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Single family home for sale at 75 Osprey Point Dr, Osprey, FL 34229 | MLS# A4695145 | Listing updated on 2026-10-07
Photo 1 of Single family home for sale at 75 Osprey Point Dr, Osprey, FL 34229 | MLS# A4695145 | Listing updated on 2026-10-07
Photo 2 of Single family home for sale at 75 Osprey Point Dr, Osprey, FL 34229 | MLS# A4695145 | Listing updated on 2026-10-07
Photo 3 of Single family home for sale at 75 Osprey Point Dr, Osprey, FL 34229 | MLS# A4695145 | Listing updated on 2026-10-07
Photo 4 of Single family home for sale at 75 Osprey Point Dr, Osprey, FL 34229 | MLS# A4695145 | Listing updated on 2026-10-07
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$1,595,000

Monthly Est:$7,939

  • Beds Icon4 Beds
  • Beds Icon
    4 Baths
  • Beds Icon4,001sqft

75 Osprey Point Dr, Osprey, FL 34229

$7,939/moEst:

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  • Single Family Residence

  • Built in 1983

  • $950/mo HOA

  • 32,983 sqft lot

  • $399/sq.ft

Description

Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks.

Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting.

A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fi
replace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout.

The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer.

Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community.

Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key.

Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar.

Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

  • Houzeo last checked: 0 minutes ago
  • Listing updated: October 7, 2026 at 1:24 pm
  • Listing Provided by: Steve Abbe (941) 400-3969 , Shannon Rocha | COLDWELL BANKER REALTY (941) 383-6411
  • Source: Stellar MLS-FL | MLS#: A4695145 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Sarasota County

  • City

    Osprey

  • Neighborhood

    --

  • Year Built

    1983

  • HOA Fees

    $950/mo

  • Finished Area

    4,001 sqft

  • Lot Size

    32,983 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    A4695145

  • MLS Status

    Active

  • Days on Market

    121

  • Cumulative Days on Market

    287

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Location

HOA Management

Access Management/Hope Root

HOA Fees

$5,700/ Semi-Annually

Amenities

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

Security Guard Security Guard

Security Gate Security Gate

Management Management

Vehicle Restrictions Vehicle Restrictions

Fidelity Bond Fidelity Bond

Private Road Private Road

Escrow Reserves Fund Escrow Reserves Fund

Common Area Taxes Common Area Taxes

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

  • Foyer

    Level: First

    Area: 216.00 Square Feet

    Dimensions: 12x18

  • Great Room

    Level: First

    Area: 990.00 Square Feet

    Dimensions: 22x45

  • Dining Room

    Level: First

    Area: 1160.00 Square Feet

    Dimensions: 29x40

  • Studio

    Level: First

    Area: 240.00 Square Feet

    Dimensions: 12x20

  • Kitchen

    Level: First

    Area: 135.00 Square Feet

    Dimensions: 9x15

  • Primary Bedroom

    Level: First

    Area: 224.00 Square Feet

    Dimensions: 14x16

  • Bedroom 2

    Level: First

    Area: 208.00 Square Feet

    Dimensions: 13x16

  • Bedroom 3

    Level: First

    Area: 121.00 Square Feet

    Dimensions: 11x11

  • Laundry

    Level: First

    Area: 104.00 Square Feet

    Dimensions: 13x8

Interior

  • Appliances

    Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator

  • Heating

    Heat Pump, Zoned

  • Window Features

    Blinds, Drapes, Insulated Windows, Rods, Window Treatments

  • Cooling

    Central Air, Zoned

  • Interior Features

    Ceiling Fans(s), Crown Molding, High Ceilings, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk In Closet(s), Window Treatments

  • Sewer

    Public Sewer

  • Flooring

    Carpet, Tile

Construction

  • Year Built

    Year Built: 1983

  • Home type

    Single Family Residence

  • Architectural Style

    Traditional

  • Construction Materials

    Block, Stucco

  • Roof

    Concrete, Tile

  • Foundation Details

    Slab

Utilities & Energy

  • Parking Features

    Circular Driveway, Garage Faces Side

  • Association Amenities

    Gated, Security, Vehicle Restrictions

  • Utilities

    Bb/hs Internet Available, Cable Connected

  • Security Features

    Security System, Security System Owned, Smoke Detector(s)

  • Pool Features

    In Ground

  • Water Source

    Public

  • Laundry Features

    Inside, Laundry Room

  • Fireplace Features

    Wood Burning

Other Features

  • Patio And Porch Features

    Patio

  • Lot Features

    In County, Near Golf Course, Private

  • Community Features

    Deed Restrictions, Golf, Irrigation Reclaimed Water

  • Subdivision Name

    Oaks

  • Vegetation

    Bamboo, Mature Landscaping, Oak Trees, Trees/landscaped, Wooded

Price History

DateEventPrice

10/07/2026

Source: mls_logoStellar MLS-FL #MFRA4695145

Listed for Sale

$1,595,000

$399/sqft

08/13/2026

Source: mls_logoStellar MLS-FL #MFRA4695145

Pending

$1,595,000 -3.27%

$399/sqft

06/11/2026

Source: mls_logoStellar MLS-FL #MFRA4695145

Listed for Sale

$1,649,000 -2.71%

$412/sqft

05/20/2026

Source: mls_logoStellar MLS-FL #MFRA4672439

Listing Removed

$1,695,000

$424/sqft

04/14/2026

Source: mls_logoStellar MLS-FL #MFRA4672439

Price Decreased

$1,695,000 -4.51%

$424/sqft

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Nearby Homes

Based on information from Stellar MLS® through Oct 11, 2026, 12:30AM 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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