Siesta Key, FL Homes

/32
$595,000
- 1 Bed
- 1 Bath
- 728 Sq Ft
5830 Midnight Pass Rd Unit 52, Sarasota, FL 34242

An investor’s dream! Discover unbeatable income potential with this fully renovated 1 bed, 1 bath condo at Jamaica Royale—a proven high-performing rental generating up to $58,000 annually and already secured with over $30,000 in bookings for 2026. Whether you're seeking a profitable income property, a personal beach retreat, or both, this turnkey unit is positioned to deliver.The spacious

Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

5830 Midnight Pass Rd Unit 52, Sarasota, FL 34242
/30
$6,100 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Condo for Rent
1255 E Peppertree Dr Unit 601, Sarasota, FL 34242

255-601 is a Bay-side Mid-rise unit, located approximately 75 yards away from the Bay.This unit does not have a bed in the guest bedroom, it will have a sleeper sofa. Open kitchen floor plan with stainless steel appliances. Open porch lanai. Guest bedroom TV is mounted on the wall. Dual sink vanity in the master bathroom, seat in the master bathroom shower. Assigned covered parking located in

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1255 E Peppertree Dr Unit 601, Sarasota, FL 34242
/2
$680,000 Sold Jun 12, 2025

1155 Lake House Cir Unit C119, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,352 Sq Ft
- Built 1981
Last Sold Summary
- $503/SF
- 8 Days On Market
Current Estimated Value $650,060

Last Listing Agent Jennifer Putnam COLDWELL BANKER SARASOTA CENT.

1155 Lake House Cir Unit C119, Sarasota, FL 34242

/2
Est $519,722 Not Listed For Sale
- 2 Beds
- 2 Baths
- 929 Sq Ft
1257 S Portofino Dr Unit 406, Sarasota, FL 34242

1257 S Portofino Dr Unit 406, Sarasota, FL 34242

/27
$639,000
- 1 Bed
- 1.5 Baths
- 728 Sq Ft
5830 Midnight Pass Rd Unit 63, Sarasota, FL 34242

Experience the best of Gulf-side living in this beautifully renovated 1-bed, 1.5-bath condo on Siesta Key — just steps from the world-famous quartz-sand beaches of Siesta Key. Completely updated from top to bottom, this turnkey coastal retreat features brand-new designer furniture and appliances, making it move-in or rental-ready from the moment you arrive. The spacious layout includes a highly

Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

5830 Midnight Pass Rd Unit 63, Sarasota, FL 34242
/19
$5,500 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Condo for Rent
1255 E Peppertree Dr Unit 501, Sarasota, FL 34242

Welcome to this beautifully remodeled Bayside Mid-rise unit. This spacious 2-bedroom, 2-bathroom condo is situated on the 5th floor, As you step inside, you'll be greeted by a tastefully decorated living area with modern furnishings and a serene coastal color palette. The open-concept design seamlessly connects the living, dining, and kitchen areas, creating a perfect space for relaxation and

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1255 E Peppertree Dr Unit 501, Sarasota, FL 34242
/2
$729,000 Sold Oct 17, 2025

1240 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 $718,288

Last Listing Agent Gina LaRouche COLDWELL BANKER REALTY

1240 Siesta Bayside Dr Unit 1240C, Sarasota, FL 34242

/77
Est $666,607 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
6145 Midnight Pass Rd Unit F-1, Sarasota, FL 34242

6145 Midnight Pass Rd Unit F-1, Sarasota, FL 34242

/73
$6,400,000
- 5 Beds
- 7 Baths
- 6,928 Sq Ft
5132 Jungle Plum Rd, Sarasota, FL 34242

Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm

Joel Schemmel DOUGLAS ELLIMAN

5132 Jungle Plum Rd, Sarasota, FL 34242
/15
$6,500 per month
- 2 Beds
- 2 Baths
- 1,105 Sq Ft
- Condo for Rent
1255 E Peppertree Dr Unit 101, Sarasota, FL 34242

