442 Webbs Cv, Osprey, FL 34229
OFF MARKET

442 Webbs Cv
Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 3,768 sqft (on 0.65 acres)

$2,365,700

Trulia Estimate
as of May 23, 2026
Est. Refi. Payment $14,504/mo*
Refinance Your Home

$2,365,700

Trulia Estimate
as of May 23, 2026
Est. Refi. Payment $14,504/mo*
Refinance Your Home
3 Beds
3.5 Baths
3,768 sqft
(on 0.65 acres)

Local Information

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

Description

**FULLY RENOVATED** ELEGANT, ARCHITECTURALLY EXQUISITE ESTATE designed by famed architect, Bo MacEwen. The grand front entry of this stately home will take your breath away as you step inside and marvel at its timeless elegance and gaze out toward the gorgeous pool and pond with fountain. Just steps away from Sarasota Bay waters and behind the gates of the secluded and highly sought-after “Oaks-Bayside” neighborhood. This home is nicely positioned on an oversized lot, set back from the road on a private cul de sac street. THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS program with 12 Har-Tru Hydro-Grid tennis courts, 4 Pickleball Courts, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Equity OR Social Membership is required and available.
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. This description is from March 15, 2024

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Pool
View
Water, Pond
HOA
$417/Monthly
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 442 Webbs Cv

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Dining Room, Kitchen, Living Room, OfficeWet Bar
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3768 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Available, Phone Available, Sewer Connected, Underground Utilities, Water ConnectedAppliances: Dishwasher, Disposal, Dryer, Freezer, Microwave, Range, Range Hood, Refrigerator, WasherDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Electric,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Living RoomHas a FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Engineered Hardwood, Porcelain Tile, Tile
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneFloors: Engineered Hardwood, Porcelain Tile, Tile
View
Has a ViewView: Water, Pond

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Front Porch, Porch, Rear PorchVegetation: Mature Landscaping, Trees/LandscapedExterior: Irrigation SystemFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Door Opener,Garage Faces Side
Pool
Pool: Gunite, In Ground, LightingPool
Frontage
Responsible for Road Maintenance: Private Maintained RoadRoad Surface Type: Asphalt, PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1983
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Parcel Number: 0142050005

Price & Status

Price
List Price: $2,375,000
Status Change & Dates
Off Market Date: Wed Jan 31 2024Possession Timing: Negotiable

Active Status

MLS Status: Sold

Location

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

Building

Building Area
Building Area: 5198 Square Feet
Community rooms
Fitness Center

Community

Community Features: Dock, Intracoastal Waterway, Clubhouse, Fitness Center, Gated Community - Guard, PoolNot Senior Community

HOA

HOA Fee Includes: 24-Hour Guard, Common Area TaxesHOA Name: ACCESS MANAGEMENT / Vanessa Diaz-HemmerickAssociation for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $417/Monthly

Lot Information

Lot Area: 0.65 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4592469Water ViewWater View: Water, PondShowing AttendedShowing Considerations: No SignShowing Requirements: Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12115-N-0142050005-R-N

Additional Information

HOA Amenities: Basketball Court,Clubhouse,Fence Restrictions,Fitness Center,Gated,Pickleball Court(s),Pool,Recreation Facilities,Tennis Court(s),Vehicle Restrictions
Last check for updates: about 4 hours ago
Listed by Mark Lyda, (941) 586-2670
GENEROUS PROPERTY, (941) 275-9399
Bought with: Mark Lyda, (941) 586-2670, GENEROUS PROPERTY, (941) 275-9399
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4592469
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

Price History for 442 Webbs Cv

DatePriceEventSource
03/15/2024$2,375,000Sold
Stellar MLS #A4592469
02/01/2024$2,375,000PendingStellar MLS #A4592469
02/01/2024$2,375,000Listed For SaleStellar MLS #A4592469
07/19/2021$1,050,000Sold
Stellar MLS #A4492928
04/13/2021ListingRemovedStellar MLS
03/23/2021$1,099,000PendingStellar MLS #A4492928
01/26/2021$905,000Sold
N/A
12/07/1998$669,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$21,062
Assessment$1,777,800
Home facts updated by county records

Comparable Sales for 442 Webbs Cv

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
230 Osprey Point Dr, Osprey, FL
0.19
Single-Family Home
$2,400,000
06/02/25
3
3.5
3,586
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
0.20
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
112 Osprey Point Dr, Osprey, FL
0.16
Single-Family Home
$2,315,000
10/30/25
4
5.5
8,635
137 Osprey Point Dr, Osprey, FL
0.15
Single-Family Home
$1,285,000
04/08/26
4
3
3,303
370 Sugar Mill Dr, Osprey, FL
0.24
Single-Family Home
$2,189,000
02/09/26
5
5.5
4,783
340 Osprey Point Dr, Osprey, FL
0.26
Single-Family Home
$1,900,000
02/10/26
5
6
6,001
67 Sugar Mill Dr, Osprey, FL
0.42
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
8900 Fishermens Bay Dr, Sarasota, FL
0.80
Single-Family Home
$3,485,000
09/29/25
4
3.5
4,158

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Assigned Schools

These are the assigned schools for 442 Webbs Cv.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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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442 Webbs Cv, Osprey, FL 34229 is a 3 bedroom, 4 bathroom, 3,768 sqft single-family home built in 1983. This property is not currently available for sale. 442 Webbs Cv was last sold on Mar 15, 2024 for $2,375,000 (0% higher than the asking price of $2,375,000). The current Trulia Estimate for 442 Webbs Cv is $2,365,700.