One of the most popular communities provided by {{page_data.agentName}}

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

143

# of Listings

3

Avg # of Bedrooms

$533

Avg. $ / Sq.Ft.

$1,275,831

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

143 Properties Found. Page 1 of 10.

Price reduced

Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel relaxed while enjoying the water views and fish jumping. There is nothing to do but move in and enjoy your new home. Taking the boat out is a breeze. Just lower it into the water and you are a short ride out to the intracoastal, the Venice Jetties and Midnight Pass. There are many great waterfront restaurants you can access by boat. If you happen to catch some fish while you are out enjoying the boat, there is a fish cleaning station on the dock. Located between Sarasota and Venice with easy access to I-75. Close to shopping, beaches, restaurants, Oscar Scherer Park and so much more.

OSPREY

120 VILLA DRIVE 120

2 Beds

2 Baths

1,404 Sq.Ft.

$525,000

MLS#: N6138441

Price reduced

This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family and guests, this is a residence that inspire togetherness and embodies the art of waterfront living. Crafted with luxury finishes and modern conveniences, the property is built to exacting coastal standards with dramatic focus on stunning water views. Formal and casual spaces unite elegantly, including the living room with cypress beamed ceilings, overlooking the bay. A deluxe kitchen, wine, butler’s pantry and wet bar provide a canvas for culinary exploration and entertaining elegance. A grand media room for screening films provides the ideal place to unite music and culture. The expansive primary bedroom features a sitting room, lavish bath, dual closets, a breakfast nook and expansive views over the water. Three additional bedroom suites provide privacy, views and spacious accommodations. The fifth bedroom suite is equipped for a home gym, steam room and sauna. The office and library, next to the grand marble staircase, features leaded glass doors, hand crafted, built-in shelving, a coffered ceiling and beautiful views of the Gulf. Additional space for recreation and relaxation has been accomplished to make use of every inch of the estate. Arched hallways and French doors line the living room, open to the dazzling outdoor spaces and stone terraces lead to the infinity pool. Elevator access and garages for six vehicles add ultimate convenience. Enjoy boating from the deep-water dock which features a rare and grandfathered-in covered boat lift. North Casey Key is a haven of exclusivity and serenity, minutes from shopping, world-class golf, tennis and dining.

OSPREY

1216 N CASEY KEY ROAD

5 Beds

6 Baths

8,050 Sq.Ft.

$10,750,000

MLS#: A4643654

Property Type: Commercial Land with Existing Office Building
Property Size: 10 Acres

Discover this exceptional opportunity with over 900 feet of frontage on Tamiami Trail/US41 in Osprey, FL! This is one of the last substantial parcels available in Sarasota County with a Tamiami address. Positioned directly in the path of progress, this 10-acre parcel is ready for development with all entitlements in place.

Property Features:
Existing Office Building: 4,000 SF Freestanding Office Building with water, sewer, and electricity
Development Potential: Density for Assisted Living Facility/Memory Care at 9 units to an acre
Office Space Allowable: Up to 46,000 SF of office space
Prime Location: Directly across from the new Publix and adjacent to massive new developments, including shopping plazas, restaurants, apartments/condos, and single-family homes
Infrastructure: Electric, water, and sewer in place, making the property shovel-ready
Accessibility: Easy access to Tamiami Trail from both ends of the property with simple median cuts at Southbay Drive/Luminary Blvd
Strategic Positioning: Located at the northeast side of the intersection of Luminary Blvd and Tamiami Trail in Osprey, FL

OSPREY

505 LUMINARY BOULEVARD

None Beds

None Baths

4,000 Sq.Ft.

