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 $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: 77
Average Price: $1,864,643
Highest Price: $10,800,000
Lowest Price: $219,000

Real Estate For Sale West of Trail Sarasota

77 Properties Found. Page 1 of 2.
Photo of Listing #A4515689

One or more photo(s) has been virtually staged. Wonderful close to everything community, one block to Marie Selby Gardens, 2 blocks to the bay front and downtown. This is a rare opportunity to own ...

Photo of Listing #A4515429

Completely furnished fifth floor 2 bedroom, 2 bath plus den 5th floor, 1,706 sq.ft. condo with 180 degree water views. This home features a newer air conditioner, impact resistant windows and doors...

Photo of Listing #A4513436

Bright and beautifully updated unit in the mid-rises of Eagles Point in the Landings. This 2 bedroom plus den first floor unit provides westward views across the mangroves. Enjoy the evening sunset...

Photo of Listing #A4514901

Located in a quaint community by Kimlira Estates, this newly-updated 5-bed, 5-bath custom-built house by Thomas V Hensey is a symbol of abundant craftsmanship. Resting on a ½ acre plot, this 5,800+...

Photo of Listing #A4513480

Expansive space inside and out with over-the-top potential in highly sought-after West of Trail neighborhood. This grand Mediterranean-style home blends unique old-world features with a modern desi...

Photo of Listing #A4515327

Welcome to your lovely private sanctuary in Sarasota. Savor downtown Sarasota living while taking advantage of an amazing waterfront property and boating lifestyle on the Hudson Bayou in proximity ...

Photo of Listing #A4515095

Everything you ever wanted in a very lovely and affordable downtown condo. This unit is being sold turnkey furnished. There are built ins in the master bedroom and a murphy bed in the guest bedroom...

Photo of Listing #A4515150

Coastal Contemporary at its best located West of the Trail. Newly built in 2019 by Tivoli on a 13,700 SF lot, this one floor living residence features 3 bedrooms + office/den, 3 full baths, 3-car ...

Photo of Listing #A4515035

SIMPLY STUNNING in Sought After Southside!....Ultimate Indoor/Outdoor Living combined with Grandeur of Bright Expansive Spaces in this Single Floor Contemporary. You will be WOWED upon walking thru...

Photo of Listing #O5979839

One or more photo(s) has been virtually staged. This Sarasota one-story home offers a patio, and a one-car garage.

Photo of Listing #A4514778

West of Trail lakefront home with end-of-cul-de-sac privacy in Oyster Bay Estates. An exquisite expression of midcentury modern infused with a spirit of positivity and delight. Completely renovated...

Photo of Listing #A4513424

This isn't just a condo, this is a lifestyle. In the epicenter of Sarasota, you can walk or ride your bike to downtown, the bayfront and the Legacy Trail. You simply cannot live this close to dow...

Photo of Listing #T3329633

LUXURY LISTING ALERT!! Welcome to this 3-bedroom, 3-full bath pool home. This forever home was fully renovated in 2019/2020, the owners spared no expense…. It is a true "rare" find! This home is li...

Photo of Listing #A4514435

This charming residence at 1231 South Orange Avenue was built with a craftsman style in the 1950s and was completely updated in the 1990s to include another level for the owner's retreat. The 2,319...

Photo of Listing #A4513813

Natural elements and design expertise merge to create this “Coastal Contemporary” residence West of the Trail, ideally situated between Orange and Osprey Avenues. Built in 2018 by Voigt Brothers Co...

Photo of Listing #A4514461

Pre-Construction. To be built. Prime Building opportunity West of the Trail. Location and Luxury meet on this Coastal Contemporary home design in the exclusive Oyster Bay area. This 4 bedroom ( co...

Photo of Listing #A4514239

One or more photo(s) has been virtually staged. Under Construction. Prime West of the Trail, custom-built, new construction currently under construction. Welcome to The Colina on Orange, a picture-...

Photo of Listing #A4514185

One or more photo(s) has been virtually staged. Amid a canopied oasis, resort-like bliss awaits you on Sarasota Bay, surrounded by magnificent works of nature. Constructed in 2008, the exquisitely ...

Photo of Listing #A4514275

Simple Elegance Surrounded by Nature. Luminous and elegant, wonderfully private and nestled on half an acre, this 4 bedroom home is a shining example of Florida living in The Landings community. Sp...

Photo of Listing #A4513920

updated end unit 2 storey condo with fireplace. Large master bedroom 2 lanais, Great well managed condo association.

Photo of Listing #A4513707

Stunning, spacious, airy, light-filled, wood-beamed contemporary house solidly constructed by notable neighborhood builder for his personal family! This lovely home is lushly landscaped with more g...

Photo of Listing #A4513057

One or more photo(s) has been virtually staged. Under Construction. Prime West of the Trail, custom-built, new construction, coastal contemporary, modern home by M&J Pham Homes. Spanning 3,478 squa...

Photo of Listing #A4492222

OPPORTUNITIES are VERY LIMITED! Taylor Morrison, America's Most Trusted Builder for (5) years running, is now offering the final few BRAND NEW LUXURY TOWNHOMES for sale in Philippi Landings! Did I ...

Photo of Listing #A4512951

The best value in one of the best neighborhoods in SRQ!!! Priced competitively this three bedroom two bathroom ranch style home with a beautiful den/office and well sized backyard is perfect for th...

