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: 129
Average Price: $1,608,454
Highest Price: $18,000,000
Lowest Price: $225,000

Real Estate For Sale West of Trail Sarasota

129 Properties Found. Page 1 of 3.
Photo of Listing #A4496924

Pre-Construction. To be built. Pre-Construction available now in McClellan Park! Wind your way down the tree-lined streets of one of Sarasota's most historic neighborhoods, McClellan Park, and find...

Photo of Listing #A4498380

INVESTOR ALERT! Here is the chance to choose your builder and build your dream home West of the Trail. Magnolia Street is one of the most desirable "Flower" streets because of its convenient locati...

Photo of Listing #A4498297

Elegant and inviting home in the highly sought after community of The Landings. Imagine entertaining or enjoying family life in this light filled home boasting high ceilings and architectural detai...

Photo of Listing #A4498041

Here is your opportunity to live the downtown lifestyle in a NEW RENOVATED condo that is ready to move into. Unit 207 was created and designed by Lancaster Designs. Quality built by Willis Smith, C...

Photo of Listing #A4497565

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

Photo of Listing #A4498214


Photo of Listing #A4498259

Under Construction. Under Construction. *Model Home tour Available at 2222 Pine Terrace, Sarasota Wednesday through Sunday 12:00pm - 4:00pm.* Brand new Majestik Home. 1698 Arlington Street brings m...

Photo of Listing #A4498107

McClellan Park, with its parklike setting, became a fashionable neighborhood in the 1920s when many of the residences were built. It is even more attractive today, with its proximity to downtown Sa...

Photo of Listing #A4498137

You will not want to wait on this incredible opportunity to own in West of Trail's prestigious Harbor Acres! Live in the home as-is, or just for a time while you plan to build your dream house on ...

Photo of Listing #A4498135

You will not want to wait on this incredible opportunity to own in West of Trail's prestigious Harbor Acres! Live in the home as-is, or just for a time while you plan to build your dream house on t...

Photo of Listing #R4904801

The Avondale neighborhood situated West of the Trail, is one of the most desirable locations in beautiful Sarasota, FL. This property is ideally located in the middle of Irving Street just east of...

Photo of Listing #A4497656

**JUST 1 Block north of Sarasota Memorial Hospital** This renovated, medical / office building features a beautifully designed Lobby, Waiting Room, 6 Exam Rooms, 2 Treatment/Procedure Rooms, 5 Off...

Photo of Listing #A4497190

Totally renovated with chic finishes and the ultimate in style, this carriage house in the coveted Carriage House 1, community of the Landings is an oasis for easy living both indoors and out. Cof...

Photo of Listing #A4497689

Welcome to Harbor Acres, one of the most prized addresses in Sarasota, and home to this magnificent residence of style and sophistication. The contemporary style of this home perfectly blends inter...

Photo of Listing #O5936852

Centrally located West of the Trail in the rarely-available Red Rock Park area this move-in ready home sits on an oversized lot with plenty of outdoor space with its covered lanai, expansive custom...

Photo of Listing #A4496927

Nestled under the canopy of mature trees, you will appreciate this home’s ability to embrace family and friends. Charming and quaint, yet updated with stylish formal living and dining rooms that pr...

Photo of Listing #A4497079

Modern spacious ranch home in The Landings- over 3,000 square feet under air with 4 bedrooms and 3.5 baths including a 2 car side-entry garage with tons of built in storage. Lush mature landscaping...

Photo of Listing #A4495130

Oyster Bay Landings one of the rarest neighborhoods in Sarasota. Waterfront, gated, private, on the mainland west of the trail, close to everything, and the Field Club is a short walk away. This ...

Photo of Listing #A4497139

Finally, your Search is Over! Welcome home to one of Sarasota's most desired areas, "West of the Trail" at The Landings. This spacious corner lot pool home boasts 4 large bedrooms and 2.5 baths. Th...

Photo of Listing #A4496995

Here is an OPPORTUNITY to purchase one of the last original waterfront homes in Harbor Acres. This property is being offered for land value only. There is a very nice 4 bedroom, 4 1/2 bathroom 350...

Photo of Listing #A4497115

Stunning opportunity in coveted Landings Carriagehouse 1. Beautifully updated and move in ready, this residence expresses a sense of style and effortless luxury. Beautiful wood floors flow througho...

Photo of Listing #A4496672

If tennis is your game, then look no further. This rarely available lake-view condominium at Eagles Point Circle in the gated community of The Landings located on US 41/Proctor Road is just 15 minu...

Photo of Listing #A4496683

MULTIPLE OFFER Situation. Seller asks for highest and best by 6:00pm Thursday 4/8/2021. Fabulous opportunity in the coveted historic Granada neighborhood. Centrally located, west of the trail and ...

Photo of Listing #A4496872

Prime location! Dreaming of living in downtown Sarasota? This adorable condominium is a short distance from the beautiful waters and oversized art sculptures that line the Sarasota bayfront. Only o...

Photo of Listing #A4495372

RECENT $76,000 PRICE REDUCTION: Come live in this beautifully constructed contemporary home in very desirable Oyster Bay neighborhood just down the street from the historic Field Club on Sarasota B...

