Sarasota, FL Homes

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  /28

  $648,500

  • 2 Beds
  • 2 Baths
  • 1,334 Sq Ft

  1857 Siesta Dr, Sarasota, FL 34239

  Opportunity knocks in one of Sarasota’s most desirable locations! Situated just over the North Bridge and only one mile to the world-famous Siesta Key Beach, this charming 2-bedroom home sits on just under a 1/4 acre lot with NO HOA or deed restrictions. Whether you’re a first-time buyer wanting that coastal lifestyle, or an investor seeking your next high-potential property, this checks off all

  

  Noah Ward

  EXP REALTY LLC

  (941) 294-6143

  1857 Siesta Dr, Sarasota, FL 34239
• 

  Explore Southside

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  /33

  $10,000 per month

  • 3 Beds
  • 5 Baths
  • 3,073 Sq Ft
  • House for Rent

  1716 Stapleton St, Sarasota, FL 34239

  Luxurious Fully Furnished, 3-Bedroom Home with Elevator in Gated Sarasota Community – Now Available for Rent! Short Term and Long Term rental options. AVAILABLE 10/1/25Discover your sanctuary in one of Sarasota’s most desirable enclaves—West of the Trail—where homes are rarely available. Nestled in the exclusive, gated community of Granada Park, this stunning 3-bedroom, 3 full-bath, and 2

  

  Tracy Srodes

  FINE PROPERTIES

  (941) 393-0480

  1716 Stapleton St, Sarasota, FL 34239
• 

  

  /2

  $3,530,000 Sold Jul 28, 2025

  • 3,262 Sq Ft
  • $1082/SF
  • 356 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2025

  1800 Webber St, Sarasota, FL 34239

  Pre-Construction. To be built. Nestled within the heart of West of the Trail lies a world-class estate proudly standing as the pinnacle of future luxury homes. Collectively envisioned by the esteemed team of M&J Pham Development, the residence is a masterwork of inspiring design and immaculate execution. Situated on a majestic parcel of approximately 15,930 sqft, the home promises an unrivaled

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  1800 Webber St, Sarasota, FL 34239
• 

  

  

  /36

  Est $1,767,466 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,841 Sq Ft

  1744 Fortuna St, Sarasota, FL 34239

  1744 Fortuna St, Sarasota, FL 34239
• 

  

  

  /45

  $3,690,000

  • 5 Beds
  • 4.5 Baths
  • 3,478 Sq Ft

  2174 Mcclellan Pkwy, Sarasota, FL 34239

  Enjoy complete peace of mind with a FIRST FLOOR ELEVATION of 20.' FT ABOVE SEA LEVEL & AVERAGE GRADE AT RESIDENCE at 18'. *NO HURRICANE DAMAGE* This stunning custom-built, coastal contemporary WEST OF TRAIL residence in McClellan Park is a true gem! Completed in June 2022, this spacious residence features 5 bedrooms, 4.5 baths, and an in-home elevator, offering comfort and convenience across two

  

  Mary Dickey

  BARCLAYS REAL ESTATE GROUP 1

  (941) 206-7527

  2174 Mcclellan Pkwy, Sarasota, FL 34239
• 

  

  /19

  $4,900 per month

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • House for Rent

  3521 Almeria Ave, Sarasota, FL 34239

  Great condition, Great location 1 mile to beach, Great school district,Fully Furnished

  3521 Almeria Ave, Sarasota, FL 34239
• 

  /2

  $900,000 Sold Jul 24, 2025

  • 2,529 Sq Ft
  • $356/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1956

  3705 Tangier Terrace, Sarasota, FL 34239

  **Mid-Century Modern Charm in San Remo – Prime Location & Endless Potential**Discover this **mid-century modern 3-bedroom, 2.5-bath ranch** in the sought-after **San Remo Estates**. Set on a lush **1/3-acre lot West of the Trail**, this home is just minutes from **Siesta Key Beach, Morton’s Market, CineBistro, the Farmers Market, and Downtown Sarasota’s dining, shopping, and cultural

  Grace Bonaccorso FINE PROPERTIES

  3705 Tangier Terrace, Sarasota, FL 34239
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  /10

  Est $223,299 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 991 Sq Ft

  3700 S Osprey Ave Unit 210, Sarasota, FL 34239

  3700 S Osprey Ave Unit 210, Sarasota, FL 34239
• 

  

