$1,999,999
$249K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,774 Sq Ft
5361 Siesta Ct, Sarasota, FL 34242
David James CHARLES RUTENBERG REALTY INC
9,257
Siesta Key, FL Homes
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5361 Siesta Ct, Sarasota, FL 34242
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$5,970 Per Month
- 1 Bed
- 1 Bath
- 696 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242
6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242This beautifully updated Villa 12 at Aloha Kai is ready to give the perfect beach getaway. Just steps from the villa, you can stroll along the beach with your morning coffee and return in time for a breathtaking sunset. The screened porch provides a lovely spot to enjoy the balmy afternoon breezes in comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
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$7,200,000
Sold Jul 21, 202670 Avenida Veneccia Unit 203, Sarasota, FL 34242
- 3 Beds
- 3.5 Baths
- 3,627 Sq Ft
- Built 2025
Last Sold Summary
- $1,985/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE
70 Avenida Veneccia Unit 203, Sarasota, FL 34242 -
Est $688,475
Not Listed For Sale5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,270 Sq Ft
- Built 1974
Last Sold Summary
- 29 Days On Market
Last Listing Agent Mary Beth Hudson COLDWELL BANKER REALTY
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$3,397,500
New Construction Open House 9/05 $260K PRICE DROP- 3 Beds
- 4.5 Baths
- 3,034 Sq Ft
5103 Windward Ave, Sarasota, FL 34242
5103 Windward Ave, Sarasota, FL 34242Karen Greco GRECO REAL ESTATE
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$7,679
Total Monthly Price
- 4 Beds
- 2 Baths
- 2,055 Sq Ft
- Condo for Rent
349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242
349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242The advertised rate of $7,680/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 27, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
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$575,000
Sold Apr 27, 20265830 Midnight Pass Rd Unit 94, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 921 Sq Ft
- Built 1970
Last Sold Summary
- 4% Below List Price
- $624/SF
- 56 Days On Market
Current Estimated Value $582,738
Last Listing Agent Kaitlin Kuhn MICHAEL SAUNDERS & COMPANY
5830 Midnight Pass Rd Unit 94, Sarasota, FL 34242 -
Est $630,966
Not Listed For Sale5600 Beach Way Dr Unit 215, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,259 Sq Ft
- Built 1970
Last Sold Summary
- 142 Days On Market
Last Listing Agent Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.
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$6,750,000
New Construction Under Contract- 4 Beds
- 4 Baths
- 3,348 Sq Ft
70 Avenida Veneccia Unit 201, Sarasota, FL 34242
70 Avenida Veneccia Unit 201, Sarasota, FL 34242David Lehrman THE SARASOTA REAL ESTATE COMP.
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$8,500 Per Month
- 3 Beds
- 2 Baths
- 1,290 Sq Ft
- House for Rent
5216 Calle de Costa Rica, Sarasota, FL 34242
5216 Calle de Costa Rica, Sarasota, FL 34242Listing reflects peak season rate. Available months: July 2026, August 2026, October 2026, November 2026 December 2026, January 2027, March 2027 and April 2027. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key
Beth Dilley ASCENDIA REAL ESTATE
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$729,000
Sold Oct 17, 20251240 Siesta Bayside Dr Unit 1240C, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Built 1988
Last Sold Summary
- 6% Below List Price
- $570/SF
- 96 Days On Market
Current Estimated Value $733,314
Last Listing Agent Gina LaRouche COLDWELL BANKER REALTY
1240 Siesta Bayside Dr Unit 1240C, Sarasota, FL 34242 -
Est $611,825
Not Listed For Sale5963 Midnight Pass Rd Unit 359, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
- Built 1974
Last Sold Summary
- 172 Days On Market
Last Listing Agent Kara Wootson WAGNER REALTY
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$669,000
- 2 Beds
- 2 Baths
- 1,083 Sq Ft
1141 W Peppertree Dr Unit 118B, Sarasota, FL 34242
