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- Subdivision Like Siestas Bayside
- Listing Status = Active
- 1
Single Family
- Price: $5,500,000.00
- Price sqft: $916.67 / sqft
- Days On Market: 154
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 3
- Bldg sqft: 6000
- Acreage: 0.26 acres
- Pool: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Canal - Saltwater
- Year Built: 2026
MLS#: A4672499
- County: SARASOTA
- City: SARASOTA
- Zipcode: 34242
- Subdivision: Siestas Bayside Waterside East
- Provided by: COMPASS FLORIDA LLC
- DMCA Notice
Pre Construction. To be built. Welcome to a world where every day feels like an escape to Paradise! This meticulously crafted 4,500 sq. ft. residence on Siesta Key blends contemporary architecture wit
Single Family
- Price: $4,649,900.00
- Price sqft: $844.82 / sqft
- Days On Market: 13
- Bedrooms: 5
- Baths: 5
- Garage / Parking Spaces: 2
- Bldg sqft: 5504
- Acreage: 0.21 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Canal - Saltwater
- Year Built: 2025
MLS#: A4689132
- County: SARASOTA
- City: SARASOTA
- Zipcode: 34242
- Subdivision: Siestas Bayside Waterside East
- Elementary School: Phillippi Shores
- Middle School: Brookside
- High School: Riverview
- Provided by: COMPASS FLORIDA LLC
- DMCA Notice
Newly completed and move in ready, this Coastal Contemporary waterfront residence on Siesta Key by award winning Heritage Builders offers 4,132 sq ft with 5 bedrooms, 4.5 baths, a private study, loft,
Single Family
- Price: $3,799,000.00
- Price sqft: $1,102.44 / sqft
- Days On Market: 19
- Bedrooms: 5
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3446
- Acreage: 0.75 acres
- Pool: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Canal Front
- Year Built: 1972
MLS#: A4688871
- County: SARASOTA
- City: SARASOTA
- Zipcode: 34242
- Subdivision: Siestas Bayside
- Middle School: Sarasota Middle
- High School: Sarasota High
- Provided by: FLATFEE.COM
- DMCA Notice
Welcome to Your Slice of Paradise. A Boaters Dream on Siesta Key
Rare waterfront compound on nearly 1 acre in the heart of Siesta Key. This 5 bedroom estate features 100+ feet of deep water frontage,
Single Family
- Price: $2,450,000.00
- Price sqft: $894.16 / sqft
- Previous Price: $2,495,000
- Last Price Change: 04/19/26
- Days On Market: 134
- Bedrooms: 3
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 2740
- Acreage: 0.26 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Canal - Saltwater
- Year Built: 1969
MLS#: A4674684
- County: SARASOTA
- City: SARASOTA
- Zipcode: 34242
- Subdivision: Siestas Bayside Waterside Wood
- Elementary School: Phillippi Shores Elementary
- Middle School: Brookside Middle
- High School: Sarasota High
- Provided by: KELLER WILLIAMS ON THE WATER S
- DMCA Notice
Luxury Waterfront Living Now Priced to Move
Welcome to 4508 Woodside Rd, a true boaters paradise on Siesta Key offering privacy, deep water access, and refined coastal living. Positioned on one of
Single Family
- Price: $1,575,000.00
- Price sqft: $437.87 / sqft
- Days On Market: 138
- Bedrooms: 4
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 3597
- Acreage: 0.44 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1984
MLS#: A4673529
- County: SARASOTA
- City: SARASOTA
- Zipcode: 34242
- Subdivision: Siestas Bayside Bayside Club 0
- Elementary School: Phillippi Shores Elementary
- Middle School: Brookside Middle
- High School: Sarasota High
- Provided by: PREMIER SOTHEBY'S INTERNATIONAL REALTY
- DMCA Notice
A private tropical haven in the heart of Siesta Key, beautifully reimagined coastal retreat tucked away on nearly half an acre in one of Siesta Keys most coveted neighborhoods. This stunning four bedr
Single Family
- Price: $1,072,000.00
- Price sqft: $392.10 / sqft
- Days On Market: 1
