$2,395,000
$295K PRICE DROP
- 3 Beds
- 2 Baths
- 2,341 Sq Ft
4508 Woodside Rd, Sarasota, FL 34242
Derek Edwards KELLER WILLIAMS ON THE WATER S
9,257
Siesta Key, FL Homes
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4508 Woodside Rd, Sarasota, FL 34242
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$12,000
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
- Condo for Rent
19 Whispering Sands Dr Unit 401, Siesta Key, FL 34242
19 Whispering Sands Dr Unit 401, Siesta Key, FL 34242Experience the ultimate Siesta Key lifestyle in this beautifully furnished 2 bedroom, 2 bathroom luxury beachfront condo, perfectly situated in the heart of Siesta Key Village! Wake up just steps away from the gorgeous white sands and crystal clear waters of Siesta Key. Spend your days relaxing on the world-famous beach, enjoying the pool, or taking advantage of the community's resort-style
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$800,000
Sold Apr 21, 20266140 Midnight Pass Rd Unit B6, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
- Built 1967
Last Sold Summary
- 5% Below List Price
- $749/SF
- 38 Days On Market
Current Estimated Value $795,856
Last Listing Agent Kristina Waskom MICHAEL SAUNDERS & COMPANY
6140 Midnight Pass Rd Unit B6, Sarasota, FL 34242 -
Est $471,179
Not Listed For Sale44 Sandy Cove Rd Unit A4, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 561 Sq Ft
- Built 1968
Last Sold Summary
- 3 Days On Market
Last Listing Agent Veronica Murphy KELLER WILLIAMS ON THE WATER S
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$1,499,000
- 3 Beds
- 2 Baths
- 2,114 Sq Ft
670 Venice Ln, Sarasota, FL 34242
670 Venice Ln, Sarasota, FL 34242Oleg Lisitsyn REALTY ONE GROUP MVP
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$12,000
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
- Condo for Rent
19 Whispering Sands Dr Unit 401, Siesta Key, FL 34242
19 Whispering Sands Dr Unit 401, Siesta Key, FL 34242Experience the ultimate Siesta Key lifestyle in this beautifully furnished 2 bedroom, 2 bathroom luxury beachfront condo, perfectly situated in the heart of Siesta Key Village! Wake up just steps away from the gorgeous white sands and crystal clear waters of Siesta Key. Spend your days relaxing on the world-famous beach, enjoying the pool, or taking advantage of the community's resort-style
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$2,650,000
Sold Oct 14, 2025512 Treasure Boat Way, Sarasota, FL 34242
- 4 Beds
- 4.5 Baths
- 5,078 Sq Ft
- Built 1979
Last Sold Summary
- 11% Below List Price
- $522/SF
- 88 Days On Market
Current Estimated Value $2,699,058
Last Listing Agent Derek Edwards KELLER WILLIAMS ON THE WATER S
512 Treasure Boat Way, Sarasota, FL 34242 -
Est $516,849
Not Listed For Sale1257 S Portofino Dr Unit 406, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Built 1968
Last Sold Summary
- 22 Days On Market
Last Listing Agent Curtis Ware KW COASTAL LIVING III
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$5,685,000
$1M PRICE DROP Under Contract- 5 Beds
- 7 Baths
- 6,928 Sq Ft
5132 Jungle Plum Rd, Sarasota, FL 34242
5132 Jungle Plum Rd, Sarasota, FL 34242Joel Schemmel DOUGLAS ELLIMAN
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$4,000 Per Month
- 2 Beds
- 2 Baths
- 991 Sq Ft
- Condo for Rent
1250 N Portofino Dr Unit 301, Sarasota, FL 34242
1250 N Portofino Dr Unit 301, Sarasota, FL 34242Gorgeous updated 2 BR, 2 Bath condo on a Canal Available Now Through December 31st or April 1, 2027 and beyond! Sailboat water, fishing pier, private beach access directly across the street. Beautifully furnished vacation home with water view from main bedroom, Livingroom and lanai. End unit so more light and larger kitchen space. Everything you will need for your beach vacation. Amenities
Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC
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$1,300,000
Sold Jan 30, 20265750 Midnight Pass Rd Unit 508, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,471 Sq Ft
- Built 1984
Last Sold Summary
- 7% Below List Price
- $884/SF
- 107 Days On Market
Current Estimated Value $1,301,441
Last Listing Agent Kathleen Griffin MICHAEL SAUNDERS & COMPANY
5750 Midnight Pass Rd Unit 508, Sarasota, FL 34242 -
Est $570,766
Not Listed For Sale1048 W Peppertree Ln Unit 118B, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 975 Sq Ft
- Built 1974
Last Sold Summary
