Siesta Key, FL Homes

/41
$719,000
- 2 Beds
- 2 Baths
- 1,204 Sq Ft
1001 Beach Rd Unit A203, Sarasota, FL 34242

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 270 degrees of wraparound views thanks to 46 feet of sliding glass doors in the living and dining areas. This unit

Mike Winger TIDELINE REAL ESTATE BROKERS

1001 Beach Rd Unit A203, Sarasota, FL 34242
/91
$14,000 per month
- 4 Beds
- 3 Baths
- 2,341 Sq Ft
- House for Rent
412 Treasure Boat Way, Sarasota, FL 34242

Discover your dream home with this exquisite single family residence available for annual rental. This remarkable property redefines elegance and comfort, featuring stunning one-of-a-kind architecture that combines exceptional design with spacious living. Crafted for discerning tenants who appreciate the finer things in life, the home boasts four generously sized bedrooms and three luxurious

Beth Dilley ASCENDIA REAL ESTATE

412 Treasure Boat Way, Sarasota, FL 34242
/2
$900,000 Sold Sep 24, 2025
- 2,039 Sq Ft
- $441/SF
- 77 Days On Market
- 3 Beds
- 2 Baths
- Built 1963
5572 Shadow Lawn Dr, Sarasota, FL 34242

OWNER IS MOTIVATED! PLEASE BRING A REASONABLE OFFER. WATERFRONT HOME HALF A MILE TO SIESTA BEACH. Welcome to 5572 Shadow Lawn Drive on Siesta Key. This 3 Bedroom, 2 Bath home sits on a 14,300 SQ. FT. LOT, has a private dock and features 102 FEET OF FRONTAGE ON THE GRAND CANAL. Only one fixed bridge at Midnight Pass Rd means GREAT BOATING ACCESS to Sarasota Bay and the Gulf. Or take a short bike

Chris Kernan RE/MAX ALLIANCE GROUP

5572 Shadow Lawn Dr, Sarasota, FL 34242

/73
Est $628,098 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

/71
$1,325,000
- 4 Beds
- 3.5 Baths
- 2,659 Sq Ft
5354 Calle Florida, Sarasota, FL 34242

Tucked away on Palm Island, one of Siesta Key’s most exclusive neighborhoods, this stunning Spanish-inspired home is more than a place to live, it’s a way of life. Just a short stroll from the sugar-white sands of Siesta Key Beach and the boutiques and cafes of the Village, every day feels like a vacation.Step inside and you’re instantly transported. Arched windows frame the open

Angelica Ridley KELLER WILLIAMS ON THE WATER S

5354 Calle Florida, Sarasota, FL 34242
/24
$7,500 per month
- 1 Bed
- 1 Bath
- 708 Sq Ft
- Condo for Rent
6006 Midnight Pass Rd Unit 21, Sarasota, FL 34242

Discover your beachside retreat on world-famous Siesta Key! This beautifully updated 1-bedroom, 1-bath ground-floor condo in the sought-after Casa Mar community offers the ultimate in coastal convenience—just a short stroll to private deeded beach access and the whi te sands of Siesta Beach. Step inside to a smoke-free, pet-free unit featuring wood plank flooring, modern leather furnishings, and

Robert Bevington SHOWTIME REALTY

6006 Midnight Pass Rd Unit 21, Sarasota, FL 34242
/2
$1,600,000 Sold Sep 22, 2025
- 3,146 Sq Ft
- $509/SF
- 34 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1953
311 Island Cir, Sarasota, FL 34242

Welcome to 311 Island Circle, your dream Oasis on one of Siesta Key’s most desirable streets! Nestled on an expansive 22,000 sq ft lot on Palm Island, this property comes with a shiny new 2025 Bintelli golf cart, perfect for zipping over to Siesta Beach or the Village—just a stone's throw away at less than a mile! This stunningly renovated home offers four cozy bedrooms, a dedicated office for

Tina Ellis COMPASS FLORIDA LLC

311 Island Cir, Sarasota, FL 34242

/45
Est $625,117 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

/71
$510,000
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1300 Cove II Place Unit 710, Sarasota, FL 34242

