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View 78 Osprey Florida Homes for Sale

Pended $2,495,000

Stunning curb appeal! This home features a beautiful tile walkway leading to the entrance at 230 Osprey Point Dr, Osprey, FL 34229
View Details 69 Photos
Inviting pool area with a covered lanai and comfortable seating at 230 Osprey Point Dr, Osprey, FL 34229
Elegant living room with hardwood floors, fireplace, and ample natural light at 230 Osprey Point Dr, Osprey, FL 34229
Gourmet kitchen boasting granite countertops and stainless steel appliances at 230 Osprey Point Dr, Osprey, FL 34229
On Market For 115 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3586

  • Year Built

    2014

  • $/SqFt

    $696

**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** GENEROUS PROPERTY.

Home For Sale $2,995,000

Reduced By $155,000

Beautiful 1-story home with a tile roof and lush landscaping at 662 Fernwalk Ln, Osprey, FL 34229
View Details 80 Photos
Luxury home nestled in a quiet neighborhood with water views at 662 Fernwalk Ln, Osprey, FL 34229
Inviting pool and spa area with screened enclosure and patio furniture at 662 Fernwalk Ln, Osprey, FL 34229
Spacious living room featuring hardwood floors and a cozy fireplace at 662 Fernwalk Ln, Osprey, FL 34229
On Market For 123 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4359

  • Year Built

    1989

  • $/SqFt

    $687

**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** GENEROUS PROPERTY.

Home For Sale $997,000

Reduced By $192,000

Aerial view of two-story home with tile roof, landscaping, and water views at 3904 Waypoint Ave, Osprey, FL 34229
View Details 43 Photos
Tan house with tile roof, landscaping, and two-car garage at 3904 Waypoint Ave, Osprey, FL 34229
Aerial view of a single Gathering home with a two-car garage and lush landscaping at 3904 Waypoint Ave, Osprey, FL 34229
Wide aerial view of waterfront community with single Gathering home highlighted at 3904 Waypoint Ave, Osprey, FL 34229
On Market For 124 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2344

  • Year Built

    2016

  • $/SqFt

    $425

With its prime location on a quiet cul-de-sac, this home promises an incredible lifestyle enriched by the natural beauty of its surroundings. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $795,000

Reduced By $100,000

Beautiful two-story home with large windows, three-car garage, and lush landscaping at 424 Cezanne Dr, Osprey, FL 34229
View Details 80 Photos
Lovely two-story home featuring lush landscaping and a brick driveway at 424 Cezanne Dr, Osprey, FL 34229
A private pool with glass screen showcasing a stunning garden in the background at 424 Cezanne Dr, Osprey, FL 34229
Bright, carpeted staircase featuring white railings and neutral walls at 424 Cezanne Dr, Osprey, FL 34229
On Market For 120 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2945

  • Year Built

    1975

  • $/SqFt

    $270

Seller is in the process of having a brand new septic and drainfield installed. MICHAEL SAUNDERS & COMPANY.

Home For Sale $1,185,000

Reduced By $215,000

Attractive two-story house with three-car garage, manicured landscaping, and a circular driveway at 135 N Creek Ln, Osprey, FL 34229
View Details 49 Photos
Luxury home with pool, situated in a residential neighborhood near water at 135 N Creek Ln, Osprey, FL 34229
Community overview featuring a golf course, water features, and numerous houses at 135 N Creek Ln, Osprey, FL 34229
Beautiful house with a three-car garage, palm trees, and well-maintained landscaping at 135 N Creek Ln, Osprey, FL 34229
On Market For 128 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3160

  • Year Built

    2005

  • $/SqFt

    $375

Experience the pinnacle of Florida living in this exceptional home. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $699,900

Reduced By $80,100

Single-story house with tile roof, attached garage, and landscaped yard at 1212 Windward Dr, Osprey, FL 34229
View Details 39 Photos
An aerial view showcasing a home's location within a residential community at 1212 Windward Dr, Osprey, FL 34229
An aerial view of a single story home with a red tile roof in a residential neighborhood at 1212 Windward Dr, Osprey, FL 34229
Bright kitchen boasts white cabinets, tile floors, and ample counter space at 1212 Windward Dr, Osprey, FL 34229
On Market For 129 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1994

  • Year Built

    1982

  • $/SqFt

    $351

Community amenities include clubhouse, tennis & pickleball, and proximity to Pine View School, Legacy Trail, beaches & more! GENEROUS PROPERTY.

