Displaying: For Sale
Location: Osprey
Property Type(s): Single Family
Living Area Square Feet: 1500 to 1999
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Osprey - 9 properties found
353 S SHORE DR, OSPREY, FL 34229
$999,00083 Days on yellowkey MLS ID: A4688006
REDUCED by $26,000 (2.5%) on 06/09/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 1968Monthly Fee: $11 Tax: $3,904 (2025)Community: Sorrento Shores Rep Of 2Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,904
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: Calling all WATER enthusiasts! BOATERS DREAM IN SORRENTO SHORES! Just FOUR houses from the Intracoastal Waterway with NO bridges to the Gulf, this beautifully updated waterfront pool home delivers the lifestyle buyers come to Florida searching for. Welcome to Sorrento Shores — a hidden gem perfectly positioned between Venice Island and Siesta Key, where every day feels like a vacation. Situated on an oversized canal-front lot, this move-in ready 3-bedroom, 2-bath home offers quick deep-water access to the Intracoastal and Gulf beyond. Bring your boat, your paddleboards, your fishing gear, and start living the coastal lifestyle immediately. This home is Offered TURNKEY (minus select personal items), has a Private dock with quick open-water access, a 27x40 screened lanai with resurfaced pool for plenty of lazy pool days, and sits on an Oversized .36-acre lot. No need to store your boat trailer off site, there is ample parking for your boat trailer right on your own property. No CDD fees + voluntary HOA only $130/year And the Big-Ticket items have been taken care of: NEW ROOF 2025, NEW SEPTIC SYSTEM 2024, NEW POOL CAGE 2025 SEWER PIPES RELINED 2023-2024, IMPACT WINDOWS 2018, NEW POOL HEATER 2025, NEW WATER HEATER 2024 Newer A/C 2018 Updated baths + fresh interior finishes 2025 Cruise by boat to Casey Key Fish House, Pops Sunset Grill, Snake Island, Midnight Pass, Venice waterfront restaurants, and the Gulf of Mexico — all from your own backyard. This is not just a home… It’s the waterfront lifestyle buyers dream about!
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Phyllis Coviello (941-408-3265)
4428 CONCHFISH LN, OSPREY, FL 34229
$548,000370 Days on yellowkey MLS ID: A4656074
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1861 Built: 2018Monthly Fee: $147 Tax: $5,936 (2024)Community: Palms/Casey KeySpa: NoSingle Family
Taxes:$5,936
High School: Pine View School
Tax Year: 2024
Remarks: Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a stylish backsplash, a large walk-in pantry, and stainless-steel appliances. The master retreat offers a tranquil area with a spacious bedroom. Plantation shutters and 18x18 tiles complemented by hard floors throughout the entire house. The residence has hurricane shutters, Low-E windows, and a generator hook-up. A large 26x10 covered lanai provides space for relaxing and entertaining. The Palms at Casey Key is a lovely neighborhood with low HOA fees that offers a sense of privacy. Imagine the ease of having your boat just minutes away at the nearby Casey Key Boat Launch, ready whenever you are. They say location is everything, and this home truly delivers on that promise. Ideally situated, it offers immediate access to everyday conveniences: restaurants, grocery stores, and a quick connection to I-75. Dog lovers will appreciate the brand-new dog park nearby, perfect for playtime and socializing. Just under a mile from your front door, the Casey Key Boat Launch and the lively Tiki Bar invite you to unwind and enjoy days by the water. Families will love the close proximity to the prestigious Pine View School, renowned for academic excellence and ranked as the number one high school in Florida, the second-highest elementary school in the US, and the third-highest middle school in the US. Beyond the neighborhood, you'll find easy access to Siesta Key Beach, top-tier golf courses, vibrant cultural attractions, and exciting entertainment options. With low HOA fees and no CDD fees, this home offers the freedom to live your dream Florida lifestyle, without the rising costs of new construction. Move-in ready and like-new, this residence is a perfect blend of character and delightful charm. Store your boat, enjoy the community, and embrace life with ease and comfort. Don’t miss your chance to claim your own piece of paradise!
