For Sale
Single family home for sale at 49 Osprey Point Dr, Osprey, FL 34229 | MLS# A4671762 | Listing updated on 2026-05-19
Photo 1 of Single family home for sale at 49 Osprey Point Dr, Osprey, FL 34229 | MLS# A4671762 | Listing updated on 2026-05-19
Photo 2 of Single family home for sale at 49 Osprey Point Dr, Osprey, FL 34229 | MLS# A4671762 | Listing updated on 2026-05-19
Photo 3 of Single family home for sale at 49 Osprey Point Dr, Osprey, FL 34229 | MLS# A4671762 | Listing updated on 2026-05-19
Photo 4 of Single family home for sale at 49 Osprey Point Dr, Osprey, FL 34229 | MLS# A4671762 | Listing updated on 2026-05-19
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Street View

$2,399,000

Monthly Est:$11,941

  • Beds Icon4 Beds
  • Beds Icon
    4 Baths
  • Beds Icon3,953sqft

49 Osprey Point Dr, Osprey, FL 34229

$11,941/moEst:

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  • Single Family Residence

  • Built in 1989

  • $475/mo HOA

  • 17,230 sqft lot

  • $607/sq.ft

Description

Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.

  • Houzeo last checked: 8 minutes ago
  • Listing updated: May 19, 2026 at 4:33 pm
  • Listing Provided by: Jonathan Abrams, PLLC (941) 232-2868 | MICHAEL SAUNDERS & COMPANY (941) 349-3444
  • Source: Stellar MLS-FL | MLS#: A4671762 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    1

  • County

    Sarasota County

  • City

    Osprey

  • Neighborhood

    --

  • Year Built

    1989

  • HOA Fees

    $475/mo

  • Finished Area

    3,953 sqft

  • Lot Size

    17,230 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    A4671762

  • MLS Status

    Active

  • Days on Market

    331

  • Cumulative Days on Market

    187

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Location

HOA Management

The Oaks Club

HOA Fees

$5,700/ Annually

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Maintenance Maintenance

Golf Golf

Tennis Tennis

Club House Club House

Gym Gym

Sports Court Sports Court

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 4

  • Kitchen

    Level: First

  • Great Room

    Level: First

  • Primary Bedroom

    Level: First

  • Bedroom 2

    Level: First

  • Bedroom 3

    Level: First

Interior

  • Heating

    Central, Zoned

  • Cooling

    Central Air, Zoned

  • Interior Features

    Built In Features, Ceiling Fans(s), Central Vaccum, Eat In Kitchen, High Ceilings, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk In Closet(s)

  • Appliances

    Dishwasher, Range, Range Hood, Refrigerator

  • Sewer

    Public Sewer

  • Flooring

    Concrete

  • Exterior Features

    Outdoor Shower, Sliding Doors, Storage

Construction

  • Year Built

    Year Built: 1989

  • Home type

    Single Family Residence

  • Construction Materials

    Block, Concrete, Stucco

  • Foundation Details

    Slab

  • Roof

    Tile

  • Architectural Style

    Contemporary, Custom

Utilities & Energy

  • Utilities

    Cable Connected, Electricity Connected, Public, Water Connected

  • Security Features

    Gated Community

  • Fireplace Features

    Family Room, Living Room

  • Laundry Features

    Inside, Laundry Room

  • Parking Features

    Workshop In Garage

  • Association Amenities

    Clubhouse, Fitness Center, Golf Course, Maintenance, Pickleball Court(s), Tennis Court(s)

  • Water Source

    Public

  • Pool Features

    Fiber Optic Lighting, In Ground, Salt Water

Other Features

  • Vegetation

    Mature Landscaping

  • Patio And Porch Features

    Covered, Enclosed, Screened

  • Subdivision Name

    Oaks

  • Lot Features

    Landscaped, Oversized Lot

  • Community Features

    Clubhouse, Deed Restrictions, Fitness Center, Gated Community Guard, Golf, Pool, Restaurant, Tennis Court(s)

Price History

DateEventPrice

05/03/2026

Source: mls_logoStellar MLS-FL #MFRA4671762

Price Decreased

$2,399,000 -4.04%

$607/sqft

01/29/2026

Source: mls_logoStellar MLS-FL #MFRA4671762

Price Decreased

$2,500,000 -3.66%

$632/sqft

11/13/2025

Source: mls_logoStellar MLS-FL #MFRA4671762

Listed for Sale

$2,595,000 -3.71%

$656/sqft

09/01/2025

Source: mls_logoStellar MLS-FL #MFRA4642364

Listing Removed

$2,695,000

$682/sqft

07/24/2025

Source: mls_logoStellar MLS-FL #MFRA4642364

Price Decreased

$2,695,000 -10.02%

$682/sqft

Show more

Nearby Homes

Based on information from Stellar MLS® through Oct 11, 2026, 05:15PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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