244 WOODLAND DRIVE
OSPREY, FL, 34229
Price$200,000
Beds2
Baths2
SqFt1,325
Baths2
SqFt1,325
Status:Active
Property Type:Residential
School:
Property Type:Residential
School:
Tranquil Coastal Living in Pine Run
244 Woodland Dr, Osprey, FL 34229
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.
| Price | $200,000 | |
| Bedrooms | 2 | |
| Full Baths | 2 | |
| Half Baths | 0 | |
| Total Baths | 2 | |
| Acres | 0 | |
| Property Type | Residential | |
| Sub type | Condominium | |
| MLS Sub type | Condominium | |
| Features | Ceiling Fan(s) | |
| Exterior Features | Sliding Doors | |
| Year Built | 1980 | |
| Subdivision | PINE RUN III | |
| Roof | Shingle | |
| Heating | Central, Electric | |
| Foundation | Slab | |
| Laundry Features | Inside, Laundry Closet | |
| Parking Description | Assigned, Guest | |
| Association Name | Pine Run III/Keys Caldwell | |
| Association Amenities | Clubhouse, Fitness Center, Pool, Recreation Facilities, Tennis Court(s) | |
| 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 | |
| County | Sarasota | |
| Latitude | 27.181514 | |
| Longitude | -82.484805 | |
| Market Area | 34229 – Osprey | |
| Address | 244 WOODLAND DRIVE #244, OSPREY, FL 34229 | |
| Unit | 244 | |
| Postal Code | 34229 | |
| City | OSPREY | |
| State | FL | |
| Country | United States | |
| Listing Office | KELLER WILLIAMS ON THE WATER S | |
| Listing Office Phone | 941-803-7522 | |
| Listing Agent | Derek Edwards | |
| Listing Agent Phone | 941-929-3183 | |
| Special listing conditions | None | |
| Ownership | Condominium | |
| Terms | Cash, Conventional | |
| Virtual Tour URL | https://www.propertypanorama.com/instaview/stellar/A4667419 | |
| Days on market | 142 | |
| MLS Status | Active | |
| Listing Date | Oct 16, 2025 | |
| Listing Last Modified | Mar 7, 2026 | |
| Tax ID | 0157012043 | |
| Tax Year | 2025 | |
| Tax Annual Amount | 2685 | |
| MLS Area | 34229 – Osprey | |
| MLS # | A4667419 | |
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