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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

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

163 Properties Found. Page 9 of 11.

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 bedroom 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

This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey Key Fish House and Tiki Bar. Shopping and restaurants are all nearby! The location of this condo within the Pine Run community is also good with an abundance of trees and landscaping creating a private setting from your lanai off the livingroom. You will feel like you are living in a tree house! This condo has had extensive work done in the last 6 years including ELECTRIC ON-DEMAND TANKLESS HOT WATER HEATER, NEW CUSTOM KITCHEN WITH DOVE TAIL DRAWER CHERRY CABINETS, FLOORING, PAINT, LIGHT FIXTURES, NEW BATHROOMS AND PLUMBING. Unique frosted glass sliding doors in the dinette area open to washer dryer combo plus a pantry area! Crown molding in the living and dining area give an elegant feel to the rooms, The roof, maintained by the HOA was replaced about 3 years ago. Pine run is an active, vibrant community with small clubhouse with fitness room, pickle ball, tennis and other activities just waiting for you. Come take a look! If you are comparing other condo's, this one has much to like!

OSPREY

232 WOODLAND DRIVE

2 Beds

2 Baths

1,483 Sq.Ft.

$269,900

MLS#: A4671600

New on site 3 days ago

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.

OSPREY

216 GLENWOOD AVENUE

2 Beds

1 Baths

732 Sq.Ft.

$250,000

MLS#: A4673441

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.

OSPREY

106 VILLA DRIVE 106

2 Beds

2 Baths

1,903 Sq.Ft.

$249,900

MLS#: A4669327

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

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.

OSPREY

362 PINE RUN DRIVE

2 Beds

2 Baths

1,470 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.

OSPREY

244 WOODLAND DRIVE 244

2 Beds

2 Baths

1,483 Sq.Ft.

$225,000

MLS#: A4667419

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.

OSPREY

238 PALM AIR DRIVE

2 Beds

2 Baths

1,152 Sq.Ft.

$198,000

MLS#: A4658930

#N6140863

OSPREY

238 WOODLAND DRIVE 238

1 Beds

1 Baths

1,029 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.

OSPREY

218 PALM AIR DRIVE

2 Beds

2 Baths

2,001 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!

OSPREY

216 PALM AIR DRIVE

2 Beds

2 Baths

1,943 Sq.Ft.

$164,000

MLS#: A4672438

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!!!

OSPREY

26 SIESTA CIRCLE W

2 Beds

1 Baths

1,060 Sq.Ft.

$129,500

MLS#: A4673353

Price reduced

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.

OSPREY

348 TROPIC DRIVE

2 Beds

2 Baths

1,452 Sq.Ft.

$119,000

MLS#: A4668240

Price reduced

Newly Built-Out & Fully Furnished Move-In Ready Office Space at Baystreet Village! Located in the vibrant heart of Osprey, this beautifully designed office space at 3976 Destination Drive, Unit A-411, Osprey, FL 34229 is the perfect opportunity for your business to thrive. Baystreet Village is a premier commercial enclave offering a mix of retail and office spaces, just minutes away from The Oaks, Casey Key, and Pineview School, providing easy access to a thriving community. This move-in ready office features modern finishes, full furnishings, and a layout designed for efficiency, allowing you to set up and start working immediately. Whether you're expanding your business or starting fresh, this space offers the perfect combination of convenience and professionalism. Key Highlights:Newly built-out, fully furnished office space,Prime location in Baystreet Village, Osprey’s most sought-after commercial enclave. Close proximity to The Oaks Golf & Country Club, Casey Key Beach, and Pineview School Easy access to major roads, offering quick connections to Sarasota and surrounding areas Don’t miss this rare opportunity to position your business in one of Osprey’s best commercial locations. Schedule a tour today!
Land, Site, and Tax Information

OSPREY

3976 DESTINATION DRIVE A411

None Beds

None Baths

2,314 Sq.Ft.

$90,000

MLS#: A4656824

Hurricane-protected dry storage with top-tier amenities! This slip offers hassle-free storage in one of Sarasota County's most convenient locations. Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to 32.5L x 9.7W x 8H. With valet boat service, full-time staff, wash, fuel, and pump-out stations, fish cleaning tables, a bait and tackle shop, maintenance racks, picnic tables, restrooms, an on-site restaurant, deli, and ship store, it's a boater's dream. Call ahead for splash, fueling, and even have your deli order waiting when you arrive. Enjoy quick access to Midnight Pass and the Venice Inlet, along with the peace of mind that comes from hurricane-safe indoor storage that could even reduce your insurance costs. Skip the storm prep, protect your investment, and enjoy effortless boating with first-class service at Osprey Harbor Village.

OSPREY

570 BLACKBURN POINT ROAD 35

None Beds

None Baths

N/A

$89,000

MLS#: A4668687

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