101 Webb St, Osprey, FL 34229
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Property image
OFF MARKET

101 Webb St
Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,860 sqft

$797,800

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $4,970/mo*
Refinance Your Home

$797,800

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $4,970/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,860 sqft

Home Value

Trulia Estimate
$798K
Since last month
Decreased$16K (-2%)
Since last year
Increased$16K (+2.1%)
Since last sale
Increased$213K (+36.5%)
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 +50% in the last 10 years
MonthEstimated value
2026
August 2026$795K
July 2026$792K
June 2026$811K
May 2026$800K
April 2026$799K
March 2026$797K
February 2026$800K
January 2026$785K
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
0.04
Single-Family Home
$570,000
04/03/26
3
2.5
2,130
38 W BAY STREET, Osprey, FL
0.18
Single-Family Home
$865,000
02/10/26
3
2
2,124
212 WASHINGTON AVENUE, Osprey, FL
0.16
Single-Family Home
$416,400
04/24/26
3
2
1,478
315 BAYSHORE DRIVE, Osprey, FL
0.48
Single-Family Home
$527,500
02/27/26
3
3
2,384
240 PATTERSON AVENUE, Osprey, FL
0.28
Single-Family Home
$350,000
10/16/25
3
2
1,360
115 GREEN STREET, Osprey, FL
0.33
Single-Family Home
$358,000
11/13/25
2
2
1,503
26 BAY ACRES AVENUE, Osprey, FL
0.49
Single-Family Home
$479,000
09/10/25
3
2
1,904
140 SUGAR MILL DRIVE, Osprey, FL
0.30
Single-Family Home
$1,325,000
06/16/26
4
4
3,286
444 WASHINGTON AVENUE, Osprey, FL
0.32
Single-Family Home
$200,000
10/06/25
3
2
1,284
222 GLENWOOD AVENUE, Osprey, FL
0.32
Single-Family Home
$300,000
06/15/26
2
2
952

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
0.04
$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
0.08
$649,000
3
2
2,058
For Sale
3820 PARROT BAY COURT LOT 9, Osprey, FL 34229
0.15
$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
0.18
$865,000
3
2
2,124
Recently Sold
242 WASHINGTON AVENUE, Osprey, FL 34229
0.18
$181,800
2
1
630
Off Market
133 W BAY STREET, Osprey, FL 34229
0.22
$1,936,700
4
4
3,168
Off Market
133 W BAY STREET LOT 1, Osprey, FL 34229
0.22
-
-
-
-
Off Market
34 WASHINGTON AVENUE LOT 67, Osprey, FL 34229
0.22
$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 101 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
2007
Living Area
2,860 sqft
Price/Sqft
$279
Parking
Garage

About this House

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!
101 Webb St, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,860 sqft single-family home built in 2007. It last sold for $582,000 on Sep 30, 2020. It is currently off market. The Trulia Estimate is $797,800, with a rent estimate of $4,796/month.

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 and Tax history

DateEventPrice
Sep 30, 2020
Source: Stellar MLS #A4474848
Sold
$582,000
Aug 17, 2020
Source: Agent Provided
Pending
$579,000
Aug 12, 2020
Source: Agent Provided
Listed For Sale
$579,000
Aug 23, 2018
Source: N/A
Sold
$518,000
Jul 27, 2018
Source: Agent Provided
Pending
$525,000

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 101 Webb St

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Off Market Homes Near 101 Webb St

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Frequently asked questions about 101 Webb St

  • What is 101 Webb St estimated to be worth?
    Trulia's estimated value for 101 Webb St in Osprey, FL is $797,800.
  • What is the price history for 101 Webb St?
    101 Webb St in Osprey, FL last sold for $582,000 in September 2020.
  • 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 101 Webb St have air conditioning?
    Yes, 101 Webb St in Osprey, FL has air conditioning.
  • Does 101 Webb St have a pool?
    Yes, 101 Webb St in Osprey, FL has a pool.