Siesta Key, FL Homes

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  /39

  $1,750,000

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  5966 Midnight Pass Rd Unit G113, Sarasota, FL 34242

  Discover the rare opportunity to own a penthouse-level residence in the iconic Tower at the Palm Bay Club on Siesta Key—where panoramic Gulf views and effortless island living come together in one exceptional offering. This spacious 2-bedroom, 2-bath condominium sits high above the shoreline, capturing sweeping vistas of the turquoise waters and legendary Siesta Key sunsets from its exclusive

  Rudy Dudon MICHAEL SAUNDERS & COMPANY

  5966 Midnight Pass Rd Unit G113, Sarasota, FL 34242
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  /22

  $9,000 per month

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

  1055 W Peppertree Dr Unit 106AA, Sarasota, FL 34242

  Indulge in coastal luxury with this beautifully decorated Gulfside unit nestled on the 1st floor of a stunning high-rise. With hardwood floors throughout and thoughtfully curated decor, this retreat offers the perfect blend of elegance and comfort. Step into the spacious living area, where natural light floods through large windows, illuminating the stylish furnishings and inviting ambiance. The

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 106AA, Sarasota, FL 34242
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  $3,990,000 Sold Aug 12, 2025

  4815 Featherbed Ln, Sarasota, FL 34242

  • 5 Beds
  • 4 Baths
  • 3,329 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $1,199/SF
  • 178 Days On Market

  Current Estimated Value $3,762,573

  Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

  4815 Featherbed Ln, Sarasota, FL 34242
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  /57

  Est $727,257 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,101 Sq Ft

  6150 Midnight Pass Rd Unit 7, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 7, Sarasota, FL 34242
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  /21

  $4,850,000

  • Land
  • 2 Acres
  • $2,425,000 per Acre

  7707 Midnight Pass Rd, Sarasota, FL 34242

  Two-acre+/- lot on Little Sarasota Bay with exceptional privacy, views, boating access and development potential. This listing includes twocontiguous buildable parcels (ID#s 0127030017 & 0127030018) which are only offered together. This unique lot with mature trees and lushlandscaping includes a secluded bay offering protection of your lot and future dock from the elements as well as

  Lisa Maria 1ST VISION REALTY OF FLORIDA I

  7707 Midnight Pass Rd, Sarasota, FL 34242
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  /31

  $8,500 per month

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

  1055 W Peppertree Dr Unit 206AA, Sarasota, FL 34242

  2 BR - 2 BA - 6 person Max - Highrise - Pond View - Approx. 75 yards from beach This property is a 30 night minimum. Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 full bathroom unit has it all. The unit is in a gulf side high rise building on the 2nd floor. Assigned covered parking located in the parking garage under the building. A luxurious dining area greets you

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 206AA, Sarasota, FL 34242
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  /2

  $357,000 Sold Sep 19, 2025

  1300 N Portofino Dr Unit 208, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 991 Sq Ft
  • Built 1969

  Last Sold Summary

  • 29% Below List Price
  • $360/SF
  • 403 Days On Market

  Current Estimated Value $378,741

  Last Listing Agent Jill Thomas BERKSHIRE HATHAWAY HOMESERVICE

  1300 N Portofino Dr Unit 208, Sarasota, FL 34242
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  /61

  Est $716,714 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,101 Sq Ft

  6150 Midnight Pass Rd Unit 5, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 5, Sarasota, FL 34242
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  /44

  $474,000

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  6157 Midnight Pass Rd Unit E24, Sarasota, FL 34242

  Elevated Living on the 4th Floor! Discover this well appointed 1-bedroom, 1-bath condo just minutes from the world-renowned Siesta Key Beach. This TURN KEY residence offers the ideal blend of relaxed Florida living and exceptional value. Step into a bright and airy space where natural light pours into the east-facing screened balcony, overlooking lush tropical landscaping. The interior features

  Ingrid Caruso COLDWELL BANKER REALTY

  6157 Midnight Pass Rd Unit E24, Sarasota, FL 34242
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  /27

  $5,700 per month

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

  1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242

  Steps from beautiful Crescent Beach, this fully renovated 2 bedroom 2 full bathroom unit is located in Gulf-side High-rise on the 8th floor. Step into the extended living lanai area to experience wrap around views of the gulf. Enjoy a window bench, choice of comfy loveseats, or dine with a view of the blue waters and white sand.An updated kitchen with stainless steel appliances peeks through

