Displaying: For Sale
Location: Osprey
Property Type(s): Single Family
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Osprey - 91 properties found
1486 LANDVIEW LN, OSPREY, FL 34229
$850,000174 Days on yellowkey MLS ID: D6144630
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,488
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: 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)
472 PARK TRACE BLVD, OSPREY, FL 34229
$609,00094 Days on yellowkey MLS ID: A4680326
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2217 Built: 2002Monthly Fee: $58 Tax: $5,925 (2025)Community: Park Trace EstatesSingle Family
Taxes:$5,925
Remarks: Located in the highly desired Park Trace Estates, this beautifully maintained 4-bedroom pool home sits on a premium corner lot and is truly move-in ready. Recent upgrades include a NEW TILE ROOF and IMPACT WINDOWS, offering peace of mind and energy efficiency. The entire house has a LEAFHOME WATER FILTRATION SYSTEM, ensuring clean, high-quality water throughout. The spacious layout is perfect for both everyday living and entertaining, with seamless indoor-outdoor flow to the private SALT WATER POOL. Enjoy mature landscaping on the large corner lot providing added space and privacy, with plenty of room to enjoy the beautiful surroundings. Park Trace Estates has low HOA fees, and is in a prime location close to top-rated schools, shopping, restaurants, Legacy Trail, Oscar Scherer State Park, and Gulf Coast beaches.
Listing is courtesy of: SUNDANCE REAL ESTATE SERVICES (941-780-6710)
Listing Agent: Damon Zuchelli (941-448-5686)
32 BAY AVE, OSPREY, FL 34229
$415,000205 Days on yellowkey MLS ID: N6140978
2 Days Off yellowkey (back on 4/9/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2148 Built: 1962Monthly Fee: $13 Tax: $3,612 (2024)Community: Bay Acres - ResubSingle Family
Taxes:$3,612
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless steel appliances—all completed in 2022. Yard was completely fenced in 2024. With ample square footage, there’s even potential to add a third bedroom, offering flexibility for your needs. All major systems have been upgraded; now this home is waiting for your personal touch. The oversized garage with over 500 SF has sliding doors leading to the backyard and side-yard. Large 15,500 SF of land there is ample space to add a pool. This home has a split bedroom layout and 2 bathrooms (one en-suite; other could be made en-suite). Not located in a high risk flood zone. The Bay Acres community features a private waterfront park on a protected bay with dockage for boats up to 22 feet, a kayak launch, and storage for kayaks and paddleboards. There’s also a shaded picnic area for relaxing or entertaining. Boaters will love the direct access to the water from the 12-slip community boat basin, with slips available by waitlist. For larger vessels, Blackburn Point Park Boat Ramp is just 1.5 miles away. Located just minutes from Casey Key, Siesta Key, and the A+ rated Pine View School, this property is ideal for boaters, beachgoers, and families alike. Nearby attractions include Oscar Scherer State Park, Selby’s Historic Spanish Point, and The Legacy Trail, while Downtown Sarasota and Venice have plenty of shopping, dining, and entertainment options. Bay Acres is a non-deed-restricted neighborhood, giving you the freedom to park your boat, trailer, or RV without the hassle of HOA restrictions. All the hard work has been done—now it’s time to make this your own piece of paradise.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Michelle Richardson (954-683-1002)
1471 SHOAL WAY, OSPREY, FL 34229
$1,499,00070 Days on yellowkey MLS ID: A4683702
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2798 Built: 1985Monthly Fee: $219 Tax: $6,036 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$6,036
Remarks: One or more photo(s) has been virtually staged. This exceptional residence truly checks every box. Designed by a renowned architect for his own family, 1471 Shoal Way is a masterclass in thoughtful design, quality craftsmanship, and effortless livability. Set on one of the largest lots in Southbay (just shy of half an acre) privacy was a guiding principle in the home’s design. Tucked at the end of a quiet cul-de-sac and overlooking an expansive green space, the property feels even more open and serene. No expense has been spared in the home’s extensive upgrades, evident the moment you step inside. Eight-inch wide white oak flooring, custom cabinetry, and high-level quartz countertops create a refined yet inviting aesthetic throughout. A striking, oversized fireplace crafted from natural coral stone anchors the living space and is beautifully framed by solid iron double doors—an architectural feature unique to this home. The layout is equally impressive, offering two distinct living areas, four bedrooms, and three baths, thoughtfully designed to