Sarasota, FL Homes

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  /93

  $750,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,799 Sq Ft

  14041 Bellagio Way Unit 414, Osprey, FL 34229

  Luxury waterfront penthouse with deep water marina access. Discover Osprey Harbor Village, an exclusive gated condo community of only 53 residences perfectly positioned along Florida’s sparkling Intracoastal Waterway. This stunning 3 bedroom, 2 bath penthouse offers nearly 2,000 square feet of thoughtfully designed living space plus a generous 290 square foot tiled terrace with expansive views of

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 297-4970

  14041 Bellagio Way Unit 414, Osprey, FL 34229
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  Explore Osprey

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  /48

  $3,950 per month

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

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

  Enjoy luxury waterfront living in this beautifully updated 6th-floor condo at Blackburn Harbor Residences on the West side of Tamiami Trail, overlooking the Blackburn bay. This 2-bedroom, 2-bath unit includes a den/flex room and offers panoramic water views from the main rooms. The fully remodeled kitchen features quartz countertops, stainless steel appliances, and two refrigerators—perfect for

  

  Jeremy Myers

  COMPASS PROPERTY MANAGEMENT LLC

  (941) 770-3963

  5100 Jessie Harbor Dr Unit 602, 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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  /39

  Est $394,065 Not Listed For Sale

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

  4234 Frontier Ln Unit 101, Osprey, FL 34229

  4234 Frontier Ln Unit 101, Osprey, FL 34229
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  /76

  $1,990,000

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

  600 Eagle Watch Ln, Osprey, FL 34229

  Located on one of the most desirable streets in The Oaks Clubside, this completely renovated pool home sits on a generous 0.71-acre lot with wide views of the third hole of the Heron Golf Course. Nearly every aspect of the property has been updated—new roof, impact-rated windows and doors, flooring, trim, countertops, appliances, resurfaced pool and spa, new pool cage, and a resurfaced

  

  Joe Murphy

  COLDWELL BANKER REALTY

  (941) 274-4697

  600 Eagle Watch Ln, Osprey, FL 34229
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  /40

  $7,500 per month

  • 5 Beds
  • 4.5 Baths
  • 3,981 Sq Ft
  • House for Rent

  1216 Flying Bridge Ln, Osprey, FL 34229

  DO YOU WANT COMFORT AND LUXURY WHILE YOU LOOK AROUND WATERFRONT ? JUMP ON THIS LUXURY TURNKEY RENTAL. A ROOM FOR EVERY HUMAN OR FURRY FRIEND. HEATED POOL. PREMIUM CHEFS KITCHEN, PREMIUM FLOORPLAN, AND PREMIUM NEIGHBORHOOD. FLY THROUGH AVAILABLE. CALL FOR MORE INFO. MINIMUM 3 MONTH RENTAL MAY- OCT 2025 , ONLY.

  

  Meredith Van Vaals

  COLDWELL BANKER REALTY

  (941) 207-3297

  1216 Flying Bridge Ln, 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 PLATINUM

  117 Villa Dr Unit 117, Osprey, FL 34229
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  /70

  Est $1,119,784 Not Listed For Sale

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

  3961 Waypoint Ave, Osprey, FL 34229

  3961 Waypoint Ave, Osprey, FL 34229
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  /88

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 3,379 Sq Ft

  201 Eaglenook Way, Osprey, FL 34229

  Nestled in the exclusive Pine Ranch community of Osprey, Florida, this 4-bedroom, 3-bath estate offers a rare opportunity for those seeking privacy, tranquility, and a healthier way of living. Situated on just over two acres of lush, tree-canopied land, this meticulously maintained home is designed for comfort, sustainability, and connection to nature. From the moment you enter the long private

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 757-8209

  201 Eaglenook Way, Osprey, FL 34229
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  /283

  $2,025 - $3,495 per month

  Alton Osprey

  1 - 3 Beds

  4000 Destination Dr, Osprey, FL 34229

  Arriving Spring 2025, discover stunning one-, two-, and three-bedroom apartment homes coming to Osprey, 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 works for

