Displaying: For Sale
Location: Osprey
Property Type(s): Condos
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Osprey - 45 properties found
1116 BEACHCOMBER CT #3, OSPREY, FL 34229
$545,00032 Days on yellowkey MLS ID: A4688310
1 Days Off yellowkey (back on 5/5/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2040 Built: 2005Monthly Fee: $1,133 Tax: $5,376 (2025)Community: Blackburn Point Marina VillageCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,376
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: Under contract-accepting backup offers. LOCATION, LOCATION, LOCATION! Nestled within the highly desirable gated enclave of Blackburn Point Marina Village, this beautifully maintained 3-bed, 2.5 bath residence is ready to welcome its new owners. This bright and airy two-story unit features soaring ceilings and a spacious open floor plan, creating an inviting and comfortable living environment. The main living areas are enhanced with tile flooring and flow seamlessly into a well-appointed kitchen, complete with Corian countertops, a breakfast bar, center island, closet pantry, and stainless-steel appliances, perfect for both everyday living and entertaining. The dining area features pocketing sliders that extend the living space to the enclosed lanai, already plumbed for a full outdoor kitchen, offering the ideal indoor-outdoor Florida lifestyle. The primary suite is conveniently located on the ground floor and offers a private retreat with an ensuite bathroom featuring dual vanities, a garden tub, and a walk-in shower. Upstairs, two additional bedrooms and a full bath provide privacy and comfort for guests or family. Step outside to the patio, an ideal setting to relax and enjoy a quiet afternoon or evening cocktail in the Florida sunshine. Additional features include an oversized one-car garage with under-stair storage, a new A/C system (2025), and a new roof (2025), providing peace of mind for years to come. Residents of Blackburn Marina Village enjoy access to a heated community pool, a fully equipped outdoor kitchen, and a vibrant social calendar for those who wish to participate. Ideally located with easy access to Gulf beaches, Blackburn Point Marina, dining, and shopping, this exceptional property truly offers the best of Florida living!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Christine Green (941-914-2463)
6100 JESSIE HARBOR DR #202, OSPREY, FL 34229
$850,0001 Day on yellowkey MLS ID: A4690969
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 3771 Built: 2005Monthly Fee: $1,101 Tax: $8,698 (2025)Community: Blackburn Harbor ResidencesCondo
Taxes:$8,698
Elementary School: None
High School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County. Situated on the second floor (building with elevator), this elegant 3 bedroom with a den/office condominium offers a harmonious blend of style and comfort, complemented by serene marina views. The open-concept layout features expansive living and dining spaces bathed in natural light, perfect for both everyday living and effortless entertaining. Sliding glass doors lead to a generous wrap-around lanai, creating a seamless indoor-outdoor setting to relax and enjoy tranquil water views, refreshing coastal breezes and spectacular sunsets. The gourmet kitchen is as functional as it is inviting, showcasing rich wood cabinetry, granite countertops, stainless steel appliances, a center island for culinary enthusiasts, and a cozy dinette. A convenient breakfast bar opens to the main living area, ideal for casual dining and social gatherings. The primary suite serves as a peaceful retreat, complete with ample closet space and a well-appointed en-suite bath. Each additional bedroom features its own en-suite bathroom and walk-in closets, offering comfort and privacy for guests or versatility for a home office. Residents of Blackburn Harbor enjoy an array of resort-style amenities, including a heated pool, fitness center, clubhouse, tennis and pickleball courts, kayak storage and launch, and a gazebo with grilling areas. Boating enthusiasts will appreciate the protected deep-water dockage with power and water, and direct access to the Intracoastal Waterway with no bridges. Surrounded by natural beauty, the community provides a front-row seat to Florida’s coastal wildlife, including dolphins and manatees. Just across the street, Oscar Scherer State Park offers scenic trails and outdoor recreation, while nearby waterways invite kayaking adventures to local favorites like Casey Key. Perfectly positioned between Venice (10 minutes) and Sarasota (25 minutes), this location offers convenient access to shopping, dining, and cultural attractions, as well as world-renowned Gulf beaches, including Siesta Key Beach just 15 minutes away. Whether you’re seeking a seasonal escape or a year-round residence, this exceptional property captures the essence of Florida waterfront living.