- 36 Days On Market
Last Listing Agent Marc Rasmussen CORCORAN DWELLINGS REALTY
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$689,000
$10K PRICE DROP- 2 Beds
- 2 Baths
- 1,282 Sq Ft
5600 Beach Way Dr Unit 109, Sarasota, FL 34242
5600 Beach Way Dr Unit 109, Sarasota, FL 34242Lisa Lococo KELLER WILLIAMS ON THE WATER S
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$5,187
Total Monthly Price
- 4 Beds
- 3 Baths
- 2,443 Sq Ft
- Condo for Rent
4879 Commonwealth Dr Unit SI ID1591481P, Siesta Key, FL 34242
4879 Commonwealth Dr Unit SI ID1591481P, Siesta Key, FL 34242The advertised rate of $5,188/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 26, 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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$625,000
Sold Jun 22, 2026145 Avenida Messina Unit 3, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,025 Sq Ft
- Built 1966
Last Sold Summary
- 10% Below List Price
- $610/SF
- 170 Days On Market
Current Estimated Value $615,523
Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP
145 Avenida Messina Unit 3, Sarasota, FL 34242 -
Est $643,450
Not Listed For Sale6145 Midnight Pass Rd Unit F-1, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
- Built 1968
Last Sold Summary
- 20 Days On Market
Last Listing Agent Suki Scollo COLDWELL BANKER REALTY
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$7,675,000
New Construction- 5 Beds
- 7 Baths
- 4,337 Sq Ft
5215 Hidden Harbor Rd, Sarasota, FL 34242
5215 Hidden Harbor Rd, Sarasota, FL 34242Cassandra Miller COASTAL RESERVE
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$9,500 Per Month
- 2 Beds
- 2 Baths
- 1,105 Sq Ft
- Condo for Rent
1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242
1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242Just steps from Crescent Beach, this unit has 2 bedrooms and 2 full bathrooms. Complete with a full kitchen supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and has a Keurig.The formal dining area has seating for 6. This flows into the living area that has comfortable couch seating, a fan, access to the lanai and a 55"
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
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$1,750,000
Sold Jul 28, 2026951 Contento St, Sarasota, FL 34242
- 3 Beds
- 3 Baths
- 2,882 Sq Ft
- Built 1967
Last Sold Summary
- 12% Below List Price
- $607/SF
- 107 Days On Market
Current Estimated Value $1,836,929
Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY
951 Contento St, Sarasota, FL 34242 -
Est $535,522
Not Listed For Sale23 Sandy Cove Rd Unit B1-G, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 561 Sq Ft
- Built 1967
Last Sold Summary
- 24 Days On Market
Last Listing Agent Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC
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$999,000
$73K PRICE DROP- 3 Beds
- 2 Baths
- 2,168 Sq Ft
611 Venice Ln, Sarasota, FL 34242
611 Venice Ln, Sarasota, FL 34242Christine Pope MICHAEL SAUNDERS & COMPANY
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$3,996
Total Monthly Price
- 2 Beds
- 1 Bath
- 1,001 Sq Ft
- Condo for Rent
1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242
1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242The advertised rate of $3,996/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 26, 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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$3,000,000
Sold Oct 15, 2025137 Big Pass Ln, Sarasota, FL 34242
- 5 Beds
- 4.5 Baths
- 4,486 Sq Ft
- Built 2006
Last Sold Summary
- 30% Below List Price
- $669/SF
- 148 Days On Market
Last Listing Agent Dion Souza SARABAY REAL ESTATE INC
137 Big Pass Ln, Sarasota, FL 34242 -
Est $634,704
Not Listed For Sale141 Avenida Messina Unit 3, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,016 Sq Ft
- Built 1966
Last Sold Summary
- 1 Day On Market
Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY
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$549,000
- 1 Bed
- 1 Bath
- 728 Sq Ft
5830 Midnight Pass Rd Unit 51, Sarasota, FL 34242
5830 Midnight Pass Rd Unit 51, Sarasota, FL 34242Steve Cavanaugh TIDELINE REAL ESTATE BROKERS
