Siesta Key, FL Homes

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  $3,599,000

  • 4 Beds
  • 5 Baths
  • 4,194 Sq Ft

  611 Tremont St, Sarasota, FL 34242

  A spectacular offering on one of Siesta Key’s most coveted streets, this stunning canal-front residence on Tremont Street represents a truly special opportunity to own a home that seamlessly blends boating, timeless island charm, and refined coastal living. Tucked beneath mature trees in a quiet, established enclave known for its old Siesta character, the property offers private canal frontage

  Mike Warm PREMIER SOTHEBY'S INTERNATIONAL REALTY

  611 Tremont St, Sarasota, FL 34242
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  $5,000 per month

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • House for Rent

  735 Birdsong Ln, Sarasota, FL 34242

  Looking for the ultimate Siesta Key getaway? This stunning 3-bedroom, 2-bath home offers everything you need for a dream vacation, just 1 mile from the famous Siesta Key Beach and a quick bike ride to the lively Siesta Key Village! Available Nov 1-Dec 21, 2025, and May 1-Nov 21, 2026. 30 day minimum stay, NOT available annually. Fully turnkey furnished, this home is ready to welcome you the

  Scott Nold TNG PROPERTY MANAGEMENT

  735 Birdsong Ln, Sarasota, FL 34242
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  $650,000 Sold Dec 29, 2025

  1093 Lake House Cir Unit C205, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $481/SF
  • 38 Days On Market

  Last Listing Agent Pamela Wall MICHAEL SAUNDERS & COMPANY

  1093 Lake House Cir Unit C205, Sarasota, FL 34242
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  Est $1,140,821 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,915 Sq Ft

  1240 Dolphin Bay Way Unit 303, Sarasota, FL 34242

  1240 Dolphin Bay Way Unit 303, Sarasota, FL 34242
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  $1,300,000

  • 2 Beds
  • 2 Baths
  • 1,214 Sq Ft

  6342 Midnight Pass Rd Unit 423, Sarasota, FL 34242

  Experience effortless beachfront living from this turnkey-furnished, second-floor condominium with elevator access and sweeping views of the turquoise waters of the Gulf of Mexico and the newly updated pool area. Enjoy morning coffee to the sound of the surf and spectacular sunsets with uninterrupted shoreline views. BEST OF ALL - THIS UNIT SUSTAINED NO HURRICANE DAMAGE! Located at Midnight Cove,

  Jan Jordan BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  6342 Midnight Pass Rd Unit 423, Sarasota, FL 34242
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  $10,500 per month

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft
  • Condo for Rent

  5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242

  Welcome to your perfect Siesta Key getaway! This beautifully updated 2-bedroom, 2-bath end-unit condo in the Palm Bay Club offers stunning bay views, a bright, open interior, and resort-style amenities—just steps from the Bayfront pool.At 1,270 sq. ft., this is one of the largest condos in Palm Bay. You'll love the driftwood-style cabinetry, quartz countertops, and stainless steel appliances

  Robert Bevington SHOWTIME REALTY

  5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
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  $962,500 Sold Oct 03, 2025

  5750 Midnight Pass Rd Unit 203, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,335 Sq Ft
  • Built 1984

  Last Sold Summary

  • 12% Below List Price
  • $721/SF
  • 86 Days On Market

  Current Estimated Value $975,873

  Last Listing Agent Brian Livesey WATERSIDE REALTY LLC

  5750 Midnight Pass Rd Unit 203, Sarasota, FL 34242
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  Est $1,298,524 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,740 Sq Ft

  5319 Siesta Cove Dr, Sarasota, FL 34242

  5319 Siesta Cove Dr, Sarasota, FL 34242
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  $643,000 Open House 7/02

  • 2 Beds
  • 2 Baths
  • 1,306 Sq Ft

  6285 Midnight Pass Rd Unit 403, Sarasota, FL 34242

  Tremendous value for this 4th floor condo for sale at the Excelsior Beach to Bay Complex! Coveted for its soaring ceilings and the opportunity to add a bona fide 3rd bedroom, you can redesign this bayside penthouse into a luxurious home/home away from home. Take your time as there have been updates, it's in great condition and quite lovely as is. This particular unit faces south and is filled

  Joan Winters EXIT KING REALTY

  6285 Midnight Pass Rd Unit 403, Sarasota, FL 34242
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  $8,500 per month

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft
  • Condo for Rent

  1221 Siesta Bayside Dr Unit 1221A, Sarasota, FL 34242

  Beautifully turnkey furnished 2-bedroom, 2-bathroom, ground-floor condo available for monthly rent in a gated, resort-style community on Siesta Key. Just a short 5-minute walk to private access at world-famous Siesta Key Beach, known for its fine quartz sand and turquoise waters. This tropical retreat features a spacious open-concept layout, a fully equipped kitchen, in-unit laundry, private

