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View 82 Osprey Florida Homes for Sale

Home For Sale $673,000

Reduced By $26,000

Enclosed pool and patio area, great for relaxing at 610 Pine Ranch East Rd, Osprey, FL 34229
Relaxing pool area with covered patio and wicker furniture at 610 Pine Ranch East Rd, Osprey, FL 34229
Modern kitchen with stainless steel appliances and quartz countertops at 610 Pine Ranch East Rd, Osprey, FL 34229
On Market For 84 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2431

  • Year Built

    1995

  • $/SqFt

    $277

(Some Furniture available outside of contract) COLDWELL BANKER REALTY.

Home For Sale $1,690,000

House nestled in a waterfront community with lush landscaping at 325 Osprey Point Dr, Osprey, FL 34229
Gray home with a paver driveway and landscaping at dusk at 325 Osprey Point Dr, Osprey, FL 34229
Peaceful waterfront scene with a vibrant sunset reflection at 325 Osprey Point Dr, Osprey, FL 34229
On Market For 86 Days
  • Bedrooms

    3

  • Full Bath(s)

    4

  • Sq. Ft.

    3905

  • Year Built

    1986

  • $/SqFt

    $433

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

Home For Sale $1,850,000

Single-Gathering home with lush landscaping and a three-car garage at 141 Sugar Mill Dr, Osprey, FL 34229
Beautiful home with a three-car garage and a paver driveway at 141 Sugar Mill Dr, Osprey, FL 34229
Luxury home showcasing a two-car garage and lush landscaping at 141 Sugar Mill Dr, Osprey, FL 34229
On Market For 89 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3118

  • Year Built

    2016

  • $/SqFt

    $593

With two distinctly unique 18-hole championship golf courses, 12 HAR-TRU tennis courts (4 lighted), croquet and pickle ball courts, a state-of-the art fitness center, fine and casual dining options, and a wealth for social events, The Oaks is truly Sarasota’s premier golf and country club. COLDWELL BANKER REALTY.

Home For Sale $575,000

Reduced By $75,000

House exterior with a brick driveway and lush landscaping at 264 Woods Point Rd, Osprey, FL 34229
Aerial view of a waterfront community, showcasing a charming villa nestled amongst lush greenery at 264 Woods Point Rd, Osprey, FL 34229
Inviting front entry with brick pavers, a charming door, and a small sitting area at 264 Woods Point Rd, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 106 Days
  • Bedrooms

    2

  • Full Bath(s)

    3

  • Sq. Ft.

    2837

  • Year Built

    1992

  • $/SqFt

    $203

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

Home For Sale $3,875,000

Reduced By $300,000

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 8 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2380

  • Year Built

    1969

  • $/SqFt

    $1,628

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 $925,000

Bird's eye view of single-story home with pool and lush surroundings at 13 Bayhead Ln, Osprey, FL 34229
Aerial view showcasing home near the waterfront in a tranquil community at 13 Bayhead Ln, Osprey, FL 34229
Single-story home nestled in a wooded area with a large yard at 13 Bayhead Ln, Osprey, FL 34229
On Market For 114 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    2310

  • Year Built

    2001

  • $/SqFt

    $400

A Golf equity or Social membership is required with a real estate purchase. MICHAEL SAUNDERS & COMPANY.

Home For Sale $1,795,000

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 127 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 $439,900

Reduced By $10,000

Front view of the house showcasing the entrance and landscaping at 2068 Preymore St, Osprey, FL 34229
Inviting entryway with a red door, unique metalwork, and potted plants at 2068 Preymore St, Osprey, FL 34229
Bright and airy entryway with tile floors and built-in storage at 2068 Preymore St, Osprey, FL 34229
On Market For 134 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1648

  • Year Built

    1995

  • $/SqFt

    $267

Make this fabulous property your new home! You will love living here! COLDWELL BANKER SARASOTA CENT..

Home For Sale $3,995,000

Reduced By $255,000

Luxury waterfront home with circular driveway at 412 Cezanne Dr, Osprey, FL 34229
Luxury waterfront home with pool and expansive grounds at 412 Cezanne Dr, Osprey, FL 34229
Modern home with gray siding, metal roof and large windows at 412 Cezanne Dr, Osprey, FL 34229
On Market For 135 Days
  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4535

  • Year Built

    1975

  • $/SqFt

    $881



This one-of-a-kind property offers luxury, privacy, and the ultimate Florida lifestyle—don’t miss the opportunity to make it yours! CORNERSTONE R.E OF SW FL.

