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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

146

# of Listings

3

Avg # of Bedrooms

$404

Avg. $ / Sq.Ft.

$981,992

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

146 Properties Found. Page 1 of 10.

Nestled on a quiet street in the highly sought-after Rivendell community, this former Arthur Rutenberg model home features 4 bedrooms, 3 full baths, a den, and 2 versatile flex rooms, offering tranquil views of the pond and surrounding preserve. Framed by lush landscaping, the property features an oversized pool with a generously sized spa and ambient lighting, perfect for evening relaxation.
Inside, the wide, open floor plan boasts soaring ceilings and abundant natural light, creating an airy and uplifting atmosphere. Multiple living areas flow seamlessly into a spacious kitchen and family room, all opening to a covered lanai ideal for everyday living and entertaining. Just across the street, residents can enjoy the nearby Crescent Park and Playground.
The home includes a 2-car garage with an adjacent flex room that can easily be converted into a third garage bay or used as an exercise room, offering added functionality and storage. A rear room, currently used as an office with a built-in desk, offers added flexibility, ideal as a home office, study area, guest room, or multigenerational living space. It also features sliding glass doors that lead to a covered outdoor nook overlooking the lake, complete with a bar area, under-counter refrigerator, and sink.
This well-maintained residence has seen thoughtful updates over the years, including a NEWER ROOF (2017), HURRICANE SHUTTERS, SCREEN & PANELS FOR ALL OPENINGS, GARAGE DOOR (2019), PAVER DRIVEWAY (2022), a 5-ton A/C unit (2019), and a 2.5-ton A/C unit (2018) and newer appliances. Move-in ready with solid fundamentals, it also offers opportunities for personalization over time.
Rivendell is one of Sarasota County’s most cherished communities, spanning over 400 acres of protected nature preserves with scenic walking and biking trails, a heated community pool, and a peaceful, park-like atmosphere. Residents enjoy easy access to Oscar Scherer State Park (2 miles), the Legacy Trail (2.5 miles), Nokomis Beach (5 miles), and Siesta Key Beach (under 7 miles).
The home is also 1.4 miles (walkable and bikable) of Pine View School, ranked among the top public schools in the nation making this an exceptional location for families seeking elite educational opportunities.
With no CDD fees and a low HOA, this home offers an unmatched combination of comfort, location, and long-term value in one of Osprey’s most desirable neighborhoods. DON’T MISS THE FULL VIDEO WALK-THROUGH & THE 3D TOUR. CLICK EACH VIRTUAL TOUR LINK - TWO TOTAL.

OSPREY

766 SHADOW BAY WAY

4 Beds

3 Baths

4,457 Sq.Ft.

$998,000

MLS#: A4652814

Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel relaxed while enjoying the water views and fish jumping. There is nothing to do but move in and enjoy your new home. Taking the boat out is a breeze. Just lower it into the water and you are a short ride out to the intracoastal, the Venice Jetties and Midnight Pass. There are many great waterfront restaurants you can access by boat. If you happen to catch some fish while you are out enjoying the boat, there is a fish cleaning station on the dock. Located between Sarasota and Venice with easy access to I-75. Close to shopping, beaches, restaurants, Oscar Scherer Park and so much more.

OSPREY

120 VILLA DRIVE 120

2 Beds

2 Baths

1,855 Sq.Ft.

$550,000

MLS#: N6138441

New on site 2 days ago

Welcome to this well-maintained 2-bedroom, 2-bathroom ground-level condo in a highly convenient West of the Trail location.
As you walk through the gate, you’re greeted by a private courtyard that offers a quiet space to enjoy the outdoors. Inside, the condo features an open living area, a Florida room for extra relaxation space, and an outdoor patio surrounded by mature vegetation, offering added privacy and greenery in the backyard. A covered carport is included for convenience.
The community includes access to two swimming pools, tennis and pickleball courts, a small gym, kayak storage, and a clubhouse.
The location is ideal for enjoying the Florida lifestyle—just ½ mile to the Gulf, ¼ mile to Blackburn Point Park with a public boat launch, and only 6 miles to Nokomis Beach.

OSPREY

761 PINE RUN DRIVE 761

2 Beds

2 Baths

1,689 Sq.Ft.

$2,400

MLS#: A4663566

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 Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family and guests, this is a residence that inspire togetherness and embodies the art of waterfront living. Crafted with luxury finishes and modern conveniences, the property is built to exacting coastal standards with dramatic focus on stunning water views. Formal and casual spaces unite elegantly, including the living room with cypress beamed ceilings, overlooking the bay. A deluxe kitchen, wine, butler’s pantry and wet bar provide a canvas for culinary exploration and entertaining elegance. A grand media room for screening films provides the ideal place to unite music and culture. The expansive primary bedroom features a sitting room, lavish bath, dual closets, a breakfast nook and expansive views over the water. Three additional bedroom suites provide privacy, views and spacious accommodations. The fifth bedroom suite is equipped for a home gym, steam room and sauna. The office and library, next to the grand marble staircase, features leaded glass doors, hand crafted, built-in shelving, a coffered ceiling and beautiful views of the Gulf. Additional space for recreation and relaxation has been accomplished to make use of every inch of the estate. Arched hallways and French doors line the living room, open to the dazzling outdoor spaces and stone terraces lead to the infinity pool. Elevator access and garages for six vehicles add ultimate convenience. Enjoy boating from the deep-water dock which features a rare and grandfathered-in covered boat lift. North Casey Key is a haven of exclusivity and serenity, minutes from shopping, world-class golf, tennis and dining.

