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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

$250,000 - $500,000

144 Properties Found. Page 8 of 10.

#A4656074

OSPREY

4428 CONCHFISH LANE

4 Beds

2 Baths

1,861 Sq.Ft.

$548,000

MLS#: A4656074

Beautiful residence located in The Palms of Casey Key community, offering a thoughtfully designed layout ideal for everyday living and entertaining. Offers 1% lender credit at closing.

The home spans approximately 2,000+ square feet and features updated flooring throughout all bedrooms and closets, along with tile in the main living areas for durability and easy upkeep. A spacious great room anchors the interior, creating a natural gathering space for family and guests, while the private primary suite is set apart at the rear of the home and includes dual sinks, a soaking tub, walk-in shower, and generous closet space.

Outdoor living is highlighted by a covered lanai overlooking a private backyard, ideal for relaxing or entertaining. Additional features include a two-car garage and a well-maintained neighborhood setting with HOA oversight and community amenities nearby. Positioned just steps from Pine View School, it also provides convenient access to US-41 and I-75, placing top-rated schools, beaches, marinas, dining, and shopping just minutes away.

OSPREY

4429 CONCHFISH LANE

3 Beds

2 Baths

2,004 Sq.Ft.

$535,000

MLS#: A4689967

Price reduced

One or more photo(s) has been virtually staged. Beautiful home in the desirable Bay Oaks neighborhood, known for its winding roads, mature landscaping, and minimal traffic. Perfectly situated between The Oaks Golf Course and Stoneybrook Golf & Country Club, this home offers the lifestyle and views without the high price tag or association fees.
The property welcomes you with a circular driveway, new roof (2018), fenced yard, and freshly pressure-washed exterior(2026) with updated landscaping (2026).
Double French doors open to a grand foyer with soaring ceilings and immediate views of the family room, pool, and backyard, creating a Florida grand entrance. The entire interior of the home was repainted (2026). A dedicated office with French doors and a formal dining room, both overlook the front yard.
The spacious primary suite features new porcelain tile flooring, two walk-in closets, and pocket sliders that open to the newly rescreened lanai (2026), perfect for enjoying stunning west coast sunsets year-round. The primary bathroom includes a new double-sink vanity, a private water closet with a pocket door, and a separate tub and shower.
The kitchen offers a built-in pantry, space for a breakfast table, and uniquely angled countertops and bar that maximize outdoor views. Enjoy peekaboo views of The Oaks golf course through the third set of sliding glass doors and corner windows.
The second living area continues the vaulted ceilings and is filled with southwest-facing natural light. An updated half bath with direct pool access adds convenience.
A pocket door separates the split floor plan, leading to two additional bedrooms and a full bathroom with tub/shower combo, new vanity, and porcelain flooring.
At the heart of the home is the covered and newly rescreened lanai. The recently refinished pool (2025) pool pump (2026) with water features, completed by award-winning Platinum Pools, create a relaxed setting. The fenced backyard offers privacy, with the option to open up more golf course views at the owner’s request (through The Oaks Club and at no additional expense).
Additional features include an interior laundry room with a sink, located just off the two-car garage with refinished floors (2026), an exterior access door, and whole house replumbed (2018).
This home offers a highly functional layout, with many major updates already completed for peace of mind and quick move-in, while still allowing room for your personal touch.
Located just 6 miles from Siesta Key (#1 beach in America), 4 miles to Casey Key, and close to multiple local marinas, golf courses, and the Legacy Trail. Also conveniently located near major shopping, including Costco, grocery stores, pharmacies, pet stores, restaurants, Starbucks, and Nordstrom Rack, as well as an upcoming development featuring Whole Foods, Chipotle, Sprouts, and more.
This is a home you need to experience in person. Schedule your private showing today!

OSPREY

562 OAK BAY DRIVE

3 Beds

2 Baths

2,414 Sq.Ft.