maximize both functionality and flow. The oversized garage includes a workshop area and a climate controlled storage space! With every detail already complete, this home allows you to fully enjoy the idyllic waterfront lifestyle Southbay is known for—whether boating, playing pickleball or tennis, or simply relaxing poolside. Boating in Southbay is made easy with its marina located in the center of the development. Peace of mind comes standard with a metal roof designed to resemble barrel tile, hurricane-rated windows, and a location outside of the flood zone, offering both resilience and long-term value. Pack your bathing suit and bring your boat – live the Florida lifestyle to the fullest. Exclusions: mounted tv/screens, potted plants Pool heater conveys as is
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Lauren Doyle (941-993-9733)
1527 BUOY LN, OSPREY, FL 34229
$1,199,00027 Days on yellowkey MLS ID: A4688266
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2830 Built: 1989Monthly Fee: $204 Tax: $8,555 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$8,555
Middle School: Venice Area Middle
Remarks: Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2026 AC unit, 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage fridge. Large covered outdoor living space overlooking the large lanai with tv, private tanning area, and room to entertain. A split bedroom design, game room with space for billiards table, and separate dining area, and great room surround the private courtyard layout designed to entertain. Ample storage throughout including an air conditioned, secure 12x7 storeroom. Southbay Yacht and Racquet Club offers a clubhouse, tennis, pickleball, basketball, shuffleboard, playground, and low fee, exclusive dockage for residents in the deep water marina. Frequent community activities provide opportunities for an active social atmosphere from cruises to sports.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Matthew Lewis (651-746-4100)
571 PINE RANCH EAST RD, OSPREY, FL 34229
$650,000220 Days on yellowkey MLS ID: A4665938
2 Days Off yellowkey (back on 4/6/2026)
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2746 Built: 1995Monthly Fee: $25 Tax: $6,575 (2024)Community: Bay Oaks Estates Unit 1Spa: NoSingle Family
Taxes:$6,575
Remarks: Under contract-accepting backup offers. One of the largest homes in Bay Oaks Estates, with the second-largest floor plan in the community, this 5-bedroom, 2.5-bath single-story pool retreat delivers the best of indoor-outdoor Florida living with flexible spaces for guests, work, and play. Curb appeal pops with a brick paver circular drive, lush, well-established landscaping highlighted by a mature magnolia and fragrant gardenias, and a covered, columned entry with French double doors and an arched transom. Inside, high ceilings and an abundance of natural light set a welcoming tone. The formal living and dining rooms flow to the heart of the home – a well-appointed kitchen designed for everyday living and entertaining, featuring granite counters, tile backsplash, stainless appliances, a center island with raised breakfast bar, closet pantry, built-in desk and wine rack, recessed & pendant lighting, and a picturesque breakfast nook with wraparound windows. The kitchen opens to the spacious family room with a tray ceiling and mirrored media niche. A pocketing three-panel slider seamlessly extends the living space to the covered lanai and screened pool; additional sliders from the formal living room, the primary suite, and a secondary bedroom maintain the indoor–outdoor connection. Out back, the lanai enjoys a private, tranquil, tree-lined backdrop accented by a mature starfruit tree, overlooking a curved, free-form pool with twin arc fountain jets, a raised sun terrace for lounging, and generous space to relax or gather. A screen door leads to the lawn and a separate pergola patio with power – perfect for morning coffee or an evening grill. From the backyard you have direct access to the Legacy Trail, the popular paved, multi-use path linking Sarasota and Venice, for miles of biking and walking through nature. The private primary retreat offers lanai access, two closets (one walk-in), and a spa-like en-suite bath with a Jacuzzi jetted soaking tub framed by an arched window with plantation shutters, separate walk-in shower with wall body sprays, a long double vanity, and a private water closet. Thoughtful split-bedroom design places three secondary bedrooms and a full bath together in their own wing (one is oversized with lanai access that can flex as a game/media space), while a full 5th bedroom – currently used as an office – sits near the primary suite. An interior laundry room adds storage shelves, cabinets, and a utility sink. Major updates for peace of mind include: replumbed water lines, roof (2015), A/C (2019), new water heater (2024), new pool pump (2024), kitchen appliances (2021), washer and dryer (2023), polycarbonate storm panels, and irrigation. All in a well-kept, low-fee, pet-friendly Osprey community conveniently located just minutes from top-rated schools, including the prestigious Pine View School, and close to the Gulf beaches of world-renowned Siesta Key, Nokomis, and Venice, as well as Oscar Scherer State Park, and a variety of shopping, dining, entertainment, and everyday conveniences; the Gulf Coast lifestyle at its finest. Schedule your private showing today and fall in love with the lifestyle that 571 Pine Ranch East Rd has to offer.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Christiana Kopetzky (941-500-4143)