OSPREY

1216 N CASEY KEY ROAD

5 Beds

6 Baths

15,522 Sq.Ft.

$11,750,000

MLS#: A4643654

Property Type: Commercial Land with Existing Office Building
Property Size: 10 Acres

Discover this exceptional opportunity with over 900 feet of frontage on Tamiami Trail/US41 in Osprey, FL! This is one of the last substantial parcels available in Sarasota County with a Tamiami address. Positioned directly in the path of progress, this 10-acre parcel is ready for development with all entitlements in place.

Property Features:
Existing Office Building: 4,000 SF Freestanding Office Building with water, sewer, and electricity
Development Potential: Density for Assisted Living Facility/Memory Care at 9 units to an acre
Office Space Allowable: Up to 46,000 SF of office space
Prime Location: Directly across from the new Publix and adjacent to massive new developments, including shopping plazas, restaurants, apartments/condos, and single-family homes
Infrastructure: Electric, water, and sewer in place, making the property shovel-ready
Accessibility: Easy access to Tamiami Trail from both ends of the property with simple median cuts at Southbay Drive/Luminary Blvd
Strategic Positioning: Located at the northeast side of the intersection of Luminary Blvd and Tamiami Trail in Osprey, FL

OSPREY

505 LUMINARY BOULEVARD

None Beds

None Baths

4,000 Sq.Ft.

$7,499,000

MLS#: A4616676

A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless residence blends architectural elegance with waterfront living. Offering private access to the Intracoastal with a 100-foot dock (built in 2019), dual 12,000-pound lifts, water, and electric, this property is an ideal destination for boating enthusiasts. Offered fully furnished upon request. The front elevation is framed by a raised lawn with a stone wall, a paver driveway and manicured landscaping. As you approach the home, the travertine steps lead you to the new custom front door, where dramatic water views of the bay immediately greet you through expansive windows on opposite side of the home, creating a seamless connection to the Gulf and Bay. Inside, the main level is anchored by a breathtaking great room with coffered ceilings, custom millwork, and a wall of windows and doors that open to the terrace, creating an indoor/outdoor living space. A two-sided fireplace adds warmth and ambiance to the great room and the adjacent terrace. The interior showcases a multitude of upgrades, including updated Palecek lighting, and new porcelain tile flooring throughout. The 2020-renovated gourmet kitchen showcases bay views, Cambria Skara Brae quartz countertops, subway tile backsplash, custom white cabinetry and premium stainless-steel appliances. A bar area includes a wine refrigerator and ice maker, while a built-in pantry corridor connects seamlessly to the dining room. The dining area features built-in cabinetry and enjoys stunning bay views from the terrace. The formal living room, with its tranquil blue and cream tones, provides a lovely space to enjoy Gulf views while welcoming guests for dinner. The home offers two spacious primary suites, each with walk-in closets and luxurious en-suite baths, offering serene bay views and access to their private travertine terrace. Two guest suites and an upstairs office also enjoy remarkable water views. The staircase to the upper level reveals an oversized picture window framing the Gulf views. A three-floor elevator provides convenient access to all levels. The ground level features a spacious three-car garage with a dedicated golf cart space. Abundant space is designed to accommodate a variety of uses, and a new glass custom door offers light and access to the backyard and patio. Impact-rated windows and doors, along with a whole-house generator, provide peace of mind. Outside, the resort-style backyard features a refinished pool (with new tile and resurfacing), lush tropical landscaping, an expanded travertine patio and tiered terraces with custom stonework, columns, and stone floors. A rooftop deck offers panoramic views of the Gulf and Bay. Water enthusiasts will appreciate seamless access to the Intracoastal and Gulf, ideal for effortless boating. Additional upgrades include a newly painted roof tile, full exterior and interior repainting (2023), new fencing for added privacy, and two new entry doors (2025), completing the home’s thoughtful transformation. 144 N. Casey Key Road presents a rare opportunity to own a private waterfront estate offering luxury, seclusion and convenient access to Sarasota’s shopping, dining, beaches and parks.

OSPREY

144 N CASEY KEY ROAD

4 Beds

5 Baths

10,722 Sq.Ft.

