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Osprey

One of the most popular communities provided by Michael Graf

Osprey

About Osprey

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.

One of the most popular communities provided by Michael Graf

172

# of Listings

3

Avg # of Bedrooms

$462

Avg. $ / Sq.Ft.

$1,089,700

Med. List Price

Browse Osprey Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

55 Properties Found. Page 1 of 4.

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

1,404 Sq.Ft.

$550,000

MLS#: N6138441

Price reduced

#A4638035

OSPREY

393 N POINT ROAD 604

3 Beds

3 Baths

2,778 Sq.Ft.

$1,000,000

MLS#: A4638035

Welcome to your Boater's Paradise! This well-maintained South Bay home is your key to enjoy one of the best neighborhoods in the area. This three-bedroom pool home has the perfect layout with the primary bedroom and en suite on one side of the home and the two additional bedrooms on the other. A major renovation in 2017 included new flooring thought the entire home, totally gutted and installed new bathrooms with custom vanities and all new interior shaker doors throughout the house. This home was re-piped for both water and sewer. Every ceiling was updated with a new surface and new recessed lighting. The shiplap living room is bright and airy and flows onto the lanai where you will find the resurfaced pool, a new cage and new marble pavers. The lanai has plenty of covered space for a sitting area , TV and a dining area. There are 3 rooms with slider access to the lanai, master, living, and family room. All the closets have built-in shelfing and are well designed. The garage has new built-in storage with doors and epoxy floors. The landscaping creates a very private back yard with fence like privacy using 6-foot-high pitch apple plants. The magnificent big palm tree in the front yard along with 8 others palms on the property really makes you feel the Florida vibe. Southbay's active community has a newly renovated waterfront clubhouse featuring a grand ballroom, catering kitchen, and state-of-the-art fitness center overlooking the marina. Enjoy the heated pool, youth pool, tennis courts, pickleball courts, shuffleboard, bocce, playground, basketball, walking trails and an intercoastal waterfront park. Boating enthusiasts will appreciate the community-owned deep-water marina with direct access to the Intercoastal Waterway with no fixed bridges to the Gulf. The marina’s low-fee boat slips are exclusive to Southbay owners and can accommodate anything from personal watercraft to 55’ yachts. Southbay has a calendar full of social events, there's always something to connect over. The community is golf cart-friendly--just hop in your cart to go to one of the events or head out to local shopping, tiki bars, or the beach. Families will love the proximity to Pine View School, renowned as Florida's #1 charter school and one of the nation's few standalone gifted programs. Don't miss your chance to own in Southbay!

OSPREY

1486 LANDVIEW LANE

3 Beds

2 Baths

1,869 Sq.Ft.

$995,000

MLS#: D6144630

#A4665288

OSPREY

1602 SOUTHBAY DRIVE

4 Beds

3 Baths

2,980 Sq.Ft.

$995,000

MLS#: A4665288

**EXQUISITELY UPDATED, TURNKEY FURNISHED, POOL HOME** in Popular BAY OAKS ESTATES. This Stunning Residence is MOVE-IN READY (just Bring Your Suitcase!) and features a LIGHT and BRIGHT, OPEN FLOORPLAN including 3 BEDS plus STUDY/DEN and 2 FULL BATHS. The Gourmet Kitchen boasts a modern, European design with premium appliance package and counter sitting area while the primary bedroom suite offers an expansive, private retreat complete with walk-in closets, dual vanities, Jacuzzi tub, custom-tiled shower, Italian smart toilet-bidet, etc. A complete List of Recent Upgrades is attached and available upon request and includes but is not limited to NEW Kitchen & Baths, Interior and Exterior Paint, whole home LED lighting and smart fans, built-in Sound System, Flooring (tile, luxury vinyl, carpet), Washer & Dryer, water filtration, exterior LED lighting, pavered driveway, Irrigation system, privacy fence, storage shed and So Much MORE! Relish in the utmost Florida lifestyle with a Saltwater Pool in a large, screened lanai with covered seating area while overlooking the serene and private landscape. Enjoy peace of mind with NEW HURRICANE IMPACT WINDOWS and DOORS, MASONRY Wall Construction, and a structure situated in Flood Zone “X”. LOW HOA. Ideally Located close to Area Beaches including #1-Rated SIESTA BEACH, the Popular LEGACY BIKE TRAIL, #1-Rated PINE VIEW SCHOOL, Shopping, Downtown Sarasota and Venice cultural venues, and all that Florida’s Gulf Coast Living has to offer. **PLEASE ENJOY VIEWING THE 3D VIRTUAL TOUR**

