Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vacation rental history. Situated on 1.82 private acres with approximately 225 feet of ocean frontage, this Residential Estate-zoned property is currently licensed for legal 7-day vacation rentals, making it one of the limited number of properties within the Village of Islamorada offering this highly sought-after privilege.With a documented history as a successful income-producing vacation rental, this property offers the opportunity to enjoy an extraordinary Florida Keys lifestyle while rental income may help offset the costs of ownership.A gated entrance welcomes you through a majestic Royal Palm-lined circular driveway to an impressive, covered portico. Inside, a dramatic foyer and elegant wrought-iron staircase set the tone for a home featuring five spacious bedrooms, four beautifully appointed bathrooms, and breathtaking ocean views throughout.Enjoy spectacular sunrises from the observation pier or relax year-round in the heated and chilled saltwater pool. The home is beautifully appointed with quartz countertops, premium appliances, impact-resistant windows, and exceptional craftsmanship throughout.Whether you're seeking a luxurious private residence or a proven income-producing property to help offset costs, this ideal combination of both is a remarkable Islamorada estate that offers an exceptional blend of privacy, oceanfront beauty, and one of the most desirable licensed weekly vacation rental opportunities in the Florida Keys.
For sale
$3,995,000
87445 Old Hwy, Plantation Key, FL 33036
5beds
4,014sqft
Single Family Residence
Built in 1999
1.82 Acres Lot
$-- Zestimate®
$995/sqft
$-- HOA
What's special
Oceanfront estateGated entranceExceptional craftsmanship throughoutFive spacious bedroomsQuartz countertopsElegant wrought-iron staircaseBreathtaking ocean views throughout
- 13 days |
- 1,042 |
- 75 |
Zillow last checked:
Listing updated:
Listed by:
Cheri Tindall 305-664-7661,
Ocean Sotheby's International Realty,
Leslie Leopold 305-942-0215,
Ocean Sotheby's International Realty
Source: FLKMLS,MLS#: 620430
Originating MLS: Florida Keys
Loading...
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 4
Heating
- Central, Electric
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: More Appliances, Stainless Steel Appliance(s), Microwave, Oven, Refrigerator, Dishwasher, Dryer, Washer
Features
- Quartz Countertops, Entrance Foyer, Split Bedroom
- Flooring: Tile
- Doors: Sliding Glass Doors
- Windows: Drapes/Blinds Incl, Window Treatments, Impact Rstnce Window, Accordion
Interior area
- Total interior livable area: 4,014 sqft
Video & virtual tour
Property
Parking
- Parking features: Garage, Covered, Off Street, Carport
- Has garage: Yes
- Has carport: Yes
Accessibility
- Accessibility features: No
Features
- Levels: 3 Stories
- Stories: 3
- Patio & porch: Open Porch/Balcony, Patio
- Has private pool: Yes
- Pool features: Heated, In Ground, Salt Water
- Fencing: Privacy
- Has view: Yes
- View description: Ocean, Water
- Has water view: Yes
- Water view: Ocean,Water
- Waterfront features: Oceanfront, Open Water, Waterfront, Dockage: Other Dockage
Lot
- Size: 1.82 Acres
- Features: 1 Less Than 2 Acres
Details
- Parcel number: 00415170000000
- Zoning: RE
- Zoning description: Residential Estate
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- CBS, Concrete
- Roof: Metal
Condition
- Year built: 1999
Utilities & green energy
- Sewer: Municipal Sewer, Public Sewer
- Utilities for property: FKAA, Cable Connected
Community & HOA
Community
- Security: Electric Gate, Patrolled Area
