Skip to Content Skip to Navigation Skip to Dashboard Skip to Search

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.


Search Osprey Real Estate Listings

Map View New Construction Save this Search
Sort listings by:Price, Highest First

1544 North Casey Key Road, OSPREY, FL

Residential, Single Family Residence
  • 6 Beds
  • 8 Baths
  • 6,997 SQFT
  • 203 DOM
View Details & More Photos Save

World Class Beach Front Estate Located On Casey Key, One Of The Most Private And Exclusive Barrier Islands Of Sarasota And Florida’s Gulf Coast. Built To Entertain Guests From Around The World, This Magnificent Six-bedroom Estate Sits On 2.5 Acres...

Photo of Listing #N6123485

476 North Casey Key Road, OSPREY, FL

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 4,740 SQFT
  • 109 DOM
View Details & More Photos Save

Dramatic Contemporary Architectural Masterpiece Completed Fall Of 2021 On The Exclusive & Private North End Of Casey Key With Deeded Gulf Access. Designed By Award Winning Architect Mark Sulatana & Constructed By Sarasota’s Premier Luxury Builder ...

Photo of Listing #A4552859

608 North Casey Key Road, OSPREY, FL

Residential, Single Family Residence
  • 5 Beds
  • 3 Baths
  • 3,086 SQFT
  • 81 DOM
View Details & More Photos Save

Opportunities Are Endless With This Extremely Unique 1.5 Acre Property Situated On North Casey Key Road. Watch The Sunrise From Your Private 175' Frontage On Little Sarasota Bay (with Permits For Docks) And Watch The Sunset From Your Private 175' ...

Photo of Listing #A4554720 OPEN HOUSE

854 Macewen Drive, OSPREY, FL

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 9,081 SQFT
  • 51 DOM
View Details & More Photos Save

**spacious, Luxurious And Beautifully Renovated, Golf Course Estate** Boasts Over 9,000sf And Is Situated On A Prominent, Private Cul De Sac Lot Of Over 3/4 Acres. Expansive Room Abounds In This Light And Bright Open Floorplan Consisting Of 4 Bed...

Photo of Listing #N6124661

133 West Bay Street, OSPREY, FL

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,168 SQFT
  • 23 DOM
View Details & More Photos Save

Extremely Special, Half Acre Bayfront Family Compound Located In Osprey Village-spanish Point With Four Tastefully Updated Residences, And The Fastest Growing “walking Bayfront Community” In Sarasota County! 100 Feet On Little Sarasota Bay With Pi...

871 Macewen Drive, OSPREY, FL

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,168 SQFT
  • 68 DOM
View Details & More Photos Save

Sited On Arguably One Of The Best Lots In The Oaks Club, This Beautifully Updated Georgian-style Home And Guest House Blend Perfectly With The Surrounding Landscape To Deliver Both Privacy And Stunning Golf Course Views Of The Heron Course’s 13th ...

Photo of Listing #A4546275

340 Osprey Point Dr, OSPREY, FL

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,001 SQFT
  • 123 DOM
View Details & More Photos Save

This Grand Estate Is Just As One Might Expect Tucked Behind The Gates Of The Oaks Bayside. Set Back From The Street And Surrounded By Lush Landscaping Which Includes Mature Oak Trees, Tropical Plants, And Beautiful Shrubs. The Driveway Is Made U...

370 Sugar Mill Drive, OSPREY, FL

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,783 SQFT
  • 101 DOM
View Details & More Photos Save

This 5 Bedroom, 5.5 Bath Home, Custom Built By Baron, Offers Over 4,700 Square Feet Of The Finest Living Area You’ll Find In The Oaks Bayside. Surrounded By Mature Landscaping, And Backing To Historic Spanish Point Preserve, This Home Enjoys A Pea...

324 Kensey Lane, OSPREY, FL

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 2,483 SQFT
  • 126 DOM
View Details & More Photos Save

Rare Opportunity To Own An Exceptional Waterfront Property And Tropical Oasis On .57 Acre Lot On A Wide Portion Of Little Sarasota Bay. Bayview Cottage Is The Original Florida Coastal Cottage Lifestyle Which Showcases Magnificent Water Views And S...

Photo of Listing #A4548857

628 North Macewen Drive, OSPREY, FL

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,486 SQFT
  • 93 DOM
View Details & More Photos Save

**beautifully Updated Golf Course Estate** This Ideal, Single-story Home Features 4 Beds + 4.5 Baths + 1 Office + 1 Den/bonus Room + 3-car Oversized Garage. With Its Light And Bright Open Floorplan, Walls Of Windows And High Ceilings Throughout, ...

Photo of Listing #A4543207

465 East Macewen Drive, OSPREY, FL

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,357 SQFT
  • 196 DOM
View Details & More Photos Save

Welcome To 465 E Macewen Drive, A Luxurious Estate Nestled Within The Sought After Oaks Community In Osprey, Florida. This Stunning Property Offers The Ultimate In Opulence And Elegance. As You Approach The Home, You'll Be Struck By Its Grand Fac...

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

^ Back to: Osprey Real Estate

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 February 7th, 2023 at 10:19pm EST.