  Sinan Turkomer BROKER & BAKER INTERNATIONAL REALTY

  1221 Siesta Bayside Dr Unit 1221A, Sarasota, FL 34242
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  $1,640,000 Sold Sep 12, 2025

  4831 Primrose Path, Sarasota, FL 34242

  • 4 Beds
  • 7 Baths
  • 3,893 Sq Ft
  • Built 1964

  Last Sold Summary

  • 9% Below List Price
  • $421/SF
  • 31 Days On Market

  Current Estimated Value $1,611,304

  Last Listing Agent Derek Edwards KELLER WILLIAMS ON THE WATER S

  4831 Primrose Path, Sarasota, FL 34242
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  /47

  Est $447,651 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  6006 Midnight Pass Rd Unit 56, Sarasota, FL 34242

  6006 Midnight Pass Rd Unit 56, Sarasota, FL 34242
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  /26

  $8,900,000

  • Land
  • 1.2 Acres
  • $7,416,667 per Acre

  4105 Shell Rd, Sarasota, FL 34242

  Siesta Key North end with 140+ feet of panoramic views. Seawall and rip wrap secured Gulf Front estate parcel. Discover a rare opportunity on Sarasota's coveted "Gold Coast" with this expansive Gulf-front property. Spanning 52,121 square feet with 141 feet of direct Gulf frontage, this lot provides the perfect canvas for your custom waterfront home. Enjoy unobstructed, sweeping vistas and

  Michael Hays MICHAEL SAUNDERS & COMPANY

  4105 Shell Rd, Sarasota, FL 34242
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  /53

  $5,000 per month

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

  6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242

  Beachfront Bliss at Casa Mar – Siesta KeyDreaming of a Siesta Key getaway? Welcome to Unit 15 at Casa Mar, a charming 1BR/1BA beachfront condo that offers the perfect mix of relaxation and resort-style fun.Step outside and enjoy exclusive access to Casa Mar’s private stretch of quartz-white sand, complete with lounge chairs for sunbathing and unforgettable Gulf views. Cool off with a swim

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242
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  $2,000,000 Sold Dec 19, 2025

  3925 Hamilton Club Cir Unit 7, Sarasota, FL 34242

  • 3 Beds
  • 3.5 Baths
  • 2,884 Sq Ft
  • Built 1994

  Last Sold Summary

  • 13% Below List Price
  • $693/SF
  • 51 Days On Market

  Last Listing Agent Barbara Dumbaugh MICHAEL SAUNDERS & COMPANY

  3925 Hamilton Club Cir Unit 7, Sarasota, FL 34242
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  Est $480,634 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  5673 Midnight Pass Rd Unit 201, Sarasota, FL 34242

  5673 Midnight Pass Rd Unit 201, Sarasota, FL 34242
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  $2,150,000

  • Land
  • 0.58 Acre
  • $3,706,897 per Acre

  0 Ocean Blvd, Sarasota, FL 34242

  Rare Canal-Front Opportunity on Siesta Key – Last Available Raw Land Parcels. Don’t miss the final two canal-front parcels on Siesta Key, exclusively offered as a package to one buyer. These gorgeous lots can be kept as individual 1⁄4+ acre parcels or combined into a single 1⁄2-acre estate. Build your dream home on the serene, tree-lined canal-front lot and develop the front lot as a

  Lisa Shepard BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  0 Ocean Blvd, Sarasota, FL 34242
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  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft
  • Condo for Rent

  1215 S Portofino Dr Unit 202, Sarasota, FL 34242

  BEAUTIFUL WATERFRONT CONDO ON SIESTA KEY AVAILABLE NOW AND the month of January! CANAL VIEW • BEACH ACCESS • BOAT SLIPS UPON AVAILABILITY - REASONABLY PRICED. Now available In Season and as an annual Rental! Private, beautifully furnished condo with a gorgeous view of the Harbor and Sailboat Water Canal in Siesta Harbor. Enjoy water views of the canal from your enclosed balcony and just a

  Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

  1215 S Portofino Dr Unit 202, Sarasota, FL 34242
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  $1,520,000 Sold Sep 02, 2025

  4408 Midnight Pass Rd, Sarasota, FL 34242

  • 4 Beds
  • 3.5 Baths
  • 2,611 Sq Ft
  • Built 1951

  Last Sold Summary

  • 10% Below List Price
  • $582/SF
  • 124 Days On Market

  Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

  4408 Midnight Pass Rd, Sarasota, FL 34242
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  Est $674,201 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  105 Whispering Sands Dr Unit V48, Sarasota, FL 34242