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Mariana Georgieva (941-809-0416)
408 PARK TRACE BLVD, OSPREY, FL 34229
$595,000110 Days on yellowkey MLS ID: A4685004
2 Days Off yellowkey (back on 6/16/2026)
REDUCED by $20,000 (3.3%) on 06/01/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 2003Monthly Fee: $54 Tax: $4,652 (2025)Community: Park Trace EstatesSingle Family
Taxes:$4,652
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Welcome to your own private oasis in Park Trace Estates, a stunning 3-bedroom, 3-bath single-family home overlooking water with unobstructed views of the Legacy Trail and Oscar Scherer State Park. Located in a desirable community minutes from Pine View School, healthcare, and beaches, this residence is perfectly designed for indoor-outdoor living. The heart of the home is a beautiful central courtyard with a heated saltwater pool with a FastLane system, around which the main living spaces are thoughtfully arranged. An en-suite guest bedroom with private courtyard access provides a secluded retreat perfect for visitors. The open-concept interior flows seamlessly from the kitchen, complete with a signature royal blue Hestan refrigerator, into an inviting living room ideal for entertaining. From there, step out to a screened patio overlooking the water to relax in total comfort. The spacious master suite features dual California Closets, a luxurious remodeled bathroom, and an adjoining room that serves as a private office or reading nook. Throughout the home, plantation shutters provide elegant light control and privacy. The property is finished with a side-entry two-car garage featuring custom California Closets storage and a Tesla charger. Positioned just steps from the pristine Legacy Trail for biking and recreation, this home provides the perfect combination of style and lifestyle. Home is available fully furnished. The home is exceptionally well-maintained, featuring a high-efficiency HVAC system (New AC 2017/Air Handler 2020) with a programmable thermostat, a central vacuum system, and an artistic hidden TV in the living room. Recent kitchen and laundry upgrades include a 2018 washer and dryer alongside newer appliances (2020–2022). The private courtyard is equally impressive, boasting a new pool screen (2022), new pool equipment (2024), and an Endless Pool Fastlane feature for a premium fitness experience. Property is located in Flood Zone X (flood insurance generally not required).
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Jennie Lascelle (941-504-0102)
157 LOOKOUT POINT DR, OSPREY, FL 34229
$875,00026 Days on yellowkey MLS ID: A4694878
0 Days Off yellowkey (back on 6/11/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1859 Built: 1981Monthly Fee: $219 Tax: $4,950 (2025)Community: Southbay Yacht & Racquet ClubSpa: NoSingle Family
Taxes:$4,950
Remarks: Under contract-accepting backup offers. This one is an impressive little gem located in sought after Southbay Yacht & Racquet Club. So many improvements, upgrades and updates all you need to do is bring your furniture and move right in. As we approach the hurricane season, you will enjoy the sense of security provided by the replacement of all windows, sliders and doors with hurricane impact glass. A secluded back yard retreat awaits you with a spacious covered lanai looking onto the updated heated self draining pool and the wooded back yard. Some of the home highlights are: UPDATED KITCHEN AND BATHS, PORCELAIN TILE IN THE MAIN LIVING AREAS, IMPACT WINDOWS ABOUT 11-12 YEARS AGO. The owners have continued with the updates including: NEW METAL ROOF 2023, REPLACED MAIN ELECTRICAL PANEL AND ADDED 220 OUTLET FOR FUTURE GENERATOR. ADDED WHOLE HOUSE AIR PURIFICATION 2022, NEW EPOXY GARAGE FLOOR 2020, A/C AND HEAT PUMP SYSTEM 2018, REPLACED 3 DOORS WITH IMPACT GLASS, REPLACED 3 SLIDING GLASS DOORS WITH IMPACT GLASS 2015, COMPLETE POOL AND LANAI RENOVATION INCLUDING HEAT PUMP AND DECK PAVERS 2017, REPLACED GARAGE DOOR WITH IMPACT RESISTANT DOOR AND VENTS. REPLACED APPLIANCES: MICROWAVE 2025, REFRIGERATOR AND WINE COOLER 2024, RANGE, WASHER, DISHWASHER, 2023, HOT WATER HEATER 2023, REPLACED CARPET WITH CERAMIC TILE 2021 AND CUSTOM PLANTATION SHUTTERS THROUGHOUT THE HOUSE. There are more items I haven’t mentioned but you need to come take a look for yourself. There is a detailed list of improvements available. The Southbay community has much to offer! One of the few neighborhoods with its own exclusive marina. Dock space is only available to residents and is offered at very reasonable rates and can accommodate almost any size boat. Southbay is an active community with many clubs and gatherings at the remodeled clubhouse overlooking the marina. The clubhouse features two kitchens, ballroom, fitness center, card room, even a “livingroom” with grand piano. There’s something for everyone! Pickleball courts, tennis courts, bocce ball, community pool, playground, kayak launch and storage. Southbay is also a golf cart community! The Southbay location is in easy reach of shopping, grocery stores, restaurants, main roads, downtown Sarasota and downtown Venice. Local beaches including Nokomis (5 miles away), Siesta Key (10 miles away), Venice (7 miles) are all within an easy drive. Local restaurants including the famous Casey Key Fish House and Tiki bar are close at hand. Come and see what makes this home and Southbay so special!
Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)
Listing Agent: Pat Williams (941-289-6231)
365 S SHORE DR, OSPREY, FL 34229
$1,349,000173 Days on yellowkey MLS ID: N6142101
REDUCED by $31,000 (2.2%) on 05/02/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1824 Built: 1968 Tax: $7,804 (2025)Community: Sorrento ShoresSingle Family
Taxes:$7,804
Remarks: Wake up to ever-changing INTRACOASTAL VIEWS – SUNSETS dancing across the water, BOATS gliding by, and untouched wildlife. Set on an EXTRA-DEEP WATER FRONT LOT with GULF ACCESS, this exceptional residence offers a rare blend of privacy, sweeping WATERFRONT views, timeless COASTAL DESIGN, and a DOCK WITH A 10,000LB BOAT LIFT that places open water just minutes away. A BOATERS PARADISE, this refined home remains unaffected by flooding AND IN FLOOD ZONE X, unfolds safely toward the water where EXPANSIVE BAY WINDOWS frame uninterrupted scenery. Step out your back door and hop on your boat for effortless days on the water in a premium location. FULLY FURNISHED! Offering 3 BEDROOMS, 2 FULL BATHROOMS, and 1,846 square feet of true Florida living, this home’s PANORAMIC VIEWS flood it with natural light and blur the line between indoors and out. PGT IMPACT WINDOWS, ELECTRONIC SHUTTERS, rich WOOD PANELING, and CROWN MOLDING lend architectural depth and timeless coastal sophistication, creating a home that feels calm, luminous, and deeply connected to its surroundings. The kitchen features QUARTZ countertops, a GRANITE COMPOSITE SINK, and UPGRADED FIXTURES. CEDAR-accented guest bedroom ceilings, CUSTOM built-in closets throughout, and NEW LIGHTING reflect thoughtful stewardship. ADDITIONAL UPGRADES include a new REVERSE OSMOSIS WATER FILTERATION SYSTEM AND WATER HEATER (2023) and AIR DUCTS (2025). Outdoor living is the centerpiece. The PRIVATE DOCK AND OUTDOOR FIRE PIT are natural extensions of the home, inviting morning coffee, sunset cocktails, and manatee sightings. Boat amenities were meticulously maintained with NEW MOTOR CAPACITORS (2023), and BOAT LIFT CABLES AND DOCK LIGHTS (2024). Lush landscaping in the GENEROUS FRONT YARD enhances curb appeal, while mature trees provide tropical PRIVACY, with plenty of room for a POOL. Homes with this DEPTH, PRIVACY, and INTRACOASTAL ACCESS are RARELY available. This is not simply a WATERFRONT HOME – it is a BOATING LIFESTYLE defined by light, movement, and an ever-changing horizon. Just a 2 minute boat ride to the Intracoastal Waterway, 25 minutes to the Gulf of Mexico and 10 minutes to Casey Key Fish House and Tiki Bar! Call for a private tour of this beauty!
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Lisa Asaro (941-725-8626)
18 N CASEY KEY RD, OSPREY, FL 34229
$1,750,000246 Days on yellowkey MLS ID: A4669083
0 Days Off yellowkey (back on 6/1/2026)
REDUCED by $250,000 (12.5%) on 05/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1977 Built: 1973 Tax: $24,015 (2024)Community: Casey KeySingle Family
Taxes:$24,015
Remarks: Under contract-accepting backup offers. Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen, and family room offer inviting spaces to gather, while the split floor plan ensures privacy, ideal for quiet retreats, reading or working from home. Enjoy serene views of the bay and Intracoastal Waterway from the primary suite, a coastal sanctuary. Set on over half an acre, the expansive backyard features a large screened-in pool and lush landscaping, creating your own private tropical paradise by the water. The deeded easement directly across the street leads to a secluded sandy beach, offering endless days of sun, sea, and tranquility. The property remained unaffected by recent storms, a testament to its solid construction and meticulous upkeep. Recent upgrades include mew metal roofs on the home and garage (2020), HVAC system replacement (2020), new water heater (2021), PGT impact-rated windows and doors (2012) and new garage door (2012). Ideally situated for easy access on and off the key, this residence is also close to top-tier shopping, dining, golf, tennis and recreational amenities. With Sarasota and Venice just a short drive away, you’ll enjoy a balance of island living and urban convenience.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Valerie Dall'Acqua (941-445-7295)
524 SARABAY RD, OSPREY, FL 34229
$419,000179 Days on yellowkey MLS ID: A4676179
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1760 Built: 1956 Tax: $1,926 (2025)Community: Bay Acres - ResubSingle Family
Taxes:$1,926
Remarks: 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.
