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.
Property Details
Price:
$995,000
MLS #:
A4711269
Status:
Active
Beds:
4
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
SOUTHBAY YACHT & RACQUET CLUB
Neighborhood:
34229osprey
Listed Date:
Oct 30, 2026
Finished Sq Ft:
2,413
Total Sq Ft:
3,414
Lot Size:
12,041 sqft / 0.28 acres (approx)
Year Built:
1978
See this Listing
Schools
Elementary School:
Laurel Nokomis Elementary
Middle School:
Sarasota Middle
High School:
Venice Senior High
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Ceramic Tile, Parquet
Heating
Central, Electric
Interior Features
Cathedral Ceiling(s), High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Vaulted Ceiling(s), Walk-In Closet(s)
Laundry Features
Inside
Levels
Multi/Split
Exterior
Architectural Style
Florida
Association Amenities
Basketball Court, Clubhouse, Elevator(s), Fence Restrictions, Fitness Center, Lobby Key Required, Pickleball Court(s), Playground, Pool, Shuffleboard Court, Tennis Court(s), Trail(s)
Attached Garage YN
1
Community Features
Bay/Harbor Front, Boat Slip, Canal Front, Dock, Fishing, Intracoastal Waterway, Marina, Water Access, Waterfront, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Pool, Tennis Court(s)
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
West
Exterior Features
Irrigation System, Lighting, Private Entrance, Rain Gutters, Sliding Doors
Garage Spaces
2
Lot Features
Landscaped, Near Marina
Open Parking YN
1
Parking Features
Circular Driveway, Garage Door Opener, Garage Faces Side, Oversized
Patio And Porch Features
Covered, Deck, Patio, Porch, Screened
Roof
Metal
View
Pool
Waterfront Features
Bay/Harbor Front, Canal Front, Waterfront, Bay/Harbor
Window Features
Blinds, Drapes, Window Treatments
Financial
HOA Fee
$657
HOA Fee Frequency
Quarterly
HOA Includes
Common Area Taxes, Community Pool, Escrow Reserves Fund, Maintenance Grounds, Manager, Pool Maintenance, Recreational Facilities
HOA Name
Rachelle Freed
HOA Phone
941-966-4237
Tax Year
2025
Taxes
$8,220
Map
Community
- Address242 LOOKOUT POINT DRIVE OSPREY FL
- SubdivisionSOUTHBAY YACHT & RACQUET CLUB
- CityOSPREY
- CountySarasota
- Zip Code34229
Market Summary
Current real estate data for Single Family in OSPREY as of Nov 03, 2026
79
Single Family Listed
139
Avg DOM
458
Avg $ / SqFt
$1,420,744
Avg List Price
Property Summary
- Located in the SOUTHBAY YACHT & RACQUET CLUB subdivision, 242 LOOKOUT POINT DRIVE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $995,000 and features 4 beds, 2 baths, and has approximately 2,413 square feet of living space, and was originally constructed in 1978. The current price per square foot is $412. The average price per square foot for Single Family listings in OSPREY is $458. The average listing price for Single Family in OSPREY is $1,420,744. To schedule a showing of MLS#a4711269 at 242 LOOKOUT POINT DRIVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of PREMIER SOTHEBY’S INTERNATIONAL REALTY. 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. 242 LOOKOUT POINT DRIVE
OSPREY, FL