This property is a 30 night minimum.This 2 bedroom, 2 bath is located on the first floor in a bay-side mid-rise and is approximately 75 yards from the Bay.The master bedroom has a king bed, a 20 inch TV, a ceiling fan, and access to the extended living lanai. The updated master bathroom has new finishes and a walk-in glass door shower with a removable shower head.The guest bedroom has

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1255 E Peppertree Dr Unit 101, Sarasota, FL 34242
/2
$460,000 Sold Dec 04, 2025

5649 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
Last Listing Agent Janet Trefry RE/MAX ALLIANCE GROUP

5649 Midnight Pass Rd Unit 804, Sarasota, FL 34242

/66
Est $560,086 Not Listed For Sale
- 1 Bed
- 1 Bath
- 561 Sq Ft
23 Sandy Cove Rd Unit B1-G, Sarasota, FL 34242

23 Sandy Cove Rd Unit B1-G, Sarasota, FL 34242

/66
$790,000
- 2 Beds
- 1.5 Baths
- 840 Sq Ft
6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242

Welcome to your Siesta Key Beach escape at 6006 Midnight Pass Rd, Unit 44! This charming, fully furnished 2-bedroom condo places you steps from the world-famous powdery white sands and turquoise waters of Siesta Key Beach. Enjoy direct private beach access, breathtaking Gulf views, and endless sunsets right from this coveted coastal community. Inside, an open and inviting layout features vaulted

Michael Mitchell MITCHELL REAL ESTATE

6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242
/22
$6,000 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Condo for Rent
1255 E Peppertree Dr Unit 403, Sarasota, FL 34242

This property is a 30 night minimum.This stunning, updated 2 bedroom, 2 bath is located in a bay-side mid-rise unit and is approximately 75 yards from the bay.The master bedroom has a king bed, a TV, and pocket sliding glass doors that gives access to the extended lanai living. The master bathroom has a walk-in glass door shower with grab bars and a beautiful granite vanity.The guest

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1255 E Peppertree Dr Unit 403, Sarasota, FL 34242
/2
$800,000 Sold Dec 19, 2025

6300 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
Last Listing Agent Mike Warm PREMIER SOTHEBY'S INTERNATIONAL REALTY

6300 Midnight Pass Rd Unit 2, Sarasota, FL 34242

/41
Est $662,147 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,016 Sq Ft
141 Avenida Messina Unit 3, Sarasota, FL 34242

141 Avenida Messina Unit 3, Sarasota, FL 34242

/51
$2,295,000
- 3 Beds
- 3 Baths
- 2,676 Sq Ft
518 Venice Ln, Sarasota, FL 34242

ELEGANT SIESTA KEY WATERFRONT RETREAT - Welcome to a truly distinguished canal-front residence, where timeless design meets the effortless beauty of waterfront living. Set beneath majestic oaks and tropical landscaping, the canopied circular paver driveway greets you. This exquisite pool home offers privacy, sophistication and an extraordinary outdoor lifestyle. An avid boater's dream with 110

Pamela Pileggi PREFERRED SHORE LLC

518 Venice Ln, Sarasota, FL 34242
/26
$7,000 per month
- 2 Beds
- 11 Baths
- 1,163 Sq Ft
- Condo for Rent
1200 E Peppertree Ln Unit 602, Sarasota, FL 34242

This property is a 30 night minimum.1200-602 is a Penthouse unit in a Bay-side Mid-rise, located approximately 150 yards away from the Bay with a view of the waterway and downtown Sarasota in the distance. Approx. 1200 Sq. Ft. (1462 including the lanai)Lanai has a twin daybed with a trundle, eating area, and desk setup for remote work. Assigned covered parking located in parking garage

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1200 E Peppertree Ln Unit 602, Sarasota, FL 34242
/2
$4,000,000 Sold Jun 26, 2025

645 Beach Rd, Siesta Key, FL 34242
- 4,989 Sq Ft
- Built 2018
Last Sold Summary
- 19% Below List Price
- $802/SF
- 441 Days On Market
Current Estimated Value $4,789,575

