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.
Pending
$2,650,000
449 Webbs Cv, Osprey, FL 34229
4beds
5,287sqft
Single Family Residence
Built in 2006
0.4 Acres Lot
$-- Zestimate®
$501/sqft
$492/mo HOA
What's special
Serene lake viewsAquarium windowsFour bedroomsPrivate bay accessAbundant storage throughoutCovered seatingOak-canopied streets
- 55 days |
- 126 |
- 0 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Rosalie Phillips 941-544-4430,
MICHAEL SAUNDERS & COMPANY 941-966-8000
Source: Stellar MLS,MLS#: A4688291
Originating MLS: Sarasota - Manatee
Originating MLS: Sarasota - Manatee
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Rooms
- Room types: Den/Library/Office, Dining Room, Living Room, Great Room, Utility Room, Media Room, Storage Rooms
Primary bedroom
- Features: Ceiling Fan(s), Walk-In Closet(s)
- Level: First
- Area: 470.4 Square Feet
- Dimensions: 16.8x28
Bedroom 2
- Features: Ceiling Fan(s), Built-in Closet
- Level: First
- Area: 184.15 Square Feet
- Dimensions: 14.5x12.7
Bedroom 3
- Features: Ceiling Fan(s), Built-in Closet
- Level: First
- Area: 171.57 Square Feet
- Dimensions: 13.3x12.9
Bedroom 4
- Features: Ceiling Fan(s), Built-in Closet
- Level: First
- Area: 166.25 Square Feet
- Dimensions: 13.3x12.5
Dinette
- Level: First
- Area: 187.62 Square Feet
- Dimensions: 11.8x15.9
Dining room
- Level: First
- Area: 198.81 Square Feet
- Dimensions: 14.1x14.1
Foyer
- Level: First
- Area: 65.54 Square Feet
- Dimensions: 11.3x5.8
Great room
- Features: Ceiling Fan(s)
- Level: First
- Area: 590.8 Square Feet
- Dimensions: 21.1x28
Kitchen
- Level: First
- Area: 246.4 Square Feet
- Dimensions: 16x15.4
Living room
- Features: Ceiling Fan(s)
- Level: First
- Area: 639.6 Square Feet
- Dimensions: 24.6x26
Media room
- Level: First
- Area: 259 Square Feet
- Dimensions: 14x18.5
Office
- Level: First
- Area: 367.4 Square Feet
- Dimensions: 16.7x22
Heating
- Central, Electric
Cooling
- Central Air
Appliances
- Included: Bar Fridge, 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
- Laundry: Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
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
- Flooring: Carpet, Travertine, Hardwood
- Doors: French Doors, Outdoor Grill, Outdoor Kitchen, Sliding Doors
- Windows: Blinds, Window Treatments
- Has fireplace: Yes
- Fireplace features: Gas, Living Room
Interior area
- Total structure area: 6,876
- Total interior livable area: 5,287 sqft
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Circular Driveway, Garage Door Opener, Garage Faces Side, Oversized, Parking Pad
- Attached garage spaces: 3
- Has uncovered spaces: Yes
Features
- Levels: One
- Stories: 1
- Patio & porch: Covered, Deck, Enclosed, Front Porch, Patio, Screened
- Exterior features: Garden, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Mailbox, Private Yard, Rain Gutters, Sprinkler Metered
- Has private pool: Yes
- Pool features: Gunite, In Ground, Lighting, Outside Bath Access, Screen Enclosure, Tile
- Has spa: Yes
- Spa features: In Ground
- Has view: Yes
- View description: Water, Lake
- Has water view: Yes
- Water view: Water,Lake
- Waterfront features: Lake Front
Lot
- Size: 0.4 Acres
- Features: Cul-De-Sac, Landscaped, Near Golf Course, Private
- Residential vegetation: Mature Landscaping, Trees/Landscaped
Details
- Parcel number: 0142040028
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Custom,Traditional