Welcome to your slice of paradise on Siesta Key! This turnkey furnished 2 bedroom, 1.5 bathroom condo offers stunning canal views surrounded by mature tropical landscaping. With weekly rentals allowed and convenient in-house property management, it’s an ideal opportunity for both personal enjoyment and investment income. On-site property management provides professional oversight and streamlined

Halie Monde KELLER WILLIAMS ON THE WATER S

1300 Cove II Place Unit 710, Sarasota, FL 34242
/14
$7,500 per month
- 4 Beds
- 3 Baths
- 2,392 Sq Ft
- House for Rent
306 Island Cir, Sarasota, FL 34242

Available now. Lovely pool home with canal water frontage located in Siesta Key's peaceful and secluded neighborhood of PalmIsland. Completely renovated with new kitchen, bathrooms, and floor coverings throughout this island retreat. Walk four blocks to the crystalsands of world famous Siesta Beach, and just a short walk to the Village. Beautiful backyard with spacious patio, heated

Timothy Bloch QUEST PROPERTIES INC

306 Island Cir, Sarasota, FL 34242
/2
$2,400,000 Sold Sep 19, 2025
- 2,762 Sq Ft
- $869/SF
- 10 Days On Market
- 4 Beds
- 3 Baths
- Built 1976
5168 Sandy Cove Ave, Sarasota, FL 34242

Beautifully Newly Upgraded Waterfront Home on Siesta Key – 4BR | 3BA | Canal Front | Solar-Powered Discover your private oasis in this beautifully updated two-story home located directly on Siesta Key Island. Nestled at the end of a quiet cul-de-sac, this 4-bedroom, 3-bath residence offers the perfect blend of luxury, comfort, and island living — all within an A+ rated school district. Waterfront

Timothy Mitten WAGNER REALTY

5168 Sandy Cove Ave, Sarasota, FL 34242

/45
Est $658,772 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
5963 Midnight Pass Rd Unit 328, Sarasota, FL 34242

5963 Midnight Pass Rd Unit 328, Sarasota, FL 34242

/32
$615,000
- 1 Bed
- 1 Bath
- 728 Sq Ft
5830 Midnight Pass Rd Unit 52, Sarasota, FL 34242

Enjoy the ultimate beach lifestyle in this completely renovated 1 bed, 1 bath condo at Jamaica Royale. The spacious open-concept design features a beautifully updated kitchen with peninsula seating, quartz countertops, matching backsplash, sleek silver light fixtures, and brand-new appliances. Luxury vinyl plank flooring and crown molding flow throughout, creating a bright and airy coastal

Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

5830 Midnight Pass Rd Unit 52, Sarasota, FL 34242
/18
$12,600 per month
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
- House for Rent
301 Avenida Madera Unit B, Sarasota, FL 34242

Current Availability: 4/6/2025 This is THE location! Just steps to the Village cafe and the Hub Bar and Grille, and a short walk to the beach. Our 2 bedroom 2 bath beautifully updated property offers a coastal theme and open floor plan. A queen size sofa bed and an auto -inflatable queen size EZ Bed, makes this home comfortable to sleep 6 occupants. Granite countertops, stainless steel

Robert Bevington SHOWTIME REALTY

301 Avenida Madera Unit B, Sarasota, FL 34242
/2
$357,000 Sold Sep 19, 2025
- 991 Sq Ft
- $360/SF
- 403 Days On Market
- 2 Beds
- 2 Baths
- Built 1969
1300 N Portofino Dr Unit 208, Sarasota, FL 34242

MOTIVATED SELLER! The ONLY 2 bed/2 bath Siesta Condo listed under $400K! Siesta Harbor is a unique condominium complex located on the famous Siesta Key, offering residents the opportunity to lease a boat dock on an annual basis along the Intercoastal Waterway. Residents enjoy deeded access to Siesta Beach through Crescent Arms, and the community boasts Gulf-to-Bay access, a beautiful pool area,

Jill Thomas BERKSHIRE HATHAWAY HOMESERVICE

1300 N Portofino Dr Unit 208, Sarasota, FL 34242

/47
Est $937,652 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242

20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242

/69
$2,840,000
- 5 Beds
- 3.5 Baths
- 3,205 Sq Ft
430 Island Cir, Sarasota, FL 34242