Last Listing Agent Cole Collins COLDWELL BANKER REALTY

645 Beach Rd, Siesta Key, FL 34242

/2
Est $921,702 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,660 Sq Ft
1315 Siesta Bayside Dr Unit B, Sarasota, FL 34242

1315 Siesta Bayside Dr Unit B, Sarasota, FL 34242

/41
$699,000 Pending
- 2 Beds
- 2 Baths
- 1,204 Sq Ft
1001 Beach Rd Unit A203, Sarasota, FL 34242

Under contract-accepting backup offers. Price Drop of 20K - best price for a Tower Unit in Our House at the Beach !Strong Rental Income – Across from Siesta Beach! Totally updated 2 bed / 2 bath condo in the West Tower of “Our House at the Beach”, directly across from Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor in 2024. This second-floor unit offers incredible natural light and nearly

Mike Winger TIDELINE REAL ESTATE BROKERS

1001 Beach Rd Unit A203, Sarasota, FL 34242
/18
$6,500 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Condo for Rent
1255 E Peppertree Dr Unit 305, Sarasota, FL 34242

his property is a 30 night minimum.1255 - 305 is a Bay-side Mid-rise unit, located approximately 75 yards away from the Bay.Open kitchen floor plan. Dual sink vanity in Master bathroom. Living room has a sleeper sofa available. Condo is located on third floor. Equipped with Xfinity cable service and free Wi-Fi. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft.

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1255 E Peppertree Dr Unit 305, Sarasota, FL 34242
/2
$1,200,000 Sold Apr 25, 2025

5602 Cape Leyte Dr, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 2,111 Sq Ft
- Built 1960
Last Sold Summary
- 9% Below List Price
- $568/SF
- 50 Days On Market
Current Estimated Value $1,124,564

Last Listing Agent Ben Angerami PREMIER SOTHEBY'S INTERNATIONAL REALTY

5602 Cape Leyte Dr, Sarasota, FL 34242

/68
Est $546,164 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1600 Cove II Place Unit 421, Sarasota, FL 34242

1600 Cove II Place Unit 421, Sarasota, FL 34242

/56
$2,190,000
- 3 Beds
- 2.5 Baths
- 2,233 Sq Ft
5155 Hidden Harbor Rd, Sarasota, FL 34242

Nearly 200 feet of deep-water frontage in the prestigious Hidden Harbor enclave of Siesta Key—no bridges, quick access to Roberts Bay and the Gulf of America. Move-in ready and never flooded.Enjoy island living in this private waterfront setting surrounded by multi-million dollar estates. Lush, canopy-lined brick paver streets, wide water views, no through streets, and excellent boating

Matt Buttner LIST NOW REALTY, LLC

5155 Hidden Harbor Rd, 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
$1,500,000 Sold Dec 01, 2025

1038 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
Last Listing Agent Sara Leicht SARASELLSSARASOTA.COM

1038 Contento St, Sarasota, FL 34242

/42
Est $775,846 Not Listed For Sale
- 1 Bed
- 1 Bath
- 816 Sq Ft
5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242

5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242

/67
$3,500,000 Pending
- 3 Beds
- 3 Baths
- 3,471 Sq Ft
5058 Windward Ave, Siesta Key, FL 34242

Under contract-accepting backup offers. This custom-built home received the “Best Overall” award in the 2021 Manatee and Sarasota County Parade of Homes. Experience the pinnacle of Siesta Key waterfront living in this 2019-built masterpiece by Nutter Custom Construction. Designed with precision and built to last, this solar-powered coastal retreat sits on high elevation and spans over 3,400

Derek Edwards KELLER WILLIAMS ON THE WATER S

5058 Windward Ave, Siesta Key, FL 34242
/10
$8,340 per month
- 2 Beds
- 2 Baths
- 1,064 Sq Ft
- House for Rent
6154 Midnight Pass Rd Unit C06, Sarasota, FL 34242

C6 is a lovely unit, has been remodeled and is awaiting your arrival. It can accommodate up to 6. The spacious living room/dining room has all new furniture, including a large couch, two recliners, coffee, and end tables. In the dining area you will find a new dining table and chairs and a ceiling fan. There is also a wall-mounted 55” UHD Smart TV. The very large Master Bedroom has a king-size