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242
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  /2

  $840,000 Sold Feb 25, 2025

  5420 Cape Leyte Dr, Sarasota, FL 34242

  • Land
  • 0.35 Acre
  • $2,400,000 per Acre

  Last Sold Summary

  • 1% Above List Price
  • 2 Days On Market

  Current Estimated Value $805,566

  Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

  5420 Cape Leyte Dr, Sarasota, FL 34242
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  /57

  Est $775,878 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,212 Sq Ft

  6140 Midnight Pass Rd Unit B1, Sarasota, FL 34242

  6140 Midnight Pass Rd Unit B1, Sarasota, FL 34242
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  /58

  $1,750,000

  • 3 Beds
  • 3 Baths
  • 2,724 Sq Ft

  1260 Dolphin Bay Way Unit 401, Sarasota, FL 34242

  Stunning 3-bedroom, 3-bath residence on the 4th floor of Dolphin Bay, offering spectacular wide-water views of the Intracoastal. This end-unit condo lives like a single-family home with its open, spacious layout, light and bright floor plan, and beautifully curated coastal design—a true retreat that blends comfort, style, and everyday livability. The heart of the home is the impressive gourmet

  Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  1260 Dolphin Bay Way Unit 401, Sarasota, FL 34242
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  /32

  $11,100 per month

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

  1055 W Peppertree Dr Unit 805AA, Sarasota, FL 34242

  2 BR - 2 BA - 4 Person Max - High-rise - Pond View - Approximately 75 yards away from Crescent BeachThis property is a 30 night minimum.This luxurious 2 bedroom, 2 full bathroom unit is only steps from Crescent Beach. Located on the 8th floor in a Gulf-side High-rise, you will experience the many beautiful views of Siesta Key.The kitchen has stainless steel appliances, updated floors,

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 805AA, Sarasota, FL 34242
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  /2

  $700,000 Sold Aug 27, 2025

  1228 Siesta Bayside Dr Unit 1228C, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1988

  Last Sold Summary

  • 18% Below List Price
  • $547/SF
  • 155 Days On Market

  Current Estimated Value $684,263

  Last Listing Agent Fred Sieger Jr COMPASS FLORIDA LLC

  1228 Siesta Bayside Dr Unit 1228C, Sarasota, FL 34242
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  /21

  Est $538,455 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 766 Sq Ft

  5128 Calle Minorga Unit 5128, Sarasota, FL 34242

  5128 Calle Minorga Unit 5128, Sarasota, FL 34242
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  /63

  $445,000 Open Sat 12PM - 2PM

  • 1 Bed
  • 1 Bath
  • 656 Sq Ft

  117 Pass Key Rd Unit 117, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Enjoy the best of Siesta Key living in beautiful Sandy Cove 3, an intimate and highly desirable community of just 16 units with a heated pool and exceptional Gulf-side amenities. This fully renovated 1-bedroom, 1-bath residence features all-new stainless-steel appliances, wood cabinetry, quartz countertops, a new bathroom vanity, an updated shower,

  Tim Yocum, Sr COLDWELL BANKER REALTY

  117 Pass Key Rd Unit 117, Sarasota, FL 34242
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  /22

  $9,550 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 407, Sarasota, FL 34242

  Discover modern comfort in this stylishly updated 2BR/2BA vacation rental condo. Perfect for relaxation and rejuvenation, this well-appointed space offers everything you need for a memorable getaway. Enjoy garden views from the lanai. Modern amenities include new coastal-inspired furniture and stainless steel appliances. Enjoy community pool access for refreshing dips after beach days. Bask in

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 407, Sarasota, FL 34242
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  $1,350,000 Sold Dec 08, 2025

