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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

145

# of Listings

3

Avg # of Bedrooms

$418

Avg. $ / Sq.Ft.

$964,578

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

145 Properties Found. Page 7 of 10.

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

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

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

LIMITED SUPPLY LEFT IN PINE RUN - MOTIVATED SELLER - Your Opportunity To Add Your Personal Touch! Charming Coastal Retreat in the Heart of Osprey Welcome to 304 Pine Run Dr., a beautifully architecturally designed property nestled in the sought-after Pine Run community in Osprey, FL. Surrounded by lush tropical landscaping and just minutes from the Gulf Coast’s pristine beaches, this residence offers the perfect blend of tranquility and convenience. Step inside to discover an open and airy floor plan with abundant natural light, high ceilings, and tasteful finishes throughout. The owner has made major updates to the back entertaining room by increasing square feet. They also used hurricane windows and sliders along with heavy duty installation in the walls and ceiling. It's the only unit in Pine Run that offers this floor plan. The spacious living area flows seamlessly into the kitchen and dining spaces, making it perfect for entertaining. Enjoy cooking in the updated kitchen, featuring stainless steel appliances, modern cabinetry, and ample counter space. The primary suite serves as a private retreat with a generously sized walk-in closet and an en-suite bathroom. Additional bedrooms provide plenty of space for guests or a home office. Step outside to your private atriums, where you can unwind and take in the serene surroundings of this nature-inspired community. Pine Run residents enjoy access to an array of amenities, including two heated sparkling pools, pickleball courts, tennis courts, a fitness center, Saunas and a clubhouse. This location is ideal for outdoor enthusiasts, offering 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. Whether you’re seeking a year-round residence or a seasonal getaway, this home offers an exceptional opportunity to embrace the coastal lifestyle. Don’t miss your chance—schedule your private showing today!

OSPREY

304 PINE RUN DRIVE

2 Beds

2 Baths

1,975 Sq.Ft.

$279,000

MLS#: A4636298

#T3541882

OSPREY

758 PINE RUN DRIVE 758

2 Beds

2 Baths

1,184 Sq.Ft.

$250,300

MLS#: T3541882

Hidden away in Osprey is the private oasis of Pine Run. You could not find a more natural setting and fantastic location, convenient to Sarasota, Venice and Gulf beaches. This immaculate, ground floor condo is being sold furnished so settling in will be easy. The updated kitchen with stainless appliances is large enough to incorporate dine-in eating, and a laundry closet with full size washer and dryer. A generously proportioned living/dining area leads to the private covered lanai with garden view. The master bedroom has a private en-suite bath and walk-in closet. Other outdoor spaces include a paved courtyard just off of the kitchen and a private interior courtyard with gazebo that can be accessed from the living room and master bedroom. Large sliders in every room allow lots of light in and you'll love the feel of sea breezes passing through when all are opened. Two exterior storage closets provide ample storage. Pine Run is a pet friendly haven for artists and the active; sitting on 20+ lushly vegetated acres, with 2 heated pools; clubhouse overlooking a lagoon teeming with wildlife; tennis; pickle ball; brick patio with fire pit; kayak storage; saunas and fitness room. The community's location is ideal: West of the Trail, near shopping/banking/medical services, parks, public beaches, nationally acclaimed Pine View School, and casual and fine dining. The Legacy Bike Trail and Blackburn Point Park with a kayak launch are minutes away and Nokomis Public Beach is a quick, convenient drive. The popular Casey Key Fish House & Tiki Bar and other waterfront dining, all within a short distance.

OSPREY

111 WOODLAND PLACE

2 Beds

2 Baths

1,474 Sq.Ft.

$245,000

MLS#: A4663760

Owner Financing is Available. Prime Land at 456 Washington Ave, Osprey, FL 34229 – A Rare Gem Near Historic Spanish Point & Selby Gardens.
Don’t miss out on this incredible opportunity to own a prime piece of land at 456 Washington Ave, located in the heart of Osprey, FL. Surrounded by natural beauty and rich history, this property is just moments from the renowned Historic Spanish Point and the tranquil beauty of Selby Gardens.

How this property stands out:

Low Taxes: Keep more money in your pocket with low property taxes, making this an affordable investment.
No HOA: Enjoy the freedom to design and build your dream home without any restrictive's rules or fees.
No CDD Fees: With no community development district fees, giving you more financial freedom in your new property.

Perfectly positioned near some of Osprey’s most treasured landmarks, this land offers you a unique lifestyle. Imagine living just minutes from the serene shores of Sarasota Bay, where you can explore the historic Spanish Point or enjoy peaceful afternoons at Selby Gardens. Plus, you're close to the Legacy Trail for biking and hiking, and a short drive to Sarasota’s beaches, dining, and shopping.

Whether you're an investor, builder, or homebuyer seeking the perfect place to bring your vision to life, this land offers endless possibilities. Don’t let this chance slip away—build your future in one of Florida’s most desirable and scenic locations!

Claim your slice of paradise now—this opportunity won’t last!

OSPREY

456 WASHINGTON AVENUE

None Beds

None Baths

0.13 acres

$239,999

MLS#: A4623594

New on site 3 days ago

Tranquil Coastal Living in Pine Run
244 Woodland Dr, Osprey, FL 34229

Tucked beneath a canopy of mature oaks and palms, this beautifully updated 2-bedroom, 2-bath condo captures the easy, natural rhythm of coastal Florida living. Nestled within the sought-after Pine Run community, it offers both peace and connection just minutes from the beaches of Casey Key, charming Venice, and downtown Sarasota.

Step inside to discover light-filled spaces, a warm neutral palette, and a welcoming open layout. The kitchen stands out with stainless-steel appliances, a stylish glass backsplash, and playful custom cabinetry that adds personality and character. A cozy breakfast nook sits beside a large window overlooking lush greenery, creating the perfect spot to start your day.

The spacious living and dining areas flow naturally toward a screened lanai with vaulted wood ceilings, where you can sip coffee in the morning or unwind at sunset to the sounds of nature. Both bedrooms are roomy and inviting, with the primary suite opening directly to the lanai for that indoor-outdoor lifestyle Florida is famous for.

Pine Run offers resort-style amenities in a natural, park-like setting two heated pools, tennis and pickleball courts, a fitness center, clubhouse, and kayak storage. With 20+ acres of native trees, walking trails, and tropical landscaping, this community feels worlds away yet sits moments from Tamiami Trail, dining, marinas, and the Gulf’s turquoise waters.

Highlights:
• 2 Bedrooms, 2 Bathrooms, 1,325 Sq Ft
• Open, light-filled interior with stylish kitchen and breakfast nook
• Vaulted, wood-ceiling lanai with peaceful treetop views
• Primary suite with private lanai access
• Full laundry, ample storage, and designated carport parking
• Low-maintenance living with exceptional amenities
• Minutes to Nokomis Beach, Casey Key, and downtown Sarasota

Live easy. Breathe deep. Welcome home to Pine Run.

OSPREY

244 WOODLAND DRIVE 244

2 Beds

2 Baths

1,483 Sq.Ft.

$225,000

MLS#: A4667419

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