Sarasota's Premier Homes
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Osprey

One of the most popular communities provided by Michael Graf

Osprey

About Osprey

<p>Osprey is a tranquil coastal community tucked between Sarasota and Venice, offering a perfect blend of natural beauty and upscale living. Known for its peaceful vibe, top-rated schools, and access to the Intracoastal Waterway, Osprey is ideal for nature lovers and boaters. Residents enjoy quick access to parks like Oscar Scherer State Park, waterfront dining, and nearby beaches. With elegant neighborhoods, quiet streets, and a strong sense of community, Osprey is a hidden gem on Florida’s Gulf Coast.</p>
One of the most popular communities provided by Michael Graf
154
# of Listings
3
Avg # of Bedrooms
$403
Avg. $ / Sq.Ft.
$946,311
Med. List Price

Browse Osprey Real Estate Listings

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

5 Properties Found. Page 1 of 1.

Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one-plus-acre estate, with 107 feet of pristine gulf frontage, a walkable sandy beach, on a private road with security offering unparalleled privacy, is your personal slice of heaven. Surrounded by majestic live oaks, this property is a rare gem that embodies the timeless beauty of Old Florida living, offering a tranquil retreat with direct gulf-to-bay access. The three-bedroom, three-bath home exudes Mediterranean coastal charm and invites you to embrace the serenity of coastal life. With an expansive living room, formal dining room, country kitchen and an office, the home effortlessly combines comfort and style. Imagine cozying up with a cup of coffee in front of the fireplace in the primary bedroom as the first rays of dawn light up the sky over the Intracoastal Waterway, casting a soft glow on the water. As evening falls, step out and witness breathtaking sunsets over the gulf, painting the sky in hues of gold and pink, an enchanting end to every day. This completely fenced estate also offers a two-car attached garage and an additional three-car detached, air-conditioned garage, a dream for car enthusiasts who appreciate form and function. For boating lovers, a rare boathouse with a deck overlooking Little Sarasota Bay, two docks, one with a 7,500-pound lift, and a seawall, make it the ideal home for a waterfront lifestyle. Boat access to the gulf is a short five-minute ride through Midnight Pass. With direct access to the gulf, this property lets you indulge in the best of both worlds, an exclusive, private oasis and the beauty of the sparkling blue waters just near your door. On the exclusive north end of Casey Key, this estate offers seclusion and serenity, yet just five minutes from restaurants, Publix, CVS, 10 minutes to the City of Venice and 15 minutes to Sarasota. Commercial and private air travel is readily available. Don't miss your chance to live in one of Florida’s most desirable locations. With stunning sunsets, playful dolphins and soothing sound of waves as part of your everyday life, this is more than a home, it's a sanctuary. Experience the ultimate coastal lifestyle and make this paradise yours.
#N6137711

OSPREY

1049 N CASEY KEY ROAD

3 Beds

3 Baths

2,582 Sq.Ft.

$4,750,000

MLS#: N6137711

One or more photo(s) has been virtually staged. **NEWLY RENOVATED, SPACIOUS, 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 Beds + 4/2 Baths + Office/Library + Home Theater + Game Room w/ Wet Bar, Loft, Balcony, etc. and even includes highly coveted, oversized and split 4-CAR GARAGE(s). This MOVE-IN READY home has been tastefully updated and is ideal for indoor and outdoor entertaining! The elegant first level primary bedroom suite features high ceilings, multiple walk-in closets, garden tub, large custom walk-in shower and an adjacent nursery/fitness/den area. The sprawling, gourmet kitchen entails a generous island and counter seating area, premium stainless steel appliances, granite counters, solid wood cabinets, walk-in pantry and more. The upstairs loft leads to two vast bedroom suites, theater room and screened terrace/balcony. Enjoy the utmost in Florida outdoor living with a Heated Pool & Spa with Fire features and a large screened lanai with Outdoor Kitchen and seating areas while overlooking the serene interior, Heron Golf Course. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR**
#A4627698

OSPREY

854 MACEWEN DRIVE

4 Beds

4 Baths

9,081 Sq.Ft.

