101 Osprey Point Dr $5M Lakefront Luxury Home, Stunning Osprey Real Estate Opportunity

Date of Publishing: September 18, 2025

At the heart of Sarasota County’s prestigious gated enclave, The Oaks Bayside, a rare lakefront jewel has emerged on the market. Priced at $5 million, the single-level residence at 101 Osprey Point Dr blends timeless architecture with thoughtful modern updates. Designed by renowned architect Bo MacEwen in 1985 and fully refreshed over the last five years, this home in Osprey for sale exemplifies the best of Osprey real estate – gracious interiors, private resort amenities, and a setting of unrivaled natural beauty.

Elegant $5M Osprey Florida lakefront home featuring infinity pool spacious patio and stunning Gulf Coast sunset views

Grand Arrival and Architectural Distinction

Approached by an oversized circular drive paved in granite tile, the home in Osprey for sale makes a striking first impression. A stately double-door entrance opens to a soaring foyer where hand-crafted moldings, crystal chandeliers, and a white onyx floor with marble inserts announce the level of craftsmanship within. From the moment guests step inside, they are surrounded by airy ceilings and meticulously finished details that capture the elegance of classic Florida estates while introducing contemporary comfort.

The oversized living room provides a stunning centerpiece. Dual wood-burning fireplaces framed by intricate crown molding create a warm gathering space, while multiple French doors lead to a sweeping lakefront patio. Across the hall, the dining room continues the sense of grandeur, anchored by another fireplace and framed by custom built-ins that invite both formal entertaining and intimate dinners. A domed-ceiling sitting room offers a refined corner for cocktails or quiet conversation, and a custom bar and wine room – complete with etched-glass cabinetry and stone counters – enhances the home’s capacity for entertaining on any scale.

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A Culinary Haven and Family Comfort

The kitchen, completely remodeled in 2019, reveals how modern updates elevate this classic design. UltraKraft cabinetry, Corian countertops, and a center island with breakfast bar combine beauty with functionality. Luxury appliances include a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, microwave, warming drawer, two KitchenAid dishwashers, and a Frigidaire wine fridge. A sunny breakfast nook overlooks manicured gardens, while a discreet butler’s pantry provides abundant storage.

Adjoining family and gathering rooms carry the same sense of scale and warmth. Dramatic fireplaces, detailed ceiling treatments, and hand-selected finishes flow seamlessly to create spaces equally suited to everyday living or large celebrations. “This Osprey home for sale represents the rare marriage of architectural pedigree and modern livability,” listing agent Joel Schemmel told Luxury Houses Magazine, emphasizing the extensive upgrades that complement MacEwen’s original vision.

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Private Retreats and Spa-Inspired Baths

The primary suite functions as a true retreat. A spacious sitting area invites relaxation, while custom closets and a newly remodeled spa bath completed in 2025 introduce serene finishes of stone and glass. Three additional guest suites, each with private baths updated in 2021 and 2025, provide privacy for visitors. One suite, located near the laundry room, offers flexibility for live-in staff or extended-stay guests.

“The owners poured their hearts into every detail, from the spa-like primary bath to the custom wine room,” Schemmel shared with Luxury Houses, noting that the sellers – longtime residents who prefer to remain private – worked closely with designers to preserve the home’s character while elevating every surface.

Outdoor Living and Resort Amenities

Outdoors, nearly an acre of manicured grounds unfolds across two of the community’s most desirable lots, granting 150 feet of direct lakefront. An open pool with expansive deck and cabana invites year-round recreation. Mature gardens, manicured hedges, and the community’s reflecting pond provide tranquil views from every vantage. The home’s three-car garage, refinished hardwood floors completed in 2020, and a Daikin five-ton AC system installed in 2022 further ensure long-term comfort.

Ownership in The Oaks Club adds another layer of exclusivity. Residents enjoy two championship golf courses, tennis and pickleball courts, croquet lawns, a state-of-the-art fitness center and spa, and three on-site restaurants. A community dock on Little Sarasota Bay offers boating access, while the gated, 24-hour-guarded entry underscores privacy and security.

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Location and Lifestyle

Beyond the gates, Osprey offers a lifestyle that blends natural beauty with sophisticated convenience. Nearby Casey Key and Siesta Key beaches provide world-famous white sand, while downtown Sarasota’s art galleries, fine dining, and cultural venues are just fifteen minutes away. Upscale shopping at St. Armands Circle and a vibrant culinary scene – from seafood restaurants to farm-to-table bistros – enhance the area’s appeal. Easy access to U.S. 41 and I-75 places residents within convenient reach of the wider Gulf Coast and Sarasota-Bradenton International Airport.

As Luxury Houses Magazine learned through public records, 101 Osprey Point Dr has a compelling history. The Osprey real estate sold in late 2018 for $1.3 million before extensive renovations began. It re-entered the market in March 2025 at $5.3 million, was temporarily withdrawn in June, and now debuts again at $5 million with even more enhancements. “The combination of heritage architecture and modern upgrades makes this a rare investment opportunity,” Schemmel told Luxury Houses, adding that serious buyers recognize the scarcity of such lakefront properties within The Oaks.

A Legacy Property in Osprey Real Estate

From dual fireplaces and intricate moldings to its unmatched location on a nearly one-acre double lot, this Osprey home for sale stands as a legacy property. The careful preservation of Bo MacEwen’s architectural intent, coupled with a comprehensive program of updates, ensures that 101 Osprey Point Dr will remain timeless for generations. “Homes of this caliber, especially on prime lakefront parcels, simply do not come to market often,” the agent affirmed to Luxury Houses.

For discerning buyers seeking privacy, elegance, and access to resort-style amenities, the opportunity is exceptional. Those interested can explore the full gallery and schedule a private tour through Zillow. Additional details and direct inquiries may be made via the Douglas Elliman listing page.

With its rare blend of classic design and contemporary luxury, 101 Osprey Point Dr epitomizes the highest standard of Osprey real estate. From its grand arrival to the serene lakefront setting, every element of this property speaks to a life well lived on Florida’s Gulf Coast.

For inquiries or to schedule a private showing, please contact:

Joel Schemmel
941-587-4894
DOUGLAS ELLIMAN

* This property might not for sale at the moment you read this post; please check property status at the above Zillow or Agent website links*