Osprey, FL Homes

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  /93

  $750,000

  • 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
• Explore Osprey

• 

  

  

  /47

  $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
• 

  

  /2

  $1,325,000 Sold Nov 07, 2025

  • 3,464 Sq Ft
  • $383/SF
  • 187 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2014

  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
• 

  

  

  /39

  Est $370,338 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
• 

  

  

  /88

  $1,200,000 Pending

  • 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
• 

  

  /40

  $6,000 per month

  • 2 Beds
  • 3 Baths
  • 1,709 Sq Ft
  • House for Rent

  716 Sarabay Rd, Osprey, FL 34229

  Experience Waterfront Luxury at 716 Sarabay Road, Osprey, FL. Welcome to your private waterfront retreat on Little Sarasota Bay. This stunning 2-bedroom, 3-bath residence offers over 100 feet of direct bay frontage and has been meticulously renovated throughout, combining modern luxury with timeless coastal charm. The open-concept living space is bright and inviting, featuring designer finishes

  

  Mitchell Roberts

  PARADISE REALTY OF VENICE INC

  (941) 241-3260

  716 Sarabay Rd, Osprey, FL 34229
• 

  /2

  $1,850,000 Sold Nov 07, 2025

  • 4,020 Sq Ft
  • $460/SF
  • 240 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1989

  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

  67 Sugar Mill Dr, Osprey, FL 34229
• 

  

  /70

  Est $1,104,661 Not Listed For Sale

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

  3961 Waypoint Ave, Osprey, FL 34229

  3961 Waypoint Ave, Osprey, FL 34229
• 

  

  /55

  $629,000

  • 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 INTERNATION

  (941) 239-7527

  583 Pine Ranch East Rd, Osprey, FL 34229
• 

  

  /49

  $3,800 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
• 

  /2

  $665,000 Sold Nov 06, 2025

  • 2,346 Sq Ft
  • $283/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  563 Pine Ranch Rd E, Osprey, FL 34229

  Step into your dream home in the sought-after Bay Oaks Estates where comfort, functionality and location come together in perfect harmony. From the moment you arrive, you'll be captivated by the curb appeal and the welcoming presence that instantly feels like home. Beautifully designed, this split-plan residence offers space, style and seamless flow. The double-door entry opens into a foyer,

  Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  563 Pine Ranch Rd E, Osprey, FL 34229
• 

  

  /98

  Est $782,880 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
• 

  

  /41

  $340,000

  • 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
• 

  

  /10

  $2,500 per month

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

  51 Mac Ewen Dr Unit 1, Osprey, FL 34229

  ***AVAILABLE NOVEMBER 2025 THRU JANUARY 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located in South Sarasota. Open plan, easy to show! Close to Siesta Key, Costco restaurants very convenient to all the amenities Sarasota has to offer.

  

  Anthony DeLuca

  AUDREY RAIN RENTALS, INC

  (941) 207-5680

  51 Mac Ewen Dr Unit 1, Osprey, FL 34229
• 

  /2

  $43,000 Sold Nov 04, 2025

  • 98 Days On Market

  570 Blackburn Point Rd Unit 6, Osprey, FL 34229

  Dry Boat Slip for Sale – Osprey Harbor Village, Sarasota County Secure your spot in one of Sarasota County’s premier boating destinations with this hurricane-protected dry boat slip at Osprey Harbor Village. Designed to offer both protection and convenience, this indoor slip ensures your boat is shielded from Florida’s unpredictable weather — potentially reducing your insurance premiums by

  Rick Bumbaca AZZURRO REALTY

  570 Blackburn Point Rd Unit 6, Osprey, FL 34229
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  /50

  Est $1,092,708 Not Listed For Sale

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

  3973 Waypoint Ave, Osprey, FL 34229

  3973 Waypoint Ave, Osprey, FL 34229
• 

  

  /65

  $1,075,000

  • 4 Beds
  • 4.5 Baths
  • 3,533 Sq Ft

  701 Eaglenook Way, Osprey, FL 34229

  A truly rare opportunity to own a home on over 2 acres in Osprey, FL. Pine Ranch is a charming enclave of 36 properties with low HOA fees and sensible deed restrictions that offers room for your RV, boat, and space for your horses.Conveniently positioned one mile East of US 41, within a mile of the Legacy Trail and the nationally-ranked Pine View School. Situated at the end of a

  

  Michael Ballantyne

  COLDWELL BANKER SARASOTA CENT.

