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: 192
Average Price: $1,186,084
Highest Price: $6,495,000
Lowest Price: $210,000

Real Estate For Sale West of Trail Sarasota

192 Properties Found. Page 1 of 4.
Photo of Listing #A4467470

Originally built in 1941, the home and guest home were substantially remodeled in 2012 to incorporate the best of old and new. Located on a quiet street and large corner lot in historic McClellan P...

Photo of Listing #A4466279

An idyllic single-family residence located on a serene lot in the gated Landings community complete with mature trees & lush landscaping, this beautiful 3 bedroom, 2.5 bath, 2,722 sf home is move-i...

Photo of Listing #A4467671

Red Rock walled estate just off Roberts Bay. County has confirmed 2 buildable lots each just over 20,000 square feet. Build your dream home here in the shade of majestic oaks. Prime real estate at...

Photo of Listing #A4467262

Nestled in a Selby-like setting and across the street from estate sized Bayfront properties sits this tucked away "architectural jewel". Large windows throughout allow the mature and varied landsca...

Photo of Listing #A4459896

A Sarasota gem that is rarely available. This boutique British Colonial style condominium residence is located on Hudson Bayou with deep sailboat water access and deeded boat docks for each unit. E...

Photo of Listing #A4467073

This is the one- best 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 – consi...

Photo of Listing #A4466863

Wonderful mid-century modern in one of the best neighborhoods Sarasota has to offer. Harbor Acres is perfectly situated just a few blocks to Southside Village and minutes to downtown Sarasota, SMH...

Photo of Listing #A4461053

Stunning, one-of-a-kind home in Sarasota's most sought after neighborhood: West of the Trail! Only six years old, this Mediterranean-style beauty is complete and move-in ready. The front yard's sto...

Photo of Listing #O5860070

This spacious home in Sarasota offers 5 bedrooms, 3.5 baths and features include great room with fireplace and built ins, large kitchen with lots of cabinets, and pool with lanai. A lot of work is ...

Photo of Listing #G5028870

INVESTMENT PROPERTY Located in the cute historic Granada neighborhood, 5-minute walking distance from ocean water and the Bay. Granada is located in the heart of Sarasota and Siesta Key. This upsca...

Photo of Listing #A4466267

This unique and contemporary custom home built in 2019 has 3-bedroom, 3.5 bath, office, bonus room that can be a 4th bedroom with closets. This showcase home is located in one of the most sought-...

Photo of Listing #A4466616

The Landings - West of the Trail - Gated Community - Embracing the spirit of Americana, the home is tucked away on a quiet cul-de-sac with a sweeping lawn and mature trees leading to the front entr...

Photo of Listing #A4465755

TURNKEY FURNISHED DOWNTOWN SARASOTA CONDO! This well maintained 2 bedroom condo with 2 1/2 baths will exceed your expectations. Both bedrooms are master suites and share a balcony that overlooks ...

Photo of Listing #A4466249

Celebrate gracious Sarasota living in coveted Avondale, one of Sarasota’s most distinguished West of the Trail neighborhoods, only moments from downtown Sarasota, Southside Village and Siesta Key b...

Photo of Listing #A4466099

Experience this enchanting 3-bedroom 3.5 bath with home office in idyllic Cherokee park. This home is both beautiful and charming and is complete with impressive updates which include a brand-new a...

Photo of Listing #A4466001

A winning combination – Waterfront. Welcoming. West of Trail. Live a luxe Florida lifestyle in this maintenance free, 4th floor, 2 bed 2 bath +den upscale condo - with its own boat slip! Lush, tro...

Photo of Listing #A4466075

Fabulous buy for a beautifully renovated pool home in popular West of Trail. Great condo alternative. Lots of natural light, new kitchen including cabinets and appliances with an open floor plan to...

Photo of Listing #A4464087

Prime West of Trail single family home (buildable lot) located in the Oyster Bay Estates subdivision. Lot dimensions are 100' x 150' (.34 acre) Major renovation required to update this 1959 3BR/2BA...

Photo of Listing #A4464107

Prime West of Trail single family home (buildable lot) located in the Oyster Bay Estates subdivision. Lot dimensions are 100' x 150' (.34 acre) Major renovation required to update this 1959 3BR/2BA...

Photo of Listing #A4465763

Rarely available Almeria Condominium. Located West of Trail and close to the gateway of one of the worlds best beaches, Siesta Key. You don't have to be a millionaire to live like one in this soug...

Photo of Listing #A4465425

NOW VACANT! Imagine living the Downtown Sarasota lifestyle without all the chaos of assigned/limited parking and high fees (cable, water, and pest control included - wow!); now imagine living the C...

Photo of Listing #A4465542

Tastefully updated ground floor Coachhouse in the Landings. Step into a bright and inviting home accentuated by sleek, clean lines. High end wood-look vinyl floors flow throughout the unit, giving ...

Photo of Listing #A4465552

Welcome to your new home! Central Park II is the best of both worlds: You're adjacent to downtown and the bayfront, without the big prices. Resort living: Tennis court, pool, hot tub, work-out ro...

Photo of Listing #A4463688

Idyllic neighborhood living in a cul-de-sac community West of the Trail. This Westbrook home is ready for the next family to make it their own for decades to come. The property is over one-half an...

Photo of Listing #A4465378

Location,location,location. Enjoy privacy from this two bedroom two bath end unit coach house. Updated eat kitchen with granite counter tops. Kitchen looks out onto the deck with private and par...

