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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.
$946,246
Med. List Price

Browse Osprey Real Estate Listings

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Over $5M

42 Properties Found. Page 2 of 3.

This undeveloped parcel in the Arbors is next to the manufactured home at 320 Tropic Drive in Arbors Mobile Home Park Co-Op. It has a gazebo on it. The same person owns both the lot with the gazebo AND the home at 320 Tropic Drive. She would like to sell both of them as a package deal. The listing for the home at 320 Tropic is: A4648481. Feel free to call the listing agent (same agent for both parcels) at any time. The Arbors is one of the most sought-after Co-Op, Resident-Owned 55+ parks in Sarasota County. Thank you. I look forward to hearing from you.
#A4648600

OSPREY

320 TROPIC DRIVE 171

None Beds

None Baths

0.09 acres

$50,000

MLS#: A4648600

New on site 4 days ago
Dry Boat Slip for Sale – Osprey Harbor Village, Sarasota County Secure your spot in one of Sarasota County’s premier boating destinations with this hurricane-protected dry boat slip at Osprey Harbor Village. Designed to offer both protection and convenience, this indoor slip ensures your boat is shielded from Florida’s unpredictable weather — potentially reducing your insurance premiums by eliminating storm prep. Slip Size: Accommodates boats up to 30’-6” L x 10’ W x 7’-6” H (Actual slip size: 31' long x 11' wide x 9'-6" high) Prime Location: Located just before the swing bridge to Casey Key at ICW Marker 33, north of Blackburn Point Bridge, this slip offers quick access to Midnight Pass and the Venice Inlet, making every boating trip easy and enjoyable. Top-Tier Amenities: Osprey Harbor Village is known for its premium services and full-service marina, including: Valet boat service Full-time staff Fuel and pump-out stations Wash racks and maintenance racks Fish cleaning tables Bait and tackle shop Picnic tables and restrooms On-site restaurant, deli, and ship store Whether you're focused on safety, convenience, or luxury, this dry boat slip delivers it all. Protect your investment, skip the hassle of storm prep, and enjoy effortless boating with first-class service at Osprey Harbor Village.
#A4658717

OSPREY

570 BLACKBURN POINT ROAD 6

None Beds

None Baths

N/A

$44,000

MLS#: A4658717

New on site 3 days ago
Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! Keep your boat safe from Floridas unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to 33L x 10.5W x 6.5H. With valet boat service, full-time staff, wash, fuel, and pump-out stations, fish cleaning tables, a bait and tackle shop, maintenance racks, picnic tables, restrooms, an on-site restaurant, deli, and ship store, its a boaters dream. Call ahead for splash, fueling, and even have your deli order waiting when you arrive. Enjoy quick access to Midnight Pass and the Venice Inlet, along with the peace of mind that comes from hurricane-safe indoor storage that could even reduce your insurance costs. Skip the storm prep, protect your investment, and enjoy effortless boating with first-class service at Osprey Harbor Village.
#A4658755

OSPREY

570 BLACKBURN POINT ROAD 11

None Beds

None Baths

N/A

$42,500

MLS#: A4658755

**RENTAL OPPORTUNITY (unfurnished)** SPACIOUS, LUXURIOUS and BEAUTIFULLY RENOVATED, GOLF COURSE ESTATE situated behind the SECURE GATES of The Oaks Country Club Community, Boasting OVER 9,000sf and located 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 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. **MUST SEE**
#A4594864

OSPREY

854 MACEWEN DRIVE

4 Beds

4 Baths

11,650 Sq.Ft.

$21,000

MLS#: A4594864

Beautiful completely renovated home with all the upgrades you can want. Available for annual, and shorter term leases. Pricing is for annual rent.
#A4652833

OSPREY

600 EAGLE WATCH LANE

3 Beds

3 Baths

5,157 Sq.Ft.

$12,000

MLS#: A4652833

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.
#A4622973

OSPREY

14041 BELLAGIO WAY 316

3 Beds

2 Baths

2,386 Sq.Ft.

$7,900

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.
#A4651991

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
#A4644465

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!
#A4651384

OSPREY

5100 JESSIE HARBOR DRIVE 504

3 Beds

2 Baths

2,304 Sq.Ft.

$7,000

MLS#: A4651384

If you're looking for a place that offers a rent to own opportunity, now is your chance! Welcome to your coastal sanctuary in the gated community of Villas at Osprey Harbor Village. Located just minutes from the newly reopened Midnight Pass beach, 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.
#A4650993

OSPREY

14041 BELLAGIO WAY 218

3 Beds

2 Baths

2,374 Sq.Ft.

$6,000

MLS#: A4650993

**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.
#A4640065

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.
#A4594860

OSPREY

293 TURQUOISE LANE

3 Beds

2 Baths

2,998 Sq.Ft.

$5,750

MLS#: A4594860

AVAILABLE ANNUAL OR 2026 SEASON. 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.
#A4410764

OSPREY

293 HIDDEN BAY DRIVE 203

2 Beds

2 Baths

1,568 Sq.Ft.

$5,000

MLS#: A4410764

Custom, Lee Wetherington home with a private heated pool in the sought after, maintenance free community of Willow Bend. Located close to Pineview School, Legacy Trail, Oscar Scherer Park and our world-famous beaches. This home features volume tray ceilings with lots of natural light, natural gas cooking, crown molding, built in features and indoor laundry. The large master suite features double walk in closets and has a separate sitting area/nursery or office. Enjoy morning coffee or an evening cocktail on the screened lanai over looking the pool with gorgeous views of the lake. The home is fitted with hurricane shutters (stored in the garage) so no worries! The community center is just a short walk away which features a clubhouse, heated pool and spa, fitness area, pickleball and a playground. Included with the rent are High speed internet, cable, yard maintenance and irrigation.
#A4657618

OSPREY

510 LATITUDE LANE

3 Beds

2 Baths

2,994 Sq.Ft.

$4,550

MLS#: A4657618

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!
#A4517611

OSPREY

152 NAVIGATION CIRCLE 107

3 Beds

2 Baths

1,889 Sq.Ft.

$4,500

MLS#: A4517611

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