Siesta Key, FL Homes

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  $3,675,000

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

  3939 Higel Ave, Sarasota, FL 34242

  Now Offered At a Refined Price — Modern Siesta Key Living. 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

  Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3939 Higel Ave, Sarasota, FL 34242
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  $8,000 Per Month

  • 3 Beds
  • 3 Baths
  • 1,835 Sq Ft
  • Condo for Rent

  1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242

  Welcome to luxury living at its finest in this exquisite 3-bedroom, 2-bathroom condo situated in the prestigious Gulf and Bay Club Bayside.Perched on the second story, this residence offers unparalleled bay-front views that will take your breath away. The open-concept living space seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere bathed in natural

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
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  $1,081,500 Sold Mar 27, 2026

  5502 Shadow Lawn Dr, Sarasota, FL 34242

  • 3 Beds
  • 4 Baths
  • 2,337 Sq Ft
  • Built 1961

  Last Sold Summary

  • 23% Below List Price
  • $463/SF
  • 261 Days On Market

  Current Estimated Value $1,312,407

  Last Listing Agent Dan Miller PREFERRED SHORE LLC

  5502 Shadow Lawn Dr, Sarasota, FL 34242
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  Est $1,567,941 Not Listed For Sale

  4926 Commonwealth Dr, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • Built 1987

  4926 Commonwealth Dr, Sarasota, FL 34242

  Last Sold Summary

  • 19% Below List Price
  • $978/SF
  • 1 Day On Market

  • Last Sold Price $1,925,000
  • Jan 31, 2024

  Last Listing Agent Karen Nasello EXP REALTY LLC
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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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  $6,972 Per Month

  • 1 Bed
  • 1 Bath
  • 672 Sq Ft
  • House for Rent

  6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242

  New photos coming soon! Villa 36 at Aloha Kai is perfectly situated on Siesta Key, a popular barrier island on Florida’s West Coast. Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key ranks among Florida’s top vacation

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242
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  $1,450,000 Sold Jun 23, 2025

  420 Beach Rd Unit 502, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1980

  Last Sold Summary

  • 18% Below List Price
  • $1,102/SF
  • 56 Days On Market

  Current Estimated Value $1,399,175

  Last Listing Agent Anthony Dalesandro BRIGHT REALTY

  420 Beach Rd Unit 502, Sarasota, FL 34242
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  Est $747,765 Not Listed For Sale

  1200 E Peppertree Ln Unit 407, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,460 Sq Ft
  • Built 1973

  1200 E Peppertree Ln Unit 407, Sarasota, FL 34242

  Last Sold Summary

  • 9% Below List Price
  • $562/SF
  • 179 Days On Market

  • Last Sold Price $820,000
  • Jul 30, 2024

  Last Listing Agent Eliza Miller PEPPERTREE BAY REALTY INC
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  $1,450,000 Pending

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

  5880 Midnight Pass Rd Unit 210, Sarasota, FL 34242

  Under contract-accepting backup offers. 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

  Christa Spalding COLDWELL BANKER REALTY

  5880 Midnight Pass Rd Unit 210, Sarasota, FL 34242
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  $6,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft
  • Condo for Rent

  1255 E Peppertree Dr Unit 101, Sarasota, FL 34242

  This property is a 30 night minimum.This 2 bedroom, 2 bath is located on the first floor in a bay-side mid-rise and is approximately 75 yards from the Bay.The master bedroom has a king bed, a 20 inch TV, a ceiling fan, and access to the extended living lanai. The updated master bathroom has new finishes and a walk-in glass door shower with a removable shower head.The guest bedroom has

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1255 E Peppertree Dr Unit 101, Sarasota, FL 34242
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  $2,600,000 Sold Apr 06, 2026

  5246 Avenida Del Mare, Sarasota, FL 34242

  • 5 Beds
  • 6 Baths
  • 3,206 Sq Ft
  • Built 2015

  Last Sold Summary

  • 16% Below List Price
  • $811/SF
  • 85 Days On Market

  Current Estimated Value $2,942,227

  Last Listing Agent Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  5246 Avenida Del Mare, Sarasota, FL 34242
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  Est $850,227 Not Listed For Sale

  1001 Beach Rd Unit A504, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 1981

  1001 Beach Rd Unit A504, Sarasota, FL 34242

  Last Sold Summary

  • 11% Below List Price
  • $789/SF
  • 0 Days On Market

  • Last Sold Price $950,000
  • Jun 04, 2023

  Last Listing Agent Veronica Murphy KELLER WILLIAMS ON THE WATER S
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  $445,000