  105 Whispering Sands Dr Unit V48, Sarasota, FL 34242
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  /75

  $599,000

  • 2 Beds
  • 2.5 Baths
  • 1,332 Sq Ft

  6157 Midnight Pass Rd Unit B12, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. A true SIESTA KEY DIAMOND IN THE ROUGH, this rare waterfront residence offers what may be the most breathtaking Sarasota Bay intracoastal view in the entire Bay Oaks community—a view that feels endless, cinematic, and utterly transformative. Positioned directly on the water, this second-floor, two-level, two-bedroom, two-and-a-half-bath condo is a

  Jessica Burdick LOYD ROBBINS & CO. LLC

  6157 Midnight Pass Rd Unit B12, Sarasota, FL 34242
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  $15,000 per month

  • 3 Beds
  • 3 Baths
  • 1,898 Sq Ft
  • Condo for Rent

  22 Sandy Cove Rd Unit 10-5, Sarasota, FL 34242

  RATES AND AVAILABILITY VARY. AVAILABLE SEASON 2026! Welcome to a completely renovated, light-filled penthouse in the exclusive Sandy Cove community — where coastal design meets breathtaking Gulf views in every direction. This professionally managed 3-bedroom, 3-bath residence is fully turnkey furnished and thoughtfully designed for relaxed, upscale living.Every inch of the home has been

  Cole Collins COLDWELL BANKER REALTY

  22 Sandy Cove Rd Unit 10-5, Sarasota, FL 34242
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  $1,577,000 Sold Dec 04, 2025

  5164 Windward Ave, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,972 Sq Ft
  • Built 1974

  Last Sold Summary

  • 12% Below List Price
  • $800/SF
  • 92 Days On Market

  Last Listing Agent Taylor Thompson WILLIAM RAVEIS REAL ESTATE

  5164 Windward Ave, Sarasota, FL 34242
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  Est $1,054,983 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,320 Sq Ft

  115 Sand Dollar Ln, Sarasota, FL 34242

  115 Sand Dollar Ln, Sarasota, FL 34242
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  $3,775,000

  • 4 Beds
  • 4 Baths
  • 3,788 Sq Ft

  3939 Higel Ave, Sarasota, FL 34242

  Set on the north end of Siesta Key, this striking modernist residence offers the rare balance of island serenity and seamless access to the mainland, placing vibrant downtown Sarasota, Southside Village, and the area’s cultural and dining destinations just minutes away—while the azure waters of the Gulf of Mexico and Siesta Key’s world-famous white quartz sand beach are equally close at

  Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3939 Higel Ave, Sarasota, FL 34242
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  $14,000 per month

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • House for Rent

  211 Island Cir, Sarasota, FL 34242

  AVAILABLE for 2026... Jan., Feb and April Fantastic pool home located .4 mile from Siesta Beach access! Enjoy this completely renovated 3 bedroom / 2bath pool home in Palm Island on Siesta Key. With comfort in mind, vacation memories are waiting to be made here! All furnishings, appliances and flooring are new and decorated in coastal colors. Enjoy a morning walk to the powdery sand beach less

  Brenda Cozy COLDWELL BANKER REALTY

  211 Island Cir, Sarasota, FL 34242
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  $735,000 Sold Nov 05, 2025

  717 Treasure Boat Way, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,978 Sq Ft
  • Built 1973

  Last Sold Summary

  • 18% Below List Price
  • $372/SF
  • 175 Days On Market

  Last Listing Agent Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  717 Treasure Boat Way, Sarasota, FL 34242
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  Est $995,464 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,103 Sq Ft

  1033 Shadow Lawn Way, Sarasota, FL 34242

  1033 Shadow Lawn Way, Sarasota, FL 34242
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  $999,000

  • 2 Beds
  • 2 Baths
  • 852 Sq Ft

  6342 Midnight Pass Rd Unit 212, Sarasota, FL 34242

  Nestled in the sought-after MIDNIGHT COVE community on the beachside of Siesta Key, this charming condominium offers the perfect blend of beachfront living and modern convenience. BEST NEWS OF ALL - - NO HURRICANE DAMAGE, WATER OR SAND IN THIS UNIT! Experience effortless beachfront living from this turnkey-furnished retreat, positioned on the GROUND FLOOR, offering a rare walk-out patio that

  Jan Jordan BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  6342 Midnight Pass Rd Unit 212, Sarasota, FL 34242
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  $14,000 per month

