Displaying: For Sale
Location: Osprey
Property Type(s): Single Family
Price: $1,000,000+
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Osprey - 48 properties found
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
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Middle School: None
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 is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Valerie Dall'Acqua (941-445-7295)
230 OSPREY POINT DR, OSPREY, FL 34229
$2,495,00042 Days on yellowkey MLS ID: A4683382
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 3586 Built: 2014Community: OaksSingle Family
Remarks: Designed by Las Casitas Architects, this Spanish-style residence, featuring 3 bedrooms, 3.5 baths, a den/study with built-in Murphy bed and a 3-car garage, sits on an oversized .59-acre preserve lot with circular drive and courtyard entry. The light-filled, open floorplan features wood and marble flooring, crown molding, tray ceilings, and custom built-ins throughout. The chef’s kitchen is a standout with solid wood cabinetry, granite countertops, a large island with prep sink, counter seating, and premium appliances including Thermador and Bosch. The expansive master suite includes multiple walk-in closets and a luxurious bath with dual vanities and a large custom-tiled shower. Guest bedrooms are generously sized and well-appointed. Enjoy exceptional Florida outdoor living on the spacious screened lanai with heated saltwater pool, outdoor kitchen, and ample covered seating—all overlooking the tranquil North Creek Coastal Preserve. This home is equipped with Control4 automation, Lutron lighting, whole-house water filtration and softener, NEW generator with 500-gallon propane tank, hurricane-impact windows and doors, and two tankless water heaters. A rare combination of quality construction, modern systems, privacy, and natural beauty—this home is truly move-in ready.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
401 WALLS WAY, OSPREY, FL 34229
$1,800,00094 Days on yellowkey MLS ID: A4680312
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 4387 Built: 1990Community: Oaks 2 Ph 1Single Family
Remarks: Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously appointed estate offers a rare opportunity for a premier Sarasota golf course lifestyle. Designed for the discerning enthusiast, the property features panoramic fairway views and western exposure for breathtaking sunsets. The interior is defined by soaring vaulted ceilings, refined crown molding, & finishes throughout. The heart of the home is a curated chef’s kitchen featuring a bespoke butcher block island, professional-grade Viking double ovens, and sleek quartz countertops. High-end functionality includes dual KitchenAid dishwashers and custom cabinetry. The primary living spaces flow seamlessly to a wet bar and wood-burning fireplace, ideal for post-round entertaining. An extraordinary floating staircase of hand-built Hungarian wood leads to a versatile upper level with a private balcony overlooking the course. The primary suite serves as a sanctuary, entered through exquisite hand-carved doors imported from Turkey. This retreat features French doors leading to a private courtyard, custom walk-in closets, and a whirlpool jacuzzi tub. Outdoor living is centered around the pool and an expansive lanai with a fully equipped summer kitchen. Notable infrastructure includes a 3-car garage, three AC units, and clear hurricane shutters. This residence offers an elevated Sarasota lifestyle with immediate proximity to world-class golf and the exclusive amenities of the Oaks community. Please note membership of The Oaks is required.
Listing is courtesy of: ENGEL + VOELKERS SARASOTA (941-388-9800)
Listing Agent: Andrea Stultz (941-929-6529)
20 BAYHEAD LN, OSPREY, FL 34229
$1,575,000116 Days on yellowkey MLS ID: A4674649
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3486 Built: 2017Community: Bishops Court At The Oaks PreserveSingle Family
Remarks: A rare opportunity to own a significantly newer, custom-built residence inside the exclusive The Oaks Club Preserve, where most surrounding homes were built decades earlier. Completed in 2017 and set on a lakefront lot in a non-flood zone, this move-in-ready, hurricane-secure home offers a level of modern construction, privacy, and peace of mind seldom found in this exclusive community. In addition, the home boasts a rare oversized 3-car garage plus attic with ample plywood floor storage, a central vacuum, and a 2026 HVAC system. Wake up to shimmering water views with your morning coffee, open the 16-foot panoramic sliders, and let pleasant breezes flow through, as indoor and outdoor living blend seamlessly. Spend your days relaxing by the heated saltwater pool and spa, cooking in the outdoor kitchen, or hosting sunset gatherings overlooking the water in complete privacy. Inside, the home offers an easy, intuitive flow