Osprey, FL Homes

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  $1,570,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,913 Sq Ft

  360 N Point Rd, Osprey, FL 34229

  **DON’T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure Gates of the COVETED, OAKS PRESERVE Country Club Neighborhood on Sarasota Bay waters offers superb attention to detail. This Custom-Built residence boasts 3 EN SUITE BEDROOMS + 3 FULL and 1 HALF BATHS and a desirable Open Floorplan concept. A well-equipped Chef’s Kitchen features

  Mark Lyda GENEROUS PROPERTY

  360 N Point Rd, Osprey, FL 34229
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  $5,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,950 Sq Ft
  • Condo for Rent

  260 Hidden Bay Dr Unit B-504, Osprey, FL 34229

  Annual Turnkey Furnished or short term seasonal Penthouse on the Bay! If you want mesmerizing views of intracoastal waterway, Little Sarasota Bay, Casey Key, and the Gulf of Mexico in a beautiful, comfortable and roomy penthouse, then this could be your next home. This natural light filled delight is 2 bedrooms, each with en suite bathroom, separate office with large closet and glass French

  Henry Rossi RENT SARASOTA

  260 Hidden Bay Dr Unit B-504, Osprey, FL 34229
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  $340,000 Sold May 08, 2025

  294 Hidden Bay Dr Unit 103, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2001

  Last Sold Summary

  • 20% Below List Price
  • $217/SF
  • 166 Days On Market

  Current Estimated Value $348,719

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  294 Hidden Bay Dr Unit 103, Osprey, FL 34229
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  Est $43,328 Not Listed For Sale

  • Studio

  570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229

  570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229
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  $879,000

  • 3 Beds
  • 3 Baths
  • 2,622 Sq Ft

  903 Tranquility Cir, Osprey, FL 34229

  **IMPRESSIVE POOL/SPA HOME on a Desirable Corner Lot with Partial Water View** Custom-built by John Cannon and situated on an interior Cul De Sac in popular North Creek Estates, this 3-BED + Office/Den, 3 FULL BATH, 2-Car Garage residence affords wonderful privacy and features 2622sf of heated living area plus a spacious screened lanai with Heated Pool/Spa and ample covered seating area, for the

  Mark Lyda GENEROUS PROPERTY

  903 Tranquility Cir, Osprey, FL 34229
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  $6,500 per month

  • 3 Beds
  • 3 Baths
  • 2,266 Sq Ft
  • House for Rent

  521 Habitat Blvd, Osprey, FL 34229

  REDUCED FOR THE SEASON! Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 60 Day minimum stay in Peak Season at $8,900/mo plus fees; Minimum 60 Day stay in Off Season at $6,500/mo plus fees. Your Gulf Coast getaway awaits at this beautifully furnished 3-bedroom, 3-bath pool home in the scenic Willowbend community of Osprey, FL. Ideal for mid-term stays, this spacious

  Dave Holt PMI SOUTHWEST FLORIDA

  521 Habitat Blvd, Osprey, FL 34229
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  /2

  $235,000 Sold Jun 13, 2025

  109 Woodland Place, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,223 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $192/SF
  • 144 Days On Market

  Current Estimated Value $232,016

  Last Listing Agent Derek Edwards KELLER WILLIAMS ON THE WATER S

  109 Woodland Place, Osprey, FL 34229
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  Not Listed For Sale

  0 N Point Rd Unit MFRA4600038, Osprey, FL 34229

  0 N Point Rd Unit MFRA4600038, Osprey, FL 34229
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  $1,695,000

  • 3 Beds
  • 3.5 Baths
  • 4,241 Sq Ft

  909 MacEwen Dr, Osprey, FL 34229

  **STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious

  Mark Lyda GENEROUS PROPERTY

  909 MacEwen Dr, Osprey, FL 34229
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  $6,000 per month

  • 3 Beds
  • 2 Baths
  • 2,143 Sq Ft
  • Condo for Rent

  5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229

  CLOSE TO NOKOMIS BEACH! AVAILABLE JAN/FEB/MAR/APR 2026 $6,000/MONTH. Beautiful waterfront 5th Floor condo located in Blackburn Harbor Residences with breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was converted from a den) and

  Chrissie Cummings JENNETTE PROPERTIES INC

  5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
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  /55

  $480,000 Sold May 14, 2025

  564 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,808 Sq Ft
  • Built 2003

  Last Sold Summary

  • 15% Below List Price
  • $265/SF
  • 57 Days On Market

  Current Estimated Value $484,128

  Last Listing Agent Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  564 Meadow Sweet Cir, Osprey, FL 34229
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  Est $1,091,294 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,323 Sq Ft

  3925 Waypoint Ave, Osprey, FL 34229

  3925 Waypoint Ave, Osprey, FL 34229
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  $589,900

  • 2 Beds
  • 2 Baths
  • 1,932 Sq Ft

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229

  Stunning, unobstructed views of the Intracoastal Waterway, Little Sarasota Bay, and the Gulf await from this beautiful Penthouse residence in Baypoint Vista, Osprey. Located within Hidden Bay, a gated and amenity rich community, this exceptional condo features 2 Bedrooms, 2 Bathrooms plus a versatile Den, an open floor plan, high ceilings, recessed lighting, a spacious kitchen, morning room,