Welcome to 430 Island Circle, where island living feels both luxurious and refreshingly relaxed. Set on Palm Island, the “heart of Siesta Key”, just moments from the sugar-white sands of Siesta Key Beach, this home offers the perfect balance of modern comfort and coastal charm. Completely reimagined from top to bottom, this five bedroom, three and a half bathroom residence opens with sun-filled

Jesse Bauer KELLER WILLIAMS ON THE WATER S

430 Island Cir, Sarasota, FL 34242
/34
$12,600 per month
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
- House for Rent
301 Avenida Madera Unit A, Sarasota, FL 34242

Current Availability: 5/19/2024-5/25/2024, 5/30/2024-6/7/2024, 6/23/2024-7/26/2024, 8/24/2024-10/25/2024, 11/3/2024-11/7/2024, 11/17/2024-12/5/2024 If you are looking for the perfect location for your next vacation, then your search is over! This 2 bedroom, 2 bath property features a prime location within The Village of Siesta Key and is a few blocks to the beach. Beautifully updated,

Robert Bevington SHOWTIME REALTY

301 Avenida Madera Unit A, Sarasota, FL 34242
/2
$660,000 Sold Sep 17, 2025
- 1,290 Sq Ft
- $512/SF
- 187 Days On Market
- 2 Beds
- 2 Baths
- Built 1975
6415 Midnight Pass Rd Unit 909, Sarasota, FL 34242

Stunning Intracoastal and Gulf views from this rare 9th-floor corner unit on Siesta Key. Welcome to Unit #909 at The Anchorage—a beautifully updated condo offering breathtaking panoramic views of the Intracoastal Waterway and Gulf glimpses from three private balconies. This light-filled corner unit is perched on the 9th floor and designed to capture peaceful coastal living from every angle.

Crystal Saly RE/MAX PALM

6415 Midnight Pass Rd Unit 909, Sarasota, FL 34242

/27
Est $666,282 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242

6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242

/72
$575,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
4660 Ocean Blvd Unit Q1, Sarasota, FL 34242

Experience million-dollar, direct Gulf views from this ground floor condominium in the sought after community of Sea Village on Siesta Key. Enjoy sunsets every evening from your private screened-in lanai, just steps from the shoreline and minutes from one of the world’s top beaches. This 2-bedroom, 2-bath residence has been thoughtfully updated with a fully remodeled kitchen, tile flooring

Halie Monde KELLER WILLIAMS ON THE WATER S

4660 Ocean Blvd Unit Q1, Sarasota, FL 34242
/79
$7,000 per month
- 4 Beds
- 3 Baths
- 2,439 Sq Ft
- House for Rent
4852 Featherbed Ln, Sarasota, FL 34242

SIESTA KEY, Sarasota, Single Family Pool Home....Well-positioned for convenience and natural attractions . . . and dinners are breezy on your patio! The advantages of this appealing home in the Siesta area of Siesta Key become apparent while you are still walking the perimeter. The clear blue pool and the patio are a perfect pairing of amenities, supporting a variety of social activities and

Jane Hunter JENNETTE PROPERTIES INC

4852 Featherbed Ln, Sarasota, FL 34242
/2
$400,000 Sold Sep 16, 2025
- 929 Sq Ft
- $431/SF
- 63 Days On Market
- 2 Beds
- 2 Baths
- Built 1968
1257 S Portofino Dr Unit 306, Sarasota, FL 34242

Live the Florida dream in this fully furnished, designer-finished 2 bedroom, 2 bathroom condo nestled within the coveted Siesta Harbor community, offering deeded beach access to world-famous Siesta Key Beach just across the street. Situated on the third floor with picturesque water views, this beautifully updated unit features granite countertops, white shaker cabinetry, stainless steel

Toni Zarghami KW COASTAL LIVING III

1257 S Portofino Dr Unit 306, Sarasota, FL 34242

/73
Est $547,859 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1500 Cove II Place Unit 532, Sarasota, FL 34242