1141 W Peppertree Dr Unit 118B, Sarasota, FL 34242Eliza Miller PEPPERTREE BAY REALTY INC
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$9,240
Total Monthly Price
- 3 Beds
- 3 Baths
- 1,732 Sq Ft
- Condo for Rent
338 Avenida de Paradisio Unit SI FL1-ID1590869P, Siesta Key, FL 34242
338 Avenida de Paradisio Unit SI FL1-ID1590869P, Siesta Key, FL 34242The advertised rate of $9,240/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
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$460,000
Sold Dec 04, 20255649 Midnight Pass Rd Unit 804, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,012 Sq Ft
- Built 1975
Last Sold Summary
- 4% Below List Price
- $455/SF
- 92 Days On Market
Current Estimated Value $476,851
Last Listing Agent Janet Trefry RE/MAX ALLIANCE GROUP
5649 Midnight Pass Rd Unit 804, Sarasota, FL 34242 -
Est $644,765
Not Listed For Sale5963 Midnight Pass Rd Unit 328, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
- Built 1974
Last Sold Summary
- 18 Days On Market
Last Listing Agent Mary Beth Hudson COLDWELL BANKER REALTY
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$1,600,000
- 3 Beds
- 2.5 Baths
- 2,557 Sq Ft
5231 Siesta Cove Dr, Sarasota, FL 34242
5231 Siesta Cove Dr, Sarasota, FL 34242Natalie Gutwein MICHAEL SAUNDERS & COMPANY
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$4,500 Per Month
- 3 Beds
- 2 Baths
- 1,438 Sq Ft
- House for Rent
5253 Avenida Del Mare, Sarasota, FL 34242
5253 Avenida Del Mare, Sarasota, FL 34242Listing price reflects off season rate, in season rates will be higher. Escape to paradise at this beautiful vacation retreat located on the coveted north end of Siesta Key. Nestled in a quiet residential neighborhood, this spacious and elegantly appointed home offers the perfect blend of privacy, comfort, and convenience—just minutes from world-famous Siesta Key Beach and Siesta Key Village.
Beth Dilley ASCENDIA REAL ESTATE
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$865,000
Sold Mar 05, 2026315 Avenida de Paradisio, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 1,464 Sq Ft
- Built 1971
Last Sold Summary
- 9% Below List Price
- $591/SF
- 105 Days On Market
Current Estimated Value $901,164
Last Listing Agent Jason Skowronski COMPASS FLORIDA LLC
315 Avenida de Paradisio, Sarasota, FL 34242 -
Est $638,190
Not Listed For Sale6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
- Built 1967
Last Sold Summary
- 0 Days On Market
Last Listing Agent Barrett Webber BEACHY PROPERTIES
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$2,240,000
$352K PRICE INCREASE- 3 Beds
- 2.5 Baths
- 1,670 Sq Ft
462 Island Cir, Sarasota, FL 34242
462 Island Cir, Sarasota, FL 34242Dan Miller PREFERRED SHORE LLC
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$11,685
Total Monthly Price
- 2 Beds
- 2 Baths
- 796 Sq Ft
- Condo for Rent
1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242
1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242The advertised rate of $11,685/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
-
$800,000
Sold Dec 19, 20256300 Midnight Pass Rd Unit 2, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,296 Sq Ft
- Built 1969
Last Sold Summary
- 6% Below List Price
- $617/SF
- 127 Days On Market
Current Estimated Value $795,743
Last Listing Agent Mike Warm PREMIER SOTHEBY'S INTERNATIONAL REALTY
6300 Midnight Pass Rd Unit 2, Sarasota, FL 34242 -
Est $563,179
Not Listed For Sale1500 Cove II Place Unit 532, Sarasota, FL 34242
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
- Built 1979
Last Sold Summary
- 41 Days On Market
Last Listing Agent Jason Wood CORCORAN DWELLINGS REALTY
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$1,300,000
$100K PRICE DROP- 2 Beds
- 2 Baths
- 1,498 Sq Ft
5880 Midnight Pass Rd Unit 804, Sarasota, FL 34242
5880 Midnight Pass Rd Unit 804, Sarasota, FL 34242Maurice Menager MICHAEL SAUNDERS & COMPANY
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$9,500 Per Month
- 3 Beds
- 2 Baths
- 1,835 Sq Ft
- Condo for Rent
1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and
Andy Moore GULF COAST REALTY & MANAGEMENT
