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Residential: 4 Beds, 6 Baths, In OSPREY.

$ 3,450,000 |  4 bedrooms  | 6 bathrooms | 5178 sq. ft. 

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About this property

Beautifully positioned within Sarasota’s elite country club The Oaks, this sophisticated, multi-level Key West-style home reflects the best in bespoke design. Driving into The Oaks, you’ll instantly feel the privacy and attention to detail that sets this community apart from all others. Meandering roads under a canopy of native Oaks, Palms and Pines wind past exquisite single-family residences. The Oaks Bayside community is adjacent to Historic Spanish Point’s nature preserve and the bayfront, affording the lucky residents of 144 Osprey Point Drive a prime protected location with striking sunset views. Master craftsmenship is evident throughout the home’s three levels, with rich wood floors that connect main living spaces, soaring ceilings with exposed beams and a wraparound balcony that gives every member of the household views of the area’s cherished wildlife. The gourmet kitchen is an epicurean delight with massive center island with bar seating and gas range; abundant cream cabinetry; wine refrigerator and breakfast nook overlooking the mangroves. Perfect for everyday living and entertaining, choose to dine indoors in the formal dining room, or opt for dinner under a blanket of stars on the open-air pool terrace with fully equppied and covered summer kitchen. Retreat to the master suite for the best in self-care with balcony access, marble spa bath and custom walk-in closet. Two additional guest suites allow the owner flexibility to covert one or both into a gym, office or den, and a secondary master suite with full kitchen and laundry boasts it’s own wing. A drive-through motorcourt leads to two oversized garages with ample storage for all your automotive and recreational needs. A few homes down, a boat dock and kayak launch let you explore the area’s mangrove tunnels and waterways. The Oaks is one of the most highly-regarded communities on Florida’s Gulf Coast. Unrivaled amenities include two championship golf courses, a premier tennis program acknowledged by the International Tennis Federation, refined dining experiences, a wellness club that attends to body and spirit, croquet court, active social calendar and more. Owners within The Oaks Bayside are required to have a social or equity membership.

General Information

Other Features
Attic Ventilator
Built in Features
Built-In Oven
Ceiling Fans(s)
Central Vaccum
Coffered Ceiling(s)
Crown Molding
Eating Space In Kitchen
Exhaust Fan
French Doors
Garage Attached
Gas Water Heater
Has Cooling System
Has Fireplace
Has Garage
Has Heating System
Has Pool
High Ceiling(s)
Home Owners Association
Hurricane Shutters
Irrigation System
Kitchen Reverse Osmosis System
Kitchen/Family Room Combo
Open Parking
Range Hood
Solid Wood Cabinets
Stone Counters
Vaulted Ceiling(s)
Walk-In Closet(s)
Water Filtration System
Water Purifier
Water Softener
Window Treatments
Wine Refrigerator
Property Id : 761434
Price: $ 3,450,000
Property Size: 5,178 ft2
Property Lot Size: 1 ft2
Bedrooms: 4
Bathrooms: 6
Accessibility Features: Accessible Approach with Ramp, Accessible Bedroom, Accessible Elevator Installed, Visitor Bathroom, Grip-Accessible Features
Covered Auto Spaces: 4
Architectural Style: Key West
Association Amenities: Clubhouse, Boat Dock, Fitness Center, Gated, Golf Course, Handicap Modified, Maintenance, Playground, Pool, Security, Tennis Court(s), Trail(s), Wheelchair Access
Association Fee: 2100
Association Fee Frequency: Semi-Annually
Association Fee Includes: 24-Hour Guard, Community Pool, Maintenance Grounds, Security
Lot Size Units: Square Feet
Bathrooms Full: 4
Bathrooms Half: 2
Road Frontage Type: Private Road
Road Surface Type: Paved, Asphalt
Community Development District (CDD): no
Building Area Total: 13050
Current Price: 3450000
Community Features: Deed Restrictions, Fishing, Fitness, Gated Community, Golf Carts OK, Golf, Playground, Pool, Tennis Courts, Water Access
Construction Materials: Stucco
Cooling: Central Air, Zoned
Direction Faces: East
Flooring: Carpet, Marble, Hardwood
Foundation Details: Stilt/On Piling
Garage Spaces: 4
High School: Venice Senior High
Elementary School: Laurel Nokomis Elementary
Heating: Central, Electric, Exhaust Fans, Propane, Zoned
Middle School: Laurel Nokomis Middle
Laundry Features: Inside, In Kitchen, Laundry Room, Upper Level
Lease Considered: yes
Levels: Three Or More
Living Area Source: Public Records
Living Area Units: Square Feet
Lot Features: Conservation Area, Flood Insurance Required, FloodZone, In County, Near Golf Course
Lot Size Square Feet: 23163
Status: Active
Ownership: Fee Simple
Parking Features: Circular Driveway, Covered, Driveway, Garage Door Opener, Garage Faces Rear, Ground Level, Portico, Under Building
Patio And Porch Features: Covered, Deck, Front Porch, Porch, Rear Porch, Screened, Side Porch, Wrap Around
Pool Features: Auto Cleaner, Deck, Heated, In Ground, Lighting, Pool Sweep, Tile
Roof: Concrete, Tile
Additional Lease Restrictions: Lease restrictions
Additional Rooms: Family Room, Formal Dining Room Separate, Inside Utility
Association Approval Required: no
Association Fee Requirement: Required
Building Elevator: yes