$7,499,000

MLS#: A4616676

Newly Remodeled Gulf-Front Mediterranean Villa on Casey Key
Framed by the pristine natural beauty of North Casey Key, this Spanish Mediterranean beachfront estate is perfectly positioned along one of Florida’s most exclusive barrier islands — an unspoiled, eight-mile stretch of tropical coastline. Just minutes from the cultural and dining destinations of Venice and Sarasota, the residence offers unrivaled privacy, architectural beauty, and Gulf Coast living beyond compare.
Behind a gated entry, the main residence features three bedrooms and three-and-a-half baths, thoughtfully remodeled with no detail spared. Distinctive design elements include wood beams and moldings, Mexican tile and wood floors, brick accents, hand-painted stair tiles, and hurricane-impact windows and doors. Additional enhancements include a new roof, new pool, and updated A/C and pool equipment, ensuring comfort and peace of mind.
The gourmet kitchen showcases custom cabinetry, Wolf appliances, and elegant finishes — ideal for entertaining or everyday living. Expansive windows and sliding glass doors bathe the interiors in natural light and frame breathtaking Gulf views. The master suite serves as a private sanctuary featuring a sitting room, wet bar, soaking tub, dual sinks, walk-in closet, and balcony overlooking the pool. Two en suite guest bedrooms provide comfort and privacy for family or visitors.
A spiral staircase leads to a rooftop deck offering panoramic Gulf and bay vistas. Reflecting the romance of classic Spanish design, the home radiates warmth and character with arched doorways, pecky cypress ceilings, wrought-iron detailing, and timeless brickwork — blending old-world craftsmanship with modern luxury.
The courtyard-style pool area and lush tropical gardens with winding walkways provide a serene setting for outdoor living and entertaining, while the guest quarters above the garage — complete with a full bath — can be used as an art studio, office, or fitness room.
Experience the serenity, seclusion, and sophistication of Casey Key — a rare Gulf Coast haven where architectural elegance meets the natural beauty of Florida’s most celebrated barrier island.

OSPREY

121 N CASEY KEY ROAD

4 Beds

5 Baths

4,096 Sq.Ft.

$7,100,000

MLS#: A4667263

A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless residence blends architectural elegance with waterfront living. Offering private access to the Intracoastal with a 100-foot dock (built in 2019), dual 12,000-pound lifts, water, and electric, this property is an ideal destination for boating enthusiasts. Offered fully furnished upon request. The front elevation is framed by a raised lawn with a stone wall, a paver driveway and manicured landscaping. As you approach the home, the travertine steps lead you to the new custom front door, where dramatic water views of the bay immediately greet you through expansive windows on opposite side of the home, creating a seamless connection to the Gulf and Bay. Inside, the main level is anchored by a breathtaking great room with coffered ceilings, custom millwork, and a wall of windows and doors that open to the terrace, creating an indoor/outdoor living space. A two-sided fireplace adds warmth and ambiance to the great room and the adjacent terrace. The interior showcases a multitude of upgrades, including updated Palecek lighting, and new porcelain tile flooring throughout. The 2020-renovated gourmet kitchen showcases bay views, Cambria Skara Brae quartz countertops, subway tile backsplash, custom white cabinetry and premium stainless-steel appliances. A bar area includes a wine refrigerator and ice maker, while a built-in pantry corridor connects seamlessly to the dining room. The dining area features built-in cabinetry and enjoys stunning bay views from the terrace. The formal living room, with its tranquil blue and cream tones, provides a lovely space to enjoy Gulf views while welcoming guests for dinner. The home offers two spacious primary suites, each with walk-in closets and luxurious en-suite baths, offering serene bay views and access to their private travertine terrace. Two guest suites and an upstairs office also enjoy remarkable water views. The staircase to the upper level reveals an oversized picture window framing the Gulf views. A three-floor elevator provides convenient access to all levels. The ground level features a spacious three-car garage with a dedicated golf cart space. Abundant space is designed to accommodate a variety of uses, and a new glass custom door offers light and access to the backyard and patio. Impact-rated windows and doors, along with a whole-house generator, provide peace of mind. Outside, the resort-style backyard features a refinished pool (with new tile and resurfacing), lush tropical landscaping, an expanded travertine patio and tiered terraces with custom stonework, columns, and stone floors. A rooftop deck offers panoramic views of the Gulf and Bay. Water enthusiasts will appreciate seamless access to the Intracoastal and Gulf, ideal for effortless boating. Additional upgrades include a newly painted roof tile, full exterior and interior repainting (2023), new fencing for added privacy, and two new entry doors (2025), completing the home’s thoughtful transformation. 144 N. Casey Key Road presents a rare opportunity to own a private waterfront estate offering luxury, seclusion and convenient access to Sarasota’s shopping, dining, beaches and parks.