OSPREY

599 PINE RANCH EAST ROAD

3 Beds

2 Baths

2,188 Sq.Ft.

$995,000

MLS#: A4660895

**TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the Single Largest 0.32 Acre Cul De Sac Lot in the Popular SAINT JAMES PARK neighborhood in The Oaks Country Club. NEW ROOF (2024), HURRICANE IMPACT WINDOWS and SLIDING DOORS, FLOOD ZONE “X500”. Overlooking the Eagle Golf Course and Ideally Located near the Clubhouse and Campus of World Class Amenities, this Distinctive LIGHT AND BRIGHT floorplan offers 2-BEDS, 2 FULL BATHS, 2-Car Oversized Garage with EV Charging and features unique architectural details throughout including beautiful crown moldings, wainscoting, cozy fireplace, engineered hardwood and tile floors, built-in sound system, and More! A nicely equipped kitchen features hardwood cabinets and stainless steel appliances while the Spacious bedrooms include a primary bedroom suite with walk-in closet, dual vanities, soaking tub and custom-tiled shower. In addition to its wonderful curb appeal and beautifully manicured landscape, a Spacious and screened lanai offers Gorgeous Sunset Views with its ideal Western Exposure. 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.

OSPREY

227 SAINT JAMES PARK

2 Beds

2 Baths

2,071 Sq.Ft.

$995,000

MLS#: A4635743

Welcome to Emerald Woods, a desired cul-de-sac within The Oaks Preserve, and this private Lee
Wetherington custom home that will check all the boxes, and more. Situated on one of the
largest lots and surrounded by preserve for privacy, you’ll find essence and elegance as the
color palette interplays with natural light, and the southern facing lanai and pool will be where
you can enjoy the maintenance free lifestyle, and the quality of life second to none. Enter the
foyer through 8’ insulated front doors with impact glass, and 12’ high ceilings with wide
decorative crown molding. Designer exceptional interior and exterior details and finishes are
completed and tastefully appointed. The kitchen offers custom 42” wood upper cabinetry with
over and under cabinet lighting, granite countertops, a decorative tile backsplash, center island
with base cabinetry, a pantry with rollout shelving, stainless appliances (2023), and a seamless
glass aquarium window in the breakfast nook. The great room has 17” stone tile flooring,
custom built-in cabinetry and a custom designed stone fireplace with electric logs. The open
floor plan dining room has a hand painted tray ceiling, and a built in buffet with a granite top
and 42” upper cabinets with glass inserts. A fantastic escape awaits when you walk out your
sliding glass doors to the outdoor oasis that includes a newly resurfaced custom designed pool and spa
with a waterfall feature and a new pool screen and cage with a panoramic view maximizing the
enjoyment of the outdoor space. A dry bar/buffet makes entertaining outdoors so easy. The
primary suite offers an extended office/owner’s retreat with a custom designed built in desk and
cabinetry, handsome bamboo wood floors, two large walk-in closets with built-ins, a primary bath with
new vanities, undermount sinks, and designer brass and chrome fixtures. The second light and
bright guest suite has wood floors, a bay window with plantation shutters and an ensuite
custom designed bath. Additional special features include a new roof (2023) new landscaping
and sod, a paver brick driveway, and an oversized 2 car garage with tandem parking for a 3rd car
and tons of storage and cabinetry. Experience the best in this move in ready home, and begin
your lifestyle at The Oaks Country Club, with the best location in Sarasota County. Centrally
located to all the beautiful beaches and offering two 18 hole championship golf courses, tennis,
pickleball, croquet, fitness center, dining, and a wide variety of social options. The Oaks is a
Platinum Club of America, an Elite Distinguished Club of The World, and best of all there is no
waitlist for a golf or social membership! Don't wait to begin your terrific and exceptional lifestyle!