1795 HIGHLAND RD, OSPREY, FL 34229
$385,00058 Days on yellowkey MLS ID: A4684679
3 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1879 Built: 1999Monthly Fee: $150 Tax: $2,809 (2025)Community: Towns-End ShoresSpa: NoSingle Family
Taxes:$2,809
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile property offers an exceptional opportunity to enjoy the Florida lifestyle while generating income. This home provides both peace of mind and outstanding value in one of Sarasota County’s most sought-after areas. Designed with flexibility in mind, the property features a unique two-level layout that allows you to live upstairs while renting the lower-level in-law suite, currently producing $1,500 per month on a month-to-month lease. The private suite includes its own entrance, bedroom, bathroom, kitchen, and living area, creating an ideal setup for rental income, guests, or multigenerational living. Upstairs, the two bedroom and two bathroom primary residence offers an open and inviting layout filled with natural light. The kitchen features granite countertops, solid wood cabinetry, and a functional layout that flows easily into the living and dining areas. Crown molding, tray ceilings, wood flooring, and thoughtful design elements add character and comfort throughout the home. Recent updates provide valuable peace of mind, including a new air conditioning system and water heater installed in 2024, while the air-conditioned garage adds versatility for storage, hobbies, or a workshop. Plus, NEW ROOF 2026 with 10 year warranty! NO FLOOD ZONE — meaning flood insurance is not required. Outdoor living is just as appealing. Residents enjoy low HOA dues and access to the sunny community pool, along with the rare convenience of a private kayak launch, allowing you to explore nearby waterways and mangroves with ease. The location truly sets this property apart. Bike to the beach, explore nearby Oscar Scherer State Park, or access the Legacy Trail just minutes away for miles of scenic biking and walking. You are also conveniently located near South Bay and the beautiful beaches of Casey Key, along with local dining, shopping, and coastal attractions. Whether you are seeking a primary residence with income potential, a coastal retreat, or an investment property in a prime west-of-the-trail location, this home delivers flexibility, lifestyle, and value all in one. Schedule your private showing today and experience the possibilities this unique property offers.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
434 MACEWEN DR, OSPREY, FL 34229
$1,465,00035 Days on yellowkey MLS ID: A4687368
0 Days Off yellowkey (back on 4/5/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2414 Built: 1997Monthly Fee: $142 Tax: $11,162 (2025)Community: Oaks 2 Ph 3Single Family
Taxes:$11,162
Remarks: Meticulously maintained and updated with care, this 3 bedroom, 3 bath + den/study home in The Oaks Clubside offers beautiful views. A mixture between clean modern lines and cottage chic this house feels cozy. Yet it has an open floor plan, soaring ceilings and every room in the house is light and bright. The formal living room opens to the large lanai and pool with Southern exposure. The view over the lake to the Eagle #6 is simply gorgeous! It is one of the most stunning views in the neighborhood. There is plenty of room to host friends and loved ones. Serve a meal in the formal dining room, have a causal lunch in the kitchen nook or at the breakfast bar, or dine al fresco under the large, covered area overlooking the pool. From the luxurious master suite to the guest bedrooms, this home is beautifully appointed and showcases the finest of details and improvements, including a new roof, impact windows and doors and pretty, updated landscaping. The Oaks, Sarasota’s premier golf and country club, offers two championship golf courses, HAR-TRU tennis courts, pickleball, croquet, and a state-of-the-art WellFit Center.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
437 S SHORE DR, OSPREY, FL 34229
$525,00040 Days on yellowkey MLS ID: N6143587
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1947 Built: 1976Monthly Fee: $10 Tax: $4,187 (2025)Community: Sorrento ShoresSingle Family
