Osprey, FL Homes

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  /69

  $749,000

  • 3 Beds
  • 3 Baths
  • 2,267 Sq Ft

  471 Park Trace Blvd, Osprey, FL 34229

  Welcome to your dream home! This stunning, custom-built 3 bedroom, 3 bathroom residence perfectly blends luxury, comfort, and location for the ideal Florida lifestyle. This home is nestled in a highly sought-after neighborhood offering peace, privacy, and a vibrant community feel with low HOA fees. It is situated on an over-sized corner lot, with exceptional lake-views, and just moments from

  Bill Cantrell FLORIDA HOME TEAM LLC

  471 Park Trace Blvd, Osprey, FL 34229
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  /20

  $2,747 per month

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft
  • Condo for Rent

  8 Bay Acres Ave Unit ID1228251P, Osprey, FL 34229

  Relax in this stylish 2-bedroom, 2-bathroom retreat just 5 minutes from Nokomis Beach. Feel at home with a private lanai, fast Wi-Fi, a full kitchen, and a Smart TV with Netflix. Perfect for couples, families, or mid-term stays, this apartment is close to Siesta Key, Venice, and St. Armands, comfortably sleeping up to 6 people.Welcome to your Florida retreat, a centrally located 2-bedroom,

  8 Bay Acres Ave Unit ID1228251P, Osprey, FL 34229
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  /2

  $766,000 Sold Aug 08, 2025

  • 2,463 Sq Ft
  • $311/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  127 Park Trace Blvd, Osprey, FL 34229

  Absolutely Spectacular Lake-View Home in Osprey - with New ROOF and Upgrades throughout is priced to sell!This property boasts over $160,000 in enhancements, including a custom-designed luxury bath, bespoke mastercloset, renovated kitchen, porcelain flooring, remote-controlled blinds, plantation shutters, upgraded laundryfacilities, built-in outdoor grill, refinished pool w/new

  Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  127 Park Trace Blvd, Osprey, FL 34229
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  /63

  Est $990,757 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,115 Sq Ft

  3929 Waypoint Ave, Osprey, FL 34229

  3929 Waypoint Ave, Osprey, FL 34229
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  /68

  $1,970,000

  • 4 Beds
  • 4 Baths
  • 3,286 Sq Ft

  140 Sugar Mill Dr, Osprey, FL 34229

  **BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE ESTATE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood. Featuring 4 BEDROOMS (2 En Suite) and 4 FULL BATHS, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown Moldings and refined details throughout is ideal for entertaining both inside and out! The Impressive

  Mark Lyda GENEROUS PROPERTY

  140 Sugar Mill Dr, Osprey, FL 34229
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  /38

  $6,000 per month

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft
  • Condo for Rent

  409 N Point Rd Unit 802, Osprey, FL 34229

  **TURNKEY FURNISHED, PENTHOUSE Condo Unit has been FULLY RENOVATED** This 8TH FLOOR, Light and Bright, 3-BEDROOM plus 3 FULL BATH dwelling with screened balcony is available beginning in September, 2025. The 2055sf floorplan is tastefully furnished and offers superb views of the Intracoastal Waterway and Gulf. This unit was fully renovated in 2023 with updated oak hardwood flooring, new kitchen

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 802, Osprey, FL 34229
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  /2

  $975,000 Sold Aug 08, 2025

  • 2,344 Sq Ft
  • $416/SF
  • 161 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2016

  3904 Waypoint Ave, Osprey, FL 34229

  This stunning Taylor Morrison Lazio floor plan residence offers an exceptional blend of luxury and tranquility in a desirable West of Trail gated bayfront community. With breathtaking views of the sparkling lake and direct access to the bay, residents can enjoy picturesque sunsets and serenity of daily wildlife sightings. Newer sparkling pool and spa surrounded in pavers. The home features a

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3904 Waypoint Ave, Osprey, FL 34229
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  /67

  Est $560,339 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,890 Sq Ft

  52 Bishops Court Rd Unit 113, Osprey, FL 34229

  52 Bishops Court Rd Unit 113, Osprey, FL 34229
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  /68

  $998,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 3,438 Sq Ft

  766 Shadow Bay Way, Osprey, FL 34229

  Nestled on a quiet street in the highly sought-after Rivendell community, this former Arthur Rutenberg model home features 4 bedrooms, 3 full baths, a den, and 2 versatile flex rooms, offering tranquil views of the pond and surrounding preserve. Framed by lush landscaping, the property features an oversized pool with a generously sized spa and ambient lighting, perfect for evening

  Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

  766 Shadow Bay Way, Osprey, FL 34229
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  /2

  $2,749 per month

  • 3 Beds
  • 2 Baths
  • 1,462 Sq Ft
  • House for Rent

  413 Glenwood Ave, Osprey, FL 34229

  Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,462 square feet, this well-maintained home offers a high standard of

  413 Glenwood Ave, Osprey, FL 34229
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  /2

  $747,850 Sold Aug 08, 2025

  • 2,945 Sq Ft
  • $254/SF
  • 128 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1975

  424 Cezanne Dr, Osprey, FL 34229

  Welcome to your tropical oasis in ideally located, neighbor friendly Sorrento Shores! This spacious two-story, 4-bedroom, 4- bathroom pool home with oversized 3-car garage blends comfort, style, and functionality just minutes from Nokomis Beach near the confluence of South Creek and the Intercoastal Waterway. Located in an X flood zone (no flood insurance required), no CDD fees, and optional HOA,

  Christine Pope MICHAEL SAUNDERS & COMPANY

  424 Cezanne Dr, Osprey, FL 34229
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  /2

  Est $409,130 Not Listed For Sale

  • 2 Beds

  19 Westview Dr, Osprey, FL 34229

  19 Westview Dr, Osprey, FL 34229
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  /32

  $1,450,000

  • 5 Beds
  • 3.5 Baths
  • 3,481 Sq Ft

  296 Pine Ranch Trail, Osprey, FL 34229

  **THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of

  Deborah Frederick ASHTON LAKES REALTY INC

  296 Pine Ranch Trail, Osprey, FL 34229
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  /53

  $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 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 doors, and powder room in an

  Henry Rossi RENT SARASOTA

  260 Hidden Bay Dr Unit B-504, Osprey, FL 34229
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  /2

  $962,500 Sold Aug 07, 2025

  • 3,321 Sq Ft
  • $290/SF
  • 115 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2002

  742 Shadow Bay Way, Osprey, FL 34229

  Welcome to Luxury Living in Rivendell! Nestled on a premium, private lot with serene lake and preserve views, this impeccably maintained, custom-built Arthur Rutenberg home offers elegance, comfort, and thoughtful design in every detail. Boasting 3,321 sq ft of refined living space, this residence features an open split floor plan, soaring ceilings, and abundant natural light throughout. The

  Reeny Kaney RE/MAX ALLIANCE GROUP

  742 Shadow Bay Way, Osprey, FL 34229
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  /2

  Est $45,148 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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  /38

  $815,000

  • 3 Beds
  • 2 Baths
  • 2,443 Sq Ft

  901 Reflection Way, Osprey, FL 34229

  LOCATION! LOCATION! Tucked away on a quiet cul-de-sac and resting on a corner lot, this METICULOUSLY MAINTAINED, Custom-built, JOHN CANNON home in exclusive North Creek Estates offers the perfect blend of privacy, luxury, and convenience. With a NEW ROOF (2020), low HOA fees, and 2,443 sq. ft. of thoughtfully designed living space, this 3-Bedroom + Office/Den, 2-Bath residence is MOVE-IN READY

  Mark Lyda GENEROUS PROPERTY

  901 Reflection Way, 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 15, 2026 / $100 discount for term of 2 or more months: 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

  236 Woodland Dr, Osprey, FL 34229
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  /2

  $1,015,000 Sold Aug 01, 2025

  • 3,912 Sq Ft
  • $259/SF
  • 11 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2002

  678 Clear Creek Dr, Osprey, FL 34229

  Looking for quality craftsmanship??? This exceptional home was built by US Homes, with a unique distinction — the original owner was the president of US Homes at the time of construction, personally overseeing every detail to ensure top-tier quality and craftsmanship throughout. This exquisitely remodeled 5-bedroom, 3-bath estate, nestled in one of Sarasota County's most desirable and serene

  Dena Olson EXIT KING REALTY

  678 Clear Creek Dr, Osprey, FL 34229
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  /4

  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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  /62

  $965,000

  • 2 Beds
  • 2 Baths
  • 2,310 Sq Ft

  13 Bayhead Ln, Osprey, FL 34229

  **IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered

  Mark Lyda GENEROUS PROPERTY

  13 Bayhead Ln, Osprey, FL 34229
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  /2

  $750 per month

  • House for Rent

  570 Blackburn Point Rd Unit 25, Osprey, FL 34229

  Welcome to The Dry Slips at Osprey Harbor Village. On-site you'll enjoy access to the marina store with food, drinks, ice, and bait. Conveniently available are pump out, ethanol-free fuel, work racks, and fish cleaning stations as well. This indoor slip is high and dry hurricane-rated and secured. Unit 25 of Longboat Row is 14.6' tall, 10.5' wide and 28' long on the bottom row for easy access.