  4000 Destination Dr, 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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  /82

  Est $747,113 Not Listed For Sale

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

  250 Hidden Bay Dr Unit A-201, Osprey, FL 34229

  250 Hidden Bay Dr Unit A-201, Osprey, FL 34229
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  /81

  $1,999,000

  • 4 Beds
  • 5 Baths
  • 4,020 Sq Ft

  67 Sugar Mill Dr, Osprey, FL 34229

  This is your rare chance to claim a spectacular estate in Sarasota’s premier golf and country club community THE OAKS. This elegant home seamlessly blends timeless architecture with resort-style living. Beyond the private gates, step into over 4,000 square feet of refined interiors featuring dramatic ceilings, architectural columns, and panoramic views. The expansive layout includes 4 bedrooms, 5

  

  Paula Mapp

  MAPP REALTY & INVESTMENT CO

  (941) 294-4414

  67 Sugar Mill Dr, 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
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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
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  /98

  Est $875,065 Not Listed For Sale

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

  250 Hidden Bay Dr Unit A504, Osprey, FL 34229

  250 Hidden Bay Dr Unit A504, Osprey, FL 34229
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  /100

  $625,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft

  14041 Bellagio Way Unit 315, Osprey, FL 34229

  SIGNIFICANT PRICE IMPROVEMENT! IF YOU HAVE BEEN WAITING FOR A FANTASTIC WATERFRONT PROPERTY AND PRICE.. THIS IS THE ONE! Step into waterfront luxury living at its finest in Osprey Harbor Village, a coastal gem perfectly situated between Sarasota and Venice, offering easy access to Siesta Key, Nokomis Beach, and Venice Beach. This sought-after marina community is the epitome of elegance and the

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 207-5944

  14041 Bellagio Way Unit 315, 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 AUG 1 to SEP 30 / $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 Casey Key,

  236 Woodland Dr, 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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  /50

  Est $1,099,911 Not Listed For Sale

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

  3973 Waypoint Ave, Osprey, FL 34229

  3973 Waypoint Ave, Osprey, FL 34229
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  /60

  $560,000

  • 4 Beds
  • 2 Baths
  • 1,981 Sq Ft

  813 Oak Pond Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. WELCOME HOME!! THERE HAS BEEN NO FLOODING OR DAMAGE FROM RECENT STORMS!! RECENTLY APPRAISED at $560,000!! This is a Beautiful and Spacious 4 bed/2 bath Home in the Community of Bay Oaks Estates. It is just a Short Drive to 3 different Gorgeous Beaches including Nokomis Beach, Venice Beach and the World Famous Siesta Key! Easy Access to Tamiami Trail

  

  Jeremy Egglefield

  PREFERRED SHORE LLC

  (941) 394-8541

  813 Oak Pond Dr, Osprey, FL 34229
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  /39

  $4,200 per month

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Condo for Rent

  Unlisted Address

  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

  Unlisted Address
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  /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
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  /53

  Est $615,059 Not Listed For Sale

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

  4421 Conchfish Ln, Osprey, FL 34229

  4421 Conchfish Ln, Osprey, FL 34229
• 

  

  /80

  $795,000 Pending

  • 4 Beds
  • 4 Baths
  • 2,945 Sq Ft

  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

  (941) 300-1202

  424 Cezanne Dr, Osprey, FL 34229
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  /18

  $1,850 per month

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

  455 Pennsylvania Ave, Osprey, FL 34229

  Available Now – 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,

  455 Pennsylvania Ave, 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
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  /78

  Est $555,799 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,678 Sq Ft

  36 Bishops Court Rd Unit 111, Osprey, FL 34229

  36 Bishops Court Rd Unit 111, Osprey, FL 34229
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  /60

  $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 Covered Parking Spaces and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 404, Osprey, FL 34229
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  /35

