Sarasota's Premier Homes
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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
170
# of Listings
3
Avg # of Bedrooms
$463
Avg. $ / Sq.Ft.
$1,093,037
Med. List Price

Browse Osprey Real Estate Listings

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$3M - $5M

Over $5M

48 Properties Found. Page 1 of 4.

Nestled in the quietly coveted, underrated gem of Osprey, FL, this charming property offers the perfect blend of coastal living, privacy, and timeless Florida character. Situated on a maintained, fenced lot, this home is framed by mature greenery and ample outdoor space—ideal for gardening, play, pets, or serene evenings under the palms. The quaint, inviting home exudes warmth from the moment you arrive, with a cozy interior layout that captures natural light and coastal breezes. It is equally suited as a full-time residence, seasonal retreat, or investment opportunity. Located in one of Sarasota County’s best-kept secrets, you’re just minutes from top-rated schools, parks, marinas, and the Gulf’s pristine beaches—all while enjoying the peace and charm that make Osprey so special. If you’re seeking character, privacy, and an unbeatable location, this property is a rare find that truly stands out.
#A4673441

OSPREY

216 GLENWOOD AVENUE

2 Beds

1 Baths

732 Sq.Ft.

$250,000

MLS#: A4673441

Here’s a polished real estate listing you can use: --- **Stunning Fully Remodeled 1-Bed / 2-Bath Ground-Floor Condo with Designer Finishes + $15,000 Custom Golf Cart Included** Step into luxury and comfort in this beautifully remodeled ground-floor condo, professionally designed from top to bottom. Every detail has been thoughtfully crafted to create a modern, open-concept living experience surrounded by natural beauty. **Property Highlights:** * **1 bedroom, 2 bathrooms** — spacious layout perfect for full-time living or a serene seasonal retreat * **Professional designer remodel** — high-end finishes, updated fixtures, new appliances, and a cohesive modern aesthetic throughout * **Nature views from all sliding glass doors** — enjoy peaceful, scenic greenery no matter where you are in the home * **Open floor plan** — seamless flow between living, dining, and kitchen areas * **Large enclosed lanai** — accessible from both the living room and bedroom, perfect for relaxing, entertaining, or enjoying morning coffee * **Expansive front courtyard** — a welcoming outdoor space as you enter the home * **Exceptional storage** — 2 interior storage closets plus 2 additional exterior-access storage areas * **Covered carport** — convenient, protected parking right at your doorstep * **BONUS: Custom $15,000 golf cart included** — a fantastic added value for lifestyle, leisure, or getting around the community This ground-floor showpiece blends luxury, practicality, and unmatched natural surroundings. Move-in ready and designed to impress, it’s the perfect opportunity for buyers seeking a unique, beautifully remodeled home with exceptional extras.
#N6141829

OSPREY

139 WOODLAND PLACE 139

1 Beds

1 Baths

865 Sq.Ft.

$244,909

MLS#: N6141829

One or more photo(s) has been virtually staged. Welcome to 362 Pine Run Drive, a move-in ready, modern retreat nestled in the heart of Osprey, FL. This stunning 2-bedroom, 2-bathroom home offers 1,224 square feet of thoughtfully designed living space, set on an expansive 20-acre property. Revel in the tranquility of garden views and the glow of sunsets in the distance off the rear facing deck. Looking for a little more privacy? Access a large, private outdoor area from the kitchen or off of the main hallway. Soaring ceilings and abundant natural light fill the living areas and each room opens to inviting outdoor spaces, perfect for relaxation or entertaining. The home boasts a completely updated kitchen, featuring sleek finishes and high-end appliances, along with renovated bathrooms, new flooring throughout, new ceiling fans and lighting, ensuring a contemporary and stylish living experience. As part of a vibrant community, enjoy access to two sparkling pools, tennis and pickleball courts, a state-of-the-art fitness center, and a welcoming clubhouse. Outdoor enthusiasts will appreciate the fire pit and grill area, perfect for gatherings. Conveniently located near Publix, CVS, Ace Hardware, and a variety of dining options, this property offers the perfect blend of serene living and modern convenience. Experience the best of Osprey living at 362 Pine Run Drive.
#A4672574

OSPREY

362 PINE RUN DRIVE

2 Beds

2 Baths

1,224 Sq.Ft.

