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Pending
  • $3,100,000

    321 Lookout Point Dr, Osprey, FL 34229

    3beds
    3,122sqft
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    Single Family Residence
    Built in 1978
    0.34 Acres Lot
    $3,000,100 Zestimate®
    $993/sqft
    $219/mo HOA

    What's special

    High end designer cabinetsRecently replaced roofSpa-like bathroomSweeping panoramic water viewsVaulted ceilingsExtended breakfast barHardwood floors
    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.
    6 days
    |
    513
    |
    31
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Steve Abbe 941-400-3969,

    COLDWELL BANKER REALTY 941-383-6411

    Source: Stellar MLS,MLS#: A4697345MLS LogoOriginating MLS: Sarasota - Manatee

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 247 Square Feet
      • Dimensions: 19x13
      Bedroom 2
      • Features: Built-in Closet
      • Level: Second
      • Area: 182 Square Feet
      • Dimensions: 14x13
      Bedroom 3
      • Features: Built-in Closet
      • Level: Second
      • Area: 208 Square Feet
      • Dimensions: 16x13
      Balcony porch lanai
      • Level: First
      • Area: 1392 Square Feet
      • Dimensions: 48x29
      Dining room
      • Level: First
      • Area: 273 Square Feet
      • Dimensions: 21x13
      Great room
      • Level: First
      • Area: 680 Square Feet
      • Dimensions: 34x20
      Kitchen
      • Level: First
      • Area: 228 Square Feet
      • Dimensions: 19x12
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Oven, Cooktop, Dishwasher
      • Laundry: Inside
      Features
      • High Ceilings
      • Flooring: Carpet, Tile, Hardwood
      • Doors: Outdoor Grill, Outdoor Kitchen, Sliding Doors
      • Has fireplace: No
      Interior area
      • Total structure area: 4,469
      • Total interior livable area: 3,122 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage - Attached
      • Attached garage spaces: 2
      • Details: Garage Dimensions: 19x22
      Features
      • Levels: Two
      • Stories: 2
      • Exterior features: Balcony, Outdoor Grill, Outdoor Kitchen
      • Has private pool: Yes
      • Pool features: In Ground
      Lot
      • Size: 0.34 Acres
      Details
      • Parcel number: 0158020018
      • Zoning: RSF2
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Stucco
      • Foundation: Slab
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 1978

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Electricity Connected

      Community & HOA

      Community
      • Pet fee: $0 monthly
      • Subdivision: SOUTHBAY YACHT & RACQUET CLUB
      HOA
      • Has HOA: Yes
      • HOA fee: $219 monthly
      • HOA name: Southbay Yacht and Racquet Club/Judy Brown
      • HOA phone: 941-966-4237
      Location
      • Region: Osprey

      Financial & listing details

      • Price per square foot: $993/sqft
      • Tax assessed value: $2,792,800
      • Annual tax amount: $16,001
      • Date on market: 6/26/2026
      • Cumulative days on market: 7 days
      • Listing terms: Cash,Conventional
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved

        Estimated market value

        $3,000,100

        $2.85M - $3.15M

        $5,326/mo

        Price history

        DateEventPrice
        6/27/2026Pending sale$3,100,000$993/sqft
        Source: Stellar MLS #A4697345 Report a problem
        6/26/2026Listed for sale$3,100,000+507.2%$993/sqft
        Source: Stellar MLS #A4697345 Report a problem
        8/2/1993Sold$510,500$164/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$16,002 +5.2%$1,353,099 +2.9%
        2024$15,206 +2.6%$1,314,965 +3%
        2023$14,824 +4.2%$1,276,665 +5.1%
        2022$14,231 -1.6%$1,214,723 +2%
        2021$14,461 -0.8%$1,190,943 +1.4%
        2020$14,571 +2.6%$1,174,500 +2%
        2019$14,204 $1,151,700 +1.3%
        2018$14,204 +1.3%$1,136,400 -2.6%
        2017$14,024 +55.5%$1,167,300 +0.4%
        2016$9,020 $1,162,300 +1.1%
        2015$9,020 +0.3%$1,149,400 +70.2%
        2014$8,988 0%$675,288
        2013$8,989 +2.8%$675,288 +1.7%
        2012$8,744 -3%$664,000 -4.6%
        2011$9,014 -6.8%$695,700 -4%
        2010$9,669 -13.6%$724,500 -14.1%
        2009$11,189 $843,900 -6.1%
        2008$11,189 +1.1%$898,794 +3%
        2007$11,064 $872,616 +2.5%
        2006-- $851,333 +3%
        2005-- $826,537 +3%
        2004$11,720 -1.3%$802,463 +1.9%
        2003$11,870 +14.7%$787,500 +17.3%
        2002$10,353 +8.8%$671,400 +2.9%
        2001$9,519 +4%$652,300 +4.8%
        2000$9,153 $622,400

        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 34229

        Getting around

        28 / 100
        Car-Dependent
        34 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Laurel Nokomis Elementary
        • Middle: Sarasota Middle
        • High: Venice Senior High

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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