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Sarasota Real Estate - West of the Trail

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Featured West of the Trail Homes for Sale

1711 Kenilworth Street, Sarasota image
1711 Kenilworth Street, Sarasota $1,699,000

Welcome to 1711 Kenilworth Street, an exceptional opportunity to own a move-in-ready home in one of Sarasota’s most desirable West of the Trail neighborhoods. Located wit...

  • 4 Beds
  • 3 Baths
  • Kenilworth Estates SubDv.
  • 34231 Zip Code
1675 Landings Lane, Sarasota image
1675 Landings Lane, Sarasota $1,930,000

Virtually Staged. Tucked beneath a canopy of sweeping mature oaks in one of Sarasota's most coveted gated communities, this gracious two-story home strikes the perfect ba...

  • 5 Beds
  • 6 Baths
  • Landings SubDv.
  • 34231 Zip Code
7631 Cove Terrace, Sarasota image
7631 Cove Terrace, Sarasota $2,890,000

Imagine having your own private outdoor paradise designed for a relaxing life on the water. This custom designed Key West style residence in Southpointe Shores offers dee...

  • 4 Beds
  • 3 Baths
  • Southpointe Shores SubDv.
  • 34231 Zip Code
1440 Kimlira Lane, Sarasota image
1440 Kimlira Lane, Sarasota $7,350,000

Located on approximately 200 feet of open Bay frontage in one of Sarasota's most prestigious neighborhoods, this remarkable property enjoys a postcard-worthy setting on m...

  • 4 Beds
  • 4 Baths
  • 34231 Zip Code
1555 Eastbrook Drive, Sarasota image
1555 Eastbrook Drive, Sarasota $4,250,000

Modern architecture reaches an extraordinary new level at 1555 Eastbrook Drive, a newly completed 2025 estate offering nearly 4,000 square feet of sophisticated single-le...

  • 5 Beds
  • 6 Baths
  • Kentwood Estates SubDv.
  • 34231 Zip Code
1386 Tangier Way, Sarasota image
1386 Tangier Way, Sarasota $16,000,000

Pre-Construction. To be built. Situated in San Remo Estates, one of Sarasota's most exclusive waterfront communities, this upcoming new construction home, designed and bu...

  • 4 Beds
  • 6 Baths
  • San Remo Estates SubDv.
  • 34239 Zip Code
1827 Baywood Drive, Sarasota image
1827 Baywood Drive, Sarasota $1,925,000

ATTENTION BOATERS!! Waterfront dream home – move-in ready! Just a quick (429 yard) boat ride to the ICW - no bridges - a straight shot to the water. Head out to the newly...

  • 3 Beds
  • 2 Baths
  • Bay View Acres SubDv.
  • 34231 Zip Code
3727 Tangier Terrace, Sarasota image
3727 Tangier Terrace, Sarasota $2,490,000

Welcome to a rare opportunity to own a spacious residence in the highly sought-after San Remo Estates, one of Sarasota's most desirable West of the Trail neighborhoods, i...

  • 4 Beds
  • 3 Baths
  • San Remo SubDv.
  • 34239 Zip Code
3525 Iroquois Avenue, Sarasota image
3525 Iroquois Avenue, Sarasota $450,000

Experience the best of Sarasota living in the highly sought-after Indian Beach neighborhood, just minutes from Sarasota Bay, The Ringling Museum, Jungle Gardens and vibra...

  • 3 Beds
  • 2 Baths
  • Indian Beach SubDv.
  • 34234 Zip Code
1838 Oleander Street, Sarasota image
1838 Oleander Street, Sarasota $3,295,000

Poised on one of the prettiest tree-lined West of Trail streets, this modern coastal residence offers the ideal blend of casual elegance, thoughtful design, and everyday ...

  • 4 Beds
  • 3 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
1707 Caribbean Drive, Sarasota image
1707 Caribbean Drive, Sarasota $2,997,000

Fully renovated waterfront estate in Coral Cove, one of Sarasota’s most desirable West of Trail communities. Set on an elevated 0.59-acre corner lot directly across from ...