$235,000

MLS#: A4672574

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.
#A4667419

OSPREY

244 WOODLAND DRIVE 244

2 Beds

2 Baths

1,325 Sq.Ft.

$225,000

MLS#: A4667419

Price reduced
Located West of the Trail in Sorrento Shores, Osprey, this spacious 2BR/2BA villa with a den and oversized 1-car garage offers 1,578 sq. ft. of comfortable living space. A boating community with private dock access and a heated pool just steps away, it’s perfect for boaters, kayakers, or anyone seeking the coastal lifestyle. Features include hurricane-rated windows and doors, updated kitchen and baths with granite countertops, and a private walled courtyard ideal for entertaining. Home is currently being remodeled—ideal for investors or buyers ready to finish with their own touch. Sight-unseen (“blind”) offers will not be considered. No owner financing available.
#A4669327

OSPREY

106 VILLA DRIVE 106

2 Beds

2 Baths

1,578 Sq.Ft.

$199,000

MLS#: A4669327

AN ARBORS BEAUTY in one of Florida’s most-sought-after 55+ parks. You won’t believe how BIG and BEAUTIFUL this home is !! Over 1,152 square feet of centrally-cooled comfort. Large living room. New laminate flooring. A chef’s kitchen. Comfy throughout. 2 LANAIS: (1) Front lanai with new windows and new tile flooring; (2) Side lanai is carpeted, screened and ready for relaxing. Both lanais add more living space. Private Paved Patio 30x14 in the back yard . You’ll get more rest and relaxation. New attached work shed with lots of extra storage space. Attached laundry with washer and dryer plus more storage space. DOG-FRIENDLY zone up to 35 pounds. HERE ARE THE DETAILS: Open floor plan with kitchen, dining area and living room spaced perfectly. All kitchen appliances are FREE. New hurricane windows throughout. Master bedroom has 2 walk-in closets and attached sparkling bathroom with bathtub. The guest bedroom has a Murphy Bed and 1 walk-in closet. Plus the hallway has a full bath. Beautifully landscaped with night lighting. THE ARBORS provides a pool, pickleball court, clubhouse with many social events for you and your fun-loving, sun-loving neighbors: parties, annual flee market, bingo, poker nights, and more and more and more . . . . You will have A SHORT DRIVE TO Walmart, Publix, drug store, restaurants, places of worship, post office and ONLY 10 MINUTES TO NOKOMIS BEACH !! The HOA fee is a low $215/month.
#A4658930

OSPREY

238 PALM AIR DRIVE

2 Beds

2 Baths

1,152 Sq.Ft.

$198,000

MLS#: A4658930

Live like you're on vacation every day in this beautiful one bedroom, one and a half bath, FIRST FLOOR condo in the popular community of Pine Run! Step inside and you'll find a welcoming, well-designed, floor plan that is beautifully decorated throughout. The primary bedroom has a beautiful UPDATED ensuite bathroom with a new hurricane window, dual closets and a private sliding patio door to the back lanai that lets the natural light in. The half bath is also UPDATED and has granite countertops. The UPDATED kitchen has plenty of cabinets for storage, beautiful granite countertops, a pass through counter to the dining area and a new hurricane impact sliding patio door letting in more natural light and opening to a cozy private patio. The screened-in lanai runs almost the entire length of the back of the condo and is a perfect space to enjoy the warm tropical breezes and views of the lush tropical landscaping. Lovely tile flooring in every room. Two pets are welcome here! A/C and water heater new in 2021. Plus you have your own brand new in 2025 stackable washer and dryer inside this unit. This condo comes with a covered one car carport and TWO outdoor storage closets; a perfect place to store your beach chairs and bicycle! Pine Run is a resort-style community in a fabulous location in Osprey with beautiful tropical landscaping and all kinds of amenities to enjoy from the two heated community pools, pickleball and tennis courts, club house with fitness room and outdoor kayak storage racks! During the season there are plenty of fun events to fill up your calendar. Close to Nokomis beach, in a great location between Sarasota and Venice where you will find delicious waterfront restaurants, boutique shoppes, festivals golfing, fishing, boating and more. This wonderful condo is ready right NOW for you to move in, relax and start having fun!
#N6140863

