Siesta Key, FL Homes

/53
$1,950,000
- 3 Beds
- 3 Baths
- 2,882 Sq Ft
951 Contento St, Sarasota, FL 34242

New pricing! Deep boating water on the Grand Canal and Siesta Key’s world-famous beaches just minutes away, experience the best of island living. This beautifully renovated three-bedroom, three-bath waterfront residence offers a peaceful island retreat with nearly 2,900 square feet of living space plus a private office, ideal for everyday living and entertaining. On a quiet cul-de-sac in the

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

951 Contento St, Sarasota, FL 34242
/55
$5,000 Per Month
- 3 Beds
- 2.5 Baths
- 2,080 Sq Ft
- House for Rent
4946 Commonwealth Dr, Sarasota, FL 34242

Available as a monthly rental in May, August, September, October, November and December 2026 only!Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key canal. From the moment you arrive, you'll feel the world melt away as you step into this ultimate beach house getaway designed for relaxation and fun.

Beth Dilley ASCENDIA REAL ESTATE

4946 Commonwealth Dr, Sarasota, FL 34242
/2
$762,000 Sold Jan 14, 2026

4894 Oxford Dr, Sarasota, FL 34242
- 3 Beds
- 2.5 Baths
- 1,831 Sq Ft
- Built 1967
Last Sold Summary
- 13% Below List Price
- $416/SF
- 63 Days On Market
Current Estimated Value $774,096

Last Listing Agent Marc Overfelt FLORIDA BAY REALTY INC

4894 Oxford Dr, Sarasota, FL 34242

/2
Est $886,589 Not Listed For Sale

6145 Midnight Pass Rd Unit F6, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,212 Sq Ft
- Built 1968
6145 Midnight Pass Rd Unit F6, Sarasota, FL 34242

Last Sold Summary
- 3% Below List Price
- $751/SF
- 129 Days On Market
- Last Sold Price $910,000
- Sep 03, 2024
Last Listing Agent Suki Scollo COLDWELL BANKER REALTY

/48
$1,095,000 Pending
- 3 Beds
- 2 Baths
- 1,808 Sq Ft
1002 Glebe Ln, Sarasota, FL 34242

Under contract-accepting backup offers. New price! Beautifully remodeled and ideally just minutes from world-renowned white sands of Siesta Beach, this chic island pool home offers an exceptional blend of style, comfort, and storm-ready peace of mind. Designed for effortless coastal living, the open main living area is highlighted by a vaulted ceiling, transom windows, and abundant natural light,

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

1002 Glebe Ln, Sarasota, FL 34242
/36
$9,500 Per Month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242

Welcome to your elevated sanctuary in paradise – a second-floor two-bedroom condo at Gulf & Bay Bayside on the enchanting Siesta Key, Florida. Upon entering, you're immediately greeted by an open-concept living space that seamlessly integrates the interior with the scenic beauty beyond. The living area, adorned with coastal-inspired décor, invites you to relax in comfort while large

Andy Moore GULF COAST REALTY & MANAGEMENT

1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242
/2
$625,000 Sold Oct 24, 2025

199 Whispering Sands Dr Unit 105, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,557 Sq Ft
- Built 1970
Last Sold Summary
- 8% Below List Price
- $401/SF
- 62 Days On Market
Current Estimated Value $613,711

Last Listing Agent Tracy Srodes FINE PROPERTIES

199 Whispering Sands Dr Unit 105, Sarasota, FL 34242

/63
Est $658,097 Not Listed For Sale

6145 Midnight Pass Rd Unit F3, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
- Built 1968
6145 Midnight Pass Rd Unit F3, Sarasota, FL 34242

Last Sold Summary
- 9% Below List Price
- $681/SF
- 83 Days On Market
- Last Sold Price $727,000
- Oct 05, 2023
Last Listing Agent Suki Scollo COLDWELL BANKER REALTY

/56
$1,135,000
- 2 Beds
- 2 Baths
- 1,365 Sq Ft
1080 W Peppertree Ln Unit 305A, Sarasota, FL 34242

Rarely available beach-view residence with deeded access to the renowned shores of Siesta Key Beach. Located on the third floor, this bright and inviting unit features a versatile layout, including a pull-out sofa on the lanai with a privacy partition—perfect for creating a comfortable third sleeping area for guests.The well-designed split floor plan offers a spacious dining area, an eat-in

Eliza Miller PEPPERTREE BAY REALTY INC

1080 W Peppertree Ln Unit 305A, Sarasota, FL 34242
/27
$12,600 Per Month
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
- House for Rent
301 Avenida Madera Unit A, Sarasota, FL 34242