  (941) 883-9471

  701 Eaglenook Way, Osprey, FL 34229
• 

  

  /252

  $1,599 - $3,025 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 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

  4000 Destination Dr, Osprey, FL 34229
• 

  /2

  $1,495,000 Sold Oct 31, 2025

  • 2,425 Sq Ft
  • $616/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1997

  228 Saint James Park, Osprey, FL 34229

  Experience the unparalleled charm and convenience of this golf course home in The Oaks Club, the country club community designed by noted Sarasota architect Bo MacEwen. 228 Saint James Park is an original Bo MacEwen design, is located on the leafy and quiet Saint James Park cul-de-sac, and directly overlooks the opening hole of the Heron golf course. This single-floor three-bedroom,

  Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  228 Saint James Park, Osprey, FL 34229
• 

  

  /53

  Est $570,499 Not Listed For Sale

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

  4421 Conchfish Ln, Osprey, FL 34229

  4421 Conchfish Ln, Osprey, FL 34229
• 

  

  /98

  $1,150,000

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

  1218 Yacht Harbor Dr, Osprey, FL 34229

  New listing alert 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, basketball courts, and kayak storage. Residents also enjoy a waterfront park

  

  Karie Backman

  KELLER WILLIAMS ON THE WATER S

  (941) 352-2028

  1218 Yacht Harbor Dr, Osprey, FL 34229
• 

  

  /39

  $2,950 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  4429 Conchfish Ln, Osprey, FL 34229

  Steps from Pine View School, Florida's #1 public school, with 2,008 sq. ft. of living space, this home features brand-new thick waterproof laminate wood flooring in all bedrooms and closets, an ocean-inspired guest bathroom, and tile throughout the main living areas for easy maintenance. Enjoy the covered lanai overlooking a private backyard, perfect for relaxing or entertaining, and take

  JIA SONG Jia Song Realty

  4429 Conchfish Ln, Osprey, FL 34229
• 

  /2

  $2,315,000 Sold Oct 30, 2025

  • 8,635 Sq Ft
  • $268/SF
  • 156 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1989

  112 Osprey Point Dr, Osprey, FL 34229

  Premier Waterfront Opportunity in The Oaks BaysideThis grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers sweeping views of Little Sarasota Bay and exceptional potential. With its expansive floor plan across three levels, soaring ceilings, and dramatic architectural features, this residence was built to

  Kara Money KARA MONEY LLC

  112 Osprey Point Dr, Osprey, FL 34229
• 

  

  /78

  Est $513,843 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
• 

  

  /60

  $550,000 Pending

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

  813 Oak Pond Dr, Osprey, FL 34229

  Under contract-accepting backup offers. 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

  

  Jeremy Egglefield

  PREFERRED SHORE LLC

  (941) 394-8541

  813 Oak Pond Dr, Osprey, FL 34229
• 

  

  /20

  $3,450 per month

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

  6 Bay Acres Ave Unit ID1228250P, Osprey, FL 34229

  Step into a sunlit, single-story retreat with two inviting bedrooms and two modern bathrooms. Designed for families or groups of friends, this home seamlessly blends comfort with elegance. Located just moments away, dive into the vibrant St. Armand's Circle or unwind on the pristine sands of Siesta Key and Nokomis Beaches.This space includes everything needed for a quality and memorable

  6 Bay Acres Ave Unit ID1228250P, Osprey, FL 34229
• 

  /2

  $425,000 Sold Oct 29, 2025

  • 2,837 Sq Ft
  • $150/SF
  • 368 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1992

  264 Woods Point Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Fresh paint is done, and new carpet is coming. SELLER WILL CONSIDER LEASE PURCHASE. Try it before you buy it. Price reflects the need to update property interior. With expected ARV (after repair value) of +/- $600k, $91 per square foot under the most recent sale in the neighborhood, and less than a mile from the beach this is a great opportunity to

