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  1. Krista Plagge, REALTOR ®
  2. Tropic Shores Realty
  3. Mobile: 813.285.1702
  4. krista@homeguidetampa.com
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  1. City = Osprey
1216 Casey Key Road
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Details for 1216 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $11,750,000.00
  2. Price sqft: $756.99 / sqft
  3. Days On Market: 203
  4. Bedrooms: 5
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 15522
  8. Acreage: 1.10 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Bay/Harbor,Beach Front,Gulf/Ocean,Gulf/Ocean to Bay,Intracoastal Waterway
  14. Year Built: 1999
MLS#: A4643654
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Casey Key
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: PREMIER SOTHEBYS INTL REALTY
  9. mfrmls
  10. DMCA Notice
This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on t
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144 Casey Key Road
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Details for 144 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $6,490,000.00
  2. Price sqft: $605.30 / sqft
  3. Previous Price: $6,790,000
  4. Last Price Change: 09/06/25
  5. Days On Market: 49
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 10722
  10. Acreage: 0.55 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Bay/Harbor
  16. Year Built: 2003
MLS#: A4660004
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Casey Key
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: DOUGLAS ELLIMAN
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A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless residence blends architectural elegance with waterfront living. Offering private access to the Intracoastal wit
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622 Bayshore Drive
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Details for 622 Bayshore Drive, Osprey, FL 34229
Single Family
  1. Price: $5,700,000.00
  2. Price sqft: $977.37 / sqft
  3. Previous Price: $6,750,000
  4. Last Price Change: 07/13/25
  5. Days On Market: 85
  6. Bedrooms: 6
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5832
  10. Acreage: 0.78 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: BayAccess
  15. Year Built: 2022
MLS#: A4657777
  1. County: SARASOTA
  2. City: Osprey
  3. Zipcode: 34229
  4. Subdivision: Bay Acres Resub
  5. High School: Pine View
  6. Provided by: MICHAEL SAUNDERS & COMPANY
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ELEVATED ABOVE FLOOD LEVEL WITH EXCEPTIONALLY LOW INSURANCE PREMIUMS ! Welcome to 622 Bayshore Drive where coastal luxury meets modern sophistication on one of the most sought after stretches of L
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622 Bayshore Drive
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Details for 622 Bayshore Drive, OSPREY, FL 34229
Single Family
  1. Price: $5,700,000.00
  2. Price sqft: $977.37 / sqft
  3. Previous Price: $6,750,000
  4. Last Price Change: 08/11/25
  5. Days On Market: 85
  6. Bedrooms: 6
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5832
  10. Acreage: 0.78 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Bay/Harbor
  16. Year Built: 2022
MLS#: A4657777
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Bay Acres Resub
  5. High School: Pine View
  6. Provided by: MICHAEL SAUNDERS & COMPANY
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ELEVATED ABOVE FLOOD LEVEL WITH EXCEPTIONALLY LOW INSURANCE PREMIUMS ! Welcome to 622 Bayshore Drive where coastal luxury meets modern sophistication on one of the most sought after stretches of L
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614 Bayshore Drive
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Details for 614 Bayshore Drive, OSPREY, FL 34229
Single Family
  1. Price: $5,500,000.00
  2. Price sqft: $866.55 / sqft
  3. Days On Market: 42
  4. Bedrooms: 3
  5. Baths: 5
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 6347
  8. Acreage: 0.52 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Bay/Harbor
  14. Year Built: 2024
MLS#: A4662210
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Bay Acres Resub
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: DOUGLAS ELLIMAN
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Commanding over half an acre with 116 feet of pristine frontage on Little Sarasota Bay, this brand new custom estate captures the essence of coastal luxury. From the moment you arrive, you are greeted
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101 Osprey Point Drive
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Details for 101 Osprey Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $5,000,000.00
  2. Price sqft: $730.89 / sqft
  3. Days On Market: 9
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6841
  8. Acreage: 0.93 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front
  14. Year Built: 1985
MLS#: A4664424
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: The Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: DOUGLAS ELLIMAN
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A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one
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1049 Casey Key Road
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Details for 1049 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $4,750,000.00
  2. Price sqft: $1,408.24 / sqft
  3. Days On Market: 199
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 3373
  8. Acreage: 1.06 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Bay/Harbor,Gulf/Ocean,Gulf/Ocean to Bay,Intracoastal Waterway
  13. Year Built: 1990
MLS#: N6137711
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Casey Key
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: PREMIER SOTHEBYS INTL REALTY
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Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one plus acre estate, with 107 feet of pristine gulf frontage, a walkable sandy beach, on a private ro
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135 Tina Island Drive
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Details for 135 Tina Island Drive, OSPREY, FL 34229
Single Family
  1. Price: $3,450,000.00
  2. Price sqft: $1,341.37 / sqft
  3. Days On Market: 9
  4. Bedrooms: 3
  5. Baths: 5
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 2572
  8. Acreage: 0.37 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Canal Front
  13. Year Built: 1965
MLS#: A4665474
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Sorrento Shores
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: FLATFEE.COM
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Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers de
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112 Osprey Point Drive
Foreclosure
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Details for 112 Osprey Point Drive, Osprey, FL 34229
Single Family
  1. Price: $3,325,000.00
  2. Price sqft: $300.20 / sqft
  3. Previous Price: $3,500,000
  4. Last Price Change: 09/08/25
  5. Days On Market: 145
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 11076
  10. Acreage: 0.60 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: BayAccess,IntracoastalAccess
  16. Year Built: 1989
MLS#: O6305818
  1. County: SARASOTA
  2. City: Osprey
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Venice Area
  7. High School: Venice Senior
  8. Provided by: KARA MONEY LLC
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Premier Waterfront Opportunity in The Oaks Bayside This grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers swee
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112 Osprey Point Drive
Foreclosure
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Details for 112 Osprey Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $3,325,000.00
  2. Price sqft: $300.20 / sqft
  3. Previous Price: $3,500,000
  4. Last Price Change: 09/08/25
  5. Days On Market: 145
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 11076
  10. Acreage: 0.60 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Bay/Harbor,Intracoastal Waterway
  15. Year Built: 1989
MLS#: O6305818
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Venice Area
  7. High School: Venice Senior
  8. Provided by: KARA MONEY LLC
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  10. DMCA Notice
Premier Waterfront Opportunity in The Oaks Bayside This grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers swee
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