Homes in ZIP Code 34242

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  /37

  $6,000,000

  • 5 Beds
  • 7 Baths
  • 4,496 Sq Ft

  5507 Calle Del Invierno, Sarasota, FL 34242

  There is only one – The Lookout. Effortlessly close to everything yet a world apart, this modern Siesta Key estate embodies the essence of the Vunique Homes experience—architectural artistry, intentional design, and a lifestyle defined by luxury and ease. Steps from Siesta Key Beach and the vibrant Siesta Village, this turnkey furnished residence is ideally positioned for those who value

  Rudy Dudon MICHAEL SAUNDERS & COMPANY

  5507 Calle Del Invierno, Sarasota, FL 34242
• 

  

  

  /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

  $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

  Current Estimated Value $856,375

  Last Listing Agent Curtis Ware KW COASTAL LIVING III

  5780 Midnight Pass Rd Unit 303, Sarasota, FL 34242
• 

  

  

  /51

  Est $546,975 Not Listed For Sale

  9000 Blind Pass Rd Unit B303, Sarasota, FL 34242

  • 1 Bed
  • 1.5 Baths
  • 750 Sq Ft
  • Built 1968

  9000 Blind Pass Rd Unit B303, Sarasota, FL 34242

  Last Sold Summary

  • 25% Below List Price
  • $967/SF
  • 166 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Keith Redding WILLIAM RAVEIS REAL ESTATE
• 

  

  

  /60

  $3,850,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,122 Sq Ft

  5263 Avenida de Cortez, Sarasota, FL 34242

  Welcome to a residence where inspired design meets the effortless elegance of Island living. Tucked away on the tranquil side of the Siesta Key Village, this extraordinary home places you at the heart of it all while having it all. With World-renowned beaches and the charming village just steps away... you truly can not beat the location. This 4 bedroom, 3100 sq.ft. home boasts a private boat

  Jessica Hoffman COLDWELL BANKER REALTY

  5263 Avenida de Cortez, 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

  $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

  Current Estimated Value $651,560

  Last Listing Agent Mary Beth Hudson COLDWELL BANKER REALTY

  5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242
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  /44

  Est $727,726 Not Listed For Sale

  9000 Blind Pass Rd Unit B106, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • Built 1968

  9000 Blind Pass Rd Unit B106, Sarasota, FL 34242

  Last Sold Summary

  • 23% Below List Price
  • $872/SF
  • 149 Days On Market

  Last Sold Price $950,000

  Last Listing Agent Keith Redding WILLIAM RAVEIS REAL ESTATE
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  /61

  $2,590,000

  • 4 Beds
  • 3.5 Baths
  • 3,228 Sq Ft

  467 Canal Rd Unit 467, Sarasota, FL 34242

  Possible Seller Finance. High & Dry!! BEACH, BOATING & BISTROS!!!! SIESTA KEY`CANAL FRONT featuring WEEKLY RENTALS!! DOCK & LIFT!! GULF VIEWS!! BEACH ACCESS STEPS AWAY!!! Great location with Gulf Views steps to Public Beach Access #8 offering the ultimate waterfront lifestyle of this rare, furnished 3 bedroom/3.5 Bath plus office (or 4th bedroom), RMF-zoned opportunity on Siesta Key. Built in

  Dan Miller PREFERRED SHORE LLC

  467 Canal Rd Unit 467, 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

  $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

  Current Estimated Value $1,227,143

  Last Listing Agent Jason Skowronski COMPASS FLORIDA LLC

  307 Avenida de Paradisio, Sarasota, FL 34242
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  /24

  Est $1,337,444 Not Listed For Sale

  8750 Midnight Pass Rd Unit 502C, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 2,276 Sq Ft
  • Built 1980

  8750 Midnight Pass Rd Unit 502C, Sarasota, FL 34242

  Last Sold Summary

  • 14% Below List Price
  • $681/SF
  • 276 Days On Market

  Last Sold Price $1,550,000

  Last Listing Agent Mark Kessler PHELPS REALTY GROUP
• 

  

  /99

  $690,000

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft

  797 Beach Rd Unit 509, Sarasota, FL 34242

  PENTHOUSE" OPPORTUNITY on the 5th Floor of Building 797 in Sought After & Gated CRESCENT ROYALE! As you walk through the door you will be astounded with the beautiful views of the Gulf of Mexico & Siesta Beach! Own your own piece of Siesta Key and enjoy the gorgeous nightly sunsets on the top floor. This updated unit has been well maintained and tastefully furnished, updated with a functional

  Sandy Gamble Hulvat WATERSIDE REALTY LLC

  797 Beach Rd Unit 509, 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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  /2

  $1,500,000 Sold Mar 17, 2026

  7320 Melaleuca Way, Sarasota, FL 34242

  • 4 Beds
  • 4 Baths
  • 2,970 Sq Ft
  • Built 1960

  Last Sold Summary

  • 14% Below List Price
  • $505/SF
  • 279 Days On Market

  Last Listing Agent Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

  7320 Melaleuca Way, Sarasota, FL 34242
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  /40

  Est $604,440 Not Listed For Sale

  8750 Midnight Pass Rd Unit 106C, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1980

  8750 Midnight Pass Rd Unit 106C, Sarasota, FL 34242

  Last Sold Summary

  • 7% Below List Price
  • $394/SF
  • 453 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Mina Johnson Michael Saunders
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  /71

