244 Woodland Dr Unit 244 Osprey, FL 34229
Estimated payment $2,248/month
Highlights
- Fitness Center
- Clubhouse
- Community Pool
- Laurel Nokomis School Rated A-
- Furnished
- Tennis Courts
About 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.
Listing Agent
KELLER WILLIAMS ON THE WATER S Brokerage Phone: 941-803-7522 License #3363878 Listed on: 10/16/2025
Property Details
Home Type
- Condominium
Est. Annual Taxes
- $2,685
Year Built
- Built in 1980
Lot Details
- West Facing Home
HOA Fees
- $840 Monthly HOA Fees
Home Design
- Entry on the 2nd floor
- Slab Foundation
- Shingle Roof
- Wood Siding
Interior Spaces
- 1,325 Sq Ft Home
- 2-Story Property
- Furnished
- Ceiling Fan
- Sliding Doors
- Living Room
Kitchen
- Range
- Dishwasher
Flooring
- Carpet
- Tile
Bedrooms and Bathrooms
- 2 Bedrooms
- En-Suite Bathroom
- 2 Full Bathrooms
Laundry
- Laundry closet
- Dryer
- Washer
Parking
- Guest Parking
- Assigned Parking
Utilities
- Central Heating and Cooling System
- Electric Water Heater
- High Speed Internet
- Phone Available
- Cable TV Available
Listing and Financial Details
- Visit Down Payment Resource Website
- Tax Lot 104
- Assessor Parcel Number 0157012043
Community Details
Overview
- Association fees include pool, escrow reserves fund, maintenance structure, ground maintenance, management, recreational facilities, sewer, trash, water
- Pine Run Iii/Keys Caldwell Association, Phone Number (941) 408-8293
- Visit Association Website
- Pine Run Community
- Pine Run III Subdivision
- The community has rules related to allowable golf cart usage in the community
Amenities
- Clubhouse
- Community Mailbox
Recreation
- Tennis Courts
- Recreation Facilities
- Fitness Center
- Community Pool
Pet Policy
- 2 Pets Allowed
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $2,907 | $188,800 | -- | $188,800 |
| 2024 | $3,190 | $204,400 | -- | $204,400 |
| 2023 | $3,190 | $233,900 | $0 | $233,900 |
| 2022 | $2,927 | $210,800 | $0 | $210,800 |
| 2021 | $2,302 | $154,200 | $0 | $154,200 |
| 2020 | $2,139 | $137,800 | $0 | $137,800 |
| 2019 | $2,008 | $130,200 | $0 | $130,200 |
| 2018 | $1,941 | $126,500 | $0 | $126,500 |
| 2017 | $1,971 | $124,302 | $0 | $0 |
| 2016 | $1,961 | $129,600 | $0 | $129,600 |
| 2015 | $1,786 | $108,600 | $0 | $108,600 |
| 2014 | $1,720 | $84,900 | $0 | $0 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 10/16/2025 10/16/25 | For Sale | $225,000 | -- | $170 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Interfamily Deed Transfer | -- | Attorney | |
| Warranty Deed | $206,500 | Attorney | |
| Warranty Deed | $116,950 | Attorney | |
| Personal Reps Deed | $79,000 | -- | |
| Warranty Deed | $81,000 | -- |
Source: Stellar MLS
MLS Number: A4667419
APN: 0157-01-2043
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Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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