Siesta Key, FL Homes

/52
$35,000
- 4 Beds
- 4 Baths
- 2,625 Sq Ft
915 Seaside Dr Unit 511, Weeks 2-3, Sarasota, FL 34242

Fractional Ownership. Experience the ultimate in coastal luxury with this Guaranteed Gulf View Deluxe Winter Fractional Package—featuring one-sixteenth ownership of an extraordinary Siesta Key Beach residence. Your dream of owning a new, high-end home on America’s #1 beach can now be a reality, offering an effortless way to enjoy the best of beachfront living without compromise. Step into an

Kelly Mooney

DOUGLAS ELLIMAN

(941) 207-0824

915 Seaside Dr Unit 511, Weeks 2-3, Sarasota, FL 34242
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/49
$2,000 per month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Apartment for Rent
6327 Midnight Pass Rd Unit 999, Sarasota, FL 34242

**DON’T MISS THIS OPPORTUNITY TO LIVE ON WORLD-FAMOUS SIESTA KEY!**ALL UTILITIES & WIFI INCLUDED**Welcome to Midnight Cove II—an impeccably maintained community on Siesta Key, just moments from the powdery white sands of Crescent Beach and minutes from iconic Siesta Beach. A quick ride brings you to Siesta Key Village, where you can enjoy boutique shopping, great dining, cocktails, live music,

Cody Smith RENT SARASOTA

6327 Midnight Pass Rd Unit 999, Sarasota, FL 34242
/2
$1,450,000 Sold Nov 04, 2025

4108 Roberts Point Rd, Sarasota, FL 34242
- 3 Beds
- 2.5 Baths
- 2,511 Sq Ft
- Built 2001
Last Sold Summary
- 23% Below List Price
- $577/SF
- 142 Days On Market
Last Listing Agent Melissa Gissinger MICHAEL SAUNDERS & COMPANY

4108 Roberts Point Rd, Sarasota, FL 34242

/2
Est $581,707 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
5963 Midnight Pass Rd Unit 344, Sarasota, FL 34242

5963 Midnight Pass Rd Unit 344, Sarasota, FL 34242

/52
$1,075,000
- 3 Beds
- 2 Baths
- 1,715 Sq Ft
5112 Oakmont Place, Sarasota, FL 34242

Beneath the whispering palms of Siesta Key, 5112 Oakmont Place feels like the kind of home you discover once in a lifetime, a private retreat where island elegance meets easy coastal living. As you turn onto this quiet, tree-lined street, the pace slows. The scent of salt air drifts in through the open windows, and you can almost hear the gentle roll of waves in the distance. Enter inside to find

Roberta Tengerdy, PA

PREMIER SOTHEBY'S INTERNATIONAL REALTY

(941) 541-1293

5112 Oakmont Place, Sarasota, FL 34242
/16
$7,000 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Condo for Rent
4660 Ocean Blvd Unit P1, Sarasota, FL 34242

***SEASON OR LONG TERM RENTAL*** Turnkey furnished waterfront condo in the desirable Sea Village community. Enjoy stunning views of Big Pass and the Gulf, plus easy access to the community pool. The home features travertine flooring, crown molding, hurricane-rated sliders, plantation shutters, and an open living/dining layout. The kitchen includes wood cabinetry, granite countertops, a breakfast

Nelson Reyes SHOWTIME REALTY

4660 Ocean Blvd Unit P1, Sarasota, FL 34242
/2
$520,000 Sold Mar 26, 2025

1048 W Peppertree Ln Unit 118B, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 975 Sq Ft
- Built 1974
Last Sold Summary
- 19% Below List Price
- $533/SF
- 36 Days On Market
Current Estimated Value $514,950

Last Listing Agent Marc Rasmussen CORCORAN DWELLINGS REALTY

1048 W Peppertree Ln Unit 118B, Sarasota, FL 34242

/72
Est $656,883 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
101 Whispering Sands Dr Unit 206, Sarasota, FL 34242