- Subdivision: Plant Beach (87.5)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Plantation Key
Financial & listing details
- Price per square foot: $995/sqft
- Tax assessed value: $2,832,663
- Annual tax amount: $23,895
- Date on market: 6/27/2026
Estimated market value
Zestimate®
Not available
Estimated sales range
Not available
Rent Zestimate®
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 6/27/2026 | Listed for sale | $3,995,000$995/sqft |
Source: | ||
| 6/27/2026 | Listing removed | $3,995,000$995/sqft |
Source: | ||
| 1/23/2026 | Listed for sale | $3,995,000-11.1%$995/sqft |
Source: | ||
| 12/5/2025 | Listing removed | $4,495,000$1,120/sqft |
Source: | ||
| 9/9/2025 | Listed for sale | $4,495,000-10%$1,120/sqft |
Source: | ||
| 6/17/2025 | Listing removed | $4,995,000$1,244/sqft |
Source: | ||
| 3/24/2025 | Price change | $4,995,000-9.1%$1,244/sqft |
Source: | ||
| 2/21/2025 | Price change | $5,495,000-8.3%$1,369/sqft |
Source: | ||
| 12/18/2024 | Price change | $5,995,000-4.8%$1,494/sqft |
Source: | ||
| 11/2/2024 | Listed for sale | $6,295,000+57.6%$1,568/sqft |
Source: | ||
| 11/18/2021 | Listing removed | -- |
Source: | ||
| 10/10/2021 | Price change | $3,995,000-4.9%$995/sqft |
Source: | ||
| 7/29/2021 | Price change | $4,199,000-5.6%$1,046/sqft |
Source: | ||
| 5/17/2021 | Listed for sale | $4,450,000+134.2%$1,109/sqft |
Source: | ||
| 4/4/2017 | Sold | $1,900,000-15.6%$473/sqft |
Source: | ||
| 1/20/2017 | Price change | $2,250,000-5.3%$561/sqft |
Source: Freewheeler Realty, Inc #571681 Report a problem | ||
| 8/15/2016 | Listed for sale | $2,375,000-8.6%$592/sqft |
Source: Freewheeler Realty, Inc #571681 Report a problem | ||
| 2/27/2016 | Listing removed | $2,599,000$647/sqft |
Source: Coldwell Banker Schmitt Real Estate Co. #569115 Report a problem | ||
| 6/2/2015 | Listed for sale | $2,599,000+36.8%$647/sqft |
Source: Coldwell Banker Schmitt Islamorada #567651 Report a problem | ||
| 6/11/2005 | Sold | $1,900,000$473/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $23,896 +8.2% | $2,426,610 +10% |
| 2024 | $22,085 +4.3% | $2,206,009 +10% |
| 2023 | $21,165 +12.3% | $2,005,463 +10% |
| 2022 | $18,848 +11.2% | $1,823,148 +10% |
| 2021 | $16,945 -1.1% | $1,657,407 -0.7% |
| 2020 | $17,131 | $1,669,333 +6.4% |
| 2019 | $17,131 -2% | $1,568,872 -8.8% |
| 2018 | $17,487 -7.4% | $1,720,080 -23.3% |
| 2017 | $18,890 -19.8% | $2,243,679 +1.5% |
| 2016 | $23,567 -0.4% | $2,210,509 -1.5% |
| 2015 | $23,661 | $2,243,553 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Principal & interest
$1,547Mortgage insurance
$0Property taxes
$170Home insurance
$105HOA fees
$0Utilities
Not includedAll calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 33036
Nearby schools
GreatSchools rating
- 10/10Plantation Key SchoolGrades: PK-8Distance: 2.2 mi
- 5/10Coral Shores High SchoolGrades: 9-12Distance: 2.4 mi
- $357,9002 bd2 ba1k sqft87465 Old Hwy APT 101, Plantation Key, FL 33036Off Market
Save - $405,0002 bd2 ba1k sqft87465 Old Hwy APT 102, Plantation Key, FL 33036Sold
Save 
- $474,8002 bd2 ba1.1k sqft87465 Old Hwy APT 103, Plantation Key, FL 33036Off Market
Save 
- $361,2002 bd2 ba976 sqft87465 Old Hwy APT 104, Plantation Key, FL 33036Off Market
Save 
- $466,2002 bd2 ba1k sqft87465 Old Hwy APT 105, Plantation Key, FL 33036Off Market
Save - $500,0002 bd2 ba976 sqft87465 Old Hwy APT 106, Plantation Key, FL 33036Sold
Save - $2,5002 bd2 ba976 sqft87465 Old Hwy APT 107, Plantation Key, FL 33036For Rent
Save - $350,4002 bd2 ba982 sqft87465 Old Hwy APT 108, Plantation Key, FL 33036Off Market
Save
A local agent can set up tours, give advice and negotiate with sellers.
