A custom-built Baron estate of timeless elegance, overlooking a tranquil lake from a quiet cul-de-sac within one of the region’s most coveted guard-gated communities. Located in Oaks Bayside, oak-canopied streets, private bay access, and a peaceful setting define everyday living—just steps from the community’s private day dock on Little Sarasota Bay for kayaking and sunset views.
Offering 5,287 square feet of living space, the home features four bedrooms, an office, a study, and 3½ baths, with a floor plan designed for both refined entertaining and comfortable living. Travertine marble and rich hardwood floors extend beneath coffered and tray ceilings, while aquarium windows and impact glass fill the interiors with natural light and frame serene lake views. A gas fireplace anchors the living room, and surround sound enhances the main living areas, all flowing seamlessly to the screened lanai.
The chef’s kitchen is appointed with Wolf and Sub-Zero appliances, an oversized island with bar seating, and a walk-through pantry. A casual dining area adjoins the kitchen, while a separate formal dining room accommodates more formal gatherings. A wet bar with a large-capacity wine refrigerator and custom cabinetry adds a sophisticated entertaining element.
The primary suite offers a private sitting area and a luxurious bath with separate vanities, individual dressing areas, private water closets, and two walk-in closets with custom built-ins. Three additional bedrooms are thoughtfully positioned for family or guests, along with a spacious office, separate study, and a five-seat home theater.
Outdoors, the expansive screened lanai is designed for year-round living, featuring a pool, spa, fountain, covered seating, and a full outdoor kitchen overlooking the lake and lush tropical landscaping. An elegant circular paver drive and a three-car garage with epoxy floors and extensive storage enhance both form and function.
Additional highlights include a whole-home vacuum system, solid wood doors, impact windows, a cedar closet, and abundant storage throughout. Located in Flood Zone X for added peace of mind. The Oaks Country Club offers 2 championship 18 hole golf courses,
Tennis, pickleball, croquet, bocce, and an abundance of social activities to stay engaged in all the club has to offer.
Ideally located near downtown Sarasota, Siesta Key Beach, and renowned cultural destinations, Oaks Bayside offers a rare blend of privacy and convenience. Membership to The Oaks Club is required. A wonderful opportunity to live in one of the finest country clubs in Florida.
Offering 5,287 square feet of living space, the home features four bedrooms, an office, a study, and 3½ baths, with a floor plan designed for both refined entertaining and comfortable living. Travertine marble and rich hardwood floors extend beneath coffered and tray ceilings, while aquarium windows and impact glass fill the interiors with natural light and frame serene lake views. A gas fireplace anchors the living room, and surround sound enhances the main living areas, all flowing seamlessly to the screened lanai.
The chef’s kitchen is appointed with Wolf and Sub-Zero appliances, an oversized island with bar seating, and a walk-through pantry. A casual dining area adjoins the kitchen, while a separate formal dining room accommodates more formal gatherings. A wet bar with a large-capacity wine refrigerator and custom cabinetry adds a sophisticated entertaining element.
The primary suite offers a private sitting area and a luxurious bath with separate vanities, individual dressing areas, private water closets, and two walk-in closets with custom built-ins. Three additional bedrooms are thoughtfully positioned for family or guests, along with a spacious office, separate study, and a five-seat home theater.
Outdoors, the expansive screened lanai is designed for year-round living, featuring a pool, spa, fountain, covered seating, and a full outdoor kitchen overlooking the lake and lush tropical landscaping. An elegant circular paver drive and a three-car garage with epoxy floors and extensive storage enhance both form and function.
Additional highlights include a whole-home vacuum system, solid wood doors, impact windows, a cedar closet, and abundant storage throughout. Located in Flood Zone X for added peace of mind. The Oaks Country Club offers 2 championship 18 hole golf courses,
Tennis, pickleball, croquet, bocce, and an abundance of social activities to stay engaged in all the club has to offer.
Ideally located near downtown Sarasota, Siesta Key Beach, and renowned cultural destinations, Oaks Bayside offers a rare blend of privacy and convenience. Membership to The Oaks Club is required. A wonderful opportunity to live in one of the finest country clubs in Florida.