101 Whispering Sands Dr Unit 206, Sarasota, FL 34242

/60
$2,250,000
- 4 Beds
- 3.5 Baths
- 2,971 Sq Ft
116 Garden Ln, Sarasota, FL 34242

Effortless Island Living on Siesta Key’s Coveted North End.Discover the perfect blend of modern luxury and low-maintenance living in thiscontemporary coastal retreat, ideally located on the quiet North End of Siesta Key.Enjoy deeded beach access, mesmerizing Gulf and Big Pass views, and effortlessproximity to Siesta Village, the North Bridge, and downtown Sarasota.Built in

Gerard Healy

WILLIAM RAVEIS REAL ESTATE

(941) 337-4899

116 Garden Ln, Sarasota, FL 34242
/63
$5,700 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
1250 N Portofino Dr Unit 303, Sarasota, FL 34242

Available for season 2026! Welcome to Coastal Living at its finest, perfectly nestled on the sought after barrier island of Siesta Key. Updated unit offers serene water views, abundant natural light and the relaxed elegance that defines Florida living. Located in a meticulously maintained waterfront community, this spacious unit features an open and inviting layout ideal for seasonal

Angela Bailey MONARCH PROPERTY GROUP LLC

1250 N Portofino Dr Unit 303, Sarasota, FL 34242
/2
$1,100,000 Sold Jun 16, 2025

5239 Siesta Cove Dr, Sarasota, FL 34242
- 4 Beds
- 4 Baths
- 2,333 Sq Ft
- Built 1983
Last Sold Summary
- 20% Below List Price
- $471/SF
- 86 Days On Market
Current Estimated Value $1,109,110

Last Listing Agent Christopher Grant GRANT TEAM REAL ESTATE, LLC

5239 Siesta Cove Dr, Sarasota, FL 34242

/36
Est $869,867 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,720 Sq Ft
1600 Cove II Place Unit 420, Sarasota, FL 34242

1600 Cove II Place Unit 420, Sarasota, FL 34242

/59
$125,000
- 3 Beds
- 3 Baths
- 1,780 Sq Ft
915 Seaside Dr Unit 606, Weeks 14-17, Sarasota, FL 34242

Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Ownership Package, offering 2 one sixteenth ownership packages of an exceptional Siesta Key Beach residence. This is a rare opportunity to own four consecutive winter weeks (Weeks 14–17)—providing extended beachfront living during the most desirable season on America’s #1 beach. For buyers

Kelly Mooney

DOUGLAS ELLIMAN

(941) 256-2943

915 Seaside Dr Unit 606, Weeks 14-17, Sarasota, FL 34242
/57
$3,500 per month
- 2 Beds
- 1.5 Baths
- 1,122 Sq Ft
- Townhouse for Rent
11 Sandy Cove Rd Unit 8F, Sarasota, FL 34242

Sandy Cove – 2-Bedroom Vacation Rental! Available Nov 1 and beyond! Private Beach!The owner is offering unbelievable seasonal rates!Located in the sought-after Sandy Cove Community, just steps from Siesta Village with its own private beach and breathtaking Gulf sunsets. Fully turnkey furnished and ready to enjoy!

Cole Collins COLDWELL BANKER REALTY

11 Sandy Cove Rd Unit 8F, Sarasota, FL 34242
/2
$735,000 Sold Nov 27, 2025

1055 Beach Rd Unit B204, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,204 Sq Ft
- Built 1981
Last Sold Summary
- 5% Below List Price
- $610/SF
- 29 Days On Market
Last Listing Agent Jason Wood CORCORAN DWELLINGS REALTY

1055 Beach Rd Unit B204, Sarasota, FL 34242

/62
Est $576,811 Not Listed For Sale
- 1 Bed
- 1.5 Baths
- 872 Sq Ft
5962 Midnight Pass Rd Unit 132, Sarasota, FL 34242