Photo of Listing #A4494816

West of the Trail, like a new house…maybe better! A substantial addition in 2017 plus major renovations to the existing structure drastically transformed this West of the Trail cottage into the 21s...

Photo of Listing #A4488268

Coach House in the highly sought-after community of The Landings. As you come up the stairs you find yourself in the bright and spacious great room with vaulted ceilings and natural light in this d...

Photo of Listing #A4495958

Welcome to the gated community of the Landings and the Landings Racquet Club in Sarasota. This two bedroom, two bath one story Carriage House has had a complete make over and now shows like a model...

Photo of Listing #A4496441

Central Park 11 condominiums is one of Sarasota best value in the downtown area. this 2 bedroom 2.5 bath is rented at rate of $1350.00 per month till August 31,2021. Spacious 2BD 2.5BA Condo - 2-st...

Photo of Listing #A4494895

BRAND NEW RENOVATED Euro Chic Condo, right in the heart of downtown! Modern Swedish touches, with upgraded crown molding, butcher block countertops, pantry, upgraded lights, fixtures, doors and tri...

Photo of Listing #A4493680

Located West of Trail and nestled among an abundance of tropical foliage in the historic neighborhood of Granada, this 2008 built two-story home offers all the modern conveniences of a newer reside...

Photo of Listing #A4495936

Pre-Construction. To be built. This expansive lakefront custom home is situated on an estate sized home site in Sarasota's coveted West of Trail area. Through a striking Entry Courtyard, Owners are...

Photo of Listing #A4495861

Great opportunity in Landings Carriagehouse 1. The ease of condo living with the space and feel of a house. With views of the pond and fountain this unit is waiting for the right buyer to make it t...

Photo of Listing #A4494527

Looking for new place to call home....this coastal modern residence really has it all. Situated in Sarasota's most coveted waterfront community Harbor Acres. Estate size parcels, pristine water, u...

Photo of Listing #A4495557

In exquisite condition and boasting illustrious quality of design and finishes, this newer Allegra-built home in Granada is a superb example of southern coastal opulence. A classic front porch and ...

Photo of Listing #A4495342

Welcome to this lovely two bedroom, two bath, with den Landings Carriagehouse- a true delight in a peaceful green setting. Wood flooring flows throughout, the galley kitchen with white wood cabinet...

Photo of Listing #A4495615

“West of Trail” farmhouse chic residence located within steps to SouthSide Village, Selby Gardens, Cherokee Park, restaurants and shopping. Spacious 5-bedroom, 4.5 bath home includes recent upgrade...

Photo of Listing #A4495252

If you are ready to enjoy all the cultural amenities that Sarasota has to offer, then this is the LOCATION for you! Enjoy the beautiful view from the EXTENDED balcony in this highly desirable 2 bed...

Photo of Listing #A4495165

Rare HEART OF WEST OF THE TRAIL opportunity! One of the LARGEST parcels in the coveted GRANADA PARK! Measuring in at 175ft in length and 106ft deep this expansive lot boasts over 18,550 SQ FEET. Ev...

Photo of Listing #A4495214

Location, convenience, sophistication, privacy- all of these are yours in this artfully renovated and reimagined three bedroom, three bathroom condominium located in downtown Sarasota. Completely r...

Photo of Listing #A4495598

Its like finding a diamond in paradise! This 1st floor condo and amazing location cannot be beat. Garden Plaza is a little known condo community West of the Trail, tucked away in a canopy of oaks a...

Photo of Listing #A4495204

Live amongst lush canopy and bright greenery in your very own Landings Treehouse. This 3-bedroom, 2 1/2-bath residence fuses sophistication with outdoor living, bringing nature into your elegant ho...

Photo of Listing #A4495132

Oyster Bay Landings one of the rarest neighborhoods in Sarasota. Waterfront, gated, private, on the mainland west of the trail, close to everything, and the Field Club is a short walk away. Direc...

Photo of Listing #A4495325

On a rare freshwater spring-fed pond filled with wildlife, you’ll enjoy over 3,000 square feet of living space with 4 bedrooms, 3.5 baths, a wine room, a very private office, a large family room, a...

Photo of Listing #A4491607

This Oyster Bay home sits in an idyllic quiet cul-de-sac of the highly sought after Oyster Bay Estates community, which sits just west of Tamiami Trail and mere blocks south of Siesta Key Drive. T...

Photo of Listing #A4494963

Southern exposure! This beautifully maintained West of the Trail home is in ideal, move-in ready condition. Set among lush, manicured foliage on more than a quarter-acre of property, with its gorge...

Photo of Listing #A4495306

Pre-Construction. To be built. Best value in Sarasota West of Trail. Granada Park homes blend traditional coastal architecture with the latest building innovations, green standards and smart home t...

Photo of Listing #A4495314

Pre-Construction. To be built. Best value in Sarasota West of Trail. Granada Park homes blend traditional coastal architecture with the latest building innovations, green standards and smart home t...

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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 April 23rd, 2021 at 7:33am EDT.