Listing is courtesy of: CORCORAN DWELLINGS REALTY (941-200-4663)
Listing Agent: Angelic Tassos (917-450-0316)
4271 EXPEDITION WAY #103, OSPREY, FL 34229
$290,00025 Days on yellowkey MLS ID: A4689541
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2017 Tax: $3,507 (2025)Community: Bay Street VillageCondo
Taxes:$3,507
Remarks: 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.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
5100 JESSIE HARBOR DR #304, OSPREY, FL 34229
$735,00013 Days on yellowkey MLS ID: A4690942
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2143 Built: 2004 Tax: $6,004 (2025)Community: Blackburn Harbor ResidencesCondo
Taxes:$6,004
Remarks: Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining area, kitchen, and primary suite. This spacious, designer-furnished home showcases quartz surfaces, tile and luxury vinyl flooring, a primary suite with balcony access, oversized shower, jacuzzi tub, and three closets. This unit includes a beautifully appointed second bedroom and a versatile den that is currently used as a 3rd bedroom. There is ample storage inside and out- including a first-floor storage unit ideal for all your water toys. Use the community kayak launch for access to Blackburn Harbor and Oscar Scherer State Park. Enjoy the rare opportunity to keep your boat in your backyard with dockage currently available. Your home is set within an 11-acre gated community featuring walking trails, tennis and pickleball courts, a resort-style pool, waterside grill, clubhouse, and fitness center, all just minutes from Nokomis Beach, the Legacy Trail, and vibrant dining and shopping—this is truly the ultimate Florida waterfront lifestyle you’ve been waiting for.
Listing Agent: Suki Scollo (941-587-2289)
260 HIDDEN BAY DR #304, OSPREY, FL 34229
$694,00077 Days on yellowkey MLS ID: N6142969
REDUCED by $5,000 (0.7%) on 04/14/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1950 Built: 2019 Tax: $6,342 (2025)Community: Edgewater/Hidden Bay Ph 2 BldgSpa: YesCondo
Taxes:$6,342
Remarks: The Boca Residence: Spacious Living & Resort Style Discover a condominium that offers the true scale and functionality of a private home. The Boca floor plan features a thoughtfully designed two-bedroom plus den, two-and-a-half-bathroom layout, perfect for those who want the ease of condo living without sacrificing space. Whether you are looking for a full-time residence or a spacious seasonal getaway, this home provides a comfortable and highly livable environment. The experience begins with a proper foyer entry that opens into expansive living and dining areas, ideal for hosting family and friends. A dedicated den offers great flexibility as a home office, hobby room, or guest space. This residence is designed for privacy with a split-bedroom configuration, while the additional powder room adds everyday convenience for guests. High ceilings, generous room sizes, and multiple walk-in closets are complemented by a large private terrace that extends your living space outdoors. Beyond the front door, the community offers a host of resort-style amenities. Enjoy a heated pool and spa, a social clubhouse, a fitness center, and courts for both tennis and pickleball. A scenic boardwalk leads to outdoor grilling stations and a tropical Tiki hut gathering area, perfect for weekend get-togethers. To truly experience the lifestyle this home offers, we invite you to schedule your private tour during the sunset hour to see the incredible views that make this residence so special.