OSPREY

105 TURQUOISE LANE

3 Beds

2 Baths

2,606 Sq.Ft.

$995,000

MLS#: A4662015

Private Key West–style retreat on 2.53 wooded acres in Osprey. Rarely does a property of this size become available in such a convenient location—just minutes from Pine View School, shopping, restaurants, and the Intracoastal Waterway—yet offering the privacy and space of a true country setting. This combination of acreage and accessibility makes the home exceptionally unique for the area. A generous 37x60 paver-brick patio surrounds the screened lap-style pool, now protected by a freshly updated pool cage. Multiple French doors open to wide second-floor decks overlooking the peaceful wooded backdrop. A recently added metal roof enhances durability, longevity, and value. Inside, the home features oak hardwood floors, vaulted tongue-and-groove cypress ceilings, and a striking wood-burning fireplace that add warmth and character throughout. The kitchen and baths retain their classic charm and present an excellent opportunity for updating to suit modern preferences. The flexible layout includes two potential primary suites and a first-floor bonus room with full bath that works well for guests or creative uses. The lower level remains plumbed for a second kitchen and laundry, offering an easy path for future installation or multigenerational living. With no deed restrictions and an expansive amount of usable land, this country estate in town offers endless potential—whether for hobbies, animals, enhancements, or simply enjoying the quiet beauty of its natural surroundings.

OSPREY

678 FAITH AVENUE

3 Beds

3 Baths

2,583 Sq.Ft.

$990,000

MLS#: A4674865

One or more photo(s) has been virtually staged. Waterfront Elegance at Blackburn Harbor! Experience the comfort of a home with the convenience of condo living in this spacious 3-bedroom, 3.5-bath plus den residence offering 3,771 sq. ft. of beautifully designed space and 10-foot tray ceilings throughout and a new roof. Enjoy panoramic water views from the gourmet kitchen, featuring wood cabinetry, granite countertops, stainless steel appliances, a cook’s island, and a cozy dinette — perfect for morning coffee with a view. All bedrooms are large with ensuite baths and walk in closets.
Set within Blackburn Harbor, a gated and pet-friendly waterfront community on 11 scenic acres, across the street has walking and bike trails including the Legacy Trail that runs from Sarasota to Venice. Residents can enjoy a lifestyle surrounded by nature and resort-style amenities with social gathering in the club house. It’s a boater’s paradise with protected deep-water dockage (up to 44 feet) complete with power, water, and no bridges to the Intracoastal Waterway.
Community highlights include kayak storage and launch, tennis and pickleball courts, a heated pool, fitness center, clubhouse, and a gazebo with grills. Outdoor enthusiasts will love the nature trails across the street at Oscar Scherer State Park, abundant birdlife, dolphins, manatees, and kayaking adventures to Casey Key Tiki Bar & Restaurant.
Perfectly located between Sarasota and Venice, Blackburn Harbor offers the best of both worlds — just minutes from beaches, cultural attractions, parks, shopping, and dining.

OSPREY

6100 JESSIE HARBOR DRIVE 202

3 Beds

3 Baths

3,771 Sq.Ft.

$970,000

MLS#: A4670353

At last- the home you've been looking for! This updated 3-bedroom 3 bath retreat is tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout, saltwater pool, den, in home gym, new tile roof, new AC, hurricane impact windows and doors as well as an easy low maintenance open floorplan. Enjoy boating, fishing, biking, pickleball and evenings by the community pool looking out over the marina watching amazing sunsets. Walk, bike our take a golf cart to nearby shopping, restaurants and tiki bars. A definite value in an amazing community!