  Mark Midyett KELLER WILLIAMS ON THE WATER S

  264 Woods Point Rd, Osprey, FL 34229
• 

  

  /15

  Est $803,243 Not Listed For Sale

  148 Osprey Point Dr, Osprey, FL 34229

  148 Osprey Point Dr, Osprey, FL 34229
• 

  

  /69

  $3,950,000

  • 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
• 

  

  /37

  $2,950 per month

  • 4 Beds
  • 2 Baths
  • House for Rent

  4417 Conchfish Ln, Osprey, FL 34229

  This one-story home offers 1861 sqft living space, with four bedrooms, two bathrooms, and a two-car garage. Open-concept floor plan. Welcome to 4417 Conchfish Ln, a beautifully maintained 4-bedroom, 2-bathroom home located in the highly sought-after community of Osprey, FL just steps from the top-rated Pine View School. This spacious home features an open kitchen layout with a brand-new

  JIA SONG Jia Song Realty

  4417 Conchfish Ln, Osprey, FL 34229
• 

  /2

  $1,750,000 Sold Oct 27, 2025

  • 3,857 Sq Ft
  • $454/SF
  • 1 Day On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2000

  627 N MacEwen Dr, Osprey, FL 34229

  **STUNNING GOLF COURSE ESTATE with WATER and GOLF COURSE VIEW in the Highly Sought-After OAKS COUNTRY CLUB Community** with Ideal Southern-Exposure and View across the 15TH Green of the interior, HERON GOLF COURSE. With its delightful curb appeal and gorgeously manicured landscape, this residence offers 4 EN SUITE BEDROOMS + Study/Den, 4 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings,

  Mark Lyda GENEROUS PROPERTY

  627 N MacEwen Dr, Osprey, FL 34229
• 

  

  /41

  Est $1,144,390 Not Listed For Sale

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

  3932 Waypoint Ave, Osprey, FL 34229

  3932 Waypoint Ave, Osprey, FL 34229
• 

  

  /84

  $970,000

  • 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
• 

  

  /20

  $3,450 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
• 

  /2

  $730,000 Sold Oct 24, 2025

  • 2,320 Sq Ft
  • $315/SF
  • 44 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  1728 S Creek Dr, Osprey, FL 34229

  Immaculate 3-bedroom 2-bath home in the highly desirable waterfront gated community of South Creek.This meticulously cared-for property features a 2,320 SqFt split floor plan with a primary suite on one side and aguest retreat on the other side, all facing the outdoor living with a lap pool surrounded by lush landscaping. The secondbath room is a pool bath. Additional home features

  Melanie Albaric MICHAEL SAUNDERS & COMPANY

  1728 S Creek Dr, Osprey, FL 34229
• 

  

  /63

  Est $1,014,866 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
• 

  

  /45

  $3,200,000

  • Land
  • 0.39 Acre
  • $8,205,128 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
• 

  

  /43

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • House for Rent

  163 Pennsylvania Ave, Osprey, FL 34229

  Welcome to 163 Pennsylvania Avenue, nestled in the quaint community of Osprey, FL. This charming 3-bedroom, 2-bathroom home, built in 2018, offers a smart blend of style and energy efficiency. Spanning 1,346 square feet, the open floor plan showcases a modern grey color palette, creating an inviting ambiance throughout. Step into the kitchen, where sleek stainless steel appliances and light wood

  Beth Harris COMPASS FLORIDA LLC

  163 Pennsylvania Ave, Osprey, FL 34229
• 

  /2

  $1,200,000 Sold Oct 24, 2025

  • 3,479 Sq Ft
  • $345/SF
  • 82 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1987

  1484 Seafarer Dr, Osprey, FL 34229

  Welcome to Southbay Yacht & Racquet Club, one of the Gulf Coast’s most coveted communities—where every day feels like a vacation! Southbay boasts a world-class private marina with 172 deep-water slips, accommodating yachts up to 55 feet, along with personal watercraft and kayaks. Slip rentals are available and offered at a highly competitive rate, making this an exceptional value for boating

  Seth Westerberg EXP REALTY LLC

  1484 Seafarer Dr, Osprey, FL 34229
• 

  

  /67

  Est $570,747 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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