Sarasota, FL Homes

/41
$375,000
- 1 Bed
- 1 Bath
- 656 Sq Ft
105 Pass Key Rd Unit 105, Sarasota, FL 34242

ATTENTION: ALL BEACH LOVERS!! Want to own a piece of paradise? Here is your chance!! This FIRST FLOOR 1+ bdrm is located in a private gulf front community. (That is PET FRIENDLY too!) This secluded enclave offers oceanfront panoramic views and just two blocks to Siesta Key VILLAGE! NO hurricane damage and NO upcoming assessments! New AC, hot water tank and hurricane sliders! Your condo boasts

Laura Rodriguez COLDWELL BANKER REALTY

105 Pass Key Rd Unit 105, Sarasota, FL 34242
/21
$5,895 per month
- 3 Beds
- 2 Baths
- 2,098 Sq Ft
- House for Rent
935 Contento St, Sarasota, FL 34242

NEW PRICE! Rare waterfront Siesta Key pool home available for annual rental! This beautifully-renovated 3/2/2 pool home in Siesta Isles is available for immediate occupancy. This impressive property offers 100 feet of waterfront along Siesta Key's Grand Canal. The gourmet kitchen features quartz counters, stainless steel appliances, built-in microwave/wall-oven combo, island cooktop with hood

Jennifer Herman MOUNT VERNON PROPERTY MGMT INC

935 Contento St, Sarasota, FL 34242
/2
$1,300,000 Sold Jun 30, 2025
- 1,886 Sq Ft
- $689/SF
- 98 Days On Market
- 3 Beds
- 2 Baths
- Built 1962
5402 Shadow Lawn Dr, Sarasota, FL 34242

Enjoy true Florida living on Siesta Key on this high & dry lot in beautiful Siesta Isles. This one level home offers nearly 1900 sf of living space set on a 104' wide deep-water canal lot with access to Roberts Bay, the Intracoastal, and the Gulf of Mexico. NO STORM DAMAGE during the recent hurricanes! Move right in and update it to make it your own. Offering a Split Plan of 3 bedrooms, two full

Jimmy Raybon BERKSHIRE HATHAWAY HOMESERVICE

5402 Shadow Lawn Dr, Sarasota, FL 34242

/68
Est $654,297 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
101 Whispering Sands Dr Unit 204TRO, Sarasota, FL 34242

101 Whispering Sands Dr Unit 204TRO, Sarasota, FL 34242

/40
$715,000
- 2 Beds
- 2 Baths
- 1,204 Sq Ft
1001 Beach Rd Unit A203, Sarasota, FL 34242

$34K Price Reduction + Seller Paying $45K Assessment! 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

Mike Winger RE/MAX PLATINUM

1001 Beach Rd Unit A203, Sarasota, FL 34242
/74
$6,000 per month
- 3 Beds
- 2 Baths
- 1,823 Sq Ft
- House for Rent
1224 S View Dr, Sarasota, FL 34242

Stunning Renovated Home for Long-Term Rent in Siesta Cove. Discover your dream coastal lifestyle in this beautifully renovated single-family home located in the exclusive neighborhood of Siesta Cove, just steps away from the acclaimed Siesta Key Beach—voted the number one beach in the United States! This elegant residence boasts 3 spacious bedrooms and 2 luxurious bathrooms, offering a high

Beth Dilley ASCENDIA REAL ESTATE

1224 S View Dr, Sarasota, FL 34242
/2
$1,860,000 Sold Jun 30, 2025
- 3,721 Sq Ft
- $500/SF
- 118 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1964
5376 Shadow Lawn Dr, Sarasota, FL 34242

BRING ALL THE FAMILY - MOVE IN READY! Florida living on this high & dry lot on Siesta Key. Your own private tropical deep-water canal frontage. Large saltwater pool and spa, private screened courtyard adjacent to a large game room and theater room – perfect for entertaining. NO STORM DAMAGE during the recent hurricanes! This 4 BR spacious home offers 3700+ sq. ft. of living space including two

Jimmy Raybon BERKSHIRE HATHAWAY HOMESERVICE

5376 Shadow Lawn Dr, Sarasota, FL 34242

/84
Est $602,041 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
5600 Beach Way Dr Unit 113, Sarasota, FL 34242

5600 Beach Way Dr Unit 113, Sarasota, FL 34242

/37
$3,288,000
- 3 Beds
- 3.5 Baths
- 2,885 Sq Ft
5169 Sandy Shore Ave, Sarasota, FL 34242

One or more photo(s) has been virtually staged. LIVE IN PARADISE | Turnkey Siesta Key waterfront luxury home on wide canal with dock + boat lift. VIEW 3D TOUR. Built in 2015 by award-winning builder Lee Wetherington and elevated at 10.5 feet, this 3 bed + den, 3.5 bath canal-front home offers quality construction, impact-rated windows, a 20kW generator, and a private dock with lift — just minutes