Pended $2,450,000

Luxury home with pool and lush landscaping on a golf course at 654 Trenton Way, Osprey, FL 34229
View Details 85 Photos
Resort-style backyard oasis with pool, fire pit, and patio at 654 Trenton Way, Osprey, FL 34229
Inviting freeform pool and spa with covered patio and sunset views at 654 Trenton Way, Osprey, FL 34229
Relaxing fire pit area with comfortable seating in the backyard at 654 Trenton Way, Osprey, FL 34229
On Market For 132 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3582

  • Year Built

    1990

  • $/SqFt

    $684

**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** GENEROUS PROPERTY.

Pended $670,000

Reduced By $79,900

Attractive single-story home with landscaped yard and palm trees at 455 Park Trace Blvd, Osprey, FL 34229
View Details 42 Photos
Single-story house with lush landscaping and a palm tree in front at 455 Park Trace Blvd, Osprey, FL 34229
Peaceful lakefront view with homes and lush greenery at 455 Park Trace Blvd, Osprey, FL 34229
Serene lake view from a lush, grassy backyard at 455 Park Trace Blvd, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 136 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2590

  • Year Built

    1999

  • $/SqFt

    $259

Nestled in a beautifully maintained neighborhood with unusually low HOA fees (under $57 a MONTH), this home offers a rare opportunity to experience waterfront living at an exceptional price! MICHAEL SAUNDERS & COMPANY.

Home For Sale $1,045,000

Reduced By $180,000

Beautiful yellow home with lush landscaping and a large driveway at 227 Saint James Park, Osprey, FL 34229
View Details 67 Photos
Relaxing screened patio with outdoor furniture and view of lush greenery at 227 Saint James Park, Osprey, FL 34229
Aerial view of house and golf course community at 227 Saint James Park, Osprey, FL 34229
Bright yellow house with a large driveway and manicured lawn at 227 Saint James Park, Osprey, FL 34229
On Market For 137 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    2071

  • Year Built

    1986

  • $/SqFt

    $505

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. GENEROUS PROPERTY.

Home For Sale $2,150,000

Beautiful one-story home with lush landscaping and a large lawn at 85 Sugar Mill Dr, Osprey, FL 34229
View Details 68 Photos
Luxury home with a spacious lot and water views at 85 Sugar Mill Dr, Osprey, FL 34229
Luxury home with a large driveway and manicured landscaping at 85 Sugar Mill Dr, Osprey, FL 34229
Inviting pool and spa area with covered patio at 85 Sugar Mill Dr, Osprey, FL 34229
On Market For 138 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    4191

  • Year Built

    1991

  • $/SqFt

    $513

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. GENEROUS PROPERTY.

Home For Sale $799,900

Reduced By $37,100

Charming home showcasing lush landscaping, a three-car garage, and inviting front entryway at 790 Shadow Bay Way, Osprey, FL 34229
View Details 54 Photos
Aerial view of house encircled, showcasing roof and tree coverage within lush surroundings at 790 Shadow Bay Way, Osprey, FL 34229
An aerial perspective displays the home near a tranquil lake surrounded by trees at 790 Shadow Bay Way, Osprey, FL 34229
Home exterior featuring a spacious driveway, three-car garage, and landscaped front yard at 790 Shadow Bay Way, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 142 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3091

  • Year Built

    2002

  • $/SqFt

    $259

Plus, it's located in a preferred X flood zone with no CDD fees, making it a smart choice for any homeowner. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $910,000

Attractive single-story home with a gray exterior, tile roof, and landscaped front yard at 293 Turquoise Ln, Osprey, FL 34229
View Details 44 Photos
Aerial view showcasing a home's location in a community with water access at 293 Turquoise Ln, Osprey, FL 34229
Single-story home with tile roof, paver driveway, and lush landscaping at 293 Turquoise Ln, Osprey, FL 34229
Bright entryway with double doors, wood-look floors, and neutral wall decor at 293 Turquoise Ln, Osprey, FL 34229
On Market For 143 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2271

  • Year Built

    2001

  • $/SqFt

    $401

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. GENEROUS PROPERTY.

