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Osprey Homes For Sale

Osprey real estate, located just south of Sarasota, provides a tranquil and welcomed alternative to popular urban centers. Homes for sale in Osprey were carefully constructed with the intention of maximizing quality of life for their residents, especially those who are passionate about the Florida outdoors. Complete with an incredible variety of architecture, design styles, and prices - Osprey real estate offers resort-style living at a very reasonable cost. Call our Osprey Real Estate HOTLINE at 941.488.6644 for information on all current listings.

Osprey

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Photo of Listing #A4643654

1216 N Casey Key Road, OSPREY, FL
$10,750,000

Residential, Single Family Residence
  • 5 Beds
  • 8 Baths
  • 8,050 SQFT
  • 320 DOM
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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 Blackbur...

121 N Casey Key Road, OSPREY, FL
$7,100,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,096 SQFT
  • 109 DOM
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Newly Remodeled Gulf-front Mediterranean Villa On Casey Key Framed By The Pristine Natural Beauty Of North Casey Key, This Spanish Mediterranean Beachfront Estate Is Perfectly Positioned Along One Of Florida’s Most Exclusive Barrier Islands — An ...

730 Sarabay Road, OSPREY, FL
$5,495,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 6,308 SQFT
  • 63 DOM
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Premier Intracoastal Estate In Osprey 4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterfront Acres A Rare Opportunity To Own Two Acres Of Private Waterfront Property In Sarasota, 730 Sarabay Is A Convergence Of Residential Luxury And Unparalle...

101 Osprey Point Drive, OSPREY, FL
$5,000,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 5,087 SQFT
  • 126 DOM
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A Grand Estate Where Timeless Design Meets Lakefront Tranquility, 101 Osprey Point Drive Offers Refined Living Within The Private Gates Of The Oaks Bayside. Designed By Architect Bo Macewen, This One-of-a-kind Home Spans More Than 5,000 Square Fee...

854 Macewen Drive, OSPREY, FL
$3,950,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 9,081 SQFT
  • 95 DOM
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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 Upd...

1042 N Casey Key Road, OSPREY, FL
$3,750,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,781 SQFT
  • 40 DOM
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If Your Dream Is To Create A Place Where Generations Can Gather, Relax, And Make Lasting Memories, This Casey Key Estate Is Ready To Welcome You Home. Set On 0.68 Acres With 131 Feet Of Sarasota Bay Frontage, This 4 Bed 4.5 Bath Retreat Offers Roo...

Photo of Listing #A4665474

135 Tina Island Drive, OSPREY, FL
$3,300,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 2,572 SQFT
  • 126 DOM
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Retreat To Paradise In This Stunning Waterfront Home, Built New In 2011, In Highly Sought-after Sorrento Shores, Osprey. Perfectly Situated On 210 Feet Of Wide Canal Frontage, This Residence Offers Deep Water Access With No Bridges To The Bay—a Dr...

Photo of Listing #N6141722

479 South Creek Drive, OSPREY, FL
$2,795,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,261 SQFT
  • 51 DOM
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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 B...

Photo of Listing #A4644125

236 Saint James Park, OSPREY, FL
$2,700,000

Residential, Single Family Residence
  • 6 Beds
  • 7 Baths
  • 6,246 SQFT
  • 300 DOM
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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 Soug...

49 Osprey Point Drive, OSPREY, FL
$2,595,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,953 SQFT
  • 69 DOM
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Nestled In The Prestigious Gated Enclave Of The Oaks Bayside In Sarasota, This Sedona-inspired Retreat Was Recently Updated From Wall To Wall Creating A Like Brand New Home. The Estate Seamlessly Blends Modern Luxury, Comfort, And Serenity. With A...

Photo of Listing #A4659276

852 Macewen Drive, OSPREY, FL
$2,495,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 4,519 SQFT
  • 185 DOM
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**charming And Private, Golf Course Estate** Is Located Behind The Secure Gates Of The Highly Sought After Oaks Country Club Community And Offers A Lovely, Golf Course View Of The 17th Fairway Of The Interior, Heron Golf Course. This Spacious, Li...

About Osprey Real Estate

Osprey homes for sale comprise a refreshing combination of various property types, from luxury homes and architectural wonders along the Intracoastal Waterway, to quaint mobile home parks just a few blocks away. A stroll down a street in Osprey reveals a gorgeous mixture of Spanish Colonial revival style, modern Mediterranean-inspired, and Florida ranch-style homes colored with neutral and muted pastel exteriors.

The Osprey community sprawls six square miles of the Gulf of Mexico shoreline, charmed by several nearby canals, creeks, inlets, lakes, and rivers. Most Osprey homes for sale are beautifully bordered by an extensive blend of small palm trees, pines, and flatwoods - in addition to backyard swimming pools.

Home buyers in search of reasonably priced waterfront properties need look no further than Osprey real estate. With a median price of around $600,000, there's ample opportunity in Osprey for various homebuyers, regardless of price range and design style. Whether you're interested in exploring The Oaks - one of the Osprey community's most reputable Country Clubs - or the gated mobile home community of South Creek, you're bound to find a match for your lifestyle in the Osprey area.



Community Amenities

Depending on the neighborhood, Osprey real estate often features close proximity to golf courses, tennis courts, club pools, spas, and state-of-the-art fitness facilities. Osprey is also uniquely central, featuring easy access to plenty of dining, shopping, recreational opportunities, and schools.

Dining & Shopping

Whether you're in the mood for a prestigious seafood dinner or a sports bar experience, you won't be disapppointed with the variety of dining options located near sought-after Osprey real estate. Nearby highly rated restaurants include:

  • Max's Table
  • Bologna Cafe
  • Mad Moe's Sports Pub & Grill
  • By The Bay Bistro

If you're in the mood for some retail therapy, Pelican Plaza Shopping Center, Westfield Sarasota Square, and Plaza at Palmer Ranch are less than a 10 minute drive from the heart of Osprey. A little closer to home, Osprey residents can also explore the wares available at the Southbay Shopping Center.

Outdoor Adventures

Just 5 minutes from the heart of Osprey is Oscar Scherer State Park - a perfect spot for hiking, jogging, and bicycling. A paradise for bird-watchers, this park is home to many Ospreys, Bald Eagles, Great Herons, and Little Blue Herons.

Historic Spanish Point is a treasured attraction in Osprey, with its 30+ acres of environmental wonders and expansive museum. This area was the 1st site in all of Sarasota County to be included in the National Register of Historic Places.

If canoeing and kayaking are more your style, why not take a ride along South Creek - a black water stream that flows directly to the Gulf of Mexico.

Excellent Schools

The prestigious Pine View School for the Gifted is just 5 minutes from the heart of Osprey, offering public, college-prepatory education to Osprey students. Other esteemed local schooling choices include:

  • Laurel Nokomis School
  • Gulf Gate Elementary
  • Brookside Middle School
  • Venice Senior High School
  • Riverview High School

Call us today at 941-488-6644

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on January 22nd, 2026 at 10:52pm EST.