Home For Sale $4,475,000
275 Lookout Point Dr, Osprey, FL 34229
Reduced By $275,000
Bedrooms
5
Full Bath(s)
Sq. Ft.
5279
Year Built
2007
$/SqFt
$848
For those who seek an exceptional waterfront life, nothing compares. PREMIER SOTHEBYS INTL REALTY.
Home For Sale $745,000
710 Shadow Bay Way, Osprey, FL 34229
Reduced By $50,000
3
2533
2002
$294
Rivendell - Ideally situated near Pine View School, Legacy Trail, beaches, parks, and boating, this home provides the perfect combination of comfort, style, and convenience. Seller's are motivated! MICHAEL SAUNDERS & COMPANY.
Pended $2,195,000
1862 Island Way, Osprey, FL 34229
Reduced By $230,000
4
3598
1982
$610
The singular combination of location, waterfront and size make this a desirable property for an exceptional lifestyle. PREMIER SOTHEBYS INTL REALTY.
Pended $1,150,000
247 Keel Way, Osprey, FL 34229
2
2871
1979
$401
Southbay Yacht & Racquet Club - Come take a look for yourself and see why this home in Southbay may be just what you are looking for! PAT WILLIAMS REALTY, LLC.
Home For Sale $2,695,000
312 Yacht Harbor Dr, Osprey, FL 34229
2572
1978
$1,048
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
401 Walls Way, Osprey, FL 34229
Reduced By $25,000
4388
1990
$416
Don’t miss this opportunity to bring your most discerning clients to experience this extraordinary home. RE/MAX ALLIANCE GROUP.
Home For Sale $828,500
448 Park Trace Blvd, Osprey, FL 34229
Reduced By $121,500
3060
$271
Park Trace Estates - Sarasota County’s world-renowned beaches, vibrant downtown districts in Sarasota and Venice, and opportunities for saltwater fishing are all just moments from your doorstep. KELLER WILLIAMS CLASSIC GROUP.
Home For Sale $698,000
123 Tina Island Dr, Osprey, FL 34229
Reduced By $51,900
1922
1964
$363
Property did not have any flood damage. COLDWELL BANKER SARASOTA CENT..
Home For Sale $2,350,000
703 Macewen Dr, Osprey, FL 34229
Reduced By $150,000
4641
$506
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.
Pended $1,500,000
378 Macewen Dr, Osprey, FL 34229
3094
1997
$485
Initiation Fees Going Up On 2/1/2025. Buy Now Before The Increase! COLDWELL BANKER REALTY.
Pended $629,000
818 Oak Pond Dr, Osprey, FL 34229
Reduced By $30,000
1975
1996
$318
Bay Oaks Estates - Enjoy the ideal location of this home: close to the famous Legacy Biking Trail connecting Venice to Sarasota, Nokomis Beach, Historic Spanish Point, Oscar Scherer State Park and Pineview School for the gifted. SUNSET REALTY.
Home For Sale $1,199,000
120 Lookout Point Dr, Osprey, FL 34229
Reduced By $76,000
2925
1985
$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 $729,000
819 Shadow Bay Way, Osprey, FL 34229
2145
$340
Bedroom closet type is walk-in closet, primary bedroom. PREMIER SOTHEBYS INTL REALTY.
Home For Sale $3,275,000
135 Tina Island Dr, Osprey, FL 34229
2011
$1,273
YOU CAN ENJOY THE DEEP WATER WITH NO BRIDGES TO THE BAY and much more. RE/MAX PALM REALTY OF VENICE.
Home For Sale $959,000
21 Bayhead Ln, Osprey, FL 34229
2216
$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 $359,000
214 Patterson Ave, Osprey, FL 34229
Reduced By $21,000
1092
2004
$329
Live the Florida oasis lifestyle you’ve always dreamed of! RE/MAX ALLIANCE GROUP.
Home For Sale $4,195,000
854 Macewen Dr, Osprey, FL 34229
Reduced By $300,000
9081
2003
$462
Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR** GENEROUS PROPERTY.
Home For Sale $775,000
524 Oak Bay Dr, Osprey, FL 34229
Reduced By $24,000
2767
1998
$280
HOA fee is only $270.00 annually. New roof in 2019! COLDWELL BANKER REALTY.
