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321 Lookout Point Drive, Osprey, FL 34229

$3,100,000

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Property Description

Experience the epitome of waterfront living in the sought-after Southbay neighborhood. This 3 bedroom, 3.5 bath home is ideally positioned on a peninsula, providing sweeping panoramic water views. The moment you step inside, you will be mesmerized by the breathtaking bay views through a plethora of windows and sliding glass doors that flood the space with natural light. The open, main level is designed for both comfort and style, with vaulted ceilings, unobstructed water views from every room and hardwood floors. The kitchen is uniquely designed, featuring an extended breakfast bar, high end designer cabinets and stainless steel appliances. The great room, with wet bar, has views so perfect, they almost feel like artwork. The new clear view lanai screens provide a gorgeous tropical back drop to the pool and spa. Host friends and loved ones, using the outdoor kitchen and setting area for a fun-filled dinner, and watch the sun set, painting the sky with a golden glow. The first floor master suite consists of a spacious bedroom, a spa-like bathroom, and a separate area utilized as a private study. Upstairs you will find two additional en suite bedrooms. One opens to the new deck, has views over the Dryman Bay out to Casey Key, and is large enough to use as a second master suite. While the views and location of this home are drop-dead gorgeous, practical features also abound. This home has impact windows and doors, a brand new washer and dryer, and recently replaced roof, AC and tankless hot water heater. Southbay Yacht and Racquet Club has a seven-acre deep-water marina accommodating boats up to 55 feet with slips available to homeowners. It has an updated clubhouse and fitness center overlooking the bay, complete with a ballroom, catering kitchen, meeting room and library. Community amenities also include a geothermal heated pool, children's pool, tennis, pickleball, shuffleboard, basketball and kayak storage. Residents enjoy 20 acres of lush common grounds and five miles of walking trails, plus a vibrant calendar of social events.

321 Lookout Point Drive | MLS# A4697345

This single family home located at 321 Lookout Point Drive, Osprey, FL 34229 is currently listed for sale with an asking price of $3,100,000. This property was built in 1978 and has 3 bedrooms and 3 full and 1 partial baths with 3122 sq. ft. Lookout Point Drive is located in the SOUTHBAY YACHT & RACQUET CLUB subdivision. Search SOUTHBAY YACHT & RACQUET CLUB real estate on lisawest.watsonrealtycorp.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Garage: 2 car attached
Heating: Central
Lot Size: 0.34 Acres
Roof Type: Tile
Stories: 2.0
Taxes: $16,001
Year Built: 1978
Square Feet: 3,122

Amenities

High Ceilings
Balcony
Outdoor Grill
Outdoor Kitchen
Sliding Doors

Feature Descriptions

Appliances: Built-In Oven, Cooktop, Dishwasher
Directions: Rte. 41/South Tamiami Trail to Blackburn Point Rd. West on Blackburn. Make a right on Southbay Drive. Make a left on Harbor Huse Drive. Make a right on Lookout Point Dr. to address.
Exterior: Stucco
Flood Zone Code: AE*
Flooring: Carpet, Tile, Wood
Foundation: Slab
Garage Dimensions: 19x22
HOA Fee: 656.62/ Quarterly
HOA Y/N: Yes
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot Dimensions: 0.34
Ownership: Fee Simple
Pets Allowed: Yes
Pool: In Ground
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Showing Instructions: Appointment Only, Contact Call Center, Listing Agent Must Accompany, ShowingTime
Special Sale Provisions: None
Swimming Pool: Yes
Utilities: Electricity Connected
Water: Public
Water Access Y/N: No
Zoning: RSF2

Room Sizes

Great Room: 34x20
Dining Room: 21x13
Kitchen: 19x12
Primary Bedroom: 19x13
Bedroom 2: 14x13
Bedroom 3: 16x13
Balcony/Porch/Lanai: 48x29

Local Schools

High School: Venice Senior High
Middle School: Sarasota Middle
Elementary School: Laurel Nokomis Elementary

Listed By / Shown By

Listed By

Agency Name: COLDWELL BANKER REALTY
Agency Contact: 941-383-6411

Shown By

Agent Name: Lisa West
Agent Phone: (352) 267-9912
Agency Title: Watson Realty Corp., REALTORS ®

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Estimated Payment

$ 18,010.86 per month $15,773.27 Principal & Interest $1,333.42 Property Tax $904.17 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/27/2026. The listing information on this page last changed on 06/27/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 06/27/2026 12:13:40 AM EST) or GAMLS (last updated Fri 06/26/2026 11:15:43 PM EST) or Stellar MLS (last updated Fri 06/26/2026 11:59:04 PM EST) or SPC MLS (last updated Fri 06/26/2026 11:21:31 PM EST) or Martin MLS (last updated Fri 06/26/2026 11:38:10 PM EST) or Indian River MLS (last updated Fri 06/26/2026 11:30:19 PM EST) or Daytona MLS (last updated Fri 06/26/2026 11:36:51 PM EST) or Northeast Florida MLS (last updated Sat 06/27/2026 12:08:58 AM EST) or Beaches MLS (last updated Sat 06/27/2026 12:09:31 AM EST) or BORMLS (last updated Fri 06/26/2026 11:15:59 PM EST) or Amelia/Nassau MLS (last updated Fri 06/26/2026 11:25:15 PM EST) or Dixie Gilchrist Levy MLS (last updated Fri 06/26/2026 11:42:19 PM EST) or NFLMLS (last updated Fri 06/26/2026 9:05:11 PM EST). Real estate listings held by brokerage firms other than Watson Realty Corp., REALTORS ® may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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