9,260

Siesta Key, FL Homes

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  • /90

    $4,500,000

    $500K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,750 Sq Ft

    534 Beach Rd Unit 4, Sarasota, FL 34242

    Repriced to the market - reduced $500,000! An exquisite Gulf-front penthouse - a private third floor residence with a loft and private rooftop deck overlooking Siesta Key’s pristine sands. Immerse yourself in the ultimate coastal luxury lifestyle with this spectacular Gulf-front penthouse, in an exclusive 3-residence boutique building, where each home occupies its private floor. Just near the

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    534 Beach Rd Unit 4, Sarasota, FL 34242
  • /11

    $7,470 Per Month

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

    6154 Midnight Pass Rd Unit B03, Sarasota, FL 34242

    Casa Blanca Beach Resort includes Gulf-front Apartments and Private Villas. Each villa and apartment are individually owned. The minimum stay is 5 or 7 nights, depending on the owner. Every Unit at Casa Blanca is individually decorated and fully furnished including all cookware and linens including beach towels. They have individually controlled AC/Heating and color cable TVs, WIFI, telephones

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit B03, Sarasota, FL 34242
  • /2

    $825,000

    Sold Sep 12, 2025

    514 Ralph St, Sarasota, FL 34242

    • 4 Beds
    • 3 Baths
    • 1,934 Sq Ft
    • Built 1957

    Last Sold Summary

    • 30% Below List Price
    • $427/SF
    • 169 Days On Market

    Current Estimated Value $889,549

    Last Listing Agent Tim Yocum, Sr COLDWELL BANKER REALTY

    514 Ralph St, Sarasota, FL 34242
    • /2

      Est $1,138,291

      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

      • 393 Days On Market

      Last Listing Agent Julie Trimpe COMMUNITY REALTY SERVICES

  • /34

    $995,000

    $80K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft

    6308 Midnight Pass Rd Unit 6, Sarasota, FL 34242

    Coastal Luxury Villa with Thai-Inspired Elegance Now Offered at $995,000 Experience the best of Siesta Key living in this beautifully renovated two-bedroom, two-bath villa located in the highly sought-after, gated beachfront community of Crescent Arms. Now priced at $995,000, this is a compelling opportunity recently adjusted from $1,075,000 to reflect today’s market and create immediate value.

    Derek Edwards KELLER WILLIAMS ON THE WATER S

    6308 Midnight Pass Rd Unit 6, Sarasota, FL 34242
  • /84

    $9,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft
    • House for Rent

    327 Avenida Milano, Sarasota, FL 34242

    Welcome to this amazing Siesta Key vacation home! This beautiful 3 bed/2 bath canal-front beach home is ideally located just a short stroll to Siesta Key Village, with its array of shops, dining options, and entertainment. Situated on a quiet residential street. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with modern finishes. The beautifully

    Chrissie Cummings JENNETTE PROPERTIES INC

    327 Avenida Milano, Sarasota, FL 34242
  • /2

    $1,100,000

    Sold Mar 20, 2026

    6342 Midnight Pass Rd Unit 310, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 852 Sq Ft
    • Built 1977

    Last Sold Summary

    • 6% Below List Price
    • $1,291/SF
    • 0 Days On Market

    Current Estimated Value $1,097,349

    Last Listing Agent Brian Livesey WATERSIDE REALTY LLC

    6342 Midnight Pass Rd Unit 310, Sarasota, FL 34242
    • /2

      Est $694,784

      Not Listed For Sale

      1155 Lake House Cir Unit C119, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,352 Sq Ft
      • Built 1981
      1155 Lake House Cir Unit C119, Sarasota, FL 34242

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Jennifer Putnam COLDWELL BANKER SARASOTA CENT.

  • /33

    $630,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,401 Sq Ft

    6287 Midnight Pass Rd Unit 201, Sarasota, FL 34242

    Under contract-accepting backup offers. Beautiful Excelsior Beach to Bay - absolutely gorgeous condo complex and beautifully refreshed and remodeled unit. This condo lives large - plenty of room to relax and not feel cramped on a rainy day! Jumbo sized Master bedroom with private, totally remodeled and updated bath and ample sized walk in closet. Second bedroom holds two queen sized beds for

    Kimberlie MacDonald COLDWELL BANKER REALTY

    6287 Midnight Pass Rd Unit 201, Sarasota, FL 34242
  • /27

    $12,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,495 Sq Ft
    • Condo for Rent

    1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242

    Enjoy your vacation on Siesta Key in this spacious three bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private beach access to Siesta Key’s world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key.**Taxes and fees not included.