5962 Midnight Pass Rd Unit 132, Sarasota, FL 34242

/99
$775,000
- Land
- 0.26 Acre
- $2,980,769 per Acre
5019 Commonwealth Dr, Sarasota, FL 34242

100,000 price reduction! A Rare Build Opportunity on Siesta Key! Located on one of Siesta Key’s most beloved streets, this .26-acre lot on Commonwealth Drive presents a unique opportunity to build new in an established, multi-million-dollar neighborhood. Surrounded by lush, mature landscaping and a peaceful, community-focused setting, the lot offers the ideal backdrop for your vision—whether

Dawn Bear

WILLIAM RAVEIS REAL ESTATE

(941) 394-0942

5019 Commonwealth Dr, Sarasota, FL 34242
/45
$4,500 per month
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
- Condo for Rent
5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242

AVAILABLE Jan, Feb, Mar, April 2026! Experience the best of Siesta Key living in this beautifully updated 2-bedroom, 2-bathroom condo at the sought-after Harbor Towers Yacht & Racquet Club. Fully furnished and thoughtfully renovated, this 1,056 sq ft residence offers a perfect blend of comfort and luxury. The primary suite has a king-sized bed and en-suite bath, while the guest bedroom provides

Anna Williams SHOWTIME REALTY

5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242
/2
$5,400,000 Sold Mar 12, 2025

147 Avenida Veneccia, Sarasota, FL 34242
- 7 Beds
- 7 Baths
- 3,510 Sq Ft
- Built 2023
Last Sold Summary
- $1,538/SF
- 0 Days On Market
Current Estimated Value $5,049,856

Last Listing Agent Curtis Ware KW COASTAL LIVING III

147 Avenida Veneccia, Sarasota, FL 34242

/35
Est $1,993,737 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,774 Sq Ft
6900 Bochi Cir, Sarasota, FL 34242

6900 Bochi Cir, Sarasota, FL 34242

/46
$18,000
- 4 Beds
- 3 Baths
- 2,460 Sq Ft
915 Seaside Dr Unit 613, Weeks 32-33, Sarasota, FL 34242

Fractional Ownership. Summer Fractional Package, with 1/16th shares of ownership! Your dream of a new luxury home on Siesta Key Beach can now be a reality; an enviable lifestyle on America's top-rated beach! Here is your opportunity to own a piece of paradise without giving up all the amenities and services. An enviable lifestyle on America's top-rated beach! Your dream of a new luxury home on

Kelly Mooney

DOUGLAS ELLIMAN

(941) 269-1352

915 Seaside Dr Unit 613, Weeks 32-33, Sarasota, FL 34242
/20
$6,500 per month
- 2 Beds
- 2 Baths
- 1,264 Sq Ft
- House for Rent
143 Whispering Sands Dr, Sarasota, FL 34242

Available for season March and April 2026! This 2 bedroom 2 bath villa with easy ground floor entry features tile flooring in the main living areas and plush new carpeting in the bedrooms. The stylish galley kitchen has been fully updated with custom white cabinetry, granite countertops and backsplash, recessed lighting, and brand-new GE appliances, perfect for preparing meals after a day at the

Maureen Plichta STRINGER MANAGEMENT INC

143 Whispering Sands Dr, Sarasota, FL 34242
/2
$692,000 Sold Oct 06, 2025

6285 Midnight Pass Rd Unit 201, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,387 Sq Ft
- Built 1981
Last Sold Summary
- 13% Below List Price
- $499/SF
- 165 Days On Market
Last Listing Agent Marci McFarland MICHAEL SAUNDERS & COMPANY

6285 Midnight Pass Rd Unit 201, Sarasota, FL 34242

/47
Est $840,469 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,307 Sq Ft
1321 Dockside Place, Sarasota, FL 34242

