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: 81
Average Price: $1,866,040
Highest Price: $18,000,000
Lowest Price: $215,000

Real Estate For Sale West of Trail Sarasota

81 Properties Found. Page 1 of 2.
Photo of Listing #A4507011

**Please See Virtual Tours** Located West of Trail, Plaza Gardens is located just around the corner from the North Bridge and just minutes from Siesta Key Beach. You’ll be walking distance to the...

Photo of Listing #A4503815

Charming home nestled in the sought after West of Trail community, one block North of Southside Elementary School. The original house was built in 1989, but the current owner did an addition in 200...

Photo of Listing #A4506711

Carl Abbott’s office designed this spectacular New Modern residence in the historic neighborhood of Avondale. Intelligent design features and a gracious open floorplan are complemented by discernin...

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 #A4507005

Rare opportunity to create a private new estate on a spacious 15,000 sf lot located in the premier enclave of Harbor Acres, one of Sarasota's most desirable West of Trail neighborhoods and in the t...

Photo of Listing #A4507521

Rare opportunity to create a private new estate on a spacious 15,000 sf lot located in the premier enclave of Harbor Acres, one of Sarasota's most desirable West of Trail neighborhoods and in the t...

Photo of Listing #A4502684

This idyllic retreat in one of the few gated communities West of Trail offers potential immediate revenue opportunity through August 2022, with the potential to continue renting or as a serene pers...

Photo of Listing #A4506338

West of Trail/McClellan Park elegant 4200+ sq ft 3 car garage John Cannon home has an open floor plan with a formal living room, fireplace and spacious dining room. The family room with 20' ceiling...

Photo of Listing #A4507243

Premier West of Trail location in the coveted Oyster Bay Estates neighborhood just a few houses from the historic Field Club. Lushly landscaped 4 bedroom/3.5 bath bright and airy home offers plenty...

Photo of Listing #A4506366

Highest & best due by noon Mon July 12th. Seize your opportunity to own this beautifully updated townhome-style condo. Highly desirable "West of Trail" location. This premium unit overlooks a park-...

Photo of Listing #A4505921

Your home and your office all in one. This two bedroom, two bath home has two additional rooms that have multi-purpose potential. This property provides convenient access to the heart of Sarasota ...

Photo of Listing #A4506612

Located in a cherished West of Trail location with A+ schools, this like-new home is sure to delight! Enveloped in a lush setting of Florida-friendly landscape is a 3168 sq. ft. 2-story home featur...

Photo of Listing #A4505661

This unit is freshly painted, clean and ready for you to move right in and enjoy everything Sarasota has to offer! Entertain in the open concept kitchen/living area with plenty of counter space for...

Photo of Listing #A4506770

Built in 2017 by award-winning builder Allegra Homes and designed for comfortable livability in gorgeous surroundings, the inviting and well-lit 2,855 square foot “St. John” floor plan has been exp...

Photo of Listing #A4499673

Sold during processing

Photo of Listing #T3315754

Gorgeous, Beautiful & Immaculate are just a few of the words that describe this “Arlington Park” Trend setting GEM! This professionally remodeled 2 Bed 2 Bath 2 + Carport home has so many feature...

Photo of Listing #A4505729

Highly sought and rarely available Penthouse condo with unobstructed western exposure to Siesta Key and the Intracoastal Waterway. Enjoy watching fabulous sunsets from your screened balcony and sea...

Photo of Listing #A4505182

Recently remodeled high end contemporary ground floor condo in a 24 Hour Guarded and gated community! Amazing water views. Move in ready. Designed with the outdoor enthusiast in mind. 8 Har Tru ...

Photo of Listing #A4504373

Backups offers encouraged. The Oyster Bay neighborhood of Eastbrook is a lovely enclave of 42 homes off Camino Real. It is conveniently located between the two Siesta Key bridges, close to The Fiel...

Photo of Listing #A4504682

This home, located on Siesta Drive is just a two-minute walk to the North Bridge Outlook Park overlooking the Intracoastal Waterway in Sarasota's beautiful bay. This is the lowest priced home west ...

Photo of Listing #A4504071

This beautifully updated and well-maintained colonial style home perfectly complements the sought-after, historic neighborhood of McClellan Park. Set among lush greenery, on an oversized corner par...

Photo of Listing #A4504408

This highly desirable location in Bay View Heights, nestled between Harbor Acres and Cherokee Park is perched high above the street and offers a perfect location to call home. Privacy abounds in th...

Photo of Listing #N6116026

Exceptional opportunity to build in the Exclusive Gated community of Oyster Bay Landings with only 14 homesites. This lot 13,000+ sq ft includes a DEEDED DOCK SLIP with direct access to the Intraco...

