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$5,990,000

For Sale - Active
144 N Casey Key Rd, Osprey, FL 34229
4 Beds
6 Baths
5,397 Square Feet
0.55 Acres Lot
Built in 2003
For Sale - Active
1 Units
Checked: 19 hours ago
Updated: Nov 11, 2025 at 09:12AM

Investment Summary


Monthly Cash Flow
-$29,050
Cap Rate
0.3%
Cash-on-Cash Return
-25.3%
Debt Coverage Ratio
0.05
Internal Rate of Return (5 years)
-20.4%

Property Description


0.55 Acres Lot
Built in 2003
For Sale - Active
1 Units

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.

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Location


Property Details


Parking

  • Description: Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Oversized
  • Details: Driveway, Garage Door Opener, Garage Faces Side, Oversized, Attached
  • Garage Spaces: 3
  • Spaces Total: 0

Bedroom Information

  • # of Bedrooms: 4

Bathroom Information

  • # of Baths (Full): 5
  • # of Baths (Partial): 1
  • # of Baths (Total): 6.0

Interior Features

  • # of Rooms: 10
  • # of Stories: 3
  • Fireplace: Yes

Exterior Features

  • Exterior Walls Materials: Stucco
  • Foundation: Slab
  • Roof Type: Hip
  • Roof Material: Tile
  • Pool: Yes

Land Information

  • Land Use: Residential
  • Land Use Subtype: Single Family Residential

Lot Information

  • Parcel ID: 0146330013
  • Lot Size: 24092 sqft

Property Information

  • Property Type: Single Family Residence
  • Style: Florida
  • Year Built: 2003

Tax Information

  • Annual Tax: $54,908

Utilities

  • Water & Sewer: Public
  • Heating: Central, Electric
  • Cooling: Central Air

Location

  • County: Sarasota

Listing Details


Listed by:
Joel Schemmel
DOUGLAS ELLIMAN
(941) 587-4894

Source:
Stellar MLS
MLS#: A4660004
Stellar MLS

Investment Summary


Monthly Cash Flow
-$29,050
Cap Rate
0.3%
Cash-on-Cash Return
-25.3%
Debt Coverage Ratio
0.05
Internal Rate of Return (5 years)
-20.4%

Purchase Details

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Purchase price:
$5,990,000
Amount financed:
-$4,792,000
Down payment:
$1,198,000
Closing costs:
$179,700
Rehab costs:
$0
Initial cash invested:
$1,377,700
Square feet:
5,397
Cost per square foot:
$1,110
Monthly rent per square foot:
$1.67

Financing Details

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Loan amount:
$4,792,000
Loan to value ratio:
80.0%
Loan type:
Amortizing
Term:
30 years
Interest rate:
6.625%
Principal & interest:
$30,684
Property tax:
$4,576
Insurance:
$630
Private mortgage insurance (PMI):
$0
Monthly payment:
$35,890

Operating Income

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% Rent Monthly Yearly
Gross rent:
$9,000 $108,000
Vacancy loss: (6%)
6% -$540 -$6,480
Operating income:
$8,460 $101,520

Operating Expenses


% Rent Monthly Yearly
Property taxes: (51%)
51%-$4,576-$54,908
Insurance: (7%)
7%-$630-$7,560
Property management: (8%)
8%-$720-$8,640
Repairs & maintenance: (5%)
5%-$450-$5,400
Capital expenditures: (5%)
5%-$450-$5,400
HOA fees: (n/a)
n/an/an/a
Total operating expenses: (76%)
76%-$6,826-$81,908

Cash Flow


Monthly Yearly
Net operating income:
$1,634 $19,608
Mortgage payments:
-$30,684 -$368,208
Cash flow:
-$29,050 -$348,600