449 WEBBS COVE, Osprey, FL 34229
SOLD
AUG 27, 2026

$2,479,900

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 5,287 sqft (on 0.40 acres)

449 WEBBS COVE, Osprey, FL 34229

Est. Refi. Payment $15,110/mo*
Refinance Your Home
Currently Off Market - Sold Aug 27, 2026 for $2,470,000 (7% below list price)

Home Value

Trulia Estimate
$2.48M
Since last month
$0 (0%)
Since last year
Increased$778K (+46.2%)
Since last sale
Decreased$8K (-0.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +99% in the last 10 years
MonthEstimated value
2026
August 2026$2.46M
July 2026$2.46M
June 2026$2.48M
May 2026$2.48M
April 2026$1.71M
March 2026$1.81M
February 2026$1.81M
January 2026$1.77M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
137 OSPREY POINT DRIVE, Osprey, FL
0.14
Single-Family Home
$1,285,000
04/08/26
4
3
3,303
76 OSPREY POINT DRIVE, Osprey, FL
0.17
Single-Family Home
$1,450,000
06/15/26
3
4.5
4,364
370 SUGAR MILL DRIVE, Osprey, FL
0.27
Single-Family Home
$2,189,000
02/09/26
5
5.5
4,783
112 OSPREY POINT DRIVE, Osprey, FL
0.19
Single-Family Home
$2,315,000
10/30/25
4
5.5
8,635
325 OSPREY POINT DRIVE, Osprey, FL
0.19
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
67 SUGAR MILL DRIVE, Osprey, FL
0.44
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
340 OSPREY POINT DR, Osprey, FL
0.24
Single-Family Home
$1,900,000
02/10/26
5
6
6,001
25 SUGAR MILL DRIVE, Osprey, FL
0.36
Single-Family Home
$1,300,000
07/22/26
3
3.5
3,066

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
453 WEBBS COVE, Osprey, FL 34229
0.03
$1,666,200
3
3.5
3,953
Off Market
442 WEBBS COVE, Osprey, FL 34229
0.04
$2,347,300
3
3.5
3,768
Off Market
252 OSPREY POINT DRIVE, Osprey, FL 34229
0.10
$1,856,900
4
3.5
3,780
Off Market
460 WEBBS COVE, Osprey, FL 34229
0.05
$2,631,800
3
4
5,479
Off Market
282 SHELL MIDDEN COURT, Osprey, FL 34229
0.10
-
3
4.5
3,699
Off Market
230 OSPREY POINT DRIVE, Osprey, FL 34229
0.15
$2,329,700
3
3.5
3,586
Off Market
75 OSPREY POINT DRIVE, Osprey, FL 34229
0.12
$1,595,000
4
4
4,001
For Sale
137 OSPREY POINT DRIVE, Osprey, FL 34229
0.14
$1,285,000
4
3
3,303
Recently Sold
156 BISHOPS COURT ROAD, Osprey, FL 34229
0.20
$1,289,000
3
3.5
3,112
For Sale
143 OSPREY POINT DRIVE, Osprey, FL 34229
0.16
$575,000
-
-
-
For Sale
325 OSPREY POINT DRIVE, Osprey, FL 34229
0.19
$1,500,000
3
4.5
3,905
Recently Sold

Local Information

  • Map ViewExplore the area around 449 WEBBS COVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2006
Lot Size
0.4 acres
Living Area
5,287 sqft
Price/Sqft
$467/sqft
Parking
3 Car Garage
HOA
$492/Monthly

About this House

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.
449 WEBBS COVE, Osprey, FL 34229 is a 4 bedroom, 4 bathroom, 5,287 sqft single-family home built in 2006. It last sold for $2,470,000 on Aug 27, 2026 (7% below the $2,650,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,479,900, with a rent estimate of $6,550/month.
Last check for updates: about 5 hours ago
Listed by Rosalie Phillips, (941) 544-4430
MICHAEL SAUNDERS & COMPANY, (941) 966-8000
Bought with: David Miller, (404) 931-7529, BRIGHT REALTY, (941) 552-6036
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4688291
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 449 WEBBS COVE

Interior Features

Interior Details
Number of Rooms: 12Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dinette, Dining Room, Foyer, Great Room, Kitchen, Living Room, Media Room, OfficeWet Bar
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5287 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Propane, Public, Sewer Connected, Sprinkler Well, Street Lights, Underground Utilities, Water ConnectedAppliances: 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 RefrigeratorDishwasherDisposalDryerLaundry: Electric Dryer Hookup,Inside,Laundry Room,Washer HookupRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Gas, Living RoomSpa: In GroundHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Window TreatmentsDoor: French Doors, Outdoor Grill, Outdoor Kitchen, Sliding DoorsFlooring: Carpet, Travertine, Hardwood
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Travertine, Hardwood
View
Has a ViewView: Water, Lake
Security
Security: Gated Community, Security Gate, Security System, Security System Owned, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Covered, Deck, Enclosed, Front Porch, Patio, ScreenedVegetation: Mature Landscaping, Trees/LandscapedExterior: Garden, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Mailbox, Private Yard, Rain Gutters, Sprinkler MeteredFoundation: Block, SlabGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Circular Driveway,Garage Door Opener,Garage Faces Side,Oversized,Parking Pad
Pool
Pool: Gunite, In Ground, Lighting, Outside Bath Access, Screen Enclosure, TilePool
Frontage
WaterfrontWaterfront: Lake FrontRoad Frontage: Private RoadRoad Surface Type: Paved, AsphaltOn Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 18

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Custom,Traditional
Building
Construction Materials: Block, Brick, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 0142040028

