Sarasota's Premier Homes
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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.
$946,311
Med. List Price

Browse Osprey Real Estate Listings

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Over $5M

23 Properties Found. Page 1 of 2.

Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay.  This spacious 2-bedroom, 2-bath villa features a versatile bonus room—perfect for a home office, den, or even a guest bedroom. Inside, you'll find a thoughtfully updated interior with a renovated kitchen featuring raised panel maple cabinetry and granite countertops, The vaulted-ceiling living room offers tranquil lake views, with many evenings capped by stunning sunsets over the Bay. There is a 2 car garage not often seen in villas/condos. Outside, a courtyard with a hot tub and  plantings invites outdoor relaxation and entertaining and expands the living space. Community amenities include a heated bayside swimming pool, tennis court, a fishing pier, kayak launch, and dockage for 10 boats—complete with electric and water—available to residents at no cost. Enjoy carefree coastal living with maintenance-free grounds and an all-inclusive HOA that covers insurance, roof and exterior maintenance, landscaping, roads, pool and tennis facilities, docks, cable TV, high-speed internet, water, trash and sewer. Located close to the beach, shopping & restaurants as well as Pine View School
#TB8402328

OSPREY

780 SARABAY ROAD 16

2 Beds

2 Baths

1,574 Sq.Ft.

$499,900

MLS#: TB8402328

Live the Sarasota Coastal Lifestyle in Bay Acres – Boating Community! Nestled in the desirable waterfront neighborhood of Bay Acres, this charming 3-bedroom, 2-bath with extra Bonus Florida room and 2 car garage home offers a rare combination of coastal convenience, spacious living, and modern updates. Perfect for boating and RV enthusiasts, the property includes a 42' x 16' parking pad with electric hookup, a/c-equipped workshop and storage shed (25' x 12'), and community boat docks (2 now available first come, first served for a low annual fee), plus a kayak launch just moments away. Enjoy peace of mind with a newer roof (2022) and hurricane shutters, all located in flood zone X (no flood insurance required). Inside, the home is filled with natural light and character—featuring cork and laminate wood flooring, custom wood built-ins, an electric fireplace, and a well-equipped kitchen with modern appliances and generous counter space. The flexible floorplan includes a large Florida room ideal for entertaining or relaxing in the sunshine. The lushly landscaped yard provides a private and serene setting, while the covered front porch is the perfect place to enjoy morning coffee and the quiet coastal breeze. Whether you're looking for a full-time residence or a vacation retreat, this home delivers on space, storage, and lifestyle in one of Sarasota’s best-kept boating neighborhoods.
#A4649083

OSPREY

519 BAYVIEW AVENUE

3 Beds

2 Baths

1,885 Sq.Ft.

$499,000

MLS#: A4649083

One or more photo(s) has been virtually staged. SELLER WILL CONSIDER A LEASE PURCHASE. Try it before you buy it. Experience maintenance free Florida living, just a short walk, bike or drive to Casey Key in this large villa situated in the rarely available neighborhood of Blackburn Point Woods. The home greets visitors with a large welcoming paver patio providing a place to relax and greet your neighbors in this close-knit community. Entering the home, you will be find an expansive space ready for entertaining. Natural light abounds throughout, aided by the home’s soaring cathedral ceilings allowing you to enjoy a favorite book while enjoying nature in the preserve showcased through the enclosed lanai. The kitchen abounds with counter and cabinet space including a breakfast area overlooking the front patio. The main bedroom features an en-suite bath, preserve views and access to the lanai. A second bath and newly floored den complete the ground floor features. A loft overlooking the first floor, a second bedroom with an en-suite bath and separate office/storage room provides plenty of space for easy living. This home is located in one of the most desirable communities in Osprey. You are less than one mile from the beach, Blackburn point with its marina and boat launch, Casey Key Fish House, Deep Lagoon Seafood, Publix is just around the corner. Great healthcare is available at the new Sarasota Memorial Hospital in Venice. Easy access to I-75 can get you to 5 airports, extended shopping and more. Don’t let this one get away.
#A4625066

OSPREY

264 WOODS POINT ROAD

2 Beds

3 Baths

2,837 Sq.Ft.