  • 4 Beds
  • 4 Baths
  • Coral Cove SubDv.
  • 34231 Zip Code
1647 Siesta Drive, Sarasota image
1647 Siesta Drive, Sarasota $1,690,000

Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,023 square feet of living space. Additional opportunity to add bathrooms w...

  • 5 Beds
  • 3 Baths
  • Bayview SubDv.
  • 34239 Zip Code
1372 Harbor Drive, Sarasota image
1372 Harbor Drive, Sarasota $14,950,000

This immaculate Sarasota Bay front estate is prominently positioned on the point of Harbor Drive. It embodies the pinnacle of luxury waterfront living, where timeless ar...

  • 4 Beds
  • 7 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
3921 Maravic Place, Sarasota image
3921 Maravic Place, Sarasota $2,100,000

Virtually Staged. Exceptional West of Trail location! Nestled on a quiet cul-de-sac, this beautifully updated home offers the perfect blend of modern style and everyday c...

  • 4 Beds
  • 3 Baths
  • Moller Sub SubDv.
  • 34231 Zip Code
1805 Goldenrod Street, Sarasota image
1805 Goldenrod Street, Sarasota $3,790,000

Welcome to this exceptional new construction, upgraded residence located West of Trail, featuring 5 bedrooms, 5 full bathrooms, and 3,640 square feet of thoughtfully cura...

  • 5 Beds
  • 5 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
1800 Webber Street, Sarasota image
1800 Webber Street, Sarasota $4,490,000

Nestled in the heart of West of the Trail, this luxury single-story estate represents the pinnacle of modern living. Encompassing 3,262 square feet, the home features 4 b...

  • 4 Beds
  • 6 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
1905 Tulip Drive, Sarasota image
1905 Tulip Drive, Sarasota $1,749,999

**This is the One!** Welcome to a beautifully renovated 3-bedroom, 2.5-bath pool home blending modern luxury with Sarasota charm in one of the area's most desirable locat...

  • 3 Beds
  • 3 Baths
  • Hartland Park SubDv.
  • 34239 Zip Code
859 Patterson Drive, Sarasota image
859 Patterson Drive, Sarasota — 859 $749,000 ▼

Aggressively priced and ideally located West of the Trail just one block from Sarasota Bay, this spacious 4-bedroom, 4-bath residence offers exceptional value in one of ...

  • 4 Beds
  • 4 Baths
  • Bay Haven SubDv.
  • 34234 Zip Code
355 S Shore Drive, Sarasota image
355 S Shore Drive, Sarasota $2,295,000

Build Your Dream Home on Sarasota Bay in Sapphire Shores! Set on an expansive 0.34-acre (14,665-sq.-ft.) waterfront lot, this property presents a rare opportunity to c...

  • Sapphire Shores SubDv.
  • 34234 Zip Code
831 Highland Street, Sarasota image
831 Highland Street, Sarasota $559,000 ▼

Welcome to Indian Beach Sapphire Shores, one of Sarasota's most distinctive and sought-after neighborhoods. Known for its eclectic architecture, artistic character, matur...

  • 3 Beds
  • 2 Baths
  • Highland Pines SubDv.
  • 34234 Zip Code
1387 Harbor Drive, Sarasota image
1387 Harbor Drive, Sarasota $5,590,000

Pre-Construction. To be built. Welcome to effortless coastal luxury in the coveted Harbor Acres neighborhood, where timeless glamour meets breezy, tropical elegance. The ...

  • 4 Beds
  • 5 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
2100 Mcclellan Parkway, Sarasota image
2100 Mcclellan Parkway, Sarasota $6,000,000

Pre-Construction. To be built. Construction in progress, and opportunity for customizations. Situated West of the Trail, this exceptional estate represents the pinnacle o...