Listing is courtesy of: ENGEL & VOELKERS VENICE DOWNTOWN (941-388-9800)
Listing Agent: Janice Martin (941-225-9843)
4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229
$329,50060 Days on yellowkey MLS ID: N6143250
REDUCED by $400 (0.1%) on 04/19/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1528 Built: 2018 Tax: $3,781 (2025)Community: Bay Street VillageCondo
Taxes:$3,781
Middle School: Sarasota Middle
Remarks: One or more photo(s) has been virtually staged. Spectacular water views from most windows in this immaculate, lightly used 3BR/2BA condo, built in 2018 and located in the gated community of Bay Street Villages. The popular Ibis floor plan offers an open-concept kitchen, dining, and great room with designer finishes, including white 42” cabinetry, light granite countertops, custom backsplash and stainless-steel appliances. Enjoy peaceful pond views with birds and wildlife from the screened lanai. Quality construction and peace of mind are provided by hurricane-impact windows and doors, concrete block construction, tile roof, and a paver driveway. The primary suite features plantation shutters, a custom ceiling fan with light, custom closet system, linen closet, lighted 10× makeup mirror, and a bidet-ready outlet. The second and third bedrooms also include custom ceiling fans and 2" blinds. The dining area is accented by a custom light fixture and accordion blinds on the balcony sliding doors. The balcony is enhanced with a tropical palm-leaf ceiling fan and outdoor curtains for added shade and comfort. The great room is fitted with plantation shutters for added elegance. A spacious laundry room includes a washer and dryer. Added features-Ring Doorbell, Keyless Entry on Front Door as well as an Exterior Garage door keypad. The monthly condo fee includes water, sewer, exterior and grounds maintenance, gated entry, heated resort-style pool, cabana, fitness center, and club room. No CDD fees. Ideally located near Nokomis Beach, Casey Key, Siesta Key Beach, the Legacy Trail, Sarasota and Venice dining and shopping, Oscar Scherer Park, and A-rated Pine View School. Maintenance-free Florida living at its best.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Tim Weller (941-221-0155)
14021 BELLAGIO WAY #309, OSPREY, FL 34229
$899,99588 Days on yellowkey MLS ID: A4681589
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2199 Built: 2006Monthly Fee: $1,585 Tax: $9,062 (2024)Community: Villas/Harbor VillageSpa: YesCondo
Taxes:$9,062
Tax Year: 2024
Remarks: Enjoy breathtaking sunset views overlooking the intercostal waterway in this boater's paradise, complete with an on-site marina. Discover coastal living in this beautifully updated 3-bedroom, 2.5-bath residence located in Bellagio Harbor Village. Ideally positioned between Sarasota Big Pass and the Venice Jetty, and just minutes from Midnight Pass and the Gulf of Mexico, this home offers easy access to pristine beaches, fine dining, and boutique shopping. Walkable to local restaurants and boat docks, the community is both conveniently located and peacefully serene. Offering 2,199 square feet of thoughtfully designed living space, this residence has been enhanced for comfort and style. Updates include new lighting throughout, featuring four coastal ceiling fans and elegant Caprice chandeliers. The spacious primary suite and two additional bedrooms feature new cordless blinds and window treatments, creating private and tranquil retreats. Bathrooms have been refreshed with new toilets, fresh paint, and an updated vanity in the powder room. The well-appointed kitchen showcases shaker-style cabinetry and enjoys stunning Intracoastal and sunset views. Step onto the private lanai and enjoy seamless indoor-outdoor living with direct access to the pool area. Newly installed retractable screens provide shade and privacy when desired while preserving expansive water views. Outdoor enthusiasts will appreciate the on-site kayak storage and launch area, perfect for exploring the surrounding waterways. Located in southwest Osprey, this exceptional residence offers both a beautiful home and a vibrant waterfront community. Residents enjoy access to a resort-style pool, hot tub, sauna, and open-concept gathering spaces—creating a lifestyle where every day feels like a vacation.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Tristin Hopler (941-735-3520)
51 MACEWEN DR #11, OSPREY, FL 34229
$235,000102 Days on yellowkey MLS ID: A4679180
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 623 Built: 1990Monthly Fee: $142 Tax: $2,367 (2025)Community: The Oaks ClubSpa: NoCondo
Taxes:$2,367
Remarks: Withing the prestigious The Oaks Golf and Country Club, at the Windsor Lodge, this second-floor, maintenance-free, lakeside efficiency features a covered balcony with views of the lake, pool, and golf course. Elevator access to the second floor. Short-term rentals permitted. As an investment, as a weekend get-away or for visiting family and friends: Enjoy the country club lifestyle at The Oaks Club, a private, member-owned club in Osprey, Florida. Mandatory membership required with purchase as first time buyers at The Oaks. 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.