  Susan Retzke RE/MAX PALM

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229
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  $2,995 per month

  • 2 Beds
  • 3.5 Baths
  • 1,890 Sq Ft
  • Townhouse for Rent

  60 Bishops Court Rd Unit 114, Osprey, FL 34229

  This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing charming architectural details and quality finishes, this traditional-style home offers an inviting floor plan with two bedrooms, each featuring its own en-suite bath. The gracious living and dining areas flow seamlessly into a spacious and private outdoor living space that

  Heidi Thompson STRINGER MANAGEMENT INC

  60 Bishops Court Rd Unit 114, Osprey, FL 34229
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  $350,000 Sold Oct 16, 2025

  240 Patterson Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,360 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $257/SF
  • 157 Days On Market

  Current Estimated Value $342,961

  Last Listing Agent Janice Melzer Langa COLDWELL BANKER REALTY

  240 Patterson Ave, Osprey, FL 34229
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  Est $1,071,315 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,314 Sq Ft

  3937 Waypoint Ave, Osprey, FL 34229

  3937 Waypoint Ave, Osprey, FL 34229
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  $1,575,000

  • 4 Beds
  • 3 Baths
  • 3,486 Sq Ft

  20 Bayhead Ln, Osprey, FL 34229

  A rare opportunity to own a significantly newer, custom-built residence inside the exclusive The Oaks Club Preserve, where most surrounding homes were built decades earlier. Completed in 2017 and set on a lakefront lot in a non-flood zone, this move-in-ready, hurricane-secure home offers a level of modern construction, privacy, and peace of mind seldom found in this exclusive community. In

  Lielei Wahlmann EXP REALTY LLC

  20 Bayhead Ln, Osprey, FL 34229
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  $6,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,839 Sq Ft
  • Townhouse for Rent

  101 Woodland Place, Osprey, FL 34229

  Price Reduction and Now AVAILABLE FOR LEASE for FEBRUARY through APRIL 2026 at PINE RUN Condominiums in OSPREY, Florida! One month availability. 3BR/2.5BA Great SARASOTA Vacation Location! West of the Trail, Pine Run is an active community set in a tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of

  Patrice Ivan WAGNER REALTY

  101 Woodland Place, Osprey, FL 34229
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  $1,285,000 Sold Jun 30, 2025

  393 N Point Rd Unit 801, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,029 Sq Ft
  • Built 2001

  Last Sold Summary

  • 22% Below List Price
  • $424/SF
  • 204 Days On Market

  Current Estimated Value $1,278,209

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  393 N Point Rd Unit 801, Osprey, FL 34229
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  /22

  Est $291,255 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft

  101 Navigation Cir Unit 101, Osprey, FL 34229

  101 Navigation Cir Unit 101, Osprey, FL 34229
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  $2,250,000

  • 4 Beds
  • 3.5 Baths
  • 4,012 Sq Ft

  433 E MacEwen Dr, Osprey, FL 34229

  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 course and water views and 24 hr gated security. This custom golf course home was built by esteemed builder Arthur Rutenberg. It represents Rutenberg at his very best - stylish elegance, superior

  Mark Lyda GENEROUS PROPERTY

  433 E MacEwen Dr, Osprey, FL 34229
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  $5,900 per month

  • 3 Beds
  • 3 Baths
  • 2,545 Sq Ft
  • Condo for Rent

  3603 N Point Rd Unit 602, Osprey, FL 34229

  **FURNISHED, 3-BED / 3-FULL BATH, Over 2500sf CONDO with FANTASTIC VIEW** features an Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Spacious interior which boasts beautiful Crown Moldings, Hardwood Floors, a well-equipped Kitchen with granite

  Mark Lyda GENEROUS PROPERTY

  3603 N Point Rd Unit 602, Osprey, FL 34229
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  $925,000 Sold Mar 03, 2025

  1200 Mallard Marsh Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,928 Sq Ft
  • Built 2002

  Last Sold Summary

  • 21% Below List Price
  • $316/SF
  • 118 Days On Market

  Current Estimated Value $919,627

  Last Listing Agent Sharon Osborne, PA RESULTS REALTY GROUP LLC

  1200 Mallard Marsh Dr, Osprey, FL 34229
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  Est $300,077 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  163 Explorer Dr Unit 103, Osprey, FL 34229

  163 Explorer Dr Unit 103, Osprey, FL 34229
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  $2,495,000

  • 3 Beds
  • 3.5 Baths
  • 4,519 Sq Ft

  852 MacEwen Dr, Osprey, FL 34229

  **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 interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and

  Mark Lyda GENEROUS PROPERTY

  852 MacEwen Dr, Osprey, FL 34229
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  $7,000 per month

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft
  • Condo for Rent

  14041 Bellagio Way Unit 316, Osprey, FL 34229

  *BOOKED DEC THROUGH JUNE 2026.* MINS TO CASEY KEY & NOKOMIS BEACH! Welcome to BELLAGIO at Osprey Harbor Village, offering luxurious waterfront living! This turnkey direct waterfront condo has 3 beds/2 baths plus a den is the perfect place for your next Florida vacation, located in a private gated community. As you step off the elevator, you are basically outside this 3rd floor end unit. Upon