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
  • /2

    $720,000

    Sold Feb 05, 2026

    312 Avenida Leona, Siesta Key, FL 34242

    • 4 Beds
    • 3.5 Baths
    • 1,824 Sq Ft
    • Built 2026

    Last Sold Summary

    • 58% Below List Price
    • $395/SF
    • 161 Days On Market

    Current Estimated Value $935,000

    Last Listing Agent Ron Pepka KW SUNCOAST

    312 Avenida Leona, Siesta Key, FL 34242
    • /2

      Est $1,784,233

      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

      • 32 Days On Market

      Last Listing Agent Mark Coppens EXP REALTY LLC

  • /46

    $1,199,000

    $176K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 2,200 Sq Ft

    1240 Dolphin Bay Way Unit 401, Sarasota, FL 34242

    Under contract-accepting backup offers. Huge Price Reduction!!! Fourth-floor end unit offering breathtaking views of the intracoastal waterway, featuring three spacious bedrooms and three full ensuite baths. Newly installed luxury vinyl plank flooring graces the entire unit. The expansive glassed lanai boasts recently replaced sliding doors, complete with accordion shutters on the inner doors and

    Ethel Lovelace MICHAEL SAUNDERS & COMPANY

    1240 Dolphin Bay Way Unit 401, Sarasota, FL 34242
  • /98

    $18,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • House for Rent

    345 Avenida Leona, Sarasota, FL 34242

    Listing reflects peak season rate. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a bright, coastal-styled haven designed for relaxation and comfort. The spacious primary

    Beth Dilley ASCENDIA REAL ESTATE

    345 Avenida Leona, Sarasota, FL 34242
  • /2

    $1,100,000

    Sold Jul 06, 2026

    5400 Ocean Blvd Unit 6-4, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,187 Sq Ft
    • Built 1970

    Last Sold Summary

    • 24% Below List Price
    • $927/SF
    • 262 Days On Market

    Current Estimated Value $1,109,437

    Last Listing Agent Mickey Kiernan MICHAEL SAUNDERS & COMPANY

    5400 Ocean Blvd Unit 6-4, Sarasota, FL 34242
    • /85

      Est $3,024,054

      Not Listed For Sale

      5330 Siesta Cove Dr, Sarasota, FL 34242

      • 4 Beds
      • 4 Baths
      • 4,680 Sq Ft
      • Built 1977
      5330 Siesta Cove Dr, Sarasota, FL 34242

      Last Sold Summary

      • 95 Days On Market

      Last Listing Agent Denise Mei MICHAEL SAUNDERS & COMPANY

  • /16

    $29,995,000

    New Construction Under Contract
    • 7 Beds
    • 11 Baths
    • 13,035 Sq Ft

    3990 Higel Ave, Sarasota, FL 34242

    Under contract-accepting backup offers. Under Construction. Under contract. Seller is continuing to accept backup offers pursuant to a kick-out clause. Welcome to 3990 Higel Avenue, set to be completed in August of 2026 and can be offered fully furnished. Where architectural brilliance meets unrivaled luxury on Sarasota’s exclusive Gulf-front shores. 3990 Higel is 1 of 1. Having direct ocean

    Adnan Dedic COMPASS FLORIDA LLC

    3990 Higel Ave, Sarasota, FL 34242
  • /25

    $7,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242

    Starting at $255/night! Experience the ultimate beachfront getaway at Villa 40, a beautifully appointed 2-bedroom, 2-bathroom condo at Casa Mar, thoughtfully designed to accommodate up to six guests in comfort and style. This spacious retreat features a king bed in the primary bedroom, two twin beds in the second bedroom, and a queen air mattress for added flexibility. The fully equipped kitchen

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242
  • /2

    $1,565,000

    Sold Aug 25, 2026

    1325 Hidden Harbor Way, Sarasota, FL 34242

    • Land
    • 22,651 Sq Ft
    • $3,009,615 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 11 Days On Market

    Current Estimated Value $1,614,077

    Last Listing Agent Alin Zdroba PROPERTIO

    1325 Hidden Harbor Way, Sarasota, FL 34242
    • /2

      Est $1,008,440

      Not Listed For Sale

      627 Avenida Del Norte, Sarasota, FL 34242

      • 3 Beds
      • 4 Baths
      • 1,713 Sq Ft
      • Built 1949
      627 Avenida Del Norte, Sarasota, FL 34242

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Pamela Hembree LUXURY & BEACH REALTY INC

  • /41

    $1,500,000

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

    6146 Midnight Pass Rd Unit 12S, Sarasota, FL 34242

    Best beachfront value on Siesta Key!!!This second-floor condo features two bedrooms and two bathrooms, including a primary ensuite with a king-size bed and a guest bedroom. The interior offers a spacious living area, a formal dining space, and a fully equipped kitchen with granite countertops. Residents and guests can enjoy spectacular views of the Gulf of Mexico and sunsets from the private

