40 Webb St, Osprey, FL 34229
OFF MARKET

40 Webb St
Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,510 sqft (on 0.29 acres)

$660,900

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $4,133/mo*
Refinance Your Home

$660,900

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $4,133/mo*
Refinance Your Home
4 Beds
3 Baths
2,510 sqft
(on 0.29 acres)

Home Value

Trulia Estimate
$661K
Since last month
Decreased$15K (-2.2%)
Since last year
Decreased$12K (-1.7%)
Since last sale
Decreased$51K (-7.2%)
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 +92% in the last 10 years
MonthEstimated value
2026
August 2026$661K
July 2026$660K
June 2026$676K
May 2026$667K
April 2026$663K
March 2026$663K
February 2026$657K
January 2026$649K
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
51 WEBB STREET, Osprey, FL
0.02
Single-Family Home
$570,000
04/03/26
3
2.5
2,130
38 W BAY STREET, Osprey, FL
0.21
Single-Family Home
$865,000
02/10/26
3
2
2,124
140 SUGAR MILL DRIVE, Osprey, FL
0.27
Single-Family Home
$1,325,000
06/16/26
4
4
3,286
212 WASHINGTON AVENUE, Osprey, FL
0.16
Single-Family Home
$416,400
04/24/26
3
2
1,478
315 BAYSHORE DRIVE, Osprey, FL
0.51
Single-Family Home
$527,500
02/27/26
3
3
2,384
919 TRANQUILITY CIRCLE, Osprey, FL
0.72
Single-Family Home
$750,000
08/14/26
4
3.5
2,854
228 SAINT JAMES PARK, Osprey, FL
0.57
Single-Family Home
$1,600,000
05/14/26
3
2.5
2,425
25 SUGAR MILL DRIVE, Osprey, FL
0.47
Single-Family Home
$1,300,000
07/22/26
3
3.5
3,066
67 SUGAR MILL DRIVE, Osprey, FL
0.35
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
26 BAY ACRES AVENUE, Osprey, FL
0.52
Single-Family Home
$479,000
09/10/25
3
2
1,904

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
51 WEBB STREET, Osprey, FL 34229
0.02
$570,000
3
2.5
2,130
Recently Sold
162 PUESTA DEL SOL, Osprey, FL 34229
0.07
$2,336,600
4
4.5
4,747
Off Market
110 PINE AVENUE, Osprey, FL 34229
0.11
$649,000
3
2
2,058
For Sale
3820 PARROT BAY COURT LOT 9, Osprey, FL 34229
0.18
$825,000
-
-
-
For Sale
212 WASHINGTON AVENUE, Osprey, FL 34229
0.16
$420,000
3
2
1,478
For Sale
38 W BAY STREET, Osprey, FL 34229
0.21
$865,000
3
2
2,124
Recently Sold
242 WASHINGTON AVENUE, Osprey, FL 34229
0.17
$181,800
2
1
630
Off Market
133 W BAY STREET, Osprey, FL 34229
0.25
$1,936,700
4
4
3,168
Off Market
133 W BAY STREET LOT 1, Osprey, FL 34229
0.25
-
-
-
-
Off Market
34 WASHINGTON AVENUE LOT 67, Osprey, FL 34229
0.24
$475,000
-
-
-
Recently Sold
208 PENNSYLVANIA AVENUE, Osprey, FL 34229
0.21
$259,000
3
2
900
Off Market
214 PATTERSON AVENUE, Osprey, FL 34229
0.27
$297,200
3
2
1,092
Off Market

Local Information

  • Map ViewExplore the area around 40 Webb St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1956
Lot Size
0.29 acres
Living Area
2,510 sqft
Price/Sqft
$263
Parking
Garage

About this House

Enjoy Florida living in this delightful Key West style home in Osprey; minutes away from historical Spanish Point, fishing pier and open bay sunsets. Open the front door to a bright and spacious floor plan.Originally built in 1956, house was meticulously rebuilt and remodeled by 2001. In addition, a detached oversized 2 car garage was added in 2005 offering ample attic storage space. Features include 3 bedrooms, a large bonus room (possible fourth bedroom),two and one-half baths, and a screened paver lanai surrounded by lush Florida vegetation. High ceilings, crown moulding, 6" pickeled baseboard, wooden floors in the master suite, and beautiful terracotta tile in the main floor are among the many outstanding characteristics. A home with warmth and charm you will want to call your own.
40 Webb St, Osprey, FL 34229 is a 4 bedroom, 3 bathroom, 2,510 sqft single-family home built in 1956. It last sold for $712,000 on Feb 16, 2023. It is currently off market. The Trulia Estimate is $660,900, with a rent estimate of $3,131/month.

Home Details for 40 Webb St

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood, Laminate
Interior Details
Number of Rooms: 5

Exterior Features

Exterior Home Features
Roof: MetalExterior: OtherFoundation Type: ConcretePatio
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1956Year Updated: 1990
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.29 acres

Price and Tax history

DateEventPrice
Feb 16, 2023
Source: eXp Realty #86397090
Sold
$712,000
Jan 14, 2023
Source: Stellar MLS #A4543500
Pending
$749,000
Oct 30, 2022
Source: Stellar MLS #A4543500
PendingToActive
$749,000
Oct 26, 2022
Source: Stellar MLS #A4543500
Pending
$749,000
Oct 24, 2022
Source: Stellar MLS #A4543500
Listed For Sale
$749,000

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 40 Webb St

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Off Market Homes Near 40 Webb St

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Frequently asked questions about 40 Webb St

  • What is 40 Webb St estimated to be worth?
    Trulia's estimated value for 40 Webb St in Osprey, FL is $660,900.
  • What is the price history for 40 Webb St?
    40 Webb St in Osprey, FL last sold for $712,000 in February 2023.
  • 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.
  • How big is the lot at 40 Webb St?
    The lot at 40 Webb St in Osprey, FL is about 0.29 acres (12,632 sq ft).
  • Does 40 Webb St have a garage?
    Yes, 40 Webb St in Osprey, FL has a garage.