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Homes for Sale in Osprey, FL with 5-Bedrooms

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  • /73

    $2,495,000

    • 5 Beds
    • 5.5 Baths
    • 4,261 Sq Ft

    479 S Creek Dr, Osprey, FL 34229

    Positioned on South Creek just off the Intracoastal Waterway with beautiful views and over 130 FEET of WATERFRONT, this 5-bedroom, 5.5-bath coastal estate offers over 4,261 square feet of refined waterfront living anchored by a truly spectacular backyard oasis. The heated saltwater PebbleTec pool, featuring an impressive 10-FOOT DEPTH, is paired with a separate spa and framed by elegant

    Michelle Hupp KELLER WILLIAMS ISLAND LIFE REAL ESTATE

    479 S Creek Dr, Osprey, FL 34229
  • /70

    $2,249,900

    • 5 Beds
    • 3.5 Baths
    • 3,236 Sq Ft

    180 Lookout Point Dr, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is an extraordinary

    Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

    180 Lookout Point Dr, Osprey, FL 34229
  • /88

    $650,000

    • 5 Beds
    • 2.5 Baths
    • 2,746 Sq Ft

    571 Pine Ranch Rd E, Osprey, FL 34229

    One of the largest homes in Bay Oaks Estates, with the second-largest floor plan in the community, this 5-bedroom, 2.5-bath single-story pool retreat delivers the best of indoor-outdoor Florida living with flexible spaces for guests, work, and play. Curb appeal pops with a brick paver circular drive, lush, well-established landscaping highlighted by a mature magnolia and fragrant gardenias, and a

    Christiana Kopetzky MICHAEL SAUNDERS & COMPANY

    571 Pine Ranch Rd E, Osprey, FL 34229
  • /82

    $1,250,000

    • 5 Beds
    • 3.5 Baths
    • 3,481 Sq Ft

    296 Pine Ranch Trail, Osprey, FL 34229

    **THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of a

    Deborah Frederick ASHTON LAKES REALTY INC

    296 Pine Ranch Trail, Osprey, FL 34229
  • /88

    $2,700,000

    • 6 Beds
    • 6.5 Baths
    • 6,246 Sq Ft

    236 Saint James Park, Osprey, FL 34229

    Tucked away in a quiet cul-de-sac on a sprawling double lot beneath majestic oaks, this nearly 5,000 sq ft timeless 2-story residence blends classic elegance with modern luxury. Perfectly positioned on the first hole of one of Sarasota’s most sought-after golf courses, the home showcases soaring 11-ft ceilings, gleaming marble floors, and dazzling crystal chandeliers. A Louis XVI fireplace

    Karin Watt MICHAEL SAUNDERS & COMPANY

    236 Saint James Park, Osprey, FL 34229
  • /60

    $10,750,000

    • 5 Beds
    • 8 Baths
    • 8,050 Sq Ft

    1216 N Casey Key Rd, Osprey, FL 34229

    This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family

    Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1216 N Casey Key Rd, Osprey, FL 34229

Home Trends in Osprey, FL

Housing Trends

Median Sale Price
$667,500
Median Single Family Sale Price
$850,000
Median Townhouse Sale Price
$457,000
Median 2 Bedroom Sale Price
$295,000
Median 1 Bedroom Sale Price
$185,000
Average Price Per Sq Ft
$377
Number of Homes for Sale
139
Last 12 months Home Sales
196
Months of Supply
8.50
Median List Price
$765,000
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-13%
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