129 Main St, Osprey, FL 34229
OFF MARKET

129 Main St
Osprey, FL 34229

  • 5 Beds
  • 5 Baths
  • 3,983 sqft (on 0.47 acres)

$2,890,900

Trulia Estimate
as of May 26, 2026
Est. Refi. Payment $17,662/mo*
Refinance Your Home

$2,890,900

Trulia Estimate
as of May 26, 2026
Est. Refi. Payment $17,662/mo*
Refinance Your Home
5 Beds
5 Baths
3,983 sqft
(on 0.47 acres)

Local Information

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

Description

WATERFRONT PERFECTION can be found in this custom built pool home with over 106 ft. of Sarasota Bay and Intracoastal Waterway frontage. This 5 possible 6 bedroom open plan leads to inviting outdoor living spaces with fabulous panoramic water views. Located on the wider part of the bay, the boat dock affords easy access to the ICW and Gulf of Mexico. Numerous custom features include teak and cherry hardwood flooring, custom raised panel cabinetry, granite counters, stainless appliances, gas burner stove top, coffered ceilings, Bermuda shutters, and two fireplaces. Dramatic sunsets viewed from EVERY room, high end appointments and finishes, and the private tranquil enclave setting provides the true joy of Florida living. Very close proximity to Pine View School and minutes to shopping, dining, and the renowned powdery white sands of the Sarasota beaches make this an ideal location for your Florida lifestyle.
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
No Info

Home Details for 129 Main St

Interior Features

Heating & Cooling
Heating: CentralAir ConditioningCooling System: CentralHeating Fuel: Central
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile
Interior Details
Number of Rooms: 10
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: OtherExterior: StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking: Garage, Open

Property Information

Year Built
Year Built: 1999Year Updated: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.47 acres

Price History for 129 Main St

DatePriceEventSource
10/01/2014$1,412,500Sold
N/A
06/04/2014$1,554,000PriceChange
Agent Provided
11/15/2013$1,699,000PriceChange
Agent Provided
03/09/2013$1,799,000Listed For SaleAgent Provided
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$23,874
Assessment$1,980,900
Home facts updated by county records

Comparable Sales for 129 Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
67 Sugar Mill Dr, Osprey, FL
0.52
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
370 Sugar Mill Dr, Osprey, FL
0.58
Single-Family Home
$2,189,000
02/09/26
5
5.5
4,783
325 Osprey Point Dr, Osprey, FL
0.82
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
223 Saint James Park, Osprey, FL
0.78
Single-Family Home
$1,197,000
05/30/25
3
4
3,321
282 Shell Midden Ct, Osprey, FL
0.93
Single-Family Home
$1,405,000
07/11/25
3
4.5
3,699
51 Webb St, Osprey, FL
0.24
Single-Family Home
$570,000
04/03/26
3
2.5
2,130
38 W Bay St, Osprey, FL
0.25
Single-Family Home
$865,000
02/10/26
3
2
2,124
315 Bayshore Dr, Osprey, FL
0.46
Single-Family Home
$527,500
02/27/26
3
3
2,384
340 Osprey Point Dr, Osprey, FL
0.84
Single-Family Home
$1,900,000
02/10/26
5
6
6,001
402 Walls Way, Osprey, FL
1.03
Single-Family Home
$1,325,000
11/07/25
4
3.5
3,464

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 129 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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Homes for sale near 129 Main St

Skip to last item
Skip to first item

Off Market Homes Near 129 Main St

Skip to last item
Skip to first item

Homes for rent near 129 Main St

Skip to last item
Skip to first item
129 Main St, Osprey, FL 34229 is a 5 bedroom, 5 bathroom, 3,983 sqft single-family home built in 1999. This property is not currently available for sale. 129 Main St was last sold on Oct 1, 2014 for $1,412,500. The current Trulia Estimate for 129 Main St is $2,890,900.