Home For Sale $325,000

Spacious living room featuring a leather sectional sofa, electric fireplace, and hardwood floors at 427 Washington Ave, Osprey, FL 34229
Charming dining room with rustic table, wine storage, and colorful rug at 427 Washington Ave, Osprey, FL 34229
Bright bedroom with tiled floors and built-in closet at 427 Washington Ave, Osprey, FL 34229
On Market For 143 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1120

  • Year Built

    1957

  • $/SqFt

    $290

Call today for more information and to discuss setback details! KELLER WILLIAMS REALTY SELECT.

Home For Sale $868,000

Reduced By $62,000

Single-story house with a teal roof, waterfront property at 1768 S Creek Ln, Osprey, FL 34229
Aerial view of waterfront home community, showcasing houses with lush landscaping and a canal at 1768 S Creek Ln, Osprey, FL 34229
Aerial view of a residential neighborhood with houses, green spaces, and a glimpse of the city at 1768 S Creek Ln, Osprey, FL 34229
On Market For 149 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2837

  • Year Built

    1998

  • $/SqFt

    $306

Don't miss out on this Awesome home - Schedule your viewing today! COASTAL LUXURY PARTNERS, INC..

Pended $2,225,000

Reduced By $70,000

Aerial view of luxury home near water and golf course at 627 Eagle Watch Ln, Osprey, FL 34229
Luxury home exterior with paver driveway and garage at 627 Eagle Watch Ln, Osprey, FL 34229
Luxury home exterior with paver driveway and entryway at 627 Eagle Watch Ln, Osprey, FL 34229
On Market For 155 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3896

  • Year Built

    1989

  • $/SqFt

    $571

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR** GENEROUS PROPERTY.

Home For Sale $1,595,000

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 178 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 $995,000

Reduced By $180,000

Single story home with a large grassy yard at 124 Tina Island Dr, Osprey, FL 34229
Waterfront property with canal access shown in an aerial view at 124 Tina Island Dr, Osprey, FL 34229
Private dock with seating overlooking the canal at 124 Tina Island Dr, Osprey, FL 34229
On Market For 178 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2112

  • Year Built

    1975

  • $/SqFt

    $471

This is the waterfront opportunity you have been waiting for... COLDWELL BANKER SARASOTA CENT..

Home For Sale $649,900

Reduced By $79,100

Charming home with a two-car garage and manicured lawn at 593 Crane Prairie Way, Osprey, FL 34229
Luxury homes with private pools and lake access at 593 Crane Prairie Way, Osprey, FL 34229
Luxury homes with private pools and lake access at 593 Crane Prairie Way, Osprey, FL 34229
On Market For 184 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2340

  • Year Built

    2005

  • $/SqFt

    $278

Centrally located in Osprey within a short distance to beaches, restaurants & shopping. COLDWELL BANKER SARASOTA CENT..

Home For Sale $1,500,000

Inviting pool area with screened enclosure, wicker furniture, and tranquil water feature at 1108 Bayhead Ln, Osprey, FL 34229
Relaxing patio with glass-top table, colorful chairs, and lush landscaping at 1108 Bayhead Ln, Osprey, FL 34229
Mature tree adorned with orchids and other tropical plants at 1108 Bayhead Ln, Osprey, FL 34229
On Market For 185 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3541

  • Year Built

    1997

  • $/SqFt

    $424

Bring your clothes & live happily in this incredibly comforting home. Cheers & welcome home! ILLUSTRATED PROPERTIES LLC (CO.

Home For Sale $425,000

Reduced By $24,900

Aerial view showing home's location and large backyard at 329 Bay Vista Ave, Osprey, FL 34229
Overhead view showcasing home and expansive lot with lush greenery at 329 Bay Vista Ave, Osprey, FL 34229
Renovated kitchen, featuring granite countertops and stainless steel appliances at 329 Bay Vista Ave, Osprey, FL 34229
On Market For 160 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1346

  • Year Built

    1963

  • $/SqFt

    $316

Bay Acres - Electric bill for a full year 2023 was $636.28 HORIZON REALTY INTERNATIONAL.