  $3,999,000

  • 4 Beds
  • 5 Baths
  • 4,006 Sq Ft

  7647 Sanderling Rd, Sarasota, FL 34242

  A Sarasota School of Architecture residence in the historic Sanderling Club. Tucked behind the gates of the historic Sanderling Club on the serene southern end of Siesta Key, this remarkable waterfront residence offers a rare opportunity to experience one of Florida’s celebrated architectural traditions. Set on nearly an acre along the tranquil waters of Heron Lagoon, the home reflects the

  Janet Moore PREMIER SOTHEBY'S INTL REALTY

  7647 Sanderling Rd, 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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  /2

  $325,000 Sold Dec 31, 2025

  101 Whispering Sands Dr Unit 205, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft
  • Built 1969

  Last Sold Summary

  • 19% Below List Price
  • $256/SF
  • 25 Days On Market

  Current Estimated Value $443,220

  Last Listing Agent Julie Froeschle BERKSHIRE HATHAWAY HOMESERVICE

  101 Whispering Sands Dr Unit 205, Sarasota, FL 34242
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  /72

  Est $714,404 Not Listed For Sale

  8750 Midnight Pass Rd Unit 103C, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1980

  8750 Midnight Pass Rd Unit 103C, Sarasota, FL 34242

  Last Sold Summary

  • 14% Below List Price
  • $503/SF
  • 241 Days On Market

  Last Sold Price $830,000

  Last Listing Agent Lori Madden MANGROVE REALTY ASSOCIATES
• 

  

  /21

  $949,900

  • 4 Beds
  • 4 Baths
  • 2,709 Sq Ft

  617 Siesta Dr, Sarasota, FL 34242

  BANK OWNED... Located in Highly desirable Bay Island Subdivision The Gateway to Siesta Key ... This 2700 sqft Tropical Island Getaway offers 4-5 bedrooms 4 bath property locating within the City limits on Siesta Key which allows short time rentals. Upgrades include Metal roof with solar panels, Crown Molding, and Brick paver Driveway. This property was Flooded during the 2024 Hurricanes and

  Gary Hoskins COLDWELL BANKER REALTY

  617 Siesta Dr, 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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  /2

  $624,500 Sold Jan 12, 2026

  9397 Midnight Pass Rd Unit 906, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,338 Sq Ft
  • Built 1975

  Last Sold Summary

  • 7% Below List Price
  • $467/SF
  • 281 Days On Market

  Current Estimated Value $621,182

  Last Listing Agent Jennifer Thompson WILLIAM RAVEIS REAL ESTATE

  9397 Midnight Pass Rd Unit 906, Sarasota, FL 34242
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  /63

  Est $1,998,261 Not Listed For Sale

  8710 Midnight Pass Rd Unit 400B, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 2,614 Sq Ft
  • Built 1980

  8710 Midnight Pass Rd Unit 400B, Sarasota, FL 34242

  Last Sold Summary

  • 27% Below List Price
  • $1,052/SF
  • 54 Days On Market

  Last Sold Price $2,750,000

  Last Listing Agent Eliza Miller PEPPERTREE BAY REALTY INC
• 

  

  /75

  $1,125,000

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft

  19 Whispering Sands Dr Unit 1104, Sarasota, FL 34242

  PRICE IMPROVEMENT!! Welcome to this beautifully remodeled 11th floor GULF FRONT Whispering Sands tower residence – just one floor below the penthouse level – where sweeping, unobstructed FULL Gulf views meet breathtaking, colorful sunsets that paint the sky each evening. This light filled 2BR/2BA condo is the perfect combination of refined coastal style with effortless, comfortable living. The

  Harriet Stopher COLDWELL BANKER REALTY

  19 Whispering Sands Dr Unit 1104, Sarasota, FL 34242
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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

  $1,259,000 Sold Jul 16, 2025

  20 Whispering Sands Dr Unit 406, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 1973

  Last Sold Summary

  • 10% Below List Price
  • $982/SF
  • 61 Days On Market

  Current Estimated Value $1,178,198

  Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

  20 Whispering Sands Dr Unit 406, Sarasota, FL 34242
• 

  

  /50

  Est $788,119 Not Listed For Sale

  8730 Midnight Pass Rd Unit 304A, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,445 Sq Ft
  • Built 1980

  8730 Midnight Pass Rd Unit 304A, Sarasota, FL 34242

  Last Sold Summary

  • 15% Below List Price
  • $639/SF
  • 130 Days On Market

  Last Sold Price $924,000

  Last Listing Agent Tricia Rudd KELLER WILLIAMS ON THE WATER S
• 

  

