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$225,000

  • For Sale
  • Active
  • Condo
  • 2 Beds
  • 2 Full Baths
  • 1,325 Sq. Ft.
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Tranquil Coastal Living in Pine Run 244 Woodland Dr, Osprey, FL 34229 Tucked beneath a canopy of mature oaks and palms, this beautifully updated 2-bedroom, 2-bath condo captures the easy, natural rhythm of coastal Florida living. Nestled within the sought-after Pine Run community, it offers both peace and connection just minutes from the beaches of Casey Key, charming Venice, and downtown Sarasota. Step inside to discover light-filled spaces, a warm neutral palette, and a welcoming open layout. The kitchen stands out with stainless-steel appliances, a stylish glass backsplash, and playful custom cabinetry that adds personality and character. A cozy breakfast nook sits beside a large window overlooking lush greenery, creating the perfect spot to start your day. The spacious living and dining areas flow naturally toward a screened lanai with vaulted wood ceilings, where you can sip coffee in the morning or unwind at sunset to the sounds of nature. Both bedrooms are roomy and inviting, with the primary suite opening directly to the lanai for that indoor-outdoor lifestyle Florida is famous for. Pine Run offers resort-style amenities in a natural, park-like setting two heated pools, tennis and pickleball courts, a fitness center, clubhouse, and kayak storage. With 20+ acres of native trees, walking trails, and tropical landscaping, this community feels worlds away yet sits moments from Tamiami Trail, dining, marinas, and the Gulf's turquoise waters. Highlights: "¢ 2 Bedrooms, 2 Bathrooms, 1,325 Sq Ft "¢ Open, light-filled interior with stylish kitchen and breakfast nook "¢ Vaulted, wood-ceiling lanai with peaceful treetop views "¢ Primary suite with private lanai access "¢ Full laundry, ample storage, and designated carport parking "¢ Low-maintenance living with exceptional amenities "¢ Minutes to Nokomis Beach, Casey Key, and downtown Sarasota Live easy. Breathe deep. Welcome home to Pine Run.

Full Property Details for 244 Woodland Dr #244

General

  • Price: $225,000
  • HOA FEE: $840/month
  • Taxes: $2,685 (2025)
  • Status: Active
  • Type: Condo
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4667419
  • Updated: 12/9/2025
  • Added to Site: 94 day(s) ago

Rental Information

  • Min. Lease: 1 Month

Interior

  • Number of Rooms: 4
  • Interior Features: Ceiling Fan(s)
  • Appliances: Dishwasher, Dryer, Electric Water Heater, Range, Refrigerator, Washer
  • Furnishings: Furnished
  • Flooring: Carpet, Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Inside, Laundry Closet

Additional Information

  • Shared Amenities: Clubhouse, Fitness Center, Pool, Recreation Facilities, Tennis Court(s)

Exterior

  • Exterior Features: Sliding Doors

Parking

  • Parking Features: Assigned, Guest

Location

  • Area: 34229 - Osprey
  • County: Sarasota
  • Development Name: 34229 - Osprey
  • Subdivision: PINE RUN III
  • Driving Directions: Head south on I-75 S, Use the right 2 lanes to take exit 200 for FL-681 S toward Venice/Osprey, Continue onto FL-681, Slight right to merge onto US-41 N/N Tamiami Trl toward Osprey, Turn left onto Blackburn Point Rd, Turn right onto Woodland Dr, Home will be on the left
  • Direction Faces: West

Community

  • Community Name: 34229 - Osprey
  • Community Features: Buyer Approval Required, Clubhouse, Community Mailbox, Fitness Center, Golf Carts OK, Pool, Tennis Court(s)
  • Optional Amenities: Clubhouse, Fitness Center, Pool, Recreation Facilities, Tennis Court(s)
  • Assoc. Name: Pine Run III/Keys Caldwell
  • Assoc. Fees Include: Community Pool, Escrow Reserves Fund, Maintenance Structure, Maintenance Grounds, Manager, Pool Maintenance, Recreational Facilities, Sewer, Trash, Water
  • Number of Pets: 2
  • Pet Restrictions: Buyer and Buyer's Agent to verify all restrictions with the Condo Association

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Phone Available, Public, Sewer Connected, Water Connected

Structural Information

  • Exterior Const.: Wood Siding
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,325
  • Sq. Ft. Source: Public Records
  • Year Built: 1980

Lot Features

  • Street/Road Desc.: Asphalt

Financial Considerations

  • Condo Fee: $840
  • Condo Fee Freq: Monthly
  • Tax Amount: $2,685.2
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Condominium
  • Special Conditions: None
  • Legal Description: UNIT 244 PINE RUN SEC 3
  • Flood Zone Info: X
  • APN: 157012043
  • Property ID: 157012043

Listed by Keller Williams On The Water S

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— 244 Woodland Dr #244 —

  • Keller Williams On The Water S

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 244 Woodland Dr #244

School District:Sarasota County School District
NameGradesDistance
Laurel Nokomis School
1900 Laurel Road East, Nokomis, FL 34275
PK-84.8 mi
Venice Senior High School
1 Indian Avenue, Venice, FL 34285
9-126.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 244 Woodland Dr #244 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/16/2025
Listed
$225,000
8.96%
MLS
3/09/2021
Sold
$206,500
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 244 Woodland Dr #244

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,166
-25%
$188,800
-8%
2024
$2,907
-9%
$204,400
-13%
2023
$3,190
39%
$233,900
52%
2021
$2,302
-21%
$154,200
-27%
2022
$2,927
27%
$210,800
53%
2021
$2,302
15%
$137,800
6%
2019
$2,008
3%
$130,200
3%
2018
$1,941
-2%
$126,500
-1%
2017
$1,971
1%
$128,400
-1%
2016
$1,961
10%
$129,600
26%
2015
$1,786
4%
$102,729
10%
2014
$1,720
13%
$93,390
10%
2013
$1,528
—
$84,900
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Keller Williams On The Water S

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244 Woodland Drive #244, Osprey, FL 34229 (MLS# A4667419) is a Condo property with 2 bedrooms and 2 full bathrooms. 244 Woodland Drive #244 is currently listed for $225,000 and was received on October 16, 2025. Want to learn more about 244 Woodland Drive #244? Do you have questions about finding other Condo real estate for sale in Osprey? You can browse all Osprey real estate or contact a Coldwell Banker agent to request more information.

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