OSPREY

144 N CASEY KEY ROAD

4 Beds

5 Baths

5,397 Sq.Ft.

$5,990,000

MLS#: A4660004

Premier Intracoastal Estate in Osprey
4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterfront Acres
A rare opportunity to own two acres of private waterfront property in Sarasota, 730 Sarabay is a
convergence of residential luxury and unparalleled waterfront living. The two-story home sits at
the end of a long drive behind a gated entrance and tranquil pond. With approximately 100 feet
of bay frontage, the property provides an uncommon level of seclusion. A private dock and boat
lift rated for 15,000 pounds offer instant access to Little Sarasota Bay. With no fixed bridges in
the way, vessels of any height can sail straight through Midnight Pass into the Gulf of Mexico.
Unlike almost every other waterfront property in Sarasota County, this elevated acreage offers higher ground for added peace of mind.
The house features soaring ceilings
and wide-plank oak floors. Its over-sized hurricane-impact glass fills the rooms with light.
Generous living and dining areas, as well as a handsome office and bonus room with water
views, flow in a blend of open-plan and formal spaces, accommodating family gatherings and
grand festivities. The gourmet chef’s kitchen is equipped with solid wood cabinetry, stone
counters, and high-end appliances. The primary suite, conveniently located downstairs, features a
broad view of the bay, vaulted ceiling, spa-like bath, and capacious closets. Reached by
travertine staircase or wood-paneled elevator, the second floor houses three ensuite bedrooms,
one of which serves as a second master. Each offers stunning bay views, a full bath, and ample
closets. A bonus room usable as guest suite, home gym, or playroom, completes the upstairs. The
generously sized travertine patio and bayside lawn are an oasis for outdoor living and gracious
entertaining. The pool features a Baja shelf and integrated spa, and the propane fire pit creates a
cozy spot for cooler evenings. The covered living and dining area commands spectacular views
of the vivid South Florida sunsets. Recent upgrades include two new AC units, a new pool
heater, and a newly painted exterior. Characterized by long lawns and mature palms, the grounds
are a low-maintenance blend of lush beauty and complete privacy. The attached 4-car garage is
proportioned for contemporary vehicles. It includes a built-in workbench with capacious
cabinetry. The free-standing 3-car garage is divided into two and one-car bays, easily customized
for personal use. The two-bay side was an artist’s studio and includes a mini-split and large
laundry sink. The one-bay side overlooks the garden and was previously a home gym. Location
is the most important factor in real estate, and this property delivers. Positioned near A-rated
Pine View School and Oscar Scherer State Park, 730 Sarabay is adjacent to Downtown Sarasota,
convenient to St. Armands, and close to Historic Venice and world-renowned Siesta Key Beach.
This home is a complete waterfront lifestyle, a legacy estate where memories are made and
treasured for generations.

OSPREY

730 SARABAY ROAD

4 Beds

5 Baths

6,308 Sq.Ft.

$5,495,000

MLS#: A4672618

A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the community’s most desirable lots, the residence balances architectural distinction with thoughtful updates that ensure comfort and livability. An oversized circular drive paved in granite tile leads to a stately double-door entrance. Inside, the foyer sets the tone with soaring ceilings, hand-crafted moldings, chandeliers, and a white onyx floor with marble inserts. Spaces include an oversized living room with dual fireplaces, a crystal chandelier, and multiple sets of French doors opening to the lakefront patio. The dining room, anchored by another fireplace and framed by custom casings and built-in shelving, is ideal for grand entertaining. A domed ceiling sitting room with French doors to the patio adds an intimate space for cocktails or conversation, while the custom bar and wine room, with etched glass cabinetry, stone counters, and display shelving, enhances the home’s appeal for gatherings. The kitchen, completely remodeled in 2019, is a showcase of craftsmanship with UltraKraft® cabinetry, custom soffit lighting, Corian countertops, and a center island with breakfast bar. Luxury appliances include a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, microwave, warming drawer, two KitchenAid dishwashers, and a Frigidaire wine fridge. A butler’s pantry provides additional storage, while the sunny breakfast nook overlooks lush gardens. Family and gathering rooms carry the same sense of scale, with dramatic fireplaces, intricate moldings, and detailed ceiling treatments that flow seamlessly for everyday living or large-scale entertaining. The primary suite is a true retreat with a spacious sitting area, custom closets, and a well-appointed bathroom that was newly remodeled in 2025 with spa-inspired finishes. Three guest suites, each with updated full baths (2021 and 2025), provide privacy and comfort. One is a suite with a bathroom near the laundry room, which offers flexibility for live-in staff or extra accommodation. Outdoors, the home embraces its setting with an open pool, expansive deck, and cabana surrounded by manicured hedges and mature landscaping. The views are equally compelling, with mature gardens and community reflecting pond in the front and sweeping lake vistas in the back. Additional highlights include a three-car garage, refinished hardwood floors (2020), and a new Daikin 5-ton AC system installed in 2022. Ownership at The Oaks Club brings an unmatched lifestyle, with two championship golf courses, tennis and pickleball courts, croquet, a fitness center and spa, three on-site restaurants, and a community dock on Little Sarasota Bay. Elegant yet inviting, 101 Osprey Point Drive stands as a rare opportunity to enjoy lakefront living with resort-style amenities in one of Sarasota’s most established private enclaves.

