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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

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

49 Properties Found. Page 3 of 4.

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.
#A4410764

OSPREY

293 HIDDEN BAY DRIVE 203

2 Beds

2 Baths

1,568 Sq.Ft.

$5,000

MLS#: A4410764

BACIK ON THE MARKET HIGH SEASON NOW AVAILABLE!! 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 NOW AND DURING HIGH SEASON (DECEMBER THRU APRIL). 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 in the Florida sunshine!
#A4517611

OSPREY

152 NAVIGATION CIRCLE 107

3 Beds

2 Baths

1,528 Sq.Ft.

$4,500

MLS#: A4517611

Welcome home to Willow Bend, a tropical maintenance-free community located in middle of everything southwest Florida has to offer! Gorgeous turnkey 3 bedroom& 2 Bath Furnished annual rental near Nokomis Beach. Peaceful Lake views on an oversized lot. The pretty lanai features travertine marble tile and a HEATED POOL. Many upgrades include quartz kitchen counters, wood plank oak flooring, and custom closets. Master Bathroom has two walk in closets with ensuite bath and spa tower. Dedicated Office space comes equipped with built in cabinetry and plantation shutters. Laundry room with storage closet with an oversized sink and custom shelving, plus a 2-car garage with air-conditioning capabilities .Dynamite location in Osprey, near the Intracoastal Waterway, beaches, Legacy Trail, shopping, dining, grocery, coffee shop and tiki bars are minutes away. Top-rated Pine View School is within a short distance. Maintenance free has heated community pool, high speed internet, fitness center, pickleball court and playground. Move in Ready* Furnished*Annual Rental*Or Seasonal rental available 6-8 months 1st*last*and security* Dogs Allowed*Tenant Pays Electric ,Cable, Internet & Water* Application fee $30. AVAILABLE Second Week of December. Schedule a private showing today.
#A4671839

OSPREY

1308 THORNAPPLE DRIVE

3 Beds

2 Baths

2,188 Sq.Ft.

$4,500

MLS#: A4671839

AVAILABLE THIS SEASON JANURY AND FEBRUARY 2026.***No smoking,no pets permitted. Due at signing - total rent,security deposit,cleaning fee of $250,HOA fee of $150 and sales tax applicable. Heated swimming pool,small club house,gym and cabana across the street from this condo. Positioned perfectly in the highly coveted community of Bay Street Village,this second-story turnkey condo has two bedrooms (king size bed in the master and full size trundle with a twin pullout),two bathrooms and is a quick walk to the beautiful heated resort style pool. After walking through the front door and up the stairs,an open floor plan awaits,leading to a beautifully furnished living area,and a modern kitchen with a sliding-glass door to the screened balcony. The kitchen provides generous storage,granite counters,and stainless steel appliances. In addition,the condo comes with in-unit laundry. Single (attached) garage on first floor where you will find beach chairs,and items you might need to enjoy a day at the beach. Located perfectly between world famous Siesta Key and Nokomis Beach,you will have your feet in the beautiful powder sand of the gulf in under 15 minutes no matter the direction you go! Community amenities include gated entry,luxurious outdoor HEATED POOL,and gym. Utilities are included in the rent. This condo is less than 6 miles to Nokomis Beach,8 miles to Siesta Key Beach,8.5 miles from Venice Beach,and 2.5 miles from Oscar Scherer State Park,1 mile to Legacy Bike trail.
#N6141845

OSPREY

4243 EXPEDITION WAY 4243

2 Beds

2 Baths

1,335 Sq.Ft.

$4,500

MLS#: N6141845

READY FOR IMMEDIATE OCCUPANCY! Modern Elegance at Edgewater: A Luxurious Haven Overlooking Little Sarasota Bay Step into a world of contemporary sophistication with this new construction condominium nestled in the eminent enclave of Edgewater at Hidden Bay. Boasting 1937 square feet, this meticulously crafted residence offers three bedrooms, two bathrooms, and an inviting office space for your creative pursuits. The allure begins in the heart of the home – a sleek kitchen adorned with top-of-the-line LG appliances, complemented by solid wood cabinetry and exquisite quartz countertops that beckon culinary adventures. As natural light dances through expansive windows, partial views of tranquil Little Sarasota Bay create a serene backdrop to everyday living. Indulge in comfort and style as you unwind in the spacious bedrooms or revel in the luxurious ambiance of beautifully appointed bathrooms. Every detail has been thoughtfully considered to elevate your lifestyle, from high-quality finishes to seamless design elements that exude modern charm. Edgewater's coveted location offers more than just a place to call home; it provides a gateway to upscale living near waterways and green spaces. Embrace a life where convenience meets luxury – where every day is an opportunity for relaxation and rejuvenation amidst breathtaking surroundings. Discover unparalleled tranquility and refinement at Edgewater
#A4664183

OSPREY

280 HIDDEN BAY DRIVE 202

3 Beds

2 Baths

1,937 Sq.Ft.

