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: 131
Average Price: $1,574,161
Highest Price: $18,000,000
Lowest Price: $205,000

Real Estate For Sale West of Trail Sarasota

131 Properties Found. Page 1 of 3.
Photo of Listing #A4496995

Here is an OPPORTUNITY to purchase one of the last original waterfront homes in Harbor Acres. This property is being offered for land value only. There is a very nice 4 bedroom, 4 1/2 bathroom 350...

Photo of Listing #A4497079

Modern spacious ranch home in The Landings- over 3,000 square feet under air with 4 bedrooms and 3.5 baths including a 2 car side-entry garage with tons of built in storage. Lush mature landscaping...

Photo of Listing #A4497139

Grab this one and make it your own, before the 2nd stage renovation begins. Located in one of Sarasota's most desired areas, "West of the Trail" at The Landings, this terrific corner lot pool home ...

Photo of Listing #A4497115

Stunning opportunity in coveted Landings Carriagehouse 1. Beautifully updated and move in ready, this residence expresses a sense of style and effortless luxury. Beautiful wood floors flow througho...

Photo of Listing #A4496683

MULTIPLE OFFER Situation. Seller asks for highest and best by 6:00pm Thursday 4/8/2021. Fabulous opportunity in the coveted historic Granada neighborhood. Centrally located, west of the trail and ...

Photo of Listing #A4496872

Prime location! Dreaming of living in downtown Sarasota? This adorable condominium is a short distance from the beautiful waters and oversized art sculptures that line the Sarasota bayfront. Only o...

Photo of Listing #A4497005

Rarely available first floor lakeview condo! Turnkey furnished! This lovely one bedroom condo features an open floor plan, wood floors and crown molding throughout, workable kitchen with butcher b...

Photo of Listing #A4495372

Come live in this beautifully constructed contemporary home in very desirable Oyster Bay neighborhood just down the street from the historic Field Club on Sarasota Bay and a quick bike ride to the ...

Photo of Listing #A4494816

West of the Trail, like a new house…maybe better! A substantial addition in 2017 plus major renovations to the existing structure drastically transformed this West of the Trail cottage into the 21s...

Photo of Listing #A4491592

Unique opportunity to own a property in the highly sought-after neighborhood of Harbor Acres! This mediterranean home is nested on an oversized lot surrounded by distinctive mature trees and plants...

Photo of Listing #A4496672

If tennis is your game, then look no further. This rarely available lake-view condominium at Eagles Point Circle in the gated community of The Landings located on US 41/Proctor Road is just 15 minu...

Photo of Listing #A4488268

Coach House in the highly sought-after community of The Landings. As you come up the stairs you find yourself in the bright and spacious great room with vaulted ceilings and natural light in this d...

Photo of Listing #A4495130

Oyster Bay Landings one of the rarest neighborhoods in Sarasota. Waterfront, gated, private, on the mainland west of the trail, close to everything, and the Field Club is a short walk away. This ...

Photo of Listing #A4495958

Welcome to the gated community of the Landings and the Landings Racquet Club in Sarasota. This two bedroom, two bath one story Carriage House has had a complete make over and now shows like a model...

Photo of Listing #A4496441

Central Park 11 condominiums is one of Sarasota best value in the downtown area. this 2 bedroom 2.5 bath is rented at rate of $1350.00 per month till August 31,2021. Spacious 2BD 2.5BA Condo - 2-st...

Photo of Listing #A4494895

BRAND NEW RENOVATED Euro Chic Condo, right in the heart of downtown! Modern Swedish touches, with upgraded crown molding, butcher block countertops, pantry, upgraded lights, fixtures, doors and tri...

Photo of Listing #A4493680

Located West of Trail and nestled among an abundance of tropical foliage in the historic neighborhood of Granada, this 2008 built two-story home offers all the modern conveniences of a newer reside...

Photo of Listing #A4495936

Pre-Construction. To be built. This expansive lakefront custom home is situated on an estate sized home site in Sarasota's coveted West of Trail area. Through a striking Entry Courtyard, Owners are...

Photo of Listing #A4495861

Great opportunity in Landings Carriagehouse 1. The ease of condo living with the space and feel of a house. With views of the pond and fountain this unit is waiting for the right buyer to make it t...

Photo of Listing #A4492454

Rarely available free standing Landings Treehouse. This light filled two-story, three-bedroom residence provides space and comfort. New travertine floors flow throughout the lower level. A portion...

Photo of Listing #A4494527

Looking for new place to call home....this coastal modern residence really has it all. Situated in Sarasota's most coveted waterfront community Harbor Acres. Estate size parcels, pristine water, u...

Photo of Listing #A4495557

In exquisite condition and boasting illustrious quality of design and finishes, this newer Allegra-built home in Granada is a superb example of southern coastal opulence. A classic front porch and ...

Photo of Listing #A4495342

Welcome to this lovely two bedroom, two bath, with den Landings Carriagehouse- a true delight in a peaceful green setting. Wood flooring flows throughout, the galley kitchen with white wood cabinet...

Photo of Listing #A4495615

“West of Trail” farmhouse chic residence located within steps to SouthSide Village, Selby Gardens, Cherokee Park, restaurants and shopping. Spacious 5-bedroom, 4.5 bath home includes recent upgrade...

