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Osprey

One of the most popular communities provided by Michael Graf

Osprey

About Osprey

Osprey is a tranquil coastal community tucked between Sarasota and Venice, offering a perfect blend of natural beauty and upscale living. Known for its peaceful vibe, top-rated schools, and access to the Intracoastal Waterway, Osprey is ideal for nature lovers and boaters. Residents enjoy quick access to parks like Oscar Scherer State Park, waterfront dining, and nearby beaches. With elegant neighborhoods, quiet streets, and a strong sense of community, Osprey is a hidden gem on Florida’s Gulf Coast.

One of the most popular communities provided by Michael Graf
145
# of Listings
3
Avg # of Bedrooms
$531
Avg. $ / Sq.Ft.
$1,267,951
Med. List Price

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145 Properties Found. Page 2 of 10.

Price reduced
**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. ROOF (2015). 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**
#A4659276

OSPREY

852 MACEWEN DRIVE

3 Beds

3 Baths

4,519 Sq.Ft.

$2,495,000

MLS#: A4659276

Experience Unmatched Luxury in this Meridian Penthouse! Welcome to the epitome of luxury living at Meridian at The Oaks Preserve. This stunning 3 bedroom, 2.5 bath penthouse offers a private 2-car garage and is designed for the discerning buyer who values quality, elegance, and an unparalleled location. From sunrise to dramatic color-drenched sunsets over the Gulf, your days will be filled with the joy of elegant country club living. The moment you enter, you'll be captivated by the classic appointments and meticulous attention to detail. This expansive 3,700 square foot residence features beautiful Travertine marble floors, inlaid wood paneling, and a private elevator that opens directly into your home. The gourmet kitchen is a home chef's dream, boasting panel-ready appliances, maple cabinets, Miele double ovens, a Thermador induction range, and two Fisher Paykel dishwashers. The spacious master suite is a true sanctuary, featuring a luxurious bathroom with a steam shower, Onex counters, a large, jetted tub and his-and-hers closets. The third bedroom is currently set up as an office and has built-in features. With a soundproof media room, Lutron lightening system, customer millwork and a Sub Zero wine storage system, you’d think you couldn’t ask for more! Yet there is! This unit has a TWO CAR PRIVATE GARAGE, retractable screens on the balcony, and motorized hurricane shutters and, for Meridian residents only, your own community pool, spa and fitness center. Offering all this plus everything that being a member of The Oaks, Sarasota’s finest golf and country club, has to offer: two 18-hole championship golf courses, pickleball and 12 HAR TRU tennis courts, a regulation-size croquet lawn, state-of-the-art Wellfit Center, an inspired culinary program, and celebrated social calendar. Membership is required with homeownership.
#A4667964

OSPREY

393 N POINT ROAD 1002

3 Beds

2 Baths

3,738 Sq.Ft.

$2,350,000

MLS#: A4667964

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.
#A4669083

OSPREY

18 N CASEY KEY ROAD

3 Beds

2 Baths

1,977 Sq.Ft.

$2,350,000

MLS#: A4669083

**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**
#A4669491

OSPREY

538 DOVE POINTE DRIVE

4 Beds

5 Baths

4,346 Sq.Ft.

$2,300,000

MLS#: A4669491

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.
#A4672222

OSPREY

180 LOOKOUT POINT DRIVE

5 Beds

3 Baths

3,236 Sq.Ft.