Andy Barnhardt WATERSIDE REALTY LLC

5169 Sandy Shore Ave, 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
$1,075,000 Sold Jun 30, 2025
- 1,337 Sq Ft
- $804/SF
- 186 Days On Market
- 2 Beds
- 2 Baths
- Built 1980
5770 Midnight Pass Rd Unit 705, Sarasota, FL 34242

Welcome to Gulf & Bay Club, the premiere Siesta Key condo complex nestled on 32 acres with 800 ft of private beach! Located in the middle of the C Building on the top floor, this condo offers fabulous views, both day and night, of the freshwater lake, fountains, island lagoon, swimming pools, sandy beach, and the Gulf of Mexico beyond. Take in the views on the Lanai, or sip your coffee in the

Tina Johns COLDWELL BANKER REALTY

5770 Midnight Pass Rd Unit 705, Sarasota, FL 34242

/27
Est $737,983 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,043 Sq Ft
5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242

5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242

/100
$699,000
- 2 Beds
- 2 Baths
- 1,290 Sq Ft
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

Crystal Saly RE/MAX PLATINUM

6415 Midnight Pass Rd Unit 909, 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, this home

Robert Bevington SHOWTIME REALTY

301 Avenida Madera Unit A, Sarasota, FL 34242
/2
$1,970,000 Sold Jun 27, 2025
- 2,088 Sq Ft
- $943/SF
- 7 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1970
5966 Midnight Pass Rd Unit G-51 & G-58, Sarasota, FL 34242

BREATHTAKING amazing Gulf of Mexico views and ONCE IN A LIFETIME OPPORTUNITY for this ONE-OF-A-KIND condominium residence in the desirable Gulffront Tower building in the Palm Bay Club on the island of Siesta Key. This turnkey furnished residence is a combined 2-bedroom unit with the adjacent 1-bedroom unit, redesigned to create a fabulous 2-bedroom plus den/study, which could be converted back

Carolyn Donnelly COLDWELL BANKER REALTY

5966 Midnight Pass Rd Unit G-51 & G-58, Sarasota, FL 34242

/53
Est $519,785 Not Listed For Sale
- 1 Bed
- 1 Bath
- 561 Sq Ft
44 Sandy Cove Rd Unit A4, Sarasota, FL 34242

44 Sandy Cove Rd Unit A4, 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
/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
$1,100,000 Sold Jun 27, 2025
- 2,519 Sq Ft
- $437/SF
- 83 Days On Market
- 3 Beds
- 3 Baths
- Built 1957
4857 Primrose Path, Sarasota, FL 34242

Welcome to your dream home in the highly sought-after Harmony subdivision! This stunning single-family residence is situated on a serene canal, featuring an impressive 120' of newer concrete seawall, perfect for those looking to embrace the waterfront lifestyle. Bring your boats and jet skis, as you can easily add your own dock, allowing for quick access to Sarasota Bay and the breathtaking blue

Nadiya Marisol-Pote MICHAEL SAUNDERS & COMPANY

4857 Primrose Path, Sarasota, FL 34242

/20
Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 5,986 Sq Ft
84 Avenida Veneccia Unit 202 & 203, Sarasota, FL 34242

84 Avenida Veneccia Unit 202 & 203, Sarasota, FL 34242

/73
$1,695,000 Pending
- 4 Beds
- 7 Baths
- 3,893 Sq Ft
4831 Primrose Path, Sarasota, FL 34242

Under contract-accepting backup offers. 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

Derek Edwards KELLER WILLIAMS ON THE WATER S

4831 Primrose Path, 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
$4,000,000 Sold Jun 26, 2025
- 4,989 Sq Ft
- $802/SF
- 441 Days On Market
- Built 2018
645 Beach Rd, Siesta Key, FL 34242

Featuring the highly coveted RMF zoning, this property offers legal short term rentals-a rarity across the region and a game-changer for income potential. Set on high ground, it has proven its durability by remaining high and dry during recent hurricanes, providing unmatched security and peace of mind.The property comes fully turnkey furnished, ensuring a seamless and effortless

Cole Collins COLDWELL BANKER REALTY

645 Beach Rd, Siesta Key, FL 34242

/77
Est $668,885 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

/48
$715,000 Pending
- 2 Beds
- 2 Baths
- 894 Sq Ft
6310 Midnight Pass Rd Unit 405N, Sarasota, FL 34242

Under contract-accepting backup offers. Welcome to 6310 Midnight Pass Rd #405N, an exceptional opportunity to own a turnkey furnished, income-producing beach retreat in the highly sought-after Crescent Arms community on Siesta Key. This rarely available 2-bedroom, 2-bathroom condo offers partial Gulf views from the spacious screened lanai and is just steps from private deeded beach access to

Halie Roberson KELLER WILLIAMS ON THE WATER S

6310 Midnight Pass Rd Unit 405N, 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 now through Dec 2025 for $2,000 per month. 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. Just a short

Jonathan OSteen O'STEEN GROUP INC

1300 N Portofino Dr Unit 205, Sarasota, FL 34242
/2
$990,000 Sold Jun 25, 2025
- 1,464 Sq Ft
- $676/SF
- 117 Days On Market
- 2 Beds
- 2 Baths
- Built 1973
20 Whispering Sands Dr Unit 306, Sarasota, FL 34242

