Osprey, FL Homes

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  /98

  $949,000

  • 3 Beds
  • 3.5 Baths
  • 3,771 Sq Ft

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Waterfront Elegance at Blackburn Harbor! Experience the comfort of a home with the convenience of condo living in this spacious 3-bedroom, 3.5-bath plus den residence offering 3,771 sq. ft. of beautifully designed space and 10-foot tray ceilings throughout and a new roof. Enjoy panoramic water views from the gourmet kitchen, featuring wood

  

  Cynthia Brock

  GULF SANDS REALTY, LLC

  (941) 698-6279

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229
• Explore Osprey

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  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Condo for Rent

  293 Hidden Bay Dr Unit 203, Osprey, FL 34229

  RENTED JANUARY TILL MARCH 2026. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second-floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer &

  

  Alba Lange

  WAGNER REALTY

  (941) 207-9375

  293 Hidden Bay Dr Unit 203, Osprey, FL 34229
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  $900,000 Sold Jan 16, 2026

  3957 Waypoint Ave, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,328 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $387/SF
  • 35 Days On Market

  Current Estimated Value $917,771

  Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP

  3957 Waypoint Ave, Osprey, FL 34229
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  Est $850,751 Not Listed For Sale

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229

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

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229

  Last Sold Summary

  • 8% Below List Price
  • $478/SF
  • 0 Days On Market

  Last Sold Price $925,000

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /56

  $699,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 3 Baths
  • 2,630 Sq Ft

  6100 Jessie Harbor Dr Unit 203, Osprey, FL 34229

  BETTER HURRY, LOOK AT THE PRICE! Waterfront living and a true boater’s lifestyle await in this meticulously maintained end-unit residence located in the gated, amenity-rich community of Blackburn Harbor in Osprey. This beautifully upgraded condo offers sweeping Intracoastal water views with Gulf glimpses, abundant natural light, and exceptional privacy within an exclusive boutique building of

  

  Scott Swonger

  HOMESMART

  (941) 304-4466

  6100 Jessie Harbor Dr Unit 203, Osprey, FL 34229
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  /2

  $5,500 per month

  • 3 Beds
  • 2 Baths
  • 2,172 Sq Ft
  • House for Rent

  557 Crane Prairie Way, Osprey, FL 34229

  Welcome to this beautiful fully furnished 3-bed, 2-bath home in the gated community of Willowbend in Osprey. With 2,172 sq ft of bright, open living space, this seasonal rental offers comfort, style, and plenty of room to relax. Enjoy a spacious kitchen, a large primary suite, and a peaceful screened lanai perfect for morning coffee or evening sunsets.The community features a pool, fitness

  

  Craig McCoy

  PREFERRED SHORE LLC

  (941) 392-7290

  557 Crane Prairie Way, Osprey, FL 34229
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  $1,600,000 Sold May 01, 2025

  916 MacEwen Dr, Osprey, FL 34229

  • 5 Beds
  • 7.5 Baths
  • 5,987 Sq Ft
  • Built 1991

  Last Sold Summary

  • 11% Below List Price
  • $267/SF
  • 1 Day On Market

  Current Estimated Value $1,659,872

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  916 MacEwen Dr, Osprey, FL 34229
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  Est $497,599 Not Listed For Sale

  629 Oak Bay Dr, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 1996

  629 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • $268/SF
  • 250 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Toni Zarghami KW COASTAL LIVING III
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  /90

  $1,050,000 Pending

  • 3 Beds
  • 3 Baths
  • 3,297 Sq Ft

  1218 Yacht Harbor Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Attention water lovers... take a look at this home in the highly sought-after community of Southbay Yacht & Racquet Club, where true resort-style living awaits. The community offers an impressive array of amenities, including a marina, a recently remodeled clubhouse, shuffleboard courts, three tennis courts, four pickleball courts, a bocce ball court,

  

  Karie Backman

  KELLER WILLIAMS ON THE WATER S

  (941) 352-2028

  1218 Yacht Harbor Dr, Osprey, FL 34229
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  /238

  $1,635 - $2,925 per month

  Alton Osprey

  1 - 3 Beds

  4000 Destination Dr, Osprey, FL 34229

  Now open for immediate move-ins, discover stunning one-, two-, and three-bedroom apartment homes in Sarasota, FL. With high-end finishes outfitting each residence, offering the perfect blend of comfort and sophistication, coming home will feel like a daily retreat. Our best-in-class amenity spaces allow you the opportunity to live beyond your expectations - from our sleek business center that

