321 LOOKOUT POINT DRIVE Osprey, FL $ 3,100,000
321 LOOKOUT POINT DRIVE
$ 3,100,000
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321 LOOKOUT POINT DRIVE

Osprey, FL, 34229
$ 3,100,000
Bedrooms3 Baths3.1 Sq 3,122

Monthly Estimate*

$ 19,574

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Single Family Home for sale in Osprey, FL

for $3,100,000 with 3 bedrooms and 3 full baths, 1 half bath. This 3,122 square foot home was built in 1978 on a lot size of 0.34.

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.

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Single Family Pending

Price

$ 3,100,000

Bedrooms

3

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 16,001

Style

Single Family Residence

Lot Size

0.34

Year Built

1978

Town/City

Osprey

County/Region

Sarasota

MLS | Web ID

A4697345

Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities Electricity Connected
Possession Close Of Escrow
Roof Tile
Appliances Built-In Oven Cooktop Dishwasher
Zoning RSF2
HOA Fee 656.62
Garage Spaces 2
Pool Features In Ground
Construction Materials Stucco
Pets Allowed Yes
Year Built 1978
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Assoc Fee Paid Per Quarterly
County Sarasota
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name SOUTHBAY YACHT & RACQUET CLUB
Facing Direction Northeast
Garage Y/N true
Total Rooms 7
Full Baths 3
Status Pending
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.
High School Venice Senior High
City OSPREY
Association Name Southbay Yacht and Racquet Club/Judy Brown
Senior Community Y/N false
MLS Area 34229 - Osprey
Lot Size Units Square Feet
Lot Size Square Feet 14888
Carport Y/N false
Listing Terms Cash Conventional
Elementary School Laurel Nokomis Elementary
Land Lease Y/N false
Tax Annual Amount 16001.71
Middle/Junior High School Sarasota Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://pix360.com/phototour3/42644
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Pending
Occupancy Type Vacant
Tax Lot 292
Legal Description LOT 292 SOUTHBAY YACHT & RACQUET CLUB
Minimum Lease 1-2 Years
Water Access Y/N false
Monthly HOA Amount 218.87
Water View Y/N false
Flood Zone Code AE*
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Interior
Interior Amenities High Ceilings
Flooring Carpet Tile Hardwood
Furnished Y/N Unfurnished
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 1
Laundry Features Inside
Total Bedrooms 3
Total Baths 4
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Exterior
Exterior Amenities Balcony Outdoor Grill Outdoor Kitchen Sliding Doors
Water Source Public
Lot Size Area 14888
Foundation Details Slab
Building Area Total 4469
Lot Size Acres 0.34
Road Surface Type Paved
Private Pool true
Waterfront Y/N false
Covered Spaces 2
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* Excluded Features
List By
steveabbe@pga.com

Email

Affordability Calculator

$20,907
Per Month
94%
6%
0%
Monthly Principal & Interest
$19,574
Monthly Property Taxes
$1,333
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Venice Senior High High School High School
Pricing History
DatePricePrice ChangeDescription
6/26/2026$3,100,000 Listed Price

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321 LOOKOUT POINT DRIVE, Osprey, FL, 34229 is a Single Family Home for sale at $3,100,000 with 3,122 sqft and a lot size of 0.34. 321 LOOKOUT POINT DRIVE has 3 bedrooms, 3.1 baths, and was built in 1978. The property's zip code is 34229 which is in Osprey, FL