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

5 CASEY KEY ROAD, OSPREY, Florida 34229

Single Family Residence For Sale

This mid-century modern luxury property includes approximately 100' of water frontage on the Gulf of Mexico with stunning unobstructed views and over half of an acre lot. Relax in the sun on the patio or take in the gorgeous sunsets from almost every room. This Gulf front beach home is located on one of the most serene and exclusive barrier islands on Florida's west coast.
$3,990,000
4Bedroom(s)
3Bathroom(s)
3,515Sqft
CHARLES RUTENBERG REALTY INC

140 CASEY KEY ROAD, OSPREY, Florida 34229

Single Family Residence For Sale

DROP 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.
$2,999,000
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.
$2,099,000
3Bedroom(s)
3Bathroom(s)
3,063Sqft
SARASOTA COAST REALTY INC

3933 WAYPOINT AVENUE, OSPREY, Florida 34229

Single Family Residence For Sale

Welcome to the epitome of luxurious and hassle-free living in the coveted community of Bayside, a gated waterfront community of 49 homes on Little Sarasota Bay. This immaculate, like-new home, built in 2016 on an oversized lot with serene, private preserve views, has been meticulously maintained and offers a host of premium features that discerning buyers will appreciate.
$1,220,000
3Bedroom(s)
3Bathroom(s)
3,424Sqft
PREMIER SOTHEBYS INTL REALTY

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

236 HIDDEN BAY DRIVE Unit#504, OSPREY, Florida 34229

Condominium For Sale

Welcome to Hidden Bay. This stunning 3bd/ 3br corner unit condo offers unimpeded views of Casey Key and Little Sarasota Bay from many rooms. The large foyer welcomes guests into the home and boasts a completely remodeled 5th floor unit featuring high-end finishes throughout, including bamboo flooring, quartz countertops, solid wood cabinetry, and an induction cooktop.
$975,000
3Bedroom(s)
3Bathroom(s)
2,394Sqft
RE/MAX ALLIANCE GROUP

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

14041 BELLAGIO WAY Unit#313, OSPREY, Florida 34229

Condominium For Sale

Welcome to the highly desirable community of The Villas at Osprey Harbor! This light and bright end unit with a private entrance is loaded with recent, tasteful updates including a fully renovated kitchen in 2022 with high end rift cut white oak custom cabinetry and a quartz breakfast bar, induction stove, updated baths, 24-by-24 porcelain tile, lighting, fans, fresh paint throughout, a coffee bar
$899,000
3Bedroom(s)
2Bathroom(s)
2,390Sqft
PREMIER SOTHEBYS INTL REALTY

280 HIDDEN BAY DRIVE Unit#302, OSPREY, Florida 34229

Condominium For Sale

One or more photo(s) has been virtually staged. Under Construction. Photos are for demonstration purposes only and may not reflect the actual unit or floor plan.
$832,750
3Bedroom(s)
2Bathroom(s)
2,241Sqft
PREMIER SOTHEBYS INTL REALTY

280 HIDDEN BAY DRIVE Unit#204, OSPREY, Florida 34229

Condominium For Sale

One or more photo(s) has been virtually staged. Under Construction. Photos are for demonstration purposes only and may not reflect the actual unit or floor plan. Centrally located between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay, a gated, 12-acre resort-style community located on the water's edge of Little Sarasota Bay in Osprey, Florida.
$822,250
3Bedroom(s)
2Bathroom(s)
2,434Sqft
PREMIER SOTHEBYS INTL REALTY
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