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: 168
Average Price: $1,134,713
Highest Price: $4,399,000
Lowest Price: $220,000

Real Estate For Sale West of Trail Sarasota

168 Properties Found. Page 1 of 4.
Photo of Listing #A4482078

Welcome to Central Park II, fashionable condominiums located on Hudson Bayou, in downtown Sarasota; this 2BR/2B condo has been completely renovated with a new kitchen, tile flooring throughout, new...

Photo of Listing #A4481664

Valuable waterfront in coveted Harbor Acres on a protected deep boat basin with expansive water and nature views. Existing home is for free that be used as a rental while you design your future d...

Photo of Listing #A4481386

WEST OF THE TRAIL on a beautifully Tree Lined Street looking toward Granada Fountain is this 2bed/1 bathroom home with a 1bedroom/1 bathroom Guest house. You can either renovate or build new. It re...

Photo of Listing #A4481549

WEST OF THE TRAIL on a beautifully Tree Lined Street looking toward Granada Fountain is this 2bed/1 bathroom home with a 1bedroom/1 bathroom Guest house. You can either renovate or build new. It re...

Photo of Listing #A4481899

Income producing property located just minutes to Siesta Key and Downtown Sarasota! Two 1 Bedroom, 1 Bath units. With New updates like updated kitchen, New stainless steel appliance package, update...

Photo of Listing #A4481408

A stunning one-of-a-kind modern home west of the trail, on a quiet cul-de-sac street, in the heart of Sarasota. Highly sought-after courtyard entry brings privacy and sleek design to this Susan H...

Photo of Listing #A4481050

It is all about location and Southern comfort with this craftsman style home, located west of the trail in the Pointsetta Park neighborhood. The house sits behind a historic Banyon tree which capt...

Photo of Listing #A4481752

Priced to move fast! This 5 bedroom, 3.5 bath pool home is centrally located near Sarasota Memorial Hospital, Siesta Key beaches and all that Sarasota has to offer, all within the sought after West...

Photo of Listing #A4481101


Photo of Listing #A4481516

Remarkable value in this charming West of Trail, two-bedroom, one-bath, single-family home. Enjoy south Osprey living just steps from Sarasota Memorial Hospital and Southside Village shops and rest...

Photo of Listing #T3271791

Bring your tool belt and your imagination and make this house a charmer. Excellent lot location. Main house has 2 bedrooms and 2 baths with one 3/4 bath off the back enclosed porch. Back house has ...

Photo of Listing #A4474738

An updated cottage located on Siesta Drive, the gateway to the beach. This incredible location is in close proximity to dining, boutique shops, and area venues, and Morton's Gourmet Market. Siesta ...

Photo of Listing #A4481033

PRIME SOUTHSIDE VILLAGE 1922 BUNGALOW on oversized lot (78x146). Walk to the end of the street and you are at Southside Village restaurants and stores and then 1 more block to Sarasota Memorial Hos...

Photo of Listing #A4474852

Your private garden home in charming and convenient Cherokee Park, situated on a 30,000 square foot lot. This traditional West of Trail home sits under a canopy of grand Oaks with sparkling Sarasot...

Photo of Listing #A4476950

Sarasota Historically Registered Masterpiece, West of the Trail, 3 blocks walk from Markets, Shopping, Restaurants and Bars. This exquisite home has been remodeled from head to toe with New Roof, N...

Photo of Listing #A4480890

Excellent rental opportunity centrally located in sunny Sarasota and just minutes to Siesta Key Beach! This concrete block duplex has two, 2 bedroom/1 bath units. Each unit has its own private, fen...

Photo of Listing #A4478348

Location, Luxury, Security, Serenity, Spaciousness and the list goes on and on! Rarely available is this coveted 4 bedroom + 4 bathroom center unit which lives like a single family home. Once you...

Photo of Listing #A4480860

Soaring ceilings, skylights and a deck off every room bring Florida’s natural landscape indoors and it is why this cedar-sided residence is called a TREEHOUSE. WEST OF THE TRAIL, behind the gates o...

Photo of Listing #A4480894

Welcome Home! This bungalow has an incredible location with the best of what Sarasota has to offer at your finger tips. Located across from the brand new Sarasota Art Museum and walking distance to...

Photo of Listing #A4481303

This turn-key home was completely remodeled in 2017, and it’s perfectly situated in the Bayview neighborhood, west of Tamiami Trail. This fantastic 3 bedroom, 2 bath home is surrounded by lush natu...

Photo of Listing #A4480691

3-BEDROOM CORNER UNIT 6th-floor residence with southern facing views of gorgeous PHILLIPPI CREEK! Loads of natural light enhance the truly Florida view. When you leave town, simply close the planta...

Photo of Listing #A4480796

Under Construction. To be built. Location and Luxury meet on this Coastal Contemporary home in the Oyster Bay area. This 4 bedroom 4.5 bath home being constructed by The Holliday Group sits on a...

Photo of Listing #A4480659

Location, Location, Location! Looking for your own piece of paradise? Look no further! This first floor, turnkey furnished, 1 bedroom 1 bath condo in Central Park II is nestled between coveted down...

