Osprey, FL Homes

• 

  

  

  /43

  $995,000

  • 3 Beds
  • 2 Baths
  • 2,188 Sq Ft

  599 Pine Ranch Rd E, Osprey, FL 34229

  **EXQUISITELY UPDATED, TURNKEY FURNISHED, POOL HOME** in Popular BAY OAKS ESTATES. This Stunning Residence is MOVE-IN READY (just Bring Your Suitcase!) and features a LIGHT and BRIGHT, OPEN FLOORPLAN including 3 BEDS plus STUDY/DEN and 2 FULL BATHS. The Gourmet Kitchen boasts a modern, European design with premium appliance package and counter sitting area while the primary bedroom suite offers

  Mark Lyda GENEROUS PROPERTY

  599 Pine Ranch Rd E, Osprey, FL 34229
• 

  

  

  /36

  $7,200 per month

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

  101 Woodland Place, Osprey, FL 34229

  Now AVAILABLE FOR LEASE WINTER SEASON 2026 at PINE RUN Condominiums in Osprey, Florida! 3BR/2.5BA Location! Location! West of the Trail, Pine Run is a waterfront tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of light and color with vaulted ceiling in the main Great Room. Custom designed Kitchen is

  Patrice Ivan WAGNER REALTY

  101 Woodland Place, Osprey, FL 34229
• 

  

  /2

  $247,000 Sold Aug 14, 2025

  • 1,325 Sq Ft
  • $186/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  121 Woodland Place Unit 121, Osprey, FL 34229

  Fabulous location for this FULLY FURNISHED, TURNKEY, two bedroom second floor condo in the Pine Run neighborhood. If you've been thinking of becoming a snowbird, you couldn't ask for more than this! Close to the iconic Casey Key Fish House Tiki Bar, the inter coastal, shopping, restaurants, main roads, and several beaches!! Located between Venice and Sarasota, you can easily enjoy both

  Pat Williams PAT WILLIAMS REALTY, LLC

  121 Woodland Place Unit 121, Osprey, FL 34229
• 

  

  

  /48

  Est $361,074 Not Listed For Sale

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

  123 Revolution Way Unit 101, Osprey, FL 34229

  123 Revolution Way Unit 101, Osprey, FL 34229
• 

  

  

  /62

  $925,000

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft

  385 N Point Rd Unit 404, Osprey, FL 34229

  **STUNNINGLY UPDATED CONDO with Breathtaking Water & Preserve Views that rival those of higher floors!** This LARGE, CORNER UNIT of nearly 2800sf features 3-Beds & 3 Full Baths PLUS Study/Den (or possible 4th Bedroom with Walk-In Closet) and 2 side-by-side Covered Parking Spaces near elevator, Etc. and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 404, Osprey, FL 34229
• 

  

  /42

  $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
• 

  /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
• 

  

  /61

  Est $368,590 Not Listed For Sale

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

  4185 Frontier Ln Unit 102, Osprey, FL 34229

  4185 Frontier Ln Unit 102, Osprey, FL 34229
• 

  

  /62

  $1,499,500

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft

  385 N Point Rd Unit 701, Osprey, FL 34229

  **INCOMPARABLE VIEW! 7th FLOOR, CORNER CONDO UNIT WITH UNOBSTRUCTED SOUTH AND WEST PANORAMA. This Spacious unit of nearly 2600sf features 3-Beds PLUS Study/Den, 3 Full Baths and includes a PRIVATE 2-CAR GARAGE. Located behind the Secure Gates of the Oaks-Preserve, Country Club neighborhood, this Light and Bright, Sought-after unit boasts a VIEW which you MUST EXPERIENCE TO BELIEVE from its

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 701, Osprey, FL 34229
• 

  

  /74

  $7,500 per month

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

  14041 Bellagio Way Unit 316, Osprey, FL 34229

  NOW AVAILABLE DEC 2025 $6,500 AND JAN-APRIL 2026 $7,500! 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 entering, you

  Chrissie Cummings JENNETTE PROPERTIES INC

  14041 Bellagio Way Unit 316, Osprey, FL 34229
• 

  /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
• 

  

  /59

  Est $353,769 Not Listed For Sale

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

  99 Explorer Dr Unit 102, Osprey, FL 34229

  99 Explorer Dr Unit 102, Osprey, FL 34229
• 

  

  /73

  $2,550,000

  • 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
• 

  

  /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
• 

  /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
• 

  

  /42

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 673 Sq Ft

  36 Siesta Cir W, Osprey, FL 34229

  36 Siesta Cir W, Osprey, FL 34229
• 

  

  /69

  $699,000

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

  471 Park Trace Blvd, Osprey, FL 34229

  SIGNIFICANT PRICE IMPROVEMENT!! Welcome to your dream home! This stunning, custom-built 4 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

  Bill Cantrell FLORIDA HOME TEAM LLC

  471 Park Trace Blvd, Osprey, FL 34229
• 

  

  /21

  $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
• 

  /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
• 

  

  /4

  Est $29,766 Not Listed For Sale

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 28, Osprey, FL 34229

  570 Blackburn Point Rd Unit 28, Osprey, FL 34229
• 

  