Taxes:$4,187
Remarks: Bring your BOAT or RV and store ON YOUR LOT. West of the Trail! Welcome home to Sorrento Shores, nestled perfectly between the vibrant communities of Sarasota and Venice, yet tucked away from the hustle and bustle of city life in the charming town of Osprey. This sought-after neighborhood offers spacious lots, a relaxed atmosphere, and the added bonus of low HOA fees and no CDD to worry about. Discover the possibilities in this home that sits on a generous 19,500 (ALMOST ½ ACRE) square foot lot, providing ample space to stretch out, play, and grow. Step outside and enjoy the expansive, enclosed over-sized lanai and host gatherings all while overlooking your own backyard paradise. Inside, multiple large sliding glass doors effortlessly blend the indoor and outdoor spaces, inviting the sunshine to fill your home. The home features three spacious bedrooms, 2 bathrooms, multiple living spaces, and 2-car attached garage. Recent updates bring peace of mind: NEW ROOF (2025) and HVAC SYSTEM (2025). Also, enjoy the IRRIGATION SYSTEM that runs off a private well to keep your lawn green. This home is also perfectly positioned to enjoy the best local amenities. You’ll find the stunning Oscar Scherer State Park just moments away, offering miles of trails for hiking and birdwatching. The famous Legacy Trail is nearby, ideal for cycling or a leisurely stroll through the scenic landscape. When you're ready to soak up the sun, Nokomis Beach is just a short drive away, perfect for sand, surf, and sunsets. And when it’s time to dine out, you’re surrounded by a variety of waterfront restaurants offering delicious meals with views to match. It’s the ultimate blend of peaceful living and easy access to everything you need for relaxation and adventure.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Dawn Barnett (317-281-8194)
1016 SCHERER WAY, OSPREY, FL 34229
$950,00036 Days on yellowkey MLS ID: A4687161
0 Days Off yellowkey (back on 3/30/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2921 Built: 2003Monthly Fee: $115 Tax: $5,442 (2025)Community: Rivendell Unit 5 The WoodlandsSingle Family
Taxes:$5,442
Remarks: Under contract-accepting backup offers. BEAUTIFUL INSIDE and exceptionally well maintained, this Rivendell home offers the kind of upgrades, efficiency, and outdoor living that are becoming increasingly hard to find. This Luxurious home is situated on a large beautifully landscaped, lake front lot with a Southeast Exposure overlooking Oscar Scherer State park! The interior layout is spacious and functional, featuring tile flooring throughout the main living areas and carpet in the bedrooms for comfort. A dedicated front office connects directly to the primary suite, creating a flexible space ideal for working from home, a sitting room, or even a private retreat. High ceilings and an open flow between the living spaces enhance the overall feel, while the home’s condition reflects true pride of ownership. Step outside and the property truly separates itself. The heated pool has been resurfaced with Pebble Tec and features a solar heating system that was just replaced in 2024, providing year-round enjoyment with energy efficiency. The outdoor space is further enhanced with hurricane roll-down protection, an outdoor stereo system, and a removable baby safety fence—offering both entertainment and peace of mind. Major updates have already been handled, including a BRAND NEW ROOF in 2025 with a transferable 20-year warranty and TWO NEW A/C systems installed in 2025. The home also benefits from an irrigation well, helping maintain the lush landscaping while keeping water costs zero. Total electric costs have remained under $2,400 annually for the entire property, showcasing impressive efficiency for a home of this size. Additional features include a mini-split A/C system in the garage paired with an insulated garage door—perfect for a workshop, gym, or climate-controlled space—as well as a large safe that conveys with the sale. Rivendell residents enjoy a well-rounded lifestyle with low HOA fees that include a heated community pool, playground, and scenic recreational trails—all with no CDD fees. The community offers a rare private path directly to Pine View School and borders Oscar Scherer State Park along with over 200 acres of preserved land, creating a unique blend of convenience and natural surroundings. The home is near both Siesta and Nokomis Beaches, Costco, and loads of shopping and restaurants. Home is situated less than a mile from the Legacy Bike Trail. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. This is a rare opportunity to own a move-in-ready home where the major expenses have already been taken care of—offering a combination of condition, upgrades, and outdoor lifestyle that is hard to match. Book your private showing now to see this property for yourself!
