101 Webb St, Osprey, FL 34229
OFF MARKET

101 Webb St
Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,860 sqft

$796,600

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $4,942/mo*
Refinance Your Home

$796,600

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $4,942/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,860 sqft

Local Information

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

Description

Your dream home, west of the Trail, in Osprey, FL, has arrived! This 2007 Mediterranean style, two-story home, is located just a few houses from beautiful Sarasota Bay and less than a 1/2 mile to the Historic Spanish Point, the Main Street Fishing Pier, and Evie's New Tiki Bar and Restaurant! This 2,860 sq. ft. high-ceilinged home features 3 bedrooms, 2.5 bathrooms, a stunning pool, a roomy 2-car side load garage, and a second floor loft. The first floor of the home features an easy access laundry room, open concept dining room, great room, and kitchen. The kitchen includes a gas range, granite countertops, and updated stainless steel appliances. New lighting fixtures have just been installed and the entire house has been freshly painted! Just off the kitchen is the living room with a neutral ceramic tile floor, a wet bar and French doors that lead to the tropical pool oasis. The spacious master suite is also located on the first floor with French doors accessing the pool. The master bathroom has a clawfoot soaking tub, large shower, his and her closets, and separate vanities. The second floor includes hardwood floors, new light fixtures, 2 bedrooms, a bathroom with stand-up shower, a loft/media room, and a generous sized balcony overlooking the pool and fenced yard. Enjoy the perks of no HOA--so bring your boat or RV! Conveniently located near Casey Key, Oscar Scherer State Park, Nokomis Beach, Siesta Key and only 5 minutes to the well-known Pine View School for the Gifted. Bonus: There is a kayak launch at the end of the street into Sarasota Bay, and the sellers are offering a 1-year home warranty with purchase! This is a rare find, so don't let this one get away! Book your appointment today!
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, Deck, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 101 Webb St

Interior Features

Heating & Cooling
Heating: Forced Air, Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Interior Details
Number of Rooms: 8Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Carport, Garage Attached

Property Information

Year Built
Year Built: 2007Year Updated: 2007
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 8999 sqft

Price History for 101 Webb St

DatePriceEventSource
09/30/2020$582,000Sold
Stellar MLS #A4474848
08/17/2020$579,000PendingAgent Provided
08/12/2020$579,000Listed For SaleAgent Provided
08/23/2018$518,000Sold
N/A
07/27/2018$525,000PendingAgent Provided
06/22/2018$525,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$8,395
Assessment$697,700
Home facts updated by county records

Comparable Sales for 101 Webb St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
51 Webb St, Osprey, FL
0.04
Single-Family Home
$570,000
04/03/26
3
2.5
2,130
38 W Bay St, Osprey, FL
0.18
Single-Family Home
$865,000
02/10/26
3
2
2,124
315 Bayshore Dr, Osprey, FL
0.48
Single-Family Home
$527,500
02/27/26
3
3
2,384
240 Patterson Ave, Osprey, FL
0.28
Single-Family Home
$350,000
10/16/25
3
2
1,360
115 Green St, Osprey, FL
0.33
Single-Family Home
$358,000
11/13/25
2
2
1,503
26 Bay Acres Ave, Osprey, FL
0.49
Single-Family Home
$479,000
09/10/25
3
2
1,904
444 Washington Ave, Osprey, FL
0.32
Single-Family Home
$200,000
10/06/25
3
2
1,284
228 Saint James Park, Osprey, FL
0.58
Single-Family Home
$1,600,000
05/14/26
3
2.5
2,425
223 Saint James Park, Osprey, FL
0.54
Single-Family Home
$1,197,000
05/30/25
3
4
3,321
4173 Westbourne Cir, Sarasota, FL
1.05
Single-Family Home
$550,000
08/07/25
3
3
2,116

Assigned Schools

These are the assigned schools for 101 Webb St.
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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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101 Webb St, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,860 sqft single-family home built in 2007. This property is not currently available for sale. 101 Webb St was last sold on Sep 30, 2020 for $582,000. The current Trulia Estimate for 101 Webb St is $796,600.