Pended $1,675,000

Reduced By $125,000

Two-story house with red tile roof, lush landscaping, and a brick driveway at 738 Macewen Dr, Osprey, FL 34229
Two-story house with red tile roof, lush landscaping, and a brick driveway at 738 Macewen Dr, Osprey, FL 34229
Two-story house with red tile roof, lush landscaping, and a brick driveway at 738 Macewen Dr, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 205 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4614

  • Year Built

    2003

  • $/SqFt

    $363

Initiation Fees Going Up On 2/1/2025. Buy Now Before The Increase! COLDWELL BANKER REALTY.

Home For Sale $1,795,000

Reduced By $100,000

Aerial view of a house on a golf course with a pool at 402 Walls Way, Osprey, FL 34229
Bird's-eye view of a rectangular pool with spa and patio area at 402 Walls Way, Osprey, FL 34229
Single-story home with palm trees and manicured lawn at 402 Walls Way, Osprey, FL 34229
On Market For 217 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3464

  • Year Built

    2014

  • $/SqFt

    $518

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR** GENEROUS PROPERTY.

Home For Sale $525,000

Reduced By $75,000

Bird's eye view of a house in a residential neighborhood at 629 Oak Bay Dr, Osprey, FL 34229
Bird's eye view of a house in a residential neighborhood at 629 Oak Bay Dr, Osprey, FL 34229
Single-story house with a landscaped yard and attached garage at 629 Oak Bay Dr, Osprey, FL 34229
On Market For 219 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1996

  • $/SqFt

    $281

Centrally located, this home offers convenient access to the area's picturesque gulf beaches, A-rated schools, the scenic Legacy Trail, Oscar Scherer State Park, and an abundance of shopping, dining, and entertainment options. KELLER WILLIAMS CLASSIC GROUP.

Home For Sale $885,000

Reduced By $65,000

Elegant entryway with double doors and landscaping at 1426 Landview Ln, Osprey, FL 34229
Open living and dining area with fireplace and high ceilings at 1426 Landview Ln, Osprey, FL 34229
Spacious bedroom with a comfortable bed and ensuite bathroom at 1426 Landview Ln, Osprey, FL 34229
On Market For 220 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2513

  • Year Built

    1987

  • $/SqFt

    $352

Southbay Yacht & Racquet Club - (Note: One or more photos have been virtually staged.) COLDWELL BANKER SARASOTA CENT..

Pended $995,000

Reduced By $175,000

Elegant home entry with columns at 1200 Mallard Marsh Dr, Osprey, FL 34229
Bright entryway with double doors, tile floors, and elegant light fixtures at 1200 Mallard Marsh Dr, Osprey, FL 34229
Spacious entryway featuring double doors and a high ceiling at 1200 Mallard Marsh Dr, Osprey, FL 34229
On Market For 146 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2928

  • Year Built

    2002

  • $/SqFt

    $340

Rivendell The Woodlands - Award winning Pine View High School is within walking distance and was voted the #1 High School in the entire state of Florida!! ! RESULTS REALTY GROUP LLC.

Pended $1,395,000

Reduced By $154,000

Luxury home with golf course and lake views at 639 Eagle Watch Lane, Osprey, FL 34229
Two story house with a large driveway at 639 Eagle Watch Lane, Osprey, FL 34229
Two story house with landscaping and driveway at 639 Eagle Watch Lane, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 236 Days
  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    3906

  • Year Built

    1989

  • $/SqFt

    $357

The Oaks has two 18-hole championship golf courses, 12 HAR-TRU tennis courts maintained to tournament standards, 5 of which are lighted, bocce and lighted pickleball courts, a club pool, and a wide variety of dining. NEW ROOF 2022. COLDWELL BANKER REALTY.