$4,200

MLS#: A4664183

*AVAILABLE NOVEMBER 15, 2025 — PREVIEW BY APPOINTMENT ONLY* Currently occupied — showings available by appointment only. This beautifully updated 3-bedroom, 2-bathroom home, features a desirable split floor plan and a spacious 2-car garage. Offered unfurnished, with pool and yard maintenance included in the rent. HIGHLIGHTS: Open-concept layout designed for comfort, entertaining, and everyday functionality Generous screened lanai with private pool overlooking a serene natural preserve Located in a quiet, sought-after neighborhood perfect for families or professionals Zoned for top-rated schools, including Pine View School just 5 minutes away Easy access to Legacy Trail, parks, award-winning Gulf Coast beaches, shopping, dining, and more Conveniently located between Sarasota and Venice Enjoy peaceful Florida living in a home that balances privacy, location, and lifestyle. Don't miss your chance to make this your next home — schedule a private showing today!
#A4667570

OSPREY

603 PINE RANCH EAST ROAD

3 Beds

2 Baths

2,225 Sq.Ft.

$3,550

MLS#: A4667570

Welcome home to this charming and beautifully maintained 3-bedroom, 2-bath residence located on a great community. Step inside to a spacious open floor plan featuring a generous great room, a dedicated dining area, and a large primary suite. Cathedral ceilings, pocket sliding doors, and fluid room transitions create an airy atmosphere perfect for easy living and entertaining. The bright, eat-in kitchen offers abundant cabinetry and counter space, along with a new stainless-steel refrigerator (2024). The oversized primary bedroom features warm wood laminate flooring, a walk-in closet, a makeup vanity, and a lovely ensuite bathroom with a tiled walk-in shower. The split floor plan ensures privacy for guests, with a separate bedroom and full bath. The third bedroom, with double doors, is ideal as a guest room, office, or den. Outdoor living is a delight with a charming covered porch featuring a wood-slat ceiling overlooking a beautifully designed paver patio—perfect for relaxing or hosting friends and family. Located just minutes from downtown Venice and Sarasota, you’ll enjoy world-class dining, beautiful beaches, and exceptional shopping. Come see this wonderful home and make it yours—you will love living here!
#A4673066

OSPREY

2068 PREYMORE STREET

3 Beds

2 Baths

1,648 Sq.Ft.

$3,500

MLS#: A4673066

Annual unfurnished condominium available in Hidden Bay! Discover luxurious waterfront living in this stunning 2,000-square-foot, three-bedroom, three-bath condominium with breathtaking views of the Intracoastal Waterway. Enjoy spectacular sunsets from the expansive screened balcony, ideal for dining and relaxation. The home also comes with a private two-car garage. At the beautiful, gated community of Hidden Bay, residents enjoy resort-style amenities including a heated pool and spa, a tropical tiki hut with barbecue grills, lighted tennis and pickleball courts, a 500-yard elevated boardwalk through pristine mangroves, and a private kayak launch right on the Intracoastal. The newly renovated clubhouse features a gourmet catering kitchen with bar seating, a well-stocked library and a modern fitness center. Ideally situated for tranquility and convenience, you’re just minutes from shopping, dining, parks, the Legacy Trail, and only eight miles from world-famous Siesta Key, consistently ranked among America’s top beaches.
#A4673960

OSPREY

232 HIDDEN BAY DRIVE 504

3 Beds

3 Baths

2,000 Sq.Ft.

$3,500

MLS#: A4673960

Price reduced
Enjoy luxury waterfront living in this beautifully updated 6th-floor condo at Blackburn Harbor Residences on the West side of Tamiami Trail, 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. Assigned Parking located in the Parking Garage. 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. Close to Sarasota Memorial Hospital and the new Sarasota Memorial Hospital in Nokomis! ~Association: Application & Fee are Required. ~Utilities: Water/Sewer/Trash ~Pets: No, sorry. ~Available as a Seasonal: $ 4900 (Dec-Apr)
#N6139624

OSPREY

5100 JESSIE HARBOR DRIVE 602

2 Beds

2 Baths

2,143 Sq.Ft.

