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: 216
Average Price: $1,200,676
Highest Price: $7,500,000
Lowest Price: $214,900

Real Estate For Sale West of Trail Sarasota

216 Properties Found. Page 1 of 5.
Photo of Listing #A4448579

Relax into Florida waterfront living on this secret slice of paradise in the heart of the city. Down a private drive, nestled within the mature tropical landscaping sits this picturesque 4 bedroom ...

Photo of Listing #A4448328

A stunning reflection of West of the Trail luxury, this three-bedroom model home from Allegra blends coastal glamour with designer details and dreamy indoor/outdoor living. Having never before been...

Photo of Listing #O5818010

Beautiful custom built home in exclusive gate-guarded community, great location

Photo of Listing #A4443056

Enjoy a quaint hideaway tucked away in this pleasantly secluded neighborhood West of the Trail. Hidden from the road, this two bedroom, two bath (en suite) home is extremely private, but close to e...

Photo of Listing #A4448427

West of Trail. Green-certified. Parade of Homes winner. This inspiring British-West Indies-style residence features the best of luxury living. Designed with countless conversation starters and an i...

Photo of Listing #A4443001

Inside lake facing very clean ground floor end unit Monaco Model. 2 Beds 2 Baths Approximately 1032 sq.ft. including the screened in lanai. This condo has been very well maintained and shows imma...

Photo of Listing #A4447392

Beautiful home close to Siesta and Southside School. Move in condition, only 9 years old. Furniture is negotiable. If you like a home with unlimited special features, this is the home. Coffered...

Photo of Listing #A4448288

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 #A4447950

WEST of Trail - Nestled on a charming private street, this home is located in the desired Field Club and Oyster Bay area. Large Master Bedroom on the first floor with separate his/her closets. Mast...

Photo of Listing #A4447278

Situated in the heart of the Harbor Acres neighborhood, West of the Trail, this home is move-in ready. Completely remodeled in 2012, the open floor plan is filled with natural light. As you enter t...

Photo of Listing #A4444762

This beautiful, 2015-built, coastal contemporary five-bedroom + office home in exclusive Oyster Bay provides all the benefits of “new construction” without the delays, surprise costs and effort to ...

Photo of Listing #A4447026

The best of luxurious waterfront living at this stunning, newer Harbor Acres home! Perfectly positioned just a few lots in from the open bayfront, abounding in impeccable views of Sarasota Bay and ...

Photo of Listing #A4447949

This custom built home boasts a tremendous location and mature landscaping. Close proximity to Downtown Sarasota, Southside Village on Hillview, Marina Jack, and Sarasota Memorial Hospital. From m...

Photo of Listing #A4447378

Grand Yet Intimate. This Aspirational .58 Acre, 8100 Sq. Ft. Custom Built 5 Bedroom, 6 1/2 Bath Home Only Comes Along Once In A Lifetime. Perfect For The Fledgling Family, Multi-Generational Family...

Photo of Listing #A4444694

If you have been waiting for an updated coach house, your wait is over. A renovated ground floor 2 bedroom 2 bath condo with a private backyard overlooking a wooded preserve. Cherry hardwood floors...

Photo of Listing #A4447472

Great Location for this gorgeous fully remodel furnished condo in upscale waterfront gated community of Phillipi Landings. One of Sarasota's best kept secrets. Come and enjoy a luxurious lifestyle ...

Photo of Listing #A4447606

Situated West of Trail in the exclusive Oyster Bay area near the Field Club, this 2017 home by Heritage Builders blends British-West Indies style with superior finishes and thoughtful indoor/outdoo...

Photo of Listing #A4447947

West of Trail 3/3 with pool, hurricane windows and additional upgrades for under $1M!! This like new 3 bed, 3 bath home in one of the most desirable neighborhoods in Sarasota has the ideal floor pl...

Photo of Listing #A4444679

Are you looking for water views with incredible privacy? Look no further and get ready to fall in love with both. The four season glassed in lanai space opens to a private patio. Put your deck cha...

Photo of Listing #A4447302

Prime West of Trail buildable lot in sought-after Granada, one of Sarasota's highly desirable locations. Granada is a quiet, private, established neighborhood with easy access to all amenities — be...

Photo of Listing #A4445752

Set on nearly a half-acre corner lot in the coveted area of Oyster Bay, this one-level coastal home is inviting and open with 3,933 square feet of gorgeous indoor living. This custom designed 4-bed...

Photo of Listing #A4447118

Perfectly situated on the outskirts of Siesta Key sits this well-appointed, newly updated home with a metal roof, sequestered courtyard and worlds of entertaining space in one of Sarasota’s most so...

Photo of Listing #A4446808

Customized 4th floor, west-facing end unit lives like a home with abundant natural light. Cross the private bridge, pull into your enclosed garage & ride the elevator to your 3 bed, 2 bath oasis in...

Photo of Listing #A4446790

Sophisticated update of this 3 bedroom 2 ½ bath townhome with a 2 car attached garage that truly lives like a single family home, yet in a maintenance free lifestyle within the gated community of T...