OSPREY

238 WOODLAND DRIVE 238

1 Beds

1 Baths

865 Sq.Ft.

$189,900

MLS#: N6140863

You’ll be impressed with this delightful double wide from the moment you enter featuring 2 spacious bedrooms and 2 updated bathrooms with a total of 1120 Sq Feet built in 1979 with large shed and enclosed lanai. Being sold Furnished and Turnkey. The kitchen was totally remodeled in 2020 an island was added with new appliances in and it flows into the dining area and living room creating a large living space. The current owners added an inside laundry roomie 2023 to do laundry inside the home with washer and dryer . The flooring has been substantially replaced with new plywood. New HAVC with HEAT PUMP in 2017. The electrical systems were totally updated in 2019 including a new panel. Enjoy your large west facing lanai with tiled floor and sliders. The 215 monthly HOA fee includes all the landscaping, TV and internet and all the amazing clubhouse amenities such as the HEATED pool.The home is in the dog section so you may have 1 dog up to 30 lbs or 1 cat, birds and fish. This is a very active 55+ community, with Clubhouse, heated pool, shuffleboard, kayak, boat, RV, truck storage area. Located close to legacy trail and about one mile from fishing/boat ramp on inter coastal. Seven Minutes to Nokomis Beach and 20 minutes to Siesta Key.
#N6141261

OSPREY

218 PALM AIR DRIVE

2 Beds

2 Baths

1,120 Sq.Ft.

$189,000

MLS#: N6141261

This home is located in the sought-after 55+ community of The Arbors. It offers a blend of comfort, updates, and a prime location between Sarasota and Venice. Featuring 2 bedrooms, 2 bathrooms, and a newly built carport, this home is designed for easy and comfortable living. The bright and airy living room welcomes you with abundant natural light, while the primary bedroom includes a spacious walk-in closet. French doors lead to the carport, and sliding doors open onto a lovely screened lanai, perfect for relaxing or entertaining. The home boasts fresh exterior paint, giving it a fresh and well-maintained look. A huge storage room sits under the carport, providing ample space for belongings and housing the laundry facilities for added convenience. The Arbors community boasts a range of amenities including a clubhouse, heated swimming pool, recreational area, boat and RV storage, a picnic pavilion, and a shuffleboard court. Residents can engage in numerous social activities or simply relish their peaceful retreat. This charming home is ideally situated just over a mile from the picturesque Casey Key, a short drive from Nokomis Beach, Venice Beach, and the vibrant Historic Downtown Venice. Surrounded by lush parks and natural beauty, the location offers a perfect blend of convenience and tranquility. For outdoor enthusiasts, the Legacy Trail is only about two miles away by bike, providing an exceptional opportunity for scenic rides and leisurely strolls. The property is also close to Sarasota Memorial Hospital, making it a practical choice for those seeking nearby healthcare options. This is a rare opportunity to own a well-maintained home in a friendly and vibrant community. Schedule your private tour today!
#A4672438

OSPREY

216 PALM AIR DRIVE

2 Beds

2 Baths

1,055 Sq.Ft.

