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: 80
Average Price: $1,942,133
Highest Price: $18,000,000
Lowest Price: $219,900

Real Estate For Sale West of Trail Sarasota

80 Properties Found. Page 1 of 2.
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 #A4511800

Turnkey furnished in a lushly landscaped mid-rise condo complex on Hudson Bayou. The unit was remodeled in 2015 with added features that include light bamboo floors throughout; a beautiful kitchen ...

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 #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 #A4512137

West of trail beauty! This 5 bedroom, 4 & 1/2 bathroom custom home is located on a quiet, dead end street and close to everything. The second floor bonus room can be used as a playroom, game room, ...

Photo of Listing #A4512054

TRIPLEX: 2/2, 1/1 & 1/1…! Great Income producing property with a proven track record. Adjacent lot next-door also for sale with a separate sale. Lots of antique features..must see to appreciate. B...

Photo of Listing #A4512056

TRIPLEX: 4/2, 1/1 & studio…! Stunning Income producing property with a proven track record. Live in one unit and rent out the others. Currently utilized as “4” short term rentals. New roof added in...

Photo of Listing #A4511039

This inviting 2-bedroom, 2-bath + Den/3 bedroom jewel is the perfect Sarasota pied-à-terre with a wonderful West of Trail location just blocks from the north Siesta Key bridge. The 1,302 square fe...

Photo of Listing #A4511954

Largest floorplan available in the mid-rises at Eagles Point in the Landings. With almost 3,000 sq ft this tastefully updated, elegant unit lives like a home. Enter into the foyer through a private...

Photo of Listing #A4511310

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! This 1954 Blue Heron Drive Home is Perfect as a Remodel Opportunit...

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 #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 #A4511619

West of the Trail, TURNKEY FURNISHED, Beautifully REMODELED 2 bedroom 1 bath plus extra double vanity condominium, located just minutes from world-renowned Siesta Key Beach. Two parks within walkin...

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 prime WEST OF THE TRAIL neighborhood of GRANADA, just minutes from SIESTA KEY & situated on an OVERSIZED HOMESITE, this IMPECCABLY CARED for 3 bedroom, 2 bath rustic bungal...

Photo of Listing #A4511445

TRIPLEX: 4/2, 1/1 & studio…! Great Income producing property with a proven track record. Live in one unit and rent out the others. Currently utilized as “4” short term rentals. Property has Recentl...

Photo of Listing #A4511446

TRIPLEX: 2/2, 1/1 & 1/1…! Long-term tenants are already in place so earn right away. Great Income producing property with a proven track record. Purchase an adjacent lot next-door and earn six figu...

Photo of Listing #A4511216

Welcome to sought after Eagles Point in THE LANDINGS !! This great 3 Bedroom 2 1/2 bathroom beauty has breathtaking views of the Intracoastal Waterway from every window. It is so spectacular. This ...

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 #A4509599

Come and see this beautiful Spanish Mediterranean style four-bedroom, three & a half bath home! This "West of Trail" stunner has 2-story ceilings, mature landscaping, and is ready to move in! Locat...

Photo of Listing #A4510893

This is the One! *"West of The Trail" between Osprey Avenue and Tamiami Trail* Large 10,403 sf lot*3bed/2bath tri level home*Living room features a beamed cathedral ceiling*Just a few minutes to Sa...

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 #A4509923

Quality Location, OYSTER BAY, quality builder: TODD JOHNSON, oversized 17K sq ft corner lot with quality finishes create a 3400+ sq ft and total 4893 sq ft QUALITY LIFESTYLE. Built in 2014, this...

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 #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 #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 #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 #A4510334

Right from the pages of Traditional Home, this Cape Cod charmer is set on a beautifully treed lot on one of the most architecturally diverse and popular streets in the Osprey to Orange corridor. Ta...

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 #A4508638

Welcome home to this 2018, 4 bedroom + office/den + bonus room, 3 bath coastal contemporary luxury pool home, built by the award-winning premier builder, Allegra Homes and located West of Trail and...

Photo of Listing #A4509418

Under Construction. Brand new West of the trail construction.....Don’t miss out on your opportunity to own a rare New West of the Trail Modern Beauty. Canvas Sarasota represents your opportunity to...

Photo of Listing #A4509443

Under Construction. Brand New west of the trail construction.....Don’t miss out on your opportunity to own a rare New West of the Trail Modern Beauty. Canvas Sarasota represents your opportunity to...

Photo of Listing #A4509677

Rarely available Carriage House in Tha Landings! Come see this beautiful 2 bedroom, 2 bath 1770 sq. ft. home. This gorgeous unit features light hardwood flooring throughout, crown molding, a wood-b...

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 #U8132486

Beautiful 2003 Spanish Mediterranean in a fabulous location! New tropical landscaping sets the tone as you approach this 3,160 square foot all-block home and park under your oversized porte cochèr...

Photo of Listing #A4508858

Pre-Construction. To be built. Waterfront located in Cherokee Park! Spectacular 5+ bedroom coastal style single family home complete with guest wing. Features include: gourmet kitchen with sub-zero...

Photo of Listing #A4509472

Inviting Sarasota West-of-Trail home in highly-desirable Paradise Shores — walk to Southside Village and only one mile to Sarasota Memorial Hospital and downtown Sarasota. Filled with natural light...

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 #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 #A4508450

Pre-Construction. To be built. Consistent with the residential creations by award-winning master builder Allegra Homes, this absolutely stunning 2-story “St. Joseph III” is no exception with its so...

Photo of Listing #A4508647

Located West of Trail, this 1053 sq ft, first floor, 2 bedroom 2 bath corner unit is located just around the corner from the North Bridge and just minutes from Siesta Key Beach. You’ll be walking ...

Photo of Listing #A4508637

Mediterranean masterpiece with attention to every detail is located on a quiet street west of the Trail surrounded by executive caliber estates. The current owners worked with John King with Ramp...

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...

Photo of Listing #A4492225

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 #A4508192

Pre-Construction. To be built. Under construction. Introducing this bespoke custom home in McClellan Park. This brand-new residence will be timeless and functional, and its West of Trail location s...

Photo of Listing #A4508035

This is an unrivalled opportunity to build your private estate with 100' waterfront and open views to Sarasota Bay. Enjoy 1 acre of lush, tropical waterfront in one of Sarasota's most enviable loc...

Photo of Listing #A4506894

One or more photo(s) has been virtually staged. Located in the heart of one of the most sought-after “West of Trail” neighborhoods in Sarasota, Cherokee Park, this timeless residence is set on a pi...

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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.

 

Communities

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

 

Lifestyles

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

5
, Resident
Pros:

Simply, the best area of Sarasota. Convenient, not stuck out on the barrier islands. Great families. Great diversity in houses. Great schools.

Cons:

Expensive for what you get.

Summary:

Love it here. No plans of leaving. I try to get all of my friends to move here.


5
, Resident
Pros:

Super convenient to everything in Sarasota. A great diversity in homes - from tear downs to waterfront mansions. School district

Cons:

Highly sought after = Expensive

Summary:

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 September 19th, 2021 at 10:19am EDT.