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Sarasota West of the Trail Real Estate Search

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Sarasota West of the Trail Market Report

Follow active listings, pending sales, and homes sold within the past six months in Sarasota West of the Trail. The report updates automatically as MLS data changes.

View the Sarasota West of the Trail Market Report

Active Listings

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
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
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
1730 Wisconsin Lane, Sarasota image
1730 Wisconsin Lane, Sarasota $1,495,000

Professional photos coming soon. LOWEST-PRICED NEW CONSTRUCTION WEST OF TRAIL. Completed in 2026 and ideally located close to Siesta Key and downtown Sarasota, this moder...

  • 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
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
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
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
1965 Hibiscus Street, Sarasota image
1965 Hibiscus Street, Sarasota $1,084,000

Welcome to 1965 Hibiscus Street, a beautifully updated Sarasota home in a highly desirable location west of the Trail. Thoughtfully improved and move-in ready, this invit...

  • 3 Beds
  • 2 Baths
  • Desota Park SubDv.
  • 34239 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
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
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
1960 Boyce Street, Sarasota image
1960 Boyce Street, Sarasota $3,895,000

Modern architecture, exceptional craftsmanship and resort-style outdoor living define this barely lived-in 2023-built contemporary residence. Offered furnished and immedi...

  • 4 Beds
  • 5 Baths
  • Hartsdale SubDv.
  • 34239 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
1740 S Orange Avenue, Sarasota image
1740 S Orange Avenue, Sarasota $5,500,000

Pre-Construction. To be built. UNDER CONSTRUCTION — HEMINGWAY LUXURY MODEL BY COURTYARD MODERN HOMES- OR BUILD TO SUIT STARTING AT $4,500,000.00 -- A striking new express...

  • 5 Beds
  • 6 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
2631 Puritan Terrace, Sarasota image
2631 Puritan Terrace, Sarasota $2,150,000

Welcome to this refreshed, single-story residence in one of Sarasota’s most coveted West of Trail neighborhoods. Set on a generous 15,625-square-foot lot, the 3,675-squar...

  • 4 Beds
  • 4 Baths
  • Bay View Heights SubDv.
  • 34239 Zip Code
1671 Arlington Street, Sarasota image
1671 Arlington Street, Sarasota $3,050,000 ▲

Contemporary architecture, private poolside living, and Southside Village just one block away define the appeal of 1671 Arlington Street. Newly completed in a prime West-...

  • 5 Beds
  • 6 Baths
  • Lewis Combs Sub SubDv.
  • 34239 Zip Code
1354 Tearose Place, Sarasota image
1354 Tearose Place, Sarasota $1,600,000 ▼

Discover the ultimate in modern Sarasota living in this stunning, completely renovated home located in the highly desirable West of Trail gated community near downtown Sa...

  • 3 Beds
  • 3 Baths
  • Mandarin Park SubDv.
  • 34239 Zip Code
1444 Harbor Drive, Sarasota image
1444 Harbor Drive, Sarasota $6,999,900

Virtually Staged. Welcome to this exceptional waterfront home in the highly sought-after Harbor Acres neighborhood. With more than 5,000 square feet of living space, this...

  • 5 Beds
  • 7 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
1426 S Osprey Avenue, Sarasota image
1426 S Osprey Avenue, Sarasota $2,999,000

Welcome to an understated masterclass in coastal sophistication. Custom-built by renowned builder Jonas Yoder, this new construction residence offers over 3,000 square fe...

  • 4 Beds
  • 4 Baths
  • Matheneys Sub SubDv.
  • 34239 Zip Code
3424 Old Oak Drive, Sarasota image
3424 Old Oak Drive, Sarasota $1,039,000

A private garden retreat in one of Sarasota’s most coveted West of Trail locations.** Nestled among lush tropical gardens and mature landscaping, 3424 Old Oak Drive is a ...

  • 3 Beds
  • 2 Baths
  • Shoreland Woods SubDv.
  • 34239 Zip Code
1640 Waldemere Street, Sarasota image
1640 Waldemere Street, Sarasota $5,400,000 ▼

AMAZING PRICE REDUCTION, THIS HOME IS NOW PRICED BELOW MARKET VALUE. Take advantage of this opportunity now! Where the World's Most Exclusive Resorts Inspire Everyday L...

  • 5 Beds
  • 6 Baths
  • Lewis Combs Sub SubDv.
  • 34239 Zip Code
1798 Lincoln Park Circle, Sarasota image
1798 Lincoln Park Circle, Sarasota $2,425,000 ▼

Discover exceptional West of Trail living in Lincoln Park, an intimate waterfront enclave located along Hudson Bayou in Sarasota, Florida. This beautifully appointed resi...

