Sarasota's Premier Homes
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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

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

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$3M - $5M

Over $5M

44 Properties Found. Page 1 of 3.

This newly renovated home in Southbay Yacht and Racquet Club provides resort-style living with an array of amenities including a community heated pool, clubhouse, fitness center, pickleball, and tennis courts. The home is walkable to Pineview School and just minutes from Nokomis Beach. The kitchen is equipped with new appliances, natural stone countertops, and ample storage. The family room offers cathedral ceilings with a large stone fireplace. The rental comprises three bedrooms, including a primary suite complete with an ensuite bathroom and walk-in closet. The additional bedrooms offer versatility for growing families or the option to create a home office or study area. Outside, you'll discover a screened-in private lanai, perfect for enjoying morning coffee. There is an additional patio on the front of the home with views of the intercoastal and the perfect spot to take in the evening sunset. The neighborhood is golf cart friendly with shopping, restaurants, tiki bars, and the beach all accessible by golf cart. Don't miss the opportunity to make this charming community your new home! ***Home is currently rented through October 31st. Showings will be available in November. The minimum lease term is 3 months, but a six-month rental is preferred. Pets are considered on a case-by-case basis. The rental rate published is for an annual rental. Please inquire for a seasonal rental. Must lease for at least 3 months and a 6 month lease is preferred.
#A4666588

OSPREY

456 YACHT HARBOR DRIVE

3 Beds

2 Baths

2,867 Sq.Ft.

$4,800

MLS#: A4666588

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.
#A4663760

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!
#A4623594

OSPREY

456 WASHINGTON AVENUE

None Beds

None Baths

0.13 acres

$239,999

MLS#: A4623594

New on site today
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

1,483 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.
#A4658930

OSPREY

238 PALM AIR DRIVE

2 Beds

2 Baths

1,152 Sq.Ft.

$199,000

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

1,029 Sq.Ft.

$189,900

MLS#: N6140863

Come home to this tastefully-furnished, well-maintained spacious home in a top-of-the-line, perfectly located Co-Op park. LOTS OF UPGRADES: NEW windows 2022, NEW A/C and HVAC 2023, NEW moisture barrier underneath 2022. NEW hurricaine window covers 2023, NEW Solar tube in kitchen 2022, NEW ceiling fan in dining area 2022. Relax in the 1,376 square feet of centrally-cooled comfort. Two large bedrooms + a Florida room that will hold a couple beds + Price includes all furnishings. This roomy home has tons of storage space, a home office area, on and on. GREAT PARK---> Low HOA fees. The Arbors is run by a board of directors elected by the homeowners like you. Boat-Kayak- RV storage area. Heated pool. Exercise area. Picnic Pavilion PLUS Tons and tons of communjity activities. AND IT'S GOT A GREAT LOCATION: You will have a short drive to WalMart, Publix, drug store, restaurants, places of worship, post office, and only 10 minutes to NOKOMIS BEACH. 20 minutes to Sarasota and Venice. Please check-out the pictures to see what's in store for you. Sarasota Memorial Hospital's new facility is only 14 minutes away. You will enjoy many social activities with your new fun-loving neighbors. They have a Christmas Open House party, Halloween party, annual Flea Market, Aqua exercise, morning coffee. And many more social events. **** ALL THIS FOR A LOW PRICE OF A WONDERFUL HOME ****
#A4614751

OSPREY

191 PALM AIR DRIVE

2 Beds

2 Baths

2,296 Sq.Ft.

$185,000

MLS#: A4614751

SELLER OFFERING 1 YEAR HOME WARRANTY! Seller did $20,000 of upgrades. Welcome to 310 Pine Run Dr a charming and thoughtfully designed 1-bedroom, 1-bath condominium with an additional open loft space, nestled in the serene, amenity-rich Pine Run community. This unit blends comfort and functionality with a bright, open layout, perfect for seasonal or year-round living. Have peace of mind with 2022 KITCHEN APPLIANCES, ROOF REPLACED IN 2021, BATHROOM REMODELED IN 2023. Additional conveniences include a COVERED CARPORT and an outdoor storage closet for your gear or beach accessories. Located on over 20 acres of mature Florida landscaping, Pine Run offers a true RESORT STYLE experience with two heated swimming pools, a clubhouse with fitness center, tennis and pickleball courts, kayak storage, and walking paths. Best of all, it’s MINUTES AWAY from Downtown Venice, Casey Key Marina, Blackburn Point Marina, boat launches, waterfront dining, shopping, and the Legacy Trail for biking and walking. Whether you're looking for a peaceful retreat, a smart investment property, or a low-maintenance home close to everything Sarasota County has to offer.
#A4663939

