108 Main St, Osprey, FL 34229
OFF MARKET

108 Main St
Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,305 sqft (on 0.34 acres)

$655,100

Trulia Estimate
as of Jun 27, 2026
Est. Refi. Payment $4,012/mo*
Refinance Your Home

$655,100

Trulia Estimate
as of Jun 27, 2026
Est. Refi. Payment $4,012/mo*
Refinance Your Home
3 Beds
2 Baths
2,305 sqft
(on 0.34 acres)

Local Information

  • Map ViewExplore the area around 108 Main St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Just a few houses from the bay, Main Street fishing pier, Spanish Point Restaurant/ Tiki and walking distance to Pine View School. West of the trail. This perfectly maintained 2/3 bedroom pool home on a quite charming street in Osprey. , huge landscape corner lot, oversize 2 car detached garage with workshop/storage room. Steps to Osprey fishing pier, enjoy beautiful sunsets, kayaking, paddle board, fishing ..ect.Florida living. No flood insurance needed.
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, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 108 Main St

Interior Features

Heating & Cooling
Heating: Other, ElectricAir ConditioningCooling System: CentralHeating Fuel: Other
Interior Details
Number of Rooms: 7
Appliances & Utilities
DisposalRefrigerator
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Other

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking Spaces: 4Parking: Carport, Garage Detached

Property Information

Year Built
Year Built: 1980Year Updated: 1980
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.34 acres

Price History for 108 Main St

DatePriceEventSource
03/25/2020$475,000Sold
N/A
02/23/2020$529,000PendingAgent Provided
08/26/2019$529,000Listed For SaleAgent Provided

Market trends in Osprey

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$569K
$30.33KMoM
Sale-to-List Price
—
Price per sq ft
$269
$8MoM
Available listings
156
6MoM
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Property Tax and Assessment

Year2025
Tax$5,351
Assessment$545,700
Home facts updated by county records

Comparable Sales for 108 Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
51 Webb St, Osprey, FL
0.11
Single-Family Home
$570,000
04/03/26
3
2.5
2,130
212 Washington Ave, Osprey, FL
0.20
Single-Family Home
$416,400
04/24/26
3
2
1,478
38 W Bay St, Osprey, FL
0.11
Single-Family Home
$865,000
02/10/26
3
2
2,124
26 Bay Acres Ave, Osprey, FL
0.42
Single-Family Home
$479,000
09/10/25
3
2
1,904
315 Bayshore Dr, Osprey, FL
0.41
Single-Family Home
$527,500
02/27/26
3
3
2,384
32 Bay Ave, Osprey, FL
0.56
Single-Family Home
$400,000
06/05/26
2
2
2,148
240 Patterson Ave, Osprey, FL
0.31
Single-Family Home
$350,000
10/16/25
3
2
1,360
444 Washington Ave, Osprey, FL
0.39
Single-Family Home
$200,000
10/06/25
3
2
1,284
115 Green St, Osprey, FL
0.39
Single-Family Home
$358,000
11/13/25
2
2
1,503
222 Glenwood Ave, Osprey, FL
0.35
Single-Family Home
$300,000
06/15/26
2
2
952

Nearby homes

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Assigned Schools

These are the assigned schools for 108 Main St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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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Apartments for Rent

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Explore by feature - Pet Friendly

9 pet-friendly rentals in Osprey, FL

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

Homes for sale near 108 Main St

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Off Market Homes Near 108 Main St

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108 Main St, Osprey, FL 34229 is a 3 bedroom, 2 bathroom, 2,305 sqft single-family home built in 1980. This property is not currently available for sale. 108 Main St was last sold on Mar 25, 2020 for $475,000. The current Trulia Estimate for 108 Main St is $655,100.