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 Café 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.
For sale
Price cut: $155K (8/19)
$3,495,000
58652 Overseas Hwy, Grassy Key, FL 33050
4beds
2,429sqft
Single Family Residence
Built in 1981
0.85 Acres Lot
$3,256,300 Zestimate®
$1,439/sqft
$-- HOA
What's special
Fruit treesLibrary loftFresh herbsPrivate oceanfront retreatBougainvillea-lined gatesCustom millworkWhite sand beach
- 108 days
- 1,423
- 81
Zillow last checked:
Listing updated:
Listed by:
Ally Kelley 727-459-0493,
Ocean Sotheby's International,
Jo Ann Cook 305-360-7968,
Ocean Sotheby's International
Source: FLKMLS,MLS#: 619913
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 4
Cooling
- Ceiling Fans(s)
Appliances
- Included: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Wine Cooler, Stainless Steel Appliance(s)
- Laundry: Laundry Room
Features
- Quartz Countertops
- Flooring: Tile, Wood
- Furnished: Yes
Interior area
- Total structure area: 2,429
- Total interior livable area: 2,429 sqft
Video & virtual tour
Property
Features
- Patio & porch: Open Porch/Balcony
- Exterior features: Built-in Barbecue, Fruit Tree(s), Rain Gutters, Lighting, Outdoor Kitchen, Outdoor Shower, Sandy Beach, Storage, Water Display
- Has private pool: Yes
- Pool features: In Ground, Lap, Concrete, Decked
- Has spa: Yes
- Spa features: Heated
- Fencing: Privacy
- On waterfront: Yes
Lot
- Size: 0.85 Acres
- Dimensions: 60 X 410
Details
- Parcel number: 00366860000000
- Zoning: RM - Residential Medium
- Other equipment: Home Theater, Irrigation Equipment
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- CBS
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1981
Utilities & green energy
- Utilities for property: Cable Available
Community & HOA
Community
- Security: Security System
- Subdivision: Crains Sub (58.0)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Grassy Key
Financial & listing details
- Price per square foot: $1,439/sqft
- Tax assessed value: $1,579,131
- Annual tax amount: $14,033
- Date on market: 5/15/2026
- Listing terms: No Seller Finance
Estimated market value
$3,256,300
$3.09M - $3.42M
$6,137/mo
Price history
| Date | Event | Price |
|---|---|---|
| 8/19/2026 | Price change | $3,495,000-4.2%$1,439/sqft |
Source: | ||
| 7/24/2026 | Price change | $3,650,000-2.7%$1,503/sqft |
Source: | ||
| 6/28/2026 | Price change | $3,750,000-6.1%$1,544/sqft |
Source: | ||
| 5/15/2026 | Listed for sale | $3,995,000+207.3%$1,645/sqft |
Source: | ||
| 6/30/2017 | Sold | $1,300,000-3.7%$535/sqft |
Source: | ||
| 3/28/2017 | Price change | $1,350,000-9.7%$556/sqft |
Source: RE/MAX All Keys (Marathon) Real Estate #573307 Report a problem | ||
| 12/23/2016 | Listed for sale | $1,495,000+121.6%$615/sqft |
Source: RE/MAX All Keys Real Estate #573307 Report a problem | ||
| 1/30/2004 | Sold | $674,500+101.3%$278/sqft |
Source: | ||
| 11/22/2000 | Sold | $335,000$138/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $14,034 -27% | $1,579,131 -23.9% |
| 2024 | $19,228 +56.2% | $2,074,909 +127.7% |
| 2023 | $12,310 +25.5% | $911,309 +10% |
| 2022 | $9,808 +22.9% | $828,463 +10% |
| 2021 | $7,982 +3.9% | $753,148 +2.5% |
| 2020 | $7,683 | $734,789 -2.4% |
| 2019 | $7,683 -2.3% | $752,600 -7.8% |
| 2018 | $7,861 -3.9% | $816,185 -0.8% |
| 2017 | $8,180 +3.9% | $823,135 +2.1% |
| 2016 | $7,870 -1% | $806,205 +0.7% |
| 2015 | $7,949 | $800,601 |
Find assessor info on the county website
Monthly payment
Est. payment