Photo of Listing #A4495252

If you are ready to enjoy all the cultural amenities that Sarasota has to offer, then this is the LOCATION for you! Enjoy the beautiful view from the EXTENDED balcony in this highly desirable 2 bed...

Photo of Listing #A4495165

Rare HEART OF WEST OF THE TRAIL opportunity! One of the LARGEST parcels in the coveted GRANADA PARK! Measuring in at 175ft in length and 106ft deep this expansive lot boasts over 18,550 SQ FEET. Ev...

Photo of Listing #A4495204

Live amongst lush canopy and bright greenery in your very own Landings Treehouse. This 3-bedroom, 2 1/2-bath residence fuses sophistication with outdoor living, bringing nature into your elegant ho...

Photo of Listing #A4495598

Its like finding a diamond in paradise! This 1st floor condo and amazing location cannot be beat. Garden Plaza is a little known condo community West of the Trail, tucked away in a canopy of oaks a...

Photo of Listing #A4495325

This is one of the most eclectic beachy homes on the market now. On a rare freshwater spring-fed pond filled with wildlife, you’ll enjoy over 3,000 square feet of living space with 4 bedrooms, 3.5 ...

Photo of Listing #A4491607

This Oyster Bay home sits in an idyllic quiet cul-de-sac of the highly sought after Oyster Bay Estates community, which sits just west of Tamiami Trail and mere blocks south of Siesta Key Drive. T...

Photo of Listing #A4494963

Southern exposure! This beautifully maintained West of the Trail home is in ideal, move-in ready condition. Set among lush, manicured foliage on more than a quarter-acre of property, with its gorge...

Photo of Listing #A4495214

Location, convenience, sophistication, privacy- all of these are yours in this artfully renovated and reimagined three bedroom, three bathroom condominium located in downtown Sarasota. Completely r...

Photo of Listing #A4495306

Pre-Construction. To be built. Best value in Sarasota West of Trail. Granada Park homes blend traditional coastal architecture with the latest building innovations, green standards and smart home t...

Photo of Listing #A4495314

Pre-Construction. To be built. Best value in Sarasota West of Trail. Granada Park homes blend traditional coastal architecture with the latest building innovations, green standards and smart home t...

Photo of Listing #A4495317

Pre-Construction. To be built. Best value in Sarasota West of Trail. Granada Park homes blend traditional coastal architecture with the latest building innovations, green standards and smart home t...

Photo of Listing #A4495132

Oyster Bay Landings one of the rarest neighborhoods in Sarasota. Waterfront, gated, private, on the mainland west of the trail, close to everything, and the Field Club is a short walk away. Direc...

Photo of Listing #A4494771

You've found it, This Pot of Gold is yours to behold. Be one lucky enough to see this before it goes! This Jewel on the Bay has been completely remodeled in 2020. Open airy light and bright this pr...

Photo of Listing #A4494907

Welcome to the Landings. Live on one of the most beautiful streets in the highly sought-after Landings Treehouse Condominium community. Imagine your new home nestled amongst a tropical paradise and...

Photo of Listing #A4494803

Prime location west of the trail in the Southside school district with Southside Village near by for shopping and dining. Lovely custom built pool home only minutes to downtown and the world famous...

Photo of Listing #A4492829

Location, Location, Location! Gorgeous condo in this highly desirable west of the trail location! This two-bedroom, two-bath condo is immaculate! Upgraded kitchen and bathrooms with granite counte...

Photo of Listing #A4493673

This is the one- only 3 bed, 2 bath coach house listed for sale in The Landings- fully renovated with a lake view. An easy move in, nothing to do but relax. Enjoy the spacious open feeling – consis...

Photo of Listing #A4494732

Another dazzling display of award-winning design and construction to be built by the notable custom homebuilding team at Allegra Homes. Presenting the 2021 “Kristi Ann” model with an exciting array...

Photo of Listing #A4491250

Don't miss out on this amazing opportunity to own 50% of the interest of this property! Located near all of the best restaurants, shopping and entertainment, and the world-famous Siesta Key Beach. ...

Photo of Listing #A4494431

Enjoy the beautiful water views from this bright and spacious condominium in the premier Eagles Point Circle at The Landings. This 3rd floor condo with just under 2000 square feet with 2 bedrooms p...

Photo of Listing #A4494289

Enjoy this entertainers home! This 2-story charming home has gorgeous travertine flooring throughout common areas of dining/living/kitchen with the master suite on the main level accessing the heat...

Photo of Listing #A4493085

Pre-Construction. To be built. Another dazzling display of award-winning design and construction to be built by the notable custom homebuilding team at Allegra Homes. This contemporary Oyster Bay b...

Photo of Listing #A4494345

Under Construction. Currently under construction. Estimated completion fall of 2021. Perkins Powers Builders is pleased to unveil another custom contemporary home in one of Sarasota's most disting...

Photo of Listing #A4494479

Under Construction. Custom New Construction home West of the Trail in McClellan Park that will be walking distance to A rated Southside School, close to great shops and restaurants in Southside Vil...

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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
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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 April 11th, 2021 at 12:31am EDT.