designed for comfort and simplicity. Soaring 12' ceilings, abundant natural light, and wide sightlines connect the living, dining, and gourmet kitchen spaces. They are not only easy to maintain but perfect for small and large family celebrations and entertainment. A walk-in pantry, lakefront view breakfast nook, and elegant finishes add both beauty and practicality to daily life, and the home provides abundant storage throughout, making it effortless to stay organized and clutter-free. With four bedrooms plus an office and three Carrera-marble-tile bathrooms, the home blends luxury with thoughtful function. Built to today’s strict hurricane standards with full impact windows and storm-secure structural features, it provides exceptional resilience and peace of mind on the Gulf Coast. The Oaks Club Preserve offers 24/7 guarded security and maintenance-free living, along with membership to The Oaks Club, featuring two championship golf courses, 12 Har-Tru tennis courts, pickleball, croquet, a fitness center, community pool, and multiple dining venues. For golfers, every day can begin with early tee times, scenic fairways, and a welcoming social calendar just minutes from home. Close to the #1-rated school in Florida, Pine View, the Legacy Trail, and world-famous Siesta Key Beach, this home delivers modern construction, luxury amenities, and a resort-like lifestyle in one of Sarasota’s premier country clubs. Own a piece of paradise and schedule your private tour today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Lielei Wahlmann (858-883-5876)
530 N MAC EWEN DR, OSPREY, FL 34229
$2,400,00073 Days on yellowkey MLS ID: A4683029
1 Days Off yellowkey (back on 3/20/2026)
Bed: 4 Bath: 5.5 Liv Area Sq Ft: 4346 Built: 2002Community: Oaks 2 Ph 4-C Pt 3Single Family
Remarks: Under contract-accepting backup offers. Located in the prestigious gated community of The Oaks Golf & Country Club in Osprey (Sarasota area), this elegant single-story residence at 530 N Mac Ewen Drive offers resort-style living with championship golf just steps away. Spanning 4,346 square feet under air and 5,837 square feet under roof on an oversized lot, the home features 4 bedrooms, 5 full bathrooms, 1 half bathroom, and a 3-car garage with built-in cabinets and the bonus of a car lift allowing for 4 cars in total. Presented fully furnished and turnkey, this meticulously maintained home is move-in ready and showcases exceptional craftsmanship throughout. Italian granite flows through the interiors, complemented by designer lighting and a whole-house water softener/filtration system. The custom handcrafted kitchen is a chef’s dream, complete with a hidden pantry, soft-close drawers and doors, spice drawers, double oven, and premium Viking Pro appliances. A custom built-in wet bar with ice machine and pull-outs adds convenience for entertaining, while a panoramic electric fireplace anchors the living spaces. A built-in sound system throughout the home and custom closets in every bedroom (including a Therma Sol steam shower in the primary suite) enhance daily comfort. Additional practical luxuries include a bolted-in safe. Step outside to an expansive lanai and backyard oasis featuring a custom-designed pool and hot tub with fire feature, plus a fully equipped outdoor kitchen—perfect for al fresco dining and year-round enjoyment. Industrial-grade landscape lighting (valued at $40K) beautifully illuminates the mature, oversized lot. Residents of The Oaks enjoy 24/7 gated security and world-class amenities including two 18-hole championship golf courses, tennis courts, pickleball, a state-of-the-art fitness center, and vibrant social events. This turnkey luxury home in one of Sarasota County’s most sought-after private communities is an exceptional opportunity for discerning buyers seeking refined coastal Florida living. Roof is 2017 (Tile) and A/C is newer (2023)
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Niall Phelan (941-914-8589)
600 EAGLE WATCH LN, OSPREY, FL 34229
$2,195,000195 Days on yellowkey MLS ID: A4668497
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3681 Built: 1992Community: Oaks 2 Ph 2Single Family
Remarks: One or more photo(s) has been virtually staged. **BRILLIANTLY UPDATED, MOVE-IN READY, GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** offers an Ideal Southern-Exposure and View across the 3rd Fairway of the Interior, HERON GOLF COURSE. Situated on an Oversized 0.71 Acre Lot with Circular Driveway and manicured landscape, this Extensively Renovated Home offers 3 BEDROOMS + STUDY/DEN, 3 FULL BATHS, High Ceilings, Crown Moldings, Gas Fireplace, Engineered Hardwood Flooring, Spacious Kitchen with New QUARTZ Counters and Stainless Steel appliances including premium brands such as SUBZERO and KITCHENAID, 3-Car Garage, Etc. An Expansive Primary Bedroom Suite features multiple walk-in closets, dual vanities, soaking tub and custom-tiled shower. The Expansive screened lanai features a Heated Pool & Spa, Outdoor Kitchen and ample entertaining space in a private and serene setting. NEW FEATURES include ROOF, Hurricane Impact Windows & Doors, Flooring, Countertops, Appliances, Pool Cage, Newly Resurfaced Pool & Spa, newly Pavered driveway and pool deck, etc. 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)