  /45

  $3,690,000

  • 5 Beds
  • 4.5 Baths
  • 3,478 Sq Ft

  2174 Mcclellan Pkwy, Sarasota, FL 34239

  Enjoy complete peace of mind with a FIRST FLOOR ELEVATION of 20.' FT ABOVE SEA LEVEL & AVERAGE GRADE AT RESIDENCE at 18'. *NO HURRICANE DAMAGE* This stunning custom-built, coastal contemporary WEST OF TRAIL residence in McClellan Park is a true gem! Completed in June 2022, this spacious residence features 5 bedrooms, 4.5 baths, and an in-home elevator, offering comfort and convenience across two

  

  Mary Dickey

  Barclays Real Estate Group 1

  (941) 206-6993

  2174 Mcclellan Pkwy, Sarasota, FL 34239
• 

  

  /12

  $1,390 per month

  • 1 Bed
  • 1 Bath
  • 552 Sq Ft
  • Apartment for Rent

  1739 Siesta Dr, Sarasota, FL 34239

  Tucked away in a charming, Florida-style building with only four units, this second floor residence offers an unbeatable location in the coveted Cherokee Park neighborhood. Less than 1/2 mile to the North Siesta Key Bridge, you're minutes from the beach, dining, and shopping. Enjoy your morning coffee and the evening breeze on the screened lanai. Flat screen television, kitchen stocked with

  Margot Vigar (Leonard) COLDWELL BANKER REALTY

  1739 Siesta Dr, Sarasota, FL 34239
• 

  /2

  $2,224,500 Sold Jul 18, 2025

  • 3,584 Sq Ft
  • $621/SF
  • 28 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2013

  1813 Boyce St, Sarasota, FL 34239

  Tuscan-Inspired Luxury - Tucked away in the coveted West of the Trail neighborhood of Hartsdale and just moments from the charm of Southside Village, this Tuscan-inspired home offers refined elegance and timeless design. Custom-built and residing on an expansive double lot, this 4 bedroom/3.5 bathroom pool home offers a rare combination of luxury, privacy, and convenience in one of Sarasota’s

  Lindsey Nussbaum COLDWELL BANKER REALTY

  1813 Boyce St, Sarasota, FL 34239
• 

  

  /100

  Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 4,871 Sq Ft

  1705 Wisconsin Ln, Sarasota, FL 34239

  1705 Wisconsin Ln, Sarasota, FL 34239
• 

  

  /67

  $3,699,000

  • 3 Beds
  • 3.5 Baths
  • 3,136 Sq Ft

  1547 Sandpiper Ln, Sarasota, FL 34239

  This one-of-a-kind, fully renovated residence is nestled in the heart of Sarasota’s historic McClellan Park—just steps from the bayfront, downtown, and Southside Village. Originally built by a well-known builder as his personal home and reimagined in 2022 by the previous owner, an interior designer, the property showcases timeless elegance, custom finishes, and exceptional privacy. Beyond

  Marlin Yoder HARRY ROBBINS ASSOC INC

  1547 Sandpiper Ln, Sarasota, FL 34239
• 

  

  /22

  $1,650 per month

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  1662 Fortuna St Unit 1662 Fortuna St Sarasota, Sarasota, FL 34239

  Pet friendly! All utilities included. Close to everything!

  1662 Fortuna St Unit 1662 Fortuna St Sarasota, Sarasota, FL 34239
• 

  /2

  $1,550,000 Sold Jul 15, 2025

  • 2,763 Sq Ft
  • $561/SF
  • 131 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1946

  1954 Datura St, Sarasota, FL 34239

  This exceptional single-story home in the highly sought-after West of the Trail neighborhood offers the perfect blend of charm, privacy, and convenience. Ideally located near downtown Sarasota, top-rated schools, and world-renowned beaches, this property is an entertainer’s dream and a tranquil wellness retreat. The home features 3 bedrooms, 2.5 baths, and a dedicated den with serene views of the

  Bev Murray BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

  1954 Datura St, Sarasota, FL 34239
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  /10

  Est $3,692,975 Not Listed For Sale

  1615 N Lodge Dr, Sarasota, FL 34239

  1615 N Lodge Dr, Sarasota, FL 34239
• 

  