  4000 Destination Dr, Osprey, FL 34229
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  $140,000 Sold May 02, 2025

  234 Patterson Ave, Osprey, FL 34229

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft
  • Built 1979

  Last Sold Summary

  • 53% Below List Price
  • $119/SF
  • 9 Days On Market

  Current Estimated Value $198,982

  Last Listing Agent Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  234 Patterson Ave, Osprey, FL 34229
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  Est $610,122 Not Listed For Sale

  593 Crane Prairie Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,340 Sq Ft
  • Built 2005

  593 Crane Prairie Way, Osprey, FL 34229

  Last Sold Summary

  • 1% Below List Price
  • $263/SF
  • 194 Days On Market

  Last Sold Price $615,000

  Last Listing Agent Cynthia Bowers COLDWELL BANKER SARASOTA CENT.
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  $3,890,000

  • 4 Beds
  • 6 Baths
  • 9,081 Sq Ft

  854 MacEwen Dr, Osprey, FL 34229

  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’s light-filled, open design and thoughtful updates make an immediate impression. The main living spaces flow effortlessly from the chef’s kitchen to expansive entertaining areas and out to the

  

  Joe Murphy

  COLDWELL BANKER REALTY

  (941) 394-8350

  854 MacEwen Dr, Osprey, FL 34229
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  $4,500 per month

  • 3 Beds
  • 3.5 Baths
  • 2,115 Sq Ft
  • House for Rent

  3929 Waypoint Ave, Osprey, FL 34229

  ANNUAL RENTAL - Pristine Single family home in the highly sought after community of Bayside in Osprey. The beautiful heated pool home features three bedrooms and three baths as well a private office space. Master bedroom offers an en suite bathroom with dual vanities, walk in shower, oversized walk in closet with built ins. Kitchen is complete with Gas Range, Oversized Island, Quartz Countertops

  Rachel Tritschler RE/MAX ALLIANCE GROUP

  3929 Waypoint Ave, Osprey, FL 34229
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  $265,000 Sold May 15, 2025

  360 Pine Run Dr Unit 360, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,379 Sq Ft
  • Built 1973

  Last Sold Summary

  • 16% Below List Price
  • $192/SF
  • 74 Days On Market

  Current Estimated Value $250,242

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  360 Pine Run Dr Unit 360, Osprey, FL 34229
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  Est $359,505 Not Listed For Sale

  4234 Frontier Ln Unit 101, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 2018

  4234 Frontier Ln Unit 101, Osprey, FL 34229

  Last Sold Summary

  • 18% Below List Price
  • $280/SF
  • 91 Days On Market

  Last Sold Price $440,000

  Last Listing Agent Mark Lyda GENEROUS PROPERTY
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  /55

  $579,000

  • 4 Beds
  • 2 Baths
  • 2,203 Sq Ft

  583 Pine Ranch East Rd, Osprey, FL 34229

  Beautifully updated 4BR/2BA pool home in the sought-after Bay Oaks Estates community of Osprey. This single-story residence's backyard borders the Legacy Trail and includes a private gate for direct trail access. Inside, high ceilings and natural light complement luxury vinyl plank flooring, fresh paint, new doors, baseboards, and fixtures. The kitchen features quartz countertops, marble

  

  William Fortner

  GALLERY PROPERTIES INTERNATIONAL

  (941) 239-7527

  583 Pine Ranch East Rd, Osprey, FL 34229
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  /20

  $1,900 per month

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Condo for Rent

  236 Woodland Dr, Osprey, FL 34229

  Property Id: 310276AVAILABLE MAY 15 to SEP 30, 2026 Light, airy home in Pine Run overlooks established native landscaping. Copious sliding doors, windows & high ceilings. Beautifully updated kitchen offer views to outdoors. Carport + 1 visitor parking space. A nature lovers paradise, this laid-back, quiet & desirable community is close to Casey Key, Blackburn Point Park & Intracoastal

  236 Woodland Dr, Osprey, FL 34229
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  $452,500 Sold Aug 29, 2025

  784 Sarabay Rd, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 1981

  Last Sold Summary

  • 38% Below List Price
  • $287/SF
  • 257 Days On Market

  Current Estimated Value $431,332

  Last Listing Agent Peggy Lewis COLDWELL BANKER SARASOTA CENT.

