Househuntsarasota.com
  • Home
  • Advanced Search
  • Map Search
  • Buy
  • Sell
  • New Construction
  • Meet Rick
  • Contact Us
Login
941-504-2850

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Sarasota Real Estate - West of the Trail

Address Search

Featured West of the Trail Homes for Sale

1631 Memory Lane, Sarasota image
1631 Memory Lane, Sarasota $825,000

RARE WEST OF THE TRAIL OPPORTUNITY – TURNKEY FURNISHED & READY FOR IMMEDIATE INVESTMENT! Location, location, location! Discover this beautifully updated, turnkey furni...

  • 2 Beds
  • 2 Baths
  • Stickney Point Sub SubDv.
  • 34231 Zip Code
3950 Red Rock Way, Sarasota image
3950 Red Rock Way, Sarasota $8,995,000

Under Construction. Why choose between your perfect sanctuary and stunning sunsets when you can have both. Every evening, the horizon performs a breathtaking masterpiece ...

  • 5 Beds
  • 9 Baths
  • Red Rock Terrace SubDv.
  • 34231 Zip Code
Lucent Place, Sarasota image
Lucent Place, Sarasota $2,800,000

**Prime 2.73-Acre Development Site in the Waterside neighborhood in Lakewood Ranch, Sarasota** An exceptional opportunity in the heart of the Waterside/Lakewood Ranch ...

  • Waterside Village SubDv.
  • 34240 Zip Code
918 Indiana Lane, Sarasota image
918 Indiana Lane, Sarasota $550,000

LOCATED WEST OF THE TRAIL IN A TROPICAL PARADISE. A charming 3-Bedroom, 2-Bath Cottage in Indian Beach–Sapphire Shores. Discover this adorable Cottage in Indian Beach...

  • 3 Beds
  • 2 Baths
  • Bay Haven SubDv.
  • 34234 Zip Code
434 S Shore Drive, Sarasota image
434 S Shore Drive, Sarasota $800,000

Mid-Century Modern Gem with Pool, Character & Endless Potential in Indian Beach Sapphire Shores. Bring your vision and creativity to this mid-century modern home in th...

  • 3 Beds
  • 2 Baths
  • Sapphire Shores SubDv.
  • 34234 Zip Code
1620 N Lodge Drive, Sarasota image
1620 N Lodge Drive, Sarasota $4,500,000

An exceptional opportunity to own a rare waterfront homesite in Cherokee Park, one of Sarasota’s most established neighborhoods. Encompassing an expansive 20,215 square f...

  • Cherokee Park SubDv.
  • 34239 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
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 3,032 square feet of living space. Additional opportunity to add bathrooms w...

  • 5 Beds
  • 3 Baths
  • Bayview SubDv.
  • 34239 Zip Code
1875 Oleander Street, Sarasota image
1875 Oleander Street, Sarasota $2,395,000

Impeccably maintained and thoughtfully designed, this custom-built John Cannon home offers an inviting blend of timeless elegance, spacious interiors, and relaxed Florida...

  • 3 Beds
  • 3 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
1240 Hillview Drive, Sarasota image
1240 Hillview Drive, Sarasota $14,950,000

Introducing “Gatsby Manor,” set along Hillview Drive, one of Sarasota’s most coveted bayfront addresses, often compared to Port Royal for its exclusivity and waterfront l...

  • 4 Beds
  • 4 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
3970 Red Rock Lane, Sarasota image
3970 Red Rock Lane, Sarasota $4,399,000

Pre-Construction. To be built. Introducing an exceptional new custom residence that redefines contemporary luxury in Sarasota's coveted West of Trail neighborhood. Though...

  • 4 Beds
  • 5 Baths
  • Red Rock Terrace SubDv.
  • 34231 Zip Code
5848 Tidewood Avenue, Sarasota image
5848 Tidewood Avenue, Sarasota $7,199,000

Under Construction. Exceptional New Construction | Sarasota Bayfront Living. Experience extraordinary waterfront living in this stunning new-construction residence, perfe...

  • 4 Beds
  • 5 Baths
  • Baywood Colony Westport SubDv.
  • 34231 Zip Code
1777 Alta Vista Street, Sarasota image
1777 Alta Vista Street, Sarasota $975,000

Virtually Staged. Welcome to Cleary Cottage, a charming 1935 bungalow nestled in the highly sought-after Hudson Bayou neighborhood, West of Trail in the heart of Sarasota...