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$7,400 Per Month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242Indulge in the ultimate coastal lifestyle with this charming 2-bedroom, 2-bathroom first-level condo in the heart of Gulf & Bay Club Bayside on Siesta Key, Florida. As you enter, the coastal vibes welcome you into a thoughtfully designed space adorned with beach-inspired decor and sunlit interiors. Step through the sliding glass doors onto your private screened-in lanai, where the gentle
Andy Moore GULF COAST REALTY & MANAGEMENT
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$1,050,000
Sold May 27, 20261002 Glebe Ln, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 1,808 Sq Ft
- Built 1967
Last Sold Summary
- 9% Below List Price
- $581/SF
- 70 Days On Market
Current Estimated Value $1,077,193
Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY
1002 Glebe Ln, Sarasota, FL 34242 -
Est $927,189
Not Listed For Sale1315 Siesta Bayside Dr Unit B, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,660 Sq Ft
- Built 1988
Last Sold Summary
- 124 Days On Market
Last Listing Agent Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY
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$2,350,000
$50K PRICE DROP- 4 Beds
- 3.5 Baths
- 2,965 Sq Ft
5073 Higel Ave, Sarasota, FL 34242
5073 Higel Ave, Sarasota, FL 34242Abraham Ruth REALTY HUB
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$2,675
Total Monthly Price
- 1 Bed
- 1 Bath
- 333 Sq Ft
- Condo for Rent
60 Avenida Veneccia Unit SI FL2-ID1591445P, Siesta Key, FL 34242
60 Avenida Veneccia Unit SI FL2-ID1591445P, Siesta Key, FL 34242The advertised rate of $2,676/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 11, 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
-
$1,640,000
Sold Mar 24, 20265880 Midnight Pass Rd Unit 710, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 1,713 Sq Ft
- Built 1982
Last Sold Summary
- 3% Below List Price
- $957/SF
- 27 Days On Market
Current Estimated Value $1,616,933
Last Listing Agent Kristina Rain MICHAEL SAUNDERS & COMPANY
5880 Midnight Pass Rd Unit 710, Sarasota, FL 34242 -
Est $2,737,602
Not Listed For Sale1358 Roberts Bay Ln, Siesta Key, FL 34242
- 4 Beds
- 6 Baths
- 5,034 Sq Ft
- Built 1978
Last Sold Summary
- 0 Days On Market
Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY
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$649,000
- 1 Bed
- 1 Bath
- 728 Sq Ft
5830 Midnight Pass Rd Unit 3, Sarasota, FL 34242
5830 Midnight Pass Rd Unit 3, Sarasota, FL 34242Steve Cavanaugh TIDELINE REAL ESTATE BROKERS
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$7,500 Per Month
- 1 Bed
- 1 Bath
- 728 Sq Ft
- Condo for Rent
5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door.Inside, the condo is
Robert Bevington SHOWTIME REALTY
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$452,000
Sold Dec 18, 202573 Avenida Messina Unit 15, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 408 Sq Ft
- Built 1969
Last Sold Summary
- 5% Below List Price
- $1,108/SF
Current Estimated Value $459,708
Last Listing Agent Maxwell Mann MICHAEL SAUNDERS & COMPANY
73 Avenida Messina Unit 15, Sarasota, FL 34242 -
Est $546,496
Not Listed For Sale1600 Cove II Place Unit 421, Sarasota, FL 34242
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
- Built 1979
Last Sold Summary
- 4 Days On Market
Last Listing Agent Brian Livesey WATERSIDE REALTY LLC
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$689,000
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
5600 Beach Way Dr Unit 111, Sarasota, FL 34242
5600 Beach Way Dr Unit 111, Sarasota, FL 34242Lisa Lococo KELLER WILLIAMS ON THE WATER S
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$4,028
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,054 Sq Ft
- Condo for Rent
5855 Midnight Pass Rd Unit SI ID1578366P, Siesta Key, FL 34242
5855 Midnight Pass Rd Unit SI ID1578366P, Siesta Key, FL 34242The advertised rate of $4,028/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 29, 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
-
$1,230,000
Sold Feb 20, 20265354 Calle Florida, Sarasota, FL 34242
- 4 Beds
- 3.5 Baths
- 2,659 Sq Ft
- Built 1954
Last Sold Summary
- 7% Below List Price
- $463/SF
- 96 Days On Market
Current Estimated Value $1,260,271
Last Listing Agent Angelica Ridley KW COASTAL LIVING III
5354 Calle Florida, Sarasota, FL 34242 -
Est $790,416
Not Listed For Sale5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 816 Sq Ft
- Built 1970
Last Sold Summary
Last Listing Agent Charles Totonis PREMIER SOTHEBY'S INTERNATIONAL REALTY
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