- Bedrooms: 3
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 2734
- Acreage: 0.30 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1972
MLS#: A4686684
- County: SARASOTA
- City: Sarasota
- Zipcode: 34242
- Subdivision: Siestas Bayside Waterside East
- Elementary School: Phillippi Shores
- Middle School: Brookside
- High School: Sarasota
- Provided by: MICHAEL SAUNDERS & COMPANY
- Provided through
- DMCA Notice
Island living meets easy everyday comfort in this turnkey furnished Siesta Key pool home. With 3 bedrooms, 2 bathrooms, approximately 2,168 square feet of living space and a 2 car garage, there is roo
Single Family
- Price: $1,072,000.00
- Price sqft: $392.10 / sqft
- Days On Market: 1
- Bedrooms: 3
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 2734
- Acreage: 0.30 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1972
MLS#: A4686684
- County: SARASOTA
- City: SARASOTA
- Zipcode: 34242
- Subdivision: Siestas Bayside Waterside East
- Elementary School: Phillippi Shores
- Middle School: Brookside
- High School: Sarasota
- Provided by: MICHAEL SAUNDERS & COMPANY
- DMCA Notice
Island living meets easy everyday comfort in this turnkey furnished Siesta Key pool home. With 3 bedrooms, 2 bathrooms, approximately 2,168 square feet of living space and a 2 car garage, there is roo
Single Family
- Price: $999,900.00
- Price sqft: $363.47 / sqft
- Previous Price: $1,150,000
- Last Price Change: 04/17/26
- Days On Market: 171
- Bedrooms: 3
- Baths: 2
- Garage / Parking Spaces: 1
- Bldg sqft: 2751
- Acreage: 0.36 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1973
MLS#: A4670796
- County: SARASOTA
- City: SARASOTA
- Zipcode: 34242
- Subdivision: Siestas Bayside Waterside Sout
- Elementary School: Phillippi Shores Elementary
- Middle School: Brookside Middle
- High School: Sarasota High
- Provided by: COLDWELL BANKER REALTY
- DMCA Notice
Experience Coastal Living at its finest in this turnkey furnished, three bedroom, two bath retreat tucked away on a quiet cul de sac in a private community just minutes from the beach! This home featu
Single Family
- Price: $975,000.00
- Price sqft: $363.40 / sqft
- Previous Price: $1,000,000
- Last Price Change: 03/27/26
- Days On Market: 177
- Bedrooms: 4
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 2683
- Acreage: 0.25 acres
- Pool: No
- Waterfront: No
- Year Built: 1971
MLS#: A4669940
- County: SARASOTA
- City: SARASOTA
- Zipcode: 34242
- Subdivision: Siestas Bayside Waterside East
- Elementary School: Phillippi Shores Elementary
- Middle School: Brookside Middle
- High School: Sarasota High
- Provided by: MICHAEL SAUNDERS & COMPANY
- DMCA Notice
One or more photo(s) has been virtually staged. Nestled near the gentle waters of Roberts Bay, this enchanting Siesta Key home rests on a quiet cul de sac street where the only sounds are the whisper
Rental
- Price: $5,525.00
- Price sqft: $2.04 / sqft
- Previous Price: $5,250
- Last Price Change: 02/23/26
- Days On Market: 472
- Bedrooms: 3
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 2707
- Acreage: 0.18 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1972
MLS#: A4634095
- County: SARASOTA
- City: SARASOTA
- Zipcode: 34242
- Subdivision: Siestas Bayside Waterside Sout
- Provided by: TNG PROPERTY MANAGEMENT
- DMCA Notice
AVAILABLE after April 15, 2026! WOW! Enjoy a little slice of heaven on the World Famous Siesta Key! This beautifully renovated turnkey 3 bedroom 2 bath, heated pool home, is just a short distance to t
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Listing Data ©2026 Royal Palm Coast Realtor® Association
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Datafeed Last updated on April 24, 2026 @ 12:00 am
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