129 Main St, Osprey, FL 34229
Property image
Property image
OFF MARKET

129 Main St
Osprey, FL 34229

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

$2,864,600

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $17,773/mo*
Refinance Your Home

$2,864,600

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $17,773/mo*
Refinance Your Home
5 Beds
5 Baths
3,983 sqft
(on 0.47 acres)

Home Value

Trulia Estimate
$2.87M
Since last month
Increased$39K (+1.4%)
Since last year
Increased$61K (+2.2%)
Since last sale
Increased$1M (+104.2%)
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 +73% in the last 10 years
MonthEstimated value
2026
August 2026$2.88M
July 2026$2.84M
June 2026$2.92M
May 2026$2.89M
April 2026$2.9M
March 2026$2.9M
February 2026$2.86M
January 2026$2.79M
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
140 SUGAR MILL DRIVE, Osprey, FL
0.41
Single-Family Home
$1,325,000
06/16/26
4
4
3,286
67 SUGAR MILL DRIVE, Osprey, FL
0.52
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
370 SUGAR MILL DRIVE, Osprey, FL
0.58
Single-Family Home
$2,189,000
02/09/26
5
5.5
4,783
324 BAYSHORE DRIVE, Osprey, FL
0.48
Single-Family Home
$3,650,000
08/24/26
4
4.5
4,389
76 OSPREY POINT DRIVE, Osprey, FL
0.68
Single-Family Home
$1,450,000
06/15/26
3
4.5
4,364
25 SUGAR MILL DRIVE, Osprey, FL
0.63
Single-Family Home
$1,300,000
07/22/26
3
3.5
3,066
325 OSPREY POINT DRIVE, Osprey, FL
0.82
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
51 WEBB STREET, Osprey, FL
0.24
Single-Family Home
$570,000
04/03/26
3
2.5
2,130
133 Osprey Point Dr, Osprey, FL
0.89
Single-Family Home
$1,054,284
06/29/26
4
3
4,099
38 W BAY STREET, Osprey, FL
0.25
Single-Family Home
$865,000
02/10/26
3
2
2,124

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
133 W BAY STREET, Osprey, FL 34229
0.18
$1,955,000
4
4
3,168
Off Market
133 W BAY STREET LOT 1, Osprey, FL 34229
0.18
-
-
-
-
Off Market
162 PUESTA DEL SOL, Osprey, FL 34229
0.19
$2,336,600
4
4.5
4,747
Off Market
3820 PARROT BAY COURT LOT 9, Osprey, FL 34229
0.22
$825,000
-
-
-
For Sale
38 W BAY STREET, Osprey, FL 34229
0.25
$865,000
3
2
2,124
Recently Sold
110 PINE AVENUE, Osprey, FL 34229
0.25
$649,000
3
2
2,058
For Sale
51 WEBB STREET, Osprey, FL 34229
0.24
$570,000
3
2.5
2,130
Recently Sold
236 HIDDEN BAY DRIVE #301, Osprey, FL 34229
0.31
$623,400
3
3
2,100
Off Market
236 HIDDEN BAY DRIVE #504, Osprey, FL 34229
0.31
$831,500
3
3
2,100
Off Market
242 HIDDEN BAY DRIVE #304, Osprey, FL 34229
0.31
$787,000
3
3
2,100
Off Market
242 HIDDEN BAY DRIVE #401, Osprey, FL 34229
0.31
$800,000
3
3
2,100
Recently Sold
242 HIDDEN BAY DRIVE #403, Osprey, FL 34229
0.31
$572,600
2
2
1,932
Off Market

Local Information

  • Map ViewExplore the area around 129 Main 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
1999
Lot Size
0.47 acres
Living Area
3,983 sqft
Price/Sqft
$719
Parking
Garage

About this House

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.
129 Main St, Osprey, FL 34229 is a 5 bedroom, 5 bathroom, 3,983 sqft single-family home built in 1999. It last sold for $1,412,500 on Oct 1, 2014. It is currently off market. The Trulia Estimate is $2,864,600, with a rent estimate of $6,467/month.

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 and Tax history

DateEventPrice
Oct 1, 2014
Source: N/A
Sold
$1,412,500
Jun 4, 2014
Source: Agent Provided
PriceChange
$1,554,000
Price decreased by 9%
Nov 15, 2013
Source: Agent Provided
PriceChange
$1,699,000
Price decreased by 6%
Mar 9, 2013
Source: Agent Provided
Listed For Sale
$1,799,000

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

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

LGBTQ Local Legal Protections

Frequently asked questions about 129 Main St

  • What is 129 Main St estimated to be worth?
    Trulia's estimated value for 129 Main St in Osprey, FL is $2,864,600.
  • What is the price history for 129 Main St?
    129 Main St in Osprey, FL last sold for $1,412,500 in October 2014.
  • What are the closest schools to 129 Main St?
    The closest schools to 129 Main St in Osprey, FL are Laurel Nokomis School (Pre-K/Elementary/Middle, rated 8/10), Venice Senior High School (rated 7/10).
  • Does 129 Main St have air conditioning?
    Yes, 129 Main St in Osprey, FL has air conditioning.
  • Does 129 Main St have a pool?
    Yes, 129 Main St in Osprey, FL has a pool.
  • How big is the lot at 129 Main St?
    The lot at 129 Main St in Osprey, FL is about 0.47 acres (20,473 sq ft).

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