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112 Osprey Point Drive, Osprey
$6,449,000
6 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Under contract-accepting backup offers. A rare combination of timeless grandeur and effortless waterfront living, this bayfront estate in The Oaks Bayside commands approximately 150 feet of Bay frontage across 0.60 acres, with water views framing nearly every principal room. The residence offers 6 bedrooms, 5.5 baths, multiple covered balconies overlooking the Bay, additional ground-level flex space and a side-entry 3-car garage. A circular brick-paver driveway, tropical landscaping and a stately columned entrance create an unforgettable arrival. The dramatic two-story foyer features architectural columns, custom millwork and a wood-clad ceiling accent. European French white oak engineered flooring flows through the main living spaces. The living and family rooms feature soaring ceilings, extensive millwork, statement lighting, carved-stone fireplaces and oversized windows framing expansive water views. An adjoining sitting area features arched windows, a wood-clad ceiling and multiple glass doors opening to the waterfront balcony. The new kitchen is appointed with ceiling-height Shaker cabinetry, champagne-bronze hardware, marble countertops and an oversized waterfall island with seating for five. A GE Monogram appliance suite includes a professional gas range with griddle, refrigerator and dishwasher. A custom range hood, dimensional tile backsplash, apron-front sink and walk-in pantry complete the space. The waterfront dining nook incorporates built-in cabinetry, a stone serving counter and beverage cooler, while the formal dining room features a tray ceiling, paneled walls and columns. A waterfront office with built-in bookshelves, fireplace and balcony access, an updated laundry room and multiple en-suite guest accommodations complete the main level. Upstairs, the landing overlooks the living spaces beneath a crystal chandelier. The primary suite offers separate sleeping and sitting areas, a carved-stone fireplace, wide water views, private balcony access and two walk-in closets with custom storage. Its spa-inspired bath includes dual furniture-style vanities, a freestanding soaking tub beneath a picture window and an oversized frameless shower with marble-look tile, rainfall and handheld fixtures. Additional bedrooms offer en-suite or nearby baths, walk-in closets, abundant natural light and water or tropical views. Multiple covered balconies overlook the newly resurfaced pool, paver terrace, manicured lawn and waterfront. The pool features a 7-foot depth, entry steps, seating or sun-shelf areas, lighting, a self-cleaning system and a new pump. A private walkway through the mangroves leads to a new 5-by-60-foot composite dock completed in 2026, equipped with electric, water and a 6,000-pound boat lift. The property also features a concrete seawall and direct boating access. The lower level provides substantial additional flexibility for recreation, fitness, media or entertaining. Further updates include a newer 2023 tile roof, new HVAC, all-new appliances and flooring, new interior doors and moldings, hurricane protection and exterior lighting. The renowned Oaks Club is one of the area’s premier member-owned clubs, featuring two championship 18-hole golf courses, a full slate of tennis and fitness facilities, and an elegant clubhouse offering fine dining and a vibrant social calendar. Ideally situated in Osprey, the property offers convenient access to Gulf beaches, the Legacy Trail, dining and shopping, with downtown Sarasota and Venice both within easy reach.

112 Osprey Point Drive, Osprey

447 E Macewen Drive, Osprey
$2,750,000
4 Beds ⋅ 5 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Experience refined living in this extraordinary, elegant home. With 3 bedrooms and 4.5 baths it offers expansive lake and golf course views from its premier position along the Heron Course. Designed for both grand entertaining and everyday comfort, the home features generous living spaces, a bright open kitchen overlooking the family room with wood burning fireplace, and a luxurious primary suite with two walk-in closets and a spa style bath. Each guest suite includes its own private bath, ensuring comfort and privacy. Outdoor living shines with a dramatic pool, and spacious covered areas ideal for sunset dining, and beautiful views. Residents enjoy access to The Oaks Club’s renowned amenities, including two championship golf courses, tennis, pickleball, and a vibrant social calendar. Membership is required with homeownership. There is currently no wait list for either Golf or Sports/Social Membership.

447 E Macewen Drive, Osprey

794 Lytham Circle, Osprey
$2,600,000
4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
This 4 bedroom, 4 bath gem will please the most discriminating buyer. You will be immediately intrigued when you pull into the pavered circular driveway. Once you enter though the double front doors, you will feel like you’ve stepped into the pages of a magazine. There is no end to the delightful touches you will find; bathrooms with designer tile, walls sanded to a smooth finish and expertly painted, high-end custom light fixtures throughout and the absolutely stunning master bathroom, to name a few. You will be so taken with the interior that you might think the outside cannot be any better, but wait until you see the gorgeous, expanded lanai with summer kitchen, stone pool deck, and resort-like pool. Beautifully landscaped, the lot appeal of this home is incredible. You truly must see all it has to offer to appreciate how special it is. Imagine living in this gracious home behind the gates of The Oaks Club. The Oaks, Sarasota’s premier golf and country club, offers two championship golf courses, pickleball courts, 12 HAR-TRU tennis courts, tournament croquet court, state of the art WellFit Center and a wide variety of dining, recreational and social options. Membership in The Oaks Club is required with homeownership. There is currently no waiting list for either Golf or Sports/Social membership.

794 Lytham Circle, Osprey

362 Macewen Drive, Osprey
$2,175,000
4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
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. There is currently no waiting list for either Golf or Sports/Social membership

362 Macewen Drive, Osprey