If you’re searching for the perfect location for your next vacation, your search ends here!This beautifully updated 2-bedroom, 2-bath home is ideally situated in the heart of Siesta Key, within Siesta Key Village and just a few blocks from the world-famous Siesta Key Beach. Designed with a bright coastal theme, the home features an inviting open layout and a fully updated kitchen with solid

Robert Bevington SHOWTIME REALTY

301 Avenida Madera Unit A, Sarasota, FL 34242
/2
$482,500 Sold Jun 06, 2025

5643 Midnight Pass Rd Unit 909, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,012 Sq Ft
- Built 1975
Last Sold Summary
- 3% Below List Price
- $477/SF
- 7 Days On Market
Current Estimated Value $471,126

Last Listing Agent Linda Williams GULF SHORES REALTY ERA POWERED

5643 Midnight Pass Rd Unit 909, Sarasota, FL 34242

/2
Est $1,749,566 Not Listed For Sale

1660 Summerhouse Ln Unit 701, Sarasota, FL 34242
- 3 Beds
- 3.5 Baths
- 2,490 Sq Ft
- Built 2007
1660 Summerhouse Ln Unit 701, Sarasota, FL 34242

Last Sold Summary
- 4% Below List Price
- $733/SF
- 328 Days On Market
- Last Sold Price $1,825,000
- Jan 15, 2025
Last Listing Agent Mel Goldsmith Michael Saunders

/40
$469,900
- 2 Beds
- 2 Baths
- 1,012 Sq Ft
5661 Midnight Pass Rd Unit 401, Sarasota, FL 34242

Welcome to coastal living at its best in White Sands Village, a desirable waterfront community ideally located in the middle of Siesta Key and 1 mile from The Village. This charming 2-bedroom, 2-bath end-unit condominium (no flood damage), offering added peace of mind and ease of ownership. The community is surrounded by lush tropical landscaping and features a clubhouse and sparkling community

Lisa Blakeney COLDWELL BANKER REALTY

5661 Midnight Pass Rd Unit 401, Sarasota, FL 34242
/13
$7,470 Per Month
- 1 Bed
- 1 Bath
- 572 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 32, Sarasota, FL 34242

Villa 32 at Aloha Kai is ideally located on Siesta Key, a beloved barrier island along Florida’s beautiful West Coast. This cozy unit features 1 bedroom, 1 bathroom, and includes the convenience of an in-unit washer and dryer. Aloha Kai is a family-friendly, gated resort community nestled in the heart of Crescent Beach—consistently ranked the number one beach in the continental United States.

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 32, Sarasota, FL 34242
/2
$860,000 Sold Oct 03, 2025

1055 Beach Rd Unit B302, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,204 Sq Ft
- Built 1981
Last Sold Summary
- 7% Below List Price
- $714/SF
- 262 Days On Market
Current Estimated Value $848,663

Last Listing Agent Michele Tanner PREFERRED SHORE LLC

1055 Beach Rd Unit B302, Sarasota, FL 34242

/60
Est $1,314,402 Not Listed For Sale

1660 Summerhouse Ln Unit 302, Sarasota, FL 34242
- 3 Beds
- 2.5 Baths
- 2,110 Sq Ft
- Built 2007
1660 Summerhouse Ln Unit 302, Sarasota, FL 34242

Last Sold Summary
- 6% Below List Price
- $664/SF
- 175 Days On Market
- Last Sold Price $1,400,000
- Oct 24, 2023
Last Listing Agent Stacy Liljeberg Michael Saunders

/77
$1,700,000 Pending
- 3 Beds
- 3 Baths
- 1,920 Sq Ft
915 Seaside Dr Unit 604, Sarasota, FL 34242

Live in it, rent it or enjoy the best of both worlds.Welcome to Hyatt Residence Club Sarasota – Siesta Key Beach, where effortless ownership meets elevated coastal living. Residence 604 at 915 Seaside Drive offers a rare opportunity to own a fully furnished 3-bedroom, 3-bath luxury condominium with sweeping city and skyline views, just steps from the world-famous quartz sands of Siesta Key

Matthew Hickey EXP REALTY LLC

915 Seaside Dr Unit 604, Sarasota, FL 34242
/15
$5,070 Per Month
- 1 Bath
- 420 Sq Ft
- House for Rent
6006 Midnight Pass Rd Unit 2, Sarasota, FL 34242

Starting at $154/night! Escape to the perfect beachside retreat at our charming and cozy studio on beautiful Siesta Key. Just steps from the world-renowned white sands of Siesta Beach, this inviting space is ideal for couples or solo travelers looking to unwind in comfort. The studio features two plush queen-size beds, a relaxed seating area, and a flat-screen TV for your entertainment. Prepare

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6006 Midnight Pass Rd Unit 2, Sarasota, FL 34242
/2
$1,600,000 Sold Mar 12, 2026

