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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

144

# of Listings

3

Avg # of Bedrooms

$406

Avg. $ / Sq.Ft.

$969,663

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

144 Properties Found. Page 6 of 10.

Location, Location, Location! Nestled West of the Trail in the heart of Osprey, this beautifully updated 3-bedroom, 2-bathroom plus den ranch home is a rare find—just steps from Sarasota Bay.
Surrounded by majestic oak trees and lush tropical landscaping, this spacious private lot comes with no HOA or CDD restrictions. Inside, you’ll love the open-concept layout, stylish durable flooring, and an updated kitchen with granite countertops, solid wood cabinetry, and stainless steel appliances. Both bathrooms have been tastefully refreshed with high-end finishes, making this home truly move-in ready.
Enjoy the ultimate Florida lifestyle with the Main Street fishing pier and Spanish Pointe Marina within walking distance. Oscar Scherer State Park, Bay Preserve at Osprey, and Historic Spanish Point are also nearby, and just a short drive brings you to Casey Key, Nokomis Beach, and world-famous Siesta Key. Top-rated Pine View School for the Gifted is also close by.
The large backyard provides plenty of space for entertaining, relaxing, or future customization. Whether you’re searching for a full-time residence, vacation retreat, or income-producing rental, this property checks all the boxes. Don’t miss this rare opportunity—schedule your private showing today and start living the coastal Osprey lifestyle.

OSPREY

51 WEBB STREET

3 Beds

2 Baths

3,046 Sq.Ft.

$614,000

MLS#: A4644363

#A4656074

OSPREY

4428 CONCHFISH LANE

4 Beds

2 Baths

2,657 Sq.Ft.

$599,000

MLS#: A4656074

$15,000 SELLER CONTRIBUTION! With a full price offer, you can use this money for a mortgage rate reduction or your costs. Touch-ups are in process so if you hurry, you may have time to make requests that make it perfect for you!

Rare opportunity to own one of the least expensive maintenance-free homes in a top-tier area and a renown, upscale community. Beautiful and quiet, yet 'everything' is minutes away, including the #1 rated grade school in FL, shopping, restaurants, medical facilities, beaches, restaurants, public boat launches, golf, parks, the Legacy trail and more.

Set back on a quiet street, on a beautifully landscaped, oversized lot with a preserve as the backdrop, this well maintained, light-filled residence offers a rare combination of elegance, security, privacy, efficiency, value, and lifestyle. The open floor plan features double tray ceilings, crown molding, and built-ins that create a comfortable, sophisticated atmosphere. Seamless indoor outdoor living, with 15 feet of sliding glass doors opening onto a covered patio and lanai. Enjoy nature views and stunning sunsets that are visible throughout the living area. Step through the stylish entryway and you're greeted by sunlight flooding in through custom-made plantation shutters. Large diagonal tile floors flow throughout the main living areas while cherry hardwood flooring adds elegance to the bedrooms and den.

The open kitchen features expansive Corian countertops and plenty of wood cabinets for storage. There are two breakfast bars and newer high-quality appliances - all, except the Bosch dishwasher, have been replaced in the last few years. The kitchen has an RO drinking water system, and the whole home provides bottle-quality water with a Kinetico Water Softener, Activated Carbon Water filtration, and a UV light system. The dining area’s bump-out design streams sunlight into the dining and kitchen areas. The master suite is a tranquil retreat, featuring a bump-out with bay windows and glass sliders to the lanai and 2 walk-in closets The ensuite bathroom has a large walk-in shower, soaking tub, and a dual sink vanity. The 2nd bedroom also has bay windows, so the room is bright with plenty of closet space, and there is a full bath just outside the bedroom door. The spacious home office features a decorative archway and dual sliding pocket doors - it could easily be converted to a nursery or 3rd bedroom.

Save money with your own private irrigation well and a new 6 zone Irrigation Controller. Landscaping care is provided for only $114/mo through the Woodlands HOA. The entire HVAC (Heat & AC) unit, including a UV light to prevent bacterial growth, was replaced 4/26/22. It has been regularly maintained with a service contract. The 50-gallon electric dual element (for quick heating) water heater was replaced 2/20/23. The oversized 2 car garage features an extra refrigerator/freezer, large utility sink, wall cabinets, and pull-down stairs with plywood flooring overhead provides additional attic storage.

Located between Sarasota and Venice, Rivendell offers a beautifully maintained neighborhood, designed to embrace the Florida lifestyle on close to 400 acres of parks, lakes and nature trails. Nature enthusiasts will also appreciate the close proximity to a number of recreational areas, including Oscar Scherer State Park, Myakka River State Park, Bay Street Dog Park, the Legacy Trail system, and numerous other parks for kayaking, biking, and hiking.

OSPREY

827 PLACID LAKE DRIVE

2 Beds

2 Baths

2,662 Sq.Ft.