Listing is courtesy of: 342 REAL ESTATE (941-685-0509)
Listing Agent: Sabine Spycher (941-685-0509)
393 N POINT RD #604, OSPREY, FL 34229
$795,000457 Days on yellowkey MLS ID: A4638035
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2778 Built: 2001Monthly Fee: $367 Tax: $9,625 (2024)Community: Meridian At The Oaks PreserveSpa: YesCondo
Taxes:$9,625
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: Immerse yourself in the unparalleled, unobstructed views of Little Sarasota Bay, the Gulf of Mexico and Midnight Pass, with Casey Key and Siesta Key gracing the horizon from this 6th-Floor Corner Unit Condo. Marvel at the gorgeous water views during the day and the stunning sunsets in the evening from your expansive, sweeping balcony, which feels like an additional room. Experience the epitome of seamless indoor-outdoor living in this expansive condo that spans nearly 2,800 square feet. Designed to emulate the ambiance of a single-family home, the open floor plan features a great room, a separate dining area, and a versatile den. The great room impresses with soaring 10-foot ceilings, floor-to-ceiling windows, and sliding doors that effortlessly blend the indoors with the outdoors, leading to a large, screened balcony with breathtaking water views. This harmonious flow floods the living space with natural light and offers a tranquil backdrop of sparkling vistas. The spacious kitchen is a culinary delight, boasting an eat-in area and granite high bar countertops, perfect for casual meals and entertaining guests. The popular split floor plan provides privacy and convenience, featuring 3 bedrooms and 3 baths. The den adds a layer of versatility to the home. The large kitchen includes an eat-in space and granite high bar countertops. The luxurious primary suite is separate from the guest rooms for privacy and includes stunning water views, large walk-in closets, and a luxurious bathroom. Additional features include an elegant entry, and an exclusive private foyer and elevator. The lanai is equipped with electric hurricane shutters ensuring safety and peace of mind. This secure building offers a wonderful lifestyle with private entry and elevator access. This unit is available for purchase fully furnished and is well-maintained. The Oaks community offers a distinguished, 24-hour guarded country club experience with numerous accolades, including Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World. Amenities include three restaurants, a ballroom, two 18-hole championship golf courses, an award-winning racquets program with 12 Har-Tru Hydro-Grid tennis courts, 4 pickleball courts, a wonderful croquet facility, a state-of-the-art fitness center, a junior Olympic heated community swimming pool, bocce, a basketball court, a playground, a 7000 square foot fitness center, a brand new $9,000,000 dining room and bar with outdoor dining overlooking the golf course. Residents of the Meridian enjoy private amenities, including a heated pool and spa, a fitness center, and an outdoor grill. The Oaks provides well-lit sidewalks, ideal for strolls around the 100-acre preserve. It also boasts scenic trails, perfect for biking and walking while taking in the views of nature. The Oaks is just minutes from the nationally ranked Pine View School the Legacy Bike Trail, shopping, and area beaches. It is conveniently situated near both Venice and Sarasota, offering easy access to the amenities and attractions of both cities, while providing a beautiful, luxurious, and well-rounded country club lifestyle. Membership is required, and there is no waitlist for golf or social membership. Be sure to make an appointment to see this stunning condominium **ENJOY THE 3D VIRTUAL TOUR**
Listing is courtesy of: ROBERT SLACK LLC (352-229-1187)
Listing Agent: Debbie Baraona (941-350-8723)
14021 BELLAGIO WAY #404, OSPREY, FL 34229
$1,289,0008 Days on yellowkey MLS ID: N6144070
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2187 Built: 2006Monthly Fee: $1,644 Tax: $5,636 (2025)Community: Villas At Bellagio Harbor VillageCondo