$3,500

MLS#: N6139624

Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodlands. It has TWO Bedrooms + a DEN, Great Room, double tray ceilings w/ crown molding. The den has double pocket doors! The kitchen is central in the house for entertaining, with plenty of storage, pull-out shelves, and 2 pantries! The Lanai has glimmering water views! Some nice features of the home: New Interior Paint! New Carpet! New Microwave! Irrigation System! Don't worry about maintaining the lawn/landscaping, that is included! Enjoy everything that surrounds you outside as well, such as the Legacy Trail just east of this home for walking, jogging, biking, rollerblading, strolling with your pets or whatever your outdoor activity of choice is. Just south of you is Oscar Scherer State Park for even more outdoor adventures. Just west of you is the beautiful Intracoastal Waterway & Gulf of Mexico with super soft white sandy beaches! You’re also in the company of the best schools around such as Pineview, next door to this neighborhood. Rivendell, a picturesque community known for its extensive green spaces, parks and 24 serene lakes!
#A4663790

OSPREY

1363 NEW FOREST LANE

2 Beds

2 Baths

1,738 Sq.Ft.

$3,000

MLS#: A4663790

Price reduced
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

1,890 Sq.Ft.

$2,995

MLS#: A4648193

Price reduced
ANNUAL/ GENTLY FURNISHED 4 BED/2.5 BATH. The home is gently furnished which will work perfectly for the family who has some furniture already. Available November1st - 9 month minimum - come stay here while your build your home. Master has a king bed with ensuite bathroom.- walk in shower, garden tub. Guest room has twin beds, 2nd guest room has a built in office and a Murphy bed. 4th bedroom is empty and could be an office or a bedroom w/ closet. There is a half bath near this room. The lanai is HUGE and has a nice tropical woods view. Centrally located - 14 minutes to the beach, 26 minutes to downtown Sarasota with all her cultural activities, 20 minutes to Venice, FL. Lawn care and pest control included. This is a non smoking house. A dog may be accepted with a pet fee. 1st month's rent, last month's rent and security needed at move in.
#A4668291

OSPREY

554 PINE RANCH EAST ROAD

4 Beds

2 Baths

2,064 Sq.Ft.

$2,600

MLS#: A4668291

Welcome to this stunning two-bedroom, two-bathroom retreat, perfectly designed for relaxation and entertainment! As you step inside, you'll notice the bright and airy open-plan living area, flooded with natural light pouring in through the large windows. But the true showstopper is the incredible backyard oasis! The expansive fenced yard beckons you to unwind and enjoy the fresh air, perfect for alfresco dining, outdoor games, or simply soaking up the sun. The screened porch provides a cozy haven for warm evenings or lazy mornings. Additional highlights include: Double garage for ample storage and parking Private and secure fenced yard Screened porch for bug-free relaxation Convenient laundry room Ample natural light throughout Don't miss this incredible opportunity to make this house your home!
#A4665305

OSPREY

305 BAY VISTA AVENUE

2 Beds

2 Baths

1,069 Sq.Ft.

$2,500

MLS#: A4665305

***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

Price reduced
Welcome to 163 Pennsylvania Avenue, nestled in the quaint community of Osprey, FL. This charming 3-bedroom, 2-bathroom home, built in 2018, offers a smart blend of style and energy efficiency. Spanning 1,346 square feet, the open floor plan showcases a modern grey color palette, creating an inviting ambiance throughout. Step into the kitchen, where sleek stainless steel appliances and light wood cabinets elevate your culinary experience. The master bathroom features a convenient walk-in shower, while the second bathroom offers a relaxing tub. An oversized utility room includes a handy utility sink and tenants need to supply their own washer and dryer. Outdoors, enjoy a private oasis with palm trees and a privacy fence, perfect for leisurely afternoons. The property boasts a one-car attached garage and an oversized driveway, providing ample parking space. Central air conditioning, a newer energy-efficient AC unit, and energy star windows promise to keep your energy bills low, ensuring comfort year-round. Located near Sarasota and Venice, this home is perfect for those who love outdoor activities, with easy access to Oscar Scherer State Park and the Legacy Trail. Pet-friendly living with conditions applies. Don't miss this opportunity—schedule your showing today! Note that tenants are responsible for utilities and a monthly lawn fee of $80.
#A4668434

OSPREY

163 PENNSYLVANIA AVENUE

3 Beds

2 Baths

1,346 Sq.Ft.

$2,400

MLS#: A4668434

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