  • 3 Beds
  • 2 Baths
  • Hudson Bayou SubDv.
  • 34236 Zip Code
1605 N Lake Shore Drive, Sarasota image
1605 N Lake Shore Drive, Sarasota $1,595,000

Discover the ultimate West-of-Trail canvas at 1605 N Lake Shore Drive, an extraordinary opportunity to design a custom architectural masterpiece in Sarasota’s prestigious...

  • Oyster Bay Estates SubDv.
  • 34231 Zip Code
4307 Camino Real, Sarasota image
4307 Camino Real, Sarasota $2,999,000

Distinctive Architecture. Space to Unwind. West of Trail. Set on a tropically landscaped half-acre corner lot on a private dead-end street off Camino Real, this custom h...

  • 4 Beds
  • 3 Baths
  • Johnson Estates SubDv.
  • 34231 Zip Code
5122 Kestral Park S, Sarasota image
5122 Kestral Park S, Sarasota $1,450,000

Discover an exceptional opportunity in the Landings, one of Sarasota's most sought-after communities, ideally situated West of the Trail. Custom-built and lovingly mainta...

  • 4 Beds
  • 3 Baths
  • The Landings SubDv.
  • 34231 Zip Code
2423 Hickory Avenue, Sarasota image
2423 Hickory Avenue, Sarasota $410,000

A storybook setting for your Sarasota dream home. As Sarasota continues to grow northward, this fabled little neighborhood becomes all the more desirable. Tucked along a ...

  • Sarasota Bay Park SubDv.
  • 34234 Zip Code
1023 Tocobaga Lane, Sarasota image
1023 Tocobaga Lane, Sarasota $2,995,000

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
315 S Shore Drive, Sarasota image
315 S Shore Drive, Sarasota $4,950,000

House never flooded, including during Hurricanes Milton and Helene, and protected by a generator! Built as a solid concrete structure on concrete pilings, this home was e...

  • 4 Beds
  • 4 Baths
  • Sapphire Shores SubDv.
  • 34234 Zip Code
1730 Wisconsin Lane, Sarasota image
1730 Wisconsin Lane, Sarasota $1,495,000

Virtually Staged. LOWEST-PRICED NEW CONSTRUCTION WEST OF TRAIL. Completed in 2026 and ideally located close to Siesta Key and downtown Sarasota, this modern 4-bedroom plu...

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

Pre-Construction. To be built. Completion anticipated in a few months. Situated West of the Trail, this exceptional estate represents the pinnacle of luxury living in Sar...

  • 5 Beds
  • 7 Baths
  • Mcclellan Park SubDv.
  • 34239 Zip Code
1703 Starling Drive Unit 1703, Sarasota image
1703 Starling Drive Unit 1703, Sarasota $645,000

Eagles Point Villa | The Landings, West of the Trail Tucked behind The Landings’ 24 hour manned gatehouse in the coveted area West of the Trail, this Eagles Point villa ...

  • 3 Beds
  • 3 Baths
  • The Landings SubDv.
  • 34231 Zip Code
1734 Wisconsin Lane, Sarasota image
1734 Wisconsin Lane, Sarasota $1,495,000

LOWEST-PRICED NEW CONSTRUCTION WEST OF TRAIL. Completed in 2026 and ideally located close to Siesta Key and downtown Sarasota, this modern 4-bedroom plus den, 4.5-bath re...

  • 4 Beds
  • 5 Baths
  • Shoreland Woods SubDv.
  • 34239 Zip Code
1749 Sandalwood Drive, Sarasota image
1749 Sandalwood Drive, Sarasota $2,649,900

Imagine beginning your morning with coffee overlooking the water, spending the afternoon exploring Sarasota Bay by boat, and returning home for an evening beside the pool...

  • 4 Beds
  • 4 Baths
  • Southpointe Shores SubDv.
  • 34231 Zip Code
1695 Hyde Park Street, Sarasota image
1695 Hyde Park Street, Sarasota $1,650,000

Excellent location in Sarasota's Southside Village. This beautifully maintained 3-bedroom, 2.5-bathroom residence offers an excellent combination of thoughtful design, pr...