$164,000

MLS#: A4672438

Welcome to this charming, TURNKEY FURNISHED home in the desirable 55+ cooperative community of The Arbors, where you own your lot and enjoy the benefits of no monthly lot rent! Friendly neighbors and a peaceful setting make this a truly welcoming place to live! Enjoy affordable Florida living in this quaint community, where your neighbors quickly become your friends! Inside, you’ll find an open floor plan with vaulted ceilings, along with two spacious bedrooms, both of them with walk-in closets. You’ll appreciate the convenience of an indoor laundry area located just off the bedrooms, as well as the bright and comfortable front Florida Room—perfect for morning coffee or evening relaxation. A large outdoor shed offers abundant storage, and the backyard patio is ideal for unwinding and enjoying the gorgeous Florida sunsets. Skylights in the dining room bathe the space in natural light, creating a warm and inviting atmosphere. This desirable outer lot offers a pleasant backyard space with desired shade from a lovely tree and is pet-friendly for your furry family. Monthly dues are just $215 and include an impressive list of amenities: access to the clubhouse, heated community pool, lawn service, water, garbage pickup, cable TV, and internet. There have been numerous updates throughout the years, including: 2024: New laminate flooring in primary bedroom & bath - 2021: New kitchen flooring - 2020: New carpet in 2nd bedroom, new moisture barrier - 2019: Electrical updates - 2016: New roof with transferable 20-year warranty - 2015: New laminate flooring in living room - 2008: Complete home repipe. There’s even a storage area for your toys for a nominal charge: safely store your boat, RV, or kayaks on site! The location is unbeatable—ride your bike or golf cart to Casey Key, the Legacy Trail, Walmart, or the Post Office. You’re also just a short drive from historic downtown Venice and the lively attractions of downtown Sarasota. The community also offers an active clubhouse, shuffleboard, exercise area, and regular social events. A wonderful, affordable place to call home!
#N6141713

OSPREY

300 TROPIC DRIVE

2 Beds

2 Baths

1,031 Sq.Ft.

$159,900

MLS#: N6141713

Just Move In ... Affordable Fully furnished 2-bedroom home with central air is located in an active 55 and over community Located in the heart of Osprey with nearby shopping and dining and easy access to nearby Siesta Key Beach, Casey Key and Nokomis Beach along with The Legacy Bike trail and Oscer Scherer State Park. The Arbors Mobile Home Park with Low Hoa Fees offers a heated community pool with lots of sunbathing space, shuffleboard, billiards, and exercise equipment. Bring your RV, boat and kayaks the development has on site storage. Fully Furnished in great condition .Why pay more for less this is a great place to spend the season or a lifetime. Welcome Home!!!
#A4673353

OSPREY

26 SIESTA CIRCLE W

2 Beds

1 Baths

600 Sq.Ft.

$129,500

MLS#: A4673353

The Arbors is the BEST of the Florida sun belt communities. This lovingly maintained manufactured home is perfect for a "Snowbird" or a "Year-Rounder." It is in a PET FRIENDLY zone. YOU and your fellow homeowners will own the company that owns the park . it's a Co-Op park for over-55 owner residents. Therefore, everybody takes pride in keeping it wonderfully maintained and reasonably priced with low HOA dues. For showings please call the listing agent for the lock box combination. Better take a look and make an offer before the bidding war starts.
#A4668240

OSPREY

348 TROPIC DRIVE

2 Beds

2 Baths

864 Sq.Ft.

$119,000

MLS#: A4668240

This slip will house a boat with the maximum dimensions of 27.5'L x 11'W x 11.5'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is also an onsite boat detailing company, independent mechanic, as well as boat transporter. The marina is centrally located between Sarasota and Venice on Little Sarasota Bay. It is just minutes from Midnight Pass...the highly anticipated new opening project being reviewed by Sarasota County. Open seven days a week
#A4672823

OSPREY

570 BLACKBURN POINT ROAD 43

None Beds

None Baths

N/A

$115,000

MLS#: A4672823

The slip can hold a boat with the maximum dimensions of 32.5L x 9'W x 9'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is also an onsite boat detailing company, independent mechanic, as well as boat transporter. The marina is centrally located between Sarasota and Venice on Little Sarasota Bay. It is just minutes from Midnight Pass...the highly anticipated new opening project being reviewed by Sarasota County. Open seven days a week
#A4674344

OSPREY

570 BLACKBURN POINT ROAD 13

None Beds

None Baths

N/A

$109,000

MLS#: A4674344

The slip can hold a boat with the maximum dimensions of 30.5'L x 10'W x 9'H.This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is also an onsite boat detailing company, independent mechanic, as well as boat transporter. The marina is centrally located between Sarasota and Venice on Little Sarasota Bay. It is just minutes from Midnight Pass...the highly anticipated new opening project being reviewed by Sarasota County. Open seven days a week for your convenience.
#A4674347

OSPREY

570 BLACKBURN POINT ROAD 33

None Beds

None Baths

N/A

$103,000

MLS#: A4674347

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