  • 5 Beds
  • 7 Baths
  • Mcclellan Park SubDv.
  • 34239 Zip Code
1850 Magnolia Street, Sarasota image
1850 Magnolia Street, Sarasota $2,100,000

Virtually Staged. In the heart of Southside Village, this exceptional home offers one of Sarasota’s sought-after lifestyles. Just west of Tamiami Trail in Poinsettia Park...

  • 4 Beds
  • 4 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
305 S Shore Drive S, Sarasota image
305 S Shore Drive S, Sarasota $3,900,000

Exceptional Sarasota bayfront homesite in Indian Beach/Sapphire Shores. A rare opportunity to build your custom waterfront home on one of Sarasota's most desirable bayfro...

  • Sapphire Shores SubDv.
  • 34234 Zip Code
161 Golden Gate Point, Sarasota image
161 Golden Gate Point, Sarasota $3,995,000

One of the Last Remaining Legacy Properties on Golden Gate Point | Rare Trophy Ownership, Redevelopment & Strategic Hold Opportunity A truly rare offering in one of Saras...

  • Golden Gate Point SubDv.
  • 34236 Zip Code
1864 Clematis St Street, Sarasota image
1864 Clematis St Street, Sarasota $1,799,500

This Spanish Mediterranean style home built in 1925 is nestled in the coveted "West of Trail" subdivision of DeSota Park in the South Poinsettia park Neighborhood just tw...

  • 4 Beds
  • 3 Baths
  • Mcclellan Park SubDv.
  • 34239 Zip Code
2480 Alameda Avenue, Sarasota image
2480 Alameda Avenue, Sarasota $1,395,000 ▼

Located within Sarasota city limits in the Indian Beach/Sapphire Shores neighborhood, 2480 Alameda Ave offers a beautifully remodeled, move-in ready home with real flexib...

  • 4 Beds
  • 4 Baths
  • Sapphire Shores SubDv.
  • 34234 Zip Code
1870 Jasmine Drive, Sarasota image
1870 Jasmine Drive, Sarasota $2,860,000

Experience modern luxury in this stunning new construction home located in Sarasota's highly sought-after West of Trail area. Offering 5 bedrooms, 5.5 bathrooms, and 4,16...

  • 5 Beds
  • 6 Baths
  • Hartland Park SubDv.
  • 34239 Zip Code
1020 23rd Street, Sarasota image
1020 23rd Street, Sarasota $449,900 ▲

STEP BACK IN TIME and experience the charm of "OLD FLORIDA" in this beautifully preserved bungalow located west of North Tamiami Trail in the highly sought after Ringling...

  • 2 Beds
  • 1 Baths
  • Ringling Park SubDv.
  • 34234 Zip Code
1829 Bougainvillea Street, Sarasota image
1829 Bougainvillea Street, Sarasota $4,100,000

Experience the timeless charm and distinctive elegance of this West of Trail luxury cottage, with modern finishes that remain true to its original allure, at 1829 Bougain...

  • 4 Beds
  • 4 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
320 Ringling Point Drive, Sarasota image
320 Ringling Point Drive, Sarasota $2,995,000

Nestled within the exclusive, 11-home Ringling Point enclave of Sarasota's coveted Sapphire Shores neighborhood, this exceptional waterfront residence offers the perfect ...

  • 5 Beds
  • 5 Baths
  • Sapphire Shores SubDv.
  • 34234 Zip Code
1428 Pine Bay Drive, Sarasota image
1428 Pine Bay Drive, Sarasota $1,915,000

A rare opportunity within the coveted West of Trail enclave of Pine Bay, this beautifully renovated residence is nestled on a quiet dead-end street near the historic Fiel...

  • 4 Beds
  • 4 Baths
  • Pine Bay SubDv.
  • 34231 Zip Code
1541 Caribbean Drive, Sarasota image
1541 Caribbean Drive, Sarasota $5,500,000

Perfectly positioned on approximately 130 feet of deep sailboat water, this exceptional waterfront estate offers an extraordinary opportunity to experience the very best ...