$4,195,000

MLS#: A4627698

EXCEPTIONAL WATERFRONT RESIDENCE on the exclusive island of North Casey Key is a rare opportunity to own a piece of coastal Florida. Nestled in the sought-after Palmer neighborhood, this home has been lovingly maintained by the same discerning owners since 1999—a testament to the pride, care, and attention poured into every detail over the years. Set on an expansive 0.68-acre lot with 131 feet of Sarasota Bay frontage with two deeded private beach access points, the property is enveloped in lush tropical landscaping and exudes timeless Old Florida charm. The interior showcases a traditional layout with formal living and dining rooms, a spacious family room, private office, bonus room, a serene first-floor master suite, and three additional guest bedrooms. Designed for both everyday comfort and gracious entertaining, the home also features a screened-in pool and a covered boathouse accommodating vessels over 25 feet. Enjoy captivating views of the bay with breathtaking sunrises and sunsets from your own backyard oasis. Meticulously updated over time, the home includes a metal roof, 2 News AC's, PGT impact windows, a steam room, re-piping, and more—all reflecting the owners’ commitment to quality and preservation. Located just 15 miles south of downtown Sarasota and moments to Pineview (#1 Ranked School in Florida), nature parks, the Legacy Trail, this property blends unmatched privacy with access to world-class amenities. A truly special home....ready to begin its next chapter.
#A4650216

OSPREY

1042 N CASEY KEY ROAD

4 Beds

4 Baths

4,781 Sq.Ft.

$3,750,000

MLS#: A4650216

Premier Waterfront Opportunity in The Oaks Bayside This grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers sweeping views of Little Sarasota Bay and exceptional potential. With its expansive floor plan across three levels, soaring ceilings, and dramatic architectural features, this residence was built to impress—and now invites a new owner to make it their own. The ground floor has been thoughtfully prepared for renovation, providing a blank canvas to bring your vision to life. Whether you imagine a guest or in-law suite, a luxury garage with a gaming lounge, a showcase for your fishing gear, or a green room for potting plants—the possibilities are endless. A private dock awaits your custom design, offering direct access to the open bay and Gulf of Mexico. Just steps from the home, the community dock—exclusively for Oaks Bayside residents—adds even more coastal charm. Fish, launch a kayak, relax and watch the sunset, or gather with neighbors in this serene waterfront setting. Ownership includes mandatory membership in The Oaks Club, unlocking an array of world-class amenities. Set across more than 1,000 acres, the club features two private 18-hole championship golf courses, 14 Har-Tru tennis courts, a croquet lawn, a junior Olympic swimming pool, state-of-the-art fitness center, and a stunning 34,000-square-foot Georgian-style clubhouse. A guest lodge and vibrant year-round social calendar complete this private country club experience. You're not just creating a home—you're curating a luxury lifestyle in one of Florida’s most prestigious coastal communities. This exceptional property is ready for your private tour at your convenience.
#O6305818

OSPREY

112 OSPREY POINT DRIVE

4 Beds

5 Baths

8,635 Sq.Ft.

$3,705,000

MLS#: O6305818

Sited at the end of a quiet cul-de-sac behind the gates of the prestigious Oaks Clubside in Osprey, Florida, this stately traditional custom estate offers refined living in one of Sarasota County’s most exclusive communities. Perfectly positioned on over three-quarters of an acre, the residence boasts serene preserve and fairway views, capturing the essence of Florida luxury living. Inside, discover graciously sized rooms, soaring ceilings, and abundant natural light that fills every space. The formal living room with gas fireplace and the formal dining room provide elegant spaces for entertaining. The open-concept kitchen and family room are the heart of the home, ideal for casual gatherings and everyday comfort. A large kitchen offers a generous walk-in pantry, plentiful storage, and a seamless flow into the family room and outdoor spaces. The primary suite is located on the main floor, offering a tranquil retreat with a spa-like bathroom, separate dressing room, and expansive walk-in closet. An office with fireplace is also on the main level, perfect for work-from-home privacy. Upstairs, two additional bedrooms and a bonus room provide a private haven for guests or multi-generational living. Step outside to the screened and covered outdoor living area, where a summer kitchen, cabana with full bath, and lush landscaping invite indoor-outdoor living year-round. It’s an entertainer’s dream, ideal for both intimate gatherings and grand events. Key features include wind-rated impact windows, new tile roof to be installed with a transferable 20-year workmanship warranty, $800,000+ in updates under current ownership, and situated on an oversized lot with ultimate privacy. As part of The Oaks Club, enjoy world-class amenities including two championship golf courses, 12 Har-Tru tennis courts, pickleball, croquet, a state-of-the-art WellFit Center, and exceptional dining at The Oaks Room, The Overlook, and The Tavern. This is more than a home—it's a lifestyle. Experience the timeless elegance, thoughtful design, and unmatched amenities of The Oaks Club in this remarkable estate.
#A4656464

OSPREY

550 DOVE POINTE

4 Beds

5 Baths

7,842 Sq.Ft.

$3,300,000

MLS#: A4656464

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