5121 Sandy Shore Ave, Sarasota, FL 34242
- 3 Beds
- 3 Baths
- 2,726 Sq Ft
- Built 2000
Last Sold Summary
- $587/SF
Current Estimated Value $1,793,550

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

5121 Sandy Shore Ave, Sarasota, FL 34242

/57
Est $1,751,858 Not Listed For Sale

1660 Summerhouse Ln Unit 104, Sarasota, FL 34242
- 3 Beds
- 3.5 Baths
- 2,490 Sq Ft
- Built 2007
1660 Summerhouse Ln Unit 104, Sarasota, FL 34242

Last Sold Summary
- 9% Below List Price
- $773/SF
- 171 Days On Market
- Last Sold Price $1,925,000
- Feb 09, 2024
Last Listing Agent Cole Collins COLDWELL BANKER REALTY

/60
$3,850,000
- 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
/10
$8,370 Per Month
- 2 Beds
- 1 Bath
- 836 Sq Ft
- House for Rent
6154 Midnight Pass Rd Unit C08, 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 C08, Sarasota, FL 34242
/2
$370,000 Sold Apr 22, 2026

1257 S Portofino Dr Unit 203, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Built 1968
Last Sold Summary
- $398/SF
- 3 Days On Market
Current Estimated Value $453,933

Last Listing Agent Melissa Gissinger MICHAEL SAUNDERS & COMPANY

1257 S Portofino Dr Unit 203, Sarasota, FL 34242

/43
Est $669,432 Not Listed For Sale

1080 W Peppertree Ln Unit 303A, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,365 Sq Ft
- Built 1974
1080 W Peppertree Ln Unit 303A, Sarasota, FL 34242

Last Sold Summary
- 13% Below List Price
- $564/SF
- 124 Days On Market
- Last Sold Price $770,000
- Dec 22, 2023
Last Listing Agent Cheryl Santelli PEPPERTREE BAY REALTY INC

/61
$2,590,000 Pending
- 4 Beds
- 3.5 Baths
- 3,228 Sq Ft
467 Canal Rd Unit 467, Sarasota, FL 34242

Under contract-accepting backup offers. 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

Dan Miller PREFERRED SHORE LLC

467 Canal Rd Unit 467, Sarasota, FL 34242
/13
$8,370 Per Month
- 2 Beds
- 1 Bath
- 672 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 3, Sarasota, FL 34242

Enjoy a relaxing getaway in Villa 3 at Aloha Kai, a cozy beach villa beautifully decorated with casual coastal charm. The screened porch provides the perfect spot for morning coffee, unwinding with a good book, or entertaining guests in the evening with a meal or cocktail. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 3, Sarasota, FL 34242
/2
$2,535,000 Sold Feb 13, 2026

4757 Higel Ave, Sarasota, FL 34242
- 4 Beds
- 3.5 Baths
- 3,232 Sq Ft
- Built 1990
Last Sold Summary
- 8% Below List Price
- $784/SF
- 44 Days On Market
Current Estimated Value $2,535,695

Last Listing Agent Victoria Turner MICHAEL SAUNDERS & COMPANY

4757 Higel Ave, Sarasota, FL 34242

/41
Est $1,248,063 Not Listed For Sale

6150 Midnight Pass Rd Unit 40, Sarasota, FL 34242
- 4 Beds
- 3 Baths
- 1,976 Sq Ft
- Built 1967
6150 Midnight Pass Rd Unit 40, Sarasota, FL 34242

Last Sold Summary
- 11% Below List Price
- $709/SF
- 89 Days On Market
- Last Sold Price $1,400,000
- Feb 16, 2024
Last Listing Agent Tina Johns COLDWELL BANKER REALTY

/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
/18
$8,970 Per Month
- 1 Bath
- 435 Sq Ft
- House for Rent
6006 Midnight Pass Rd Unit 68, Sarasota, FL 34242

Starting at $299/night! Explore a luxurious studio-style condominium at Casa Mar, featuring one bathroom and a queen-sized murphy bed. This elegant retreat boasts a fully equipped kitchen that flows into a spacious dining area, ideal for hosting guests. Benefit from the convenience of a private carport just a few steps away from your residence. Casa Mar offers an impressive range of amenities,

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6006 Midnight Pass Rd Unit 68, Sarasota, FL 34242
/2
$2,900,000 Sold Jul 31, 2025

875 Siesta Key Cir, Sarasota, FL 34242
- 3 Beds
- 3.5 Baths
- 5,423 Sq Ft
- Built 1990
Last Sold Summary
- 23% Below List Price
- $535/SF
- 117 Days On Market
Current Estimated Value $2,997,958

