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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: 165
  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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854 Macewen Drive
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Details for 854 Macewen Drive, OSPREY, FL 34229
Single Family
  1. Price: $3,890,000.00
  2. Price sqft: $333.91 / sqft
  3. Previous Price: $3,950,000
  4. Last Price Change: 01/28/26
  5. Days On Market: 133
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 11650
  10. Acreage: 0.78 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2003
MLS#: A4668918
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks 2 Ph 2
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: COLDWELL BANKER REALTY
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One or more photo(s) has been virtually staged. Set on a private cul de sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home
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662 Fernwalk Lane
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Details for 662 Fernwalk Lane, OSPREY, FL 34229
Single Family
  1. Price: $2,850,000.00
  2. Price sqft: $452.38 / sqft
  3. Days On Market: 31
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6300
  8. Acreage: 0.44 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1989
MLS#: A4679996
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: GENEROUS PROPERTY
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**exceptional, fully renovated, country club estate home offering tranquil lake and garden views** ideally positioned on a serene interior cul de sac lot in flood zone x (no flood insurance required).
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236 Saint James Park
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Details for 236 Saint James Park, OSPREY, FL 34229
Single Family
  1. Price: $2,700,000.00
  2. Price sqft: $281.57 / sqft
  3. Previous Price: $2,900,000
  4. Last Price Change: 11/25/25
  5. Days On Market: 339
  6. Bedrooms: 6
  7. Baths: 7
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 9589
  10. Acreage: 0.56 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 1986
MLS#: A4644125
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks 2 Ph 1
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: MICHAEL SAUNDERS & COMPANY
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Tucked away in a quiet cul de sac on a sprawling double lot beneath majestic oaks, this nearly 5,000 sq ft timeless 2 story residence blends classic elegance with modern luxury. Perfectly positioned o
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49 Osprey Point Drive
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Details for 49 Osprey Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $2,500,000.00
  2. Price sqft: $478.29 / sqft
  3. Previous Price: $2,595,000
  4. Last Price Change: 01/30/26
  5. Days On Market: 108
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5227
  10. Acreage: 0.40 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Front
  16. Year Built: 1989
MLS#: A4671762
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: MICHAEL SAUNDERS & COMPANY
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Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blen
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852 Macewen Drive
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Details for 852 Macewen Drive, OSPREY, FL 34229
Single Family
  1. Price: $2,495,000.00
  2. Price sqft: $414.52 / sqft
  3. Previous Price: $2,550,000
  4. Last Price Change: 01/10/26
  5. Days On Market: 224
  6. Bedrooms: 3
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6019
  10. Acreage: 0.64 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 1992
MLS#: A4659276
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks 2 Ph 2
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: GENEROUS PROPERTY
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**charming and private, golf course estate** is located behind the secure gates of the highly sought after oaks country club community and offers a lovely, golf course view of the 17th fairway of the
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530 Mac Ewen Drive
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Details for 530 Mac Ewen Drive, OSPREY, FL 34229
Single Family
  1. Price: $2,400,000.00
  2. Price sqft: $411.17 / sqft
  3. Days On Market: 9
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5837
  8. Acreage: 0.61 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2002
MLS#: A4683029
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks 2 Ph 4c Pt 3
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: LPT REALTY, LLC
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Located in the prestigious gated community of The Oaks Golf & Country Club in Osprey (Sarasota area), this elegant single story residence at 530 N Mac Ewen Drive offers resort style living with champi
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393 N Point Road 1002
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Details for 393 N Point Road 1002, OSPREY, FL 34229
Condominium
  1. Price: $2,350,000.00
  2. Price sqft: $545.12 / sqft
  3. Days On Market: 139
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4311
  8. Acreage: 0.00 acres
  9. Pool: No
  10. Community Pool: Yes
  11. Spa/HotTub: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Bay/Harbor
  15. Year Built: 2001
MLS#: A4667964
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Meridian At The Oaks
  5. Building: Meridian At The Oaks
  6. Elementary School: Gulf Gate
  7. Middle School: Brookside
  8. High School: Riverview
  9. Provided by: COLDWELL BANKER REALTY
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Experience Unmatched Luxury in this Meridian Penthouse! Welcome to the epitome of luxury living at Meridian at The Oaks Preserve. This stunning 3 bedroom, 2.5 bath penthouse offers a private 2 car gar
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433 Macewen Drive
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Details for 433 Macewen Drive, OSPREY, FL 34229
Single Family
  1. Price: $2,250,000.00
  2. Price sqft: $396.83 / sqft
  3. Days On Market: 61
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5670
  8. Acreage: 0.61 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1998
MLS#: A4676505
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: GENEROUS PROPERTY
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An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acre lot in the private Oaks Club community. It has golf
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362 Macewen Drive
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Details for 362 Macewen Drive, OSPREY, FL 34229
Single Family
  1. Price: $2,249,000.00
  2. Price sqft: $410.55 / sqft
  3. Days On Market: 48
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5478
  8. Acreage: 0.59 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1998
MLS#: A4676567
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks 2 Ph 1
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: COLDWELL BANKER REALTY
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Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowin
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