Taxes:$5,636
Remarks: This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comfort and coastal living, set directly on Little Sarasota Bay with sweeping tranquil bay views from the fourth floor. The residence features three spacious bedrooms and three baths all thoughtfully redesigned with high-end finishes. The modern kitchen has been completely renovated and outfitted with new appliances, Hickory cabinetry and elegant Cambria countertops ideal for everyday living and entertaining. Natural light fills the open living spaces, enhanced by hurricane-rated windows and doors throughout for peace of mind. Go onto the north-facing balcony, equipped with automatic hurricane screens and enjoy serene water views year round. A charming Juliet balcony off the guest bedroom adds an extra touch of architectural character and fresh air access. This unit includes two underground parking spaces, conveniently right outside the elevator for effortless access. Boating enthusiasts will appreciate the included 50-foot boat slip accommodating vessels 44 feet, ideal for exploring the Intracoastal Waterway and beyond. Residents enjoy an array of resort-style amenities including a fully equipped fitness center, heated pool, hot tub, sauna and beautifully maintained outdoor spaces. Gather with friends at the outdoor cooking areas, relax by the fire pit, or take advantage of the kayak launch and sunset dock for unforgettable evenings on the water. A welcoming clubhouse provides additional space for socializing and events. Ideally between Sarasota and Venice, this property offers quick and easy access to pristine beaches, scenic parks, the Legacy Trail, top tier medical facilities, a wide selection of fine dining and shopping. This is a rare opportunity to own a move-in ready waterfront condominium that captures the essence of Florida Gulf Coast living. Schedule your private showing today!
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)
Listing Agent: Megan E. George, Pa (941-726-1998)
242 HIDDEN BAY DR #603, OSPREY, FL 34229
$550,000106 Days on yellowkey MLS ID: C7520107
0 Days Off yellowkey (back on 4/29/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1932 Built: 1999 Tax: $4,840 (2025)Community: Hidden BayCondo
Taxes:$4,840
Remarks: Under contract-accepting backup offers. Stunning, unobstructed views of the Intracoastal Waterway, Little Sarasota Bay, and the Gulf await from this beautiful Penthouse residence in Baypoint Vista, Osprey. Located within Hidden Bay, a gated and amenity rich community, this exceptional condo features 2 Bedrooms, 2 Bathrooms plus a versatile Den, an open floor plan, high ceilings, recessed lighting, a spacious kitchen, morning room, IMPACT WINDOWS AND SLIDERS, and a 2 Car Garage. The oversized primary suite is a private retreat with breath taking water views, complete with two walk-in closets, a linen closet, and a spa-like bathroom featuring a jetted soaking tub, walk-in shower, double vanity with makeup counter, and a private water closet. The second bedroom includes its own walk-in closet and en-suite bathroom, providing comfort and privacy for guests. Convenient inside utility room equipped with washer, dryer, and a separate wash basin for added functionality. Hidden Bay is a gated resort style community with a heated resort-style pool with waterfalls and lagoon style pond, hot tub, Clubhouse with library, gourmet kitchen for entertaining, fitness center, tennis and pickleball courts, fishing pier, kayak launch & storage, tiki bar, BBQ grills, Dog park, Scenic boardwalk and nature trails leading to the private pier on the bay, and an active social calendar. HOA fees cover cable, internet, water and sewer. Ideally located between Sarasota and Venice, this prime location is close to Oscar Scherer State Park, award-winning beaches - Venice Beach, Siesta Key and Nokomis, shopping, dining, medical facilities, and airports. Experience upscale waterfront living at its finest!