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6154 Midnight Pass Rd Unit C06, Sarasota, FL 34242
/2
$3,300,000 Sold Apr 10, 2025

317 Beach Rd, Sarasota, FL 34242
- 4 Beds
- 3.5 Baths
- 3,362 Sq Ft
- Built 2009
Last Sold Summary
- 6% Below List Price
- $982/SF
- 14 Days On Market
Current Estimated Value $3,272,093

Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

317 Beach Rd, Sarasota, FL 34242

/43
Est $675,784 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,270 Sq Ft
5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242

5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242

/59
$730,000
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
5855 Midnight Pass Rd Unit 520, Sarasota, FL 34242

Wow, WHAT A VIEW! Gulf and sunset views from both bedrooms and the living room of this 5th-floor condo. Beautifully turnkey furnished, this large 2 bedroom, 2 bath condo boasts a double master layout, an extended living room/sunroom, and a gorgeously updated kitchen with stainless steel appliances and granite counter tops. Both bathrooms have also been exquisitely updated to maximize space and

Shana Hamel NEXTHOME EXCELLENCE

5855 Midnight Pass Rd Unit 520, Sarasota, FL 34242
/14
$8,970 per month
- 2 Beds
- 2 Baths
- 1,064 Sq Ft
- House for Rent
6154 Midnight Pass Rd Unit B02, Sarasota, FL 34242

Find your Happy Place here in this LARGE 2 bedroom/2 bathroom, private entrance villa. There is new granite in the kitchen which is fully equipped. The master bedroom is furnished with a king size bed. The master vanity for the ladies comes with a hairdryer. The master bath features a walk-in shower with new tile and granite, all new from top to bottom. The second bedroom provides two double

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6154 Midnight Pass Rd Unit B02, Sarasota, FL 34242
/2
$425,000 Sold Sep 11, 2025

6029 E Peppertree Way Unit 116, Sarasota, FL 34242
- 2 Beds
- 1.5 Baths
- 975 Sq Ft
- Built 1973
Last Sold Summary
- 27% Below List Price
- $436/SF
- 234 Days On Market
Current Estimated Value $435,356

Last Listing Agent Cheryl Santelli PEPPERTREE BAY REALTY INC

6029 E Peppertree Way Unit 116, Sarasota, FL 34242

/73
Est $629,472 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,259 Sq Ft
5600 Beach Way Dr Unit 215, Sarasota, FL 34242

5600 Beach Way Dr Unit 215, Sarasota, FL 34242

/60
$2,900,000
- 4 Beds
- 4.5 Baths
- 4,254 Sq Ft
5236 Siesta Cove Dr, Sarasota, FL 34242

No Hurricane or Flood Damage. A coastal modern oasis in Siesta Cove, Siesta Key’s premier neighborhood, highlights 80 feet of waterfront with convenient boat access to Gulf and Bay, with newer seawall, boat dockage, and an extraordinary pool that invites you to enjoy Siesta Key’s relaxed lifestyle. Breathtaking Sarasota Bay vistas along the many peaceful panoramic patio terraces provide endless

Bradley Kayser COLDWELL BANKER REALTY

5236 Siesta Cove Dr, Sarasota, FL 34242
/10
$7,500 per month
- 2 Beds
- 1 Bath
- 941 Sq Ft
- House for Rent
6154 Midnight Pass Rd Unit C05, 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 C05, Sarasota, FL 34242
/2
$1,000,000 Sold May 12, 2025

Unlisted Address
- 3 Beds
- 2 Baths
- 2,049 Sq Ft
- Built 1952
Last Sold Summary
- 13% Below List Price
- $488/SF
- 6 Days On Market
Current Estimated Value $969,908

Last Listing Agent Frederick Insogna COLDWELL BANKER REALTY

Unlisted Address

/45
Est $600,547 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
5963 Midnight Pass Rd Unit 359, Sarasota, FL 34242

5963 Midnight Pass Rd Unit 359, Sarasota, FL 34242

Showing Results 121 - 160, Page 4 of 18

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