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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 3 of 3.

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!
#A4656147

OSPREY

280 HIDDEN BAY DRIVE 303

3 Beds

2 Baths

2,241 Sq.Ft.

$4,400

MLS#: A4656147

One or more photo(s) has been virtually staged. ANNUAL or Short Term (3 Months Minimum) CONDO/VILLA AVAILABLE FOR LEASE with Option to Purchase! Short Term Rent is $6000 /month. Annual Lease is $4000/Month. Villas at the Harbor Village boasts luxurious amenities and waterfront living on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf, just across from Casey Key. Enjoy waterfront views along with views of the marina. Updates include newer appliances and A/C. The home has extra storage, and designated parking for two(2) cars. Community amenities include a heated swimming pool, 2 jacuzzis, sauna, kayak launch area, sunset deck, newly renovated Club House and a gym, along with landscaped grounds. Osprey, FL is a hidden gem nestled between Sarasota and Venice. Beautiful beaches, great shopping and restaurants are within close proximity. Water, garbage, basic cable are included. Call now to schedule a private showing and seize this great opportunity. Furnitures and internet are available upon request.
#A4651660

OSPREY

14041 BELLAGIO WAY 214

3 Beds

2 Baths

2,089 Sq.Ft.

$4,000

MLS#: A4651660

Date Available 5/15//25 end of lease 10/30/25 Luxury turnkey furnished Georgian Style Villa in beautiful, secure, gated Oaks Preserve within The Oaks Club in Osprey FL. Nestled among the live oaks and palms and native vegetation with lovely flowering annuals and perennials, this villa is one of twelve townhome and villa condominium units of the Bishopscourt Townhomes. Both en-suite bedrooms are separated by the living/dining room with wet bar and wine/beverage cooler. Bishopscourt community pool & clubhouse is a few steps thru the woods across the street. Both buildings just painted and new roofs in place. This quiet and convenient community has 24 hour attended gate, secure walking and close proximity to the Legacy Trail for cycling to either Sarasota or Venice. Siesta Key and Casey Key/Nokomis Beaches are 15 min. drive. Publix, Target, Walmart, Lowes, Fitness Centers within 3 minutes. 1-75 is 12 minutes away.
#A4652918

OSPREY

76 BISHOPS COURT ROAD 116

2 Beds

2 Baths

1,780 Sq.Ft.

$3,995

MLS#: A4652918

Enjoy luxury waterfront living in this beautifully updated 6th-floor condo at Blackburn Harbor Residences, overlooking the Blackburn bay. This 2-bedroom, 2-bath unit includes a den/flex room and offers panoramic water views from the main rooms. The fully remodeled kitchen features quartz countertops, stainless steel appliances, and two refrigerators—perfect for entertaining. From the living room the glass sliders open to a private covered balcony that overlooks a gorgeous view of the Blackburn Bay. The Master Bedroom is spacious with private sliders that lead to the balcony and equipped with 2 walk-in closets. The Master Bathroom features dual vanity sinks, a private vanity, and a spacious walk-in shower. The Guest bedroom is nicely situated to the Guest Bathroom that features a tub and shower combination. The flex room is ideal as a home office or can easily accommodate guests with a comfortable sofa sleeper. The community offers an impressive array of amenities, including a heated pool, fitness center, clubhouse, tennis and pickleball courts, shuffleboard, scenic walking trails, a kayak launch, boat dock, fishing pier, and several outdoor grilling areas with a gazebo—perfect for embracing the Florida lifestyle. Ideally located just minutes from Nokomis Beach, Casey Key, Venice Beach, and the world-famous Siesta Key. Residents also enjoy convenient access to Oscar Scherer State Park, historic Downtown Venice, and lively Downtown Sarasota—offering premier shopping, dining, and entertainment options. ~Association: Application & Fee are Required. ~Utilites: None. ~Pets: No, sorry.
#N6139624

OSPREY

5100 JESSIE HARBOR DRIVE 602

2 Beds

2 Baths

2,304 Sq.Ft.

$3,950

MLS#: N6139624

New on site 2 days ago
Now Available – Lease Option or Lease Purchase Opportunity in Willowbend! Live large in this 3,183 sq ft Lee Wetherington-built pool home with preserve and pond views. Flexible lease terms now offered: Lease Option with option fee - OR - Lease Purchase with buyer commitment and possible rent credit Spacious layout with 4 true bedrooms on the main floor plus an upstairs bonus room—ideal for guests, home office, or gym. Oversized tip lot with full privacy and scenic views of Oscar Scherer Park. Ideal for luxury renters or relocation clients seeking a low-maintenance home in a quiet, established community. Features include a private pool, 3-car garage, newer AC and water heater, hurricane shutters, and builder-grade finishes—priced below market based on comparable sales. Located in a top-rated school district, just minutes from Casey Key Beach and the nationally ranked Pine View School. Willowbend offers resort-style amenities including a heated pool, fitness center, tennis/pickleball courts, and playground. Fee Includes: Cable TV, Community Pool, Internet, Maintenance Grounds, Recreational Facilities Seller is motivated and open to flexible short-term structures depending on the deal. Easy to show—schedule your private tour today!
#A4658924

OSPREY

650 CRANE PRAIRIE WAY

4 Beds

2 Baths

4,092 Sq.Ft.

