Displaying: For Sale
Location: Osprey
Property Type(s): Condos
Living Area Square Feet: 1500 to 1999
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Osprey - 8 properties found
4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229
$329,50059 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,781
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
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)
242 HIDDEN BAY DR #603, OSPREY, FL 34229
$550,000105 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)
260 HIDDEN BAY DR #304, OSPREY, FL 34229
$694,00076 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
Elementary School: None
High School: None
Middle School: None
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)
242 HIDDEN BAY DR #602, OSPREY, FL 34229
$700,000101 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
Middle School: Laurel Nokomis Middle
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)
14041 BELLAGIO WAY #214, OSPREY, FL 34229
$700,00020 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)
7303 JESSIE HARBOR DR #7303, OSPREY, FL 34229
$474,900299 Days on yellowkey MLS ID: D6142543
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1883 Built: 1985 Tax: $4,800 (2024)Community: Heron HouseCondo
Taxes:$4,800
Tax Year: 2024
Remarks: 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!
Listing is courtesy of: KW COASTAL LIVING (941-473-7399)
Listing Agent: Toy Coxey (941-662-0010)
250 HIDDEN BAY DR #302, OSPREY, FL 34229
$650,000293 Days on yellowkey MLS ID: A4657042
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1937 Built: 2017Monthly Fee: $1,558 Tax: $5,249 (2024)Community: Hidden BayCondo
Taxes:$5,249
Remarks: ANOTHER PRICE IMPROVEMENT!!!!WHAT A VIEW and the pictures don't do it justice!! SELLER IS OFFERING to prepay three (3) months of HOA dues on behalf of the buyer at closing. FULLY FURNISHED/TURNKEY UNIT! (optional of course) Prepare to be captivated by jaw-dropping sunsets from your oversized, private, screened-in balcony, offering unobstructed vistas across Little Sarasota Bay to the peaceful barrier island of Casey Key. Welcome to Edgewater at Hidden Bay — a gated, 12-acre resort-style community perfectly positioned between the charm of historic Venice and the cultural vibrancy of downtown Sarasota. This impeccably maintained three-bedroom, two-bathroom plus den residence offers panoramic water views and an easy, elegant coastal lifestyle. Step inside to a bright, open-concept layout with a spacious living and dining area — perfect for entertaining or relaxing while soaking in the scenery. The gourmet kitchen is a chef’s dream, featuring stainless steel KitchenAid appliances, granite countertops, 42” real wood cabinetry, counter-height seating, and abundant storage. Coffered ceilings and 5-inch baseboards add refined architectural detail throughout. The expansive primary suite is a tranquil retreat with direct access to the balcony, dual walk-in closets, and a spa-inspired bathroom boasting dual vanities and a glass-enclosed shower. A split bedroom layout offers optimal privacy, while the full-size laundry room includes built-in cabinets and a sink for added convenience. Additional highlights include Kohler plumbing fixtures, hurricane-impact windows and doors, and an abundance of natural light throughout. Offered furnished, this home is move-in ready. Edgewater at Hidden Bay delivers exceptional amenities: a heated resort-style pool and spa, clubhouse with catering kitchen and library, fitness center, tennis and pickleball courts, kayak launch and storage, scenic boardwalk through lush mangroves, and a private fishing pier (currently being rebuilt). Enjoy unmatched access to award-winning beaches (just 6.5 miles to both Siesta Key and Nokomis Beach), Bay Street Park, Legacy Trail, Oscar Scherer State Park, shopping, dining, marinas, golf, and premier medical facilities. This is more than a home — it’s a lifestyle. Schedule your private showing today and discover the very best in waterfront living.
Listing Agent: Merryl Koven (941-526-5913)
14041 BELLAGIO WAY #415, OSPREY, FL 34229
$699,000 MLS ID: TB8470897
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1736 Built: 2006Community: Villas At Bellagio Harbor VillageCondo
Taxes:
Tax Year:
Remarks: A boater's dream. Enjoy waterfront living in this luxury penthouse unit with breathtaking views of the Intracoastal Waterway located in the premier gated community of The Villas at Bellagio. Upon entering the home, you are greeted by the inviting foyer leading down the art gallery-like hallway to the open family room and kitchen area. This three-bedroom, two-bathroom unit has many wonderful features and updates including a recently painted interior, updated light fixtures and ceiling fans, high-end touches such as crown molding, a Sub-Zero refrigerator, solid wood cabinets, gorgeous granite countertops, Bosch dishwasher, storage unit, and two assigned parking spaces in the garage close to the elevator that is only a few steps away from your front door. The owner's suite provides a nice retreat at the end of the day with a garden tub to de-stress and unwind, a separate shower, dual vanities, and a walk-in closet. Watch the spectacular sunsets on your spacious private balcony. The Villas at Bellagio Harbor offers resort-style amenities including a clubhouse, sauna, hot tub, heated swimming pool, fitness center, kayak launch and a connected full-service marina. Wet and dry slips are available for boating enthusiasts. Centrally located to downtown Venice or Sarasota, world-class beaches, fine dining and shopping. Best priced unit in the complex. Walk to Restaurants.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
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