  • 3 Beds
  • 3 Baths
  • Mckune Sub SubDv.
  • 34239 Zip Code
780 Indian Beach Circle, Sarasota image
780 Indian Beach Circle, Sarasota $1,399,000

A TRUE TRANSFORMATION in Sarasota’s coveted Indian Beach/Sapphire Shores neighborhood, 780 Indian Beach Circle has undergone a comprehensive, permitted reconstruction ext...

  • 3 Beds
  • 4 Baths
  • West Shore SubDv.
  • 34234 Zip Code
1630 Bonita Lane, Sarasota image
1630 Bonita Lane, Sarasota $2,275,000

Welcome to this charming single-family residence located in the highly sought-after Granada neighborhood. Step inside to find a welcoming layout complete high ceilings, o...

  • 3 Beds
  • 3 Baths
  • Granada SubDv.
  • 34239 Zip Code
844 Patterson Drive, Sarasota image
844 Patterson Drive, Sarasota $649,900

Welcome to 844 Patterson Drive, a charming coastal retreat tucked away in Sarasota's beautiful Indian Beach–Sapphire Shores neighborhood! Situated on a spacious corner lo...

  • 3 Beds
  • 2 Baths
  • Bay Haven SubDv.
  • 34234 Zip Code
1800 Alta Vista Street, Sarasota image
1800 Alta Vista Street, Sarasota $1,250,000 ▼

Virtually Staged. Step into the timeless character and charm of this beautiful 1940s home in highly sought-after Avondale, ideally situated West of the Trail on a corner ...

  • 3 Beds
  • 2 Baths
  • Avondale SubDv.
  • 34236 Zip Code
1749 Lincoln Park Circle, Sarasota image
1749 Lincoln Park Circle, Sarasota $3,350,000

Downtown Waterfront Living with Direct Access to Sarasota Bay and the Gulf of Mexico. A rare opportunity to own a deeded boat slip with a 10,000-pound lift, accommodating...

  • 4 Beds
  • 4 Baths
  • Lincoln Park On Hudson Bayou SubDv.
  • 34236 Zip Code
7780 Holiday Drive N, Sarasota image
7780 Holiday Drive N, Sarasota $1,900,000 ▼

Welcome to this immaculate, move-in ready Sarasota estate on a quiet, no-outlet cul-de-sac west of the Trail, just minutes from both the world-famous beaches of Siesta Ke...

  • 4 Beds
  • 3 Baths
  • Holiday Harbor SubDv.
  • 34231 Zip Code
1386 Tangier Way, Sarasota image
1386 Tangier Way, Sarasota $16,000,000

Pre-Construction. To be built. To be complete in 3-4 months. Situated in San Remo Estates, one of Sarasota's most exclusive waterfront communities, this upcoming new cons...

  • 4 Beds
  • 6 Baths
  • San Remo Estates SubDv.
  • 34239 Zip Code
1741 Stanford Lane, Sarasota image
1741 Stanford Lane, Sarasota $1,795,000

Less than 2 miles from world-famous Siesta Key, this 4-bedroom, 3-bath, 3-car garage pool home in Aqualane Estates offers a rare combination of waterfront living, bold de...

  • 4 Beds
  • 3 Baths
  • Aqualane Estates SubDv.
  • 34231 Zip Code
621 40th Street, Sarasota image
621 40th Street, Sarasota $1,360,000

Location, Location, Location! Ready to build, bring your architect and builder to this wonderful and oversized lot with an additional access easement to Bay Shore Rd. Sit...

  • Indian Beach SubDv.
  • 34234 Zip Code
1406 Tangier Way, Sarasota image
1406 Tangier Way, Sarasota $6,500,000

Welcome to 1406 Tangier Way, a breathtaking expression of coastal contemporary luxury in San Remo Estates in Sarasota, where architectural excellence meets waterfront ser...

  • 4 Beds
  • 3 Baths
  • San Remo Estates SubDv.
  • 34239 Zip Code
940 22nd Street, Sarasota image
940 22nd Street, Sarasota $475,000

PRIME SARASOTA CITY LAND — CLOSE TO WATER & OUT OF FLOOD ZONE! Outstanding build opportunity. This 8,200 sq. ft. lot sits just steps from Sarasota Bay with 2-story design...

  • Weber Sub SubDv.
  • 34234 Zip Code
4946 Brywill Circle, Sarasota image
4946 Brywill Circle, Sarasota $1,495,000

Discover an exquisite blend of Old-World charm and modern luxury in this custom Mediterranean jewel. Located in the heart of Sarasota’s Historic Museum Area in Sapphire S...