    Joshua Beckmann BECKMANN REAL ESTATE

    6146 Midnight Pass Rd Unit 12S, Sarasota, FL 34242
  • /26

    $6,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Apartment for Rent

    1125 W Peppertree Dr Unit 705, Sarasota, FL 34242

    This property is a 30 night minimum.1125 - 705 is a high-rise unit, located on the Gulf-side of Midnight Pass, approx.175 yards away from Crescent beach.Open kitchen floor plan. Newly remodeled kitchen with stainless steel appliances. Dual sink vanity in the Master bathroom. 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 705, Sarasota, FL 34242
  • /2

    $585,000

    Sold Dec 01, 2025

    1080 W Peppertree Ln Unit 602A, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,163 Sq Ft
    • Built 1974

    Last Sold Summary

    • 16% Below List Price
    • $503/SF
    • 142 Days On Market

    Current Estimated Value $618,210

    Last Listing Agent Lisa Beach WATERSIDE REALTY LLC

    1080 W Peppertree Ln Unit 602A, Sarasota, FL 34242
    • /50

      Est $532,869

      Not Listed For Sale

      Unlisted Address

      • 2 Beds
      • 2 Baths
      • 1,010 Sq Ft
      • Built 1979
      Unlisted Address

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Steven McNally WATERSIDE REALTY LLC

  • /26

    $325,000

    $80K PRICE DROP
    • Studio
    • 1 Bath
    • 420 Sq Ft

    6006 Midnight Pass Rd Unit 48, Sarasota, FL 34242

    PRICE IMPROVEMENT! Private Beach Access and exceptional value on Siesta Key! Rare opportunity to own in highly desirable Casa Mar and create your own island retreat with outstanding value-add potential. This studio unit presents one of the most compelling opportunities to own on Siesta Key.The unit already features updated lower kitchen cabinetry, quartz countertops, and a stainless-steel

    Susan Beaver LPT REALTY, LLC

    6006 Midnight Pass Rd Unit 48, Sarasota, FL 34242
  • /33

    $6,000 Per Month

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

    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242

    Welcome to your slice of paradise in Gulf & Bay Club Bayside, a highly sought-after community located on beautiful Siesta Key, Florida. Professionally managed by Gulf Coast Vacation rentals, this first-floor 2-bedroom, 2-bathroom lakefront condo offers the perfect blend of coastal charm and resort-style living. From the moment you step inside, you’ll be greeted by a beachy, relaxed vibe that

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
  • /2

    $1,050,000

    Sold Jul 17, 2026

    5300 Ocean Blvd Unit 202, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,372 Sq Ft
    • Built 1973

    Last Sold Summary

    • 9% Below List Price
    • $765/SF
    • 157 Days On Market

    Current Estimated Value $1,067,613

    Last Listing Agent Diane Goodwin EXP REALTY LLC

    5300 Ocean Blvd Unit 202, Sarasota, FL 34242
    • /2

      Est $1,724,683

      Not Listed For Sale

      4820 Higel Ave, Sarasota, FL 34242

      • 4 Beds
      • 3 Baths
      • 2,672 Sq Ft
      • Built 1972
      4820 Higel Ave, Sarasota, FL 34242

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Ryan Skrzypkowski COLDWELL BANKER REALTY

  • /42

    $2,800,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 2,970 Sq Ft

    6907 Bochi Cir, Sarasota, FL 34242

    Under Construction. Discover La Linda, an exclusive collection ofeight custom-built, modern homes offering breathtaking Gulf views just off Ocean Boulevard. Nestled in the highly sought-after Siesta Key, theseelevated residences are crafted to the highest standards, featuring solid block construction on all levels, impact-resistant windows and doors, andprivate elevators for ultimate

    Jeremy Hartmark LPT REALTY, LLC

    6907 Bochi Cir, Sarasota, FL 34242
  • /25

    $27,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,164 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 26, Sarasota, FL 34242

    When only the best will do, Villa 26 at Aloha Kai is the perfect choice. Beautifully updated with meticulous attention to detail, this beachfront villa offers an ideal retreat where you can watch shorebirds, dolphins, and breathtaking sunsets from your private porch. The kitchen is a chef’s dream, while the bathrooms provide a spa-like experience for ultimate relaxation. Located on Siesta Key, a

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 26, Sarasota, FL 34242
  • /2

    $1,000,000

    Sold Jan 30, 2026

    5036 Higel Ave, Sarasota, FL 34242

    • Land
    • 15,246 Sq Ft
    • $2,857,143 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 8 Days On Market

    Current Estimated Value $1,024,602

    Last Listing Agent Diana Pomarico PALERMO REAL ESTATE PROF. INC.