$3,750

MLS#: A4658924

This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing charming architectural details and quality finishes, this traditional-style home offers an inviting floor plan with two bedrooms, each featuring its own en-suite bath. The gracious living and dining areas flow seamlessly into a spacious and private outdoor living space that overlooks a serene preserve, creating a perfect setting for relaxation. Set within a small, exclusive enclave of just 12 townhomes, residents also enjoy access to a quiet community pool ideal for social gatherings. Conveniently situated near shopping, dining, the white sands of Siesta Key Beach, and the vibrant cultural arts scene of downtown Sarasota, this home offers both comfort and an exceptional lifestyle.
#A4648193

OSPREY

60 BISHOPS COURT ROAD 114

2 Beds

3 Baths

2,154 Sq.Ft.

$3,695

MLS#: A4648193

***AVAILABLE NOVEMBER 2025 THRU JANUARY 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located in South Sarasota. Open plan, easy to show! Close to Siesta Key, Costco restaurants very convenient to all the amenities Sarasota has to offer.
#A4589608

OSPREY

51 MAC EWEN DRIVE 1

1 Beds

1 Baths

623 Sq.Ft.

$2,500

MLS#: A4589608

This lovely 3 bedroom, 2 ½ bath townhome. This unfurnished unit has (2) Separate Single car garages-Storage and Parking. Located Close to Beaches, Shopping and Dining. Like New, Freshly Painted, Built in 2016. The kitchen has granite, nice cabinets, and stainless appliances. Beautiful Water View w/ fountain! Large open kitchen, dining and living room. All bedrooms are upstairs and are great sized. The Master Bedroom includes walk in closet, dual sinks and walk in shower. 2nd floor laundry-washer and dryer. Bay Street has a resort like pool with a nice, covered area great for lounging and Exercise Room. Conveniently located to all the best of Sarasota and Venice. 15-minute drive to Siesta Key beach/village, 10-minute drive to Nokomis Beach. Close to great dining and entertainment in Venice or Gulf Gate-downtown Sarasota. Legacy Trail head is close by. The Unit is Vacant, Rented Unfurnished and available for Rent $2450. per month-12-month minimum. CC & BC required. No Smoking. Landlord will consider 1 small dog.
#N6138829

OSPREY

4209 EXPEDITION WAY 102

3 Beds

2 Baths

1,655 Sq.Ft.

$2,450

MLS#: N6138829

Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards your first full month's rent! Welcome home to this beautiful 3-bedroom, 2-bathroom condo in the sought after gated community of Bay Street Village! Neutral paint, ceiling fans throughout, tile flooring in the main living areas and carpet in the bedrooms make decorating a breeze! The open floor plan between the living and dining room provide plenty of central space to entertain all year round! The kitchen features stunning granite countertops, a breakfast bar, solid wood cabinets, a spacious pantry for all of your storage needs and stainless steel appliances, including a dishwasher, refrigerator, range, and microwave. Enjoy the spectacular lake views from the screened balcony, with access from the living room and primary bedroom! Best view in the complex! The primary bedroom features en suite bathroom with dual sinks and custom tile walk-in shower, complete with a large walk-in closet and linen closet. Turn your two roomy guest bedrooms into the perfect spaces for your friends and family, both featuring ample closet space and natural Florida sunshine coming through the large windows! One car garage directly below the unit. Make laundry days hassle free with a washer and dryer included in the unit! Trash, pest control, and grounds maintenance are all included in rent! Sorry, no pets. Ideally located near the top rated schools in Florida, Pine View, is just a short drive away. Enjoy all the benefits of maintenance free living in the new Bay Street Village community. The clubhouse features a sparkling swimming pool and well-equipped fitness center. Bay Street is perfectly situated halfway between quaint Venice and bustling Sarasota. Only a short drive from the highly rated sand beach of Siesta Key and countless options for restaurants, entertainment, and much more! Ryntal Property Management has partnered with Obligo to provide a security deposit alternative to qualified renters! Call today for more information. Submit all applications to Ryntal Property Management ONLY! Qualifications: We run a complete background check that includes credit, income verification, prior landlord and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550.
#A4654841

OSPREY

4248 EXPEDITION WAY 4248

3 Beds

2 Baths

1,510 Sq.Ft.