  • 3 Beds
  • 3 Baths
  • Lincoln Park On Hudson Bayou SubDv.
  • 34236 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
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
1829 Bougainvillea Street, Sarasota image
1829 Bougainvillea Street, Sarasota $3,850,000 ▼

Some homes are built to follow a trend. Others possess a character that transcends time. Welcome to The Bougainvillea House, a Sarasota original with a story more than...

  • 4 Beds
  • 4 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
1891 Prospect Street, Sarasota image
1891 Prospect Street, Sarasota $2,500,000

Discover this UNIQUELY RARE OPPORTUNITY in the Coveted West of the Trail Neighborhood, amongst other very beautiful multi-million-dollar homes (two back-to-back lots, 189...

  • 2 Beds
  • 1 Baths
  • Floyd & Cameron Sub SubDv.
  • 34239 Zip Code
1794 Cunliff Lane, Sarasota image
1794 Cunliff Lane, Sarasota $2,997,000 ▼

Find your sanctuary in this exquisite Allegra custom home, ideally located on one of the few non-throughfare streets in the highly coveted West of the Trail neighborhood....

  • 4 Beds
  • 3 Baths
  • Mcclellan Park SubDv.
  • 34239 Zip Code
1959 Wisteria Street, Sarasota image
1959 Wisteria Street, Sarasota $3,150,000

Welcome to 1959 Wisteria Street – a beautiful New Construction Single Story home, West of the Trail, that your clients will love! This just-completed modern coastal sing...

  • 3 Beds
  • 4 Baths
  • Desota Park SubDv.
  • 34239 Zip Code
3000 Southwest Drive, Sarasota image
3000 Southwest Drive, Sarasota $11,995,000 ▼

One of Sarasota’s greatest bayfront estates, this stunning 1.38 acre waterfront home has recently undergone a comprehensive renovation throughout, enhancing every room wi...

  • 5 Beds
  • 7 Baths
  • Cherokee Park SubDv.
  • 34239 Zip Code
1340 Harbor Drive, Sarasota image
1340 Harbor Drive, Sarasota $11,450,000 ▲

Under Construction. Best price under construction opportunity in Harbor Acres, a one-third-acre waterfront property on the widest part of the neighborhood's deep-water ha...

  • 4 Beds
  • 7 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
1509 Flower Drive, Sarasota image
1509 Flower Drive, Sarasota — Allegra Homes $5,375,000

Under Construction. Allegra Homes presents the custom-built Southside IV in Harbor Acres—one of Sarasota’s signature bayfront enclaves. Designed for elevated everyday liv...

  • 5 Beds
  • 5 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
1538 S Orange Avenue, Sarasota image
1538 S Orange Avenue, Sarasota $1,950,000

This revitalized 2,550 sq' (+/-) single level home is in coveted Harbor Acres and within walking distance to the quaint Southside Village, Sarasota Bay and the energizing...

  • 3 Beds
  • 4 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
1821 Lincoln Drive, Sarasota image
1821 Lincoln Drive, Sarasota $5,425,000 ▲

Under Construction. This exceptional, boater’s residence is ideally positioned on Hudson Bayou, designed to impress at every turn. Showcasing the very best of Sarasota’s ...

  • 4 Beds
  • 5 Baths
  • Avondale SubDv.
  • 34236 Zip Code
1759 Waldemere Street, Sarasota image
1759 Waldemere Street, Sarasota $4,099,999 ▼

Virtually Staged. West of Trail luxury meets modern innovation at 1759 Waldemere Street. This brand-new, custom-built residence embodies timeless design, contemporary cra...

  • 4 Beds
  • 5 Baths
  • Midwood Manor SubDv.
  • 34239 Zip Code
1541 Flower Drive, Sarasota image
1541 Flower Drive, Sarasota $1,870,000 ▼

This unique home is in the desirable neighborhood of Harbor Acres. World renowned Selby Botanical Gardens is less than a mile from your new home. This mid-century jewel w...

  • 4 Beds
  • 4 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
1479 Bay Point Drive, Sarasota image
1479 Bay Point Drive, Sarasota $5,495,000 ▼

Being in the same family for 75 years, this is a rare opportunity to own a stunning, nearly half-acre waterfront lot in the highly desirable Bay Point Park neighborhood o...

  • 4 Beds
  • 3 Baths
  • Bay Point Park SubDv.
  • 34236 Zip Code
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Jan and Scott Langa

Scott & Jan Langa

Broker Associates
Coldwell Banker Residential Real Estate
423 St Armands Circle
Sarasota, FL 34236

Jan: 941-404-0802
Scott: 941-404-0835

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