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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

140

# of Listings

3

Avg # of Bedrooms

$420

Avg. $ / Sq.Ft.

$955,580

Med. List Price

Browse Osprey Real Estate Listings

$250,000 - $500,000

13 Properties Found. Page 1 of 1.

The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in Florida, or for anyone looking to downsize without sacrificing comfort or style. Residents enjoy the best of the Florida lifestyle, with close proximity to beautiful beaches-just 2 stoplights away. Additionally, the community is near parks, arts venues, shopping, and restaurants, making it perfect for both active living and peaceful retreat. This home has been thoughtfully updated with new porcelain "wood-look" tile throughout most of the living space, a renovated guest bathroom featuring a walk-in shower, fresh interior paint, and a new roof installed in 2021. The neighborhood is located in one of Sarasota County's top school districts, with Pine View School just a few minutes away. Just a short walk up the street, the community clubhouse offers a generously sized pool, perfect for swimming and social gatherings. Whether you're seeking tranquil relaxation or active outdoor adventures, this exceptional property and community provide the perfect balance.
Notice- Some photos of the property have been Virtually Staged.

OSPREY

508 MEADOW SWEET CIRCLE

2 Beds

2 Baths

2,175 Sq.Ft.

$499,900

MLS#: A4664579

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

Value Property in a Great Coastal Location. Perfect for a Boating Community in Sarasota, Bay Acres quick boating to Siesta Key, Casey Key, Nokomis Beach and more! 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

Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating and waterfront lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless steel appliances—all completed in 2022. Yard was completely fenced in 2024. With ample square footage, there’s even potential to add a third bedroom, offering flexibility for your needs. All major systems have already been taken care of, this home is waiting for your personal touch. The oversized garage with over 500 SF has a set of sliding doors leading to the backyard and covered side-yard. Large 15,500 SF of land there is ample space to add a pool. This home has a split bedroom layout and 2 bathrooms (one en-suite; other could be made en-suite). Not located in a high risk flood zone. The Bay Acres community features a private waterfront park on a protected bay with dockage for boats up to 22 feet, a kayak launch, and storage for kayaks and paddle-boards. There’s also a shaded picnic area for relaxing or entertaining. Boaters will love the direct access to the water from the 12-slip community boat basin, with slips available by waitlist. For larger vessels, Blackburn Point Park Boat Ramp is just 1.5 miles away. Located just minutes from Casey Key, Siesta Key, and the A+ rated Pine View School, this property is ideal for boaters, beachgoers, and families alike. Nearby attractions include Oscar Scherer State Park, Selby’s Historic Spanish Point, and The Legacy Trail, while Downtown Sarasota and Venice offer plenty of shopping, dining, and entertainment options. Bay Acres is a non-deed-restricted neighborhood, giving you the freedom to park your boat, trailer, or RV without the hassle of HOA restrictions. All the hard work has been done—now it’s time to make this your own piece of paradise.

OSPREY

32 BAY AVENUE

2 Beds

2 Baths

2,739 Sq.Ft.

$495,000

MLS#: N6140978

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

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.

OSPREY

51 N TAMIAMI TRAIL

None Beds

None Baths

0.24 acres

$395,000

MLS#: A4638654

One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and entertaining. Elegant tray ceilings, crown molding, and 9-foot ceilings enhance the first floor living space. The flooring is a beautiful wood look tile and LVP throughout the home. Upstairs, you’ll find both bedrooms, including the primary suite with a walk-in closet. As an extra bonus, there is a two-car garage. Enjoy the community pool, or your own private hot tub. Venture out to nearby Gulf beaches, shopping, dining, Oscar Sherer State Park and the Legacy Trail. Whether you’re looking for a year-round residence or a seasonal retreat, this home is the perfect fit. Don’t miss this opportunity—schedule your showing today!

OSPREY

1801 HIGHLAND ROAD

2 Beds

2 Baths

2,125 Sq.Ft.

$350,000

MLS#: N6140508

Location, Lifestyle, and Peace of Mind — All in One!

Welcome home to this beautifully appointed 3-bedroom, 2-bath end-unit condo in one of the area's most desirable pet-friendly gated communities. Built with lasting quality in mind, this home offers solid block stucco construction paired with hurricane-impact windows and doors — giving you the comfort of security and the ease of low maintenance living.

Step inside and be greeted by an inviting open-concept floor plan designed for modern living. Soaring ceilings, abundant natural light, and a thoughtful split-bedroom layout create the perfect blend of spaciousness and privacy. The heart of the home — a stunning chef’s kitchen — features granite countertops, stainless steel appliances, and a center island with seating, making it ideal for everyday meals or casual entertaining.

Enjoy the convenience of an in-unit laundry room and the luxury of a primary suite retreat complete with a walk-in closet and a spa-inspired en-suite bath with dual vanities. Added bonuses include a whole-house water softener and a covered, screened patio overlooking lush gardens and swaying palm trees — your personal oasis.

And for those with little ones or furry friends? The spacious side yard offers the perfect spot for play and relaxation.

Resort-style living is yours with amenities including a heated pool, fitness center, and clubhouse. The attached garage with the longest driveway in the community, easily accommodating up to 4 cars, plus extra guest parking conveniently located right across the street. Even better — Bay Street Park, complete with a dog park and playground, is just steps away from the entrance.

Unbeatable Sarasota/Venice Location!
Ideally located between Sarasota and Venice, with easy access to US 41, I-75, Siesta Key, Nokomis Beach (just 6.5 miles!), the Legacy Trail, and Oscar Scherer State Park. Top-rated schools, golf courses, marinas, shopping, dining, and healthcare are all close by.

With a low $460 monthly fee that covers exterior maintenance, insurance, roof, landscaping, gates, water, and amenities — and NO flood insurance required — this home is a smart choice for full-time living, a seasonal escape, or a savvy investment.

Don’t miss your chance — schedule your private tour today!

OSPREY

116 NAVIGATION CIRCLE 106

3 Beds

2 Baths

1,511 Sq.Ft.

$325,000

MLS#: A4658738

Charming 2 Bedroom 2 Bath corner end unit( which provides extra natural light) condominium with attached 1 car Garage. Open floor plan, Kitchen features granite counter tops and stainless steel appliances, master bedroom suite has walk-in closet private bath with double vanity. Dining Room opens to enclosed balcony. Quality construction concrete block building with impact resistant glass windows, tile roof,and paver brick driveway. Bay Street Village is a Gated maintenance free complex featuring a Resort style Swimming Pool , fitness room, and Clubhouse This pet friendly complex is located across the street from Osprey Dog Park and easy access to the Legacy Trail great for biking, jogging, and leisurely walks. Fantastic location near shopping , dining, Oscar Scherer Park, and just a short drive to Siesta Key and Nokomis Beaches and A+ Pineview School is just 1 Minute away. A Great Place to spend the Season or a Lifetime. Welcome Home!!!

OSPREY

232 EXPLORER DRIVE 15

2 Beds

2 Baths

1,219 Sq.Ft.

$299,500

MLS#: A4648458

#T3541882

OSPREY

758 PINE RUN DRIVE 758

2 Beds

2 Baths

1,184 Sq.Ft.

$250,400

MLS#: T3541882

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