Property Details
Price:
$2,650,000
MLS #:
A4688291
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
OAKS
Neighborhood:
34229osprey
Listed Date:
May 1, 2026
Finished Sq Ft:
5,287
Total Sq Ft:
6,876
Lot Size:
17,252 sqft / 0.39 acres (approx)
Year Built:
2006
See this Listing
Schools
Elementary School:
Laurel Nokomis Elementary
Middle School:
Sarasota Middle
High School:
Venice Senior High
Interior
Appliances
Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Kitchen Reverse Osmosis System, Refrigerator, Washer, Water Filtration System, Water Purifier, Water Softener, Wine Refrigerator
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Travertine, Hardwood
Heating
Central, Electric
Interior Features
Built-in Features, Ceiling Fan(s), Central Vacuum, Coffered Ceiling(s), Crown Molding, Dry Bar, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
Laundry Features
Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
Levels
One
Exterior
Architectural Style
Custom, Traditional
Association Amenities
Basketball Court, Clubhouse, Elevator(s), Fitness Center, Gated, Golf Course, Pickleball Court(s), Pool, Security, Vehicle Restrictions, Wheelchair Access
Attached Garage YN
1
Community Features
Clubhouse, Deed Restrictions, Fitness Center, Gated Community – Guard, Golf, Pool, Special Community Restrictions, Tennis Court(s)
Construction Materials
Block, Brick, Stucco
Covered Spaces
3
Direction Faces
Southwest
Exterior Features
French Doors, Garden, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Mailbox, Private Yard, Rain Gutters, Sliding Doors, Sprinkler Metered
Garage Spaces
3
Lot Features
Cul-De-Sac, Landscaped, Near Golf Course, Private
Open Parking YN
1
Parking Features
Circular Driveway, Garage Door Opener, Garage Faces Side, Oversized, Parking Pad
Patio And Porch Features
Covered, Deck, Enclosed, Front Porch, Patio, Screened
Roof
Tile
Security Features
Gated Community, Security Gate, Security System, Security System Owned, Smoke Detector(s)
Spa Features
In Ground
View
Water
Waterfront Features
Lake Front
Window Features
Blinds, Shades, Window Treatments
Financial
HOA Fee
$2,950
HOA Fee Frequency
Semi-Annually
HOA Includes
24-Hour Guard, Common Area Taxes, Escrow Reserves Fund, Manager, Private Road, Security
HOA Name
Access Management – Hope Root
HOA Phone
813-607-2220
Tax Year
2025
Taxes
$10,623
Map
Community
- Address449 WEBBS COVE OSPREY FL
- SubdivisionOAKS
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ACREAGE & UNREC
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY OAKS ESTATES UNIT 1
- BAY STREET
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BAYSIDE
- BISHOPS COURT AT OAKS PRESERVE
- BISHOPSCOURT AT THE OAKS PRESERVE
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN HARBOR WATERFRONT VILLAS PHASE 2
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- EDGEWATER/HIDDEN BAY PH II BLD
- HARMS SUB
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PH 4-C PT 3
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OSPREY EXECUTIVE PARK
- OSPREY HARBOR CLUB
- OSPREY PARK 2
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 1 OF BAY STREET
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL THE WOODLANDS
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SORRENTO VILLAS 1
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- THE OAKS BAYSIDE
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS AT OSPREY HARBOR VILLAGE
- VILLAS AT THE OSPREY HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WILLOWBEND PH 1
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WILLOWBEND PHASE 3
- WINDSOR LODGE AT THE OAKS
Market Summary
Current real estate data for Single Family in OSPREY as of May 02, 2026
104
Single Family Listed
144
Avg DOM
460
Avg $ / SqFt
$1,414,355
Avg List Price
Property Summary
- Located in the OAKS subdivision, 449 WEBBS COVE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $2,650,000 and features 4 beds, 4 baths, and has approximately 5,287 square feet of living space, and was originally constructed in 2006. The current price per square foot is $501. The average price per square foot for Single Family listings in OSPREY is $460. The average listing price for Single Family in OSPREY is $1,414,355. To schedule a showing of MLS#a4688291 at 449 WEBBS COVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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Courtesy of MICHAEL SAUNDERS & COMPANY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 449 WEBBS COVE
OSPREY, FL

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