  /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
• 

  /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 Dominiczak EXIT KING REALTY

  678 Clear Creek Dr, Osprey, FL 34229
• 

  

  /68

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,247 Sq Ft

  273 Sun Air Cir, Osprey, FL 34229

  273 Sun Air Cir, Osprey, FL 34229
• 

  

  /74

  $1,300,000

  • 4 Beds
  • 3 Baths
  • 2,474 Sq Ft

  700 Faith Ave, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Upon passing the gated pillars of the winding driveway you come upon a hidden treasure. 2.5 Acres of beauty tucked away just off Tamiami and Bay in Osprey. This property backs up to the renowned Pine View school grades 2-12. One of the finest schools in the state and country. The peace and tranquility of the outdoor space is highlighted by a resort

  steve mularky LACEY REALTY INC

  700 Faith Ave, Osprey, FL 34229
• 

  /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
• 

  

  /24

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft

  338 Tropic Dr, Osprey, FL 34229

  338 Tropic Dr, Osprey, FL 34229
• 

  

  /75

  $2,300,000

  • 4 Beds
  • 5.5 Baths
  • 4,346 Sq Ft

  538 Dove Pointe, Osprey, FL 34229

  **ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home

  Mark Lyda GENEROUS PROPERTY

  538 Dove Pointe, Osprey, FL 34229
• 

  /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
• 

  

  /79

  Est $638,316 Not Listed For Sale

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

  250 Hidden Bay Dr Unit A203, Osprey, FL 34229

  250 Hidden Bay Dr Unit A203, Osprey, FL 34229
• 

  

  /78

  $1,899,000

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

  453 E MacEwen Dr, Osprey, FL 34229

  Set an appointment to experience this thoughtfully designed Arthur Rutenberg home, where craftsmanship and details are truly on display. Upon entering through the double door entrance, the quality and attention to detail are immediately evident. Situated on a 1/2 acre + "premium" golf course lot strategically positioned on the Heron Course (hole 5). This residence blends timeless design with

  William Kelly THE REAL ESTATE STORE

  453 E MacEwen Dr, Osprey, FL 34229
• 

  /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
• 

  

  /13

  Est $820,000 Not Listed For Sale

  0 Cezanne Dr Unit A4556644, Osprey, FL 34229

  0 Cezanne Dr Unit A4556644, Osprey, FL 34229
• 

  

  /91

  $2,195,000

  • 3 Beds
  • 3 Baths
  • 3,681 Sq Ft

  600 Eagle Watch Ln, Osprey, FL 34229

  One or more photo(s) has been virtually staged. **BRILLIANTLY UPDATED, MOVE-IN READY, GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** offers an Ideal Southern-Exposure and View across the 3rd Fairway of the Interior, HERON GOLF COURSE. Situated on an Oversized 0.71 Acre Lot with Circular Driveway and manicured landscape, this Extensively Renovated Home offers 3

  Mark Lyda GENEROUS PROPERTY

  600 Eagle Watch Ln, Osprey, FL 34229
• 

  /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
• 

  

  /29

  Est $505,370 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  313 Sorrento Dr, Osprey, FL 34229

  313 Sorrento Dr, Osprey, FL 34229
• 

  

  /63

  $599,000

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  232 Hidden Bay Dr Unit 504, Osprey, FL 34229

  This condominium has it all! Fantastic water views along the Intracoastal. Amazing sunsets from the large balcony. A private two-car garage. Three bedrooms, three full baths and 2,000 square feet of living area. The building has a new roof, the elevator was just replaced, and yet the condo dues were just reduced by $500 a quarter! The spacious screened-in balcony overlooks greenery and the

  Per Nordstrom PREMIER SOTHEBY'S INTERNATIONAL REALTY

  232 Hidden Bay Dr Unit 504, 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
• 

  

  /35

  Est $356,366 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft

  4242 Frontier Ln Unit 106, Osprey, FL 34229

  4242 Frontier Ln Unit 106, Osprey, FL 34229
• 

  

  /79

  $1,325,000

  • 3 Beds
  • 2 Baths
  • 2,850 Sq Ft

  17 Bayhead Ln, Osprey, FL 34229

  Welcome to an exquisitely revitalized estate set amidst a stunning landscape that is sure to impress. Located “West of Trail” in The Oaks Preserve, you will experience an unparalleled country club lifestyle on Florida’s Gulf Coast. As you step through the grand front entry, you are welcomed by a blend of contemporary sophistication and modern luxury, transforming this residence into a true

  Ashley LeRoy CORNERSTONE R.E OF SW FL

  17 Bayhead Ln, Osprey, FL 34229
• 

  /2

  $35,000 Sold Jul 22, 2025

  • 62 Days On Market

  • Built 2006

  570 Blackburn Point Rd Unit 17, Osprey, FL 34229

  Dry boat slip for sale at Osprey Harbor Village—hurricane-protected dry storage with top-tier amenities! This rarely available top-level slip means no boats dripping on yours and offers hassle-free storage in one of Sarasota County’s most convenient locations. Keep your boat safe from Florida’s unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 17, Osprey, FL 34229

Showing Results 121 - 160, Page 4 of 18