Home For Sale $5,500,000

Reduced By $1,000,000

Beachfront property with expansive ocean views at 608 N Casey Key Rd, Osprey, FL 34229
Beachfront property with expansive ocean views at 608 N Casey Key Rd, Osprey, FL 34229
Beachfront property with expansive ocean views at 608 N Casey Key Rd, Osprey, FL 34229
On Market For 253 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3086

  • Year Built

    1916

  • $/SqFt

    $1,782

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

Home For Sale $1,800,000

Reduced By $300,000

Grand two-story home, gray exterior, gray roof, lush landscaping at 97 Sugar Mill Dr, Osprey, FL 34229
Two-story home with pool and lush landscaping. Gray exterior and roof at 97 Sugar Mill Dr, Osprey, FL 34229
Two-story home with a double door entry and lush landscaping at 97 Sugar Mill Dr, Osprey, FL 34229
On Market For 263 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4885

  • Year Built

    1990

  • $/SqFt

    $368

Last but not least a wrap-around second floor balcony that sets the stage for pure elegance. Brand New roof installed 2024! ! COLDWELL BANKER REALTY.

Home For Sale $995,000

Elegant house entrance with double doors and lush landscaping at 12 Bishops Court Rd Rd, Osprey, FL 34229
Single-Gathering home with paver driveway and tropical landscaping at 12 Bishops Court Rd Rd, Osprey, FL 34229
The Oaks Preserve entrance with landscaping and signage at 12 Bishops Court Rd Rd, Osprey, FL 34229
On Market For 302 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3182

  • Year Built

    1996

  • $/SqFt

    $313

Membership is required, either social or golf, and it's all waiting for you to enjoy the wonderful lifestyle convenient to everything Sarasota has to offer. MICHAEL SAUNDERS & COMPANY.

Pended $3,995,000

Luxury home with modern architecture, landscaped grounds, and a paved driveway at 601 Fernwalk Ln, Osprey, FL 34229
Aerial view of a house nestled in lush greenery, near the water at 601 Fernwalk Ln, Osprey, FL 34229
Luxury home showcasing a large lot with mature trees and a paved driveway at 601 Fernwalk Ln, Osprey, FL 34229
On Market For 302 Days
  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    5453

  • Year Built

    1986

  • $/SqFt

    $733

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

Pended $999,000

Reduced By $96,000

One-story home with tile roof and driveway at 201 Saint James Park, Osprey, FL 34229
Home entrance with double doors and arched entryway at 201 Saint James Park, Osprey, FL 34229
Spacious living room with large windows and glass doors at 201 Saint James Park, Osprey, FL 34229
On Market For 252 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2855

  • Year Built

    1997

  • $/SqFt

    $350

Make this your dream home in Paradise. SUBSTANCIAL PRICE IMPROVEMENT! ROSEBAY INTERNATIONAL REALTY, INC.

Home For Sale $289,000

Reduced By $86,000

Home nestled among lush foliage with a gravel driveway at 38 Old Venice Rd, Osprey, FL 34229
Large backyard with a wooden fence and overgrown landscaping at 38 Old Venice Rd, Osprey, FL 34229
A small house with overgrown landscaping and a chain-link fence at 38 Old Venice Rd, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 265 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1163

  • Year Built

    1960

  • $/SqFt

    $248

See this one for yourself; book a showing today. CHARLES RUTENBERG REALTY INC.

Home For Sale $4,500,000

Reduced By $400,000

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 483 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.

Home For Sale $389,000

New construction home exterior with Tyvek HomeWrap at 206 Patterson Ave, Osprey, FL 34229
New home under construction, Tyvek covering at 206 Patterson Ave, Osprey, FL 34229
New construction home exterior, Tyvek wrap at 206 Patterson Ave, Osprey, FL 34229
On Market For 498 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1242

  • Year Built

    2023

  • $/SqFt

    $313

New Construction and is scheduled to be done Mid to late Summer. EXIT GULF COAST REALTY.

Home For Sale $389,000

New construction home with a wrap-around deck and spacious yard at 202 Patterson Ave, Osprey, FL 34229
New construction home with a wrap-around deck and spacious yard at 202 Patterson Ave, Osprey, FL 34229
New construction home with a wrap-around deck and spacious yard at 202 Patterson Ave, Osprey, FL 34229
On Market For 500 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1242

  • Year Built

    2023

  • $/SqFt

    $313

Construction started and expected to be completed in mid to late Summer. EXIT GULF COAST REALTY.

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Call to Schedule a Showing

(813) 527-9259

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