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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
163
# of Listings
3
Avg # of Bedrooms
$463
Avg. $ / Sq.Ft.
$1,122,489
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

163 Properties Found. Page 11 of 11.

Price reduced
Welcome to your new spacious home in the beautiful waterfront neighborhood of Sorrento Shores. As you approach this three bedroom, three bath POOL house you will notice the quiet charm that this highly sought-after neighborhood provides. The streets are lined with tropical fruit trees, palms, and plants that create a tranquil atmosphere. The open concept, split floor plan, and wonderfully updated home provides plenty of room for entertaining guests or privacy to stop and relax after a long day. You will love the fact that the great room opens to the covered patio, deck, and blue waters of the in-ground pool and screened-in lanai. The outdoor entertaining space is fantastic and the pool was just refinished. In addition, brand new hurricane windows were just installed to make the space quiet and safe. This home is located a short bike ride or drive to Nokomis Beach. Sorrento Shores is ideally situated between Sarasota and Venice. This allows quick access (a fifteen minute drive) to six different gulf beaches and all that the gulf coast has to offer. It is only minutes from historic Venice Island which boasts shopping, restaurants, and breath-taking sunsets. SORRENTO SHORES ALSO HAS A DAY DOCK FOR RESIDENTS TO USE. LAWN CARE AND POOL CARE ARE BOTH INCLUDED IN THE RENT PRICE.
#A4665120

OSPREY

451 N SHORE DRIVE

3 Beds

3 Baths

2,503 Sq.Ft.

$3,800

MLS#: A4665120

*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

3,012 Sq.Ft.

$3,550

MLS#: A4667570

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. ~Utilites: Water/Sewer/Trash ~Pets: No, sorry. ~Available as a Seasonal: $6500 (Dec-Apr)
#N6139624

OSPREY

5100 JESSIE HARBOR DRIVE 602

2 Beds

2 Baths

2,304 Sq.Ft.

$3,500

MLS#: N6139624

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.

$3,000

MLS#: A4668291

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

2,307 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

2,154 Sq.Ft.

$2,995

MLS#: A4648193

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.

$2,500

MLS#: A4668434

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

Lovely 2 bed/2 bth well maintained townhouse with a 2 car garage Set in a private enclave in the desirable West of Trail Osprey location with a Community pool. Close to beaches, restaurants and shopping.
#O6342686

OSPREY

1817 HIGHLAND ROAD

2 Beds

2 Baths

1,145 Sq.Ft.

$2,395

MLS#: O6342686

Price reduced
Welcome to 234 Patterson Ave, a charming single-family home nestled in the heart of Osprey, Florida. This amazingly located residence offers 3 bedrooms, 1 and a half bathrooms, and 1,173 square feet of comfortable living space. The open-concept layout features vaulted ceilings and a NEW modern kitchen equipped with granite countertops, soft close drawers, a center island, and new Frigidaire stainless steel appliances. Recent renovations include updated flooring, a refreshed bathroom, and a fully fenced yard for added privacy. IMPACT WINOWS THROUGHOUT!! Enjoy outdoor living with both a side porch and a spacious rear deck—perfect for entertaining or relaxing in the Florida sunshine. The property sits on a 5,197 sq ft lot and includes central air conditioning and a separate laundry room. Located just minutes from world-renowned Gulf Coast beaches, this home blends comfort, style, and an unbeatable location. This home is located just south of Sarasota, just north of beautiful downtown Venice and minutes from the beaches! Your beach life is about to begin!
#A4660042

OSPREY

234 PATTERSON AVENUE

3 Beds

1 Baths

1,288 Sq.Ft.

$2,000

MLS#: A4660042

Stunning annual unfurnished 2 bed/2 bath ground floor condo located at Pine Run in Osprey, FL. Water, sewer/trash, lawn maintenance, washer/dryer, and pest control included. Available now for $2,000 a month. Application fee for each adult $50, association application fee of $50(10-day association approval process), $ 2,000 security deposit, and $100 administrative fee. 1 pet allowed (small to medium size) One-time non-refundable pet fee of $350. *Fico score over 600* Renters Insurance is required. Application is available on our website at aandrpropertymgmt.managebuilding.com This Beautiful community offers assigned parking, two heated swimming pools, pickleball courts, tennis courts, fitness center, and saunas. Offering close proximity to Oscar Scherer State Park, Legacy Trail, and the Gulf's stunning beaches. Shopping, dining, and cultural attractions in Venice and Sarasota are just a short drive away.
#A4664411

OSPREY

304 PINE RUN DRIVE 304

2 Beds

2 Baths

1,975 Sq.Ft.

$2,000

MLS#: A4664411

Pine Run 2-bedroom, 2-bath condo West of the Trail, offered for annual lease. Unit is located on 2nd floor with stairs. Tucked among mature trees, the home offers a peaceful retreat with a private deck and three balconies that let you enjoy the surrounding natural setting from multiple vantage points. Inside, you’ll find spacious rooms filled with natural light, high ceilings, soft colors, NEW interior paint in a neutral palette, and NEW carpet in the living room. The unit is exceptionally well kept and includes a carport plus two outdoor storage closets, along with refreshing cross-breezes thanks to windows on all four sides. Pine Run is known for its artistic and active community atmosphere and spans more than 20 acres of lush vegetation, offering two heated pools, tennis and pickleball courts, a clubhouse overlooking a wildlife-rich lagoon, walking paths, a brick fire pit area, kayak storage, saunas, and a fitness center. Its location is unmatched—West of the Trail and minutes from shopping, medical services, parks, beaches, Pine View School, and a variety of dining options. Small adult dogs (under 35 lbs) are welcome with a refundable pet deposit. First month’s rent, last month’s rent, and security deposit required. Stable income of at least 2.5× the monthly rent. Minimum credit score of 630+ (we review the full credit profile and consider the complete application).
#R4910248

OSPREY

137 WOODLAND PLACE

2 Beds

2 Baths

1,483 Sq.Ft.

$1,500

MLS#: R4910248

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