  • 3 Beds
  • 3 Baths
  • Sapphire Shores SubDv.
  • 34234 Zip Code
1789 Loma Linda Street, Sarasota image
1789 Loma Linda Street, Sarasota $1,395,000

The West of Trail BEST BUY!! Located between Osprey Avenue and Orange Avenue. Rarely will you find a 2500+ square foot cement block home on an oversized corner lot (100' ...

  • 3 Beds
  • 2 Baths
  • Pomelo Place SubDv.
  • 34239 Zip Code
1881 Orchid Street, Sarasota image
1881 Orchid Street, Sarasota $998,000

*VIRTUALLY STAGED* Desirable West of the Trail location in the sought-after Southside school district! Welcome to 1881 Orchid Street, a beautifully updated 3-bedroom, 2-...

  • 3 Beds
  • 2 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
1359 Tearose Place, Sarasota image
1359 Tearose Place, Sarasota $1,199,000

Welcome to Mandarin Park, one of Sarasota’s most desirable gated communities, where beautiful homes, privacy, and an unbeatable location come together in the heart of the...

  • 2 Beds
  • 2 Baths
  • Mandarin Park SubDv.
  • 34239 Zip Code
4451 Charles Lane, Sarasota image
4451 Charles Lane, Sarasota $985,000 ▼

Built in 1910, this original kit house offers a rare opportunity to own a remarkable piece of Sarasota history. Once ordered by mail from, the residence has been extensiv...

  • 2 Beds
  • 3 Baths
  • Corwood SubDv.
  • 34234 Zip Code
1820 Stanford Lane, Sarasota image
1820 Stanford Lane, Sarasota $999,000 ▼

This is the one * LOCATED IN THE HIGHLY DESIRABLE AQUALANE ESTATES, JUST A MILE FROM WORLD FAMOUS SIESTA KEY BEACH, THIS CUSTOM HOME OFFERS AN INCREDIBLE OPPORTUNITY TO O...

  • 4 Beds
  • 2 Baths
  • Aqualane Estates SubDv.
  • 34231 Zip Code
1712 Siesta Drive, Sarasota image
1712 Siesta Drive, Sarasota $499,900 ▼

Wonderful home! Was used as an AirBNB/VRBO for years and now it's available for you! Furniture negotiable. Walk to Southside Elementary school! Superior location in S...

  • 2 Beds
  • 1 Baths
  • Granada Park SubDv.
  • 34239 Zip Code
731 42nd Street, Sarasota image
731 42nd Street, Sarasota $1,445,000

Welcome to this stunning BRAND-NEW CONSTRUCTION home in Sarasota, offering 2,678 square feet of beautifully designed living space with 4 bedrooms, 4.5 bathrooms, a privat...

  • 4 Beds
  • 5 Baths
  • Indian Beach SubDv.
  • 34234 Zip Code
1761 Sandalwood Drive, Sarasota image
1761 Sandalwood Drive, Sarasota $1,899,000 ▼

Nestled within the desirable West of Trail Southpointe Shores Community, this home benefits from top-rated school zones and a serene, upscale waterfront atmosphere. This ...

  • 3 Beds
  • 2 Baths
  • Southpointe Shores SubDv.
  • 34231 Zip Code
771 Indian Beach Circle, Sarasota image
771 Indian Beach Circle, Sarasota $1,250,000

Wake up to the salt air. This gorgeous updated Indian Beach home is perfectly situated close to downtown, west of Trail/west of Bayshore. Take a 4-minute walk to see the ...

  • 4 Beds
  • 2 Baths
  • Indian Beach Map Of SubDv.
  • 34234 Zip Code
1621 Bay Point Court, Sarasota image
1621 Bay Point Court, Sarasota $5,395,000 ▼

NOW PRICED BELOW RECENT APPRAISAL. Behind a private gate and beneath a canopy of tropical foliage, 1621 Bay Point Court offers a secluded waterfront retreat just moments ...

  • 4 Beds
  • 5 Baths
  • Mooring At Bay Pointe The SubDv.
  • 34236 Zip Code
1722 North Drive, Sarasota image
1722 North Drive, Sarasota $2,690,000

Rarely available in Cherokee Park, widely regarded as one of Sarasota’s most desirable West of Trail neighborhoods, 1722 North Drive presents an extraordinary opportunity...

