441 Webbs Cv, Osprey, FL 34229
OFF MARKET

441 Webbs Cv
Osprey, FL 34229

  • 3 Beds
  • 4 Baths
  • 3,767 sqft (on 0.45 acres)

$1,426,000

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $8,787/mo*
Refinance Your Home

$1,426,000

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $8,787/mo*
Refinance Your Home
3 Beds
4 Baths
3,767 sqft
(on 0.45 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

The lifestyle you've imagined awaits you in the Oaks Club. A beautiful location tucked away in private exclusive Oaks Bayside sits on a treed lakefront lot with scenic open views. Custom built Traditional with an open floor plan, 3 bedroom, 3.5 bath plus study with all major rooms opening to the open outdoor area. One fireplace, two car garage with courtyard driveway. This home has hurricane protection and a finished air conditioned attic for bountiful storage options. Master suite conveniently opens topool area and has beautiful lake views. A delightful home. Generously sized family room and kitchen area for family gatherings and daily living. Oversized laundry room. With oversized cedar lined room which can be a 2nd office. Large lanai with pool and jacuzzi. Window pass thru -- from catering kitchen conveniently located off the lanai. Enjoy the 36 holes of golf, 12 har-tru tennis courts, croquet and social calendar the Oaks Club offers. Oaks club membership required with property purchase.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 441 Webbs Cv

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
Number of Rooms: 9
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: OtherExterior: StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking: Garage, Open

Property Information

Year Built
Year Built: 1992Year Updated: 1997
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.45 acres

Price History for 441 Webbs Cv

DatePriceEventSource
11/21/2014$610,000Sold
N/A
04/11/2014$660,000PriceChange
Agent Provided
01/17/2014$675,000PriceChange
Agent Provided
10/05/2013$695,000PriceChange
Agent Provided
08/16/2013$725,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$8,228
Assessment$1,211,000
Home facts updated by county records

Comparable Sales for 441 Webbs Cv

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
282 Shell Midden Ct, Osprey, FL
0.12
Single-Family Home
$1,405,000
07/11/25
3
4.5
3,699
325 Osprey Point Dr, Osprey, FL
0.17
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
230 Osprey Point Dr, Osprey, FL
0.17
Single-Family Home
$2,400,000
06/02/25
3
3.5
3,586
137 Osprey Point Dr, Osprey, FL
0.17
Single-Family Home
$1,285,000
04/08/26
4
3
3,303
133 Osprey Point Dr, Osprey, FL
0.14
Single-Family Home
$23,413
02/26/26
4
3
4,099
370 Sugar Mill Dr, Osprey, FL
0.26
Single-Family Home
$2,189,000
02/09/26
5
5.5
4,783
67 Sugar Mill Dr, Osprey, FL
0.42
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
1828 Mova St, Sarasota, FL
0.78
Single-Family Home
$667,500
11/21/25
3
3
3,157
112 Osprey Point Dr, Osprey, FL
0.20
Single-Family Home
$2,315,000
10/30/25
4
5.5
8,635
8871 Fishermens Bay Dr, Sarasota, FL
0.82
Single-Family Home
$1,114,500
10/16/25
3
3
3,214

Assigned Schools

These are the assigned schools for 441 Webbs Cv.
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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

  • 53 % Say neighbors are friendly

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 42 % Say streets are well-lit

  • 41 % Say there are community events

  • 40 % Say it's walkable to grocery stores

  • 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

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441 Webbs Cv, Osprey, FL 34229 is a 3 bedroom, 4 bathroom, 3,767 sqft single-family home built in 1992. This property is not currently available for sale. 441 Webbs Cv was last sold on Nov 21, 2014 for $610,000. The current Trulia Estimate for 441 Webbs Cv is $1,426,000.