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$2,500,000
Sold Apr 15, 20265770 Midnight Pass Rd Unit 608, Sarasota, FL 34242
- 3 Beds
- 2.5 Baths
- 2,085 Sq Ft
- Built 1980
Last Sold Summary
- $1,199/SF
- 3 Days On Market
Current Estimated Value $2,387,290
Last Listing Agent Sylvia Wilk PREFERRED SHORE LLC
5770 Midnight Pass Rd Unit 608, Sarasota, FL 34242 -
Est $674,529
Not Listed For Sale1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,139 Sq Ft
- Built 1975
Last Sold Summary
- 48 Days On Market
Last Listing Agent Ian McPherson COLDWELL BANKER REALTY
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$679,000
$20K PRICE DROP- 2 Beds
- 2 Baths
- 1,271 Sq Ft
101 Whispering Sands Dr Unit 105, Sarasota, FL 34242
101 Whispering Sands Dr Unit 105, Sarasota, FL 34242Michael A Martino KELLER WILLIAMS ON THE WATER S
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$1,938
Total Monthly Price
- 2 Beds
- 1 Bath
- 1,108 Sq Ft
- Condo for Rent
6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242
6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242The advertised rate of $1,939/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 27, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
-
$1,500,000
Sold Dec 01, 20251038 Contento St, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 2,217 Sq Ft
- Built 1972
Last Sold Summary
- 13% Below List Price
- $677/SF
- 169 Days On Market
Current Estimated Value $1,540,051
Last Listing Agent Sara Leicht SARASELLSSARASOTA.COM
1038 Contento St, Sarasota, FL 34242 -
Est $981,929
Not Listed For Sale1319 Dockside Place Unit 221, Sarasota, FL 34242
- 3 Beds
- 3 Baths
- 1,827 Sq Ft
- Built 1982
Last Sold Summary
- 141 Days On Market
Last Listing Agent Robert Ruiz WILLIAM RAVEIS - FLORIDA LLC
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$349,000
- 1 Bed
- 1 Bath
- 797 Sq Ft
5683 Midnight Pass Rd Unit 105, Sarasota, FL 34242
5683 Midnight Pass Rd Unit 105, Sarasota, FL 34242Brian Wood COMPASS FLORIDA LLC
-
$7,050 Per Month
- 2 Beds
- 2 Baths
- 1,105 Sq Ft
- Condo for Rent
1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242This luxurious condo is in a Gulf-side High-rise and is located on the 7th floor. This condo has 2 bedrooms and 2 full bathrooms.A fully equipped kitchen awaits you with cabinet lighting, a ceiling fan and a breakfast bar for 3. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and a Keurig.The formal dining room
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
-
$1,954,700
Sold May 28, 20265024 Commonwealth Dr, Sarasota, FL 34242
- 3 Beds
- 3.5 Baths
- 2,468 Sq Ft
- Built 2003
Last Sold Summary
- 30% Below List Price
- $792/SF
- 320 Days On Market
Current Estimated Value $1,980,169
Last Listing Agent Gabi Charity CHARITY & WEISS INTERNATIONAL LLC
5024 Commonwealth Dr, Sarasota, FL 34242 -
Est $1,936,024
Not Listed For Sale5966 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
- 7 Days On Market
Last Listing Agent Carolyn Donnelly COLDWELL BANKER REALTY
-
$5,690,000
New Construction- 5 Beds
- 5 Baths
- 4,195 Sq Ft
539 Avenida Del Norte, Sarasota, FL 34242
539 Avenida Del Norte, Sarasota, FL 34242Andrew Azzarello PREFERRED SHORE LLC
-
$9,240
Total Monthly Price
- 3 Beds
- 3 Baths
- 1,732 Sq Ft
- Condo for Rent
338 Avenida de Paradisio Unit SI FL1-ID1590869P, Siesta Key, FL 34242
338 Avenida de Paradisio Unit SI FL1-ID1590869P, Siesta Key, FL 34242The advertised rate of $9,240/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
-
$1,250,000
Sold Apr 30, 20265770 Midnight Pass Rd Unit 404, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,337 Sq Ft
- Built 1980
Last Sold Summary
- 7% Below List Price
- $935/SF
- 37 Days On Market
Current Estimated Value $1,236,640
Last Listing Agent Tina Johns COLDWELL BANKER REALTY
5770 Midnight Pass Rd Unit 404, Sarasota, FL 34242 -
Est $572,212
Not Listed For Sale5855 Midnight Pass Rd Unit 127, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
- Built 1976
Last Sold Summary
- 368 Days On Market
Last Listing Agent Ethel Lovelace MICHAEL SAUNDERS & COMPANY
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