  $4,000 per month

  • 3 Beds
  • 2 Baths
  • 2,261 Sq Ft
  • House for Rent

  1279 Thornapple Dr, Osprey, FL 34229

  Annual unfurnished single-family pool home available in Willowbend! Gorgeous Lee Wetherington-built three-bedroom, two-bath home located in the maintenance-free neighborhood of Willowbend in Osprey. The home features a gourmet kitchen with gas cooktop and double oven, 12-foot ceilings, plantation shutters, a solar-heated pool, and spacious lanai with lake view. Willowbend amenities include lawn

  Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1279 Thornapple Dr, Osprey, FL 34229
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  /2

  $1,050,000 Sold Jul 22, 2025

  • 2,531 Sq Ft
  • $415/SF
  • 32 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  142 Dory Ln, Osprey, FL 34229

  Southbay Yacht & Racquet Club, The waterfront Community with Resort-Style Amenities. Welcome to this beautiful three-bedroom two-bathroom home featuring a private pool and spa, perfect for relaxing or entertaining year-round. Located in a highly sought-after waterfront community, this property offers access to a private marina, clubhouse, community pool and scenic park-ideal for enjoying the

  Sharon Lewis GOLF & BAY PROPERTIES LLC

  142 Dory Ln, Osprey, FL 34229
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  /39

  Est $341,823 Not Listed For Sale

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

  4325 Expedition Way Unit 103, Osprey, FL 34229

  4325 Expedition Way Unit 103, Osprey, FL 34229
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  /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
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  /32

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  1847 Highland Rd Unit 1865 Shoreland, Osprey, FL 34229

  Spacious Duplex Villa with community pool in a great area. Close to beaches, shopping & restaurants. Right across Oscar Scherer State Park. Shoreland Park is down the street, where you can launch your kayak.

  1847 Highland Rd Unit 1865 Shoreland, Osprey, FL 34229
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  /2

  $760,000 Sold Jul 16, 2025

  • 3,091 Sq Ft
  • $246/SF
  • 158 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2002

  790 Shadow Bay Way, Osprey, FL 34229

  Brand New Tile Roof March 2025. Experience the ultimate in serene living within the picturesque Woodlands of Rivendell, where this stunning residence seamlessly combines the beauty of nature with modern comforts. Bordered by a preserve at the rear and flanked by mature trees across the street, it offers the perfect sanctuary for those seeking tranquility amidst lush greenery. The curb appeal is

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  790 Shadow Bay Way, Osprey, FL 34229
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  /15

  Est $778,940 Not Listed For Sale

  148 Osprey Point Dr, Osprey, FL 34229

  148 Osprey Point Dr, 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
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  /9

  $2,300 per month

  • 3 Beds
  • 1.5 Baths
  • 1,173 Sq Ft
  • House for Rent

  234 Patterson Ave, Osprey, FL 34229

  Welcome to 234 Patterson Ave, a charming single-family home nestled in the heart of Osprey, Florida. This amazingly located residence offers 3 bedrooms, 1 and a half bathrooms, and 1,173 square feet of comfortable living space. The open-concept layout features vaulted ceilings and a NEW modern kitchen equipped with granite countertops, soft close drawers, a center island, and new Frigidaire

  Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  234 Patterson Ave, Osprey, FL 34229
• 

  /2

  $145,000 Sold Jul 15, 2025

  • 23 Days On Market

  • Built 2006

  570 Blackburn Point Rd Unit 27, Osprey, FL 34229

  Dry boat slip for sale at Osprey Harbor Village hurricane-protected dry storage with top-tier amenities! This rarely available slip 1st level T-Top slip can fit boats up to 12 ft in height 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

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 27, Osprey, FL 34229
• 

  

  /41

  Est $1,142,380 Not Listed For Sale

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

  3932 Waypoint Ave, Osprey, FL 34229

  3932 Waypoint Ave, Osprey, FL 34229

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