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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
157
# of Listings
3
Avg # of Bedrooms
$528
Avg. $ / Sq.Ft.
$1,241,103
Med. List Price

Browse Osprey Real Estate Listings

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Over $5M

19 Properties Found. Page 1 of 2.

PENTHOUSE CONDO IN WATERFRONT COMMUNITY! Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for soaking up the Florida sunshine and enjoying great views. The gourmet kitchen is a chef’s dream, offering granite countertops, wood cabinetry, stainless steel appliances, and a cozy eat-in area for casual dining. The expansive master suite boasts a private balcony, two walk-in closets, double vanities, a soaking tub, and a separate shower for ultimate relaxation. Additional highlights include a wet bar for entertaining and three separate balconies for outdoor living. Enjoy resort-style amenities such as tennis courts, pickleball, shuffleboard, a heated pool, clubhouse, walking paths, a workout facility, and a convenient kayak launch for endless waterfront adventures. Bring your own boat and take advantage of your separately available assigned boat dock area! When you’re ready to explore, you’ll find yourself just 10 minutes from several Gulf Coast beaches, thousands of acres of parks and preserves, and world-class shopping, dining, and fishing. Quick connections to Sarasota’s vibrant arts scene, the new Mote Marine Aquarium, Spanish Point, the Legacy Trail, and Oscar Scherer State Park are all just minutes away. All of this and you will just be 5 minutes from I-75 where the rest of the world awaits you. Take the elevator to your nearby 2 assigned parking spots under the building. Don’t miss your chance to own this exceptional penthouse—schedule your private showing today!
#D6142543

OSPREY

7303 JESSIE HARBOR DRIVE 7303

3 Beds

2 Baths

1,883 Sq.Ft.

$474,900

MLS#: D6142543

Price reduced
NOW $449,000! Big Price Improvement! Seller is ready to make a deal! EXCEPTIONAL OPPORTUNITY to OWN & GROW YOUR BUSINESS in an UP-SCALE WATERFRONT WALKING COMMUNITY! First-floor retail-office condominium in the highly regarded Bay Street Commercial Condominium, located in Osprey’s Bayfront Village—one of Sarasota County’s fastest-growing waterfront walking communities. This turn-key, beautifully built-out space is designed to accommodate a wide range of professional uses, including medical, professional services, retail, and boutique office operations. Perfectly positioned for long-term success, the property is set to benefit from significant foot traffic, with approximately 252 luxury multifamily apartment residences currently developed directly behind the town center. The location is further enhanced by close proximity to affluent communities such as The Oaks and nearby luxury bayfront estates, all just minutes away. Inside, the meticulously designed layout features soaring ceilings that create a refined sense of openness and sophistication. No expense was spared in the high-end build-out, with substantial investment dedicated to crafting a luxurious, private, and highly functional professional environment. The thoughtfully designed floor plan includes six private offices, two conference rooms, a bright, professionally appointed lobby with a welcoming reception area, two well-appointed bathrooms, and a convenient kitchenette. Each office is constructed with soundproofed walls and solid hardwood doors, ensuring privacy, comfort, and quiet productivity. Upscale lighting, premium flooring, and modern finishes elevate the space throughout, reinforcing its contemporary, high-end appeal. A rear door provides direct access to ample employee parking, offering convenience and ease for staff. The property also features a charming front porch that may serve as a welcoming seating area with potted plants, a coffee table, and comfortable seating, creating a warm and inviting, home-like first impression for clients, patients, or guests. Ideal for medical, professional, or boutique office use, this property presents a rare opportunity to establish or expand your business within a high-end commercial complex poised for continued growth and long-term value. See attached Feature Lists for additional details about the community and Unit 201.
#N6142459

OSPREY

3976 DESTINATION DRIVE 102

None Beds

None Baths

1,050 Sq.Ft.

$449,000

MLS#: N6142459

Price reduced
PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in Florida, or for anyone looking to downsize without sacrificing comfort or style. Residents enjoy the best of the Florida lifestyle, with close proximity to beautiful beaches-just 2 stoplights away. Additionally, the community is near parks, arts venues, shopping, and restaurants, making it perfect for both active living and peaceful retreat. This home has been thoughtfully updated with new porcelain "wood-look" tile throughout most of the living space, a renovated guest bathroom featuring a walk-in shower, fresh interior paint, and a new roof installed in 2021. The neighborhood is located in one of Sarasota County's top school districts, with Pine View School just a few minutes away. Just a short walk up the street, the community clubhouse offers a generously sized pool, perfect for swimming and social gatherings. Whether you're seeking tranquil relaxation or active outdoor adventures, this exceptional property and community provide the perfect balance. Notice- Some photos of the property have been Virtually Staged.
#A4664579

OSPREY

508 MEADOW SWEET CIRCLE

2 Beds

2 Baths

1,604 Sq.Ft.

