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)

$660,200

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $4,050/mo*
Refinance Your Home

$660,200

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $4,050/mo*
Refinance Your Home
4 Beds
3 Baths
2,510 sqft
(on 0.29 acres)

Local Information

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

Description

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.
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
View
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 40 Webb St

DatePriceEventSource
02/16/2023$712,000Sold
N/A
01/14/2023$749,000PendingStellar MLS #A4543500
10/30/2022$749,000PendingToActiveStellar MLS #A4543500
10/26/2022$749,000PendingStellar MLS #A4543500
10/24/2022$749,000Listed For SaleStellar MLS #A4543500
09/23/2022ListingRemovedStellar MLS #A4543500
07/28/2022$799,000Listed For SaleStellar MLS #A4543500
11/19/2012$284,000Sold
N/A
03/07/2012$299,000PriceChange
Agent Provided
01/09/2011$347,500Listed For SaleAgent Provided
10/20/2010$347,500ListingRemovedAgent Provided
10/10/2010$347,500PriceChange
Agent Provided
02/02/2010$349,500PriceChange
Agent Provided
10/04/2009$395,500Listed For SaleAgent Provided
12/30/2002$280,000Sold
N/A
11/05/2001$234,000Sold
N/A
09/10/1997$55,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$5,605
Assessment$464,800
Home facts updated by county records

Comparable Sales for 40 Webb St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
51 Webb St, Osprey, FL
0.02
Single-Family Home
$570,000
04/03/26
3
2.5
2,130
38 W Bay St, Osprey, FL
0.21
Single-Family Home
$865,000
02/10/26
3
2
2,124
315 Bayshore Dr, Osprey, FL
0.51
Single-Family Home
$527,500
02/27/26
3
3
2,384
228 Saint James Park, Osprey, FL
0.57
Single-Family Home
$1,600,000
05/14/26
3
2.5
2,425
67 Sugar Mill Dr, Osprey, FL
0.35
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
26 Bay Acres Ave, Osprey, FL
0.52
Single-Family Home
$479,000
09/10/25
3
2
1,904
223 Saint James Park, Osprey, FL
0.53
Single-Family Home
$1,197,000
05/30/25
3
4
3,321
444 Washington Ave, Osprey, FL
0.30
Single-Family Home
$200,000
10/06/25
3
2
1,284
240 Patterson Ave, Osprey, FL
0.27
Single-Family Home
$350,000
10/16/25
3
2
1,360
115 Green St, Osprey, FL
0.31
Single-Family Home
$358,000
11/13/25
2
2
1,503

Assigned Schools

These are the assigned schools for 40 Webb St.
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What Locals Say about Osprey

At least 45 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

  • 74 % Say people would walk alone at night

  • 73 % Say there's wildlife

  • 66 % Say yards are well-kept

  • 66 % Say there's holiday spirit

  • 64 % Say they plan to stay for at least 5 years

  • 53 % Say neighbors are friendly

  • 49 % Say there are sidewalks

  • 42 % Say streets are well-lit

  • 41 % Say it's walkable to restaurants

  • 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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40 Webb St, Osprey, FL 34229 is a 4 bedroom, 3 bathroom, 2,510 sqft single-family home built in 1956. This property is not currently available for sale. 40 Webb St was last sold on Feb 16, 2023 for $712,000. The current Trulia Estimate for 40 Webb St is $660,200.