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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
160
# of Listings
3
Avg # of Bedrooms
$532
Avg. $ / Sq.Ft.
$1,266,683
Med. List Price

Browse Osprey Real Estate Listings

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Over $5M

160 Properties Found. Page 10 of 11.

Beautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions Welcome to this immaculate 3-bedroom, 2-bath home, newly built in 2021 and perfectly located just minutes from top-rated beaches, shopping, dining, and entertainment. This move-in-ready home offers a clean, modern design with a spacious open floor plan that’s ideal for both relaxing and entertaining. Enjoy cooking in the stylish open kitchen, complete with granite countertops and ample cabinet space. Luxury vinyl flooring runs throughout the home, adding durability and a sleek, contemporary feel. With no HOA, CDD, or deed restrictions, this property provides true freedom and flexibility—bring your boat, RV, or other recreational vehicles with ease. The generous lot offers plenty of room for parking and outdoor enjoyment. Don’t miss this rare opportunity to own a centrally located, low-maintenance home in a highly desirable area!
#N6138982

OSPREY

352 GLENWOOD AVE

3 Beds

2 Baths

1,300 Sq.Ft.

$429,500

MLS#: N6138982

Price reduced
Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the post office and two Tiki bars. You can launch your kayak from the private waterfront park on a protected bay with dockage for boats up to 22 feet. There is a waiting list for the dockage. Bay Acres is a non-deed-restricted neighborhood. You can park your RV or commercial vehicles on your property. Major updates include new roof, 3 years old, exterior paint 3 years, New HVAC this year, a Water treatment system recently installed and a rescreened lanai. Some interior updates have been done, but most need personal touches. This house has a new neighbor owned fence at the back of the lot and no fence at either side. The lot is large enough for a pool.
#A4676179

OSPREY

524 SARABAY ROAD

3 Beds

2 Baths

1,760 Sq.Ft.

$419,000

MLS#: A4676179

In the lush and serene grounds of this private and peaceful community is a best-kept secret with a name that says it all. Within Hidden Bay, this condominium gem resides in a spot on the community lake with a stunning view and soothing sound of waterfalls from your own enclosed lanai. Fully furnished with mostly all new furniture in the owners’ suite, including a new king-size mattress, living room, guest bedroom and the office/den, this turnkey treasure is move-in ready! Loaded with many new upgrades which include new kitchen appliances such as refrigerator, microwave and dishwasher (2025), new laminate flooring in both bedrooms (2025), a new water heater (2024), new faucets and toilets (2025), new air conditioner (2020), all new screens (2025), all new slider wheels (2025) and interior painted (2025). The home offers two bedrooms, two baths and an office/den, a one- car detached garage and an etched glass front door. The flooring consists of new laminate in both bedrooms, laminate in the office/den and ceramic tile throughout the rest of the home. Beautiful lake views can be seen from the living room, kitchen and owner’s suite. The owner’s suite bath has dual vanities, a soaking tub and a walk-in shower while the guest bath has a soaking tub. This unique waterfront community exudes an awesome Florida lifestyle that boasts many amenities with a newly renovated heated pool and spa, a clubhouse with a full kitchen, a tiki bar, game rooms, a library, a fitness center, a large sundeck, grilling stations, two lit pickleball courts, tennis, a kayak launch, a dog park, a car wash area and a 500-yard elevated boardwalk that winds through mangroves and palms offering scenic sunset watching. And coming soon is a 150-foot fishing pier all for your enjoyment. HOA fees include exterior maintenance, water, sewer, trash and basic cable. Centrally located between Sarasota and Venice, Hidden Bay is on Little Sarasota Bay in Osprey, an ideal location just minutes from the award-winning beaches of Siesta Key and Venice Beach, Sarasota with its many cultural venues, golfing and a variety of casual and fine dining restaurants. Make this special home your own piece of paradise!
#A4681398

OSPREY

291 HIDDEN BAY DRIVE 102

2 Beds

2 Baths

1,479 Sq.Ft.

$399,000

MLS#: A4681398

**1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious Owner’s Suite boasts multiple walk-in closets, dual vanities, soaking tub and custom tiled shower. Tile Flooring Throughout. Enjoy the serene and natural surroundings from your sprawling and screened lanai which is accessible from multiple rooms via sliding doors. This Secure and Gated Community offers the ultimate Florida Lifestyle! Amenities include Community Pool, Tennis and Pickleball Courts, Clubhouse with Fitness Center, Boat Dock (subject to availability), Kayak launch and storage, Gazebo with BBQ, etc. Blackburn Harbor is ideally situated in Osprey between Sarasota and Venice and is just minutes minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer!
#A4631433

OSPREY

2251 JESSIE HARBOR DRIVE 2101

2 Beds

2 Baths

1,400 Sq.Ft.