Home For Sale $875,000
320 Gaugin Dr, Osprey, FL 34229
Reduced By $84,000
1402
1966
$624
Call today to see this great home! KW COASTAL LIVING.
Home For Sale $951,000
650 Crane Prairie Way, Osprey, FL 34229
3183
2005
$299
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 $550,000
328 Woods Point Rd, Osprey, FL 34229
Reduced By $65,000
1862
$295
Come and visit this maintenance-free oasis today! COMPASS FLORIDA LLC.
Pended $673,000
610 Pine Ranch East Rd, Osprey, FL 34229
Reduced By $26,000
2431
1995
$277
(Some Furniture available outside of contract) COLDWELL BANKER REALTY.
Home For Sale $1,649,000
325 Osprey Point Dr, Osprey, FL 34229
Reduced By $41,000
3905
1986
$422
**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** GENEROUS PROPERTY.
Home For Sale $3,775,000
5 N Casey Key Rd, Osprey, FL 34229
Reduced By $400,000
2380
1969
$1,586
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
13 Bayhead Ln, Osprey, FL 34229
2310
2001
$400
A Golf equity or Social membership is required with a real estate purchase. MICHAEL SAUNDERS & COMPANY.
Home For Sale $1,795,000
909 Macewen Dr, Osprey, FL 34229
4241
1991
$423
Home For Sale $3,995,000
412 Cezanne Dr, Osprey, FL 34229
Reduced By $255,000
4535
$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 $849,000
1768 S Creek Ln, Osprey, FL 34229
Reduced By $81,000
2837
Don't miss out on this Awesome home - Schedule your viewing today! EXP REALTY LLC.
Home For Sale $1,595,000
360 N Point Rd, Osprey, FL 34229
2913
2023
$548
One or more photo(s) has been virtually staged. **ENJOY THE 3D VIRTUAL TOUR** GENEROUS PROPERTY.
Pended $950,000
124 Tina Island Dr, Osprey, FL 34229
Reduced By $225,000
2112
$450
The property did not have any flood damage . COLDWELL BANKER SARASOTA CENT..
Pended $649,900
593 Crane Prairie Way, Osprey, FL 34229
Reduced By $79,100
2340
$278
Centrally located in Osprey within a short distance to beaches, restaurants & shopping. COLDWELL BANKER SARASOTA CENT..
Home For Sale $1,500,000
1108 Bayhead Ln, Osprey, FL 34229
3541
$424
Bring your clothes & live happily in this incredibly comforting home. Cheers & welcome home! ILLUSTRATED PROPERTIES LLC (CO.
Home For Sale $399,900
329 Bay Vista Ave, Osprey, FL 34229
1346
1963
$297
Bay Acres - Electric bill for 2023 was $636.28. HORIZON REALTY INTERNATIONAL.
Home For Sale $1,695,000
402 Walls Way, Osprey, FL 34229
Reduced By $200,000
3464
2014
$489
Pended $525,000
629 Oak Bay Dr, Osprey, FL 34229
Reduced By $75,000
1867
$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. KW COASTAL LIVING III.
Pended $995,000
1200 Mallard Marsh Dr, Osprey, FL 34229
Reduced By $175,000
2928
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.
Home For Sale $5,500,000
608 N Casey Key Rd, Osprey, FL 34229
Reduced By $1,000,000
3086
1916
$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
97 Sugar Mill Dr, Osprey, FL 34229
6
4885
$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.
Pended $289,000
38 Old Venice Rd, Osprey, FL 34229
Reduced By $86,000
1
1163
1960
$248
See this one for yourself; book a showing today. CHARLES RUTENBERG REALTY INC.
Home For Sale $4,500,000
426 N Casey Key Rd, Osprey, FL 34229
1876
1992
$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 $340,000
206 Patterson Ave, Osprey, FL 34229
Reduced By $49,000
1242
$274
New Construction and is scheduled to be done Mid to late Summer. EXIT GULF COAST REALTY.
202 Patterson Ave, Osprey, FL 34229
Construction started and expected to be completed in mid to late Summer. EXIT GULF COAST REALTY.
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