  • 5 Beds
  • 6 Baths
  • Coral Cove SubDv.
  • 34231 Zip Code
1395 Harbor Drive, Sarasota image
1395 Harbor Drive, Sarasota $5,750,000

Under Construction. Situated on a prized 1/3-acre homesite in the prestigious Harbor Acres community, this extraordinary custom residence by the award-winning team at All...

  • 5 Beds
  • 6 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
3800 Flores Avenue, Sarasota image
3800 Flores Avenue, Sarasota $4,295,000 ▼

NEW CONSTRUCTION - Experience the pinnacle of Sarasota luxury in this newly completed, move-in-ready residence, ideally located within the City of Sarasota and attractive...

  • 4 Beds
  • 6 Baths
  • Granada SubDv.
  • 34239 Zip Code
1023 Tocobaga Lane, Sarasota image
1023 Tocobaga Lane, Sarasota $3,250,000 ▼

Sophisticated gated living just moments from the heart of downtown Sarasota. Evoking the timeless elegance of Palm Beach with the warmth of Old Florida charm, this except...

  • 3 Beds
  • 4 Baths
  • Tocobaga Bay SubDv.
  • 34236 Zip Code
621 Golden Gate Point, Sarasota image
621 Golden Gate Point, Sarasota $9,999,000

Ultra-Prime Development Opportunity on Golden Gate Point with Unmatched Versatility. This exceptional 0.496-acre site consists of 3 parcels totaling 21,600 sq. ft. and of...

  • Golden Gate Point SubDv.
  • 34236 Zip Code
Turks Cap Place, Sarasota image
Turks Cap Place, Sarasota $650,000

In the sought-after, historic neighborhood of Indian Beach, this large corner lot offers a canvas to design and build your dream home. Spanning nearly 16,000 square feet ...

  • Sapphire Shores SubDv.
  • 34234 Zip Code
3440 Chapel Drive, Sarasota image
3440 Chapel Drive, Sarasota $439,000 ▼

Charming 3BR/2BA Home on a Quiet Cul-de-Sac in a Highly Sought-After Sarasota Location! Welcome to this inviting and well-maintained 3-bedroom, 2-bathroom home perfect...

  • 3 Beds
  • 2 Baths
  • Desoto Terrace SubDv.
  • 34234 Zip Code
2043 Alameda Avenue, Sarasota image
2043 Alameda Avenue, Sarasota $5,500,000

An extraordinary opportunity to build a world-class waterfront estate on Sarasota Bay. This rare direct bayfront vacant parcel at 2043 Alameda Way spans 38,009 SQFT with ...

  • Whitakers SubDv.
  • 34234 Zip Code
2046 Alameda Avenue, Sarasota image
2046 Alameda Avenue, Sarasota $11,000,000

Positioned along the sparkling waters of Sarasota Bay, this extraordinary 1.7 acres of direct bayfront property presents a rare opportunity to create one or two landmark ...

  • Whitakers SubDv.
  • 34234 Zip Code
1703 Alta Vista Street, Sarasota image
1703 Alta Vista Street, Sarasota $1,300,000

Outstanding opportunity to build your dream home in an ideal location. Situated on an 80’ x 110’ corner lot in one of the most desirable areas of Hudson Bayou, this prope...

  • Hudson Bayou SubDv.
  • 34236 Zip Code
6438 Hollywood Boulevard, Sarasota image
6438 Hollywood Boulevard, Sarasota $4,500,000 ▼

Welcome to Coucher du Soleil — French for "Sunset" — a magnificent gated waterfront estate styled after the grand French residences of New Orleans. Breathtaking views of ...

  • 5 Beds
  • 6 Baths
  • Pine Shores Est SubDv.
  • 34231 Zip Code
350 S Shore Drive, Sarasota image
350 S Shore Drive, Sarasota $7,480,000

Imagine owning one of Sarasota Bay’s most exciting waterfront properties, where panoramic views, deep water access, and resort-style living create the kind of lifestyle p...

