For sale Home

Listed May 15, 2026

$3,495,000 Est. $23,116/mo

58652 Overseas Highway

  • 4

    Beds

  • 4

    Baths

  • 2,429

    Sq ft

The story

  • Pool
  • Waterfront

Enter the bougainvillea-lined gates of Casa Feliz, a private oceanfront retreat on Grassy Key offering expansive water views, a white sand beach, and resort-style living. A strong-producing vacation rental with established history and future bookings in place, this exceptional estate presents an attractive investment opportunity. Set on more than 24,000 square feet of lush grounds with mature landscaping, fruit trees, fresh herbs, and .29 acres of bay bottom, Casa Feliz is designed for relaxation and entertaining. An observation pier provides access for kayaking, paddleboarding, fishing, and enjoying abundant marine life. Dockage is available nearby at Duck Key Marina or Grassy Key Marina, if desired. The property's unique orientation captures both sunrise and sunset views, a rare feature in the Keys. Outdoor amenities include a saltwater pool with cascading waterfalls, spillover spa, and a fully equipped poolside cabana featuring a wet bar, refrigerator, ice maker, and cooking area. A fire table and beachside fire pit offer inviting spaces to gather beneath the stars. Completely renovated down to the studs in 2022, the three-story residence was redesigned to maximize ocean views throughout. Four custom bedroom suites, each with a private en-suite bath, comfortably accommodate guests. The top-floor penthouse suite features a private balcony, 180-degree ocean views, custom 96-inch circular bed, and kitchenette with coffee station. Accordion impact-glass doors create a seamless connection between indoor and outdoor living. The gourmet kitchen features Cafe appliances, an induction cooktop, quartz countertops, mosaic tile backsplash, wine cooler, glass shelving, and multiple dining areas. Additional highlights include a movie theater, library loft, Control4 smart technology, custom millwork, and a mural by a local artist. Come discover why Grassy Key is the place to be.

Facts & features

Home type

Home

Year built

1981

Lot size

1 acres

Price per sq ft

$1,439

Included features

  • Pool

    Yes

  • Cooling

    Ceiling Fan(s)

  • Appliances

    Washer, Stainless Steel Appliance(s), Wine Cooler, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer

  • Flooring

    Tile, Wood

  • Roof

    Metal

  • Lot Information

    Waterfront

  • Exterior

    Storage, Outdoor Shower, Outdoor Kitchen, Lighting, Rain Gutters

  • Sewer

    Public Sewer

Mortgage calculator

Estimated monthly payment

$23,116 /mo

7% rate · 30-yr fixed · 20% down

  • Principal & interest $18,602
  • Property tax $3,495
  • Insurance $1,019

Includes principal, interest, taxes & insurance.

Your Property Journey

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Listing Broker

Ocean Sotheby's International

Broker Name

Ocean Sotheby's International

Agent

Ally Kelley