Listing is courtesy of: RE/MAX PALM (941-929-9090)
Listing Agent: Susan Retzke (941-544-5558)
385 N POINT RD #402, OSPREY, FL 34229
$660,000465 Days on yellowkey MLS ID: A4635708
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2055 Built: 2000Monthly Fee: $400 Tax: $5,877 (2024)Community: Meridian At The Oaks PreserveSpa: NoCondo
Taxes:$5,877
Remarks: **BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW** features 3-BEDS and 3-FULL BATH, Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Impressively Renovated interior which boasts Engineered Hardwood and designer Wood Plank Tile flooring, Plantation Shutters, a well-equipped Kitchen with granite counter seating area, white cabinetry and Stainless-Steel appliances including Bosch etc. The Owner’s Bedroom Suite features a Walk-in Closet, Dual Vanities, Soaking Tub and Stunning, Custom Tiled Shower. The Spacious, Screened Balcony features lovely new tile flooring and automated Hurricane Shutters, offering a PRIVATE and serene setting where you can view wonderful wildlife and Gorgeous Sunsets! This residence offers a single, covered parking space and a climate-controlled storage unit. Meridian Condo residents enjoy private amenities including Heated Pool & Spa, Fitness and Outdoor Grill in addition to The Oaks Club’s main campus of amenities. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
385 N POINT RD #304, OSPREY, FL 34229
$1,100,000109 Days on yellowkey MLS ID: A4678422
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2778 Built: 2000Monthly Fee: $400 Tax: $5,845 (2025)Community: Meridian At The Oaks PreserveCondo
Taxes:$5,845
Remarks: **MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF REFINED LIVING SPACE** features 3 Bedrooms, 3 Full Baths, PLUS a Study/Den (or optional 4th bedroom with walk-in closet), all nestled behind the secure gates of the highly sought-after Oaks Preserve Country Club community. Step off your private elevator foyer into a brilliantly renovated, light-filled interior designed to impress. Premium upgrades include engineered hardwood and tile flooring, a spectacular chef’s kitchen with quartz countertops and high-end appliances, crown molding, and beautifully updated bathrooms throughout. The owner’s suite showcases serene views, private balcony access, a spacious walk-in closet, and a stunningly redesigned spa-inspired primary bath. Enjoy breathtaking western sunset views from the oversized balcony—perfect for relaxing or entertaining. Additional highlights include a climate-controlled storage unit and one covered parking space. Meridian I offers exceptional value with a new roof (2024) and new elevators (2025/2026 – in progress). Residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, plus full access to The Oaks Club’s renowned amenities. A must-see residence combining luxury, space, and lifestyle. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts (4 lighted), 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.
393 N POINT RD #401, OSPREY, FL 34229
$785,00043 Days on yellowkey MLS ID: A4686928
0 Days Off yellowkey (back on 4/27/2026)
REDUCED by $50,000 (6.0%) on 03/31/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2594 Built: 2001Monthly Fee: $400 Tax: $5,733 (2025)Community: Meridian At The Oaks PreserveSpa: YesCondo
Taxes:$5,733
Remarks: Offered Turn-Ker Furnished...This beautifully updated 3 bedroom, 3 bath residence with a den offers exceptional space, style, and privacy in Meridian at The Oaks Preserve. The home features a redesigned kitchen with new appliances and granite countertops, a newer A/C system, and rich wood flooring throughout. As an end unit, it enjoys abundant natural light, and the expansive screened balcony—with electric hurricane shutters—creates a private outdoor retreat with real water views, a rarity from a unit at this level! A private elevator opens directly into the residence, providing an impressive and convenient entry experience. OFFERED TURNKEY FURNISHED, additional highlights include two assigned garage parking spaces and close proximity to the Meridian residents-only pool, spa, and fitness room, making everyday living effortless. Set within The Oaks Preserve, this community delivers the best of care-free country club living. Mandatory membership in The Oaks Club unlocks an unmatched array of amenities, including two championship golf courses, 12 HAR-TRU tennis courts, pickleball courts, an award-winning tennis program, a state-of-the-art fitness center, three dining venues, and a vibrant year-round social calendar.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
232 WOODLAND DR #232, OSPREY, FL 34229
$259,900173 Days on yellowkey MLS ID: A4671600
0 Days Off yellowkey (back on 4/25/2026)
REDUCED by $5,000 (1.9%) on 04/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1980 Tax: $2,202 (2025)Community: Pine Run IiiCondo
Taxes:$2,202
Remarks: Under contract-accepting backup offers. 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!
Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)
Listing Agent: Pat Williams (941-289-6231)
242 HIDDEN BAY DR #602, OSPREY, FL 34229
$700,000102 Days on yellowkey MLS ID: A4678883
REDUCED by $19,000 (2.6%) on 04/23/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1932 Built: 1999 Tax: $7,518 (2025)Community: Baypointe Vista 1Condo
Taxes:$7,518
Remarks: Penthouse Waterfront Residence | Enclosed Sunroom | Private Two-Car Garage | Optional Furnishings | Gated Bayfront Community This 6th-floor penthouse waterfront condominium at Hidden Bay offers unobstructed views of Little Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond Casey Key. Designed to capture light and water views throughout the main living areas, the open floor plan features high ceilings, tall interior doors, and crown molding, creating a bright and welcoming coastal interior. The great room accommodates both living and dining areas and opens to an enclosed waterfront sunroom, an ideal space for morning coffee, sunset views, or quiet time overlooking the bay. The kitchen includes a counter-height breakfast bar, pantry storage, and an adjacent dining nook, offering both function and ease for everyday living or entertaining. A den provides flexible space for a home office or guest use. The primary suite features multiple closets and an en suite bath with dual vanities, a soaking tub, walk-in shower, water closet, and a dedicated makeup vanity area. A second bedroom includes an adjoining bath and walk-in closet. Luxury vinyl flooring has been added in the bedrooms and den. Laundry is located inside the residence. The condominium includes a private, fully enclosed two-car garage. Furnishings are included and may remain or be removed at the buyer’s preference. Hidden Bay is a gated waterfront community set along Little Sarasota Bay, offering a clubhouse with fitness center, heated pool and spa, tennis and pickleball courts, kayak storage and launch, and a boardwalk through mangroves leading to a fishing pier. Located west of US 41 in Osprey, Hidden Bay is conveniently positioned between Sarasota and Venice, with nearby access to shopping, dining, the Legacy Trail, and area beaches.
Listing is courtesy of: FIRST LIGHT REAL ESTATE (941-650-2256)
Listing Agent: Cathy Rustin (941-650-2256)
250 HIDDEN BAY DR #301, OSPREY, FL 34229
$725,000103 Days on yellowkey MLS ID: A4679278
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2168 Built: 2017 Tax: $7,792 (2025)Community: Edgewater At Hidden BaySpa: YesCondo
Taxes:$7,792
Remarks: Enjoy sweeping water views and stunning sunsets over Little Sarasota Bay from this spacious third-floor corner residence in the gated waterfront community of Edgewater at Hidden Bay. Built in 2017 and moved into in Jan 2018, this three-bedroom plus den, 2.5-bath condominium offers nearly 2,200 square feet of living space with easy elevator access and one assigned parking space in the building. The attractive open floor plan features soaring ceilings, impact-rated windows and sliding doors, easy maintenance tile plank flooring and abundant natural light throughout. The kitchen includes granite countertops, solid wood cabinetry, stainless steel appliances and custom storage with pullout drawers. The living area offers a built-in dry bar with wine refrigerator and opens to a large, screened-in terrace with privacy-screens and expansive bay views. The primary suite includes dual walk-in closets and a luxurious bath with dual quartz vanities, decorative tile flooring, makeup vanity and walk-in shower. Additional features include a private den/office, in-unit laundry room, two full baths and a powder room, AC from 2023. Edgewater at Hidden Bay is a gated, resort-style community set on 14 acres along Little Sarasota Bay and the Intracoastal Waterway, directly across from Casey Key. Community amenities include a waterfront clubhouse with kitchen and quartz bar, heated pool and spa, fitness center, library, tiki hut with grilling stations, pickleball and tennis courts, kayak launch, fishing pier, dog play area, and an elevated boardwalk through mangroves and palm-lined grounds. Hidden Bay is conveniently in Osprey just south of Sarasota, near area beaches, shopping and dining, and only minutes from Venice.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Per Nordstrom, Pa (941-228-1080)