$2,299,900

MLS#: A4672222

One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length. With a six-foot depth at mean low tide, the marina can accommodate 175 boats owned by its residents. In Southbay, the HOA fees are only $612 per quarter and it’s also affordable to keep your boat in a slip that includes water and electric. With the Southbay neighborhood in your backyard and the marina in your front yard, this beautiful, completely renovated waterfront home features three bedrooms, four full baths, a flex-space office and it’s on one of only two waterfront streets in the community. The residence, which has stunning views of water from many of its rooms, boasts a tray ceiling inside the front entry, porcelain plank tile flooring, spacious open rooms, an abundance of impact-rated windows and sliding glass doors, a lovely entertainment kitchen that includes a breakfast area, along with spacious family room and dining room areas. The expansive outdoor pool space, with a newly built custom pool and spa, is framed with a panoramic, clear-span pool cage that features an expansive stone-tiled sundeck, along with ample covered areas for outdoor dining and entertaining. The primary suite offers privacy and boasts a double-door entry to the pool and spa. The primary bath features a deep soaking tub, a frameless glass shower, dual vanity sinks, large-format floor and wall tile, and two walk-in custom closets with organization systems. There are two guest bedrooms with en-suites, one with marina views and the other opens to the pool area, and both feature custom reach-in closets. This home is move-in ready with a three-car garage, brick paver driveway and mature landscaping. The home overlooks the Southbay Yacht & Racquet Club Marina, which features a newly renovated clubhouse that offers grand views of the marina. Inside is a 99-person ballroom with a catering kitchen and dance floor, a community room with a kitchen, piano and entertainment area, a fitness room with aerobic and strength training equipment, a card room, library and a meeting room. The community also has a geothermal-heated pool, a youth pool, covered outdoor patios with furniture, three tennis courts, four pickleball courts, a bocce ball court, two shuffleboard courts, a basketball court, a kayak storage area, a waterfront park, 20 acres of common ground and five miles of meandering sidewalks. The development is golf-cart friendly and the community hosts weekly, monthly and multiple annual events, plus there’s even a Power and Sail Club. You’ll love living in this waterfront home and this special community. Be sure to request a copy of the 50-page digital property catalog, along with viewing the property film.
#A4667293

OSPREY

312 YACHT HARBOR DRIVE

4 Beds

4 Baths

2,572 Sq.Ft.

$2,299,000

MLS#: A4667293

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.
#A4676505

OSPREY

433 E MACEWEN DRIVE

4 Beds

3 Baths

4,012 Sq.Ft.

$2,250,000

MLS#: A4676505

Price reduced
LIVE THE ULTIMATE COASTAL LIFESTYLE on the coveted Casey Key barrier island at this vibrant 3-bed, 3.5-bath waterfront retreat, perfectly positioned along the Intracoastal Waterway with dazzling, front-row views. Designed for unforgettable days on the water, this home features a stunning Aqua-Tech infinity edge heated pool with therapy jet ledge, where you can unwind while watching boats, jet skis, kayaks, and the occasional dolphin glide by. Set on a generous .49-acre lot with lush tropical landscaping, fresh exterior lighting, brand-new shell driveway, and beautifully re-stained cedar siding (2025), the home blends island charm with modern updates. A shared, deeded boat slip offers quick access to the Intracoastal—perfect for sunset cruises, fishing trips, or lunch runs to nearby waterfront restaurants. Step inside to soaring ceilings and sun-filled living spaces anchored by gorgeous engineered hardwood floors. The open-concept great room flows effortlessly to an expansive composite deck designed for entertaining, complete with multiple lounge zones, a grilling area, and panoramic water views that make every gathering feel like a vacation. The chef's kitchen shines with sleek cabinetry, premium stainless appliances, a dramatic stone island, and a glass tile backsplash. A stylish dry bar with leaded glass barn door adds an extra touch of coastal chic. All three bedrooms with their own private ensuites, while the loft provides flexible space for an office, den, or artist’s perch overlooking the main living area. The metal tile roof provides long-term durability, and the optional HOA (only $400) adds neighborhood security without CDD fees. Enjoy peaceful island living with the convenience of Blue Lagoon Restaurant, Mariner Jack Marina, boat and jet ski rentals, fishing spots, and Sarasota’s vibrant dining and cultural venues just minutes away. Private aviation is close by, making travel effortless. THE SELLER IS HIGHLY MOTIVATED AND OPEN TO SERIOUS OFFERS, making this an exceptional opportunity for buyers looking to secure a foothold on Casey Key. Come experience waterfront living at its most energizing and serene way on one of Florida’s most treasured islands. This is Casey Key—where every day feels like a getaway.
#A4665482

OSPREY

140 N CASEY KEY ROAD

3 Beds

3 Baths

2,473 Sq.Ft.

