366 Pine Run Dr, Osprey, FL 34229
Property image
Property image
OFF MARKET

366 Pine Run Dr
Osprey, FL 34229

  • 1 Bed
  • 1 Bath
  • 586 sqft

$162,600

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $1,076/mo*
Refinance Your Home

$162,600

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $1,076/mo*
Refinance Your Home
1 Bed
1 Bath
586 sqft

Home Value

Trulia Estimate
$163K
Since last month
Decreased$6K (-3.3%)
Since last year
Decreased$13K (-7.5%)
Since last sale
Decreased$59K (-26.7%)
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 +85% in the last 10 years
MonthEstimated value
2026
August 2026$162K
July 2026$162K
June 2026$168K
May 2026$167K
April 2026$166K
March 2026$165K
February 2026$169K
January 2026$168K
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
226 WOODLAND DRIVE, Osprey, FL
0.09
Condo
$200,000
11/24/25
1
1.5
865
238 Woodland Dr, Osprey, FL
0.09
Condo
$170,000
03/16/26
1
1.5
865
238 WOODLAND DRIVE #238, Osprey, FL
0.09
Condo
$170,000
03/10/26
1
1.5
865
200 WOODLAND DRIVE, Osprey, FL
0.09
Condo
$164,000
05/14/26
1
1.5
865
139 WOODLAND PLACE #139, Osprey, FL
0.20
Condo
$235,000
02/12/26
1
1.5
865
200 Woodland Dr #200, Osprey, FL
0.09
Condo
$164,000
05/27/26
2
2
865
362 PINE RUN DRIVE, Osprey, FL
0.06
Condo
$215,000
05/01/26
2
2
1,224
761 Pine Run Dr, Osprey, FL
0.00
Condo
$260,000
01/23/26
2
2
1,379
216 WOODLAND DRIVE #216, Osprey, FL
0.09
Condo
$220,000
10/23/25
2
2
1,325
201 Woodland Dr, Osprey, FL
0.09
Condo
$200,000
12/29/25
2
2
1,316

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
360 PINE RUN DRIVE, Osprey, FL 34229
0.06
$251,500
2
2
1,379
Off Market
362 PINE RUN DRIVE, Osprey, FL 34229
0.06
$215,000
2
2
1,224
Recently Sold
750 PINE RUN DRIVE, Osprey, FL 34229
0.06
$129,200
1
1
586
Off Market
756 PINE RUN DRIVE, Osprey, FL 34229
0.06
$263,900
2
2
1,224
Off Market
760 PINE RUN DRIVE, Osprey, FL 34229
0.06
$120,000
1
1
586
Off Market
767 PINE RUN DRIVE, Osprey, FL 34229
0.06
$147,100
1
1
736
Off Market
707 PINE RUN DRIVE, Osprey, FL 34229
0.06
$269,000
2
2
1,379
Recently Sold
751 PINE RUN DRIVE #751, Osprey, FL 34229
0.06
$117,600
1
1
586
Off Market
701 PINE RUN DRIVE #701, Osprey, FL 34229
0.06
$172,000
1
1
586
For Sale
761 PINE RUN DRIVE #761, Osprey, FL 34229
0.06
$260,000
2
2
1,379
Recently Sold
216 WOODLAND DRIVE #216, Osprey, FL 34229
0.09
$220,000
2
2
1,325
Recently Sold
226 WOODLAND DRIVE, Osprey, FL 34229
0.09
$200,000
1
1.5
865
Recently Sold

Local Information

  • Map ViewExplore the area around 366 Pine Run Dr.
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
1973
Living Area
586 sqft
Price/Sqft
$277

About this House

Light bright and airy! High ceilings, tile throughout, freshly painted, new granite counters, new kitchen sink, new built-in located in the living room, new washer/dryer in unit, updated bathroom with walk in shower & tankless water heater. Newly screened 3 lanais allow for terrific cross breezes. Complex offers Tennis, 2 heated pools, clubhouse, fitness center, kayak storage & more. Great location close to Blackburn Park with boat/kayak launch, Casey Key Fish house, shopping, banking & restaurants. Ideal for a full time resident or 2nd home. Fee includes roof which was replaced less than a year ago. Pet friendly complex too. Seller has a plan to build storage area under the steps which was approved by the association if buyer chooses to add it.
366 Pine Run Dr, Osprey, FL 34229 is a 1 bedroom, 1 bathroom, 586 sqft condo built in 1973. It last sold for $221,000 on Aug 16, 2022. It is currently off market. The Trulia Estimate is $162,600, with a rent estimate of $1,493/month.

Home Details for 366 Pine Run Dr

Interior Features

Heating & Cooling
Heating: Central, ElectricAir ConditioningCooling System: CentralHeating Fuel: Central
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile
Interior Details
Number of Rooms: 3
Appliances & Utilities
DishwasherMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: OtherFoundation Type: Concrete
Parking & Garage
Parking: Open

Property Information

Year Built
Year Built: 1973Year Updated: 1978
Property Type / Style
Property Type: CondoArchitecture: Contemporary

Community

Units in Building: 1

Price and Tax history

DateEventPrice
Aug 16, 2022
Source: N/A
Sold
$221,000
Jul 29, 2022
Source: Stellar MLS #A4542940
Pending
$209,900
Jul 25, 2022
Source: Stellar MLS #A4542940
Listed For Sale
$209,900
Feb 10, 2021
Source: N/A
Sold
$145,000
Feb 18, 2020
Source: N/A
Sold
$125,000

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 366 Pine Run Dr

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Off Market Homes Near 366 Pine Run Dr

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Frequently asked questions about 366 Pine Run Dr

  • What is 366 Pine Run Dr estimated to be worth?
    Trulia's estimated value for 366 Pine Run Dr in Osprey, FL is $162,600.
  • What is the price history for 366 Pine Run Dr?
    366 Pine Run Dr in Osprey, FL last sold for $221,000 in August 2022.
  • 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 366 Pine Run Dr have air conditioning?
    Yes, 366 Pine Run Dr in Osprey, FL has air conditioning.
  • Does 366 Pine Run Dr have parking?
    Yes, 366 Pine Run Dr in Osprey, FL has on-site parking.