$445,000

MLS#: A4664579

Price reduced
Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless steel appliances—all completed in 2022. Yard was completely fenced in 2024. With ample square footage, there’s even potential to add a third bedroom, offering flexibility for your needs. All major systems have been upgraded; now this home is waiting for your personal touch. The oversized garage with over 500 SF has sliding doors leading to the backyard and side-yard. Large 15,500 SF of land there is ample space to add a pool. This home has a split bedroom layout and 2 bathrooms (one en-suite; other could be made en-suite). Not located in a high risk flood zone. The Bay Acres community features a private waterfront park on a protected bay with dockage for boats up to 22 feet, a kayak launch, and storage for kayaks and paddleboards. There’s also a shaded picnic area for relaxing or entertaining. Boaters will love the direct access to the water from the 12-slip community boat basin, with slips available by waitlist. For larger vessels, Blackburn Point Park Boat Ramp is just 1.5 miles away. Located just minutes from Casey Key, Siesta Key, and the A+ rated Pine View School, this property is ideal for boaters, beachgoers, and families alike. Nearby attractions include Oscar Scherer State Park, Selby’s Historic Spanish Point, and The Legacy Trail, while Downtown Sarasota and Venice have plenty of shopping, dining, and entertainment options. Bay Acres is a non-deed-restricted neighborhood, giving you the freedom to park your boat, trailer, or RV without the hassle of HOA restrictions. All the hard work has been done—now it’s time to make this your own piece of paradise.
#N6140978

OSPREY

32 BAY AVENUE

2 Beds

2 Baths

2,148 Sq.Ft.

$437,000

MLS#: N6140978

PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches. Walking distance to Casey Key Mainland (Chef Rolfs), private community Shoreland Park & Oscar Scherer State Park. Minutes away from COSTCO, Publix, Target, Richard's, YMCA Potter Park, waterfront dining (Casey Key Fish House & Tiki bar - waterfront , Spanish Point restaurant & Tiki Bar. The townhouse is close to Laurel Rd and Sarasota Memorial Hospital. Property is managed by owner. Timely response to accommodate your needs. Summary of amenities: PARKING: 2-CAR TANDEM GARAGE HOA PRIVATE COMMUNITY 1 BLOCK FROM INTERCOASTAL SCREENED BALCONY CEILING FANS VAULTED CEILING CENTRAL AIR UPGRADED TALL CABINETS GRANITE COUNTERTOP STAINLESS STEEL APPLIANCES CONVECTION RANGE/OVEN/AIRFRYER MICROWAVE DISHWASHER IN-SINK DISPOSAL SMART REFRIGERATOR DINING ROOM & FAMILY ROOM MASTER BEDROOM WITH WALK-IN CLOSET MASTER BATH GUEST BEDROOM ADDITIONAL STORAGE IN LOWER FLOOR OR GARAGE AIR CONDITIONING WASHER/DRYER SPRINKLER SYSTEM COMMUNITY SWIMMING POOL WITH LOUNGE CHAIRS + USE OF CASEY KEY MAINLAND POOL WALK/BIKE TO TOP RATED PINEVIEW SCHOOL, WALLMART, POST OFFICE, LEGACY BIKE TRAIL CLOSE TO SIESTA KEY, NOKOMIS BEACH, VENICE BEACH, OSCAR SCHERER STATE PARK HUGE FURNISHED BONUS ROOM ON FIRST FLOOR OUTDOOR GRILL Turn-key ready!
#TB8443161

OSPREY

1811 HIGHLAND ROAD

2 Beds

2 Baths

1,725 Sq.Ft.

$433,000

MLS#: TB8443161

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

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.

$424,000

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

Excellent location! Corner lot Zoned CG (Commercial General) with 117 feet of frontage on US 41 in Osprey, just north of Bay Street. Prime area of growth in Sarasota County next to Calico Corners, Bay St., Spanish Point restaurants, Sarasota crew and Super Walmart. Perfect opportunity for your own business or investment. Great accessibility on 3 sides for ingress and egress (US 41, Shumard, and Columbia). 11,433 sq ft per survey;117 feet on US 41, 117 feet on Columbia, 102 feet on Shumard, and 96 feet on North lot line. Vacant lot: no buildings on the property. Plat map and survey on attachments. There is a bus stop on the sidewalk on 41. Listing agent is owner.
#A4638654

OSPREY

51 N TAMIAMI TRAIL

None Beds

None Baths

0.24 acres

$395,000

MLS#: A4638654

**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

*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.

$374,900

MLS#: A4648348

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

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

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!
#A4658738

OSPREY

116 NAVIGATION CIRCLE 106

3 Beds

2 Baths

1,430 Sq.Ft.

$325,000

MLS#: A4658738

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