    5036 Higel Ave, Sarasota, FL 34242
    • /2

      Est $795,364

      Not Listed For Sale

      631 Venice Ln, Sarasota, FL 34242

      • 3 Beds
      • 2 Baths
      • 1,453 Sq Ft
      • Built 1972
      631 Venice Ln, Sarasota, FL 34242

      Last Sold Summary

      • 209 Days On Market

      Last Listing Agent Kelly Rosenberg COLDWELL BANKER REALTY

  • /59

    $8,500,000

    • 4 Beds
    • 4.5 Baths
    • 5,649 Sq Ft

    1280 Hidden Harbor Way, Sarasota, FL 34242

    Privately positioned on a tropical peninsula on Siesta Key in the coveted community of Hidden Harbor, this extraordinary bayfront estate captures sweeping views across Sarasota Bay, the Intracoastal Waterway and the downtown Sarasota skyline. Set on 0.62 acres with 125 feet of panoramic waterfront, the residence was masterfully built by luxury builder M. L. Collingwood and thoughtfully designed

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1280 Hidden Harbor Way, Sarasota, FL 34242
  • /22

    $8,370 Per Month

    • 2 Beds
    • 1.5 Baths
    • 834 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 50, Sarasota, FL 34242

    Early risers and night owls can live in harmony at Villa 50 at Aloha Kai, where the thoughtful layout features bedrooms upstairs and a convenient bathroom downstairs. This beautifully renovated villa boasts new flooring, an updated kitchen with stainless steel appliances, granite countertops, and modern bathrooms. Whether you're enjoying a meal in the spacious dining room or dining al fresco on

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 50, Sarasota, FL 34242
  • /2

    $2,050,000

    Sold Apr 01, 2026

    518 Venice Ln, Sarasota, FL 34242

    • 3 Beds
    • 3 Baths
    • 2,676 Sq Ft
    • Built 1971

    Last Sold Summary

    • 11% Below List Price
    • $766/SF
    • 103 Days On Market

    Current Estimated Value $2,043,028

    Last Listing Agent Pamela Pileggi PREFERRED SHORE LLC

    518 Venice Ln, Sarasota, FL 34242
    • /52

      Est $664,306

      Not Listed For Sale

      4660 Ocean Blvd Unit O1, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1971
      4660 Ocean Blvd Unit O1, Sarasota, FL 34242

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Joel Schemmel DOUGLAS ELLIMAN

  • /27

    $729,500

    • 2 Beds
    • 1.5 Baths
    • 1,980 Sq Ft

    5955 Midnight Pass Rd Unit 21E, Sarasota, FL 34242

    Sea Club II -Only those looking for a relaxing, quiet and tranquil get-away with an "Old Florida" feel. Sea Club II has private access to Siesta Key beach sand and the Gulf of America, with a 5-minute walk down community path. This Unit is on the second floor with stair access only. Discover the beauty of Siesta Key from this superb 2-bedroom condo. One bedroom has a 1 king bed and one with a 1

    David Butler Jr RE/MAX ALLIANCE GROUP

    5955 Midnight Pass Rd Unit 21E, Sarasota, FL 34242
  • /64

    $2,450 Per Month

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

    446 Canal Rd Unit 5, Sarasota, FL 34242

    This is a short term (weekly) rental. Listing reflects peak season weekly rate. Discover Key Lime Retreat, an end-unit condo perfectly situated in the heart of Siesta Key. This delightful getaway combines comfort with modern style, ideal for families or a group of friends. Tucked away in a tropical garden setting, you'll enjoy access to a community pool, perfect for a refreshing dip. Everything

    Beth Dilley ASCENDIA REAL ESTATE

    446 Canal Rd Unit 5, Sarasota, FL 34242
  • /2

    $1,895,000

    Sold Mar 10, 2026

    5165 Sandy Cove Ave, Sarasota, FL 34242

    • 3 Beds
    • 2.5 Baths
    • 2,216 Sq Ft
    • Built 1964

    Last Sold Summary

    • 5% Below List Price
    • $855/SF
    • 72 Days On Market

    Current Estimated Value $1,873,265

    Last Listing Agent Darlene Gamble FINE PROPERTIES

    5165 Sandy Cove Ave, Sarasota, FL 34242
    • /68

      Est $891,914

      Not Listed For Sale

      5911 Midnight Pass Rd Unit 604, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,447 Sq Ft
      • Built 1984
      5911 Midnight Pass Rd Unit 604, Sarasota, FL 34242

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Shirley LaGrange COLDWELL BANKER REALTY

Showing Results 601 - 640, Page 16 of 18

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