OSPREY

172 SEA ANCHOR DRIVE

3 Beds

3 Baths

2,283 Sq.Ft.

$936,000

MLS#: A4671745

**STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s Bedroom Suite with Multiple walk-in closets and sitting area and much more! Enjoy the expansive and private outdoor living area in a screened lanai with wet bar and southern exposure overlooking a Garden and Tranquil Preserve. Mostly NEW Hurricane Impact Windows/Door. 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.

OSPREY

293 TURQUOISE LANE

3 Beds

2 Baths

2,271 Sq.Ft.

$910,000

MLS#: A4633961

Give yourself the gift of refined living in this expansive 2,778 square foot residence—the largest non-penthouse floor plan available in Meridian at The Oaks Preserve. Every detail in this meticulously maintained, and beautifully updated condominium has been thoughtfully designed to offer comfort, sophistication, and versatility, making it the perfect sanctuary for luxury living every day! Step inside and discover a home where space abounds and possibilities flourish. With three generously sized bedrooms, plus a dedicated dining room (currently being used as a den) and a versatile office/den or 4th bedroom, this home provides all the room you need to work, relax, and entertain, with the flexibility to use the rooms as you see fit. The great room is bathed in natural light, its gleaming wood floors enhancing the clean, contemporary lines of the interior. The updated kitchen will delight any home chef, offering optimal space for cooking and storage, whether you are preparing a casual breakfast or hosting a formal dinner. Enjoy your meals in the dining room, at the breakfast bar, in the cozy nook, or take them outside to the large, screened balcony, where a ceiling fan and the serene backdrop of a lush tropical preserve provide the ideal setting for alfresco dining. The small dry bar with wine cooler and cabinets to store your drink supplies and display your glassware is the perfect addition for when you are entertaining guests. Retreat to a sumptuous master suite. The large, carpeted bedroom is filled with natural light, and outfitted with a ceiling fan, plantation shutters, and custom closets. The master bathroom has been beautifully redone. With a soaking tub, separate shower and water closet, this space is absolutely gorgeous. Every inch of this unit has been curated to deliver both style and functionality, ensuring you feel pampered at every turn. Additional features include a large laundry room, Kevlar roll down hurricane shutters, two premium parking spaces and high-quality upgrades throughout. Club membership is required with homeownership. Residents of Meridian enjoy exclusive access to a private pool, relaxing spa, and a fully equipped workout room. Beyond these, The Oaks offers an impressive array of amenities including 36 holes of championship golf across two courses, twelve HAR-TRU tennis courts (four lighted), a state-of-the-art Wellfit Center, three on-site restaurants with year-round dining, croquet, bocce and pickleball courts and an active social calendar.

OSPREY

401 N POINT ROAD 304

3 Beds

3 Baths

2,778 Sq.Ft.