$2,250,000

MLS#: A4665482

New on site 2 days ago
Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located third bath. A three-car garage provides ample space for vehicles and hobbies, complete with a workspace, overhead storage, and cabinets. Ideally positioned as the closest residence to the clubhouse on MacEwen, the home overlooks the 2nd and 3rd holes of the Eagle Course. Manicured landscaping offers complete privacy. Beyond are breathtaking golf course and lake views. Outdoor living features an expansive pool deck, screened lanai, fully updated outdoor kitchen, and a charming open-air patio. The renovated kitchen opens to the family room and includes a breakfast nook with aquarium window offering pool views, plus a formal dining room and breakfast bar for flexible entertaining. This exceptional home combines privacy, comfort, and a prime location for the ultimate country club lifestyle. Membership in The Oaks Club is required. The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership.
#A4676567

OSPREY

362 MACEWEN DRIVE

4 Beds

3 Baths

4,117 Sq.Ft.

$2,249,000

MLS#: A4676567

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.
#A4668497

OSPREY

600 EAGLE WATCH LANE

3 Beds

3 Baths

3,681 Sq.Ft.

$2,195,000

MLS#: A4668497

**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Little Sarasota Bay waters features 3 BEDS plus DEN/OFFICE, 3 FULL BATHS and incredible detail throughout including beautiful crown moldings, volume ceilings, hardwood floors, wainscoting, plantation shutters, LED lighting accents and MORE! NEW ROOF (2020). The CHEF’s KITCHEN boasts Quartzite counters, hardwood cabinetry, NEW Appliances include SUBZERO Refrigerator, WOLF Range and built-in coffee station, etc. The Spacious primary bedroom suite entails a bonus sitting area and multiple walk-in closets while the primary bath offers dual vanities, elegant soaking tub and custom-tiled shower. Enjoy the utmost in Florida living in the expansive, screened Lanai with impressive pavered deck, ample covered sitting area and oversized, Heated, Saltwater, PebbleTec Pool and Spa. This desirable corner lot in Flood Zone “X” with lovely, manicured, lush landscape offers a tranquil and private setting. The nearby Community Day Dock on the Intracoastal Waterway is a cherished amenity of the Oaks-Bayside residents. 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 3 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.
#A4667740

OSPREY

85 SUGAR MILL DRIVE

3 Beds

3 Baths

4,191 Sq.Ft.

$2,150,000

MLS#: A4667740

**BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE RESIDENCE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood. Featuring 4 BEDROOMS (2 En Suite) and 4 FULL BATHS, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown Moldings and refined details throughout is ideal for entertaining both inside and out! The Impressive Kitchen features Silestone Counters, Premium Appliances including SUBZERO and WOLF, Large Island with sitting area, separate dry bar, etc. The Expansive Primary Bedroom Suite entails a Large Walk-In Closet with custom built-ins and spacious bath with dual vanities, quartz counters, seamless glass shower, etc. Stunning Outdoor Entertaining area features an expansive, screened lanai with Heated Pool and Spa, travertine pool deck, and NEW Remote-Controlled Hurricane Screens (2025) surrounded by a tranquil and impressive garden landscape with desirable privacy wall. A Comprehensive List of Improvements is available upon request and includes NEW ROOF (2021), 2 NEW HVAC UNITS w/UV PURIFICATION (2021), NEW HURRICANE IMPACT WINDOWS and DOORS (2021), 500-GAL PROPANE TANK (2022), FRESHLY PAINTED INTERIOR & EXTERIOR, NEW ELECTRICAL SERVICE PANEL, AIR-CONDITIONED GARAGE with NEW, HURRICANE-RATED GARAGE DOORS, and MUCH MORE! NO FLOODING (Flood Zone “X”). The nearby Private Day Dock on Little Sarasota Bay is a valued amenity for Oaks-Bayside residents. 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 and AERIAL VIDEO**
#A4655736

OSPREY

140 SUGAR MILL DRIVE

4 Beds

4 Baths

3,286 Sq.Ft.