1500 Cove II Place Unit 532, Sarasota, FL 34242

/100
$2,659,999
- 4 Beds
- 3 Baths
- 3,541 Sq Ft
5012 Higel Ave, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Discover this FULLY RENOVATED four-bedroom, three-bathroom sanctuary spanning 3,541 square feet, where luxury living meets WATERFRONT tranquility. Situated on almost a half acre lot, with rear views facing west for colorful sunsets, this meticulously crafted residence boasts a heated pool, a floating dock and long seawall inviting water enthusiasts

Rachelle Tirey PREFERRED SHORE LLC

5012 Higel Ave, Sarasota, FL 34242
/51
$8,900 per month
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
- Condo for Rent
1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242

Experience coastal living at its finest in this 3-bedroom, 2-bathroom second-floor lakefront condo located in the desirable Gulf and Bay Club Bayside community in Siesta Key. With breathtaking views of the lake, pool, and tennis court from the screened-in lanai, this home is a perfect retreat. The kitchen is equipped with stainless-steel appliances, and the adjacent dining table offers a great

Andy Moore GULF COAST REALTY & MANAGEMENT

1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
/2
$815,000 Sold Sep 15, 2025
- 2,522 Sq Ft
- $323/SF
- 173 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1980
710 Birdsong Ln, Sarasota, FL 34242

Island living at it's best. Just a short distance to world famous Siesta Key Beach. This home has had NO flood damage inside the home or garage areas. Custom built by Schrock home builders. Featuring 3 bedrooms, den/office & 2 1/2 baths. Over 2500 sq. ft. under air with an over sized 2 car garage with screen. New roof just installed. Kitchen was remodeled with new cabinets, granite counters,

Cynthia Bowers COLDWELL BANKER SARASOTA CENT.

710 Birdsong Ln, Sarasota, FL 34242

/79
Est $661,456 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,139 Sq Ft
1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242

1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242

/76
$18,500,000
- 4 Beds
- 6 Baths
- 8,138 Sq Ft
3799 Flamingo Ave, Sarasota, FL 34242

Relax and take in the positive energy of Lotus-style living in this one-of-a-kind Balinese-inspired resort compound on north end of the world-famous Siesta Key. Nothing is needed to begin your Zen journey as the property comes completely furnished down to dishes, silverware and a Buddha living wall. The coexistence of indoor and outdoor space blends over 8,000 square feet of indoor space with

Joel Schemmel DOUGLAS ELLIMAN

3799 Flamingo Ave, Sarasota, FL 34242
/36
$2,000 per month
- 1 Bed
- 2 Baths
- 780 Sq Ft
- Condo for Rent
1300 N Portofino Dr Unit 205, Sarasota, FL 34242

Available Nov through Dec 2025 for $2,000 per month. 55+ community. Available Jan-Mar 2026 for $6,000 per month. Welcome to your dream coastal escape in beautiful Siesta Harbor on Siesta Key! This turnkey furnished; spacious one-bedroom, two-bath condo is available now through October 2025. Perfectly situated along a peaceful canal, it offers stunning water views and a truly relaxing atmosphere.

Jonathan OSteen O'STEEN GROUP INC

1300 N Portofino Dr Unit 205, Sarasota, FL 34242
/2
$600,000 Sold Sep 15, 2025
- Land
- 0.14 Acre
- $4,285,714 per Acre
- 183 Days On Market
4183 Roberts Point Cir Unit Lot 18, Sarasota, FL 34242

Development opportunity! Lot 18 is in the center of the three adjacent parcels that are for sale in Siesta Key’s private enclave of Roberts Point. The original structure has been demolished. As one of the most affordably priced buildable lots on Siesta Key, this is your chance to make your dream island life a reality. Known for its laid-back island ambience, you will find updated cottages

Rudy Dudon MICHAEL SAUNDERS & COMPANY

4183 Roberts Point Cir Unit Lot 18, Sarasota, FL 34242

/79
Est $777,210 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,720 Sq Ft
1600 Cove II Place Unit 424, Sarasota, FL 34242

1600 Cove II Place Unit 424, Sarasota, FL 34242

/57
$1,350,000
- 1 Bed
- 1.5 Baths
- 928 Sq Ft
5400 Ocean Blvd Unit 5-3, Sarasota, FL 34242