  • 5 Beds
  • 7 Baths
  • Sapphire Shores SubDv.
  • 34234 Zip Code
1613 Idle Lane, Sarasota image
1613 Idle Lane, Sarasota $650,000

One or more photo(s) has been virtually staged. Investor’s dream in the heart of Sarasota! Welcome to 1613 Idle Lane, a rare opportunity to create your own custom coastal...

  • 3 Beds
  • 3 Baths
  • Does Not Apply SubDv.
  • 34231 Zip Code
1837 Worrington Street, Sarasota image
1837 Worrington Street, Sarasota $611,000 ▼

Renovated 1150 sq. ft. beach cottage west of trail with open floorplan. Updated plumbing, new electric, new metal roof, AC 2020. Golf cart to all your favorite spots, Mor...

  • 2 Beds
  • 2 Baths
  • South Highland SubDv.
  • 34231 Zip Code
1537 Siesta Drive, Sarasota image
1537 Siesta Drive, Sarasota $2,995,000 ▼

Welcome to 1537 Siesta Drive—an exceptional custom coastal contemporary residence ideally positioned between Downtown Sarasota and world-renowned Siesta Key Beach. Built ...

  • 4 Beds
  • 6 Baths
  • South Pointe Woods SubDv.
  • 34239 Zip Code
7503 Starfish Drive, Sarasota image
7503 Starfish Drive, Sarasota $499,900 ▼

Welcome to 7503 Starfish Drive in desirable Sarasota, Florida—an exceptional opportunity to own a slice of paradise just minutes from world-renowned Siesta Key Beach. Nes...

  • 3 Beds
  • 2 Baths
  • Coral Cove SubDv.
  • 34231 Zip Code
7689 Cove Terrace, Sarasota image
7689 Cove Terrace, Sarasota $3,499,000 ▼

Just three homes in from the open waters of Little Sarasota Bay, this beautifully updated waterfront residence in Southpointe Shores offers a rare combination of location...

  • 4 Beds
  • 4 Baths
  • Southpointe Shores SubDv.
  • 34231 Zip Code
1824 Webber Street, Sarasota image
1824 Webber Street, Sarasota $650,000

Investor / Builder Alert! Exceptional WEST OF TRAIL opportunity in one of Sarasota’s desirable neighborhoods, Poinsettia Park. Located just steps from top-rated Southside...

  • 4 Beds
  • 4 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code

West of the Trail

View our featured West of the Trail Listings above or create a search with your own criteria.

One of the hottest Sarasota Real Estate areas is this area known as West of the Trail. Located between Route 41 and the shoreline, this area features homes varying in architectural style and price with many located directly on the water overlooking Sarasota Bay. New construction homes also continue to come on the market as do the occasional land or lot for sale.

Living in this area affords the homeowner the true meaning of the Sarasota lifestyle. With its close proximity to downtown, the beaches of Siesta Key and Lido Key and all the cultural attractions of this beautiful city, the area West of the Trail is truly one of Sarasota's premier locations. 

The homes located West of the Trail in Sarasota range in styles from tastefully appointed estates to mid-century modern to historical mission style bungalows, but all have one thing in common: they enjoy an unmatched location.  

Our website provides property information on listings in real time. That means as soon as they are entered into the the official Realtor®’s database, any search you've created on our website will be updated with notification. All information is updated every 15 minutes so you can be sure to have the most recent information available. 

Customize your search for real estate throughout Sarasota and Manatee Counties in the Advanced Search. You can save searches, and get daily email alerts of new listings, price changes, sold data, and also perform market reports. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Below are all current Sarasota West of the Trail home listings on the MLS. These are sorted from lowest price to highest and are updated every 15 minutes by the official Realtor®’s database. 

For new construction opportunities, contact us.  I can provide you with floorplans, upgrade lists, site plans, unadvertised leaseback and spec home opportunities as well.

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Rick Libro

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5220 Paylor Lane, Lakewood Ranch, FL. 34240

M: 941-504-2850
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