Price & Status

Price
List Price: $2,650,000Price Per Sqft: $467/sqft
Status Change & Dates
Off Market Date: Tue May 19 2026

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: OSPREYCommunity: OAKS
School Information
Elementary School: Laurel Nokomis ElementaryJr High / Middle School: Sarasota MiddleHigh School: Venice Senior High

Building

Building Area
Building Area: 6876 Square Feet
Community rooms
Fitness Center

Community

Community Features: Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Special Community Restrictions, Tennis Court(s)Not Senior Community

HOA

HOA Fee Includes: 24-Hour Guard, Common Area Taxes, Reserve Fund, Manager, Private Road, SecurityHOA Name: Access Management - Hope RootHOA Phone: 813-607-2220Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $492/Monthly

Lot Information

Lot Area: 0.40 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4688291Water ViewWater View: Water, LakeShowing Advance Notice: 24Showing AttendedShowing Requirements: 24 Hour Notice, Appointment Only, Contact Call Center, Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12115-N-0142040028-R-N

Additional Information

HOA Amenities: Basketball Court,Clubhouse,Elevator(s),Fitness Center,Gated,Golf Course,Pickleball Court(s),Pool,Security,Vehicle Restrictions,Wheelchair Access

Price and Tax history

DateEventPrice
Aug 27, 2026
Source: Stellar MLS #A4688291
Sold
$2,470,000
May 19, 2026
Source: Stellar MLS #A4688291
Pending
$2,650,000
May 1, 2026
Source: Stellar MLS #A4688291
Listed For Sale
$2,650,000
May 30, 2002
Source: N/A
Sold
$359,000
May 8, 2001
Source: N/A
Sold
$280,000

Market trends in Osprey

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
133
7MoM

Around this home

What Locals Say about Osprey

At least 46 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 87 % Say it's dog friendly

  • 85 % Say it's quiet

  • 84 % Say parking is easy

  • 75 % Say people would walk alone at night

  • 74 % Say there's wildlife

  • 67 % Say yards are well-kept

  • 67 % Say there's holiday spirit

  • 64 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 42 % Say streets are well-lit

  • 41 % Say it's walkable to grocery stores

  • 41 % Say there are community events

  • 31 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Lindsey W.
    "It’s a quiet and low key suburb area of Sarasota county. It’s very accessible to I-75 and Nokomis beach and about a 25 minute drive to siesta key beach. "
    4
    Flag
  • Mary V.
    "I am retired now but my commute to Stickney Point was only about 10 min and downtown was about 25 min during rush hour when there is no construction "
    0
    Flag
  • Mary V.
    "Pineview School is very close, nice safe area for children. CVS and Publix are also close, as well as Historic Spanish Pointe. The beach is ten minutes or less."
    3
    Flag
  • Bob T.
    "I don’t commute....retired. There are no sidewalks here and our street has a large amount of speeders making walking dangerous. Some neighbors park on the county right of way destroying our water flow/drainage which has caused flooding here. Many homes are unkept even though there is an active hoa."
    14
    Flag
  • Bob T.
    "Neighborhood is pet friendly. Wide road we walking dogs. Only problem noticed now is daily construction vehicles speeding in neighborhood."
    1
    Flag
  • Larysathor
    "Well, the Mother Nature taking its tall, water level raised over last ten years and a lot of beaches are washed out to nonexistence."
    0
    Flag
  • Brenda F. D.
    "Neighborhood is beautiful love the area close to everything and beaches and shopping . Local restaurant "
    1
    Flag
  • Michelle C.
    "I've lived in this neighborhood for twenty years +. My neighbors are the friendliest. We all look out for each other and lend a hand when needed. Can't think of anywhere else I'd want to live."
    0
    Flag
  • nancybuscher
    "This quiet, beautifully landscaped, pet friendly subdivision is close to beaches, shopping, restaurants, cultural events in Sarasota and Venice, beside Oscar Scherer State Park for hickers & boaters, and has easy access to airports by way of US41 & I-75."
    0
    Flag
  • info
    "Centrally located, minutes to beaches and shopping"
    1
    Flag
  • bookwoman39
    "Wonderful community, close to Sarasota and all restaurants, cultural activities, etc. The condo development is a designated bird sanctuary. Nice pools, exercise room, community room. Good neighbors. What the development lacks is diversity. "
    0
    Flag
  • trishmainey1111
    "Osprey Florida is one of the most beautiful, accessible communities in Florida. Ten minutes to the white sands beach and ten minutes to I-75. "
    1
    Flag
  • Gail L.
    "I work here, belong to the club and have lived in the neighborhood for the last 12 years it is one of 5 golf communities I have belonged to and bar none my favorite due to the people that live here. They are multicultural, down to earth and just fabulous. This is a community that rates above the rest . it is very common for folks to move up and down in house sizes and styles as their lifestyles change. Give me a call as I'd love to show you around. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 449 WEBBS COVE

  • What is 449 WEBBS COVE estimated to be worth?
    Trulia's estimated value for 449 WEBBS COVE in Osprey, FL is $2,479,900.
  • What is the price history for 449 WEBBS COVE?
    449 WEBBS COVE in Osprey, FL last sold for $2,470,000 in August 2026.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Osprey?
    Residents describe Osprey, FL as dog-friendly, quiet, and easy to park in. Most residents say you need a car. See recently sold homes in Osprey, FL.
  • Does 449 WEBBS COVE have air conditioning?
    Yes, 449 WEBBS COVE in Osprey, FL has air conditioning.
  • Does 449 WEBBS COVE have a pool?
    Yes, 449 WEBBS COVE in Osprey, FL has a pool.

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