  EJ Stukenborg KELLER WILLIAMS ON THE WATER S

  570 Blackburn Point Rd Unit 25, Osprey, FL 34229
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  /2

  $430,000 Sold Aug 01, 2025

  • 1,411 Sq Ft
  • $305/SF
  • 244 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1967

  117 Villa Dr Unit 117, Osprey, FL 34229

  Let’s Go Fishing! Best Price in Sarasota County – Waterfront Villa with PRIVATE DOCK! Tenant in place! Welcome to your dream Florida lifestyle in Osprey, FL! This charming 2-bedroom waterfront villa is your perfect escape into the best of coastal living. Located in the peaceful, pet-friendly community of Sorrento Shores, this home offers direct access to the Gulf of Mexico, making it the

  Bill Garrison RE/MAX PALM

  117 Villa Dr Unit 117, Osprey, FL 34229
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  /44

  Est $1,136,146 Not Listed For Sale

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

  3925 Waypoint Ave, Osprey, FL 34229

  3925 Waypoint Ave, Osprey, FL 34229
• 

  

  /79

  $1,450,000

  • 4 Beds
  • 3.5 Baths
  • 3,464 Sq Ft

  402 Walls Way, Osprey, FL 34229

  Welcome to timeless elegance and modern comfort in The Oaks Clubside. This stunning 4-bedroom plus den/office, 3.5-bath home, built in 2014 by Todd Johnson Homes, blends country modern style with refined sophistication. Situated on an oversized .64-acre corner lot, this courtyard-style residence is designed for effortless Florida living. Step through grand double wood doors into an inviting space

  Steve Abbe COLDWELL BANKER REALTY

  402 Walls Way, Osprey, FL 34229
• 

  

  /20

  $2,350 per month

  • 3 Beds
  • 2.5 Baths
  • 1,655 Sq Ft
  • Condo for Rent

  205 Navigation Cir Unit 205, Osprey, FL 34229

  town home style condo at Bay Street, with beautiful lakefront view. Enjoy coastal breezes & the Florida lifestyle in maintenance free community. open design concept with great room, kitchen & dinning on the 1st floor, Cherry spice cabinets, stainless appliances, granite counter tops, with a private covered entry porch & 2 separate garages. Luxury waterproof floor on the second floor. Master suite

  Qi Wang HAUZS INC

  205 Navigation Cir Unit 205, Osprey, FL 34229
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  /2

  $645,000 Sold Jul 31, 2025

  • 2,223 Sq Ft
  • $290/SF
  • 9 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2003

  673 Crane Prairie Way, Osprey, FL 34229

  Enjoy spectacular sunsets over a sweeping lake view the minute you walk through the door. This lovely Savannah model built by Lee Wetherington boasts three spacious bedrooms, three baths plus an office/flex room, making it the property for you and your family and guests. The primary suite has a sitting area that opens to the pool and lanai, two walk-in closets, and a large bath with double sinks,

  Laura Harris, PA PREMIER SOTHEBYS INTL REALTY

  673 Crane Prairie Way, Osprey, FL 34229
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  /65

  Est $1,130,080 Not Listed For Sale

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

  3937 Waypoint Ave, Osprey, FL 34229

  3937 Waypoint Ave, Osprey, FL 34229
• 

  

  /78

  $1,095,000

  • 5 Beds
  • 4 Baths
  • 3,938 Sq Ft

  820 Placid Lake Dr, Osprey, FL 34229

  Discover this expansive 5-bedroom, 4-bathroom home with an oversized bonus room and 3,938 sq. ft. of living space, perfectly situated on a 10,548 sq. ft. lakefront lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2024), new zoned HVAC units (2022), a new pool heater (2024), a new water heater (2025) with a 25-year whole-home water conditioner, fresh

  Ali Marks LOYD ROBBINS & CO. LLC

  820 Placid Lake Dr, Osprey, FL 34229
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  /49

  $9,000 per month

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft
  • House for Rent

  18 N Casey Key Rd, Osprey, FL 34229

  Beautifully remodeled in 2012, this bayfront residence combines elegance, functionality and an enviable location. The living room, kitchen and family room are great places to gather, and the split floor plan provides room for all, privacy to retreat with a good book or work from home options. The classic coastal style provides a view of the bay and intracoastal waterway from the primary bedroom.