$530,000

MLS#: A4690387

Boat Slips included, Insurance included, Ground maintenance included!!Secluded waterfront community on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf. Heron Bay Club has boat slips available! This small community on Little Sarasota Bay offers striking sunsets. Across from the northern section of Casey Key, the 10-acre property features 26 villas. This complex is intimate, quiet and peaceful. Part of the reason for the relaxing atmosphere is that Heron Bay Club lies off the beaten track. All villas have a courtyard entry, which creates a big, sheltered outdoor living area. This home has unmatched waterfront views from most rooms. 786 Sarabay has been updated and is move-in ready. The HOA fee covers all the community amenities which include a new Trex deck dock for your boat, a fishing pier and fish cleaning station, kayak and paddle board launches, a heated swimming pool, a tiki hut to enjoy sunsets, tennis courts along with maintenance-free grounds. Also included in the HOA fee is water, cable, internet along with insurance and roofs. You will not find another villa with as much storage as this unit due to the attached two-car garage. This villa is a short distance to all Sarasota has to offer such as beaches, the arts and shopping. Visit Heron Bay Club and make it your new home!

OSPREY

786 SARABAY ROAD 19

2 Beds

2 Baths

1,555 Sq.Ft.

$519,000

MLS#: A4677900

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!

OSPREY

7303 JESSIE HARBOR DRIVE 7303

3 Beds

2 Baths

1,883 Sq.Ft.

$474,900

MLS#: D6142543

One or more photo(s) has been virtually staged. Live the Florida dream on the water! Wake up to shimmering bay views, spend your days boating and fishing, and end every evening with breathtaking sunsets over Little Sarasota Bay, all from this rarely available, maintenance-free waterfront villa. In the exclusive Heron Bay Club, an intimate bayfront enclave of just 25 villas set across 10 beautifully manicured acres, this home offers the ultimate Florida lifestyle. Enjoy resort-style amenities including a heated waterfront pool, tennis courts, kayak launch, fishing pier, and community docks with water and electric. Best of all, there are 10 free boat slips with no fixed bridges to the Gulf, making this a boater’s paradise, so bring your boat and go! This spacious two-bedroom, two-bath villa features sweeping views of Little Sarasota Bay, the Intracoastal Waterway, the community pond and pool. The open concept floor plan is enhanced by 15-foot ceilings, abundant natural light, and seamless indoor-outdoor living. Relax on the screened lanai, cool off in your heated waterfront pool and enjoy nightly sunsets that never get old. A private gated courtyard entry sets the tone for this unique home, complete with a new paved walkway and pet-friendly artificial turf, completely maintenance-free. Inside, enjoy ES Prestige impact-rated windows and sliding glass doors, all-new kitchen appliances, and an eat-in kitchen overlooking the courtyard. The primary suite offers lanai access through sliding glass doors and features two custom walk-in closets. The second bedroom also opens to the private courtyard and includes its covered lanai, perfect for guests or a home office retreat. Conveniently with quick access to Interstate 75, shopping, dining and beaches, this exceptional waterfront villa delivers boating, fishing, views and effortless Florida living in one remarkable package. A rare opportunity, this is waterfront living at its finest. Schedule your private showing today.

OSPREY

764 SARABAY ROAD 8

2 Beds

2 Baths

1,392 Sq.Ft.

$450,000

MLS#: A4683747

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!

OSPREY

352 GLENWOOD AVE

3 Beds

2 Baths

1,300 Sq.Ft.

$429,500

MLS#: N6138982

One or more photo(s) has been virtually staged. Welcome to your private poolside retreat in the desirable coastal community of Osprey—
perfectly situated on a premium corner lot with NO HOA and NO CDD fees!
This beautiful 3-bedroom, 2-bath home offers a bright, open-concept layout designed for
both everyday comfort and effortless entertaining. The spacious living area features sliding
glass doors that lead directly to your screened-in lanai and sparkling inground pool, creating
seamless indoor-outdoor living.
The well-equipped kitchen boasts abundant cabinetry and generous counter space, making it
ideal for preparing meals and hosting gatherings. Each of the three bedrooms includes a walk-
in closet, providing ample storage and convenience.
Retreat to the primary suite, where you’ll find a spa-like jetted tub—perfect for unwinding
after a long day. Step outside and enjoy the added bonus of an outdoor shower, ideal for rinsing
off after a swim.
Additional highlights include a two-car garage, functional layout, and a yard that offers both
privacy and potential.
With its corner lot location and private pool this home delivers the ultimate Florida lifestyle.
Opportunities like this don’t last—schedule your private showing today and make this
Osprey gem yours!