  784 Sarabay Rd, Osprey, FL 34229
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  /70

  Est $1,056,481 Not Listed For Sale

  3961 Waypoint Ave, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,346 Sq Ft
  • Built 2018

  3961 Waypoint Ave, Osprey, FL 34229

  Last Sold Summary

  • 8% Below List Price
  • $490/SF
  • 213 Days On Market

  Last Sold Price $1,150,000

  Last Listing Agent Lee Brewer RE/MAX
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  $1,800,000

  • 4 Beds
  • 3.5 Baths
  • 4,387 Sq Ft

  401 Walls Way, Osprey, FL 34229

  Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously appointed estate offers a rare opportunity for a premier Sarasota golf course lifestyle. Designed for the discerning enthusiast, the property features panoramic fairway views and western exposure for breathtaking sunsets. The interior is defined by soaring vaulted ceilings, refined crown molding, & finishes

  

  Andrea Stultz

  ENGEL + VOELKERS SARASOTA

  (941) 231-5436

  401 Walls Way, Osprey, FL 34229
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  /31

  $2,400 per month

  • 1 Bed
  • 1 Bath
  • 623 Sq Ft
  • Condo for Rent

  51 MacEwen Dr Unit 12, Osprey, FL 34229

  For Lease at THE OAKS CLUB WINDSOR LODGE. Private sanctuary rarely available for rent at one of Sarasota's most exclusive private country clubs. This lovely sunny Second floor end unit is fully turnkey furnished and ready for MOVE IN. Completely updated one bedroom, resort suite style studio, condominium with sweeping Water Views of the Lakefront of the 18th fairway on the Eagle Course. A

  Patrice Ivan WAGNER REALTY

  51 MacEwen Dr Unit 12, Osprey, FL 34229
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  $875,585 Sold Mar 27, 2025

  280 Hidden Bay Dr Unit 403, Osprey, FL 34229

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

  Last Sold Summary

  • 4% Above List Price
  • $452/SF
  • 13 Days On Market

  Current Estimated Value $812,680

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 403, Osprey, FL 34229
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  /98

  Est $754,475 Not Listed For Sale

  250 Hidden Bay Dr Unit A504, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,168 Sq Ft
  • Built 2017

  250 Hidden Bay Dr Unit A504, Osprey, FL 34229

  Last Sold Summary

  • 13% Below List Price
  • $399/SF
  • 38 Days On Market

  Last Sold Price $865,000

  Last Listing Agent Frank Koziel, P.A. COLDWELL BANKER REALTY
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  $850,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,869 Sq Ft

  1486 Landview Ln, Osprey, FL 34229

  Experience refined waterfront living in Southbay, one of the area’s most coveted boating communities. This impeccably maintained three-bedroom pool residence offers a thoughtful, split-bedroom design that balances privacy with seamless flow—ideal for both relaxed everyday living and sophisticated entertaining. A comprehensive renovation in 2017 elevated the home with cohesive flooring throughout,

  

  Barbara Teyssier

  EXP REALTY LLC

  (941) 208-4807

  1486 Landview Ln, Osprey, FL 34229
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  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,371 Sq Ft
  • House for Rent

  253 Glenwood Ave, Osprey, FL 34229

  Welcome to your new oasis in Osprey! This charming 3-bedroom, 2-bathroom house offers a perfect blend of comfort and convenience, making it an ideal place to call home. With a spacious 1,371 square feet, there's plenty of room for you to spread out and enjoy life.Step inside to discover a bright and inviting living space, complete with modern amenities that make daily living a breeze. The

  253 Glenwood Ave, Osprey, FL 34229
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  $865,000 Sold Feb 10, 2026

  38 W Bay St, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,124 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Below List Price
  • $407/SF
  • 107 Days On Market

  Current Estimated Value $872,101

  Last Listing Agent Mitch Helmuth HARRY ROBBINS ASSOC INC

  38 W Bay St, Osprey, FL 34229
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  Est $1,051,980 Not Listed For Sale

  3973 Waypoint Ave, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,377 Sq Ft
  • Built 2018

  3973 Waypoint Ave, Osprey, FL 34229

  Last Sold Summary

  • $442/SF
  • 84 Days On Market

  Last Sold Price $1,050,000

  Last Listing Agent Carlo Costantini DAVE JONES REALTY, LLC
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  /41

  $325,000

  • 2 Beds
  • 2 Baths
  • 1,165 Sq Ft

  1801 Highland Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and

  

  Kimberly Werla

  RE/MAX ALLIANCE GROUP

  (941) 757-8192

  1801 Highland Rd, Osprey, FL 34229
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  $2,500 per month

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

  80 Navigation Cir, Osprey, FL 34229

  Turnkey fully furnished newer built 3 bedroom 2 bathroom one car garage townhouse on the second floor. Hurricane windows, gated community, with community pool, club house and gym room. 15-20 minutes to Siesta Key and about 10-15 to Nokomis Beach, Legacy Trail at the end of the street, Dogpark across the street. Walking distance to 4-5 Restaurants. Walmart across the street 3 Publixes and a Target