$485,000

MLS#: A4625066

Discover this hidden gem in the sought-after waterfront community in Bay Acres, positioned West of the Trail with direct access to the Intracoastal Waterway situated on .037 acres that is completely fenced in for privacy! This beautifully renovated home has 3 spacious bedrooms and 2 bathrooms across 1,904 sqft, offering a split bedroom floor plan for maximum privacy. The primary suite features double walk-in closets and a luxurious en suite bathroom with his and her sinks and a walk in shower. Enjoy the Florida lifestyle on the large, oversized screened-in lanai or entertain guests easily with double doors that create a seamless indoor/outdoor flow. The property is completely fenced in and includes a 10 x 36 concrete pad, perfect for your RV, boat, or conversion to a shuffleboard or bocce court. The home offers convenient boat access via the community dock, and an optional HOA for just $75 annually. Additional highlights include a central vacuum system, built-in shelving and storage in the garage, an electric car charger, newer appliances, alarm and irrigation systems, a freshly painted walkway and lanai, and a dedicated dining space. Located in the desirable Pine View School District, with quick access to Highway 41, beaches, shopping, and restaurants in Nokomis, Venice, and Siesta Key. Don’t miss your chance to own this exceptional home with direct access to the intracoastal waterway. Call to schedule your appointment today.
#N6139582

OSPREY

26 BAY ACRES AVENUE

3 Beds

2 Baths

1,904 Sq.Ft.

$479,000

MLS#: N6139582

Welcome to this beautifully maintained Sorrento Shores pool home, exuding timeless Mediterranean charm. Built in 1988, this residence offers a warm, inviting atmosphere with classic architectural details such as a tile roof, stucco exterior, and arched entryways. Inside, you'll find a spacious and functional layout ideal for both everyday living and entertaining. The sunlit living areas feature high ceilings, decorative niches, and tile flooring. The well-appointed kitchen includes ample cabinetry, a breakfast bar, and views of the backyard oasis. The primary suite boasts direct access to the patio, a walk-in closet, and an en-suite bath with dual sinks and a soaking tub. Two additional bedrooms provide comfort and flexibility for family, guests, or a home office. Upgrades include new tile roof 2013, new AC 2018, entire repipe 2007. Step outside to your private backyard retreat, where a sparkling pool, lanai, and mature landscaping create the perfect space for relaxing or hosting gatherings year-round. Plenty of room to expand landscaping and the gardening hobbyist. Located in a quiet, established neighborhood, this home combines classic style with practical updates and pride of ownership. Don’t miss your opportunity to own this Mediterranean gem! Close to Sarasota and Venice, with plenty of shopping right on Rt. 41, Tamiami Trail. Intracoastal waterway at end of Sorrento Dr.
#A4653185

OSPREY

321 SORRENTO DRIVE

3 Beds

2 Baths

1,541 Sq.Ft.

$475,000

MLS#: A4653185

PENTHOUSE CONDO IN WATERFRONT COMMUNITY! Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for soaking up the Florida sunshine and enjoying great views. The gourmet kitchen is a chef’s dream, offering granite countertops, wood cabinetry, stainless steel appliances, and a cozy eat-in area for casual dining. The expansive master suite boasts a private balcony, two walk-in closets, double vanities, a soaking tub, and a separate shower for ultimate relaxation. Additional highlights include a wet bar for entertaining and three separate balconies for outdoor living. Enjoy resort-style amenities such as tennis courts, pickleball, shuffleboard, a heated pool, clubhouse, walking paths, a workout facility, and a convenient kayak launch for endless waterfront adventures. Bring your own boat and take advantage of your separately available assigned boat dock area! When you’re ready to explore, you’ll find yourself just 10 minutes from several Gulf Coast beaches, thousands of acres of parks and preserves, and world-class shopping, dining, and fishing. Quick connections to Sarasota’s vibrant arts scene, the new Mote Marine Aquarium, Spanish Point, the Legacy Trail, and Oscar Scherer State Park are all just minutes away. All of this and you will just be 5 minutes from I-75 where the rest of the world awaits you. Take the elevator to your nearby 2 assigned parking spots under the building. Don’t miss your chance to own this exceptional penthouse—schedule your private showing today!
#D6142543

OSPREY

7303 JESSIE HARBOR DRIVE 7303

3 Beds

2 Baths

1,883 Sq.Ft.

