365 Pine Run Dr, Osprey, FL 34229
OFF MARKET

365 Pine Run Dr
Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,223 sqft

$219,000

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $1,404/mo*
Refinance Your Home

$219,000

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $1,404/mo*
Refinance Your Home
2 Beds
2 Baths
1,223 sqft

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

Pine Run's Best Opportunity! Sophisticated loft-style 2/2 townhouse boasts bright, open floor plan & a rain forest view. West of Trail & on the way to Casey Key, Pine Run is a haven for artists & connoisseurs of unusual spaces. Sarasota School of Architecture's Frank Folsom Smith designed the first section here, with condos in this newer building showing his influence. Renovations to this 2nd/3rd level townhouse with soaring ceilings were tastefully & carefully planned with comfort, safety & style in mind. Out with the spiral & in with the traditional staircase; handsome new wooden flooring; updated kitchen with hardwood cabinets & solid surface countertops; master & guest baths done up in light'n bright neutral tones; premium carpeted bedrooms for a luxurious underfoot feel; cypress walk-in MBR closet. A huge, finished storage closet off the loft BR can be put to many uses. Situated snugly away from busy arteries and close to the tennis courts, there is covered carport + guest parking & outdoor storage. With lushly vegetated grounds, 2 heated pools (one geothermal), 4 tennis courts, walking trails, kayak racks, an updated fitness room on the condo Board's list of projects, & a super convenient location, Pine Run continues a tradition of lifestyle enhancement for multiple generations. Ground level furnished 1/1.5 below this unit also available could be joined to create one tri-level home (see MLS #3914478).
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
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Outdoor
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HOA
None
Price/Sqft
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Listed
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Home Details for 365 Pine Run Dr

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Other
Interior Details
Number of Rooms: 5

Exterior Features

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

Property Information

Year Built
Year Built: 1979Year Updated: 1999
Property Type / Style
Property Type: Condo

Community

Units in Building: 1

Price History for 365 Pine Run Dr

DatePriceEventSource
09/13/2013$140,000Sold
N/A
03/19/2010$120,000Sold
N/A
01/09/2010$137,900PriceChange
Agent Provided
12/12/2009$145,000PriceChange
Agent Provided
10/04/2009$159,500Listed For SaleAgent Provided
02/01/2000$70,300Sold
N/A
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Property Tax and Assessment

Year2025
Tax$2,841
Assessment$193,200
Home facts updated by county records

Comparable Sales for 365 Pine Run Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
362 Pine Run Dr, Osprey, FL
0.06
Condo
$215,000
05/01/26
2
2
1,224
201 Woodland Dr #201, Osprey, FL
0.09
Condo
$200,000
12/09/25
2
2
1,316
201 Woodland Dr, Osprey, FL
0.09
Condo
$200,000
12/29/25
2
2
1,316
761 Pine Run Dr, Osprey, FL
0.00
Condo
$260,000
01/23/26
2
2
1,379
216 Woodland Dr #216, Osprey, FL
0.09
Condo
$220,000
10/23/25
2
2
1,325
761 Pine Run Dr #761, Osprey, FL
0.06
Condo
$260,000
01/23/26
2
2
1,379
207 Woodland Dr #207, Osprey, FL
0.09
Condo
$250,000
10/23/25
2
2
1,325
207 Woodland Dr, Osprey, FL
0.09
Condo
$250,000
10/28/25
2
2
1,325
109 Woodland Pl, Osprey, FL
0.16
Condo
$235,000
06/13/25
2
2
1,223
111 Woodland Pl, Osprey, FL
0.16
Condo
$227,000
12/15/25
2
2
1,316

Nearby homes

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Assigned Schools

These are the assigned schools for 365 Pine Run Dr.
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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365 Pine Run Dr, Osprey, FL 34229 is a 2 bedroom, 2 bathroom, 1,223 sqft condo built in 1979. This property is not currently available for sale. 365 Pine Run Dr was last sold on Sep 13, 2013 for $140,000. The current Trulia Estimate for 365 Pine Run Dr is $219,000.