  /28

  $589,000

  • 3 Beds
  • 2 Baths
  • 1,397 Sq Ft

  2110 Goldenrod St, Sarasota, FL 34239

  Right Where You Want to Be—With a Pool That’s Ready to Dive Into! Att:Investors - ARBNB Income is $75,000This well-cared-for gem is all about location and lifestyle. New Roof in 2025 and New Pool Heater in 2024. Tucked into the private, dead-end street but just minutes to Siesta Key Beach, the Village, Sarasota Memorial, and loads of great local spots—you’ll feel right at home and right

  Steven Weiss REDFIN CORPORATION

  2110 Goldenrod St, Sarasota, FL 34239
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  /16

  $1,595 per month

  • 2 Beds
  • 1 Bath
  • 991 Sq Ft
  • Condo for Rent

  3700 S Osprey Ave Unit 204, Sarasota, FL 34239

  Spacious 2-Bedroom Condo in Prime Sarasota Location – Walk to The Bay!Welcome to Unit 204 at 3700 S Osprey Ave – a beautifully updated 2-bedroom, 1-bathroom condo nestled in the heart of Sarasota’s desirable Southside Village neighborhood. Just minutes from Siesta Key Beach, downtown Sarasota, and within walking distance to shops, restaurants, and the scenic waterfront, this location is ideal

  Michael Sorensen STRINGER MANAGEMENT INC

  3700 S Osprey Ave Unit 204, Sarasota, FL 34239
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  /2

  $3,800,000 Sold Jul 10, 2025

  • 5,660 Sq Ft
  • $671/SF
  • 5 Days On Market

  • 4 Beds
  • 7 Baths
  • Built 2013

  1910 Datura St, Sarasota, FL 34239

  West of Trail! Custom Build by Voight Construction. Nestled in one of Sarasota’s most coveted neighborhoods, this exceptional custom estate spans over three expansive lots and boasts craftsmanship that is truly one-of-a-kind. A celebration of fine design, this home features intricate millwork, rich stained oak floors, and soaring ceilings adorned with stunning pecky cypress inlays.Step

  Kelly Gettel COLDWELL BANKER REALTY

  1910 Datura St, Sarasota, FL 34239
• 

  

  /3

  Est $1,611,449 Not Listed For Sale

  • 3 Beds

  1700 Seminole Dr, Sarasota, FL 34239

  1700 Seminole Dr, Sarasota, FL 34239
• 

  

  /69

  $2,171,000

  • 4 Beds
  • 4.5 Baths
  • 3,554 Sq Ft

  3319 S Osprey Ave, Sarasota, FL 34239

  Motivated Seller – bring your offers! Just Added a $150K Custom Pool & Spa! Live the ultimate Florida lifestyle in this luxury new construction home (2023) by acclaimed builder M&J Pham Development, located between Siesta Key and Downtown Sarasota in the highly sought-after Southside School District. This elegant 4-bedroom, 4.5-bathroom residence blends upscale design with modern comfort and

  Laura Rode KELLER WILLIAMS ON THE WATER S

  3319 S Osprey Ave, Sarasota, FL 34239
• 

  

  /54

  $13,000 per month

  • 4 Beds
  • 4 Baths
  • 3,176 Sq Ft
  • House for Rent

  1905 Goldenrod St, Sarasota, FL 34239

  LOCATION, LOCATION, LOCATION. Stunning turnkey furnished single family home available to rent in the sought after community of Poinsettia Park of Sarasota. This West of the Trail, 2020 build, Classic Homes by Clayton Inc., property is energy-efficient, elegant, beautifully furnished, and well appointed. Pulling up to the home you immediately notice the professional landscaping and lighting with

  C. Alison Hunter JENNETTE PROPERTIES INC

  1905 Goldenrod St, Sarasota, FL 34239
• 

  /2

  $800,000 Sold Jun 27, 2025

  • 1,786 Sq Ft
  • $448/SF
  • 30 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  1857 Jasmine Dr, Sarasota, FL 34239

  BEST LOCATION! ***WEST OF THE TRAIL***Wonderful home, beautifully renovated and ready to move in.*The open floor plan and huge fenced backyard will delight you! Bring your pets and your outdoor grill, gardening skills and enjoy this oasis*. The custom kitchen is equipped with KITCHEN AID stainless steel appliances, huge island and breakfast bar. Plantation shutters. Tile throughout the home.