  /38

  $1,375,000

  • 3 Beds
  • 3 Baths
  • 1,783 Sq Ft

  8555 Heron Lagoon Cir, Sarasota, FL 34242

  Rare Opportunity on Siesta Key – Expansive Corner Lot with Private Beach Access!Unlock the potential of this over 3⁄4-acre corner lot with private beach access, nestled on the world-renowned Siesta Key! This is truly a once-in-a-lifetime chance to secure one of the largest privately owned parcels on Siesta Key. The home on the property has been cleared and now the lot is ready for you to

  Conner Ashley PREFERRED SHORE LLC

  8555 Heron Lagoon Cir, Sarasota, FL 34242
• 

  

  /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

  $990,000 Sold Apr 03, 2025

  5159 Oakmont Place, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,953 Sq Ft
  • Built 1977

  Last Sold Summary

  • 6% Below List Price
  • $507/SF
  • 47 Days On Market

  Current Estimated Value $966,337

  Last Listing Agent Jenni Burnette COLDWELL BANKER REALTY

  5159 Oakmont Place, Sarasota, FL 34242
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  /87

  Est $446,800 Not Listed For Sale

  8730 Midnight Pass Rd Unit 302A, Sarasota, FL 34242

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Built 1980

  8730 Midnight Pass Rd Unit 302A, Sarasota, FL 34242

  Last Sold Summary

  • 10% Below List Price
  • $624/SF
  • 25 Days On Market

  Last Sold Price $499,000

  Last Listing Agent Dawn Bear WILLIAM RAVEIS REAL ESTATE
• 

  

  /27

  $895,000

  • Land
  • 0.26 Acre
  • $3,442,308 per Acre

  8504 Heron Lagoon Cir, Sarasota, FL 34242

  Have you ever built a bonfire on the beach and had 50 of your closest family and friends over for a beach party? This happens no where else on Siesta Key. Residents in the neighborhood enjoy the unique privilege of crossing Heron Lagoon via a private bridge to the sands of Siesta Key beach. There’s a cabana for storing your beach chairs, kayaks and water toys. It’s a one minute walk from your

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  8504 Heron Lagoon Cir, Sarasota, FL 34242
• 

  

  /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

  $700,000 Sold Dec 08, 2025

  4637 Ocean Blvd, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 2,065 Sq Ft
  • Built 1952

  Last Sold Summary

  • 20% Below List Price
  • $339/SF
  • 73 Days On Market

  Current Estimated Value $712,985

  Last Listing Agent Albert Wooster ALBERT WOOSTER & COMPANY

  4637 Ocean Blvd, Sarasota, FL 34242
• 

  

  /58

  Est $585,794 Not Listed For Sale

  8730 Midnight Pass Rd Unit 203A, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Built 1980

  8730 Midnight Pass Rd Unit 203A, Sarasota, FL 34242

  Last Sold Summary

  • 14% Below List Price
  • $674/SF
  • 182 Days On Market

  Last Sold Price $682,000

  Last Listing Agent Maria Beck Michael Saunders
• 

  

  /53

  $4,650,000

  • 4 Beds
  • 3.5 Baths
  • 2,518 Sq Ft

  1035 Seaside Dr Unit 503, Sarasota, FL 34242

  One-of-a-Kind Gulf-Front Luxury at Ten35 Seaside! Welcome to Unit #503—an extraordinary, custom-designed Gulf-front residence on South Siesta Key. Thoughtfully reimagined with over $400,000 in bespoke upgrades, this one-of-a-kind home delivers a level of luxury, craftsmanship, and exclusivity rarely offered. From the moment you arrive, convenience meets prestige with two deeded parking spaces and

  David Lehrman THE SARASOTA REAL ESTATE COMP.

  1035 Seaside Dr Unit 503, Sarasota, FL 34242
• 

  

  /14

  $8,000 per month

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

  1125 W Peppertree Dr Unit 202, Sarasota, FL 34242

  Second-Floor Condo in Sought-After Peppertree Bay. 30 day minimum stay. Starting between $250-$347/night!Welcome to this beautifully maintained second-floor condo located in the highly desirable Peppertree Bay community on Siesta Key. Offering a tranquil pond view, this residence provides a peaceful coastal retreat just steps from the Gulf.The condo features a full kitchen equipped with

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 202, Sarasota, FL 34242
• 

  /2

  $625,000 Sold Feb 20, 2026

  6150 Midnight Pass Rd Unit 26, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,101 Sq Ft
  • Built 1967

  Last Sold Summary

  • 11% Below List Price
  • $568/SF
  • 54 Days On Market

  Current Estimated Value $690,050

  Last Listing Agent Linda Stowe MICHAEL SAUNDERS & COMPANY

  6150 Midnight Pass Rd Unit 26, Sarasota, FL 34242
• 

  

  /45

  Est $536,712 Not Listed For Sale

  8635 Midnight Pass Rd Unit C207, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,115 Sq Ft
  • Built 1970

  8635 Midnight Pass Rd Unit C207, Sarasota, FL 34242

  Last Sold Summary

  • 2% Below List Price
  • $493/SF
  • 16 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Claude Pierre CP REALTY INTERNATIONAL

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