$474,900

MLS#: D6142543

**1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious Owner’s Suite boasts multiple walk-in closets, dual vanities, soaking tub and custom tiled shower. Tile Flooring Throughout. Enjoy the serene and natural surroundings from your sprawling and screened lanai which is accessible from multiple rooms via sliding doors. This Secure and Gated Community offers the ultimate Florida Lifestyle! Amenities include Community Pool, Tennis and Pickleball Courts, Clubhouse with Fitness Center, Boat Dock (subject to availability), Kayak launch and storage, Gazebo with BBQ, etc. Blackburn Harbor is ideally situated in Osprey between Sarasota and Venice and is just minutes minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer!
#A4631433

OSPREY

2251 JESSIE HARBOR DRIVE 2101

2 Beds

2 Baths

1,400 Sq.Ft.

$449,900

MLS#: A4631433

Beautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions Welcome to this immaculate 3-bedroom, 2-bath home, newly built in 2021 and perfectly located just minutes from top-rated beaches, shopping, dining, and entertainment. This move-in-ready home offers a clean, modern design with a spacious open floor plan that’s ideal for both relaxing and entertaining. Enjoy cooking in the stylish open kitchen, complete with granite countertops and ample cabinet space. Luxury vinyl flooring runs throughout the home, adding durability and a sleek, contemporary feel. With no HOA, CDD, or deed restrictions, this property provides true freedom and flexibility—bring your boat, RV, or other recreational vehicles with ease. The generous lot offers plenty of room for parking and outdoor enjoyment. Don’t miss this rare opportunity to own a centrally located, low-maintenance home in a highly desirable area!
#N6138982

OSPREY

352 GLENWOOD AVE

3 Beds

2 Baths

1,300 Sq.Ft.

$444,000

MLS#: N6138982

One or more photo(s) has been virtually staged. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating touches on it and make it uniquely your own. Check out the virtually staged photos to help you imagine what you could do with this great floor plan. This condo offers space for year-round living, or to use as a welcoming winter retreat, with room for family and friends to visit. Wouldn’t it be lovely to sit on the private terrace and listen to the birds sing as the sun sets on another perfect day? The building is a short walk to the Meridian residents-only fitness room, spa and heated pool. The Oaks Club has two championship golf courses, 12 HAR TRU tennis courts (4 lighted), croquet and pickleball courts, a state-of-the art fitness center, junior Olympic community pool, and offers a wide variety of dining and recreational options, and social activities. When you open the door to your new home here, you have opened the door to the best in Gulf Coast country club living. Membership in The Oaks Club is required with homeownership.
#A4603773

OSPREY

401 N POINT ROAD 301

3 Beds

3 Baths

2,594 Sq.Ft.

$399,900

MLS#: A4603773

*Open to discussing concessions with any reasonable offer* Sophisticated Office Condo in Prime Osprey Location – Act Now! Seize the opportunity to elevate your business in the prestigious Gulf Coast community of Osprey, FL. Positioned strategically on Tamiami Trail (US-41) between the cultural heart of Sarasota and the pristine beaches of Venice, this exceptional office condo places you in the epicenter of business and leisure. With seamless access to major highways, airports, and ports, your company will enjoy unmatched connectivity, opening doors to endless growth and networking potential. Osprey, nestled in the thriving Sarasota County, is renowned for its dynamic business ecosystem—fostering innovation, entrepreneurship, and economic vitality. This is more than just a location; it’s a chance to become part of a forward-thinking community dedicated to success. Surrounded by lush landscapes, serene waterways, and the nearby Gulf of Mexico, your team will thrive in an inspiring and sophisticated environment. Key Features: • Reception/Waiting Room that exudes professionalism • Spacious cubicles and 2 private offices for focused productivity • 1 Executive Conference Room, ideal for high-level meetings • Convenient kitchenette/breakroom for employee comfort • 1 In-suite restrooms for added convenience • Ample parking for your team and visitors • Quarterly HOA dues: $945 Don’t miss out on the chance to secure this stunning office space in one of the region’s most sought-after locations. The demand for spaces like this is high, and opportunities this exceptional won’t last long. Invest in your business’s future today—before it's gone!
#A4648348

OSPREY

436 S TAMIAMI TRAIL C4

None Beds

None Baths

1,272 Sq.Ft.