  • 4 Beds
  • 3 Baths
  • 2,450 Sq Ft
  • House for Rent

  4879 Commonwealth Dr, Sarasota, FL 34242

  Lease a Rare Piece of Sarasota's Architectural History on Siesta Key! Step into timeless design and architectural significance with this rare mid-century modern masterpiece, situated on a private double lot in the heart of Siesta Key. Originally crafted in 1957 by Frank Coleman and Tollen Twitchell, two influential figures in the Original Sarasota School of Architecture, this home seamlessly

  Daniel Petrilla PREFERRED SHORE LLC

  4879 Commonwealth Dr, Sarasota, FL 34242
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  $800,000 Sold Jul 11, 2025

  5522 Calle Del Verano, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,358 Sq Ft
  • Built 1956

  Last Sold Summary

  • 16% Below List Price
  • $589/SF
  • 16 Days On Market

  Current Estimated Value $792,030

  Last Listing Agent Mary Kassen PREFERRED SHORE LLC

  5522 Calle Del Verano, Sarasota, FL 34242
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  Est $2,839,750 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,647 Sq Ft

  850 Siesta Key Cir, Sarasota, FL 34242

  850 Siesta Key Cir, Sarasota, FL 34242
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  /75

  $1,450,000

  • 3 Beds
  • 2 Baths
  • 1,854 Sq Ft

  5880 Midnight Pass Rd Unit 210, Sarasota, FL 34242

  WHY Should I Consider Casarina? Because this is one of those RARE moments when Buyers can step into a fully modernized community on Siesta Key. It should actually be called "Casarina 2.0" since all the major decisions, major projects, and major disruptions are behind them—including the assessments! Which means today’s lucky buyer is going to enjoy modernized systems, refreshed amenities, and

  Christa Spalding COLDWELL BANKER REALTY

  5880 Midnight Pass Rd Unit 210, Sarasota, FL 34242
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  $3,500 per month

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft
  • Condo for Rent

  1700 Cove II Place Unit 310, Sarasota, FL 34242

  Available 3500.00 Monthly - September 17th 2026 through December 31st 2026... Available January 2026 - 5,000.00 May be rented weekly. l – Stunning Water Views & Deeded Beach Access | Siesta Keyplus taxes and fees. Welcome to your perfect beach getaway! This 2-bedroom, 1.5-bath condo in Midnight Cove II offers breathtaking water views from both the unit and the spacious patio, along with

  Robert Bevington SHOWTIME REALTY

  1700 Cove II Place Unit 310, Sarasota, FL 34242
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  $1,970,000 Sold Jun 27, 2025

  5966 Midnight Pass Rd Unit G-51 & G-58, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 2,088 Sq Ft
  • Built 1970

  Last Sold Summary

  • 6% Below List Price
  • $943/SF
  • 7 Days On Market

  Current Estimated Value $1,949,230

  Last Listing Agent Carolyn Donnelly COLDWELL BANKER REALTY

  5966 Midnight Pass Rd Unit G-51 & G-58, Sarasota, FL 34242
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  Est $1,285,664 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,206 Sq Ft

  5125 Oakmont Place, Sarasota, FL 34242

  5125 Oakmont Place, Sarasota, FL 34242
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  $475,000

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  6157 Midnight Pass Rd Unit E23, Sarasota, FL 34242

  Live the Siesta Key lifestyle — right across the street from world-famous SIESTA BEACH—with the added bonus of SHORT-TERM rental / AIRBNB use for maximum flexibility and income potential 1-week rentals allowed and a rental program already in place). This RENOVATED condo is offered FULLY FURNISHED and turnkey, making it easy to enjoy immediately or start generating rental revenue from day one.

  Kathy VanDorne PREFERRED SHORE LLC

  6157 Midnight Pass Rd Unit E23, Sarasota, FL 34242
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  $5,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • House for Rent

  4946 Commonwealth Dr, Sarasota, FL 34242

  Short Term Rental-Not available January-April of 2026 Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key canal. From the moment you arrive, you'll feel the world melt away as you step into this ultimate beach house getaway designed for relaxation and fun. Imagine sipping your morning coffee on the private

  Beth Dilley ASCENDIA REAL ESTATE

  4946 Commonwealth Dr, Sarasota, FL 34242
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  $1,050,000 Sold Dec 16, 2025

  460 Beach Rd Unit B2, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,363 Sq Ft
  • Built 1980

  Last Sold Summary

  • 12% Below List Price
  • $770/SF
  • 105 Days On Market

  Last Listing Agent Tamatha Spangler NORTHGROUP REAL ESTATE, INC

  460 Beach Rd Unit B2, Sarasota, FL 34242
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  Est $2,191,656 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,753 Sq Ft

  5223 Calle Menorca, Sarasota, FL 34242

  5223 Calle Menorca, Sarasota, FL 34242

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