538 DOVE POINTE DR, OSPREY, FL 34229
$1,950,000178 Days on yellowkey MLS ID: A4669491
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4346 Built: 2002Monthly Fee: $133 Tax: $17,098 (2024)Community: Oaks 2 Ph 4-C Pt 3Single Family
Taxes:$17,098
Elementary School: Pine View School
High School: Pine View School
Middle School: Pine View School
Remarks: **ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home showcases timeless architecture with a thoughtful layout and extensive 2023–2025 updates throughout. From its striking curb appeal to its serene outdoor living spaces, every detail has been meticulously curated. Inside, the home offers 4 EN SUITE BEDROOMS, 5.5 BATHS, and a 3-CAR GARAGE that’s been freshly painted and upgraded with a new epoxy floor. Walls of glass fill the home with natural light, complemented by plantation shutters and new motorized window shades throughout. Major updates include a new tile roof (August 2025), two new HVAC units, new LED lighting, and new outlets and light switches across the home. The entire interior and exterior were freshly painted in 2023, giving the home a bright and modern aesthetic. The primary suite is a private retreat, featuring new flooring, a spacious bath, and a bonus office/dressing area for added versatility. A separate office or sitting room, also with new floors, provides ideal space for remote work or quiet relaxation. The three additional bedrooms feature new carpeting, creating a cohesive and comfortable atmosphere. The chef’s kitchen is equipped with new stainless-steel appliances (refrigerator, dishwasher, – all 2025) and flows seamlessly to the main living areas and outdoor entertainment space. There is a new 2025 washer and dryer as well. Step outside to your private Florida oasis — a covered lanai with a full outdoor kitchen and a large motorized Sunbrella shade for comfort and convenience. The property’s two fountains (one new) and professionally graded, elevated landscaping create a lush and tranquil environment perfect for al fresco dining or quiet reflection. 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. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
1042 N CASEY KEY RD, OSPREY, FL 34229
$3,750,000143 Days on yellowkey MLS ID: A4674771
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 4781 Built: 1995 Tax: $18,245 (2025)Community: PalmerSingle Family
Taxes:$18,245
Remarks: One or more photo(s) has been virtually staged. Exceptional Waterfront Estate on North Casey Key. Set along the coveted shores of North Casey Key, this exceptional waterfront residence presents a rare opportunity to experience the very best of coastal Florida living. Nestled within the sought-after Palmer neighborhood and lovingly maintained by the same discerning owners since 1999, the home reflects a true sense of pride, care, and thoughtful stewardship throughout. Positioned on an expansive 0.68-acre parcel with 131 feet of Sarasota Bay frontage and two deeded private beach access points, the property is surrounded by lush tropical landscaping and majestic oaks, creating a serene setting defined by timeless Old Florida charm. From tranquil mornings to vibrant evenings, enjoy both sunrises and sunsets from your own private waterfront retreat. Designed for both everyday comfort and effortless entertaining, the residence offers a traditional yet spacious layout featuring formal living and dining rooms, a generous family room, private office, bonus room, and a serene first-floor primary suite. Three additional guest bedrooms provide ample space for family and visitors, each with access to the outdoors to capture bay breezes and water views. Outdoor living is equally inviting, with a screened-in pool, covered boathouse accommodating vessels over 25 feet, and direct bay access for kayaking or boating. Whether entertaining poolside, gathering dockside, or enjoying quiet moments along the shoreline, the setting is both versatile and inviting. Meticulously updated over time, the home includes a metal roof, two new HVAC systems, PGT impact windows, re-piping, new dock, and much more...offering peace of mind while preserving its character. With no storm damage and move-in-ready condition, the opportunity to begin enjoying the waterfront lifestyle is immediate. Ideally located just 15 miles south of downtown Sarasota and moments from Pine View School, shopping centers, nature parks, and the Legacy Trail, this property offers a unique balance of privacy and accessibility. A truly special home, thoughtfully cared for and ready for its next chapter...where generations can gather, relax, and create lasting memories. Private tours available available with notice.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Brandy Sheldon (941-724-0469)
13 BAYHEAD LN, OSPREY, FL 34229
$850,000396 Days on yellowkey MLS ID: A4645829
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 2310 Built: 2001Monthly Fee: $425 Tax: $3,620 (2024)Community: OaksSingle Family
Taxes:$3,620