  Krisztian Kecskes M&M PROPERTY MANAGEMENT GROUP

  80 Navigation Cir, Osprey, FL 34229
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  $75,000 Sold Dec 12, 2025

  570 Blackburn Point Rd Unit 2, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 5% Below List Price
  • 17 Days On Market

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 2, Osprey, FL 34229
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  Est $604,248 Not Listed For Sale

  4421 Conchfish Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,133 Sq Ft
  • Built 2017

  4421 Conchfish Ln, Osprey, FL 34229

  Last Sold Summary

  • 1% Below List Price
  • $286/SF
  • 38 Days On Market

  Last Sold Price $610,000

  Last Listing Agent Rory McDonald PREFERRED SHORE LLC
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  $2,850,000

  • Land
  • 0.39 Acre
  • $7,307,692 per Acre

  141 N Casey Key Rd, Osprey, FL 34229

  CASEY KEY ISLAND OPPORTUNITY – Bring your preferred builder and create the coastal retreat of your dreams on one of Sarasota County’s most treasured barrier islands. Perfectly positioned on the coveted north end of Casey Key, this exceptional property offers over 100 feet of direct Gulf frontage and sweeping, unobstructed sunset views across shimmering turquoise waters. Your blank canvas awaits –

  

  Julie Larson

  WHITE SANDS REALTY GROUP FL

  (941) 263-0115

  141 N Casey Key Rd, Osprey, FL 34229
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  $1,850 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • House for Rent

  455 Pennsylvania Ave, Osprey, FL 34229

  Fully Furnished 2BR/1BA Turnkey Home in Osprey, FLUnique, peaceful property with native wildflower garden, beach gear, and old-Florida charm. Located in the quiet fishing village of Osprey, this FULLY FURNISHED home includes:•Upgraded kitchen with stainless steel appliances, granite counters, and all essentials•New washer/dryer•Enclosed lanai•High-speed WiFi, water, sewer,

  455 Pennsylvania Ave, Osprey, FL 34229
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  $1,050,000 Sold Apr 16, 2025

  247 Keel Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,871 Sq Ft
  • Built 1979

  Last Sold Summary

  • 9% Below List Price
  • $366/SF
  • 70 Days On Market

  Current Estimated Value $1,009,239

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  247 Keel Way, Osprey, FL 34229
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  Est $736,333 Not Listed For Sale

  148 Osprey Point Dr, Osprey, FL 34229

  148 Osprey Point Dr, Osprey, FL 34229

  Last Sold Summary

  • 8% Below List Price
  • 375 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN
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  $1,695,000

  • 3 Beds
  • 3.5 Baths
  • 3,208 Sq Ft

  480 Oriskany Ct, Osprey, FL 34229

  Tucked away on a quiet street within the prestigious Oaks Club, this elegant residence overlooks the fairway of the Heron 14. This is a rare opportunity to find a home on a premium golf course lot and have the additional privacy of a preserve view across the street. Designed by Toll Brothers, this meticulous 3 bedroom; plus den home offers gracious, entertaining and comfortable everyday living. A

  

  Susan Pelton

  MICHAEL SAUNDERS & COMPANY

  (941) 491-3516

  480 Oriskany Ct, Osprey, FL 34229
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  $4,800 per month

  • 4 Beds
  • 3 Baths
  • 2,290 Sq Ft
  • House for Rent

  956 Scherer Way, Osprey, FL 34229

  Stunning 4-bedroom, fully furnished pool home backing directly to the tropical preserve of Oscar Scherer State Park in the highly desirable Woodlands at Rivendell. Enjoy privacy, serene views, and resort-style living within a beautifully maintained community featuring 400+ acres of lakes, walking trails, playground, and heated community pool. Prime location — walking distance to Pine View School

  Chantelle Edalgo EXIT KING REALTY

  956 Scherer Way, Osprey, FL 34229
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  $1,850,000 Sold Jan 22, 2026

  453 E MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,191 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Below List Price
  • $441/SF
  • 19 Days On Market

  Current Estimated Value $1,843,181

  Last Listing Agent William Kelly THE REAL ESTATE STORE

  453 E MacEwen Dr, Osprey, FL 34229
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  Est $1,131,674 Not Listed For Sale

  3932 Waypoint Ave, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,416 Sq Ft
  • Built 2017

  3932 Waypoint Ave, Osprey, FL 34229

  Last Sold Summary

  • 17% Below List Price
  • $566/SF
  • 11 Days On Market

  Last Sold Price $1,367,500

  Last Listing Agent Larry Brzostek RE/MAX

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