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Osprey

One of the most popular communities provided by Michael Graf

Osprey

About Osprey

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.

One of the most popular communities provided by Michael Graf
163
# of Listings
3
Avg # of Bedrooms
$463
Avg. $ / Sq.Ft.
$1,122,489
Med. List Price

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163 Properties Found. Page 8 of 11.

Waterfront villa offering MAINTENANCE-FREE LIVING just minutes to the ICW with no bridges! This 2BR/2BA home features a 2024 10,000 lb BOAT LIFT with water & electric, new Trex decking and epoxy concrete, HURRICANE IMPACT WINDOWS/DOORS, and a ROOF from 2019. Inside, enjoy a 2024 TOTAL KITCHEN REMODEL with quartz counters, backsplash, NEW GE appliances, and OPEN FLOOR PLAN. Additional upgrades include UV light in air ducts, re-piped plumbing, new Levelor blinds, and screened front/back lanais with custom lighting and pavers. Community amenities include pool, cabana, and boat docks. Conveniently located near beaches, Legacy Trail, golf, state park, and downtown Venice & Sarasota—this villa is all about the Florida lifestyle! FLOOD INSURANCE POLICY IS TRANSFERABLE!
#N6141356

OSPREY

119 VILLA DRIVE

2 Beds

2 Baths

1,905 Sq.Ft.

$525,000

MLS#: N6141356

Price reduced
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 unit has a one car under building parking space. It 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

2,837 Sq.Ft.

$500,000

MLS#: A4603773

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!
#A4648690

OSPREY

1363 NEW FOREST LANE

2 Beds

2 Baths

2,307 Sq.Ft.

$499,000

MLS#: A4648690

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

2,163 Sq.Ft.

$474,900

MLS#: D6142543

Price reduced
PRICE IMPROVEMENT!! 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.
#A4664579

OSPREY

508 MEADOW SWEET CIRCLE

2 Beds

2 Baths

2,175 Sq.Ft.

$465,000

MLS#: A4664579

Price reduced
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 have 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.
#N6140978

OSPREY

32 BAY AVENUE

2 Beds

2 Baths

2,739 Sq.Ft.

$463,000

MLS#: N6140978

Price reduced
PRICE IMPROVEMENT!!... BOATER'S PARADISE!! SELLER WILL CREDIT BUYER $20,000 AT CLOSING. Fish off the Pier or sit & enjoy the sunsets! 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 an attached 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 and FISHING PIER with Complimentary 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. SELLER WILL CREDIT BUYER $20,000 AT CLOSING TO GO TOWARD THE CONDO/HOA FEES! Effectively reducing HOA fee by $555 for the first 3 years!!! Located directly on Little Sarasota Bay, residents enjoy the highly sought-after Osprey location close to Siesta Key and Sarasota’s rich cultural attractions. Nokomis beach is only a few miles away. Enjoy waterfront dinning at Casey Key Fish House, The Point and Deep Lagoon Oyster House. Highly-rated medical facilities, major airports, and shopping destinations are within close driving distance. You have arrived at your final destination.
#TB8402328

OSPREY

780 SARABAY ROAD 16

2 Beds

2 Baths

1,974 Sq.Ft.

$449,900

MLS#: TB8402328

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

1,616 Sq.Ft.

$444,000

MLS#: N6138982

PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches. Walking distance to Casey Key Mainland (Chef Rolfs), private community Shoreland Park & Oscar Scherer State Park. Minutes away from COSTCO, Publix, Target, Richard's, YMCA Potter Park, waterfront dining (Casey Key Fish House & Tiki bar - waterfront , Spanish Point restaurant & Tiki Bar. The townhouse is close to Laurel Rd and Sarasota Memorial Hospital. Property is managed by owner. Timely response to accommodate your needs. Summary of amenities: PARKING: 2-CAR TANDEM GARAGE HOA PRIVATE COMMUNITY 1 BLOCK FROM INTERCOASTAL SCREENED BALCONY CEILING FANS VAULTED CEILING CENTRAL AIR UPGRADED TALL CABINETS GRANITE COUNTERTOP STAINLESS STEEL APPLIANCES CONVECTION RANGE/OVEN/AIRFRYER MICROWAVE DISHWASHER IN-SINK DISPOSAL SMART REFRIGERATOR DINING ROOM & FAMILY ROOM MASTER BEDROOM WITH WALK-IN CLOSET MASTER BATH GUEST BEDROOM ADDITIONAL STORAGE IN LOWER FLOOR OR GARAGE AIR CONDITIONING WASHER/DRYER SPRINKLER SYSTEM COMMUNITY SWIMMING POOL WITH LOUNGE CHAIRS + USE OF CASEY KEY MAINLAND POOL WALK/BIKE TO TOP RATED PINEVIEW SCHOOL, WALLMART, POST OFFICE, LEGACY BIKE TRAIL CLOSE TO SIESTA KEY, NOKOMIS BEACH, VENICE BEACH, OSCAR SCHERER STATE PARK HUGE FURNISHED BONUS ROOM ON FIRST FLOOR OUTDOOR GRILL
#TB8443161

OSPREY

1811 HIGHLAND ROAD

2 Beds

2 Baths

1,725 Sq.Ft.

$443,000

MLS#: TB8443161

**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

1,895 Sq.Ft.

$409,900

MLS#: A4631433

RARELY AVAILABLE FIRST FLOOR END-UNIT in the 12-acre waterfront resort-style gated community of Hidden Bay - move-in ready and fully furnished for an easy Florida lifestyle. This open-concept 2-bedroom, 2-bath home with a flex space offers newer luxury vinyl flooring, a bright and spacious kitchen and a large pantry, and a charming breakfast nook framed by a bay window. The primary suite offers beautiful water views and private access to the enclosed lanai - perfect for morning coffee or unwinding at the end of the day. Inside, you’ll find dual vanities, a soaking tub, walk-in shower, and a private water closet for a true spa-like retreat. The guest suite, thoughtfully positioned on the opposite side of the home, provides comfort and privacy with its own en-suite bath and walk-in closet. Hidden Bay offers resort-style amenities: a newly updated clubhouse, tiki bar, fitness center, heated pool and spa, nature trails, tennis, pickleball and a scenic boardwalk for sunset views. The community is in the process of rebuilding the fishing pier as well, so fishing the intracoastal waterway and a kayak launch is in your future! Quarterly HOA fees include exterior maintenance, water, sewer, trash, and basic cable - making ownership simple and carefree. Just minutes from an assortment of breathtaking beaches, golf courses, Legacy Trail, Siesta Key, and downtown Sarasota’s dining and arts scene, this condo blends relaxation, recreation, and convenience. Move-in ready and waiting for you - hurry and schedule your showing today!
#N6141302

OSPREY

291 HIDDEN BAY DRIVE 101

2 Beds

2 Baths

1,718 Sq.Ft.

$400,000

MLS#: N6141302

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). 11,433 sq ft per survey;117 feet on US 41, 117 feet on Columbia, 102 feet on Shumard, and 96 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

*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.

$374,900

MLS#: A4648348

Price reduced
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!
#N6140508

OSPREY

1801 HIGHLAND ROAD

2 Beds

2 Baths

2,125 Sq.Ft.

$340,000

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!
#A4658738

OSPREY

116 NAVIGATION CIRCLE 106

3 Beds

2 Baths

1,511 Sq.Ft.

$325,000

MLS#: A4658738

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