OSPREY

101 OSPREY POINT DRIVE

4 Beds

5 Baths

5,087 Sq.Ft.

$5,000,000

MLS#: A4664424

Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nearly 7000 ft.² of conditioned living space, the residence has undergone an extraordinary transformation – reflecting an investment exceeding $1.5 million – to achieve a standard of craftsmanship seldom encountered in contemporary homes. The grand foyer reimagined with architectural restraint and elegance, opens to a series of impeccably curated, living spaces defined by scale, light and material integrity. The entire home has been freshly repainted, presenting a pristine, harmonious aesthetic that enhances the interplay of color, texture and light throughout. The kitchen rebuilt from its foundation up is a tour de force of design and function-anchored by bespoke ultra-custom cabinetry, expansive, quartz surfaces, and a suite of professional grade Thermador appliances. These include three wall, ovens a speed-cook microwave, an induction cooktop, dual dishwashers, two wine coolers, a U-line beverage refrigerator, and an impressive new side by side Thermador refrigerator and freezer. Every culinary and social experience is elevated by thoughtful details such as Newport Brass fixtures, elegant chandeliers, and an exceptional walk-in pantry that unite beauty and practical design. The primary suite embodies serene granuer, featuring a newly constructed bath with custom cabinetry, a sculptural freestanding tub, and dual shower-all finished in large format, porcelain tile. A remarkable walk-in closet includes a concealed storage and safe room, melding security with sophistication. Two additional bedroom suites have been fully redesigned with its own private bath, while a refined powder room enriches the main entry corridor. Throughout the home, state- of-the-art technology complements the elegant aesthetic, a newly installed security system with outdoor surveillance cameras, ensures peace of mind, while a Sonos sound system, integrates premium audio, seamlessly across living areas for both entertainment and ambience. Additional appointments include new hardwood flooring, freshly refinished and painted garage spaces with an epoxy-coated floor, and a large air-conditioned storage room with supplementary washer, dryer hook ups. The outdoor domain has been equally vitalized, showcasing, a newly remodeled pool, upgraded mechanical systems, and beautifully landscaped grounds that frame the home with natural grace and meticulous attention to detail. Residing within the Oaks Club, homeowners enjoy the exclusivity of one of Sarasota County’s, most distinguished country club communities renowned for its championship golf courses, fine dining, tennis and social amenities. This one-of-a-kind Eagle Watch Lane estate stands as a testament to discerning design, meticulous, stewardship, and enduring architectural grace.

OSPREY

691 EAGLE WATCH LANE

4 Beds

5 Baths

6,705 Sq.Ft.

$3,995,000

MLS#: A4668477

One or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home’s light-filled, open design and thoughtful updates make an immediate impression. The main living spaces flow effortlessly from the chef’s kitchen to expansive entertaining areas and out to the lanai, where golf course views frame the heated pool, spa, and outdoor kitchen.

The first-floor primary suite is a true retreat, featuring high ceilings, multiple closets, and a flexible sitting area that can serve as a nursery, gym, or private office. Upstairs, guests enjoy their own wing complete with a loft, theater, and screened terrace—ideal for relaxing or hosting in style.