On The Map

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Active Life

Active Lifestyles
(4.36 miles)Active Lifestyles
Active Door & Window
(34.16 miles)Active Door & Window
Pup Active
(41.3 miles)Pup Active

Arts & Entertainment

(3.57 miles)Nontando
Coco Nails Spa
(1.27 miles)Coco Nails Spa
Chic Art & accents
(2.71 miles)Chic Art & accents


Chabad Kaplan Preschool
(2.17 miles)Chabad Kaplan Preschool
Faith Early Learning Center
(2.07 miles)Faith Early Learning Center
(2.37 miles)SwimSRQ

Financial Services


Screaming Goat Taqueria
(3.54 miles)Screaming Goat Taqueria
Big Water Fish Market
(3.39 miles)Big Water Fish Market
Taco Jalisco
(3.35 miles)Taco Jalisco

Health & Medical

Dees Integrative Health
(0.82 miles)Dees Integrative Health
Sarasota Eastern Massage & Spa
(0.89 miles)Sarasota Eastern Massage & Spa
Healing Hands Chiropractic & Massage
(0.96 miles)Healing Hands Chiropractic & Massage

Local Flavor

Local Services


The Beach Club
(6.04 miles)The Beach Club
Cruisin' Tikis Sarasota
(4.78 miles)Cruisin' Tikis Sarasota
Tommy Knockers Gulf Gate
(3.66 miles)Tommy Knockers Gulf Gate


A Natural Pet Pantry
(2.26 miles)A Natural Pet Pantry
Bayside Pet Resort of Osprey
(1.94 miles)Bayside Pet Resort of Osprey
Nelson D S DVM
(1.69 miles)Nelson D S DVM

Religious Organizations


Ophelia's on the Bay
(0.97 miles)Ophelia's on the Bay
Big Water Fish Market
(3.39 miles)Big Water Fish Market
The Point
(1.13 miles)The Point


Sarasota Square
(1.64 miles)Sarasota Square
Floribbean Flo's Tropical Bakery
(2.3 miles)Floribbean Flo's Tropical Bakery
Beach Bazaar
(6 miles)Beach Bazaar

John Keller III

John Keller III

Skype: jackkellerinc
Phone: 727-586-1497
Mobile: 727-418-1694
Email: [email protected]

Contact Me

Schedule a showing?
You can reply to private messages from "Inbox" page in your user account.

John Keller III


Contact Me

Schedule a showing?
Call 727-418-1694 WhatsApp
You can reply to private messages from "Inbox" page in your user account.
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John Keller III