One of the most popular communities provided by {{page_data.agentName}}

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

144

# of Listings

3

Avg # of Bedrooms

$407

Avg. $ / Sq.Ft.

$971,873

Med. List Price

Browse Osprey Real Estate Listings

$250,000 - $500,000

22 Properties Found. Page 2 of 2.

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.

$319,000

MLS#: A4658738

Welcome to Bay Street Village, Osprey - Perfectly nestled between the vibrant cities of Sarasota and Venice - only minutes to the pristine shoreline of Nokomis Beach. This desirable gated community features a resort style heated pool, clubhouse and a fitness center designed to enhance your Florida life style. Enjoy local dining, shopping, and many arts and cultural attractions.

This second floor meticulously maintained 2-bedroom/2-bathroom condo has an open floor plan and has an abundance of natural light. The kitchen is a chef's delight with rich dark wood cabinetry, granite countertops, stainless steel appliances, a walk-in pantry and a ample breakfast bar. The spacious dining area is adjacent and is perfect for casual dining or entertaining. The living room is comfortable for relaxing. Step onto a screened lanai; perfect for a peaceful morning or a wind down at the end of the day. Primary suite includes a walk-in, linen closet and an ensuite bathroom. Bathroom is complete with dual sinks, makeup vanity and a large shower. The second bedroom has a sizable closet and full bathroom nearby. The second bathroom comes complete with a shower/tub combo. The laundry room is conveniently located in the hallway near bedrooms. Included is an attached one car garage with an additional storage room. Perfect for full time residence, seasonal enjoyment or as an investment property.

OSPREY

4267 EXPEDITION WAY

2 Beds

2 Baths

1,219 Sq.Ft.

$310,000

MLS#: A4656830

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

AMENITIES? YES! Reduced just in time for Snow Bird Season! You can have Floridas #1 Amenity a Boat Slip available to you 365 Days a year. Access to the Intracoastal and the Blue waters of the Gulf of Mexico in minutes. No association pool but you can put in your own! Nokomis Beach and the famous Drum Circle is 5 minutes away with shops and restaurants close by in downtown Venice. Take a look inside the Villa is completely updated. All new LVPF throughout, upgraded stainless appliances, granite counters and all new cabinets. Property Trends Open floor plan. Split bedroom floor plan with well appointed ensuites. Ready to buy now?

OSPREY

208 VILLA DRIVE 208

2 Beds

2 Baths

1,389 Sq.Ft.

$275,000

MLS#: TB8367998

Welcome to this beautifully appointed, well-cared for and fully furnished 2-bedroom, 2-bath condo located in the sought-after Pine Run community. It is completely turnkey; all you need to bring are your clothes! This second-floor unit has been tastefully updated and comes equipped with everything you need to move right in, including all furniture, beds, bedding, all kitchenware, appliances, and even recreational items like beach chairs, coolers, and two bicycles. The 9-ft high ceiling gives you an open, airy feel. The unit has been updated throughout and re-plumbed for peace of mind. The two separate en-suite bedrooms are spacious and have their own patio decks and patio furniture for added privacy. The kitchen boasts solid wood cabinets, granite countertops, a cozy dinette area and it opens to a formal dining room, along with a comfortable living room that opens to a covered screened porch. Elegant upgrades include engineered hardwood scraped hickory flooring, designer light fixtures and fans, profiled baseboards and custom blinds. There’s ample storage with a deeded covered carport, two storage lockers and an easily accessible attic. Pine Run spans 20 acres of lush, tropical landscaping and offers an array of amenities to enhance your lifestyle. There are two heated pools, with one conveniently located just steps from the unit, pickle ball, tennis courts, walking trails, kayak rack storage for easy access to water adventures, and a main clubhouse with a fitness center for social gatherings. Situated just a mile from the iconic Casey Key Road and only two miles from Nokomis Beach, this condo offers the perfect blend of tranquility and convenience. Sarasota Airport is just 17 miles away, making travel a breeze. Across the street, you’ll find everything you need for daily living, including a Publix grocery store, hardware, salon, specialty retailers, fitness center, bike rental store & medical services. For dinner and entertainment take a leisurely stroll to the new Deep Lagoon restaurant or enjoy live music at the popular Casey Key Fish House and Tiki Bar. Six additional restaurants are within walking distance, offering a variety of dining options. The Legacy Bike Trail, area state parks and public beaches are all nearby. Whether you’re looking for a vacation retreat or a full-time residence, this condo offers everything you need to enjoy Florida living at its best. Do not miss out on this incredible opportunity to own a piece of paradise in one of the most desirable locations on the Gulf coast. Pine Run is nestled between Sarasota and Downtown Venice and is 7 miles away from the famous Siesta Key Beach, voted the #1 beach in the U.S.

OSPREY

207 WOODLAND DRIVE 207

2 Beds

2 Baths

1,483 Sq.Ft.

$269,999

MLS#: A4610314

#T3541882

OSPREY

758 PINE RUN DRIVE 758

2 Beds

2 Baths

1,184 Sq.Ft.

$256,600

MLS#: T3541882

1 2

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