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: **IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered driveway, and hurricane-rated patio and bedroom doors. All living areas have wood floors or Italian porcelain tile. The kitchen features a gas stove, Waterworks faucet, quartz countertops, modern stainless appliances, and solid wood cabinetry. The breakfast nook adjacent to the kitchen has aquarium glass windows offering a view of the pool and foliage. The family room glass doors stack behind the wall, providing views of the pool and preserve, and they are hurricane-rated. The owner's suite includes two walk-in closets, a linen closet and space for a sitting area or office. Hurricane-rated glass doors overlook the pool. There is a separate study/office/bedroom with built-in wood cabinetry and space and wiring for a media room. The guest suite has an ensuite bath updated with Quartz counters and a vessel sink. Enjoy the utmost in outdoor living with a stunning, PebbleTec POOL with Travertine deck while there is ample space for a spa or additional seating within the spacious screened lanai. Connections for an outdoor kitchen are also available. A beautiful new pavered driveway adds that special curb appeal. In addition to the metal, roll down hurricane shutters, there is an electric hurricane protective screen spanning the lanai area to protect outdoor furniture. The extra deep two car garage affords additional storage options. A collection of unique bougainvillea and crepe myrtle rounds out the gardens. This lot is located outside the FEMA flood zone Bishops Court in The Oaks Preserve is a 24-hour guard-gated community with walking and biking paths. Additionally, there is a year-round heated community pool nearby. 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. **PLEASE ENJOY VIEWING the 3D VIRTUAL TOUR**
742 HARMS DR, OSPREY, FL 34229
$515,000216 Days on yellowkey MLS ID: A4666421
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1293 Built: 1981 Tax: $5,620 (2024)Community: Harms SubSingle Family
Taxes:$5,620
Remarks: Beautifully renovated and now offered at a newly reduced price, this turnkey property is a fantastic opportunity with motivated sellers. Set on just over half an acre along a private, tree-lined street the home is surrounded by lush tropical landscaping that creates a peaceful and secluded feel. Inside you’ll find a spacious layout with modern finishes and seamless indoor-outdoor living with a heated pool and screened lanai. The home has been fully updated and has a strong history as a successful income-producing rental. Major improvements include a full interior renovation, new roof and pool cage rescreened (2021), pool pump (2022), HVAC (2023), and water heater, well pump, and garage door opener (2024), plus an automated pool cleaner and septic flush (2025). Ideally located between Sarasota and Venice, you’re just minutes from beaches, dining, and shopping. Oscar Scherer State Park sits directly across the street for nature trails and birdwatching, and Legacy Trail (Osprey Junction Trailhead) is only three minutes away, making this a great spot for outdoor enthusiasts. With NO HOA and plenty of space for a boat or RV, this property offers updated comfort, privacy, and flexibility perfect as a full-time home, seasonal retreat, or investment.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Tiffany Stonis (941-204-5239)
448 E MACEWEN DR, OSPREY, FL 34229
$2,100,00037 Days on yellowkey MLS ID: A4687195
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3768 Built: 1998Monthly Fee: $142 Tax: $9,639 (2025)Community: OaksSingle Family
Taxes:$9,639
Remarks: **IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulously-maintained residence features many upgrades and offers breathtaking garden and golf course views in a private, serene setting. Impressive curb appeal and beautifully manicured landscaping welcome you into a beautifully appointed home featuring 4 BEDROOMS plus a STUDY/DEN, 3 FULL and 1 HALF BATHS. Inside, you’ll find high ceilings, elegant crown molding, a cozy fireplace, plantation shutters, custom built-ins, and rich hardwood flooring throughout. The spacious kitchen is designed for both functionality and style, showcasing granite countertops and black stainless KitchenAid appliances. The expansive primary suite is a true retreat, complete with multiple walk-in closets, dual vanities, a soaking tub, and a custom-tiled shower. Enjoy Florida living at its finest on the screened lanai, featuring a heated pool and spa, travertine marble pool deck, and a large covered entertaining area—all overlooking tranquil golf course and garden views for ultimate privacy. Additional highlights include a 3-car garage and thoughtfully designed indoor-outdoor living spaces perfect for entertaining or relaxing. 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. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
180 LOOKOUT POINT DR, OSPREY, FL 34229
$2,249,900170 Days on yellowkey MLS ID: A4672222