- Property subtype: Single Family Residence
Materials
- Block, Brick, Stucco
- Foundation: Block, Slab
- Roof: Tile
Condition
- New construction: No
- Year built: 2006
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Connected, Electricity Connected, Propane, Public, Sewer Connected, Sprinkler Well, Street Lights, Underground Utilities, Water Connected
Community & HOA
Community
- Features: Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Special Community Restrictions, Tennis Court(s)
- Security: Gated Community, Security Gate, Security System, Security System Owned, Smoke Detector(s)
- Pet fee: $0 monthly
- Subdivision: OAKS
HOA
- Has HOA: Yes
- Amenities included: Basketball Court, Clubhouse, Elevator(s), Fitness Center, Gated, Golf Course, Pickleball Court(s), Pool, Security, Vehicle Restrictions, Wheelchair Access
- Services included: 24-Hour Guard, Common Area Taxes, Reserve Fund, Manager, Private Road, Security
- HOA fee: $492 monthly
- HOA name: Access Management - Hope Root
- HOA phone: 813-607-2220
Location
- Region: Osprey
Financial & listing details
- Price per square foot: $501/sqft
- Tax assessed value: $1,516,600
- Annual tax amount: $10,623
- Date on market: 5/1/2026
- Cumulative days on market: 32 days
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved, Asphalt
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/19/2026 | Pending sale | $2,650,000$501/sqft |
Source:  Stellar MLS #A4688291 Report a problem | ||
| 5/1/2026 | Listed for sale | $2,650,000+638.2%$501/sqft |
Source: Stellar MLS #A4688291 Report a problem | ||
| 5/30/2002 | Sold | $359,000+28.2%$68/sqft |
Source: Public Record Report a problem | ||
| 5/8/2001 | Sold | $280,000+166.7%$53/sqft |
Source: Public Record Report a problem | ||
| 4/2/1999 | Sold | $105,000$20/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $10,623 +4.1% | $849,531 +2.9% |
| 2024 | $10,208 +3.5% | $825,589 +3% |
| 2023 | $9,866 +2.8% | $801,543 +3% |
| 2022 | $9,594 +0.9% | $778,197 +3% |
| 2021 | $9,509 -0.5% | $755,531 +1.4% |
| 2020 | $9,560 -5.8% | $745,100 -6.7% |
| 2019 | $10,149 | $798,488 +1.9% |
| 2018 | $10,149 +1.9% | $783,600 -1.3% |
| 2017 | $9,958 -6.3% | $793,700 +4.7% |
| 2016 | $10,631 | $758,400 -6.3% |
| 2015 | $10,631 | $809,100 -2.6% |
| 2014 | $10,631 -7.2% | $830,889 |
| 2013 | $11,458 +2.7% | $830,889 +1.7% |
| 2012 | $11,156 +3.6% | $817,000 +1.9% |
| 2011 | $10,772 -17.5% | $801,800 -15.4% |
| 2010 | $13,052 -7.1% | $947,400 -13.9% |
| 2009 | $14,048 | $1,100,399 +0.1% |
| 2008 | $14,048 -3.4% | $1,099,300 -2% |
| 2007 | $14,548 | $1,121,300 +185.7% |
| 2006 | -- | $392,500 +28.1% |
| 2005 | -- | $306,500 +51.2% |
| 2004 | $3,013 +8.4% | $202,700 +12.2% |
| 2003 | $2,779 +16% | $180,700 +13.9% |
| 2002 | $2,396 +12.5% | $158,700 +6.8% |
| 2001 | $2,130 +42.3% | $148,600 +44.3% |
| 2000 | $1,497 | $103,000 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 34229
Nearby schools
GreatSchools rating
- 8/10Laurel Nokomis SchoolGrades: PK-8Distance: 6.6 mi
- 7/10Venice Senior High SchoolGrades: 9-12Distance: 8.7 mi
Schools provided by the listing agent
- Elementary: Laurel Nokomis Elementary
- Middle: Sarasota Middle
- High: Venice Senior High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Sarasota County
- Osprey
- 34229
- 449 Webbs Cv
Nearby cities
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