$395,000

MLS#: A4631433

Price reduced
The only available home in the community with a 2 Car Garage! Welcome to Bay Street Village, a charming, beach-close, gated community in sought-after Osprey. This rarely available First-Floor residence features an oversized two-car garage with exceptional space for vehicles, bikes, kayaks, and all your Florida adventure gear. Ideally situated on a quiet cul-de-sac with peaceful pond views, this light-filled, move-in-ready home offers tranquil water vistas from both the interior and the screened lanai. The open-concept floor plan flows effortlessly, creating a comfortable and inviting living space. The owner’s suite enjoys serene pond views, while the guest bedroom is thoughtfully positioned on the opposite side of the home, adjacent to a well-appointed full bath. A stylish office/den with double-door entry provides flexible space for working from home or accommodating overnight guests. The kitchen features, stainless appliances, granite countertops along with an island with seating, and a walk-in pantry. Built with solid concrete block construction, this home includes impact windows for added peace of mind and a new (Oct 2025) HVAC system. Additional highlights include water and sewer included in the low HOA fee, no CDD fees, and a pet-friendly community. Bay Street Village offers resort-style amenities, including a heated pool, fitness room, and clubhouse—all just a short walk from your front door. Ideally located between Sarasota and Venice, you’ll enjoy easy access to shopping, dining, theater, fishing piers, kayak launches, and the Legacy Bike Trail. World-famous beaches and resorts, including Siesta Key, are just minutes away. This is a rare opportunity to own a beautiful, affordable Florida lifestyle retreat.
#N6142473

OSPREY

124 REVOLUTION WAY

2 Beds

2 Baths

1,574 Sq.Ft.

$388,000

MLS#: N6142473

Welcome to Bay Street Village, a gated, maintenance-free community in Osprey between Sarasota and Venice. The tile roofs and paver driveway provide Florida charm. This move-in-ready 3-bed, 2-bath condo features an open layout, IMPACT glass, and a private screened balcony with a pond view. The kitchen offers a large granite counter with seating and a newer refrigerator. The primary suite includes a walk-in closet and an en-suite bath with dual sinks and a step-in shower. A split floorplan adds privacy, and the attached one-car garage provides extra storage. Community amenities include a heated pool, fitness center, and clubhouse. Bay Street Park is directly across the street and is walkable—includes a dog park for your furry friend. Water is included in the monthly fee. Conveniently located near Nokomis Beach, Oscar Scherer State Park, The Legacy Trail, Publix, restaurants, shopping, and both US-41 and I-75, this condo offers easy, low-maintenance Florida living in a central coastal location in a very nice community.
#A4681835

OSPREY

4284 EXPEDITION WAY NA

3 Beds

2 Baths

1,430 Sq.Ft.

$350,000

MLS#: A4681835

Price reduced
*Open to discussing concessions with any reasonable offer* Sophisticated Office Condo in Prime Osprey Location – Act Now! Seize the opportunity to elevate your business in the prestigious Gulf Coast community of Osprey, FL. Positioned strategically on Tamiami Trail (US-41) between the cultural heart of Sarasota and the pristine beaches of Venice, this exceptional office condo places you in the epicenter of business and leisure. With seamless access to major highways, airports, and ports, your company will enjoy unmatched connectivity, opening doors to endless growth and networking potential. Osprey, nestled in the thriving Sarasota County, is renowned for its dynamic business ecosystem—fostering innovation, entrepreneurship, and economic vitality. This is more than just a location; it’s a chance to become part of a forward-thinking community dedicated to success. Surrounded by lush landscapes, serene waterways, and the nearby Gulf of Mexico, your team will thrive in an inspiring and sophisticated environment. Key Features: • Reception/Waiting Room that exudes professionalism • Spacious cubicles and 2 private offices for focused productivity • 1 Executive Conference Room, ideal for high-level meetings • Convenient kitchenette/breakroom for employee comfort • 1 In-suite restrooms for added convenience • Ample parking for your team and visitors • Quarterly HOA dues: $945 Don’t miss out on the chance to secure this stunning office space in one of the region’s most sought-after locations. The demand for spaces like this is high, and opportunities this exceptional won’t last long. Invest in your business’s future today—before it's gone!
#A4648348

OSPREY

436 S TAMIAMI TRAIL C4

None Beds

None Baths

1,272 Sq.Ft.

$350,000

MLS#: A4648348

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.