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  6157 Midnight Pass Rd Unit E23, Sarasota, FL 34242

  **** BIG PRICE REDUCTION *** MOTIVATED SELLER ****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

  Kathy VanDorne PREFERRED SHORE LLC

  6157 Midnight Pass Rd Unit E23, Sarasota, FL 34242
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  $6,900 Per Month

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

  1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242

  This lovely well-maintained and upgraded condo in a gated community, is located on the ground floor and offers one bedroom plus an additional den furnished as a small guest bedroom. The condo is turnkey furnished including washer /dryer and private garage, an approximate 5-minute walk, via deeded, walking access across the street, to the #1 beach in the U.S.A., Siesta Key! Choose to enjoy two

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242
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  $465,000 Sold Dec 18, 2025

  1125 N Moonmist Ct Unit L5, Sarasota, FL 34242

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft
  • Built 1968

  Last Sold Summary

  • 32% Below List Price
  • $415/SF
  • 321 Days On Market

  Current Estimated Value $483,693

  Last Listing Agent Kari Klein KW COASTAL LIVING III

  1125 N Moonmist Ct Unit L5, Sarasota, FL 34242
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  Est $772,105 Not Listed For Sale

  6300 Midnight Pass Rd Unit 4, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,253 Sq Ft
  • Built 1969

  6300 Midnight Pass Rd Unit 4, Sarasota, FL 34242

  Last Sold Summary

  • 9% Below List Price
  • $678/SF
  • 261 Days On Market

  • Last Sold Price $850,000
  • Apr 30, 2024

  Last Listing Agent Maurice Menager Michael Saunders
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  /15

  $970,000

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft

  1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242

  Experience coastal living and investment potential in this beautifully appointed 3-bedroom, 2-bathroom townhome, ideally located in the highly sought-after Gulf and Bay Club Bayside community on Siesta Key. Just minutes from the world-renowned beaches and Siesta Key Village, this property offers the perfect blend of relaxation and convenience to shopping, dining and entertainment. This turn-key

  Amy Nadell COLDWELL BANKER REALTY

  1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
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  $8,250 Per Month

  • 2 Beds
  • 2 Baths
  • 1,552 Sq Ft
  • House for Rent

  6020 Midnight Pass Rd Unit 52A, Sarasota, FL 34242

  Let’s all go to the beach! Villa 52S at Aloha Kai is a spacious and bright 3-bedroom, 2-bath getaway with plenty of room for everyone to relax and enjoy. The large, open kitchen is perfect for gathering with friends and family to prepare drinks, snacks, or full meals to enjoy in the dining room or on your private rooftop patio. For added convenience, this villa also includes a washer and dryer.

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 52A, Sarasota, FL 34242
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  $1,300,000 Sold Jun 30, 2025

  5402 Shadow Lawn Dr, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,886 Sq Ft
  • Built 1962

  Last Sold Summary

  • 12% Below List Price
  • $689/SF
  • 98 Days On Market

  Current Estimated Value $1,242,022

  Last Listing Agent Jimmy Raybon BERKSHIRE HATHAWAY HOMESERVICE

  5402 Shadow Lawn Dr, Sarasota, FL 34242
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  Est $3,459,739 Not Listed For Sale

  5212 Siesta Cove Dr, Sarasota, FL 34242

  • 5 Beds
  • 6.5 Baths
  • 5,133 Sq Ft
  • Built 1979

  5212 Siesta Cove Dr, Sarasota, FL 34242

  Last Sold Summary

  • 2% Above List Price
  • $662/SF
  • 225 Days On Market

  • Last Sold Price $3,400,000
  • Dec 22, 2023

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY
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  $933,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  5353 Shadow Lawn Dr, Sarasota, FL 34242

  Under contract-accepting backup offers. With NO WATER DAMAGE OR WATER INTRUSION, you can have peace of mind that you are getting a MOVE IN READY piece of tranquility on the beautiful, world renown island of Siesta Key. Being offered Turnkey Finished negotiable, you are ready to move in and get to relaxing on this spacious lot of over a quarter acre of high and dry land. You will find yourself in

  Brittany McCord IRONGATE REALTY INC

  5353 Shadow Lawn Dr, Sarasota, FL 34242
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  $6,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,210 Sq Ft
  • House for Rent