433 E MACEWEN DR, OSPREY, FL 34229
$2,250,000 MLS ID: A4676505
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 4012 Built: 1998Community: OaksSingle Family
Remarks: An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acre lot in the private Oaks Club community. It has golf course and water views and 24 hr gated security. This custom golf course home was built by esteemed builder Arthur Rutenberg. It represents Rutenberg at his very best - stylish elegance, superior craftsmanship designed to accommodate the seamless indoor-outdoor transfer so critical to Florida living. Most prominently the home features 12 foot high ceilings in most rooms, designed to maximize the home's grander, air flow and natural light. The previous owners called it "The House of Light”. The Rutenberg influence abounds in other stunning details starting with the lighted entrance posts, the dramatic circular driveway and the centrally located kitchen that seamlessly opens to a comfortable family/TV room. The home has magnificent coffered ceilings, distinctive crown molding and a gas fire place. Its oversized screened lanai encompasses substantial undercover space for family and guest dining. It is visually highlighted by a 4 foot high tile wall at the head of the pool with a waterfall feature. The kitchen is a cooks delight with new granite counters, stainless steel appliances, including SUBZERO and WOLF. The master bathroom has dual vanities and a large custom tiled shower and soaking tub. The oversized 3 car garage has amble storage capacity, a work table and a refrigerator. Mr. Rutenberg would be pleased to know that this meticulously crafted home has been skillfully updated over the years by all its owners. These improvements include - 1.) hurricane windows and doors (2020), 2.) Roof (2019), 3.) Cage - aluminum structure (2018) 4.) Screened under-cover outdoor grilling area - granite tops, refrigerator, seating for 4, Alfresco grill (20xx). The Oaks has been a member owned private residential golf club for over 40 years. It boosts many accolades, including being the only private residential golf club in the Sarasota/Bradenton/Fort Myers area recognized for high achievement by both Platinum Clubs of America and Distinguished Emerald Clubs of World. It has also been recognized as “The Healthiest Club" and is a certified Audubon Society award recipient. The club has a magnificent 30,000 square foot club house, three exquisite dinning venues, two 18 hole well maintained championship golf courses featuring excellent professional instruction, an outstanding racquets program with 12 har-tru Hydo Grid courts, 4 pickle ball counts, a vibrant croquet program with a regulation sized lawn, a state-of-the-art (newly expanded) wellness/fitness/spa facility, a junior olympic swimming pool, Bocce and a basketball court. Families with children are very welcome here. The Oaks Club’s ideal Sarasota County location places it minutes away from - Sarasota’s vibrant arts and cultural scene and great shopping. It also provides easy access to the expanded Sarasota airport, world class medical care and some of the most beautiful beaches in the world. There is no waitlist for membership.
360 N POINT RD, OSPREY, FL 34229
$1,499,000 MLS ID: A4617671
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2913 Built: 2023Community: Oaks 3 Ph 1Single Family
Remarks: **DON’T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure Gates of the COVETED, OAKS PRESERVE Country Club Neighborhood on Sarasota Bay waters offers superb attention to detail. This Custom-Built residence boasts 3 EN SUITE BEDROOMS + 3 FULL and 1 HALF BATHS and a desirable Open Floorplan concept. A well-equipped Chef’s Kitchen features a large island sitting area, Bosch appliances including 5-burner Gas range, wine storage, etc. while the adjacent great room and dining room are ideal for entertaining and showcase Vaulted and High Ceilings, a cozy fireplace and engineered hardwood floors. The Owner’s Bedroom Suite features a Large Walk-In Closet, Custom Tiled and Glass Enclosed Shower, free-standing soaker Tub, Dual Vanities, bidet and magnificent tile work. Enjoy the utmost Privacy with a Preserve view from the expansive Courtyard and backyard. Circular Driveway with Porte-Cochere + detached 2-car Garage. Hurricane Impact Windows & Doors; Constructed per the latest Hurricane standards. 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. One or more photo(s) has been virtually staged. **ENJOY THE 3D VIRTUAL TOUR**
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