$6,790,000

MLS#: A4660004

ELEVATED ABOVE FLOOD LEVEL WITH EXCEPTIONALLY LOW INSURANCE PREMIUMS !
Welcome to 622 Bayshore Drive - where coastal luxury meets modern sophistication on one of the most sought-after stretches of Little Sarasota Bay. Tucked away on a rare and expansive .78-acre gated estate, this custom-built, contemporary masterpiece offers 90 feet of pristine waterfront, unmatched privacy, and a lifestyle defined by serenity, style and seamless connection to the water. Designed for those who crave the extraordinary, this six-bedroom, five-bath residence is a showpiece of elevated design and quality craftsmanship, built just three years ago with the finest materials and storm-resilient features. Boaters will delight in the direct bay access just minutes from Midnight Pass and the open Gulf - a true water lover's paradise. Step through the grand entrance and into a world of light, space and unobstructed bay views. The soaring 14-foot bifold glass wall in the great room opens fully to a spectacular lanai, inviting indoor-outdoor living year-round. Imagine entertaining here – sunset cocktails by the saltwater pool and spa, laughter echoing across the water and every moment framed by nature's beauty. At the heart of the home lies a chef's dream kitchen, anchored by an oversized 7'X8' waterfall edge island and outfitted with top-tier Wolf, Cove, and Sub-Zero appliances. A walk-in pantry with second refrigerator/freezer ensures effortless hosting and everyday convenience. This home is as strong as it is stunning: constructed entirely of block and stucco, equipped with Category 5 impact-rated windows and doors, and elevated above flood level - a rare combination that provides peace of mind and impressively low insurance premiums. A whole-house generator ensures uninterrupted comfort. With its expansive yard, and panoramic water views, 622 Bayshore Drive is not just a home- it's a legacy property. Perfectly positioned between Sarasota and Venice, it offers the best of both worlds: quiet natural beauty with easy access to world-class dining, shopping and culture. DON'T JUST VISIT PARADISE - OWN IT. Schedule your private tour of this extraordinary waterfront estate today.

OSPREY

622 BAYSHORE DRIVE

6 Beds

5 Baths

6,627 Sq.Ft.

$5,700,000

MLS#: A4657777

#A4662210

OSPREY

614 BAYSHORE DRIVE

3 Beds

4 Baths

6,347 Sq.Ft.

$5,500,000

MLS#: A4662210

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.

OSPREY

1049 N CASEY KEY ROAD

3 Beds

3 Baths

3,373 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**

OSPREY

854 MACEWEN DRIVE

4 Beds

4 Baths

11,650 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.

OSPREY

1042 N CASEY KEY ROAD

4 Beds

4 Baths

6,556 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.

OSPREY

112 OSPREY POINT DRIVE

4 Beds

5 Baths

11,076 Sq.Ft.

$3,500,000

MLS#: O6305818

**FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situated on a SERENE, INTERIOR, CUL-DE-SAC lot with NO FLOOD concern (Zone “X”) behind the Secure Gates of the highly sought after Bayside neighborhood within The Oaks Country Club community, just steps from Little Sarasota Bay. An Expansive Floorplan entails 4-BEDs plus 4-FULL BATHS while a full list of EXCEPTIONAL FEATURES is available upon request and includes Soaring 16ft and Vaulted Ceilings, Impressive White Oak and Marble Floors, Custom Crown trim, Plantation Shutters, many Built-Ins…to name a few. The Gorgeous, Chef’s Kitchen showcases marble counters, custom hardwood cabinetry and Galley Workstation Sink while premium appliances include LA CORNUE Gas Range, SUBZERO, BOSCH, etc. Enjoy your tranquil and private outdoor sanctuary from an expansive screened lanai with Heated Pool & Spa, Outdoor Kitchen and multiple covered seating areas while enjoying the surrounding butterfly, bee and hummingbird gardens and lake scenery. MANY RECENT UPDATES include Hurricane IMPACT Windows (2022), GENERAC Generator w/ Buried Propane Tank (2020), 3-HVAC Systems (2021), ROOF (2015), POOL HEATER (2025) and Much MORE! 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 and AERIAL VIDEO**

OSPREY

662 FERNWALK LANE

4 Beds

4 Baths

6,300 Sq.Ft.

$2,995,000

MLS#: A4635707

Tucked away in a quiet cul-de-sac on a double lot beneath majestic oaks, this almost 5,000 sq ft, timeless 2-story home blends sophistication with modern comfort. Situated on the first hole of Heron Golf Course, the home features soaring 11-ft ceilings, marble floors, and crystal chandeliers. A Louis XVI fireplace anchors the sunken living room, while French doors and expansive windows invite sunlight into the sunroom with breathtaking golf course views leading to three patios perfect for entertaining or relaxation. A brick path winds through lush gardens to the adjacent guest house. This nearly 2,000 sq ft guest house features 2 bedrooms, 2 en-suite bathrooms, a spacious living room, dining room, an outdoor kitchen, and a private laundry room. Overlooking the pool and spa, this guest retreat offers privacy and convenience, ideal for extended stays, visiting family, or in-law suite. The Oaks club amenities include 2 18-hole championship courses, and world-class tennis and pickleball facility. Located near Casey Key and the powdery white sands of Siesta Key. Enjoy the arts in Downtown Sarasota and shopping at St. Armands Circle; approximately a 20 minute drive. Membership at The Oaks is required.

OSPREY

236 SAINT JAMES PARK

6 Beds

6 Baths

9,589 Sq.Ft.

$2,900,000

MLS#: A4644125

#A4642364

OSPREY

49 OSPREY POINT DRIVE

4 Beds

3 Baths

5,227 Sq.Ft.

$2,695,000

MLS#: A4642364

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