Bed: 5 Bath: 3.5 Liv Area Sq Ft: 3236 Built: 1986Monthly Fee: $204 Tax: $8,750 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$8,750
Remarks: One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is an extraordinary residence taken fully down to the studs and reimagined as a like-new, luxury smart home. Set on a .4-acre lot in Flood Zone X (no lender-required flood insurance), this never-lived-in five-bedroom, 3.5 bath, 3,236-square-foot home blends solid block construction with high-end design and cutting-edge technology. No detail was overlooked, including a standing seam metal roof, all new high-velocity impact windows, hurricane-rated garage doors and fully integrated Alexa features throughout. Wide-plank wood floors lead through a thoughtfully designed layout featuring custom built-ins including a kitchen desk, mudroom storage, dining room bar with wine refrigerator and living room shelving with glass doors. The kitchen is a showstopper with two large quartz islands, top-of-the-line Thermador appliances, a microwave drawer, concealed refrigerator, gas range with double ovens and a custom glass-door butler’s pantry. French doors at the entry feature Alexa-controlled electronic glass for your choice of instant privacy or transparent green views, while oversized sliders in the main living area fully retract for seamless indoor-outdoor living. The massive laundry room is a dream with two washers, two dryers, abundant storage and countertop space. Outside, enjoy a stunning new saltwater pool with cage, paver decking, and a state-of-the-art outdoor kitchen including storage and pullout drawer refrigerators, ideal for entertaining. The oversized garage offers excellent storage and the home’s elevation offers added peace of mind. Southbay is one of Sarasota County’s desirable waterfront communities with an updated clubhouse and fitness center overlooking the bay, complete with a ballroom, catering kitchen, meeting room and library. Community amenities also include a geothermal heated pool, children’s pool, tennis, pickleball, shuffleboard, basketball, kayak storage and a seven-acre deep-water marina accommodating boats up to 55 feet. Residents enjoy 20 acres of lush common grounds and five miles of walking trails, plus a vibrant calendar of social events. Near SR 681, with easy access to downtown Sarasota, Venice, beautiful beaches and A-rated schools including Laurel Nokomis, Sarasota Middle, Venice High, Pine View and the European Academy. This is a rare opportunity to own a turnkey, top-tier home in an unmatched boating community.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Katy Mcbrayer (941-400-2406)
854 N CASEY KEY RD, OSPREY, FL 34229
$4,750,00067 Days on yellowkey MLS ID: N6143043
1 Days Off yellowkey (back on 3/26/2026)
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 3462 Built: 1975Community: Acreage & UnrecSingle Family
Taxes:
Tax Year:
Remarks: On the quiet and coveted stretch of North Casey Key, where century-old oaks meet the shoreline, and the land unfolds uninterrupted from Gulf to bay, this extraordinary 1.5-acre estate offers a rare opportunity to steward one of the island’s most incredible homesites. With 180 feet of private Gulf frontage and exceptional depth across to the intercoastal, the property is defined by its scale, privacy, and quiet permanence—offering a setting that feels both expansive and deeply secluded beneath a canopy of mature coastal forest. Here, the rhythm of the water and the natural beauty of the land create an environment that cannot be replicated. The existing improvements include a Gulf-facing main residence, originally constructed in the early 1970s, thoughtfully positioned to capture sweeping views in both directions. The two-bedroom, two-bath home features elevated ceilings, expansive windows, and a sunlit central courtyard designed to bring light and the surrounding landscape into everyday living. A separate guest house, completed in 2002, provides two additional bedrooms and baths, bamboo flooring, Bahama shutters, a versatile bonus room, and an oversized two-car garage—offering flexible accommodations for guests, or interim use while renovating or building. A recently installed private dock completes the property’s rare Gulf-to-Bay lifestyle and provides immediate access to boating and waterfront recreation. While the existing structures offer renovation potential and immediate livability, the true and enduring value lies in the land itself. Homesites of this magnitude—spanning Gulf to bay with this level of frontage, privacy, and natural beauty—are rarely available. Conceptual plans by Potter Homes envision a timeless coastal estate exceeding 6,500 square feet under air, thoughtfully designed to preserve the character of the land while capturing panoramic water views and creating a residence of lasting architectural significance. Whether preserved, renovated, or reimagined entirely, this is more than a homesite—it is the foundation for one of Casey Key’s next great estates, and an opportunity to create something that will endure for generations.