1321 Dockside Place, Sarasota, FL 34242

/48
$960,000
- 3 Beds
- 2 Baths
- 1,730 Sq Ft
711 Birdsong Ln, Sarasota, FL 34242

Located in the heart of Siesta Key, this three-bedroom, two-bath home with a two-car garage offers a rare opportunity to experience island living just one mile from Siesta Key Beach—consistently ranked the #1 beach in the United States for its white quartz sand, turquoise waters, and year-round appeal.This property is perched on an elevated lot that has never experienced flooding. Recent

Julianna Burns

BERKSHIRE HATHAWAY HOMESERVICE

(941) 390-4919

711 Birdsong Ln, Sarasota, FL 34242
/36
$7,500 per month
- 1 Bed
- 1 Bath
- 728 Sq Ft
- Condo for Rent
5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242

Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door.Inside, the condo is

Robert Bevington SHOWTIME REALTY

5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
/2
$645,000 Sold Jun 17, 2025

6415 Midnight Pass Rd Unit 710, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,290 Sq Ft
- Built 1975
Last Sold Summary
- 1% Below List Price
- $500/SF
- 3 Days On Market
Current Estimated Value $630,025

Last Listing Agent Karen Whitaker PREMIER SOTHEBY'S INTERNATIONAL REALTY

6415 Midnight Pass Rd Unit 710, Sarasota, FL 34242

/2
Est $6,680,163 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 7,506 Sq Ft
1250 Hidden Harbor Way, Sarasota, FL 34242

1250 Hidden Harbor Way, Sarasota, FL 34242

/45
$57,000
- 3 Beds
- 2 Baths
- 1,750 Sq Ft
915 Seaside Dr Unit 312, Weeks 16-17, Sarasota, FL 34242

Fractional Ownership. Winter Fractional Package, with 1/16th shares of ownership! Your dream of a new luxury home on Siesta Key Beach can now be a reality; an enviable lifestyle on America's top-rated beach! Here is your opportunity to own a piece of paradise without giving up all the amenities and services. An enviable lifestyle on America's top-rated beach! Your dream of a new luxury home on

Kelly Mooney

DOUGLAS ELLIMAN

(941) 352-1199

915 Seaside Dr Unit 312, Weeks 16-17, Sarasota, FL 34242
/70
$7,500 per month
- 2 Beds
- 2 Baths
- 896 Sq Ft
- Condo for Rent
1137 N Moonmist Ct Unit L7, Sarasota, FL 34242

This is a short term rental. Listing reflects peak season rate. Available peak season months: January 2026, February 2026, April 2026. Welcome to The Blue Luna, a serene stand-alone villa nestled in the tropical paradise of Polynesian Gardens on Siesta Key. This two-bedroom, two-bathroom home has been thoughtfully decorated with a calming, coastal blue palette that reflects the soft light of the

Beth Dilley ASCENDIA REAL ESTATE

1137 N Moonmist Ct Unit L7, Sarasota, FL 34242
/2
$3,270,000 Sold Apr 01, 2025

77 Sandy Hook Rd N, Sarasota, FL 34242
- 2 Beds
- 2.5 Baths
- 2,627 Sq Ft
- Built 1966
Last Sold Summary
- 14% Below List Price
- $1,245/SF
- 75 Days On Market
Current Estimated Value $3,069,170

Last Listing Agent Daniel Shattuck FLORIDA REALTY INVESTMENTS

77 Sandy Hook Rd N, Sarasota, FL 34242

/72
Est $1,334,435 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,876 Sq Ft
22 Sandy Cove Rd Unit 502, Sarasota, FL 34242

22 Sandy Cove Rd Unit 502, Sarasota, FL 34242

/24
$375,000
- 1 Bed
- 1 Bath
- 797 Sq Ft
5641 Midnight Pass Rd Unit 904, Sarasota, FL 34242