A split four-car garage, custom finishes, and generous room throughout reflect the craftsmanship expected in one of Sarasota’s most distinguished country club communities. The Oaks offers 24-hour security, two championship golf courses, an acclaimed racquets program, fitness and wellness facilities, and fine dining—all just minutes from the beaches and top-rated schools.

Experience this home for yourself—take the 3D virtual tour and book your private showing today.

OSPREY

854 MACEWEN DRIVE

4 Beds

4 Baths

9,081 Sq.Ft.

$3,950,000

MLS#: A4668918

If your dream is to create a place where generations can gather, relax, and make lasting memories, this Casey Key estate is ready to welcome you home. Set on 0.68 acres with 131 feet of Sarasota Bay frontage, this 4 bed 4.5 bath retreat offers room to spread out, unwind, and connect indoors and out. Each bedroom opens to the outdoors with bay breezes and water views, while majestic oaks and lush tropical landscaping create a timeless Old Florida setting. Launch your kayak from the backyard, walk your private beach access every morning, and enjoy both sunrises and sunsets from your own waterfront haven. Inside you’ll find a traditional layout with formal living and dining areas, a spacious family room, and a first-floor primary suite. The home has been lovingly cared for and updated with impact windows, new ACs, a metal roof and more. Entertain poolside, dockside, or anywhere in between. No storm damage, no waiting. Just your waterfront life, ready now. Want to tour the dock at sunset? Let’s book your showing.

OSPREY

1042 N CASEY KEY ROAD

4 Beds

4 Baths

4,781 Sq.Ft.

$3,750,000

MLS#: A4674771

Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought-after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers deep water access with no bridges to the bay—a dream for boaters. Nearly every room provides breathtaking views of the water and swaying palms. Constructed with concrete block on both floors and encompassing 6,254 square feet under roof, this home was built for strength, safety, and peace of mind. The main living area is elevated to 18 feet, well above flood levels. Inside, you’ll find an open-concept design with soaring 14-foot coffered ceilings, crown molding, and LED lighting. Expansive sliders lead to a private lanai and wraparound balconies to enjoy serene sunrises and glowing sunsets. The kitchen offers a large granite island, ample counter space, and a gallery window framing the water. Each of the three bedrooms features a private ensuite bathroom. The master suite includes three closets, balcony access, and a spa-like bath with jetted tub, dual vanities, makeup desk, and oversized shower. One secondary bedroom also has balcony access. The first level provides space for cars, toys, and storage with hurricane-impact glass throughout. Closed-cell insulation enhances efficiency, and concrete stairs and elevator shaft add durability. The home sustained no damage or flooding during recent hurricanes. The expansive paved patio overlooks canals frequented by manatees and dolphins.

OSPREY

135 TINA ISLAND DRIVE

3 Beds

4 Baths

2,572 Sq.Ft.

$3,350,000

MLS#: A4665474

Positioned on South Creek just off the Intracoastal Waterway with beautiful views and over 130 FEET of WATERFRONT, this 5-bedroom, 5.5-bath coastal estate offers over 4,261 square feet of refined waterfront living anchored by a truly spectacular backyard oasis. The heated saltwater PebbleTec pool, featuring an impressive 10-FOOT DEPTH, is paired with a separate spa and framed by elegant travertine pavers, with a covered dining area providing a perfect setting for shaded entertaining. An expansive waterfront deck extends beyond the screened lanai for lounging and alfresco dinners overlooking the water. Steps lead to a private dock with a 10,000-pound boat lift and a DEDICATED KAYAK LAUNCH, creating seamless access to the Intracoastal lifestyle. Inside, five generously sized bedrooms each feature ensuite baths and large walk-in closets, with two bedrooms conveniently located on the first floor along with a dedicated office, den, or bonus room. The renovated kitchen is designed for both beauty and function with a Thermador cooktop, Jenn- Airconvection and built-in ovens, a large island, and a passthrough window for effortless outdoor entertaining. The dining area overlooks the pool and includes hurricane-impact sliding doors, a coffee or dry bar with mini-fridge, and additional custom cabinetry for storage. The living room is highlighted by soaring ceilings, transom windows, additional hurricane impact sliding glass doors, and charming shiplap ceiling details, creating a light-filled coastal ambiance. Upstairs, three additional bedrooms and a loft gathering area overlook the living space below, with the true primary suite on the second level along with two waterfront-view bedrooms, all featuring ensuite baths and generous closets, plus a second-floor laundry hookup for added convenience. A spacious three-car garage and elegant U-shaped driveway complete the home. This home has been replumbed and features new lift motors (2025). Located within a gated community offering a basketball court, day dock, playground, and low HOA fees, this property is just 5 miles to Nokomis Beach on Casey Key, 15 miles to downtown Sarasota, 6 miles to the Island of Venice, and 6 miles to Sarasota Memorial Hospital, with Oscar Scherer State Park right nearby for nature lovers and outdoor enthusiasts.

