One of the most popular communities provided by {{page_data.agentName}}

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

146

# of Listings

3

Avg # of Bedrooms

$404

Avg. $ / Sq.Ft.

$981,910

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

146 Properties Found. Page 10 of 10.

#A4658758

OSPREY

280 HIDDEN BAY DRIVE E 203

3 Beds

2 Baths

2,236 Sq.Ft.

$4,200

MLS#: A4658758

Annual unfurnished single-family pool home available in Willowbend! Gorgeous Lee Wetherington-built three-bedroom, two-bath home located in the maintenance-free neighborhood of Willowbend in Osprey. The home features a gourmet kitchen with gas cooktop and double oven, 12-foot ceilings, plantation shutters, a solar-heated pool, and spacious lanai with lake view. Willowbend amenities include lawn maintenance, community pool/spa, fitness center, pickleball and high-speed internet/cable. The excellent location in Osprey puts you right in between Sarasota and Venice, close to beaches, the Legacy Trail, shopping, dining, Oscar Scherer State Park and Pine View School.

OSPREY

1279 THORNAPPLE DRIVE

3 Beds

2 Baths

2,968 Sq.Ft.

$4,000

MLS#: A4660535

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.

OSPREY

510 LATITUDE LANE

3 Beds

2 Baths

2,994 Sq.Ft.

$3,999

MLS#: A4657618

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.

OSPREY

5100 JESSIE HARBOR DRIVE 602

2 Beds

2 Baths

2,304 Sq.Ft.

$3,950

MLS#: N6139624

Now Available – Lease Option or Lease Purchase Opportunity in Willowbend! Flexible lease terms now offered:
Lease Option with option fee - OR - Lease Purchase with buyer commitment and possible rent credit.
Lease Option: Lease now with the option—but not the obligation—to purchase later. You are not obligated to buy, but the seller retains the option fee if you don’t. Lease Purchase: Lease now with a commitment to purchase the home within the lease term. Designed for serious buyers working toward closing. Buyer must close within 12 months or may forfeit rent credits and purchase rights. (Ask for the Example term sheet)

Live large in this 3,183 sq ft Lee Wetherington-built pool home with preserve and pond views.

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!

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.

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.

OSPREY

51 MAC EWEN DRIVE 1

1 Beds

1 Baths

623 Sq.Ft.

$2,500

MLS#: A4589608

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 by 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.

OSPREY

4214 FRONTIER LANE 102

2 Beds

2 Baths

2,034 Sq.Ft.

$2,400

MLS#: A4661663

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!

OSPREY

234 PATTERSON AVENUE

3 Beds

1 Baths

1,288 Sq.Ft.

$2,300

MLS#: A4660042

The unit is available for rent from August 1 ,2025.The minimum rental period is 2months. The monthly rent is $2200. 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.

OSPREY

184 EXPLORER DRIVE

2 Beds

2 Baths

1,450 Sq.Ft.

$2,200

MLS#: A4648720

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.

OSPREY

291 HIDDEN BAY DRIVE 201

2 Beds

2 Baths

1,960 Sq.Ft.

$1,800

MLS#: R4909551

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