  6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242

  Welcome to your bright and inviting Siesta Key vacation retreat! Enjoy deeded beach access to the stunning Siesta Key Beach, just steps away, where sun and surf await. Relax by Siesta Key’s largest heated pool or unwind in the lush, park-like setting with peaceful bay views. Explore the nearby vibrant Village on Siesta Key, filled with diverse dining, unique shops, and lively events. With

  Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

  6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242
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  $5,250,000 Sold Feb 05, 2026

  216 Tenacity Ln, Sarasota, FL 34242

  • 3 Beds
  • 4 Baths
  • 2,454 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $2,139/SF
  • 2 Days On Market

  Current Estimated Value $5,316,129

  Last Listing Agent Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  216 Tenacity Ln, Sarasota, FL 34242
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  Est $709,673 Not Listed For Sale

  6206 Midnight Pass Rd Unit 203, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • Built 1979

  6206 Midnight Pass Rd Unit 203, Sarasota, FL 34242

  Last Sold Summary

  • 13% Below List Price
  • $621/SF
  • 454 Days On Market

  • Last Sold Price $815,000
  • Jun 19, 2023

  Last Listing Agent Linda Stowe Michael Saunders
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  $599,000

  • 2 Beds
  • 1 Bath
  • 753 Sq Ft

  915 Beach Rd Unit 318, Sarasota, FL 34242

  Experience the ultimate Siesta Key lifestyle in this turnkey furnished, beautifully decorated 2-bedroom, 1-bathroom condo in thehighly sought-after La Siesta Condominiums! Located on the third floor of Building C, this unit boasts stunning views of the community pool and the world-famous Siesta Key Beach—just steps away across the street! With 753 sq. ft. of thoughtfully designed space, this

  Laura Millslagle PREFERRED SHORE LLC

  915 Beach Rd Unit 318, Sarasota, FL 34242
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  $9,900 Per Month

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Condo for Rent

  1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242

  Come and watch the dolphins and manatees on the intercoastal waterway from our lanai! This unit has 2 large bedrooms and 2 full baths. There is a washer and dryer in the unit and a garage to park your car and store all the beach equipment you will need for the beach. It's only a short 10 min. walk down the private deeded beach access to the beautiful white sands of Siesta Key beach. We share

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
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  $690,000 Sold Feb 18, 2026

  1159 Lake House Cir Unit C120, Sarasota, FL 34242

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

  Last Sold Summary

  • $510/SF
  • 248 Days On Market

  Current Estimated Value $685,834

  Last Listing Agent Dan Miller PREFERRED SHORE LLC

  1159 Lake House Cir Unit C120, Sarasota, FL 34242
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  Est $556,496 Not Listed For Sale

  901 Beach Rd Unit 202, Sarasota, FL 34242

  • 2 Beds
  • 1 Bath
  • 753 Sq Ft
  • Built 1972

  901 Beach Rd Unit 202, Sarasota, FL 34242

  Last Sold Summary

  • 3% Below List Price
  • $764/SF
  • 16 Days On Market

  • Last Sold Price $575,000
  • Jul 28, 2023

  Last Listing Agent Solveiga Spalvins LPT REALTY LLC
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  $7,950,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 6,206 Sq Ft

  84 Avenida Veneccia Unit 202 & 203, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Experience luxury living at its finest in this breathtaking one-of-a-kind new construction condominium nestled directly on the pristine shores of world famous Siesta Beach. Spanning over 6200 square feet, this exclusive residence offers unparalleled opulence and panoramic views of the azure waters and fiery sunsets. Elegance meets convenience with a

  Thomas Cail RE/MAX ALLIANCE GROUP

  84 Avenida Veneccia Unit 202 & 203, Sarasota, FL 34242
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  $8,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Condo for Rent

  1055 W Peppertree Dr Unit 606AA, Sarasota, FL 34242

  his condo is in a Gulf-side High-rise on the 6th floor, approximately 75 yards from Crescent Beach.A beautiful remodeled kitchen awaits you with stainless steel appliances, granite counter tops and recessed lighting. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker.The formal dining area has seating for 6 and

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 606AA, Sarasota, FL 34242
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  $815,000 Sold Mar 23, 2026

  6285 Midnight Pass Rd Unit 307, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,461 Sq Ft
  • Built 1981

  Last Sold Summary

  • 8% Below List Price
  • $558/SF
  • 17 Days On Market

  Current Estimated Value $876,256

  Last Listing Agent Trish Wittmus BERKSHIRE HATHAWAY HOMESERVICE

  6285 Midnight Pass Rd Unit 307, Sarasota, FL 34242
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  Est $2,149,886 Not Listed For Sale