  Chrissie Cummings JENNETTE PROPERTIES INC

  14041 Bellagio Way Unit 316, Osprey, FL 34229
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  $904,900 Sold May 30, 2025

  336 Pine Ranch Rd E, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,705 Sq Ft
  • Built 1989

  Last Sold Summary

  • 9% Below List Price
  • $335/SF
  • 5 Days On Market

  Current Estimated Value $931,443

  Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

  336 Pine Ranch Rd E, Osprey, FL 34229
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft

  201 Palm Air Dr, Osprey, FL 34229

  201 Palm Air Dr, Osprey, FL 34229
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  $1,995,000

  • 3 Beds
  • 3 Baths
  • 3,029 Sq Ft

  401 N Point Rd Unit 1001, Osprey, FL 34229

  **Rarely available 10th-floor penthouse corner residence offering 3,029 square feet with sweeping Gulf and Bay views.** Ideally situated behind the secure gates of the highly sought-after Preserve neighborhood within The Oaks Country Club, this exceptional condo features 3 Bedrooms plus Den, 3 Full Baths, Private 2-Car Garage, and climate-controlled storage. The open-concept floor plan is

  Mark Lyda GENEROUS PROPERTY

  401 N Point Rd Unit 1001, Osprey, FL 34229
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  /25

  $4,500 per month

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Condo for Rent

  152 Navigation Cir Unit 107, Osprey, FL 34229

  BACIK ON THE MARKET HIGH SEASON NOW AVAILABLE!! Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with

  Henry Rossi RENT SARASOTA

  152 Navigation Cir Unit 107, Osprey, FL 34229
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  $430,000 Sold Aug 01, 2025

  117 Villa Dr Unit 117, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • Built 1967

  Last Sold Summary

  • 22% Below List Price
  • $305/SF
  • 244 Days On Market

  Current Estimated Value $424,038

  Last Listing Agent Bill Garrison RE/MAX PALM

  117 Villa Dr Unit 117, Osprey, FL 34229
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  Est $638,412 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  2007 Cordes St, Osprey, FL 34229

  2007 Cordes St, Osprey, FL 34229
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  $2,850,000

  • 4 Beds
  • 4 Baths
  • 4,359 Sq Ft

  662 Fernwalk Ln, Osprey, FL 34229

  **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). Located behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. This expansive residence features 4 Bedrooms and 4

  Mark Lyda GENEROUS PROPERTY

  662 Fernwalk Ln, Osprey, FL 34229
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  $2,300 per month

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft
  • Property for Rent

  184 Explorer Dr Unit 184, Osprey, FL 34229

  Property available for $2300 from April 1,2024 till November 30,2024. Tenant pays electricity and internet. Available for season 2024/2025 for $4500. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling two-bedroom, two-bath, impeccably maintained, property move-in ready. Located on the

  Claudia Dybala DALTON WADE INC

  184 Explorer Dr Unit 184, Osprey, FL 34229
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  $1,051,025 Sold Apr 04, 2025

  280 Hidden Bay Dr Unit 502, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Above List Price
  • $543/SF
  • 2 Days On Market

  Current Estimated Value $1,034,152

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 502, Osprey, FL 34229
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  Not Listed For Sale

  0 N Point Rd Unit A11454780, Osprey, FL 34229

  0 N Point Rd Unit A11454780, Osprey, FL 34229
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  $1,695,000

  • 3 Beds
  • 3.5 Baths
  • 3,066 Sq Ft

  25 Sugar Mill Dr, Osprey, FL 34229

  METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite

  Mark Lyda GENEROUS PROPERTY

  25 Sugar Mill Dr, Osprey, FL 34229
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  $925,000 Sold Mar 25, 2025

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  Last Sold Summary

  • $478/SF
  • 0 Days On Market

  Current Estimated Value $915,060

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229
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  Est $304,354 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  4219 Frontier Ln Unit 105, Osprey, FL 34229

  4219 Frontier Ln Unit 105, Osprey, FL 34229
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  $1,175,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  219 Keel Way, Osprey, FL 34229

  Under contract-accepting backup offers. **IMPRESSIVE, METICULOUSLY MAINTAINED, SINGLE-STORY, CUL DE SAC ESTATE in the Highly Sought-After SOUTHBAY Community** offers 3 BEDS, 2 FULL and 1 HALF BATHS plus STUDY/DEN – and is nearly 100% SOLAR-POWERED (details available)! This Custom and Updated home offers many premium features including elegant Bolivian woodwork, beautiful tile floors throughout,

  Mark Lyda GENEROUS PROPERTY

  219 Keel Way, Osprey, FL 34229

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