Rarely available and beautifully updated, this second-floor 1-bedroom, 1-bathroom residence in White Sands Village is the perfect coastal retreat or investment opportunity. Ideally located just across the street from world-famous Siesta Key Beach, this condo also enjoys a coveted view of the lush courtyard, a serene setting to relax and unwind. This turnkey furnished unit is move-in ready and

Jim Gammello

WILLIAM RAVEIS REAL ESTATE

(941) 207-9258

5641 Midnight Pass Rd Unit 904, Sarasota, FL 34242
/77
$6,000 per month
- 3 Beds
- 2.5 Baths
- 2,012 Sq Ft
- Townhouse for Rent
357 Tierra Mar Ln Unit 5, Sarasota, FL 34242

Siesta Key Furnished Annual or Seasonal Rental (4 month minimum). You will love living in this quiet enclave of 6 homes, tucked away from all of the hustle and bustle but walkable to all of the many dining, shopping and entertainment venues the vibrant Siesta Key Village offers! This amazing Townhome lives like a private residence and offers 3 bedrooms, and 2 and one half baths. This gorgeous

Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

357 Tierra Mar Ln Unit 5, Sarasota, FL 34242
/2
$1,400,000 Sold Dec 18, 2025

4865 Featherbed Ln, Sarasota, FL 34242
- 4 Beds
- 4 Baths
- 4,482 Sq Ft
- Built 1955
Last Sold Summary
- 26% Below List Price
- $312/SF
- 348 Days On Market
Last Listing Agent Janet Boyden PREMIER SOTHEBY'S INTERNATIONAL REALTY

4865 Featherbed Ln, Sarasota, FL 34242

/46
Est $1,254,803 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,898 Sq Ft
22 Sandy Cove Rd Unit 501, Sarasota, FL 34242

22 Sandy Cove Rd Unit 501, Sarasota, FL 34242

/81
$2,149,000
- 4 Beds
- 3 Baths
- 2,657 Sq Ft
4817 Ocean Blvd, Sarasota, FL 34242

Welcome to 4817 Ocean Blvd – Your Private Lakefront Escape in the Heart ofSiesta KeySet on a tranquil spring-fed lake just moments from Siesta Beach and the Village, thisflood resilient and meticulously maintained coastal residence offers year-roundenjoyment or the perfect lock-and-leave retreat. Elevated and thoughtfully updated, itblends timeless coastal style with

Gerard Healy

WILLIAM RAVEIS REAL ESTATE

(941) 207-6570

4817 Ocean Blvd, Sarasota, FL 34242
/57
$7,900 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Property for Rent
4660 Ocean Blvd Unit N1, Sarasota, FL 34242

Escape to Paradise on Siesta Key! Your dream seasonal getaway awaits at 4660 Ocean Blvd Unit N1, Sarasota, FL 34242. Immerse yourself in the tranquil beauty of the Gulf Coast, where pristine sands meet crystal-clear waters.This exquisite 2-bedroom, 2-bathroom condo is your ticket to an unforgettable retreat. Step into your sun-drenched sanctuary, tastefully furnished to embody comfort and

Robert Bevington SHOWTIME REALTY

4660 Ocean Blvd Unit N1, Sarasota, FL 34242
/2
$670,000 Sold May 28, 2025

1113 Lake House Cir Unit C110, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,352 Sq Ft
- Built 1981
Last Sold Summary
- 3% Below List Price
- $496/SF
- 23 Days On Market
Current Estimated Value $653,323

Last Listing Agent Jennifer Putnam COLDWELL BANKER SARASOTA CENT.

1113 Lake House Cir Unit C110, Sarasota, FL 34242

/2
Est $2,012,985 Not Listed For Sale
- 5 Beds
- 5 Baths
- 2,689 Sq Ft
5408 Plaza Des Las Palmas, Sarasota, FL 34242

5408 Plaza Des Las Palmas, Sarasota, FL 34242

Showing Results 41 - 80, Page 2 of 18

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