OSPREY

310 PINE RUN DRIVE

1 Beds

1 Baths

886 Sq.Ft.

$177,000

MLS#: A4663939

YOUR PERFECT FLORIDA RETREAT AWAITS.... Imagine spending your winter days in a swimming pool or in the warm waters and beautiful sands of Florida Gulf Coast beaches. This pristine 2 Bed, 2 Bath home located in the Arbors Mobile Park has been meticulously maintained and has many upgrades and extras. Open plan kitchen has dining area and built-in china cabinet. The master bedroom is ensuite and boosts a king sized bed and 3 closets. The living room opens to a large, enclosed florida room with lots of additional dining space for entertaining or just enjoying your morning coffee, evening cocktails, and includes a portable AC unit. Home is being sold turnkey furnished; bright and beautiful, with new furnishings in 2021 and 2022 including upgrades to HVAC with air purifier UV light, new electric panel, vapor barrier and subflooring, interior flooring, roof coated and sealed. Just pack your clothes and move right in! The large attached storage has lots of cabinetry, washer, dryer, work bench, manual and power tools, gas grill, compressor, 2 bicycles, golf clubs, plus EVERYTHING for you beach escape including chairs, umbrella, coolers, towels, floats and more, more, more! There is also a brand new unopened ENERGY STORM 4100 Lifan Power USA Generator. EZGO TXTE Golf Cart with GCO Custom Package, LED lights and newer batteries available at Seller's discretion. The Arbors Park is a 55+ Co-op community with low HOA fee that includes cable, internet, water, trash and grounds maintenance. Amenities include clubhouse, heated community pool, shuffleboard, billiards, exercise equipment, picnic area and area for RV and Boat parking. Located close to shopping, dining, hospital, Nokomis beach and minutes to Blackburn Point Park and Casey Key. So many ways to relax and spend your sun-filled days. Such an outstanding value-you just have to see to believe. Don't miss out on your opportunity to purchase your piece of paradise! Schedule your private showing today. Security devices on property.
#A4657652

OSPREY

170 EDGEWOOD DRIVE

2 Beds

2 Baths

1,645 Sq.Ft.

$164,900

MLS#: A4657652

Highly desirable floor-level T-Top boat rack at Osprey Harbor Village with 12 ft of height! This XL rack accommodates vessels up to 30.5L x 10W x 12H and offers quick access to Midnight Pass and Venice Inlet. Marina amenities include call-ahead splash, fuel, ice, bait and tackle, fish cleaning station, adjacent restaurant, maintenance racks, and wash-down service after each use. Monthly condo fees of $424 cover insurance, marina and building maintenance, staff, and equipment. Indoor storage reduces insurance costs, and racks may be rented, making this a great investment in Sarasota waterfront property. When you own indoor boat storage, you'll have year-round peace of mind with protection from the elements.
#A4664565

OSPREY

570 BLACKBURN POINT ROAD 19

None Beds

None Baths

N/A

$145,000

MLS#: A4664565

Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! This rarely available slip can fit boats up to 9 ft in height and 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 9W x 9 H. 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.
#A4660688

OSPREY

570 BLACKBURN POINT ROAD 13

None Beds

None Baths

N/A

$115,000

MLS#: A4660688

Dry boat slip for sale at Osprey Harbor Village hurricane-protected dry storage with top-tier amenities! This rarely available slip can fit boats up to 9 ft in height and offers hassle-free storage in one of Sarasota County?s most convenient locations. Keep your boat safe from Floridas 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 30.5L x 10W x 9 H. 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 boaters 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.
#A4653194

OSPREY

570 BLACKBURN POINT ROAD 33

None Beds

None Baths

N/A

$105,000

MLS#: A4653194

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
#A4656824

OSPREY

3976 DESTINATION DRIVE A411

None Beds

None Baths

2,314 Sq.Ft.

$96,000

MLS#: A4656824

New on site today
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.
#A4668687

OSPREY

570 BLACKBURN POINT ROAD 35

None Beds

None Baths

N/A

$89,000

MLS#: A4668687

Dry Boat Slip for Sale – Osprey Harbor Village, Sarasota County Secure your spot in one of Sarasota County’s premier boating destinations with this hurricane-protected dry boat slip at Osprey Harbor Village. Designed to offer both protection and convenience, this indoor slip ensures your boat is shielded from Florida’s unpredictable weather — potentially reducing your insurance premiums by eliminating storm prep. Slip Size: Accommodates boats up to 30’-6” L x 10’ W x 7’-6” H (Actual slip size: 31' long x 11' wide x 9'-6" high) Prime Location: Located just before the swing bridge to Casey Key at ICW Marker 33, north of Blackburn Point Bridge, this slip offers quick access to Midnight Pass and the Venice Inlet, making every boating trip easy and enjoyable. Top-Tier Amenities: Osprey Harbor Village is known for its premium services and full-service marina, including: Valet boat service Full-time staff Fuel and pump-out stations Wash racks and maintenance racks Fish cleaning tables Bait and tackle shop Picnic tables and restrooms On-site restaurant, deli, and ship store Whether you're focused on safety, convenience, or luxury, this dry boat slip delivers it all. Protect your investment, skip the hassle of storm prep, and enjoy effortless boating with first-class service at Osprey Harbor Village.
#A4658717

OSPREY

570 BLACKBURN POINT ROAD 6

None Beds

None Baths

N/A

$44,000

MLS#: A4658717

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