***PRICE REDUCED*** This stunning beachfront condo offers a rare combination of luxury, convenience, and breathtaking natural beauty. Nestled on the powdery soft white sands of Siesta Key Beach, this end unit features an additional window which floods the space with an abundance of natural light and provides panoramic views of the sparkling Gulf of Mexico.This condo isn’t just a home;

Christa Spalding COLDWELL BANKER REALTY

20 Whispering Sands Dr Unit 306, Sarasota, FL 34242

/66
Est $585,656 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

/65
$1,395,000
- 4 Beds
- 3 Baths
- 1,962 Sq Ft
6150 Midnight Pass Rd Unit 10, Sarasota, FL 34242

A rare investment opportunity awaits with this proven income-producing property on world-renowned Siesta Key Beach. Located within the beautifully maintained Island House Beach Resort, this unique offering includes two units in one building, complete with a two-car carport and additional storage. Flexible rental options allow it to be used as a full 4-bedroom rental, two separate 2-bedroom units,

Lee Brewer RE/MAX ALLIANCE GROUP

6150 Midnight Pass Rd Unit 10, 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
$1,335,000 Sold Jun 25, 2025
- 1,335 Sq Ft
- $1000/SF
- 131 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
5790 Midnight Pass Rd Unit 602, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Location, Location, Location!***SPECTACULAR POOL, BEACH & GULF VIEWS***Welcome to the highly sought-after "Building A" at the Gulf & Bay Club located on Siesta Key Beach (voted America's #1 beach by Trip Advisor)! This is where you'll find this completely updated condo with gorgeous beach and gulf views! Where you'll be just steps to private beach

Jamie Mullis COLDWELL BANKER REALTY

5790 Midnight Pass Rd Unit 602, Sarasota, FL 34242

/41
Est $670,809 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

/62
$1,785,000
- 3 Beds
- 2 Baths
- 1,972 Sq Ft
5164 Windward Ave, Sarasota, FL 34242

***SELLER FINANCING AVAILABLE*** Tucked away on a quiet dead-end street, this exceptional waterfront estate on Siesta Key offers the perfect balance of seclusion and accessibility. Situated on an oversized 0.40-acre corner lot with 260 feet of water frontage and coveted western exposure, the property provides direct access to the Intracoastal Waterway—ideal for boating enthusiasts and water

Taylor Thompson WILLIAM RAVEIS REAL ESTATE

5164 Windward Ave, Sarasota, FL 34242
/71
$3,550 per month
- 2 Beds
- 2 Baths
- 1,217 Sq Ft
- Condo for Rent
1269 Dockside Place Unit 115, Sarasota, FL 34242

A BOATER'S PARADISE! THE BEST OF THE BEACH AND THE BAY!! Great canal front first floor condo with large deck! Best of both worlds - across the street from Siesta Beach and a gated bayside community open to the intracoastal. Large kitchen with granite countertops, open to living/dining room. Bonus Florida room with plantation shuttered sliders that recess for an open air concept. Two bedroom, each

Susan Brooks COLDWELL BANKER SUNSTAR REALTY

1269 Dockside Place Unit 115, Sarasota, FL 34242
/2
$45,000 Sold Jun 24, 2025
- 1,780 Sq Ft
- $25/SF
- 47 Days On Market
- 3 Beds
- 3 Baths
- Built 2009
915 Seaside Dr Unit 606, Weeks 6-7, 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

915 Seaside Dr Unit 606, Weeks 6-7, Sarasota, FL 34242

/2
Est $793,905 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

/65
$1,400,000
- 2 Beds
- 2 Baths
- 1,770 Sq Ft
6281 Midnight Pass Rd Unit 6281, Sarasota, FL 34242

Rarely Available 2-Bedroom Waterfront Villa with Deeded Beach Access on Siesta KeyWelcome to this exceptional waterfront residence at the highly sought-after Excelsior Beach to Bay, where coastal luxury, elegant interiors, and breathtaking Intracoastal Waterway views come together to define tropical paradise living on Siesta Key. This beautifully updated and fully furnished 2-bedroom,

Jackie Eberley COLDWELL BANKER REALTY

6281 Midnight Pass Rd Unit 6281, 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- clean and 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 suit and

Robert Bevington SHOWTIME REALTY

6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242
/2
$1,200,000 Sold Jun 24, 2025
- 2,308 Sq Ft
- $520/SF
- 163 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1963
5140 Windward Ave, Sarasota, FL 34242

A fabulous boating water opportunity - $345,000 price reduction! Professionally remediated and ready for renovation or to build your new luxury home. Welcome to your private, gated garden oasis nestled on boating water in the heart of Siesta Key. Boasting a seamless blend of indoor-outdoor living spaces, this three-bedroom, two-and-a-half-bath residence was storm-damaged, remediated, sanitized,

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

5140 Windward Ave, Sarasota, FL 34242

/68
Est $551,032 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

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