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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

144

# of Listings

3

Avg # of Bedrooms

$407

Avg. $ / Sq.Ft.

$971,873

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

144 Properties Found. Page 9 of 10.

**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. NEW HURRICANE IMPACT SLIDING DOORS and WINDOWS; ROOF (2015). THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World. 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. **ENJOY VIEWING THE 3D VIRTUAL TOUR**

OSPREY

852 MACEWEN DRIVE

3 Beds

3 Baths

6,019 Sq.Ft.

$8,000

MLS#: A4659277

NOW AVAILABLE FOR APRIL AND OFF-SEASON MONTHS 2025 AND JAN-APRIL 2026! Welcome to BELLAGIO at Osprey Harbor Village, offering luxurious waterfront living! This turnkey direct waterfront condo has 3 beds/2 baths plus a den is the perfect place for your next Florida vacation, located in a private gated community. As you step off the elevator, you are basically outside this 3rd floor end unit. Upon entering, you are met with a spacious foyer which leads to the nicely appointed rooms. The kitchen has wood cabinets and granite counters, stainless steel appliances and comes fully equipped. Off of the kitchen is the living/dining area with sliding glass doors opening onto the large, spacious balcony overlooking the bay/harbor. The master suite has a king-sized bed, large walk-in closet, en-suite bathroom with separate shower and soaking tub, and private water closet. Enjoy more water views from the master bedroom with sliders opening onto the balcony. The 2nd bedroom is nicely furnished with a queen-sized bed, bedroom 3 has 2 twin beds, and guest bathroom has a walk-in shower and single vanity. There is a large separate laundry room with washer, dryer, a sink and plenty of storage cupboards. Wake up to the amazing waterfront views and enjoy your morning coffee on the furnished balcony. Osprey Harbor Village has it all! The Community has a resort-style bay-front heated pool and spa, sauna room, state-of-the-art fitness facility and a clubhouse with flat-screen TV's, kitchen, BBQ grills, fishing pier, boat docks, kayak launch, boat storage, on-site full-service marina and waterfront restaurant. covered under building garage parking for two cars, with elevators leading to your condo. Only minutes to the incredible Nokomis Beach, Siesta Key, and Venice Beach, shopping, dining, including the renowned Casey Key Fish House and Deep Lagoon, and walking distance to Blackburn Point Park! Easy access to I75 to University Town Center and Mall where there is an abundance of shops and restaurants.

OSPREY

14041 BELLAGIO WAY 316

3 Beds

2 Baths

2,386 Sq.Ft.

$7,500

MLS#: A4622973

DO YOU WANT COMFORT AND LUXURY WHILE YOU LOOK AROUND WATERFRONT ? JUMP ON THIS LUXURY TURNKEY RENTAL. A ROOM FOR EVERY HUMAN OR FURRY FRIEND. HEATED POOL. PREMIUM CHEFS KITCHEN, PREMIUM FLOORPLAN, AND PREMIUM NEIGHBORHOOD. FLY THROUGH AVAILABLE. CALL FOR MORE INFO. MINIMUM 3 MONTH RENTAL MAY- OCT 2025 , ONLY.

OSPREY

1216 FLYING BRIDGE LANE

5 Beds

4 Baths

5,000 Sq.Ft.

$7,500

MLS#: A4651991

Now AVAILABLE FOR LEASE WINTER SEASON 2026 at PINE RUN Condominiums in Osprey, Florida! 3BR/2.5BA Location! Location! West of the Trail, Pine Run is a waterfront tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of light and color with vaulted ceiling in the main Great Room. Custom designed Kitchen is EAT-IN. Main Bedroom Suite is on the first floor and two second story bedrooms. Private screened patio lanai to relax in paradise with a nature view and birdsong. Carport parking. Pine Run is a friendly community. Amenities two heated pools, tennis courts, pickle ball courts, canopy tree lined walking trails, brick patio with fire pit and grill, kayak storage and Club House. Located less than a half mile from the Gulf of Mexico and the inland waterway. Pine Run sits halfway between Sarasota and Venice on Blackburn Point Road. Less than 15 minutes drive and you are on Nokomis Beach with plenty of parking available. Oscar Scherer State Park is less than a mile south and the Legacy Bike Trail from Venice to Sarasota runs just east of Pine Run. Great walking neighborhood; Publix, CVS, stores, services and restaurants conveniently located. AVAILABLE for one month or longer stay as of April 2025 through mid October 2025. Rates for December through April $7200 and May through November $3600 monthly + 13% tax. Additional charges Sales and Resort Taxes (13%) and Departure Clean. Rates include all utilities and WIFI. NO PETS / NO SMOKING

OSPREY

101 WOODLAND PLACE

3 Beds

2 Baths

2,039 Sq.Ft.