$574,700

MLS#: TB8412007

One or more photo(s) has been virtually staged. WELCOME HOME!! THERE HAS BEEN NO FLOODING OR DAMAGE FROM RECENT STORMS!! RECENTLY APPRAISED at $560,000!! This is a Beautiful and Spacious 4 bed/2 bath Home in the Community of Bay Oaks Estates. It is just a Short Drive to 3 different Gorgeous Beaches including Nokomis Beach, Venice Beach and the World Famous Siesta Key! Easy Access to Tamiami Trail and I-75, Just Minutes away from Major Shopping Areas, Restaurants, City Parks, and The Popular Legacy Trail (biking/walking trail). When you walk in the front door you are greeted by a Large Living Area with High Ceilings. The Sliding Glass Doors lead you out to a Large 10x26 ft Covered and Screened Lanai with a Fully Fenced Back Yard that looks into a Heavily Wooded Preserve for Privacy. There are Tile Floors throughout the Entire House. The Master Suite has a Large Shower and Separate Garden Tub for Soaking your Cares Away. The Kitchen has Newer Stainless Steel Appliances from 2020 and lots of Counter Space. ROOF (2016). AC (2022). WATER HEATER (2020). NEW PAINT on the Interior. Whole House Water Filtration System installed by Water World in September 2023 The filter doesn’t need to be changed for 10 years! The House was RE-PLUMBED in 2016! The Laundry Room is inside under AC and has it's own Wash Sink. This Home is Perfect for Entertaining Guests. There is NO CDD and a LOW HOA FEE of only $270 PER YEAR. Bay Oaks is a Small, Quiet, Well Maintained Community where homes Rarely come available. It's Truly a Hidden Gem located in the Highly Desirable Osprey Area. Make an appointment to see it Today!

OSPREY

813 OAK POND DRIVE

4 Beds

2 Baths

2,675 Sq.Ft.

$560,000

MLS#: A4656967

#A4662424

OSPREY

455 N SHORE DRIVE

2 Beds

2 Baths

1,976 Sq.Ft.

$559,000

MLS#: A4662424

**Seller is motivated**Welcome to Bay Oaks Estates. This 3-bedroom 2 bath plus den is a classic Florida home featuring a pool with mosaic inspired ocean theme. And with no one behind you and no houses in front offers plenty of privacy. Oh, I almost forgot this home offers a wood burning fire place for those couple of cold nights a year, lol. New roof September 2022 newer water heater. This secluded community is only ten minutes to Siesta Key Beach or Nokomis Beach. You are very close to the Legacy Trail that is perfect for biking, walking and jogging. Also close to shopping and a wide verity of restaurants. If you are looking for a spacious pool home in a quiet secluded neighborhood look no more, you have found your forever home.

OSPREY

566 OAK BAY DRIVE

3 Beds

2 Baths

3,315 Sq.Ft.

$530,000

MLS#: A4632796

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!

OSPREY

1363 NEW FOREST LANE

2 Beds

2 Baths

2,307 Sq.Ft.

$499,000

MLS#: A4648690

Boating Community, Bay Acres! RV and Boat Parking pad 42'x16' with electric hook-up, and Huge 25'x12' extra Building! 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. 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.

OSPREY

519 BAYVIEW AVENUE

3 Beds

2 Baths

2,357 Sq.Ft.

$495,000

MLS#: A4649083

One or more photo(s) has been virtually staged. SELLER WILL CONSIDER LEASE PURCHASE. Try it before you buy it. Price reflects the need to update property interior. With expected ARV (after repair value) of +/- $600k, $91 per square foot under the most recent sale in the neighborhood, and less than a mile from the beach this is a great opportunity to find your Florida getaway. 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.

OSPREY

264 WOODS POINT ROAD

2 Beds

3 Baths

3,694 Sq.Ft.

$485,000

MLS#: A4625066

Boater's Paradise! 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 overlooking the bay, 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. A NEW DOCK with boat slips is currently being built.
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 (boat slips are available). 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 directly on Little Sarasota Bay, residents enjoy the highly sought-after Osprey location close to Siesta Key and Sarasota’s rich cultural attractions. Casey Key beach is only three miles away. Highly-rated medical facilities, major airports, and shopping destinations are within close driving distance. You have arrived at your final destination.

OSPREY

780 SARABAY ROAD 16

2 Beds

2 Baths

1,974 Sq.Ft.

$479,900

MLS#: TB8402328

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!

OSPREY

7303 JESSIE HARBOR DRIVE 7303

3 Beds

2 Baths

2,163 Sq.Ft.

$474,900

MLS#: D6142543

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!

OSPREY

352 GLENWOOD AVE

3 Beds

2 Baths

1,616 Sq.Ft.

$444,000

MLS#: N6138982

**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!

OSPREY

2251 JESSIE HARBOR DRIVE 2101

2 Beds

2 Baths

1,895 Sq.Ft.

$409,900

MLS#: A4631433

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.

OSPREY

401 N POINT ROAD 301

3 Beds

3 Baths

2,837 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!

OSPREY

436 S TAMIAMI TRAIL C4

None Beds

None Baths

1,272 Sq.Ft.

$395,000

MLS#: A4648348

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