  Livya Hament PREFERRED SHORE LLC

  1857 Jasmine Dr, Sarasota, FL 34239
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  /4

  Est $4,196,723 Not Listed For Sale

  2100 McClellen Pkwy, Sarasota, FL 34239

  2100 McClellen Pkwy, Sarasota, FL 34239
• 

  

  /71

  $4,950,000

  • 5 Beds
  • 7 Baths
  • 6,128 Sq Ft

  1686 North Dr, Sarasota, FL 34239

  Welcome to this stunning 2021-built home in one of Sarasota’s most iconic and picturesque historic neighborhoods, Cherokee Park. Offering luxurious living with thoughtful design, this spacious residence of over 6000 square feet features a desirable first-floor primary suite with a decadent bathroom with soaking tub, oversized marble shower, and access to the covered porch for your morning coffee.

  Samantha Callaway RE/MAX ALLIANCE GROUP

  1686 North Dr, Sarasota, FL 34239
• 

  

  /23

  $8,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,539 Sq Ft
  • House for Rent

  1638 South Dr, Sarasota, FL 34239

  FULLY REMODELED 4 BEDROOM GREAT FAMILY HOME. NO POOL LESS EXPENSES. NO SHORT TERM RENTAL. A MUST SEE IF YOU LIKE RANCH STYLE. ALL NEW - HVAC - ELECTRIC - WINDOWS - KITCHEN - BATHS - ROOF. NOTHING MISSED ON THIS VERY ATTRACTIVE HOME IN CHEROKEE PARK, SOUTH SIDE SCHOOL AND THE HOSPITAL CORE.

  Ryan Ackerman COLDWELL BANKER REALTY

  1638 South Dr, Sarasota, FL 34239
• 

  /2

  $9,500,000 Sold Jun 09, 2025

  • 5,932 Sq Ft
  • $1601/SF
  • 373 Days On Market

  • 3 Beds
  • 5 Baths
  • Built 2014

  3336 Old Oak Dr, Sarasota, FL 34239

  Nestled within the vibrant city of Sarasota, Florida, this exquisite estate offers an unparalleled blend of luxury, privacy, and natural beauty. Situated on a sprawling 2-acre parcel of prime bayfront land, this custom-built residence boasts panoramic views of the shimmering waters, ensuring breathtaking sunsets year-round. As you enter through the gated entrance, you are greeted by meticulously

  Thomas Cail RE/MAX ALLIANCE GROUP

  3336 Old Oak Dr, Sarasota, FL 34239
• 

  

  /15

  Est $1,862,872 Not Listed For Sale

  • 4 Beds

  0 Jacinto Ct, Sarasota, FL 34239

  0 Jacinto Ct, Sarasota, FL 34239
• 

  

  /33

  $1,150,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,013 Sq Ft

  1926 Morris St, Sarasota, FL 34239

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Rare West of the Trail home! Discover the perfect blend of vintage charm and modern convenience in this delightful home with an attached garage on a double lot. Known for its prime location, this home is ideally positioned between the world renowned Siesta Key beaches and minutes to the vibrant cultural hub of

  Tracy Seider RE/MAX ALLIANCE GROUP

  1926 Morris St, Sarasota, FL 34239
• 

  

  /17

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 991 Sq Ft
  • Condo for Rent

  3700 S Osprey Ave Unit 216, Sarasota, FL 34239

  WEST OF THE TRAIL...this charming 2nd floor condo offers 2 bedrooms and 1 bathroom. The balcony is enclosed with screens and windows. Excellent location, convenience is key with this property. Situated just around the corner from the north bridge and minutes away from the world renowned SIESTA KEY BEACH. Live the best of both worlds in a peaceful, quiet area and easy access to coastal living.

  Teresa Ribaudo JENNETTE PROPERTIES INC

  3700 S Osprey Ave Unit 216, Sarasota, FL 34239
• 

  /2

  $4,450,000 Sold Jun 02, 2025

  • 5,160 Sq Ft
  • $862/SF
  • 211 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2006

  1502 Siesta Dr, Sarasota, FL 34239

  Welcome to this captivating property located in the beautiful San Remo Estates and minutes away from Siesta Key Beaches and downtown Sarasota. This house is located in an incredible location so close in proximity to great schools, restaurants, cultural destinations, and parks. This 5,160 SqFt waterfront property is nestled on a 18,416 SqFt lot behind a private gate. As you enter the front

  Samantha Jennen PREFERRED SHORE LLC

  1502 Siesta Dr, Sarasota, FL 34239
• 

  