Home For Sale $724,900

Reduced By $21,000

Charming single-story home with a tile roof, lush landscaping, and an attached three-car garage at 644 Rivendell Blvd, Osprey, FL 34229
View Details 64 Photos
Inviting single-story home featuring a well-manicured lawn, arched entryway, and attached two-car garage at 644 Rivendell Blvd, Osprey, FL 34229
Close-up of an arched doorway with sidelights and lush landscaping surrounding the front entrance at 644 Rivendell Blvd, Osprey, FL 34229
Landscaped yard with lush greenery and palm trees, showcasing a beige house at 644 Rivendell Blvd, Osprey, FL 34229
On Market For 144 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2298

  • Year Built

    2001

  • $/SqFt

    $315

Rivendell - Within walking distance to Pine View School, this home also offers easy access to the Legacy Trail & Gulf beaches. Seller will consider all offers. MICHAEL SAUNDERS & COMPANY.

Pended $1,795,000

Stunning contemporary home with landscaped grounds and a paved driveway at 269 Pine Ranch Trl, Osprey, FL 34229
View Details 77 Photos
A stunning white modern home with palm trees and a paved walkway leading to the entrance at 269 Pine Ranch Trl, Osprey, FL 34229
Curved white stucco home with double doors and lush landscaping at 269 Pine Ranch Trl, Osprey, FL 34229
Modern double door entry with arched entryway and stone walkway at 269 Pine Ranch Trl, Osprey, FL 34229
On Market For 122 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3572

  • Year Built

    1997

  • $/SqFt

    $503

Add to all this a 2 CAR GARAGE with mechanic’s pit and a storage closet, a TWO MONTH OLD NEW ROOF, ALL IMPACT DOORS AND WINDOWS, a garden and gardener’s shed, with the ability to connect a sink, and so much more you truly must see this fabulous abode! COLDWELL BANKER REALTY.

Pended $749,000

Reduced By $40,000

Stunning lakefront home featuring manicured landscaping, a three-car garage, and a tile roof at 518 Luminary Blvd, Osprey, FL 34229
View Details 46 Photos
Charming single-story home featuring lush landscaping, a well-manicured lawn and a two-car garage at 518 Luminary Blvd, Osprey, FL 34229
Aerial view showcases this property's premier lakefront location with neighborhood views at 518 Luminary Blvd, Osprey, FL 34229
Aerial view of a lakeside property with lush landscaping and proximity to a serene lake at 518 Luminary Blvd, Osprey, FL 34229
On Market For 147 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2320

  • Year Built

    2005

  • $/SqFt

    $323

Seller will be contributing up to 2% towards a 2/1 INTEREST RATE BUY DOWN for buyer at closing. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $610,000

Reduced By $35,000

Gray house with blue door, columned porch, and landscaped yard at 566 Oak Bay Dr, Osprey, FL 34229
View Details 51 Photos
Gray house with blue door, columned porch, and landscaped yard at 566 Oak Bay Dr, Osprey, FL 34229
Gray house with blue door, columned porch, and landscaped yard at 566 Oak Bay Dr, Osprey, FL 34229
Gray house with blue door, columned porch, and landscaped yard at 566 Oak Bay Dr, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 151 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2559

  • Year Built

    1997

  • $/SqFt

    $238

If you are looking for a spacious pool home in a quiet secluded neighborhood look no more, you have found your forever home. SARABAY REAL ESTATE INC.

Pended $3,997,000

Reduced By $753,000

Luxury waterfront home with a large lot and stunning landscaping at 275 Lookout Point Dr, Osprey, FL 34229
View Details 100 Photos
Grand estate with a circular driveway and lush landscaping at 275 Lookout Point Dr, Osprey, FL 34229
Waterfront property boasting a large home and beautiful views at 275 Lookout Point Dr, Osprey, FL 34229
Expansive waterfront property with a private dock at 275 Lookout Point Dr, Osprey, FL 34229
On Market For 156 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5279

  • Year Built

    2007

  • $/SqFt

    $757

For those who seek an exceptional waterfront life, nothing compares. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $2,495,000