Photo of Listing #A4481213


Photo of Listing #A4481299

West of the Trail!! This residence offers a great opportunity to invest in a home that is 5 minutes to Siesta Key Beach and 1 minutes to Sarasota Bay. The prime location is amidst multi-million-dol...

Photo of Listing #U8100711

One or more photo(s) has been virtually staged. Terrific fifth floor penthouse condo with downtown views in rarely available Central Park condominiums. Living room has floor-to-ceiling bay windows ...

Photo of Listing #A4480901

Beautifully blending security with a warm and inviting openness, this gorgeous custom home is ideal for appreciating an elegantly casual way of life in the heart of Sarasota. Surrounded by mature t...

Photo of Listing #A4479770

West of the Trail waterfront community in one of the most desirable locations – Downtown Sarasota. Hudson Landings is offering this 3 bedroom, 2 bath condominium featuring an open and bright floor ...

Photo of Listing #A4480476

You will be WOWED! by this West of the Trail 2016 Custom Built (4) Bedroom TURNKEY FURNISHED Pool Home located in One of Sarasota's Great Residential Neighborhoods---walking distance to Southside: ...

Photo of Listing #A4478869

This charming 1947 Bungalow, on a large lot (9,940 sq. ft.) is everything you would expect in the historical West of Trail neighborhood of Southside Village. Inviting brick front porch, restored pi...

Photo of Listing #A4480387

Private charm in a dream location. This single-story home in the highly sought-after West of Trail area is the perfect combination of ease and access. Located in a gated community just minutes from...

Photo of Listing #A4480802

Downtown Sarasota, Sarasota Bay and Marina Jacks at your doorstep. Surround yourself with lush landscaping, Banyan trees and the beautiful Hudson Bayou. Enjoy your water view from one of three balc...

Photo of Listing #A4478724

A rare opportunity in the desirable 5450 building of the Eagles Point community in The Landings, this two-bedroom plus den with preserve and water views delights with picturesque beauty indoors and...

Photo of Listing #A4477033

A unique oasis just outside of downtown Sarasota, this two-bedroom bungalow in the premier West of Trail community of Desota Park is delightfully historic with modern conveniences. Framed by mature...

Photo of Listing #A4480317

Under Construction. New Construction.Situated on a beautifully landscaped parcel in the desirable Oyster Bay area, this brand-new home grants casual grandeur and the exquisite Florida way of life. ...

Photo of Listing #A4479968

Phillippi Landings is a private waterfront community surrounded with 10 acres of tropical landscaping and magnificent oak trees. With a gated entrance, this waterfront condominium provides terrific...

Photo of Listing #A4479312

This is a wonderful opportunity to purchase in the coveted neighborhood of Avondale, a close knit community featuring many neighborhood social gatherings and clubs, situated in one of the most desi...

Photo of Listing #A4479955

This unique TREEHOUSE is a single unattached unit in the Treehouse section of the Landings situated next to the nature path that leads to the Intercoastal waterway and a gazebo for viewing and fish...

Photo of Listing #A4479030

Known for being one of Sarasota’s most desirable addresses, the waterfront homes in Harbor Acres are unique in their architecture and graceful in their design, and this stunning five-bedroom estate...

Photo of Listing #A4479173

Originally named "La Casa Benedetta,” this west of the trail custom home is what you have been looking for! Tastefully designed and built with the highest quality, this double lot, Tuscan inspired ...

Photo of Listing #A4479454

Cross the private bridge into your gated 10-acres of waterfront paradise. This 2 bedroom plus den, 2 bathroom condo is tucked back in the community and offers relaxing and private views from the 13...

Photo of Listing #A4479802

Hudson Landings, along Sarasota’s Scenic Hudson Bayou. On the water, a downtown residential boutique condominium/townhouse, a corner unit on the first level. A must see. A charming cluster of only ...

Photo of Listing #A4473738

BEAUTIFUL HOME WEST OF TRAIL FOR UNDER $900,000!!! Back on market after being temporarily removed to put on a BRAND NEW ROOF and NO INCREASE in asking price!!! One of a kind 1925 Spanish Med...

Photo of Listing #A4479735

This tranquil & tropical dream home is situated in the idyllic neighborhood of Granada, West of Trail off of Siesta Drive (north bridge to Siesta Key). This custom built Key West & Martha’s Vineyar...

Photo of Listing #A4478204

Welcome to the Landings and your new home. Light & bright downstairs two bedroom end unit coach house located on the lake. Enjoy the privacy of split bedrooms and the glass enclosed lanai. This w...

Photo of Listing #A4479128

The home rests on over a third of an acre in the most sought-after neighborhood in Sarasota, Cherokee Park. Originally built in 1949, this residence was recently redesigned inside and out and broug...

Photo of Listing #A4477754

Cherokee Park charm meets modern day convenience in this beautiful home on Selby Garden-like grounds. Practically perfection - live in one of the most desirable neighborhoods in Sarasota – close to...

Photo of Listing #A4479185

Location. Location. Location. Enjoy a ‘west of the trail’ lifestyle in this adorable ranch style home. With a 2/2 main house and a 1/1 detached in-law cottage, this property has it all. A screened-...

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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
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.

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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 28th, 2020 at 4:30am EDT.