$900,000

MLS#: A4659785

Price reduced

Looking for a home you can fall in love with? The search is over! Once you see this thoughtfully updated, impeccably maintained 3 bedroom, 2 bath home in The Oaks Preserve you will know you have found your home-sweet-home. From the moment you pull up to the pavered driveway, the care taken to maintain this property is evident. Walk past the two-car garage to the pretty, double front doors with leaded glass and step into the light-filled interior. Here you will find everything you need for comfortable Florida living. There is a dedicated home office off the entryway, with plantation shutters and a ceiling fan. The formal dining area features a lovely decorative ceiling, and a beautiful built-in buffet with glass-fronted cabinetry. The great room features another gorgeous piece of built-in furniture; floor to ceiling sliding glass doors connect the screened lanai and this room, making it bright and airy. The open kitchen, with breakfast bar, features beautiful new granite counters, stainless appliances, a chef’s desk, built-in wine and beverage cooler. The adjoining breakfast nook is flooded with natural light that streams through the aquarium window and offers an amazing view over the pool and spa. The master suit is huge and has a sitting area with a built-in window seat and large walk-in closets with glass front storage. The spacious master bedroom has been updated with granite countertops, and features dual sinks, a tub and separate shower and has marble wall accents. The two guest bedrooms are good sized and offer ample closet space. The second bathroom has been tastefully updated with granite counter and marble accents. The 2 car garage, with epoxy floor, is air conditioned with plentiful storage. Situated in the Bishopscourt neighborhood, behind the secure gates of The Oaks Preserve, this beautiful home backs a lush, tropical preserve providing privacy for the sparkling pool and spa. The lanai has two separate areas surrounding the pool. A large, covered area with an outdoor kitchen and ceiling fan, the perfect place for al fresco dining in the shade, and pool and spa area, covered by a cage, allowing for frolicking in the sunshine. Or meet your neighbors for a dip in the Bishopscourt community pool. The Oaks Club amenities include two championship golf courses, an award-winning tennis program, pickle ball and croquet courts, and a state-of-the-art fitness center. With three outstanding restaurants, and a wide variety of social and recreational options, there is no need to look any further than here for the perfect place to enjoy the best of Florida country club living. Club membership is required with homeownership.

OSPREY

21 BAYHEAD LANE

3 Beds

2 Baths

2,216 Sq.Ft.

$900,000

MLS#: A4664085

Price reduced

Live like you’re on vacation in this updated Key West–style home West of the Trail. Upgrades include a new standing seam metal roof, hurricane impact windows, electric tankless water heater, wraparound "Lifeproof" composite decking, and a custom heated pool. Interior features vaulted ceilings with a mix of travertine, LVP, and tile flooring, plus a kitchen with solid wood cabinets, stainless steel appliances, beadboard ceiling, and custom backsplash. The screened second-story porch has an electronic roll-up system for open-air or enclosed comfort. A unique “hidden” door design allows the home to function as one residence or two separate units, with the lower level offering its own entrance, bedroom, bath, family room, and laundry—perfect for in-laws, guests, or rental income. Outdoors, enjoy lush landscaping, a tropical pool setting, and unbeatable location just a block from the public dock and kayak launch. Minutes to Sarasota, Venice Island, beaches, Legacy Trail, and Spanish Pointe.

OSPREY

38 W BAY STREET

3 Beds

2 Baths

2,124 Sq.Ft.

$899,000

MLS#: A4667010

This is an outstanding Southbay residence and a fantastic opportunity to live in one of the best boating communities on the Southwest coast of Florida. This home has been updated with a gourmet custom kitchen, perfect for entertaining guests and hosting company. From the granite countertops to the gas cooktop, and custom cabinetry, it is a pleasure to cook in here! The dining room is spacious with plenty of room plus a built-in custom buffet, overlooking the expansive living room. The media/family room featuring a wood-burning fireplace, is set up for a large screen TV and sound wired throughout to achieve maximum viewing and listening pleasure. The primary bedroom is huge with 2 large walk-in closets, and the en suite bathroom is well suited for comfort and convenience. The other two bedrooms are well-sized and the guest bathroom and half-bath have been tastefully updated. Outside, the oversized lanai provides plenty of room for entertaining or just relaxing, and enjoying the landscaped view.. Southbay Yacht & Racquet Club is a premier marina community with a newly renovated clubhouse offering numerous amenities, including a fitness room, card room, and two kitchens for preparing for events. The community has a geo-thermal pool overlooking the marina, a shuffleboard court, three tennis courts, four pickleball courts, a bocce ball court, and a basketball court. Plus, there is kayak storage, a waterfront park, and nearly 20 acres of common grounds with miles of walking trails and paths. This house is a unique treasure, perfect for someone wanting to live in an exceptional home within an exceptional community! Call for your showing today!

OSPREY

238 LOOKOUT POINT DRIVE

3 Beds

2 Baths

2,676 Sq.Ft.

$895,000

MLS#: A4671468

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