  5880 Midnight Pass Rd Unit 403, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $901/SF
  • 38 Days On Market

  Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

  5880 Midnight Pass Rd Unit 403, Sarasota, FL 34242
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  /64

  Est $607,595 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft

  225 Hourglass Way Unit 307, Sarasota, FL 34242

  225 Hourglass Way Unit 307, Sarasota, FL 34242
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  /43

  $899,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 1,967 Sq Ft

  795 Plymouth St, Sarasota, FL 34242

  Welcome to your slice of paradise on Siesta Key. This beautifully updated 4-bedroom home offers the perfect blend of coastal charm and modern comfort, nestled on a peaceful, tree-lined street in one of the island’s most sought-after neighborhoods. Step inside to discover a bright, airy interior filled with natural light, where spacious living areas flow effortlessly into a large open-air pool,

  Courtney Church COLDWELL BANKER REALTY

  795 Plymouth St, Sarasota, FL 34242
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  /24

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 501, Sarasota, FL 34242

  2 BR -- 2 BA -- 4 Person Max -- High Rise -- Beach and Pond View1125-501 is a high-rise unit, located on the Gulf-side of Midnight Pass, approx. 175 yards away from Crescent beach.Open kitchen floor plan with recessed lighting. Granite counters, Stainless steel fridge. Assigned covered parking located in parking garage.Approx. 1200 Sq. Ft. (1480 including the lanai).Condo

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 501, Sarasota, FL 34242
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  $780,000 Sold Mar 11, 2025

  5133 Sandy Beach Ave, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft
  • Built 1969

  Last Sold Summary

  • 8% Below List Price
  • $523/SF
  • 99 Days On Market

  Current Estimated Value $726,051

  Last Listing Agent Joanna Benante MICHAEL SAUNDERS & COMPANY

  5133 Sandy Beach Ave, Sarasota, FL 34242
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  /34

  Est $619,501 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  4660 Ocean Blvd Unit F1, Sarasota, FL 34242

  4660 Ocean Blvd Unit F1, Sarasota, FL 34242
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  /54

  $2,000,000

  • 4 Beds
  • 3 Baths
  • 2,838 Sq Ft

  5334 Calle Florida, Sarasota, FL 34242

  Fantastic opportunity to own a unique home on Palm Island, in this exceptional Siesta Key residence, ideally located at 5334 Calle Florida. Situated on a large lot and elevated approximately 10 feet above sea level, the main home has never flooded during any storms, offering peace of mind along with island luxury. This 4-bedroom, 3-bathroom home features 2,838 square feet of thoughtfully designed

  Niall Phelan LPT REALTY, LLC

  5334 Calle Florida, Sarasota, FL 34242
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  /31

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 605, Sarasota, FL 34242

  2 BR - 2 BA - 6 Person Max - Pond View - Gulf-side High-rise - Approx. 150 yards from beachThis property is a 30 night minimum.Unit 1125-605 offers assigned covered parking under the building.The master bedroom offers a King bed and a walk-in glass door shower with 2 vanities.The guest bedroom offers 2 twin beds and a walk-in glass door shower with one vanity.Enjoy the futon

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 605, Sarasota, FL 34242
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  $420,000 Sold Jan 05, 2026

  6350 Midnight Cove Rd Unit 710, Sarasota, FL 34242

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft
  • Built 1979

  Last Sold Summary

  • 14% Below List Price
  • $488/SF
  • 30 Days On Market

  Last Listing Agent Nancie Kalin MICHAEL SAUNDERS & COMPANY

  6350 Midnight Cove Rd Unit 710, Sarasota, FL 34242
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  /55

  Est $1,109,868 Not Listed For Sale

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

  6342 Midnight Pass Rd Unit 425, Sarasota, FL 34242

  6342 Midnight Pass Rd Unit 425, Sarasota, FL 34242
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  /28

  $480,000

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

  Unlisted Address

  Welcome to the World-famous Siesta Key Beach. Come check out This well maintained 2-bedroom 2 bath move in ready condo at Whitesands Village across the street from the public beach! Looking to enjoy living the beach lifestyle in Paradise at a great price. This property offers a heated swimming pool, sauna, nice club house, grills. Pet friendly! Siesta Key offers volleyball, pickle ball, yoga on