OSPREY

212 WASHINGTON AVENUE

3 Beds

2 Baths

1,478 Sq.Ft.

$427,000

MLS#: O6404307

Price reduced

This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from the living room, dining room, kitchen and primary bedroom to a spacious screened porch that overlooks a scenic pond and expansive yard. Whether entertaining guests or enjoying a quiet morning coffee, the outdoor living space extends your home beautifully. The kitchen is stylish and functional, offering gently used stainless KitchenAid Gallery appliances, space-saving self-closing cabinetry, and a generous open breakfast bar ideal for casual dining and gathering. Baths have been tastefully modernized with updated cabinets, countertops, fixtures and lighting. Major improvements provide peace of mind, including 2025 sewer pipes relined, a 2022 air-conditioning system, 2015 re-roof, 2015 hurricane-impact windows, 2015 gutters plus interior and exterior paint, and refreshed landscaping. Additional highlights include a two-car attached garage, dedicated workshop space and access to boat docks (Contact HOA for details). Ideally West of the Trail between Sarasota and Venice, with convenient access to Highway 681 and Interstate 75, this home places you close to everything. Top-rated schools nearby include Pine View School for gifted and Venice High School, known for strong sports and arts programs. Outdoor enthusiasts will love being just 5 to 10 minutes from Nokomis Beach, Blackburn Point Park kayak and boat launch, Oscar Scherer State Park, offering hiking, camping, cycling, kayaking, boating and fishing, and the Legacy Trail, which is ideal for biking with family or friends. Dining options abound, including waterfront favorites nearby. This is Florida living at its finest, with modern design, natural beauty, boating access and an unbeatable location.

OSPREY

107 SORRENTO DRIVE

2 Beds

2 Baths

1,284 Sq.Ft.

$425,000

MLS#: N6143210

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!

OSPREY

1811 HIGHLAND ROAD

2 Beds

2 Baths

1,725 Sq.Ft.

$422,000

MLS#: TB8443161

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.

OSPREY

524 SARABAY ROAD

3 Beds

2 Baths

1,760 Sq.Ft.

$419,000

MLS#: A4676179

Price reduced

ANOTHER REDUCTION! NOW $439,000! Bigger 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.

OSPREY

3976 DESTINATION DRIVE 102

None Beds

None Baths

1,050 Sq.Ft.

$419,000

MLS#: N6142459

Open to discussing concessions with reasonable terms.

Office condo located in Osprey, FL, directly on U.S. Route 41 (Tamiami Trail), positioned between Sarasota and Venice. The location provides straightforward access to major roadways, regional airports, and surrounding commercial centers, supporting day-to-day operations and client accessibility.

Osprey is part of Sarasota County, an area with consistent business activity and continued growth across professional services, healthcare, and small business sectors. The setting offers a balance of accessibility and a quieter environment compared to higher-density markets.

Key Features
Reception / waiting area
Multiple cubicle workspaces
Two private offices
Conference room suitable for team or client meetings
Kitchenette / break area
In-suite restroom
Ample on-site parking

Quarterly HOA dues: $1215.

This space is well-suited for businesses seeking a functional layout in a central Gulf Coast location with strong regional access.

OSPREY

436 S TAMIAMI TRAIL C4

None Beds

None Baths

1,272 Sq.Ft.

$350,000

MLS#: A4648348

**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!

OSPREY

2251 JESSIE HARBOR DRIVE 2101

2 Beds

2 Baths

1,400 Sq.Ft.

$349,000

MLS#: A4631433

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.

OSPREY

4284 EXPEDITION WAY NA

3 Beds

2 Baths

1,430 Sq.Ft.

$339,900

MLS#: A4681835

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