441 Webbs Cv, Osprey, FL 34229
Property image
Property image
OFF MARKET

441 Webbs Cv
Osprey, FL 34229

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

$1,410,200

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $8,727/mo*
Refinance Your Home

$1,410,200

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $8,727/mo*
Refinance Your Home
3 Beds
4 Baths
3,767 sqft
(on 0.45 acres)

Home Value

Trulia Estimate
$1.41M
Since last month
Decreased$33K (-2.3%)
Since last year
Decreased$33K (-2.3%)
Since last sale
Increased$795K (+130.4%)
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 +97% in the last 10 years
MonthEstimated value
2026
August 2026$1.41M
July 2026$1.4M
June 2026$1.44M
May 2026$1.44M
April 2026$1.45M
March 2026$1.49M
February 2026$1.49M
January 2026$1.42M
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
133 Osprey Point Dr, Osprey, FL
0.14
Single-Family Home
$1,054,284
06/29/26
4
3
4,099
76 OSPREY POINT DRIVE, Osprey, FL
0.15
Single-Family Home
$1,450,000
06/15/26
3
4.5
4,364
325 OSPREY POINT DRIVE, Osprey, FL
0.17
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
25 SUGAR MILL DRIVE, Osprey, FL
0.33
Single-Family Home
$1,300,000
07/22/26
3
3.5
3,066
137 OSPREY POINT DRIVE, Osprey, FL
0.17
Single-Family Home
$1,285,000
04/08/26
4
3
3,303
919 TRANQUILITY CIRCLE, Osprey, FL
0.47
Single-Family Home
$750,000
08/14/26
4
3.5
2,854
140 SUGAR MILL DRIVE, Osprey, FL
0.47
Single-Family Home
$1,325,000
06/16/26
4
4
3,286
370 SUGAR MILL DRIVE, Osprey, FL
0.26
Single-Family Home
$2,189,000
02/09/26
5
5.5
4,783
67 SUGAR MILL DRIVE, Osprey, FL
0.42
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
1828 MOVA STREET, Sarasota, FL
0.78
Single-Family Home
$667,500
11/21/25
3
3
3,157

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
442 WEBBS COVE, Osprey, FL 34229
0.04
$2,321,100
3
3.5
3,768
Off Market
460 WEBBS COVE, Osprey, FL 34229
0.06
$2,613,800
3
4
5,479
Off Market
75 OSPREY POINT DRIVE, Osprey, FL 34229
0.10
$1,595,000
4
4
4,001
For Sale
453 WEBBS COVE, Osprey, FL 34229
0.05
$1,656,400
3
3.5
3,953
Off Market
76 OSPREY POINT DRIVE, Osprey, FL 34229
0.15
$1,450,000
3
4.5
4,364
Recently Sold
101 OSPREY POINT DRIVE, Osprey, FL 34229
0.15
$4,790,000
4
5.5
5,087
For Sale
282 SHELL MIDDEN COURT, Osprey, FL 34229
0.12
$1,349,500
3
4.5
3,699
Off Market
252 OSPREY POINT DRIVE, Osprey, FL 34229
0.12
$1,848,200
4
3.5
3,780
Off Market
49 OSPREY POINT DRIVE, Osprey, FL 34229
0.18
$2,399,000
4
3.5
3,953
For Sale
325 OSPREY POINT DRIVE, Osprey, FL 34229
0.17
$1,500,000
3
4.5
3,905
Recently Sold
137 OSPREY POINT DRIVE, Osprey, FL 34229
0.17
$1,285,000
4
3
3,303
Recently Sold
324 OSPREY POINT DRIVE, Osprey, FL 34229
0.19
$2,948,700
5
5
5,758
Off Market

Local Information

  • Map ViewExplore the area around 441 Webbs Cv.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1992
Lot Size
0.45 acres
Living Area
3,767 sqft
Price/Sqft
$374
Parking
Garage

About this House

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.
441 Webbs Cv, Osprey, FL 34229 is a 3 bedroom, 4 bathroom, 3,767 sqft single-family home built in 1992. It last sold for $610,000 on Nov 21, 2014. It is currently off market. The Trulia Estimate is $1,410,200, with a rent estimate of $5,246/month.

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 and Tax history

DateEventPrice
Nov 21, 2014
Source: N/A
Sold
$610,000
Apr 11, 2014
Source: Agent Provided
PriceChange
$660,000
Price decreased by 2%
Jan 17, 2014
Source: Agent Provided
PriceChange
$675,000
Price decreased by 3%
Oct 5, 2013
Source: Agent Provided
PriceChange
$695,000
Price decreased by 4%
Aug 16, 2013
Source: Agent Provided
Listed For Sale
$725,000

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
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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

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Homes for sale near 441 Webbs Cv

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Off Market Homes Near 441 Webbs Cv

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Frequently asked questions about 441 Webbs Cv

  • What is 441 Webbs Cv estimated to be worth?
    Trulia's estimated value for 441 Webbs Cv in Osprey, FL is $1,410,200.
  • What is the price history for 441 Webbs Cv?
    441 Webbs Cv in Osprey, FL last sold for $610,000 in November 2014.
  • 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 441 Webbs Cv have air conditioning?
    Yes, 441 Webbs Cv in Osprey, FL has air conditioning.
  • Does 441 Webbs Cv have a pool?
    Yes, 441 Webbs Cv in Osprey, FL has a pool.