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.
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
See this Listing
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
- Address244 WOODLAND DRIVE UNIT 244 OSPREY FL
- SubdivisionPINE RUN III
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN POINT MARINA VILLAGE
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- HIDDEN BAY; LAKE VISTA
- LAKE VISTA
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OSPREY EXECUTIVE PARK
- OSPREY PARK 2
- PALMER
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SORRENTO VILLAS 1
- SORRENTO VILLAS 2
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS AT OSPREY HARBOR VILLAGE
- VILLAS AT THE OSPREY HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WEBBS W D ADD
- WILLOWBEND
- WILLOWBEND PH 1
- WILLOWBEND PH 2
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WINDSOR LODGE AT THE OAKS
Market Summary
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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Courtesy of KELLER WILLIAMS ON THE WATER S. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 244 WOODLAND DRIVE UNIT 244
OSPREY, FL















































