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Sarasota West of the Trail Real Estate Search

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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
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
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
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
1915 Clematis Street, Sarasota image
1915 Clematis Street, Sarasota $3,200,000

A timeless statement of modern luxury, this impeccably reimagined West of Trail residence exudes sophistication, serenity and refined coastal elegance. Completely remodel...

  • 4 Beds
  • 4 Baths
  • Mcclellan Park SubDv.
  • 34239 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
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
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
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
1734 Wisconsin Lane, Sarasota image
1734 Wisconsin Lane, Sarasota $1,599,000 ▼

Less than 4 miles to Siesta Key Beach and under 3 miles to Downtown Sarasota, this newly built 4-bed modern home in Sarasota delivers luxury living, investment flexibilit...

  • 4 Beds
  • 5 Baths
  • Cherokee Park SubDv.
  • 34239 Zip Code
1731 Siesta Drive, Sarasota image
1731 Siesta Drive, Sarasota $2,595,000

Under Construction. Brand new construction with ultra-luxury finishes, estimated for completion end of August 2026. This is the one. A statement home in one of Sarasota’s...

  • 4 Beds
  • 4 Baths
  • Bayview SubDv.
  • 34239 Zip Code
1931 High Point Circle, Sarasota image
1931 High Point Circle, Sarasota $1,450,000 ▼

FULLY FURNISHED SHORT TERM RENTAL PROPERTY. Experience the best of "West of Trail" living in this impeccably maintained, renovated pool home situated on an OVERSIZED LOT....

  • 3 Beds
  • 2 Baths
  • Hudson Bayou SubDv.
  • 34236 Zip Code
1717 Alta Vista Street, Sarasota image
1717 Alta Vista Street, Sarasota $3,095,000 ▼

Prime Location in the Hudson Bayou neighborhood. Built in 2023 this home offers 5 Bedrooms, 4.5 bathrooms and designer finishes. The interior features an open floor plan ...

  • 5 Beds
  • 5 Baths
  • Prime Sub SubDv.
  • 34236 Zip Code
1880 Loma Linda Street, Sarasota image
1880 Loma Linda Street, Sarasota $1,795,000 ▼

Sought after West of Trail location close to Southside Village and on a cul-de-sac street. The home boasts almost 3000 square feet of airy living space and an open floor ...

  • 4 Beds
  • 4 Baths
  • Floyd & Cameron Sub SubDv.
  • 34239 Zip Code
1714 Waldemere Street, Sarasota image
1714 Waldemere Street, Sarasota $1,650,000 ▼

Rarely available 2001 built one story home on a 75 ft wide lot in the prime heart of West of Trail/ Southside Village area. One block to Sarasota Memorial Hospital and 3 ...

  • 4 Beds
  • 3 Baths
  • Hudson Bayou SubDv.
  • 34239 Zip Code
1865 Orchid Street, Sarasota image
1865 Orchid Street, Sarasota $1,795,000 ▼

Welcome to your dream home in Sarasota’s coveted West of Trail neighborhood—one of the area’s most sought-after locations, known for its quiet, tree-lined streets, upscal...

  • 4 Beds
  • 3 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
1850 Webber Street, Sarasota image
1850 Webber Street, Sarasota $3,790,000 ▼

Virtually Staged. West of trail, 2026 Custom Build, Exquisite Modern Mediterranean estate with a seamless blend of classic architecture and contemporary finishes. Thi...

  • 6 Beds
  • 4 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
1714 South Drive, Sarasota image
1714 South Drive, Sarasota $2,095,000 ▼

Virtually Staged. Tucked beneath a canopy of mature trees in one of Sarasota’s most coveted neighborhoods, 1714 South Drive presents a rare opportunity to secure a prime ...

  • 4 Beds
  • 4 Baths
  • Cherokee 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
1504 S Lodge Drive, Sarasota image
1504 S Lodge Drive, Sarasota $6,950,000 ▼

Dreaming of breathtaking sunsets? This property is for you! A one of a kind bayfront lot located in highly sought-after Cherokee Park, West of Trail. Located in "X" flood...

  • 4 Beds
  • 4 Baths
  • Cherokee Park SubDv.
  • 34239 Zip Code
1671 Arlington Street, Sarasota image
1671 Arlington Street, Sarasota $2,995,000

Located West of Trail, this beautiful new construction five-bedroom, five-and-a-half-bathroom residence captures the essence of Sarasota living. Designed with both comfor...

  • 5 Beds
  • 6 Baths
  • Lewis Combs Sub SubDv.
  • 34239 Zip Code
1394 Harbor Drive, Sarasota image
1394 Harbor Drive, Sarasota $7,750,000 ▼

Presenting a distinguished waterfront estate located in Sarasota’s premier bayfront community, Harbor Acres, widely regarded as the city’s most coveted neighborhood. Perf...

