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Osprey

One of the most popular communities provided by The Graf Group of Coldwell Banker

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 The Graf Group of Coldwell Banker
144
# of Listings
3
Avg # of Bedrooms
$515
Avg. $ / Sq.Ft.
$1,219,332
Med. List Price

Browse Osprey Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

21 Properties Found. Page 2 of 2.

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. There is a community pool where you can enjoy a refreshing swim or relax poolside. 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

1,165 Sq.Ft.

$299,900

MLS#: N6140508

Luxury Corner Residence in Osprey | Top-Rated Pine View School District. Welcome to an exceptional opportunity in the heart of Osprey, one of Sarasota County’s most desirable and rapidly growing locations. This beautifully maintained corner-unit residence in Bay Street Village offers an elevated lifestyle just moments from world-class amenities. This FULLY FURNISHED 2-bedroom, 2-bathroom home with a private garage showcases light-filled, open-concept interiors, enhanced by hurricane-impact windows and elegant finishes throughout. The spacious layout is designed for both comfort and entertaining, featuring an oversized kitchen island, stainless steel appliances, and generous storage. Step outside to your private screened lanai, perfect for relaxing mornings or unwinding in the evening in a peaceful, tropical setting. Highlights include: Highly sought-after corner unit for added privacy and natural light Private garage + additional parking Resort-style community with pool Pet-friendly neighborhood Meticulously maintained, move-in ready condition Ideally located just minutes from Siesta Key Beach, Nokomis Beach, dining, shopping, and the Legacy Trail, this property also offers proximity to the nationally recognized Pine View School, consistently ranked among the top public schools in Florida. Whether you are looking for a primary residence, seasonal retreat, or investment property, this home delivers both lifestyle and long-term value. Luxury, location, and top-tier education—this is Osprey living at its finest.
#A4692249

OSPREY

184 EXPLORER DRIVE

2 Beds

2 Baths

1,244 Sq.Ft.

$294,900

MLS#: A4692249

One or more photo(s) has been virtually staged. Live where everyday life feels simple, connected, and close to everything you love. Located in the gated community of Bay Street Village in Osprey, this beautifully maintained second-floor condo offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar Scherer State Park, and an abundance of shopping and dining options, everything you need is right at your fingertips. This 2-bedroom, 2-bathroom condo welcomes you with a private entry and interior stairway leading to a bright and open main living space. Positioned on the second floor, the home enjoys added privacy along with elevated views and an abundance of natural light. The layout lives effortlessly, with high ceilings and neutral finishes creating an inviting and airy feel throughout. An attached garage with direct interior access adds everyday ease and practicality. The kitchen is both functional and stylish, featuring granite countertops, stainless steel appliances, a large island with seating, and a walk-in pantry. It opens seamlessly to the dining and living areas, making it easy to host, relax, or simply enjoy day-to-day living without feeling closed off. The spacious primary suite offers a comfortable retreat with a large walk-in closet and an en-suite bathroom complete with dual sinks and a walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Enjoy your morning coffee or unwind in the evening on the screened lanai, where you can take in the Florida breeze and peaceful surroundings from your elevated position. Whether you're heading out to the beach, meeting friends for dinner, or enjoying the nearby parks and trails, this location makes it all feel effortless. Bay Street Village enhances the lifestyle even further with resort-style amenities including a community pool, fitness center, scenic ponds, and beautifully landscaped grounds, all within a gated and well-maintained setting. **SELLER FINANCING AVAILABLE** **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
#A4689541

OSPREY

4271 EXPEDITION WAY 103

2 Beds

2 Baths

1,135 Sq.Ft.

$290,000

MLS#: A4689541

This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.
#A4690371

OSPREY

51 MAC EWEN DRIVE 14

1 Beds

1 Baths

595 Sq.Ft.

$285,000

MLS#: A4690371

Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is perfect for hosting out of town visitors, or for you to use as a weekend get-a-way. And, when you are not using it, the flexible rental policy allows you to easily lease the unit. Offered turnkey furnished and with the convenience of the Windsor Lodge pool and clubhouse just steps away, there is no better way to experience The Oaks with little effort and a lot of comfortable, maintenance-free enjoyment.
#A4690540

OSPREY

51 MACEWEN DRIVE 12

1 Beds

1 Baths

623 Sq.Ft.

$275,000

MLS#: A4690540

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

$269,999

MLS#: A4623594

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