  /11

  Not Listed For Sale

  • 4 Beds
  • 7 Baths
  • 6,428 Sq Ft

  3300 Old Oak Dr, Sarasota, FL 34239

  3300 Old Oak Dr, Sarasota, FL 34239
• 

  

  /60

  $1,925,000

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft

  1857 Tulip Dr, Sarasota, FL 34239

  Modern luxury meets Florida beach house style in this impeccably renovated residence, located in the highly sought-after “West of the Trail” enclave — just minutes from Siesta Key’s world-renowned beaches and Downtown Sarasota’s cultural district.This designer 3-bedroom, 2-bath home offers nearly 1,900 square feet of refined interior space, thoughtfully reimagined for both elegant living

  Ralf Michael Guensch EXP REALTY LLC

  1857 Tulip Dr, Sarasota, FL 34239
• 

  

  /36

  $4,500 per month

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • House for Rent

  3414 Old Oak Dr, Sarasota, FL 34239

  Available now for LEASE Annually/Monthly UNFURNISHED POOL HOME. Sarasota's most requested location, a "West of the Trail" neighborhood. This charming Florida style ranch home is located right off the north bridge entry to SIESTA KEY. Welcome to your private tropical retreat in Sarasota! This beautifully updated 3-bedroom, 2-bathroom home is available now and ready for you to MOVE-IN. The great

  Patrice Ivan WAGNER REALTY

  3414 Old Oak Dr, Sarasota, FL 34239
• 

  /2

  $1,250,000 Sold May 30, 2025

  • 2,162 Sq Ft
  • $578/SF
  • 416 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1948

  3800 Flores Ave, Sarasota, FL 34239

  This location in the Granada neighborhood is perfect for your future home! Rental potential or build your Estate-Sized Sarasota home on this 10,485 sq. ft. lot with room for pool! This West of the Trail property offers a peaceful retreat with its spacious lot and beautiful mature trees with no deed restrictions! It is near newer homes on estate size lot side of Flores (minimum 100' of frontage),

  Solveiga Spalvins LPT REALTY LLC

  3800 Flores Ave, Sarasota, FL 34239
• 

  

  /56

  Est $2,118,630 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,576 Sq Ft

  1715 Bonita Ct, Sarasota, FL 34239

  1715 Bonita Ct, Sarasota, FL 34239
• 

  

  /67

  $2,185,000

  • 4 Beds
  • 3 Baths
  • 2,307 Sq Ft

  1864 Goldenrod St, Sarasota, FL 34239

  GREAT LOCATION – WEST OF THE TRAIL! This dazzling custom-built, single-level pool home is situated in the desirable "flower streets”, west of the trail in Sarasota. Featuring a new, 3 color clay tile roof and Mediterranean style design this home has timeless style combined with modern luxury. Upon entering the double doors of this one-story retreat, you will notice the open layout and quality

  Jan Jordan BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  1864 Goldenrod St, Sarasota, FL 34239
• 

  

  /57

  $15,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,519 Sq Ft
  • House for Rent

  1725 Bonita Ct, Sarasota, FL 34239

  This MAGNIFICENT home is nestled away in the Historic Granada private neighborhood with easy access to all amenities. 4 Bedrooms 3.5 Baths and over 3500+ square feet of elegantly finished living areas. Authentic travertine tile and maple hardwood floors, volume ceilings, solid-wood cabinetry, two-sided fireplace, chef’s kitchen, three-car garage (owner uses one bay) and cypress wood exterior

  Teresa Ribaudo JENNETTE PROPERTIES INC

  1725 Bonita Ct, Sarasota, FL 34239
• 

  /2

  $1,050,000 Sold May 16, 2025

  • 3,121 Sq Ft
  • $336/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2002

  1904 Hyde Park St, Sarasota, FL 34239

  Move In Ready! This updated West of the Trail home has been recently given a make over with fresh paint, new carpets and more! A charming custom home ideally located just a gentle stroll away from Morton’s Market and the exclusive Southside Village. Beautifully appointed both inside and out with an inviting courtyard and fenced yard. Master Bedroom is located on the ground level, boasts a dream

  Lisa Warren OWN SRQ LLC

  1904 Hyde Park St, Sarasota, FL 34239
• 

  

  /37

  Est $4,172,626 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,538 Sq Ft

  1739 Cherokee Dr, Sarasota, FL 34239

  1739 Cherokee Dr, Sarasota, FL 34239

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