Experience the Ultimate in Siesta Key Beachfront LivingLocated directly on world-renowned Siesta Beach, rated #1 in the U.S. and #4 worldwide by TripAdvisor, this stunning fifth-floor corner residence captures the essence of luxury coastal living. Recently renovated to perfection, this 1-bedroom, 1.5-bath condominium offers a rare combination of modern sophistication, coastal elegance, and

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

5400 Ocean Blvd Unit 5-3, Sarasota, FL 34242
/40
$8,500 per month
- 3 Beds
- 4 Baths
- 2,168 Sq Ft
- House for Rent
1256 Riegels Landing Dr, Sarasota, FL 34242

This newly renovated (March, 2025) 3 bed, 4 full bath home with a deep water dock just down the street is located within walking distance of the famous Siesta Key Beach. The one of a kind house was design by the Sarasota School of Architecture. The master and main guest bedroom are located on the main level along with the kitchen, living, laundry and dining rooms. An additional bedroom and full

Christopher Davenport STARLINK REALTY INC

1256 Riegels Landing Dr, Sarasota, FL 34242
/2
$600,000 Sold Sep 15, 2025
- Land
- 0.14 Acre
- $4,285,714 per Acre
- 183 Days On Market
4185 Roberts Point Cir Unit Lot 19, Sarasota, FL 34242

Development opportunity! Lot 19 is the eastern most lot of the three adjacent parcels that are for sale in Siesta Key’s private enclave of Roberts Point. The original structure has been demolished. As one of the most affordably priced buildable lots on Siesta Key, this is your chance to make your dream island life a reality. Known for its laid-back island ambience, you will find updated cottages

Rudy Dudon MICHAEL SAUNDERS & COMPANY

4185 Roberts Point Cir Unit Lot 19, Sarasota, FL 34242

/17
Est $495,627 Not Listed For Sale
- 1 Bed
- 1 Bath
- 612 Sq Ft
6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242

6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242

/53
$1,749,000
- 2 Beds
- 2 Baths
- 1,204 Sq Ft
6144 Midnight Pass Rd Unit 2N, Sarasota, FL 34242

It's all about THE VIEW and the Direct Beach Access!!! This first floor condominium has a Full Gulf View from the living room and glassed-in lanai. The water views are amazing, and the sunsets are gorgeous! You will walk out your front door right down to the sand to enjoy the warm Gulf water in minutes. There was no water intrusion and no water damage to this unit in past storms, as there are

Susan Keal MICHAEL SAUNDERS & COMPANY

6144 Midnight Pass Rd Unit 2N, Sarasota, FL 34242
/36
$7,500 per month
- 1 Bed
- 1 Bath
- 600 Sq Ft
- Condo for Rent
6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242

No roads to cross to get to the beach! Just listed- This clean, updated, cheery one bedroom/one bath condo in Casa Mar is ready for your beach stay! Covered parking, on-site community laundry rooms, and heated pool are just some of the amenities this Association has to offer. A recently added security gate adds value. This condo is ready for your stay- includes linens & beach towels. Pack your

Robert Bevington SHOWTIME REALTY

6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242
/2
$1,640,000 Sold Sep 12, 2025
- 3,893 Sq Ft
- $421/SF
- 31 Days On Market
- 4 Beds
- 7 Baths
- Built 1964
4831 Primrose Path, Sarasota, FL 34242

Luxury Canal-Front Oasis in Siesta Key | 4831 Primrose PathUpdated Three-Story Waterfront Retreat with Designer Touches & Flexible Living SpacesDiscover the perfect blend of luxury, comfort, and location at 4831 Primrose Path, a beautifully updated three-story canal-front residence situated on a lush corner lot in one of Siesta Key’s most sought-after neighborhoods. This elegant

Derek Edwards KELLER WILLIAMS ON THE WATER S

4831 Primrose Path, Sarasota, FL 34242

/69
Est $563,506 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,182 Sq Ft
5600 Beach Way Dr Unit 209, Sarasota, FL 34242

5600 Beach Way Dr Unit 209, Sarasota, FL 34242

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