Tranquil Coastal Living in Pine Run 244 Woodland Dr, Osprey, FL

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Condo For Sale

244 WOODLAND DRIVE 244

Osprey, Florida 34229

Sarasota County

Community: PINE RUN III

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$225,000 2 br, 2.0 bath 1325 sq. ft. 0.000 acres

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:
o 2 Bedrooms, 2 Bathrooms, 1,325 Sq Ft
o Open, light-filled interior with stylish kitchen and breakfast nook
o Vaulted, wood-ceiling lanai with peaceful treetop views
o Primary suite with private lanai access
o Full laundry, ample storage, and designated carport parking
o Low-maintenance living with exceptional amenities
o Minutes to Nokomis Beach, Casey Key, and downtown Sarasota

Live easy. Breathe deep. Welcome home to Pine Run.

Interior:
  • Bedrooms: 2
  • Baths: 2.0
  • Sq Ft: 1325
  • Year Built: 1980
  • Utilities: 
  • Fireplaces: 
  • Stories: 
  • Heat/AC: Central, Electric (Heating)
  • Garage: Assigned, Guest
Exterior:
  • Lot Size: 0.000 acre
  • Lot Dimensions: 
  • View Types: 
  • Yard: 
  • Siding: Wood Siding
  • Roof: Shingle
  • Property Taxes: $2,907
  • MLS #: A4667419
  • Unit Number: 244
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Contact Information:
Beach Condo For Sale in Osprey, Florida
Listing Agent: Derek Edwards, Keller Williams on the Water Sarasota, 941-803-7522, 941-803-7522 Listing Site, Listing Status: Active
Copyright © 2025 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 6727339
Viewed 36 times.
Updated: Oct 17, 2025

This property is a Condo located at 244 WOODLAND DRIVE 244, Osprey, Florida 34229, and is currently For Sale at $225,000. This Condo has 2 bedrooms, 2.0 baths, 1325 sq ft.