Osprey Vacation Homes for Sale

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608 CASEY KEY ROAD, OSPREY, Florida 34229

Single Family Residence For Sale

Rarely available Gulf to Bay estate size property with 175 feet of Gulf frontage, 175 feet of Bay frontage and encompassing 1.5 acres is located on the exclusive North End of Casey Key. Casey Key, distinguished for its absence of high-rises, traffic congestion, and private beaches, is one of the most esteemed barrier islands of Sarasota and Florida’s Gulf Coast.
$6,500,000
5Bedroom(s)
3Bathroom(s)
4,375Sqft
AYERS AND ASSOCIATES REAL ESTATE

614 BAYSHORE DRIVE, OSPREY, Florida 34229

Single Family Residence For Sale

Welcome to this exclusive 2024 waterfront estate by Pileggi Custom Homes—a boater's dream nestled on over half an acre with 116 feet of waterfront footage. This pinnacle of luxury offers showcase views of Little Sarasota Bay and Casey Key sunsets. Spanning over 2 floors, the home features 3 bedrooms, 4.
$5,350,000
3Bedroom(s)
4Bathroom(s)
6,347Sqft
KELLER WILLIAMS ON THE WATER S

426 CASEY KEY ROAD, OSPREY, Florida 34229

Single Family Residence For Sale

Gulf to Bay on North Casey Key – the perfect location! Panoramic views of Little Sarasota Bay to the east and a beachfront lot on the west. Original cypress tongue and groove ceilings and beautiful oak floors add warmth and nostalgia throughout the home. A nicely updated kitchen overlooks the pool and bay.
$4,500,000
3Bedroom(s)
2Bathroom(s)
3,114Sqft
PREMIER SOTHEBYS INTL REALTY

412 CEZANNE DRIVE, OSPREY, Florida 34229

Single Family Residence For Sale

Nestled in the serene and highly sought-after Sorrento Shores community, this exceptional and breathtaking property offers unparalleled waterfront living on over an acre of land (1.19 acres) along the tranquil South Creek. Featuring 144 feet of water frontage, the home is tucked away on a secluded drive, providing both privacy and stunning water views.
$4,250,000
4Bedroom(s)
4Bathroom(s)
4,924Sqft
CORNERSTONE R.E OF SW FL

503 VELASQUEZ DRIVE, OSPREY, Florida 34229

Single Family Residence For Sale

Welcome to 503 Velasquez Drive, your Osprey Oasis and waterfront estate located on Blackburn Bay of the Intracoastal Waterway. This property offers an unparalleled view in its prime location overlooking the Bay, with stunning sunsets and quiet early morning reflection over the heated pool.
$2,950,000
4Bedroom(s)
3Bathroom(s)
3,615Sqft
EXP REALTY LLC

140 CASEY KEY ROAD, OSPREY, Florida 34229

Single Family Residence For Sale

The price has been improved. rnDROP ANCHOR and stay forever in this 3 bedroom, 3.5 bath, intracoastal waterway home tucked away just enough to feel like you have your very own private oasis. You have deeded boat access with your own assigned boat slip where you may catch dolphins playing in the water before you take out your kayaks, jet skis, or the boat.
$2,600,000
3Bedroom(s)
3Bathroom(s)
2,773Sqft
LPT REALTY

324 KENSEY LANE, OSPREY, Florida 34229

Single Family Residence For Sale

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 spectacular sunsets. This gated waterfront gem has 3 bedrooms, 3 bathrooms, includes bonus room, office, and laundry closet.
$2,089,000
3Bedroom(s)
3Bathroom(s)
3,063Sqft
SARASOTA COAST REALTY INC

124 TINA ISLAND DRIVE, OSPREY, Florida 34229

Single Family Residence For Sale

This great waterfront location is in desirable Sorrento Shores with a new dock on a large private view canal. This 3 bedroom 2 bath split plan has a large living/dining area and a separate office space. The kitchen area has a separate seating area with a bay window overlooking the dock and canal. This property is ready for you to add your personal touches.
$1,125,000
3Bedroom(s)
2Bathroom(s)
3,143Sqft
COLDWELL BANKER SARASOTA CENT.

14021 BELLAGIO WAY Unit#204, OSPREY, Florida 34229

Condominium For Sale

Million Dollar Water Views from Every Major Room. This is your chance to buy one of the best units in this great development. Updated to the highest standard. Located on the first floor, which gives easy access to Pool/Spa & Grille/Smoker area. Impressive views of the Bay & Marina. Elevator to your own front entry & into an impeccable Condo.
$1,100,000
3Bedroom(s)
3Bathroom(s)
2,689Sqft
ALLISON JAMES ESTATES & HOMES

434 SHORE DRIVE, OSPREY, Florida 34229

Single Family Residence For Sale

One or more photo(s) has been virtually staged. Experience the beauty of waterfront living in the desirable neighborhood of Sorrento Shores, tucked away west of the Trail. This home is a dream for boaters, with no fixed bridges and easy access to the Gulf of Mexico.
$1,025,000
3Bedroom(s)
3Bathroom(s)
4,350Sqft
ENGEL + VOELKERS SARASOTA

14021 BELLAGIO WAY Unit#311, OSPREY, Florida 34229

Condominium For Sale

Immerse yourself in the incredible views of Little Sarasota Bay and the Intracoastal waterway from this 3rd floor beautiful and spacious condominium. This upgraded end unit features 3 ensuite bedrooms, plus den, half bath and interior laundry room. The kitchen is a cook's delight with premium granite, upgraded wood cabinets and stainless steel appliances.
$995,000
3Bedroom(s)
3Bathroom(s)
2,490Sqft
GULF TO BAY SOTHEBY'S INTERNAT

510 OLD VENICE ROAD, OSPREY, Florida 34229

Single Family Residence For Sale

One or more photo(s) has been virtually staged. This is the one you've been waiting for! Nestled on approximately 3 acres, this cherished family estate, spanning generations, awaits its next chapter. Situated opposite the esteemed Pine View School for the Gifted, ranked #1 High School in Florida and #18 High School nationally, this unique parcel blends country charm with coastal allure.
$962,500
3Bedroom(s)
2Bathroom(s)
3,276Sqft
FINE PROPERTIES
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