Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$200,000 -$15,000 (-6.98%) Price Reduced

  • For Sale
  • Active
  • Condo
  • 2 Beds
  • 2 Full Baths
  • 1,325 Sq. Ft.
  • Updated 2 days ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Saturday 3/7 11:00 AM - 1:00 PM

244 Woodland Drive #244,Osprey, FL 34229

244 Woodland Drive #244OspreyFL34229

Get directions
See This Home
Save This Home
See This Home
Save This Home
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: $200,000
  • HOA FEE: $840/month
  • Taxes: $2,685 (2025)
  • Status: Active
  • Type: Condo
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4667419
  • Updated: 3/2/2026
  • Added to Site: 140 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

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 244 Woodland Dr #244 —

  • Keller Williams On The Water S

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

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
3/02/2026
Price Reduced
$200,000
-6.98%
MLS
1/21/2026
Price Reduced
$215,000
-4.44%
MLS
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.

Estimate the Cost for 244 Woodland Dr #244

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Keller Williams On The Water S

Similar Properties near 244 Woodland Dr #244

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

211 Woodland Dr, Osprey, FL 34229 - Photo 1 Just Listed
$200,000

211 Woodland Dr  #211  Osprey, FL 34229

  • Condo
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,223
    Sq. Ft.
Listed by Better Homes and Gardens Real Estate Atchley Prope
354 Pine Run Dr, Osprey, FL 34229 - Photo 1
$200,000

354 Pine Run Dr  Osprey, FL 34229

  • Condo
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,224
    Sq. Ft.
Listed by Compass Florida Llc
800 Capri Isles Blvd, Venice, FL 34292 - Photo 1
$200,000

800 Capri Isles Blvd  #236  Venice, FL 34292

  • Condo
  • Active
  • 2
    Beds
  • 2
    Total Baths
  • 1,350
    Sq. Ft.
Listed by Gulf Shores Realty
2220 Stickney Point Rd, Sarasota, FL 34231 - Photo 1
$199,999

2220 Stickney Point Rd  #531  Sarasota, FL 34231

  • Condo
  • Active
  • 2
    Beds
  • 2
    Total Baths
  • 951
    Sq. Ft.
Listed by Offermate Real Estate

Just Listed near 244 Woodland Dr #244

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1062 Ancora Blvd, North Venice, FL 34275 - Photo 1 Just Listed
$699,000

1062 Ancora Blvd  North Venice, FL 34275

  • Single Family
  • Active
  • Updated 15 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,676
    Sq. Ft.
Listed by Frank Zeckel (941) 284-4732
N/A Ranch Rd, North Venice, FL 34275 - Photo 1 Just Listed
$1,595,000

N/A Ranch Rd  North Venice, FL 34275

  • Business
  • Active
Listed by Bright Realty
496 Bocelli Dr, North Venice, FL 34275 - Photo 1 Just Listed
$899,000

496 Bocelli Dr  North Venice, FL 34275

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,455
    Sq. Ft.
Listed by Charles Rutenberg Realty Inc
157 Treviso Ct, North Venice, FL 34275 - Photo 1 Just Listed
$499,000

157 Treviso Ct  North Venice, FL 34275

  • Single Family
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,863
    Sq. Ft.
Listed by Homesmart

Price Reduced near 244 Woodland Dr #244

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

225 Pesaro Dr, North Venice, FL 34275 - Photo 1 Price Reduced
-$50,000 (-4.65%)
$1,025,000
Open House

225 Pesaro Dr  North Venice, FL 34275

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 3,136
    Sq. Ft.
Listed by Liz Carvalho (941) 800-8188
225 Mestre Pl, North Venice, FL 34275 - Photo 1 Price Reduced
-$17,000 (-3.96%)
$412,000

225 Mestre Pl  North Venice, FL 34275

  • Single Family
  • Active
  • Updated 2 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,653
    Sq. Ft.
Listed by Engel + Voelkers Sarasota
118 Caneletto Way, North Venice, FL 34275 - Photo 1 Price Reduced
-$25,100 (-3.04%)
$799,900

118 Caneletto Way  North Venice, FL 34275

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,528
    Sq. Ft.
Listed by Premier Sothebys Intl Realty
129 Treviso Ct, North Venice, FL 34275 - Photo 1 Price Reduced
-$10,000 (-1.96%)
$499,000
Open House

129 Treviso Ct  North Venice, FL 34275

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,485
    Sq. Ft.
Listed by Flat Fee Mls Realty

Recent Sales near 244 Woodland Dr #244

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

216 Woodland Dr, Osprey, FL 34229 - Photo 1 Sold
$220,000

216 Woodland Dr  #216  Osprey, FL 34229

  • Condo
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,325
    Sq. Ft.
Listed by Pat Williams Realty, Llc
Sold by White Sands Paradise Realty
201 Woodland Dr, Osprey, FL 34229 - Photo 1 Sold
$200,000

201 Woodland Dr  #201  Osprey, FL 34229

  • Condo
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,316
    Sq. Ft.
Listed by Preferred Properties Of Venice Inc
Sold by Compass Florida Llc
226 Woodland Dr, Osprey, FL 34229 - Photo 1 Sold
$200,000

226 Woodland Dr  Osprey, FL 34229

  • Condo
  • Closed
  • 1
    Bed
  • 2
    Total Baths
  • 865
    Sq. Ft.
Listed by Stellar Non-Member Office
Sold by Compass Florida Llc and Kellie MacDonell
111 Woodland Pl, Osprey, FL 34229 - Photo 1 Sold
$227,000

111 Woodland Pl  Osprey, FL 34229

  • Condo
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,316
    Sq. Ft.
Listed by Compass Florida Llc
Sold by Preferred Shore Llc

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 $200,000 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.

Tour this property