charming and convenient Cherokee Park, situated on a 30,000 square foot lot. This traditional West of Trail home sits under a canopy of grand Oaks with sparkling Sarasot...

Photo of Listing #A4475067

Transport yourself to the countryside of France where you may ensconce yourself behind the Ivy covered walls of this gated multilevel French Chateau amidst the most glorious selection of plantings ...

Photo of Listing #A4472701

In the heart of Hudson Bayou neighborhood in Southside Village, this home oozes charm inside and out. Beautifully remodeled in 2014, the master bedroom and both bathrooms were enlarged. The ceiling...

Photo of Listing #A4474906

Spacious 5 bedroom family home in the perfect Sarasota West of Trail location — a genuine gem in highly-cherished Cherokee Park. Nestled under the canopy of mature oak trees on 1/3 acre, the buyer ...

Photo of Listing #A4474003

WOW, this is an adorable cement block/stucco home that has been totally remodeled with an open floor plan, fenced yard, new bathrooms and kitchen, new engineered wood floors, new tile in kitchen an...

Photo of Listing #A4474860

Under Construction. Custom New Construction home West of the Trail in McClellan Park! This 3,267 SF custom home will be completed by end of 2020 and will be constructed with energy efficient u...

Photo of Listing #A4472783

This totally renovated home is located in the sought-after Granada area close to downtown Sarasota. The light-filled floor plan creates an uplifting vibe, with 2,292 sq. ft. of living space from wh...

Photo of Listing #A4474738

An updated cottage located on Siesta Drive, the gateway to the beach. This incredible location is in close proximity to dining, boutique shops, and area venues, and Morton's Gourmet Market. Siesta ...

Photo of Listing #A4474714

Imagine yourself living in this meticulously maintained West of Trail residence, set in the coveted and ideally located area of Sarasota that is close to the bay, beaches, shopping, medical and ret...

Photo of Listing #A4473643

This fabulous West of Trail location is on a quiet private street. The value is in the land, nestled among newer neighboring and gracious traditional residences. Enjoy close proximity to shopping, ...

Photo of Listing #U8092152

Come be awed by this 1939 Ralph Twitchell custom built ranch home in McClellan Park! This 2510 sq/ft home sits nested among large shade trees and mature landscaping that encompasses nearly 1/2 acre...

Photo of Listing #A4473596

West of Trail rare opportunity to own an updated Circa 1926 Spanish Mission home in the desirable Poinsettia Park neighborhood across from Cherokee Park. This enchanting four bedroom and four bath...

Photo of Listing #A4474640

Located West of the Trail, near downtown Sarasota and very close to Sarasota Memorial Hospital, this amazing home was originally built in 1926 and occupies 1.5 lots so it has ample room for a pool,...

Photo of Listing #A4474166

Everybody wants new and everybody seems to be buying boats in order to stay local and have a social distanced pastime of jumping in a boat cruising Sarasota’s gorgeous waters. Here is an opportunit...

Photo of Listing #A4474600

Located in a cherished West of Trail location with A+ schools, this like-new Allegra Homes “The Alexander” original has been expertly improved with loads of new features to enhance its great bones ...

Photo of Listing #A4473738

BEAUTIFUL HOME WEST OF TRAIL FOR UNDER $900,000!!! One of a kind 1925 Spanish Mediterranean home in the highly sought after west of trail location. Walk to Southside Village, Shelby Gardens or...

Photo of Listing #A4474193

Location, Location, Location! This custom built John Cannon home is ideally located in Sarasota's "West of the Trail" neighborhood, just a few blocks from Southside Village, Sarasota Memorial Hosp...

Photo of Listing #A4473622

This gorgeous 5 bedrooms, 4.5 bath home located in the most sought out area of Sarasota, West of the Trail is now on the market! The home encompasses over 3,500 square feet of living space that ha...

Photo of Listing #A4473757

Future homesite for your new home in McClellan Park, 15,100 Sq foot lot, just over 1/3 acre, tucked away and located on a quiet street just across from Sarasota Bay. This is one of Sarasota's fines...

Photo of Listing #A4473454

Hurry, these residences will go FAST! There are currently ONLY FOUR BOAT SLIPS presently available for sale in the community! Inquire for more details today! Taylor Morrison, America's Most Trusted...

Photo of Listing #A4473456

Hurry, these residences will go FAST! There are currently ONLY FOUR BOAT SLIPS presently available for sale in the community! Inquire for more details today! Taylor Morrison, America's Most Trusted...

Photo of Listing #A4473305

Enjoy a downtown Sarasota location in a resort style community offering an active Florida lifestyle. Popular Fiji model with 2nd floor entry, totally renovated and offered turnkey furnished. First ...

Photo of Listing #A4473370


Photo of Listing #A4473175

Historical cottage loaded with charm and remodeled in the last few years. Entering the home you are greeted with hardwood floors, high beamed ceilings and an amazing stone fireplace. Looking out t...