Photo of Listing #A4501556

Sold Data Only

Photo of Listing #A4501731

This custom luxury residence rests within the sought-after Oyster Bay area, West of Trail. Heritage Builders completed this West Indies-inspired home in May of 2019, featuring four bedrooms and bat...

Photo of Listing #A4504024

HOTTEST LISTING WEST OF THE TRAIL! HGTV watch out, here is your newest competition. This beautiful 2 bedroom 2 bathroom was built in 1925 and has been fully remodeled from the top to the bottom! N...

Photo of Listing #A4503846

Modern Sarasota residence in highly-desirable West of Trail location — walk to Southside Village and only one mile to downtown Sarasota. Come home to an in-town oasis filled with natural light, ope...

Photo of Listing #A4503467

West of Trail buildable lot! You will not want to miss this opportunity, location is awesome, walkability to shopping, dining, Post Office, even Siesta Key Beach is only a walk/bike ride away, yet...

Photo of Listing #A4503506

Located in one of Sarasota's most desirable neighborhoods West of Trail, sits this charming, completely renovated cottage. The quaint home is brilliantly set in a quest and serene framed by oaks, t...

Photo of Listing #A4502662

WOW, Looking for space, all on one level and just over a 1/2 acre with pool? And no steps in the house. A beautiful find in The Landings, one of the prettiest and one of the few gated in-town subdi...

Photo of Listing #A4503692

Looking for affordable DOWNTOWN LIVING in a beautifully maintained West of Trail community? Look no further! Neat, clean and move-in ready, this highly desirable townhome style condo, located in ...

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 #A4502627

Pre-Construction. To be built. You’ll love coming home to this gorgeous brand new 3-bedroom, 3-bath “Hibiscus” model with 2-1/2 side load garage and being built by award-winning Allegra Homes for a...

Photo of Listing #A4500563

2 separate buildings! Short term rentals permitted! SO MUCH potential here! Renovated 2 bedroom 1 bathroom cottage with hardwood floors and separate 1 bedroom 1 bath block home which features terra...

Photo of Listing #A4502702

Located in historic Cherokee Park, this 11,700 sq. ft. lot can be subdivided. It is not in flood zone yet a stone’s throw to Siesta Key and Southside Village with Morton’s Gourmet Market, restauran...

Photo of Listing #N6115705

One or more photo(s) has been virtually staged. SUMMER PRICE! Exceptional and Unique Custom Contemporary West Indies Courtyard style residence built in 2016 (Never Lived-In) with luxury, quality an...

Photo of Listing #A4501817

The opportunity to live West of the Trail for under a million awaits you and Seller can accommodate a quick closing to allow enrollment in Southside Elementary asap! Move in Ready, renovated charme...

Photo of Listing #A4500086

This elegant West of the Trail estate home with large homesite is located on one of the most attractive flower streets. Walking distance to Southside Elementary, blocks to Southside Village with Mo...

Photo of Listing #A4501943

Pre-Construction. To be built. Pre-Construction. To be built. Secure your dream home now before prices go up again. This is the best value in Sarasota West of Trail with an SRQ Builders custom home...

Photo of Listing #T3308842

This is your clean Canvas in an amazing neighborhood secluded in a Tropical Paradise. In The Landings Treehouses you can enjoy a peaceful setting surrounded by lush vegetation and live oaks. This t...

Photo of Listing #A4501172

Welcome to this stunning West of the trail property, that sits on a double lot in prime area. A+ school district and close to Siesta key Beach, south side village and downtown. Hardwood floors thro...

Photo of Listing #A4500630

One or more photo(s) has been virtually staged. Under Construction. Introducing the Coastal Craftsman Rejuvenation at Southside Village. Constructed by the award-winning custom home builder, Dynan ...

Photo of Listing #A4499341

LOCATION, LOCATION, LOCATION. Great professional office for sale with high visibility directly on Tamiami Trail (US 41) JUST 1 mile south of Sarasota Memorial Hospital . Currently medical offic...

Photo of Listing #A4500544

Pre-Construction. To be built. Heritage Builders proudly unveils their newest luxury custom home, the Windley. This lakefront estate is situated in Sarasota's highly sought after West of Trail neig...

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 #A4499907

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 #A4499842

One of the LARGEST parcels in the coveted GRANADA PARK is now available! Measuring in at 175ft in length and 106ft deep this expansive LOT boasts over 18,550 SQ FEET. Even more impressive, this lot...

Photo of Listing #A4498960

SARASOTA ~ "WEST OF TRAIL" ~ CITY OF SARASOTA ~ SOUTHSIDE VILLAGE ~ SOUTHSIDE SCHOOL, if you have been waiting for the right "West of Trail" opportunity to enjoy, this property just might be the an...

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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 July 23rd, 2021 at 11:54am EDT.