Similar homes
- $4,600,0005 bd6 ba3.9k sqft157 Valencia Dr, Plantation Key, FL 33036For Sale
Save
MLS ID #620549, Claire Johnson, Coastal Realty of the Florida Keys. FLKMLS - $3,800,0005 bd3 ba2.4k sqft87950 Overseas Hwy, Plantation Key, FL 33036For Sale
Save
MLS ID #618165, Alina Davis, Coldwell Banker Schmitt Islamorada. FLKMLS - $3,875,0004 bd3 ba3k sqft109 Giardino Dr, Plantation Key, FL 33036For Sale
Save
MLS ID #620412, Alina Davis, Coldwell Banker Schmitt Islamorada. FLKMLS - $3,995,0005 bd3 ba2.6k sqft105 Palo De Oro Dr, Plantation Key, FL 33036For Sale
Save
MLS ID #618653, JAMIE ENGEL, PA, Coldwell Banker Schmitt Islamorada. FLKMLS - $3,900,0003 bd3 ba2.1k sqft131 Bayview Isle Dr, Plantation Key, FL 33036For Sale
Save MLS ID #619454, Alina Davis, Coldwell Banker Schmitt Islamorada. FLKMLS - $4,445,0008 bd4 ba4.6k sqft136 San Remo Dr, Plantation Key, FL 33036For Sale
Save MLS ID #619083, Shane Murray Wilson, Cypress Realty, Inc.. FLKMLS - $3,800,0004 bd5 ba2.5k sqft82779 Old Hwy #8, Islamorada, FL 33036New Construction
Save MLS ID #619186, Sabrina Wampler & Sarah Ewald, Ocean Sotheby's International Realty. FLKMLS - $3,800,0004 bd5 ba2.5k sqft82779 Old Hwy #7, Islamorada, FL 33036New Construction
Save MLS ID #619185, Sabrina Wampler & Sarah Ewald, Ocean Sotheby's International Realty. FLKMLS - $3,800,0004 bd5 ba2.5k sqft82779 Old Hwy #15, Islamorada, FL 33036New Construction
Save MLS ID #619187, Sabrina Wampler & Sarah Ewald, Ocean Sotheby's International Realty. FLKMLS - $3,800,0004 bd5 ba2.5k sqft82779 Old Hwy #14, Islamorada, FL 33036New Construction
Save MLS ID #618400, Sabrina Wampler & Sarah Ewald, Ocean Sotheby's International Realty. FLKMLS - $3,250,0004 bd3 ba3.4k sqft136 Giardino Dr, Plantation Key, FL 33036For Sale
Save MLS ID #616450, Alina Davis, Coldwell Banker Schmitt Islamorada. FLKMLS - $3,750,0004 bd5 ba2.3k sqft154 Redwing Rd, Tavernier, FL 33070For Sale
Save MLS ID #620543, Noemi Camps, Keller Williams Capital Realty - Coral Gables. FLKMLS - $5,493,0004 bd4 ba3k sqft120 Toner Ln, Plantation Key, FL 33036For Sale
Save MLS ID #615862, Kim Bagnell Thaler, Ocean Sotheby's International Realty. FLKMLS - $3,595,0006 bd4 ba3.3k sqft74051 Overseas Hwy, Islamorada, FL 33036For Sale
Save MLS ID #620406, Carolyn C Ambler, American Caribbean Real Estate, Christie's International Real Estate. FLKMLS - $3,999,9994 bd4 ba2.5k sqft74049 Overseas Hwy, Islamorada, FL 33036For Sale
Save MLS ID #619687, Judy Rossignol, Paradise Florida Keys Real Estate, a Luxury Brand. FLKMLS - $2,695,0005 bd3 ba2.7k sqft113 Villa Bella Dr, Islamorada, FL 33036For Sale
Save MLS ID #620127, The Pinder Team - Jessica & Hank, Berkshire Hathaway HomeServices Keys Real Estate - Islamorada. FLKMLS - $2,400,0003 bd4 ba2.3k sqft316 North Dr, Plantation Key, FL 33036For Sale
Save MLS ID #616205, Anthony Askowitz, RE/MAX All Keys Real Estate. FLKMLS - $3,499,0005 bd6 ba5k sqft141 Canal St, Tavernier, FL 33070For Sale
Save MLS ID #619367, Kim Bagnell Thaler, Ocean Sotheby's International Realty. FLKMLS - $2,950,0003 bd2 ba2.3k sqft149 Lake Rd, Plantation Key, FL 33036For Sale
Save MLS ID #619095, Alina Davis, Coldwell Banker Schmitt Islamorada. FLKMLS - $2,999,0003 bd4 ba3.8k sqft111 Spoonbill Rd, Tavernier, FL 33070For Sale
Save MLS ID #620411, Debra Mott, LoKation Real Estate - Pompano Beach. FLKMLS
- Request a tour
as early as tomorrow at 11:00 am
Contact agent
- Florida
- Monroe County
- Islamorada
- 33036
- 87445 Old Hwy