244 WOODLAND DR #244, OSPREY, FL 34229
$200,000201 Days on yellowkey MLS ID: A4667419
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1980 Tax: $2,685 (2025)Community: Pine Run IiiCondo
Taxes:$2,685
Remarks: One or more photo(s) has been virtually staged. Turnkey-Furnished & Best Value in Pine Run Now Offered at $200,000 (Recently Reduced $25,000). Move right in and start enjoying the Florida lifestyle with this beautifully updated 2-bedroom, 2-bath condo offering 1,325 square feet of bright, open living. Featuring vaulted ceilings and an airy layout, this residence feels spacious and inviting from the moment you walk in. The kitchen showcases stainless steel appliances, a sleek glass backsplash, and a sunlit breakfast nook perfect for everyday living or entertaining. The primary suite offers direct access to the screened lanai, creating a seamless indoor-outdoor flow with peaceful views of lush, private greenery. Being sold turnkey-furnished, this is a true move-in-ready opportunity just bring your suitcase. Located in the highly sought-after Pine Run community, residents enjoy resort-style amenities including two heated pools, tennis and pickleball courts, a fitness center, clubhouse, and over 20 acres of scenic walking trails. All just minutes from Nokomis Beach, Casey Key, dining, and shopping. Low-maintenance, turnkey living at an unbeatable price, ideal for full-time, seasonal, or investment use.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
14041 BELLAGIO WAY #214, OSPREY, FL 34229
$700,00021 Days on yellowkey MLS ID: A4689731
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1799 Built: 2006Monthly Fee: $1,248 Tax: $6,254 (2025)Community: Villas At Bellagio Harbor VillageSpa: NoCondo
Taxes:$6,254
Remarks: Waterfront Sanctuary-Boater's Paradise at the Osprey Harbor Village- 3 Bedrooms | 2 Bathrooms | Direct Intracoastal Frontage Rare opportunity for direct Intracoastal living at Villas at Osprey Harbor Village (formerly Bellagio Harbor Village). This 3 bedroom, 2 bath residence offers approximately 1,862 sq. ft. of light filled living space with views of the canal, Little Sarasota Bay and Intracoastal Waterway. The open concept design features 9’5” tray ceilings, impact windows and doors, and solid wood cabinetry, granite countertops, kitchen island, and kitchen island bar—ideal for entertaining, anchored by a neutral, airy palette with timeless finishes. The split bedroom layout provides privacy, with a spacious primary suite featuring a spa style bath, separate tub and shower, and direct access to an oversized 270 sq. ft. waterfront balcony from the bedroom. Each window is a curated lens, framing the hues of the Bay and the sculptural silhouettes of architectural lines of Mediterranean inspired Villas. Days here are defined by the rhythmic play of light reflecting across the water and the silent flight of ospreys, eagles, and pelicans—a true haven for the bird watcher seeking a quiet refuge. Whether you are hosting a sunset gathering on your private balcony or entertaining your guests at the community terrace, the club room or embarking on a day of boat excursion to the newly opened Midnight Pass, the lifestyle here is one of effortless coastal elegance. Community amenities include a deep water harbor marina with wet and dry slips, resort pool, clubhouse, fitness center, hot tubs, kayak storage, and launch. Centrally located between Sarasota and Venice, and minutes from Venice, Nokomis, Siesta Key, and Casey Key, Oscar Scherer State Park, Spanish Point, Legacy Trail, and cultural and retail amenities of Sarasota. With new metal roof, exterior and interior paint completed in 2025, this property stands as a resilient sanctuary of enduring value. For the resident who values privacy, prestige, and the restorative power of nature, this is the definitive Osprey address. Schedule your private tour today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Veronica Lee (609-651-0305)
51 MACEWEN DR #5, OSPREY, FL 34229
$300,00015 Days on yellowkey MLS ID: A4689838
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 595 Built: 1990Monthly Fee: $142 Tax: $3,079 (2025)Community: Windsor Lodge At The OaksCondo
Taxes:$3,079
High School: Pine View School
Remarks: Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.
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