Photo of Listing #A4512989

Bring your boat and live downtown. West of the trail waterfront condo on the Hudson Bayou with quick access to the beautiful Sarasota Bay and Gulf waters. Two residences have been combined into one...

Photo of Listing #A4512995

Located in one of Sarasota’s most prominent neighborhoods, property is has a postcard-like setting which features wide-open bay views on approximated 3/4 of an acre of land. Positioned only 3 lots ...

Photo of Listing #A4507122

The Landings-a gate community west of the trail. This custom 2 story home is perfect for your family. Plenty of living space on the main floor including an expansive master suite and den. Upstairs ...

Photo of Listing #A4512638

There just isn’t a better neighborhood to have a new home! Exceptional opportunity to build on this .4 ac vacant lot located almost at the end of Ladue Lane just south of the prestigious Field Club...

Photo of Listing #A4512881

Under Construction. Stunning custom contemporary home in the exclusive West of Trail neighborhood "Westbrook". This desirable Oyster Bay area home is very close to Siesta Key and downtown without t...

Photo of Listing #A4512916

Cherokee Park Perfection! Set on an idyllic lot in one of Sarasota's most sought after neighborhoods, you will find this meticulously maintained custom home. The location is ideal, with quick acce...

Photo of Listing #A4510295

Rarely available- a Landings property with a lake view and a 3 car garage. Check this out before its gone- 3 bedrooms, 2.5 baths- open plan family home. Spacious rooms, a southern exposure with l...

Photo of Listing #A4493296

Under Construction. MLS#A4493296 ~ Built by Taylor Morrison ~ December Completion! The Endeavor floor plan is 1,825 square feet with 3 bedrooms, 3 baths, study & a 2-car tandem garage. This three s...

Photo of Listing #A4512661

It is no secret, the three rules of real estate are location, location and location and this home satisfies all three. DO NOT miss out on this West of Trail, Granada cottage in Sarasota. Offering a...

Photo of Listing #A4512138

Stunningly designed to soak in the water views and surrounding oak canopies, this upscale condominium in Riggs Landing fuses sophisticated tastes with a casual coastal flair. Brimming with style an...

Photo of Listing #A4508851

Build Your Dream Home!! Two legal residential building lots are waiting for you to create the perfect paradise! Convenient to downtown Sarasota, I-75 interstate, shopping stores, restaurants, enter...

Photo of Listing #A4511310

Seller to be Reviewing all Offers on Tuesday 10/26/2021 at 5PM. This is a HOT Property located in one of the Best Cul-de-Sac Streets West of the Trail in the Historic District of McClellan Park! Th...

Photo of Listing #A4512234

This Custom Designed Contemporary Home is Located "West of the Trail" in one of the most sought after areas in Sarasota. Within one block of Southside Village & Sarasota Memorial Hospital, a Short ...

Photo of Listing #A4511962

Welcome to a secure and active lifestyle with tranquil views in this three-bedroom, four-bath plus den condominium situated in Eagles Point at The Landings, one of Sarasota’s most beautifully lands...

Photo of Listing #A4511854

Now is the time! This is the place! The perfect investment property, seasonal or full-time residence. “West of the Trail”, just east of the “North Siesta Bridge”. This two bedroom, one and a half...

Photo of Listing #T3328079

Centrally located in the WEST OF THE TRAIL neighborhood of GRANADA, only a 2 minute bike ride over the bridge to SIESTA KEY, & situated on an OVERSIZED HOMESITE, this IMPECCABLY CARED for 3 bedroom...

Photo of Listing #A4509309

WATER VIEWS FROM THIS BUILDER’S PENTHOUSE PLAN WITH LARGEST TERRACE IN THE BUILDING! This lovely 4 bedroom, 3 bath residence is a private treasure nestled in one of Sarasota’s best kept secrets in...

Photo of Listing #A4511252

If it's a serene, stylish and updated retreat you're looking for, you've found it at Eagles Point in The Landings. This end-unit condominium with an open floor plan has two bedrooms, a den (that co...

Photo of Listing #A4510936

This is the best value on a lot in Sarasota West of Trail. Close to Downtown, Sarasota Memorial Hospital, shops/restaurants, A+ Schools and the famed Siesta Key Beach. Walk to restaurants, Trader J...

Photo of Listing #A4492221

Under Construction. ***CURRENT PHOTOS are of the on-site model & do not include furniture or depict the same exterior or interior finishes, colors, or landscape."*** ONLY THREE LEFT!! Taylor Morris...

Photo of Listing #A4492220

***CURRENT PHOTOS are of the on-site model & do not include furniture or depict the same exterior or interior finishes, colors, or landscape."*** ONLY THREE LEFT!! Taylor Morrison, America's Most T...

Photo of Listing #A4510517

One or more photo(s) has been virtually staged. Under Construction. Prime West of the Trail, Custom-Built, New-Construction Coastal Contemporary Modern Home by "M&J Pham Homes." Located in highly-e...

Photo of Listing #A4492226

Under Construction. ***CURRENT PHOTOS are of the on-site model & do not include furniture or depict the same exterior or interior finishes, colors, or landscape."*** ONLY THREE LEFT!! Taylor Morris...

Photo of Listing #A4492223

Under Construction. ***CURRENT PHOTOS are of the on-site model & do not include furniture or depict the same exterior or interior finishes, colors, or landscape."*** ONLY THREE LEFT!! Taylor Morris...

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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



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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 25th, 2021 at 1:07pm EDT.