144 N CASEY KEY ROAD, Osprey, FL, 34229 | $5,990,000

A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless residence blends architectural elegance with waterfront living. Offering private access to the Intracoastal with a 100-foot dock (built in 2019), dual 12, 000-pound lifts, water, and electric, this property is an ideal destination for boating enthusiasts. Offered fully furnished upon request. The front elevation is framed by a raised lawn with a stone wall, a paver driveway and manicured landscaping. As you approach the home, the travertine steps lead you to the new custom front door, where dramatic water views of the bay immediately greet you through expansive windows on opposite side of the home, creating a seamless connection to the Gulf and Bay. Inside, the main level is anchored by a breathtaking great room with coffered ceilings, custom millwork, and a wall of windows and doors that open to the terrace, creating an indoor/outdoor living space. A two-sided fireplace adds warmth and ambiance to the great room and the adjacent terrace. The interior showcases a multitude of upgrades, including updated Palecek lighting, and new porcelain tile flooring throughout. The 2020-renovated gourmet kitchen showcases bay views, Cambria Skara Brae quartz countertops, subway tile backsplash, custom white cabinetry and premium stainless-steel appliances. A bar area includes a wine refrigerator and ice maker, while a built-in pantry corridor connects seamlessly to the dining room. The dining area features built-in cabinetry and enjoys stunning bay views from the terrace. The formal living room, with its tranquil blue and cream tones, provides a lovely space to enjoy Gulf views while welcoming guests for dinner. The home offers two spacious primary suites, each with walk-in closets and luxurious en-suite baths, offering serene bay views and access to their private travertine terrace. Two guest suites and an upstairs office also enjoy remarkable water views. The staircase to the upper level reveals an oversized picture window framing the Gulf views. A three-floor elevator provides convenient access to all levels. The ground level features a spacious three-car garage with a dedicated golf cart space. Abundant space is designed to accommodate a variety of uses, and a new glass custom door offers light and access to the backyard and patio. Impact-rated windows and doors, along with a whole-house generator, provide peace of mind. Outside, the resort-style backyard features a refinished pool (with new tile and resurfacing), lush tropical landscaping, an expanded travertine patio and tiered terraces with custom stonework, columns, and stone floors. A rooftop deck offers panoramic views of the Gulf and Bay. Water enthusiasts will appreciate seamless access to the Intracoastal and Gulf, ideal for effortless boating. Additional upgrades include a newly painted roof tile, full exterior and interior repainting (2023), new fencing for added privacy, and two new entry doors (2025), completing the home’s thoughtful transformation. 144 N. Casey Key Road presents a rare opportunity to own a private waterfront estate offering luxury, seclusion and convenient access to Sarasota’s shopping, dining, beaches and parks.

Features

  • Rooms: 10
  • Bedrooms: 4
  • Baths: 5 full / 1 half
  • Laundry: Inside, Laundry Room, Upper Level
  • Style: Florida
  • Year Built: 2003
  • Garage: 3-car Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Oversized
  • Heating: Central, Electric
  • Cooling: Central Air
  • Approx Sq. Feet: 5,397
  • Acreage: 0.55
  • Est. Taxes: $54,908
  • Lot Desc: Flood Insurance Required, FloodZone, In County, Landscaped
  • View: Water
  • Elem. School: Laurel Nokomis Elementary
  • Middle School: Laurel Nokomis Middle
  • High School: Venice Senior High
  • Pool: Gunite, Heated, In Ground, Lighting
  • Pet Policy: Yes
  • Appliances: Bar Fridge, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator
  • MLS#: A4660004
  • Days on Market: 100 days
  • Website: https://www.raveis.com
    /eprop/A4660004/144ncaseykeyroad_osprey_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. (last updated 12/24/2025 4:18:05 AM)
Listing courtesy of DOUGLAS ELLIMAN   Phone: 941-867-6199

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NMLS Mortgage Loan Originator ID 16953

917.838.7300

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144 N CASEY KEY ROAD, Osprey, FL, 34229

$5,990,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $4,792,000 $4,792,000 $4,792,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.625% 6.000% 5.875%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.353% 6.121% 6.038%
Monthly Tax Payment $4,576 $4,576 $4,576
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $27,585 $28,730 $40,115
Total Monthly Payment $32,286 $33,431 $44,816

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.