$7,200

MLS#: A4644465

This beautiful 5th Floor condo located in Blackburn Harbor Residences is now available for Season 2026! There are breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was converted from a den) and 2 bathrooms. As you step inside the foyer, you are met with a bright and open floor plan with a separate dining area, large living room leading onto the covered and furnished balcony with its magnificent water views! The spacious and beautifully updated kitchen has granite countertops and stainless-steel appliances and is fully equipped. The primary suite has a king-sized bed, en-suite bathroom with a large walk-in shower, a separate soaking tub, and dual sinks. There are two additional guest rooms, one with a queen-sized bed and the other has 2 twin beds, plus a separate guest bathroom with walk-in shower, large granite vanity area with a single sink, and a separate laundry room with full-size side-by-side washer and dryer. The condo has an assigned parking space in the underground garage. Blackburn Harbor is a gated community and offers many amenities, which include a heated pool, fitness center, clubhouse, pickleball and tennis courts, shuffleboard, kayak launch, boat dock and fishing pier. In addition, there is a gazebo, outdoor grills and walking trails. The waterway leads out to the Intracoastal Waterway, with access to the Gulf of Mexico. You are in walking distance to Oscar Scherer Park, a short drive to the beautiful gulf beaches of Nokomis Beach, Casey Key, South and North Jetty, Venice Beach, Caspersen Beach, and the famous Siesta Key Beach! Plus, there is an abundance of shopping and dining, from the beautiful Historic Venice to Downtown Sarasota which is full of entertainment of all kinds!

OSPREY

5100 JESSIE HARBOR DRIVE 504

3 Beds

2 Baths

2,304 Sq.Ft.

$7,000

MLS#: A4651384

Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 90 Day minimum stay in Peak Season at $10,500/mo plus fees; Minimum 60 Day stay in Off Season at $6,500/mo plus fees.

Your Gulf Coast getaway awaits at this beautifully furnished 3-bedroom, 3-bath pool home in the scenic Willowbend community of Osprey, FL. Ideal for mid-term stays, this spacious retreat features a private screened-in pool, open-concept living, and a dedicated office workspace—perfect for remote work and extended relaxation.

The fully equipped kitchen boasts granite countertops and stainless steel appliances, flowing into a bright living area and a covered lanai for outdoor dining and lounging. The master suite offers direct pool access and a spa-like bath for ultimate comfort.

Beach gear provided: chairs, umbrella, cooler, and towels
Dedicated home office setup with desk, chair, and fast Wi-Fi
Distance to beaches:
- Nokomis Beach – 10 minutes
- Casey Key – 12 minutes
- Siesta Key – 20 minutes

Guests enjoy full access to Willowbend’s resort-style amenities: a heated pool and spa, fitness center, pickleball and basketball courts, and peaceful walking trails.

Please Note: This home is part of an HOA that requires guest registration. After booking, we will request basic information to complete and submit the application. All HOA application fees are included in the rental cost—no surprises.

OSPREY

521 HABITAT BOULEVARD

3 Beds

3 Baths

2,284 Sq.Ft.

$6,500

MLS#: A4661768

**FURNISHED, 3-BED / 3-FULL BATH, Over 2500sf CONDO with FANTASTIC VIEW** features an Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Spacious interior which boasts beautiful Crown Moldings, Hardwood Floors, a well-equipped Kitchen with granite counter and Stainless-Steel appliances, etc. The Owner’s Bedroom Suite features a Walk-in Closet, Dual Vanities, Soaking Tub and Stunning, Custom Tiled Shower. The Spacious, Screened Balcony offers a PRIVATE and serene setting where you can view wonderful wildlife and Gorgeous Sunsets! This residence includes a single, covered parking space and climate-controlled storage unit. The adjacent Amenity Center offers exclusive access to Meridian Condo residents and features a Heated Pool & Spa, Fitness facility and Outdoor Grilling area. The Oaks-Preserve is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, Area Beaches including #1 Rated Siesta Key and all that Gulf Coast living has to offer.

OSPREY

3603 N POINT ROAD 602

3 Beds

3 Baths

2,904 Sq.Ft.

$5,900

MLS#: A4640065

**RARE RENTAL OPPORTUNITY (UNFURNISHED)** This 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 just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer.

OSPREY

293 TURQUOISE LANE

3 Beds

2 Baths

2,998 Sq.Ft.