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  18 N Casey Key Rd, Osprey, FL 34229
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  /2

  $625,000 Sold Jul 26, 2025

  • 2,256 Sq Ft
  • $277/SF
  • 1 Day On Market

  • 4 Beds
  • 3 Baths
  • Built 2001

  695 Rivendell Blvd, Osprey, FL 34229

  Welcome to 695 Rivendell Boulevard in Osprey, Florida – a beautifully maintained home offering comfort, style, and an unbeatable location. Just minutes from the Gulf Coast’s renowned beaches, shopping, and dining, this property features a host of recent upgrades designed for modern living. Hurricane protection includes a new garage door (2018) and Jansen electric roll-down and Bahama shutters

  Dan Henson DALTON WADE INC

  695 Rivendell Blvd, Osprey, FL 34229
• 

  

  /22

  Est $294,355 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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  /61

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 2,545 Sq Ft

  3603 N Point Rd Unit 702, Osprey, FL 34229

  **MAGNIFICENT VIEW from this 7th FLOOR, PENTHOUSE CONDO** Offering 3 EN SUITE BEDROOMS, 3 FULL BATHS and a treasured PRIVATE 2-CAR GARAGE! Located behind the gates of the highly sought after Oaks-Preserve, country club neighborhood in the Newest Meridian Condo Tower (Built in 2007 and featuring Hurricane Impact rated Windows and Sliding Doors). As you emerge from your private elevator foyer

  Mark Lyda GENEROUS PROPERTY

  3603 N Point Rd Unit 702, Osprey, FL 34229
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  /44

  $6,500 per month

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

  521 Habitat Blvd, Osprey, FL 34229

  Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 90 Day minimum stay in Peak Season at $10,500/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 retreat

  Dave Holt PMI SARASOTA

  521 Habitat Blvd, Osprey, FL 34229
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  /2

  $150,000 Sold Jul 25, 2025

  • 865 Sq Ft
  • $173/SF
  • 49 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 1979

  107 Woodland Place Unit 107, Osprey, FL 34229

  This ground level condominium comes with a deeded carport and two storage closets. Enjoy a deck off the kitchen and a screened lanai that runs the length of the unit and is accessible from both the living area and bedroom. Both the half bath and primary bedroom suite have been recently remodeled with new flooring and fixtures. Washer and dryer hook-ups are located in an interior closet, so no

  Carla Rayman Kidd COLDWELL BANKER REALTY

  107 Woodland Place Unit 107, Osprey, FL 34229
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  /40

  Est $309,420 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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  /80

  $2,995,000

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

  662 Fernwalk Ln, Osprey, FL 34229

  **FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situated on a SERENE, INTERIOR, CUL-DE-SAC lot with NO FLOOD concern (Zone “X”) behind the Secure Gates of the highly sought after Bayside neighborhood within The Oaks Country Club community, just steps from Little Sarasota Bay. An Expansive Floorplan entails 4-BEDs plus 4-FULL BATHS while a full list of EXCEPTIONAL FEATURES is

  Mark Lyda GENEROUS PROPERTY

  662 Fernwalk Ln, Osprey, FL 34229
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  /39

  $4,200 per month

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Condo for Rent

  280 Hidden Bay Dr Unit 302, Osprey, FL 34229

  NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood

  Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

  280 Hidden Bay Dr Unit 302, Osprey, FL 34229
• 

  /2

  $325,000 Sold Jul 24, 2025

  • 1,528 Sq Ft
  • $213/SF
  • 90 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2016

  4236 Expedition Way Unit 106, Osprey, FL 34229

  FABULOUS, MODERN, FURNISHED 3 BEDROOM/2 BATHROOM/1 CAR GARAGE CONDO in desirable Bay Street Village. This second story (walk-up) is impressive! The OPEN CONCEPT offers a spacious feel, yet the split bedroom design allows for privacy when your guests are visiting. Quality features include a designer kitchen with cherry cabinets, crown molding, granite countertops, IMPACT WINDOWS, tile roof, paver

  Susan Honsberger RE/MAX ALLIANCE GROUP

  4236 Expedition Way Unit 106, Osprey, FL 34229
• 

  

  /34

  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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