$395,000

MLS#: A4648348

Clean, well built out and maintained office condo on US41 in Osprey. The unit features bright lighting, private offices, a reception area, and a conference room. Condo property is clean and presents a professional appearance with lots of on site parking.
#A4595920

OSPREY

430 S TAMIAMI TRAIL D1

None Beds

None Baths

1,272 Sq.Ft.

$395,000

MLS#: A4595920

Excellent location! Corner lot Zoned CG (Commercial General) with 117 feet of frontage on US 41 in Osprey, just north of Bay Street. Prime area of growth in Sarasota County next to Calico Corners, Bay St., Spanish Point restaurants, Sarasota crew and Super Walmart. Perfect opportunity for your own business or investment. Great accessibility on 3 sides for ingress and egress (US 41, Shumard, and Columbia). 10,469 sq ft: 117 feet on US 41, 116 feet on Columbia, 92.5 feet on Shumard, and 88 feet on North lot line. Vacant lot: no buildings on the property. Plat map and survey on attachments. There is a bus stop on the sidewalk on 41. Listing agent is owner.
#A4638654

OSPREY

51 N TAMIAMI TRAIL

None Beds

None Baths

0.24 acres

$395,000

MLS#: A4638654

Enjoy this Key West-style townhome in Towns-End Shores-maintenance-free living at its best! Beautifully upgraded with porcelain wood look tile flooring, crown molding and 9-foot ceilings, this 2 bed/2 bath townhome features granite countertops, wood cabinetry, an enclosed Florida room, and a spacious 2-car garage. Enjoy a tropical private backyard oasis and community pool amenities. Original metal roof, A/C 2010, Hot Water Heater 2013 This home is ideally located just minutes from pristine Gulf beaches, dining, boutiques, shopping, airports, Shoreland Park, The Legacy Trail, and Oscar Scherer State Park. Perfect for outdoor enthusiasts, this townhome is a sanctuary for those who seek beauty, tranquility, and a premier Sarasota County lifestyle!
#A4656484

OSPREY

1801 HIGHLAND ROAD

2 Beds

2 Baths

1,165 Sq.Ft.

$380,000

MLS#: A4656484

Charming 3-bedroom, 2-bath bungalow with no HOA or deed restrictions—perfect for boaters, RV owners, or anyone seeking freedom and flexibility. Situated in a prime location close to beaches, waterfront dining, the Legacy Trail, Selby Botanical Gardens, Pine View school is 1 mile away (this high school is ranked numbr 18 nationwide and number 1 in Florida), shopping (Walmart Super Center) and Oscar Scherer Park. A kayak launch is conveniently located across the street, and a public boat ramp is just 3 miles away. This well-maintained home features a spacious under-roof lanai added in 2020, newer septic system (2022), newer AC (2023 with 10 year warranty) and a roof replaced in 2016. The lush yard is a tropical oasis with mature fruit trees including lemon, dragon fruit, sapodilla, and loquat. Don’t miss this opportunity to enjoy Florida living at its best with space to store your toys and easy access to the area's top attractions.
#A4647247

OSPREY

240 PATTERSON AVENUE

3 Beds

2 Baths

1,360 Sq.Ft.

$365,000

MLS#: A4647247

Escape from the hustle and bustle of the real world to the charms of Hidden Bay. Located on 12 beautiful acres on Little Sarasota Bay, this gated community offers waterfront play and relaxation. Spend your perfect day at the amenity rich community clubhouse/pool or kayaking on Intracoastal waters. This lovely two-bedroom, two-bath home is roomy and bright, offering a den/office along with a screened in back porch that overlooks the wonderful sight of native Floridian landscaping. The natural light flows from room to room in more than 1,500 square feet of living space. The split-floorplan is thoughtfully arranged with the guest suite having direct access to the 2nd bathroom. Home includes new luxury vinyl flooring and stainless steel appliances. Additional community amenities include a social-rich clubhouse, tennis and pickleball courts, kayak racks/launch and a renovated fitness center. HOA fees include the maintenance of the roof and exterior of the building along with the water, basic cable and internet. Hidden Bay offers everything you need for a Florida lifestyle while residing close to award-winning beaches, Historic Spanish Pointe, Oscar Scherer State Park and The Legacy Trail. Enjoy all of the culture and arts that Sarasota has to offer by making this home yours!
#A4628192

OSPREY

294 HIDDEN BAY DRIVE 203

2 Beds

2 Baths

1,568 Sq.Ft.

$324,900

MLS#: A4628192

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