Listing is courtesy of: SUN N SAND REAL ESTATE LLC (574-252-6049)
Listing Agent: Ibett Giannone (574-252-6049)
447 N SHORE DR, OSPREY, FL 34229
$499,000110 Days on yellowkey MLS ID: A4684009
REDUCED by $16,350 (3.2%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1874 Built: 1964 Tax: $4,243 (2025)Community: Sorrento ShoresSingle Family
Taxes:$4,243
Remarks: Classic and cool, this Sorrento Shores beauty blends true Old Florida charm with all the modern updates you actually want, perfectly positioned West of the Trail near the sparkling Intracoastal Waterway. What’s been at the top of your list — move-in ready, a spacious lot, no flood zone, boat/RV parking, optional low HOA, no CDD fees, community marina access, an A+ school district, or quick access to beaches and dining? The good news? You don’t have to choose. This home truly checks every box. Inside and out, everything has been thoughtfully renovated since 2022, including a new roof (2023 w 25yr warranty), septic, central air, impact windows and doors (with the exception of the Florida room), updated electrical panel, irrigation equipment, soffits, water heater, impact garage door, pavers, and beautifully redesigned kitchen and baths. Luxury vinyl plank flooring runs throughout, complemented by fresh paint and abundant natural light. The split floor plan provides privacy, while the open living spaces make everyday living and entertaining effortless. The kitchen is both functional and inviting, featuring shaker cabinetry, quartzite countertops, stainless steel appliances, a generous island, and a charming coffee bar that flows seamlessly into the family room and dinette. One of the standout features is the 336-square-foot air-conditioned sunroom with pocket sliders — incredible flex space for a home office, gym, playroom, or second living area — all overlooking the expansive backyard. The screened lanai and paver patio create easy indoor-outdoor living year-round. The only real decision left? Whether you’ll sip coffee on the welcoming front porch as neighbors pass by or unwind in your private backyard oasis listening to the whispering waves. Sorrento Shores is just minutes from Nokomis Beach (4 miles) and Venice Beach (6.5 miles), close to Oscar Scherer State Park and the Legacy Trail (1.5 miles), near the renowned Pine View School (2.9 miles), with convenient access to I-75, historic City of Venice (5.5 miles) and vibrant downtown Sarasota (12 miles). Here, functional updates, classic charm, location and lifestyle all come together — schedule your showing today!
Listing Agent: Lauren Sisco (904-652-9387)
1486 LANDVIEW LN, OSPREY, FL 34229
$850,000224 Days on yellowkey MLS ID: D6144630
0 Days Off yellowkey (back on 5/3/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1869 Built: 1977Monthly Fee: $204 Tax: $7,488 (2025)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$7,488
Remarks: Under contract-accepting backup offers. Experience refined waterfront living in Southbay, one of the area’s most coveted boating communities. This impeccably maintained three-bedroom pool residence offers a thoughtful, split-bedroom design that balances privacy with seamless flow—ideal for both relaxed everyday living and sophisticated entertaining. A comprehensive renovation in 2017 elevated the home with cohesive flooring throughout, fully redesigned spa-inspired bathrooms with custom vanities, updated ceilings, recessed lighting, and interior shaker doors. The home was also re-piped for water and sewer, offering both modern comfort and long-term peace of mind. The light-filled living room, accented with elegant shiplap detail, opens effortlessly to the lanai, creating a graceful indoor-outdoor connection. Outside, a private retreat awaits with a resurfaced pool, new screen enclosure, and marble pavers. Generous covered space accommodates lounging, dining, and entertaining, while sliding doors from the primary suite, living room, and family room invite the outdoors in and enhance the home’s open, airy ambiance. The primary suite is a serene escape, thoughtfully positioned for privacy and direct access to the lanai. Custom closet systems throughout the home provide elevated functionality, while the epoxy-finished garage with built-in cabinetry delivers a polished, organized finish. Mature tropical landscaping and six-foot pitch apple plantings create a secluded backyard sanctuary, complemented by stately palms that frame the home with unmistakable Florida elegance. Southbay offers a distinguished, resort-style lifestyle with a newly renovated waterfront clubhouse featuring a grand ballroom, catering kitchen, and state-of-the-art fitness center overlooking the marina. Residents enjoy a heated pool, youth pool, tennis and pickleball courts, shuffleboard, bocce, basketball courts, walking trails, and an Intracoastal waterfront park. For boating connoisseurs, the community-owned deep-water marina provides direct Intracoastal access with no fixed bridges to the Gulf. Exclusive, low-fee boat slips accommodate vessels up to 55 feet and are available only to Southbay owners. A vibrant social calendar and golf-cart-friendly streets make it effortless to enjoy community events, nearby boutiques, waterfront dining, and local beaches. Ideally located near Pine View School—Florida’s #1 charter school and one of the nation’s premier gifted programs—this residence presents a rare opportunity to enjoy luxury living within an active, waterfront enclave. A sophisticated coastal retreat where lifestyle, privacy, and boating converge—welcome to Southbay.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Barbara Teyssier (304-671-6691)
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