$5,750

MLS#: A4594860

RENTED JANUARY TILL MARCH 2026. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second-floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer & dryer inside unit. Nicely renovated with closet barn doors. Stainless appliances. Detached one car garage immediately in front of condo and plenty of parking. PET OKAY with owner approval and nonrefundable pet fee. Resort style community pool, heated spa, fitness room, tennis courts, reading room, BBQ area with covered bar for guests, community clubhouse with kitchen. Short distance to shores of Little Sarasota Bay, Casey Key, Siesta Key. Fishing pier. Easy commute to shopping, restaurants and more. NO CATS. OWNER HAS ALLERGIES. CALL AGENT FOR MORE INFORMATION. Rentals under 6 months are subject to Sales and Tourist tax(13%). Note that rates are subject to change without notice and reservations are not guaranteed until initial reservation deposit is received.

OSPREY

293 HIDDEN BAY DRIVE 203

2 Beds

2 Baths

1,568 Sq.Ft.

$5,000

MLS#: A4410764

Welcome to your coastal sanctuary in the gated community of Villas at Osprey Harbor Village. Located just minutes from Midnight Pass beach, Snake Island and walking distance to Casey Key fish house. This impeccably remodeled 3 bedroom, 2 bathroom residence offers an elegant, light-filled living space with breath taking harbor and sunset views from every room. Designed with both comfort and style in mind, this open layout features elegant coastal finishes throughout, a dry bar, an additional flex space for an office, den, or gym, and a spacious laundry room with plenty of storage. The spectacular primary suite features a newly designed spa style experience with a shower, tub, and floor lighting to further elevate your relaxation. Start your mornings with a cup of coffee on your balcony as you take in the tranquil harbor views and watch dolphins and manatee play. 40' wet slip available to rent for $1000/month. Gated community with new metal roof and all new landscaping. Looking to purchase? This condo is also for sale. Call today for more info.

OSPREY

14041 BELLAGIO WAY 218

3 Beds

2 Baths

2,374 Sq.Ft.

$5,000

MLS#: A4650993

Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with solid wooden cabinetry, topped with slab granite counters and breakfast bar and complemented with stainless steel appliances. The master suite is spacious with a king bed, walk in closet and en suite bathroom with walk in shower and double vanity. There are two additional bedrooms-one with a queen size bed and one set up as a den with a pull out couch. The amenity package features a resort style heated pool, club room, fitness center and BBQ grills. Bay Street Park is right across the street and you'll find yourself close to the beach, downtown Sarasota or Venice, the Legacy Trail, shopping, dining and museums. Available July 1 thru Dec 31, 2025. This property has now been leased Jan thru April 4 2026. This community is governed by a homeowners association. Approval may include an application, background screening, fees, and an approval process. Contact the agent for details. Call now for your next vacation!

OSPREY

152 NAVIGATION CIRCLE 107

3 Beds

2 Baths

1,889 Sq.Ft.

$4,500

MLS#: A4517611

One or more photo(s) has been virtually staged. Annual Rental. This newly constructed 3rd floor condo is available for immediate occupancy at Hidden Bay in Osprey. This gorgeous 3 Bedroom PLUS a Home Office is light, bright and very spacious! Wood and tile floors throughout- NO CARPETING! The Primary suite features 2 walk-in closets, sliding glass doors leading to the lanai and an ensuite with a beautiful walk-in shower and 2 separate vanities. The two guest suites share a bathroom which has a nice shower/ tub combo. Across the hall you will find the home office which has a gorgeous built in desk and plenty of cabinetry to keep your work space neat. You’ll love the separate laundry room which has space for hanging clothes, folding and plenty of storage space. The large lanai is enclosed and the perfect place to enjoy the famous Gulf Sunsets. This particular unit is in close proximity to the elevator which makes bringing in groceries a breeze! Hidden Bay is a very amenity rich community including a large heated pool and spa, fitness center, clubhouse, tennis and pickleball courts, bayside boardwalk and tiki hut with grills. The location is amazing- conveniently located just a short drive to plenty of shopping and dining options including Max’s Table, Evie’s On The Bay, Mad Moe’s, Local Pizza, Walmart and a short drive to 681. This is your chance to live the waterfront lifestyle while having access to all of your creature comforts!

OSPREY

280 HIDDEN BAY DRIVE 303

3 Beds

2 Baths

2,241 Sq.Ft.

$4,250

MLS#: A4656147

#A4659999

OSPREY

280 HIDDEN BAY DRIVE E 201

3 Beds

2 Baths

2,434 Sq.Ft.

$4,200

MLS#: A4659999

#A4660000

OSPREY

280 HIDDEN BAY DRIVE 302

3 Beds

2 Baths

2,241 Sq.Ft.

$4,200

MLS#: A4660000

#A4658758

OSPREY

280 HIDDEN BAY DRIVE E 203

3 Beds

2 Baths

2,236 Sq.Ft.

$4,200

MLS#: A4658758

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