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For sale
$2,399,000
4beds
3,953sqft

49 OSPREY POINT DRIVE, OSPREY, FL 34229

4beds
3,953sqft
Single family residence
Built in 1989
0.40 Acres
2 Attached garage spaces
$607 price/sqft
$475/mo HOA

What's special

Private oasisRetractable window wallsSparkling poolExpansive spaExquisite baths and fixturesTranquil water featuresSoaring vaulted ceilings

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.

287 days
|
724
|
22
|
Source: Stellar MLS,MLS#: A4671762MLS LogoOriginating MLS: Sarasota - Manatee
Travel times

Living Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

Jonathan Abrams, PLLC 941-232-2868,

MICHAEL SAUNDERS & COMPANY 941-349-3444

Source: Stellar MLS,MLS#: A4671762MLS LogoOriginating MLS: Sarasota - Manatee

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 4
  • Bathrooms: 4
  • Full bathrooms: 3
  • 1/2 bathrooms: 1
Rooms
  • Room types: Living Room
Primary bedroom
  • Features: Walk-In Closet(s)
  • Level: First
Bedroom 2
  • Features: Built-in Closet
  • Level: First
Bedroom 3
  • Features: Built-in Closet
  • Level: First
Great room
  • Level: First
Kitchen
  • Level: First
Heating
  • Central, Zoned
Cooling
  • Central Air, Zoned
Appliances
  • Included: Dishwasher, Range, Range Hood, Refrigerator
  • Laundry: Inside, Laundry Room
Features
  • Built-in Features, Ceiling Fan(s), Central Vacuum, Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
  • Flooring: Concrete
  • Doors: Outdoor Shower, Sliding Doors
  • Windows: Hurricane Shutters/Windows
  • Has fireplace: Yes
  • Fireplace features: Family Room, Living Room
Interior area
  • Total structure area: 5,227
  • Total interior livable area: 3,953 sqft

Property

Parking
  • Total spaces: 2
  • Parking features: Workshop in Garage
  • Attached garage spaces: 2
Features
  • Levels: One
  • Stories: 1
  • Patio & porch: Covered, Enclosed, Screened
  • Exterior features: Outdoor Shower, Storage
  • Has private pool: Yes
  • Pool features: Fiber Optic Lighting, In Ground, Salt Water
  • Has spa: Yes
  • Spa features: Heated, In Ground, Other
  • Has view: Yes
  • View description: Lake
  • Has water view: Yes
  • Water view: Lake
  • Waterfront features: Bay/Harbor Front, Lake Front, Lake Privileges, Fishing Pier
Lot
  • Size: 0.4 Acres
  • Features: Landscaped, Oversized Lot, Above Flood Plain
  • Residential vegetation: Mature Landscaping
Details
  • Parcel number: 0142060007
  • Zoning: RSF1
  • Special conditions: None

Construction

Type & style
  • Home type: SingleFamily
  • Architectural style: Contemporary,Custom
  • Property subtype: Single Family Residence
Materials
  • Block, Concrete, Stucco
  • Foundation: Slab
  • Roof: Tile
Condition
  • New construction: No
  • Year built: 1989

Utilities & green energy

  • Sewer: Public Sewer
  • Water: Public
  • Utilities for property: Cable Connected, Electricity Connected, Public, Water Connected
Green energy
  • Indoor air quality: Whole House Vacuum System

Community & HOA

Community
  • Features: Bay/Harbor Front, Dock, Fishing, Water Access, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Restaurant, Tennis Court(s)
  • Security: Gated Community
  • Pet fee: $0 monthly
  • Subdivision: OAKS
HOA
  • Has HOA: Yes
  • Amenities included: Clubhouse, Fitness Center, Golf Course, Maintenance, Pickleball Court(s), Tennis Court(s)
  • HOA fee: $475 monthly
  • HOA name: The Oaks Club
  • HOA phone: 941-966-2161
Location
  • Region: Osprey

