244 WOODLAND DRIVE UNIT 244 OSPREY FL 34229 MLS #A4667419

244 WOODLAND DRIVE UNIT 244
OSPREY, FL, 34229
$200,000
2 Beds
2 Baths
1,325 SqFt
0 Acres
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MLS #A4667419 image #0
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.

Property Details

Price:
$200,000
MLS #:
A4667419
Status:
Active
Beds:
2
Baths:
2
Type:
Condo
Subtype:
Condominium
Subdivision:
PINE RUN III
Neighborhood:
34229osprey
Listed Date:
Oct 16, 2025
Finished Sq Ft:
1,325
Total Sq Ft:
1,483
Year Built:
1980
PoolTennisCommunity Club House34229 – Osprey34229ospreyPine Run IiiBuyer And Buyer’s Agent To Verify All Restrictions With The Condo Association. No More Than 25% Of Units May Be Leased At A Time. Please Visit Website: Www.pinerunosprey.org For More Leasing Info.1 MonthPets Allowed

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Schools

Interior

Appliances
Dishwasher, Dryer, Electric Water Heater, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Tile
Heating
Central, Electric
Laundry Features
Inside, Laundry Closet

Exterior

Association Amenities
Clubhouse, Fitness Center, Pool, Recreation Facilities, Tennis Court(s)
Community Features
Buyer Approval Required, Clubhouse, Community Mailbox, Fitness Center, Golf Carts OK, Pool, Tennis Court(s)
Construction Materials
Wood Siding
Exterior Features
Sliding Doors
Parking Features
Assigned, Guest
Roof
Shingle

Financial

HOA Includes
Community Pool, Escrow Reserves Fund, Maintenance Structure, Maintenance Grounds, Manager, Pool Maintenance, Recreational Facilities, Sewer, Trash, Water
HOA Name
Pine Run III/Keys Caldwell
Tax Year
2025
Taxes
$2,685

Map

Community

Market Summary

Current real estate data for Condo in OSPREY as of Mar 20, 2026
49
Condo Listed
164
Avg DOM
325
Avg $ / SqFt
$725,579
Avg List Price

Property Summary

    Located in the PINE RUN III subdivision, 244 WOODLAND DRIVE UNIT 244 OSPREY FL is a Condo for sale in OSPREY, FL, 34229. It is listed for $200,000 and features 2 beds, 2 baths, and has approximately 1,325 square feet of living space, and was originally constructed in 1980. The current price per square foot is $151. The average price per square foot for Condo listings in OSPREY is $325. The average listing price for Condo in OSPREY is $725,579. To schedule a showing of MLS#a4667419 at 244 WOODLAND DRIVE UNIT 244 in OSPREY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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244 WOODLAND DRIVE UNIT 244
OSPREY, FL