  • 3 Beds
  • 2 Baths
  • Cherokee Park SubDv.
  • 34239 Zip Code
463 Acacia Drive, Sarasota image
463 Acacia Drive, Sarasota $680,000

Build something extraordinary in Sapphire Shores, one of Sarasota's most coveted bayfront neighborhoods, where canopied streets, custom architecture and the open water of...

  • Sapphire Shores SubDv.
  • 34234 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.

Like or Share

Rick Libro

REALTOR®

5220 Paylor Lane, Lakewood Ranch, FL. 34240

M: 941-504-2850
Email

How much is your home worth?

...get instant property value now!

Interactive Map Search

Search for Homes by Lifestyle

  • Beach Front Homes and Condos
  • Boating Properties
  • Golf
  • Green Homes
  • Luxury Condos
  • Pet-Friendly Condos
  • Resort Style Communities
  • 55+ Communities

Search Lakewood Ranch Communities

  • The Alcove
  • Arbor Grande
  • Aurora
  • Avalon Woods
  • Azario Esplanade
  • Azario Park East
  • Bridgewater
  • Boca Grove
  • Central Park
  • Country Club East
  • Cresswind
  • Del Webb
  • Del Webb Catalina
  • Edgewater
  • Esplanade
  • Greenbrook
  • Harmony
  • Indigo
  • The Isles
  • Kingfisher Estates
  • The Lake Club
  • Lakeshore at Main Street
  • Lakewood National Golf Club
  • Lakewood Ranch Country Club
  • Lorraine Lakes
  • Mallory Park
  • Miramar
  • Monarch Acres
  • Monterey
  • Palisades
  • Polo Run
  • Sapphire Point
  • Savanna
  • Solera
  • Star Farms
  • Summerfield
  • Sweetwater
  • Watercrest
  • Waterfront
  • Waterside - Lakehouse Cove
  • Waterside - Shoreview
  • Wild Blue at Waterside
  • Windward
  • Woodleaf Hammock

Market Reports

  • Bird Key
  • Bradenton
  • Bradenton/Braden River
  • Bradenton/Braden River/University Park
  • Bradenton/Braden River/Lakewood Rch
  • Bradenton/Lakewood Ranch/Lakewood Rch
  • Bradenton / Lakewood Ranch
  • Bradenton/Palma Sola
  • Downtown Sarasota
  • Espanade on Palmer Ranch
  • Lakewood Ranch
  • Lido Key
  • Longboat Key
  • Manatee County
  • Osprey/Nokomis
  • Palmer Ranch
  • Panther Ridge
  • Parrish
  • Sarasota Market Report
  • Sarasota County
  • Sarasota/Crescent Beach/Siesta Key
  • Sarasota/Gulf Gate Branch
  • Sarasota/Pinecraft
  • Sarasota West of Trail
  • Siesta Key
  • University Park
  • Venice

Welcome to Our Website!

Please watch the short video below to see how this site will help you buy or sell your next home!

 

 

Downtown Sarasota Market Report
University Park Market Report

RICK LIBRO is a recipient of the FIVE STAR PROFESSIONAL AWARD. Year after year, he receives the highest ratings for exceptional service to his clients.

 

Ricks Realtor Five Star Status

 

Mortgage Calculator

Amount of Loan
Annual Interest Rate
%
Term of Loan
Years
Calculate

Does not include any taxes or fees.
Please consult a financial professional.

 

Buying & Selling Made Easy

 Freshest Data Available
 Active Listings Only
 Customizable Search Options
 New Listing Alerts
 Instant Home Value Assessments

 

Translate Site

  • Home
  • Map Search
  • Buy
  • Sell
  • New Construction Homes
  • Market Reports
  • Meet Rick
  • Contact Us

 

RICK LIBRO - REALTOR®
FINE PROPERTIES

5220 Paylor Lane, Lakewood Ranch, FL 34240

Ph: 941-504-2850

Email: RickLibro@gmail.com

© All Rights Reserved - Privacy Policy

Advanced Searches

  • Condo Search
  • Foreclosure Search
  • Zip Code Search
  • MLS # Search
  • Sold Search
  • Address Search
  • Panther Ridge/Myakka
  • Sarasota West of the Trail
  • University Park
IDX Real Estate Websites by
• Accessibility • Terms • Privacy