Reduced By $200,000

Charming single-story home featuring a tile roof, stucco siding, a quaint porch, and manicured landscaping at 312 Yacht Harbor Dr, Osprey, FL 34229
View Details 69 Photos
Property with water access and many boats in a marina at 312 Yacht Harbor Dr, Osprey, FL 34229
House with tile roof, palm trees, and a manicured lawn at 312 Yacht Harbor Dr, Osprey, FL 34229
Open floor plan living area with seating, dining, and water views at 312 Yacht Harbor Dr, Osprey, FL 34229
On Market For 180 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2572

  • Year Built

    1978

  • $/SqFt

    $970

Be sure to request a copy of the 50-page digital property catalog, along with viewing the property film. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $1,825,000

Reduced By $25,000

Stunning two-story home boasts lush landscaping, a red tile roof, and a circular driveway at 401 Walls Way, Osprey, FL 34229
View Details 89 Photos
Charming front entrance with brick walkway and well-maintained tropical landscaping at 401 Walls Way, Osprey, FL 34229
Charming exterior elevation with a large, well-manicured lawn and a long driveway at 401 Walls Way, Osprey, FL 34229
Inviting foyer with hardwood floors, a decorative mirror, and a grand double-door entry at 401 Walls Way, Osprey, FL 34229
On Market For 182 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4388

  • Year Built

    1990

  • $/SqFt

    $416

Don’t miss this opportunity to bring your most discerning clients to experience this extraordinary home. RE/MAX ALLIANCE GROUP.

Home For Sale $1,199,000

Reduced By $76,000

Gray house with metal roof, landscaping, and paved pathway at 120 Lookout Point Dr, Osprey, FL 34229
View Details 57 Photos
Aerial view showcasing the house and surrounding neighborhood at 120 Lookout Point Dr, Osprey, FL 34229
Gray house with metal roof, landscaping, and two palm trees at 120 Lookout Point Dr, Osprey, FL 34229
Gray house with metal roof, landscaping, and a walkway at 120 Lookout Point Dr, Osprey, FL 34229
On Market For 191 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2925

  • Year Built

    1985

  • $/SqFt

    $410

Southbay Yacht & Racquet Club - Private Marina, Tennis, Pickle Ball, Community Pool, Waterfront Park, Playground Clubhouse, Fitness Room and So much more! GOLF & BAY PROPERTIES LLC.

Home For Sale $959,000

Single-story house with landscaped yard, palm trees, and a brick driveway at 21 Bayhead Ln, Osprey, FL 34229
View Details 92 Photos
Bird's-eye view of a house and surrounding neighborhood, near the water at 21 Bayhead Ln, Osprey, FL 34229
Property showcasing a tile roof, and a lush green lawn at 21 Bayhead Ln, Osprey, FL 34229
House with tile roof and driveway, surrounded by trees and landscaping at 21 Bayhead Ln, Osprey, FL 34229
On Market For 195 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2216

  • Year Built

    2002

  • $/SqFt

    $433

There are two 18 hole championship golf courses, 12 HarTru tennis courts, 4 pickleball courts, croquet and many social activities. Membership is required. MICHAEL SAUNDERS & COMPANY.

Home For Sale $749,000

Reduced By $50,000

Tan house with lush landscaping, a walkway, and a double door entry at 524 Oak Bay Dr, Osprey, FL 34229
View Details 50 Photos
Single-story house with circular driveway and mature landscaping at 524 Oak Bay Dr, Osprey, FL 34229
Arial view of a house and surrounding neighborhood with golf course visible at 524 Oak Bay Dr, Osprey, FL 34229
Inviting entryway surrounded by tropical plants and a double door at 524 Oak Bay Dr, Osprey, FL 34229
On Market For 202 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2767

  • Year Built

    1998

  • $/SqFt

    $271

HOA fee is only $270.00 annually. New roof in 2019! COLDWELL BANKER REALTY.