OSPREY

479 SOUTH CREEK DRIVE

5 Beds

5 Baths

4,261 Sq.Ft.

$3,200,000

MLS#: N6141722

CASEY KEY ISLAND OPPORTUNITY – Bring your preferred builder and create the coastal retreat of your dreams on one of Sarasota County’s most treasured barrier islands. Perfectly positioned on the coveted north end of Casey Key, this exceptional property offers over 100 feet of direct Gulf frontage and sweeping, unobstructed sunset views across shimmering turquoise waters. Your blank canvas awaits – whether you already have the vision in mind or just know you desire the island lifestyle, you can shape your own signature beach retreat—collaborating with the architect, designer & builder of your choice. Just moments from the Blackburn Point Bridge, access to and from the island is a breeze while preserving a sense of privacy and exclusivity. Walk, bike or ride to nearby favorites like the Casey Key Fish House & Tiki Bar or Deep Lagoon Restaurant, ideal for casual gatherings with friends and family. Everyday essentials are only minutes away at Publix and the Tamiami Trail. Casey Key offers the best of all worlds with its ideal location between Sarasota and Venice. Just 15 minutes to the south, you’ll find the Downtown Venice historic district with its charming shops & cafés. Head north to Sarasota for fine dining, world-class arts, and vibrant cultural experiences. Don’t miss this rare opportunity to own a slice of paradise, living the island life, surrounded by sun, sand & sea on Casey Key!

OSPREY

141 N CASEY KEY ROAD

None Beds

None Baths

0.39 acres

$3,200,000

MLS#: A4669513

Tucked away in a quiet cul-de-sac on a sprawling double lot beneath majestic oaks, this nearly 5,000 sq ft timeless 2-story residence blends classic elegance with modern luxury. Perfectly positioned on the first hole of one of Sarasota’s most sought-after golf courses, the home showcases soaring 11-ft ceilings, gleaming marble floors, and dazzling crystal chandeliers. A Louis XVI fireplace anchors the dramatic sunken living room, while French doors and expansive windows flood the sunroom with natural light and frame sweeping golf course views. Step outside to three inviting patios—ideal for sunset cocktails, lively gatherings, or peaceful mornings overlooking the greens.
A brick path winds through lush, manicured gardens to the expansive guest house, creating a true family compound that offers exceptional flexibility for hosting guests or multigenerational living.
The nearly 2,000 sq ft guest house features 2 bedrooms, 2 en-suite bathrooms, a generous living room, dining room, outdoor kitchen, and a private laundry room. Overlooking the sparkling pool and spa, this retreat combines privacy with convenience—perfect for extended stays, visiting family, or an in-law suite.
The Oaks Club elevates the lifestyle even further with two 18-hole championship golf courses, fitness center, exceptional dining options, a vibrant calendar of social events, and world-class tennis and pickleball facilities. Ideally located near Casey Key and the powdery white sands of Siesta Key, and just a short drive to Downtown Sarasota’s thriving arts scene and the boutiques of St. Armands Circle. Membership at The Oaks is required.

OSPREY

236 SAINT JAMES PARK

6 Beds

6 Baths

6,246 Sq.Ft.

$2,700,000

MLS#: A4644125

#A4671762

OSPREY

49 OSPREY POINT DRIVE

4 Beds

3 Baths

3,953 Sq.Ft.

$2,595,000

MLS#: A4671762

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