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Property for sale at 242 LOOKOUT POINT DRIVE, OSPREY, FL, 34229
Property for sale at 242 LOOKOUT POINT DRIVE, OSPREY, FL, 34229
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242 Lookout Point DriveOsprey, FL, 34229

4beds
2baths
2,413sqft
Single Family Residence
Built in 1978
$657 Quarterly HOA Fee
$995,000
For sale
Price per sqft
$412
Days on market
8
Listed
Oct 30
MLS #A4711269Updated Nov 6, 2026

About this property

Meticulously maintained, furnished four-bedroom residence in Southbay Yacht and Racquet Club, a sought-after waterfront community in Osprey. The community-owned marina features 172 boat slips accommodating vessels up to 55 feet within a protected, deep-water basin. HOA fees are just $218 per month. Enjoy the remodeled clubhouse overlooking the marina, offering an impressive array of amenities, including two kitchens, an elegant ballroom, a fitness center, a card room and an inviting living room complete with a grand piano. Outdoor enthusiasts will appreciate the pickleball and tennis courts, bocce ball, swimming pool, playground and convenient kayak launch and storage. The spacious great room and dining area are highlighted by a charming wood-burning fireplace, creating a warm and inviting atmosphere for entertaining family and friends. The thoughtfully designed split-bedroom floor plan provides added privacy for family and guests. Recent improvements include a new metal roof, hurricane-rated windows, newer A/C units and beautiful brick pavers enhancing both the driveway and pool area. Conveniently located between Sarasota and Venice, approximately 20 minutes from Siesta Key Beach and just a quarter mile from the Legacy Trail, offering miles of scenic paths and easy access to Oscar Scherer State Park. Enjoy nearby waterfront dining, shopping and local amenities just a short distance away. Osprey is also home to Pine View School for the Gifted, a highly regarded public school.

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Property details

Property type
Single Family Residence
Street address
242 Lookout Point Drive
City
Osprey
State
FL
ZIP code
34229
Year built
1978
New construction
No
Attached property
Yes
Faces
West
Rooms
11
Building stories
2
Living area
2,413 sqft
Total building area
3,414 sqft
Levels
Multi/Split

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at November 7, 2026 at 3:00 PM EST

Price & sale history

EventPrice
Listed for saleMLS #A4711269$995,000
SoldMLS #D5915364$430,000
Price reducedMLS #D5915364$449,900Change: −4.1%−$19,100
Listed for saleMLS #D5915364$469,000
History may be incomplete.
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Property for sale at 242 LOOKOUT POINT DRIVE, OSPREY, FL, 34229
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