Last Listing Agent Thomas Cail RE/MAX ALLIANCE GROUP

875 Siesta Key Cir, Sarasota, FL 34242

/33
Est $782,990 Not Listed For Sale

6150 Midnight Pass Rd Unit 35, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,220 Sq Ft
- Built 1967
6150 Midnight Pass Rd Unit 35, Sarasota, FL 34242

Last Sold Summary
- 9% Below List Price
- $709/SF
- 17 Days On Market
- Last Sold Price $865,000
- Feb 15, 2024
Last Listing Agent Domanic Calamese KW COASTAL LIVING III

/50
$675,000
- 2 Beds
- 2 Baths
- 921 Sq Ft
5830 Midnight Pass Rd Unit 86, Sarasota, FL 34242

This stunning 2-bedroom, 2-bath retreat is steps from Siesta Key’s renowned powdery white sand. Fully renovated with premium, top-to-bottom upgrades (new plumbing, electrical, HVAC, and high-end appliances), this turnkey property is rental-ready. This unit has been completely redone with quality everything and no expenses spared! Enjoy immediate income and income potential with easy access to

Cindy Furtado WATERSIDE REALTY LLC

5830 Midnight Pass Rd Unit 86, Sarasota, FL 34242
/13
$8,700 Per Month
- 1 Bed
- 1 Bath
- 672 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 35, Sarasota, FL 34242

Toes in the sand and sunshine on your shoulder—welcome home to the spacious one-bedroom Villa 35 at Aloha Kai. This beautifully updated villa features granite countertops in both the kitchen and bath, while the bedroom offers ample space and a large closet. The open-concept layout extends to a front porch enclosed with windows and blinds, providing additional living space and privacy. Located on

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 35, Sarasota, FL 34242
/2
$930,000 Sold May 16, 2025

5780 Midnight Pass Rd Unit 205, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,473 Sq Ft
- Built 1979
Last Sold Summary
- 7% Below List Price
- $631/SF
- 114 Days On Market
Current Estimated Value $939,702

Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

5780 Midnight Pass Rd Unit 205, Sarasota, FL 34242

/59
Est $659,378 Not Listed For Sale

6150 Midnight Pass Rd Unit 18, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,101 Sq Ft
- Built 1967
6150 Midnight Pass Rd Unit 18, Sarasota, FL 34242

Last Sold Summary
- 15% Below List Price
- $708/SF
- 73 Days On Market
- Last Sold Price $780,000
- Oct 10, 2023
Last Listing Agent Domanic Calamese KW COASTAL LIVING III

/56
$799,999
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
6005 Midnight Pass Rd Unit N4, Sarasota, FL 34242

Perfect Snowbird Getaway! Mid Siesta Key, highly sought after, free-standing villa with it’s own private courtyard front, side and rear. Maintenance Free condo lifestyle that feels like a single family home. Situated in Provincial Gardens on a lushly landscaped and tree canopied street of only 26 units offering old Florida charm. This updated, Turnkey Furnished 2 bedroom + Den, 2 bath offers

Linda Starcher, PA RE/MAX ALLIANCE GROUP

6005 Midnight Pass Rd Unit N4, Sarasota, FL 34242
/20
$5,070 Per Month
- 1 Bath
- 435 Sq Ft
- House for Rent
6006 Midnight Pass Rd Unit 10, Sarasota, FL 34242

Starting at $169/night. Discover the perfect beach getaway at our charming studio, ideally located on the beautiful Siesta Key. Just steps from the pristine white sands of Siesta Beach, this cozy, well-appointed retreat is perfect for couples or solo travelers seeking a relaxing escape. The studio features a comfortable queen-size bed, a cozy seating area, and a flat-screen TV for your

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6006 Midnight Pass Rd Unit 10, Sarasota, FL 34242
/2
$650,000 Sold Aug 22, 2025

670 Venice Ln, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 2,114 Sq Ft
- Built 1971
Last Sold Summary
- 34% Below List Price
- $307/SF
- 118 Days On Market
Current Estimated Value $759,972

Last Listing Agent Debbie Lane RE/MAX ALLIANCE GROUP

670 Venice Ln, Sarasota, FL 34242

/39
Est $694,792 Not Listed For Sale

6150 Midnight Pass Rd Unit 17, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 939 Sq Ft
- Built 1967
6150 Midnight Pass Rd Unit 17, Sarasota, FL 34242

Last Sold Summary
- 16% Below List Price
- $884/SF
- 6 Days On Market
- Last Sold Price $830,000
- Oct 20, 2023
Last Listing Agent Toni Zarghami KW COASTAL LIVING III

Showing Results 361 - 400, Page 10 of 18

Florida Sarasota County Siesta Key

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Siesta Key, FL Homes

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