Home For Sale $915,000

Reduced By $36,000

Charming two-story home with a three-car garage, tile roof, and well-maintained landscaping at 650 Crane Prairie Way, Osprey, FL 34229
View Details 55 Photos
Exterior angle of a beige home showcasing brick pavers leading to an arched doorway and three car garage at 650 Crane Prairie Way, Osprey, FL 34229
Screened-in pool area with water view, perfect for relaxing and entertaining at 650 Crane Prairie Way, Osprey, FL 34229
Elegant Willowbend community sign amidst lush greenery and mature trees at 650 Crane Prairie Way, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 215 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    3183

  • Year Built

    2005

  • $/SqFt

    $287

Don't miss out on this rare opportunity to embrace the essence of coastal living in Osprey. Your dream home awaits! KELLER WILLIAMS ON THE WATER.

Home For Sale $485,000

Reduced By $165,000

Aerial view of a house with a tile roof and two-car garage at 264 Woods Point Rd, Osprey, FL 34229
View Details 70 Photos
Expansive aerial view of a community with lush greenery and a variety of beautiful homes featuring terracotta roofs at 264 Woods Point Rd, Osprey, FL 34229
House exterior with a brick driveway and lush landscaping at 264 Woods Point Rd, Osprey, FL 34229
Aerial view showcases coastal neighborhood; terracotta roofs, surrounding trees and proximity to the intercoastal waterway at 264 Woods Point Rd, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 213 Days

  • Bedrooms

    2

  • Full Bath(s)

    3

  • Sq. Ft.

    2837

  • Year Built

    1992

  • $/SqFt

    $171

Don’t let this one get away. KELLER WILLIAMS ON THE WATER S.

Home For Sale $3,475,000

Reduced By $700,000

Beachfront patio with lounge chairs and outdoor dining at 5 N Casey Key Rd, Osprey, FL 34229
View Details 96 Photos
Ocean view pathway leads to home entrance, with landscaping and lighting at 5 N Casey Key Rd, Osprey, FL 34229
Bright living room with ocean view and sliding doors at 5 N Casey Key Rd, Osprey, FL 34229
Beachfront patio features white furniture and ocean views at 5 N Casey Key Rd, Osprey, FL 34229
On Market For 143 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2380

  • Year Built

    1969

  • $/SqFt

    $1,460

The allure of this locale is undeniable, as Casey Key Road was recently acclaimed the most coveted street nationwide, underscoring the status of this incredible barrier island. AYERS AND ASSOCIATES REAL ESTATE.

Home For Sale $1,795,000

Luxury home with tile roof and circular driveway, aerial view at 909 Macewen Dr, Osprey, FL 34229
View Details 62 Photos
Mediterranean style home with palm trees and circular driveway at 909 Macewen Dr, Osprey, FL 34229
Screened pool and spa with brick pavers and covered patio area at 909 Macewen Dr, Osprey, FL 34229
Elegant home with double doors and circular driveway at 909 Macewen Dr, Osprey, FL 34229
On Market For 262 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    4241

  • Year Built

    1991

  • $/SqFt

    $423

**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** GENEROUS PROPERTY.

Home For Sale $1,595,000

Spanish style home with circular driveway, mature landscaping, and attached garage at 360 N Point Rd, Osprey, FL 34229
View Details 57 Photos
Bird's eye view of single story home with red tile roof and circular driveway at 360 N Point Rd, Osprey, FL 34229
Aerial of luxury condos with water views and private villas at 360 N Point Rd, Osprey, FL 34229
Front view of charming Spanish style home with a covered entryway at 360 N Point Rd, Osprey, FL 34229
On Market For 313 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2913

  • Year Built

    2023

  • $/SqFt

    $548

One or more photo(s) has been virtually staged. **ENJOY THE 3D VIRTUAL TOUR** GENEROUS PROPERTY.

Home For Sale $4,500,000

Reduced By $400,000

Aerial view of waterfront property with private dock and lush landscaping at 426 N Casey Key Rd, Osprey, FL 34229
View Details 41 Photos
Charming single story home with teal door and lush landscaping at 426 N Casey Key Rd, Osprey, FL 34229
Waterfront home nestled amongst tropical foliage, offering a private dock at 426 N Casey Key Rd, Osprey, FL 34229
Wide shot of waterfront lot with mature palm trees and ocean views at 426 N Casey Key Rd, Osprey, FL 34229
On Market For 618 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1876

  • Year Built

    1992

  • $/SqFt

    $2,399

Come see why those that are lucky enough to call Casey Key home, are lucky indeed! PREMIER SOTHEBYS INTL REALTY.

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