  Terry Millett GULF SHORES REALTY & RENTALS

  Unlisted Address
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  /37

  $10,000 per month

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

  1125 W Peppertree Dr Unit 102, Sarasota, FL 34242

  A 3 month stay is preferred but will accept a 2 month stay, possible 1 month. Call the office for details.Luxuriously remodeled 2 bedroom 2 full bath unit on the first floor in a gulf side high-rise building.The unit has updated wood tiles throughout, ceiling fans in each room, recessed and updated lighting.The kitchen is fully updated with stainless steel appliances, gorgeous counter

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 102, Sarasota, FL 34242
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  /2

  $852,500 Sold Jan 07, 2026

  5780 Midnight Pass Rd Unit 303, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $626/SF
  • 20 Days On Market

  Last Listing Agent Curtis Ware KW COASTAL LIVING III

  5780 Midnight Pass Rd Unit 303, Sarasota, FL 34242
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  /86

  Est $657,703 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  6415 Midnight Pass Rd Unit 506, Sarasota, FL 34242

  6415 Midnight Pass Rd Unit 506, Sarasota, FL 34242
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  /66

  $669,000

  • 2 Beds
  • 1.5 Baths
  • 959 Sq Ft

  1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242

  Welcome to 1313 Siesta Bayside Drive in Gulf & Bay Club Bayside, a beautifully updated 2-bedroom, 1.5-bath condo offered turnkey furnished and ideally suited as a personal beach retreat or high-performing investment property with weekly rental flexibility and consistent future bookings already in place. This light-filled residence features tasteful coastal updates and a serene pond waterview,

  Shane Lewis MICHAEL SAUNDERS & COMPANY

  1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242
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  /26

  $9,225 per month

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

  1125 W Peppertree Dr Unit 402, Sarasota, FL 34242

  Stylish 2-Bedroom, 2-Bathroom Condo in Peppertree Bay - Siesta Key, FLLooking for the perfect vacation getaway? This stunning 2-bedroom, 2-bathroom condo in the desirable Peppertree Bay community is just what you need! Nestled on the fourth floor, this high-rise retreat offers tranquil pond views and a serene atmosphere.The unit features assigned covered parking under the building for

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 402, Sarasota, FL 34242
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  /2

  $650,000 Sold Nov 25, 2025

  5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1974

  Last Sold Summary

  • 21% Below List Price
  • $650/SF
  • 199 Days On Market

  Last Listing Agent Mary Beth Hudson COLDWELL BANKER REALTY

  5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242
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  /40

  Est $486,708 Not Listed For Sale

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

  5681 Midnight Pass Rd Unit 103, Sarasota, FL 34242

  5681 Midnight Pass Rd Unit 103, Sarasota, FL 34242
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  /67

  $4,990,000 New Construction

  • 8 Beds
  • 8.5 Baths
  • 4,380 Sq Ft

  135 Avenida Veneccia, Sarasota, FL 34242

  Experience elevated coastal living just moments from the powdery sands of Siesta Key Beach and the heart of Siesta Village. This newly built island escape offers eight bedrooms and eight and a half baths, thoughtfully designed for style, comfort, and effortless group living.Step into your own resort-inspired backyard with a shimmering pool, relaxing spa, and a waterslide wrapped in tropical

  Curtis Ware KW COASTAL LIVING III

  135 Avenida Veneccia, Sarasota, FL 34242
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  /25

  $8,500 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 707, Sarasota, FL 34242

  2 BR - 2 BA - 4 Person Max - Gulf side - Mid-Rise - Approx.150 yards from beach This property is a 30 night minimum.This 2-bedroom, 2 bath located on the gulf side is approx. 150 yards from the beach. This unit is on the 7th floor, accessible via elevator or stairs. Plenty of room for dining at the 6-service dining table. Couches, a ceiling fan, and TV in the living room for

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 707, Sarasota, FL 34242
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  /2

  $1,266,700 Sold Dec 19, 2025

  307 Avenida de Paradisio, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,511 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $838/SF
  • 28 Days On Market

  Last Listing Agent Jason Skowronski COMPASS FLORIDA LLC

  307 Avenida de Paradisio, Sarasota, FL 34242
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  /54

  Est $982,030 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft

  4660 Ocean Blvd Unit K1, Sarasota, FL 34242

  4660 Ocean Blvd Unit K1, Sarasota, FL 34242

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