Photo of Listing #A4462623

Beautiful, true mid-century modern in desirable San Remo Estates! Sought after classic modern architecture with open floor plan, clean lines, vaulted ceilings and pristine colorful terrazzo that's...

Photo of Listing #A4461829

Lake view home West of Trail with Split plan and 3 large ensuite bedrooms. Kitchen and all three baths have been remodeled with granite, all cabinets and drawers are soft close. Stainless steel app...

Photo of Listing #A4464923

3D AND HIGHLIGHT VIDEO ATTACHED. VIRTUAL TOURS AVAILABLE. Enviably situated in one of the most coveted areas of Sarasota, this newly built West of the Trail home blends high quality design with sup...

Photo of Listing #A4464775

This Landings Treehouse gem has been lovingly upgraded and reimagined with extensive expansions and thoughtful customizations throughout. Many special features make it perhaps the best equipped, at...

Photo of Listing #A4465115

The Landings is an established, gated community centrally located to downtown and Siesta Beach and is sought after by all ages! Totally updated, this 3 bedroom 2 bath coach home is move in ready. ...

Photo of Listing #A4463411

Situated on a cul-de-sac tucked behind majestic live oaks, this enchanting custom residence blends gracious charm with everyday elegance. The sprawling courtyard home is reminiscent of the Cape Cod...

Photo of Listing #A4462202

The West of Trail modern family home you’ve been waiting for! Move-in ready, better than new, 2 blocks to Southside Elementary and oh so close to everything downtown and the beaches. Live the Sar...

Photo of Listing #A4459927

**Price Just Reduced **The Lowest Priced Single Family Home West Of The Trail on the "Flowers Streets"! This adorable 2 bedroom 2 bathroom home with a 1 car garage is located on the same street as...

Photo of Listing #A4456186

Tucked away in charming neighborhood and yet so close to all amenities. Quality Custom built and very private Home in amazing West of the Trail location. Close to great schools, Siesta Key and Down...

Photo of Listing #A4464103

Home is vacant. Welcome to the only West of the Trail GATED COMMUNITY of Mandarin Park. This home is a few minutes' walk to Sarasota Memorial Hospital and is near to shops, Sarasota High School, ar...

Photo of Listing #T3227302

This Luxurious Bungalow Hill single story home with high ceilings, travertine stone floors and high-end finishes is in sought after west of the trail neighborhood. Light and cheery with large windo...

Photo of Listing #A4462512

This villa has a beautiful water view looking straight down the lake with a fountain. The Landings Carriage house villa is nestled among trees with a park like setting. This villa has 2 split bedro...

Photo of Listing #A4462875

Experience The Sarasota Castle. Nestled just moments from one of the most vibrant and artistic cities in the USA, Sarasota, this incredibly unique property seamlessly blends tradition, craftsmans...

Photo of Listing #A4463139

Inviting and comfortable ground floor Coachhouse in the coveted Landings community. Sold Turnkey furnished, this home is the perfect winter escape. Warm wood floors flow throughout the unit. The up...

Photo of Listing #A4463927

This second story 3 bedroom, 2 bath Landings Coach house has the water view you have been waiting for. A north west exposure overlooking a lake with fountain. Volume ceilings in the combo living/...

Photo of Listing #A4463832

Solar-Powered Zen 3BR/2 Full Baths/2 Half Baths + Den, Pool home with Massive Bonus 26'x28' air-conditioned space behind the two-car garage for your home-based business, possible In-Law Suite, car ...

Photo of Listing #A4461409

Virtual Showing available, please, contact me and I’ll send you the video.Investors or remodeling Alert! Nestled in the historic McClellan Park district, West of the trail, this property is located...

Photo of Listing #A4463211

An enchanting hideaway in desirable McClellan Park, this 5-bedroom plus den home surprises and delights with rare architecture, character-filled spaces and sweeping acreage. Stone walls enclose the...

Photo of Listing #A4463421

An enchanting hideaway in desirable McClellan Park, CURRENTLY with a 5-bedroom plus den home with surprising ARCHITECTURE & sweeping acreage. Stone walls enclose the over 1-acre property, revealing...

Photo of Listing #A4461944

LOCATION, LOCATION, LOCATION! Prime 11,360 lot with existing traditional, block construction bungalow featuring two bedrooms, one bath located in the affluent West of the Trail Neighborhood. There ...

Photo of Listing #O5852288

Stunning 2/1 traditional home with detached 1/1 back cottage! Rare! Peaceful neighborhood, yet only 4 minutes to Siesta Key & downtown. Home is all quality — finished by a Mennonite master craftsma...

Photo of Listing #A4463334

West of the Trail! Exceptional opportunity for a like new, furnished, award winning former Miah model home by Sarasota's best custom builder, John Cannon Homes. This spacious custom pool home is r...

Photo of Listing #A4460277

West of Trail. Location, Location, Location. Steps from Hillview and Osprey shops and restaurants. Close to the hospital. Southside School district. Charming Mediterranean Bungalow with impecc...

Search All Real Estate Listings in: Sarasota
See TODAY's New Listings, search by beds/baths, home & lot size, listing status, days on market & more!

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.

Your Rating *

How Do You Know?

Live/Lived Here Just Visited

About You

*Your email address will not be displayed

Your Review

Search Homes For Sale in West of Trail

Back to all Sarasota Real Estate


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 May 25th, 2020 at 11:00pm EDT.