$1,970,000

MLS#: A4655736

Price reduced
**STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters… situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This former home of famed architect, Bo MacEwen, who also designed the breathtaking Oaks’ Clubhouse, boasts an impressive 253FT frontage along the highly sought-after Osprey Point Drive in the Bayside neighborhood often regarded as the “Park Avenue” of The Oaks Golf & Country Club. A gorgeous new 4ft x 4ft “Celini Agento Italian” tile accentuates the fresh color scheme throughout this well-appointed home complete with impressive fireplace, 14-inch crown moldings, wainscoting, palladium windows and much more! The nearby, private Dock on the Intracoastal Waterway is a cherished amenity of the Oaks-Bayside residents. The Oaks-Bayside is a truly 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 AERIAL VIDEO**
#A4672439

OSPREY

75 OSPREY POINT DRIVE

4 Beds

4 Baths

4,001 Sq.Ft.

$1,775,000

MLS#: A4672439

Showcase your dining concept at 3983 Destination Drive (Bay Street Village and Towncenter, $1,700,000, 3,871 SF CG, Osprey) – a premier restaurant-ready space in a vibrant, walkable, amenity-rich setting along US-41, steps from the waterfront and thriving residential growth. This turnkey 3,871 SF Restaurant Opportunity is a Two-story, fully built-out space with seating for ~150 guests plus outdoor dining areas. Revenue-Ready Layout – Ground floor offers spacious interior dining room, centralized bar for high-volume service, and outdoor options. Operational Efficiency – Second floor, elevator accessible, includes balcony, additional kitchen workspace, storage, walk-in cooler, and additional dining area with coffee bar ideal for private events, membership type experience or overflow seating. Prime CG Zoning – Flexible commercial use with strong ROI potential. Equipment Included – Restaurant equipment conveys; furniture available and ready for upgrade to match your concept’s brand. Outstanding Exposure – Prominent entrance tower with excellent signage visibility along Route 41. Growth Market – 200+ luxury residential units have just premiered adjacent to the property, which will bring strong foot traffic and revenue potential. Secure a prime restaurant location in a rapidly growing, high-traffic corridor with exceptional visibility along US-41. Surrounded by complementary tenants—including a breakfast and lunch bistro, art galleries, jewelry shops, a spa, a florist, and coworking spaces—this property offers a built-in audience and a rare opportunity for a sophisticated, high-end concept poised for strong long-term returns. Matterport virtual reality tour, equipment inventory, and floor plans available upon request.
#TB8428492

OSPREY

3983 DESTINATION DRIVE 102-202

None Beds

None Baths

3,871 Sq.Ft.

$1,700,000

MLS#: TB8428492

**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious Kitchen with Granite Counters and Stainless Steel appliances, 2-Car Garage w/ Circular Driveway, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets and an Updated Primary Bathroom with dual vanities, soaking tub, custom-tiled shower and private outdoor shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Large 45ft Pebble-Tec Pool & Spa, Outdoor Kitchen space (without appliances) and an abundant covered seating area. Recent UPDATES include Freshly Painted Interior (2024), NEW POOL CAGE (2023), NEW ROOF (2018), HVAC (2018), Pool Pump, 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. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**
#A4621683

OSPREY

909 MACEWEN DRIVE

3 Beds

3 Baths

4,241 Sq.Ft.

$1,695,000

MLS#: A4621683

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