442 WEBBS COVE, Osprey, FL 34229
OFF MARKET

442 WEBBS COVE
Osprey, FL 34229

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

$2,339,800

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $14,419/mo*
Refinance Your Home

$2,339,800

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $14,419/mo*
Refinance Your Home
3 Beds
3.5 Baths
3,768 sqft
(on 0.65 acres)

Home Value

Trulia Estimate
$2.34M
Since last month
Increased$15K (+0.7%)
Since last year
Increased$228K (+10.8%)
Since last sale
Decreased$30K (-1.3%)
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 +149% in the last 10 years
MonthEstimated value
2026
August 2026$2.35M
July 2026$2.33M
June 2026$2.35M
May 2026$2.37M
April 2026$2.38M
March 2026$2.4M
February 2026$2.38M
January 2026$2.38M
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
76 OSPREY POINT DRIVE, Osprey, FL
0.14
Single-Family Home
$1,450,000
06/15/26
3
4.5
4,364
325 OSPREY POINT DRIVE, Osprey, FL
0.20
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
112 OSPREY POINT DRIVE, Osprey, FL
0.16
Single-Family Home
$2,315,000
10/30/25
4
5.5
8,635
137 OSPREY POINT DRIVE, Osprey, FL
0.15
Single-Family Home
$1,285,000
04/08/26
4
3
3,303
370 SUGAR MILL DRIVE, Osprey, FL
0.24
Single-Family Home
$2,189,000
02/09/26
5
5.5
4,783
25 SUGAR MILL DRIVE, Osprey, FL
0.35
Single-Family Home
$1,300,000
07/22/26
3
3.5
3,066
340 OSPREY POINT DR, Osprey, FL
0.26
Single-Family Home
$1,900,000
02/10/26
5
6
6,001
67 SUGAR MILL DRIVE, Osprey, FL
0.42
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
140 SUGAR MILL DRIVE, Osprey, FL
0.47
Single-Family Home
$1,325,000
06/16/26
4
4
3,286

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
460 WEBBS COVE, Osprey, FL 34229
0.03
$2,611,800
3
4
5,479
Off Market
453 WEBBS COVE, Osprey, FL 34229
0.04
$1,656,400
3
3.5
3,953
Off Market
101 OSPREY POINT DRIVE, Osprey, FL 34229
0.11
$4,790,000
4
5.5
5,087
For Sale
75 OSPREY POINT DRIVE, Osprey, FL 34229
0.10
$1,595,000
4
4
4,001
For Sale
282 SHELL MIDDEN COURT, Osprey, FL 34229
0.12
$1,349,500
3
4.5
3,699
Off Market
76 OSPREY POINT DRIVE, Osprey, FL 34229
0.14
$1,450,000
3
4.5
4,364
Recently Sold
112 OSPREY POINT DRIVE, Osprey, FL 34229
0.16
$2,315,000
4
5.5
8,635
Recently Sold
137 OSPREY POINT DRIVE, Osprey, FL 34229
0.15
$1,285,000
4
3
3,303
Recently Sold
252 OSPREY POINT DRIVE, Osprey, FL 34229
0.14
$1,856,900
4
3.5
3,780
Off Market
143 OSPREY POINT DRIVE, Osprey, FL 34229
0.17
$575,000
-
-
-
For Sale
148 OSPREY POINT DRIVE LOT 35, Osprey, FL 34229
0.19
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 442 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
1983
Lot Size
0.65 acres
Living Area
3,768 sqft
Price/Sqft
$621
Parking
2 Car Garage
HOA
$417/Monthly

About this House

**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.
442 WEBBS COVE, Osprey, FL 34229 is a 3 bedroom, 4 bathroom, 3,768 sqft single-family home built in 1983. It last sold for the $2,375,000 asking price on Mar 15, 2024. It is currently off market. The Trulia Estimate is $2,339,800, with a rent estimate of $6,523/month.
Last check for updates: about 2 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

Home Details for 442 WEBBS COVE

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

Price and Tax history

DateEventPrice
Mar 15, 2024
Source: Stellar MLS #A4592469
Sold
$2,375,000
Feb 1, 2024
Source: Stellar MLS #A4592469
Pending
$2,375,000
Feb 1, 2024
Source: Stellar MLS #A4592469
Listed For Sale
$2,375,000
Jul 19, 2021
Source: Stellar MLS #A4492928
Sold
$1,050,000
Apr 13, 2021
Source: Stellar MLS
ListingRemoved

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 442 WEBBS COVE

  • What is 442 WEBBS COVE estimated to be worth?
    Trulia's estimated value for 442 WEBBS COVE in Osprey, FL is $2,339,800.
  • What is the price history for 442 WEBBS COVE?
    442 WEBBS COVE in Osprey, FL last sold for $2,375,000 in March 2024.
  • 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 442 WEBBS COVE have air conditioning?
    Yes, 442 WEBBS COVE in Osprey, FL has air conditioning.
  • Does 442 WEBBS COVE have a pool?
    Yes, 442 WEBBS COVE in Osprey, FL has a pool.

Explore by feature - Pet Friendly

11 pet-friendly rentals in Osprey, FL

Explore by feature - Garage

17 rentals with a garage in Osprey, FL

Explore by feature - Air Conditioning

28 rentals with air conditioning in Osprey, FL

Explore by feature - Pool

24 rentals with a pool in Osprey, FL

Explore by feature - Washer/dryer

28 rentals with a washer/dryer in Osprey, FL

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 442 WEBBS COVE

Skip to last item
Skip to first item

Homes for sale near 442 WEBBS COVE

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item