  5420 Azure Way, Sarasota, FL 34242

  • 4 Beds
  • 4.5 Baths
  • 4,105 Sq Ft
  • Built 1978

  5420 Azure Way, Sarasota, FL 34242

  Last Sold Summary

  • 2% Above List Price
  • $512/SF
  • 108 Days On Market

  • Last Sold Price $2,100,000
  • Aug 03, 2023

  Last Listing Agent Dan Miller PREFERRED SHORE LLC
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  $3,800,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,200 Sq Ft

  5531 Calle Del Verano, Sarasota, FL 34242

  Pre-Construction. To be built. Brought to you by Noah Thomas Builders in a prime Siesta Key location. This contemporary coastal new construction at 5531 Calle del Verano showcases modern luxury paired with timeless island design—just ONE BLOCK from the powdery quartz sands of Siesta Key Beach, consistently ranked among the best beaches in the world. Thoughtfully engineered and built to FEMA’s

  Holly Wikfors 1ST CLASS REAL ESTATE SUNCOAST

  5531 Calle Del Verano, Sarasota, FL 34242
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  $8,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,346 Sq Ft
  • House for Rent

  431 Island Cir, Sarasota, FL 34242

  This is a short term rental. Listing reflects off season rate. New to the rental market! Whether you’re seeking a relaxing beach escape or an adventure-filled vacation, Island Retreat offers the perfect home base. Its prime location, luxurious amenities, and proximity to both the beach and Siesta Key Village make it an exceptional choice for creating unforgettable memories. Featuring 5

  Beth Dilley ASCENDIA REAL ESTATE

  431 Island Cir, Sarasota, FL 34242
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  $650,000 Sold Jan 16, 2026

  5830 Midnight Pass Rd Unit 89, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 921 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Below List Price
  • $706/SF
  • 117 Days On Market

  Current Estimated Value $633,368

  Last Listing Agent Steve Cavanaugh TIDELINE REAL ESTATE BROKERS

  5830 Midnight Pass Rd Unit 89, Sarasota, FL 34242
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  Est $1,192,703 Not Listed For Sale

  420 Beach Rd Unit 305, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1980

  420 Beach Rd Unit 305, Sarasota, FL 34242

  Last Sold Summary

  • 4% Above List Price
  • $874/SF
  • 393 Days On Market

  • Last Sold Price $1,150,000
  • Aug 01, 2024

  Last Listing Agent Julie Trimpe COMMUNITY REALTY SERVICES
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  $1,995,000

  • 4 Beds
  • 2 Baths
  • 1,996 Sq Ft

  814 Paradise Way, Sarasota, FL 34242

  Exceptional Siesta Key waterfront residence offering a rare opportunity to own a turn-key, move-in-ready 4 bedrooms and 2 bathrooms home in one of the island’s most desirable and tranquil locations. Situated on a quiet cul-de-sac along a grand canal, the property provides privacy, scenic water views, and easy boating access to the Bay with only one higher bridge to navigate. A standout feature is

  Doug Addeo COMMUNITY REALTY ASSOCIATES

  814 Paradise Way, Sarasota, FL 34242
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  $6,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • Condo for Rent

  6052 W Peppertree Way Unit 235B, Sarasota, FL 34242

  This property is a 30 night minimum. 6052 WPW is a Large Garden condo, located approximately 50 yards away from Crescent BeachOpen porch lanai with a 6 person table. Recessed lighting in both bathrooms. Master bathroom has a seat. Recessed lighting in the kitchen. This unit has access to a private garageApprox. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding: Master

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6052 W Peppertree Way Unit 235B, Sarasota, FL 34242
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  $840,000 Sold May 16, 2025

  1273 Dockside Place Unit 116, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,343 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $625/SF
  • 41 Days On Market

  Current Estimated Value $824,430

  Last Listing Agent Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  1273 Dockside Place Unit 116, Sarasota, FL 34242
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  Est $1,716,244 Not Listed For Sale

  5536 Contento Dr, Sarasota, FL 34242

  • 4 Beds
  • 2.5 Baths
  • 2,527 Sq Ft
  • Built 1969

  5536 Contento Dr, Sarasota, FL 34242

  Last Sold Summary

  • 13% Below List Price
  • $778/SF
  • 32 Days On Market

  • Last Sold Price $1,965,000
  • Aug 27, 2024

  Last Listing Agent Mark Coppens EXP REALTY LLC

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