Photo of Listing #A4472690

NEWLY UPDATED DOWNTOWN SARASOTA CONDO in the sought after Resort-Style Community of CENTRAL PARK II on Hudson Bayou off Sarasota Bay! This Lovely 2 Bed/2.5 Bath End Unit allows for brighter inter...

Photo of Listing #A4473206

AMAZING LOCATION & GREAT VALUE IN HISTORIC MCCLELLAN PARK - WEST OF TRAIL! JUST REDUCED $15K! Just steps to Southside Village with a delightful array of restaurants, boutiques and Morton's Gourmet...

Photo of Listing #W7824898

Located West of Trail in Oyster Bay area of Sarasota sits this updated spacious 5 Bedroom 5 bathroom 2 story home built in 2103! The home has undergone extensive upgrades inside and out, including ...

Photo of Listing #A4471079

One or more photo(s) has been virtually staged. Sitting atop one of Sarasota's most coveted neighborhoods showcases a stunning contemporary home, oozing with style and artistic sophistication. Comp...

Photo of Listing #A4472154

Rarely available 2BR/2.5 BA Turn-key Furnished townhouse totally renovated kitchen has beautiful Australian granite counters with cherry wood cabinets with pull-outs, undercabinet lighting, wine ra...

Photo of Listing #A4469973

Located in Central Park I on Hudson Bayou this 2-bedroom, 2-bath unit has been renovated from top to bottom. The peaceful 6 acre parklike setting is enjoyed by owners who find the location ideal fo...

Photo of Listing #A4472086

Location! Spacious Sarasota family home in West of Trail and West of Osprey Southside district. Situated on 1/3 of an acre in Hudson Bayou neighborhood, just a half-mile to Southside Village and Sa...

Photo of Listing #A4471322

Location, Location, Location! This is it! You must see this beautiful home!! This 3 bedrooms, 2 bath home shows wonderfully. Upgrades include: Open floor plan, new kitchen, new flooring, new applia...

Photo of Listing #A4473445

Hurry, these residences will go FAST! There are currently ONLY FOUR BOAT SLIPS presently available for sale in the community! Inquire for more details today! Taylor Morrison, America's Most Trusted...

Photo of Listing #A4473452

Hurry, these residences will go FAST! There are currently ONLY FOUR BOAT SLIPS presently available for sale in the community! Inquire for more details today. Taylor Morrison, America's Most Trusted...

Photo of Listing #A4470657

This lovely treehouse is located in a gated, waterfront community, west of the trail (US 41) known as The Landings. These cool, multi-leveled homes have been designed to be part of the natural envi...

Photo of Listing #O5860070

This spacious home in Sarasota offers 5 bedrooms, 3.5 baths and features include great room with fireplace and built ins, large kitchen with lots of cabinets, and pool with lanai. A lot of work is ...

Photo of Listing #A4470005

Traditional Florida charm abounds from this lovely Harbor Acres home, overlooking deep sailboat waters that flow out to Sarasota Bay and nestled among lush greenery.

Photo of Listing #A4469793

Welcome to the Landings Carriagehouse II, a collection of villas surrounded by majestic trees and mature landscaping and a centrally located community pool. This 3 bed 2 bath home was renovated to...

Photo of Listing #A4471239

Prime west of trail location in Oyster Bay Estates near the Field Club. Spacious and private 5 BR/3BA heated pool family ranch home (or buildable lot on over a third of an acre). This home has an ...

Photo of Listing #A4473451

Hurry, these residences will go FAST! There are currently ONLY FOUR BOAT SLIPS presently available for sale in the community! Inquire for more details today! Taylor Morrison, America's Most Trusted...

Photo of Listing #A4473453

Hurry, these residences will go FAST! There are currently ONLY FOUR BOAT SLIPS presently available for sale on a separate agreement! Inquire for more details today! Taylor Morrison, America's Most ...

Photo of Listing #A4470440


Photo of Listing #A4468457

Wonderful location in high demand area west of the trail. Move right in to your sprawling ranch style home or remove current home and build custom on this extremely large lot. Lot can also be split...

Photo of Listing #A4470156

Rare opportunity to restore or build on this oversized walled lot adjacent to Hudson Bayou. all within walking distance to downtown and Sarasota Bay. Value is in the land. The home is an added b...

Photo of Listing #A4468814

This breathtaking 5 bedroom, 3.5 bath home is finally for sale. This home features two oversized master suites, one on each floor. The downstairs master includes an en-suite office/media area. The ...

Photo of Listing #A4469068

A car collector’s paradise located West of the Trail in Prestigious Cherokee Park! This fashionable 1936 Art Deco home contains a 10 car air conditioned garage with 2 lifts (allowing storage for 12...

Photo of Listing #A4468636

Under Construction. Designed by one of Sarasota’s most prominent architects, Clifford Scholz of CMSA, and constructed by the award-winning custom home builder, Dynan Construction, this new West Ind...

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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 August 12th, 2020 at 7:45pm EDT.