Listing is courtesy of: POTTER TRINITY (239-254-9319)
Listing Agent: Charlie Ruck, Pa (239-464-0191)
700 FAITH AVE, OSPREY, FL 34229
$1,200,000177 Days on yellowkey MLS ID: A4667634
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2474 Built: 1982Community: Trinity AcresSingle Family
Remarks: One or more photo(s) has been virtually staged. Upon passing the gated pillars of the winding driveway you come upon a hidden treasure. 2.5 Acres of beauty tucked away just off Tamiami and Bay in Osprey. This property backs up to the renowned Pine View school grades 2-12. One of the finest schools in the state and country. The peace and tranquility of the outdoor space is highlighted by a resort style swimming pool 40 x10 and attached 25x13 swim shelf with infinity edge, Bubblers, waterfalls, fire balls and 2400Sqft of entertainment area, including a 4 hole putting green, The totally remodeled home has NEW, NEW and NEW, Three A/C’s, Plumbing Water hot and cold, Sewer and Drain lines, Septic, The new septic unit has enough capacity for an additional bathroom, Roof home and Casita, Ceramic tile though out, Hurricane windows and doors 6 French doors opening to backyard pool area, Polyaspartic flooring in garage, Stack stone, Samsung top line kitchen appliances with Bluetooth and Wi-Fi, Soft close custom cabinets, Kitchen, Pantry and bathrooms, The open floor plan is ideal for entertainment with the woodburning fireplace to the twelve-foot ceiling. The layout of the three bedrooms is split with two bedrooms on one side and the primary bedroom on the other side of the house. The casita is the perfect spot for guests, the nanny or grandma. It boasts a kitchenette and ¾ bath, both a screened in attached patio and a deck for you to read or write your novel. There is plenty of room for your horse or cows our to plant a garden and set up a chip and putt golf course. Now Priced below appraised value
Listing is courtesy of: LACEY REALTY INC (941-922-9103)
Listing Agent: Steven Mularky (612-701-4140)
110 PINE AVE, OSPREY, FL 34229
$699,000394 Days on yellowkey MLS ID: A4646339
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2058 Built: 1977Community: Saunders V A ResubSingle Family
Remarks: Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of room for storage. Enjoy sunsets, steps to fishing pier, kayak launch, Spanish Pointe, Oscar Scherer State Park, and Pine View School. No restrictions. Move-in ready enjoying the Florida lifestyle! For outdoor enthusiasts, this location is unbeatable. Launch your kayak or paddleboard from a few steps away into Sarasota Bay, explore Mid night pass, Siesta Beach, nearby Bay Preserve at Osprey and Historic Spanish Point, close to Oscar Scherer State Park, Casey Key, Nokomis Beach. The large backyard offers plenty of space for entertaining, playing, or simply soaking in Florida’s year-round sunshine. Whether you're looking for a family home, a. vacation retreat, or a profitable rental property
Listing Agent: Marisa Marino (941-914-5191)
18 N CASEY KEY RD, OSPREY, FL 34229
$2,000,000196 Days on yellowkey MLS ID: A4669083
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1977 Built: 1973Community: Casey KeySingle Family
Remarks: 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 Agent: Valerie Dall'Acqua (941-445-7295)
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