Photo of Listing #A4446722

Pre-Construction. To be built. NEW custom home. Ready to start construction immediately. This 4100 sq. ft. coastal WATERFRONT home by Yoder Built Properties has it all! Great location west of The T...

Photo of Listing #A4446726


Photo of Listing #A4444610

Endless sunsets in a beautiful setting await the new owner of this wonderful Condo. Cross the private bridge into your gated 10-acres of waterfront paradise. This 2 bedroom plus den 2 bathroom con...

Photo of Listing #A4446250

West of Trail. Architect redesigned 5+ bedroom single family home with detached guest quarters. Main home amenities includes: beautiful crown mouldings, chair rails, framed window casings, custom ...

Photo of Listing #A4445980

Sarasota West of Trail in the Flower Streets close to schools, shopping, dining, Downtown Sarasota and Siesta Key Beach, Move-in ready, you’ll love the very private indoor-outdoor living areas and ...

Photo of Listing #A4445132

One or more photo(s) has been virtually staged. An embrace of minimalism with simplicity in form and design, complete REMODEL on this 2,820 sq foot West of Trail home located in a mature-treed set...

Photo of Listing #A4445854

Better come and take a look... this 3 bed condo (3rd bedroom is currently used as a den) has been renovated with a high degree of style and sophistication. Located on the first residence level of E...

Photo of Listing #A4445987

This home delights all senses. Nestled into an abundance of old Fla flora, this charming 3 bed 2 ½ bath home offers nearly 2300 sq ft of cozy, quiet, lush, luxurious living. Bathed in natural light...

Photo of Listing #A4445775

Property and business for sale for $785,000.00...Business is an Italian cafe. It is also available separately for $165,000.00. Business is in prime location in Sarasota. Sarasota Memorial Hospital ...

Photo of Listing #A4445678

Fall in love with the amazing view and relax, in this bright spacious corner unit, that has already been fully remodeled. Panoramic sunset views to the west over Siesta Key and southern views of Ph...

Photo of Listing #A4445874


Photo of Listing #A4445676

Seller has priced aggressively at LAND VALUE for immediate sale. Located in Oyster Bay, one of Sarasota’s most revered neighborhoods and close to the Field Club. Located on a quiet cul-de-sac stre...

Photo of Listing #A4445620

Great opportunity to build your dream home West of the Trail in the heart of Sarasota. Just minutes from the famous Florida beaches and Siesta Key. Short drive to Downtown Sarasota and walking dist...

Photo of Listing #A4445067

Yes, you can actually move-in to this beautifully updated ‘west of trail’ Treehouse in The Landings and not have to improve or replace anything! Nestled in a canopy of 100 year old oak trees, thi...

Photo of Listing #A4445644

Beautiful details reflect the impeccable care given to this charming, west-of-the-trail, mid-century pool home. The glamorous kitchen does not skimp on functionality, with a gas range, bar with win...

Photo of Listing #A4445085

This property is all about the oversize lot and buildable land value! The 17,550 sf fenced lot that measures 108' x 162'. There is a non-historically designated 1930's main house 2 bedroom and 1...

Photo of Listing #A4445086

This property is all about the oversize lot and buildable land value! The 17,552 sf fenced lot measures 108' x 162'. There is no historic designation on the 1930's main house 2 bedroom and 1 bath ...

Photo of Listing #A4442884

Entertainers Paradise. This charming, private tropical oasis has 4 bedrooms, 4 bathrooms. 2 Master bedrooms with walk in closets. It has a bright and open floor plan with hard wood floors and a sep...

Photo of Listing #A4443756

Seldom available, and a hidden Jem "West of the Trail", on a quiet loop around Eastbrook pond. Out-of-the-way Kentwood Estates is transitioning to new multi-million dollar homes. The value in this...

Photo of Listing #A4444434

Seldom available and a hidden gem "West of the Trail" and on the lake in Oyster Bay, one of the most sought out areas in Sarasota. The value of this property is in the land. The buyers wishing to c...

Photo of Listing #A4445171

West of Trail, Oyster Bay Estates, Spectacular Waterfront, Mature trees and landscaping, Riverview High School, The Field Club, and just minutes to Siesta Key, Publix, Sarasota Memorial Hospital, S...

Photo of Listing #A4445177

West of the Trail, Kentwood Estates, Waterfront, Riverview High School, Quiet neighborhood with new multi-million dollar homes being built, close to The Field Club, Publix, Restaurants, Siesta Key,...

Photo of Listing #N6106916

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. LOCATION...LOCATION...LOCATION...This Mid-Century Charm is the BEST priced Home West of the Trail and...

Photo of Listing #A4445100

Beautiful West of the Trail completely renovated Treehouse in The Landings. This spacious 3 bedroom, 2 1/2 bath home offers both living and family room, gourmet kitchen with custom cabinetry, stain...

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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 October 15th, 2019 at 9:45am EDT.