$2,400

MLS#: A4654841

Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards your first full month's rent! Welcome to this lovely, fully furnished, 2-bedroom, 2-bathroom condo in Osprey! This condo is ready to welcome your entire family, complete with bright and airy spaces, spacious bedrooms, and a coastal vibe perfect for the ideal Florida lifestyle! Not only will this home be everything you are looking for, but you will also have the luxury of a bonus room, perfect for turning into a home office or playroom! The kitchen features stunning, bright cabinets, a pantry, granite countertops, and a neutral subway tile backsplash. Appliances include a stainless-steel refrigerator, microwave, range, and dishwasher. The kitchen island doubles as a casual dining space, perfect for intimate meals with the family. Ceiling fans in every room, tile flooring in the main living areas, hardwood flooring in the bedrooms, and neutral paint throughout make decorating a breeze! *Updated flooring photos coming soon!* The open concept living, and kitchen area is full of life! Brightly illuminated by the large, surrounding windows, this lovely living room is the perfect space for entertaining your invited guests. Plus, you will also have access to your private, screened lanai, where you can continue the entertainment and enjoy all of Florida's wonderful weather from the comfort of your home. The primary bedroom has the perfect view of the community pond and is complete with a walk-in closet and an en suite bathroom with a dual sink vanity space and a walk-in shower. The second bedroom features a large closet for all your wardrobe needs and shares the guest bathroom down the hall that features a granite vanity space and a tub, perfect for decompressing after a long and busy work week! A laundry room with a full-size washer and dryer is located near the 2 car garage entrance to the unit and completes the remainder of this home. Trash, lawn care, and pest control included in rent. Pets are okay, no dangerous breeds, and 35 lbs. max. Enjoy all the benefits of maintenance-free living in the new Bay Street Village community. This gated community features a sparkling swimming pool and a well-equipped fitness center, perfect for enjoying with the entire family! Bay Street is perfectly situated halfway between quaint Venice and bustling Sarasota. Located in Sarasota's top-rated and nationally recognized Pine View School and only a short drive from the highly rated sand beach of Siesta Key! You'll be far enough away from tourists and traffic issues, but you still have countless options for restaurants, entertainment, and much more. Ryntal Property Management has partnered with Obligo to provide a security deposit alternative to qualified renters! Call today for more information. Submit all applications to Ryntal Property Management ONLY! Qualifications: We run a complete background check that includes credit, income verification, prior landlord and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550.
#A4651247

OSPREY

4214 FRONTIER LANE 102

2 Beds

2 Baths

2,034 Sq.Ft.

$2,400

MLS#: A4651247

Spacious 2nd-floor end-unit with one car garage (22x11) provides nearly 1,600 sq. ft. and stunning lake and courtyard views. This updated 2BR + den/office (can be 3rd BR) features the largest floor plan in the building, no carpet (tile & laminate throughout), an open-concept layout, and tons of natural light. Kitchen has granite counters, stainless appliances, and upgraded cabinets. Master suite includes two walk-in closets, lanai access, and a spa-like bath with split vanities and garden tub. Second en-suite bedroom has a large closet and private bath access. One-car garage included with open parking or 2nd vehicle. Lake Vista is a gated, resort-style community located directly on Sarasota Bay with a scenic boardwalk and trail access to the water. Amenities include a heated pool/spa, fitness room, clubhouse, tennis/pickleball, kayak launch, fishing pier & more. Minutes from Siesta Key, shopping, dining, golf, and more.
#R4909551

OSPREY

291 HIDDEN BAY DRIVE 201

2 Beds

2 Baths

1,960 Sq.Ft.

$2,300

MLS#: R4909551

The unit is available for rent from July 15 ,2025.The minimum rental period is 3 months. The monthly rent is $2250. The tenant is responsible for electricity and internet costs. NO PETS! INCLUDED IN THE LEASE : Water, sewer. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling two-bedroom, two-bath, impeccably maintained, property move-in ready. Located on the second floor with a one-car garage, this 2016 built condominium features a light and bright feel and has an open great room floor plan with screened lanai. Spacious “Heron” floor plan makes great use of space with two bedrooms, two baths, Attached one car garage. Kitchen features a large center island that any chef will love. Stylish design elements including 42” Scottsdale Cherry Spice, Beautiful Firenze Granite kitchen countertops, and GE stainless steel appliance package including a washer and dryer. Double slider opens to screened corner balcony. Master suite features large walk-in closet, tiled walk-in shower, and double vanity. Bay Street Village is a maintenance-free gated community that includes a resort-style heated pool, fitness room, and club room. Close to shopping, dining, beaches and Pine View school. Please schedule your private showing today. You will not be disappointed.
#A4648720

OSPREY

184 EXPLORER DRIVE

2 Beds

2 Baths

1,450 Sq.Ft.

$2,250

MLS#: A4648720

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