Financial & listing details

  • Price per square foot: $607/sqft
  • Tax assessed value: $1,354,900
  • Annual tax amount: $14,206
  • Date on market: 11/13/2025
  • Cumulative days on market: 204 days
  • Ownership: Fee Simple
  • Total actual rent: 0
  • Electric utility on property: Yes
  • Road surface type: Asphalt

Price history

DateEventPrice
5/3/2026Price change$2,399,000-4%$607/sqft
Source: Stellar MLS #A4671762 Report a problem
1/29/2026Price change$2,500,000-3.7%$632/sqft
Source: Stellar MLS #A4671762 Report a problem
11/13/2025Listed for sale$2,595,000-3.7%$656/sqft
Source: Stellar MLS #A4671762 Report a problem
9/1/2025Listing removed$2,695,000$682/sqft
Source: Stellar MLS #A4642364 Report a problem
7/24/2025Price change$2,695,000-1.8%$682/sqft
Source: Stellar MLS #A4642364 Report a problem
6/11/2025Price change$2,745,000-1.8%$694/sqft
Source: Stellar MLS #A4642364 Report a problem
4/3/2025Price change$2,795,000-6.7%$707/sqft
Source: Stellar MLS #A4642364 Report a problem
3/5/2025Listed for sale$2,995,000+274.4%$758/sqft
Source: Stellar MLS #A4642364 Report a problem
6/4/2019Sold$800,000-5.9%$202/sqft
Source: Public Record Report a problem
4/17/2019Pending sale$850,000$215/sqft
Source: Coldwell Banker Residential Real Estate - Longboat Key #A4431344 Report a problem
3/29/2019Listed for sale$850,000+49.1%$215/sqft
Source: COLDWELL BANKER RES R E #A4431344 Report a problem
7/15/1998Sold$570,000+14.6%$144/sqft
Source: Public Record Report a problem
7/5/1996Sold$497,500$126/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
2025$14,702 +3.5%$997,918 +10%
2024$14,206 +14.7%$907,198 +10%
2023$12,389 +4.6%$824,725 +10%
2022$11,844 +45%$749,750 +21.2%
2021$8,167 +1.7%$618,500 +3.9%
2020$8,028 +0.7%$595,200 -5.8%
2019$7,970 $631,780 +1.9%
2018$7,970 +2%$620,000 -0.9%
2017$7,814 -4.9%$625,900 +2%
2016$8,215 $613,500 -6.1%
2015$8,215 +0.3%$653,300 +9.4%
2014$8,187 +0%$597,081
2013$8,187 +2.7%$597,081 +1.7%
2012$7,971 +4.7%$587,100 +3%
2011$7,616 -16.9%$570,000 -14.7%
2010$9,162 +10.4%$668,265 +2.7%
2009$8,298 $650,696 +0.1%
2008$8,298 +0.6%$650,046 +3%
2007$8,246 $631,113 +2.5%
2006-- $615,720 +3%
2005-- $597,786 +3%
2004$8,709 -1.2%$580,375 +1.9%
2003$8,815 +2.4%$569,553 +2.4%
2002$8,606 +7.4%$556,204 +1.6%
2001$8,014 +2.7%$547,445 +3%
2000$7,805 $531,500

Find assessor info on the county website

Monthly payment

Est. payment
$15,031/mo
Principal & interest
$12017
Property taxes
$2539
HOA Fees
$475
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Estimated market value

Not available

Estimated sales range

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Climate risks

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Neighborhood: 34229

Nearby schools

Laurel Nokomis School
Grades PK-8 • 6.4 miles
8/10
GreatSchools® Rating
Test Score Rating
8/10
Student Progress Rating
8/10
Venice Senior High School
Grades 9-12 • 8.5 miles
7/10
GreatSchools® Rating
Test Score Rating
7/10
College Readiness Rating
8/10
Student Progress Rating
5/10

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