  • 4 Beds
  • 6 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
1611 Hyde Park Street, Sarasota image
1611 Hyde Park Street, Sarasota $3,750,000 ▼

Located in Sarasota’s established West of Trail neighborhood, this gated and fenced 1920 Craftsman residence offers a rare double lot and a guest cottage. Originally cons...

  • 4 Beds
  • 4 Baths
  • 34239 Zip Code
1704 Wisconsin Lane, Sarasota image
1704 Wisconsin Lane, Sarasota $625,000 ▼

Welcome to your perfect coastal escape—an inviting cottage offering charm, comfort, and an ideal location away from the hustle and bustle of city life. Just a few miles f...

  • 2 Beds
  • 1 Baths
  • Bayview 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 $12,750,000 ▼

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 $10,995,000

Under Construction. Superb New Construction opportunity in Harbor Acres, a one-third-acre waterfront property on the widest part of the neighborhood's deep-water harbor o...

  • 4 Beds
  • 7 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
1347 Harbor Drive, Sarasota image
1347 Harbor Drive, Sarasota $4,000,000 ▼

Exceptional Harbor Acres modern residence offering 5 bedrooms, including a sunroom converted by the owners into a true 5th bedroom (closet and A/C). Warm contemporary des...

  • 5 Beds
  • 4 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
1500 Bayview Drive, Sarasota image
1500 Bayview Drive, Sarasota $8,750,000 ▼

Nestled in the heart of Sarasota, Florida, "The Seathrough House" stands as a testament to timeless elegance and modern sophistication. Designed by the acclaimed architec...

  • 5 Beds
  • 5 Baths
  • Bay View Heights SubDv.
  • 34239 Zip Code
1958 Morris Street, Sarasota image
1958 Morris Street, Sarasota $1,099,900 ▼

Virtually Staged. Now offering buyer incentives and priced below appraised value! This exceptional single-family pool home offers the perfect blend of space, flexibility,...

  • 4 Beds
  • 3 Baths
  • Hartsdale SubDv.
  • 34239 Zip Code
1509 Flower Drive, Sarasota image
1509 Flower Drive, Sarasota $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
1521 Bay Point Drive, Sarasota image
1521 Bay Point Drive, Sarasota $14,900,000

Pre-Construction. To be built. Soon to be under construction. Located on the coveted waterfront of Bay Point Drive, this extraordinary custom residence represents a rare ...

  • 4 Beds
  • 5 Baths
  • Bay Point Park SubDv.
  • 34236 Zip Code
1516 S Orange Avenue, Sarasota image
1516 S Orange Avenue, Sarasota $4,475,000 ▼

The highly-acclaimed team of professionals at Allegra Homes has yet again created a vision of luxury, elegance and simplistic functionality. A dynamic 4,224 sq. ft. open ...

  • 4 Beds
  • 5 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
3331 Old Oak Drive, Sarasota image
3331 Old Oak Drive, Sarasota $1,895,000 ▼

A private, gated masterpiece where Old Florida romance meets modern coastal luxury. Tucked within the coveted West of the Trail enclave, this exquisitely reimagined esta...

  • 4 Beds
  • 4 Baths
  • Shoreland Woods SubDv.
  • 34239 Zip Code
1749 Lincoln Park Circle, Sarasota image
1749 Lincoln Park Circle, Sarasota $3,575,000 ▼

Downtown Waterfront with a straight route to Sarasota Bay and the Gulf of Mexico! Making this home a rare find is the deeded slip, 10,000-pound lift, space for a 30-foot ...

  • 4 Beds
  • 4 Baths
  • Lincoln Park On Hudson Bayou SubDv.
  • 34236 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 $4,299,999 ▼

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
1642 Bahia Vista Street, Sarasota image
1642 Bahia Vista Street, Sarasota $3,895,000 ▼

Stunning New Construction by Award-Winning Architect Dan Lear in coveted West of Trail Neighborhood** This meticulously designed luxury home offers the perfect blend of ...

  • 4 Beds
  • 5 Baths
  • Seminole Heights SubDv.
  • 34239 Zip Code
1838 Alta Vista Street, Sarasota image
1838 Alta Vista Street, Sarasota $3,200,000 ▼

Ensconced in the heart of the highly esteemed West-of-Trail Avondale neighborhood, this stunning 5-bedroom, 4.5-bath, 4400 square foot residence seamlessly blends timeles...

  • 5 Beds
  • 6 Baths
  • Avondale SubDv.
  • 34236 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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Scott:  941-404-0835   Jan:  941-404-0802

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Jan & Scott Langa - Broker Associates    
Coldwell Banker Residential Real Estate
423 St Armands Circle
Sarasota, Fl, 34236
(j) 941-404-0802 (s) 941-404-0835



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