$330,000

MLS#: N6140508

Rarely available Windsor Lodge efficiency condominium located within The Oaks Club. This second-floor, maintenance-free, lakeside unit features a covered balcony with views of the lake, pool, and golf course. Elevator access to the second floor. Short-term rentals permitted. Enjoy the country club lifestyle at The Oaks Club, a private, member-owned club in Osprey, Florida. Mandatory membership required with purchase. Amenities include two championship 18-hole golf courses, twelve tennis courts, four pickleball courts, a state-of-the-art Fitness/WellFit Center, croquet courts, clubhouse with three restaurants, banquet facilities, and an active social calendar.
#A4679180

OSPREY

51 MACEWEN DRIVE 11

1 Beds

1 Baths

623 Sq.Ft.

$300,000

MLS#: A4679180

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

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!
#A4671600

OSPREY

232 WOODLAND DRIVE 232

2 Beds

2 Baths

1,325 Sq.Ft.

$264,900

MLS#: A4671600

New on site 4 days ago
Tucked away in the charming community of Pine Run, this uniquely designed two-story condo offers the perfect blend of privacy, comfort, and Florida lifestyle living in the heart of Osprey. This spacious 2-bedroom, 2-bath residence features a layout offering the primary suite on the first floor—ideal for ease of living and added privacy. The main level offers an inviting living and dining area filled with natural light, creating a warm and welcoming space for both relaxing and entertaining. The primary bedroom retreat provides generous space, ample closet storage, and a well-appointed en-suite bath. Upstairs, you’ll find a loft that is designed to be the second bedroom and full bath, perfect for guests, a home office, or seasonal visitors. The two-story design enhances privacy while maintaining an open and airy feel throughout. Pine Run is truly a hidden gem, known for its lush, mature landscaping and tranquil setting. Residents enjoy a peaceful, maintenance-free lifestyle just minutes from Gulf beaches, waterfront dining, shopping, and the cultural attractions of Sarasota. Whether you’re searching for a full-time residence or a seasonal retreat, this condo offers the ideal combination of comfort, location, and relaxed coastal living.
#A4684191

OSPREY

211 WOODLAND DRIVE 211

2 Beds

2 Baths

1,223 Sq.Ft.

$200,000

MLS#: A4684191

Price reduced
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.

$200,000

MLS#: A4667419

Live among the trees! This condo is nestled in one of the most desirable areas of Pine Run. Outside your living room/kitchen sliders, all you see are a greenbelt and trees, creating a sense of ultimate privacy. The property has been updated, and some of the many special features include: soaring ceilings, outdoor spaces off of the living room, kitchen & bedrooms, stainless appliances, wood flooring, blackout shades for all sliders, and so much more. Whether you are looking to live here full-time or seasonally, Pine Run is a community of friendly, active, pet-loving residents! Regular activities include tennis, pickle ball, group bike rides, movie nights, a social club, Friday night gatherings at the clubhouse, and a party for almost every holiday. Be as active as you want to be. 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, Deep Lagoon restaurant, and shopping are all within walking or biking distance.
#A4683173

OSPREY

354 PINE RUN DRIVE

2 Beds

2 Baths

1,224 Sq.Ft.

$200,000

MLS#: A4683173

Discover an exceptional opportunity to create your custom dream home in the heart of Osprey — one of Sarasota County’s most desirable coastal communities. This buildable vacant homesite offers the perfect canvas to design a private retreat tailored to your lifestyle, all while enjoying the charm, convenience, and natural beauty of Florida’s Gulf Coast. With over 7,000 square feet of buildable area on the ground level alone, the possibilities are truly expansive. Whether you envision a sprawling single-story estate or a multi-level architectural masterpiece, there is ample room to bring your vision to life. The generous footprint allows space for: A luxurious primary residence A private ADU (Accessory Dwelling Unit) for guests or extended family Dedicated RV parking or a custom RV garage Outdoor living areas, pool, and entertaining spaces The property is graced with mature trees, providing natural shade, character, and the opportunity to design a home that blends seamlessly with the surrounding landscape. The established greenery enhances privacy and creates a serene setting that feels tucked away, yet connected. Location is everything — and this homesite delivers. Conveniently located near nationally recognized schools, the area is highly sought after for its top-tier education and strong community appeal. Residents enjoy easy access to nearby beaches, parks, boating, golf, shopping, and dining throughout Osprey, Nokomis, and Sarasota. Build without compromise. Design without limits. This is your opportunity to secure a prime homesite in Osprey and create the Florida lifestyle you’ve always imagined. Renderings are available. One of the closest buildable lots in the proximity of Pine View School!
#A4682477

OSPREY

14 OLD VENICE ROAD

None Beds

None Baths

0.48 acres

$190,000

MLS#: A4682477

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