Date
Details
Price
Change
Source
9/26/2025
Listed
$6,700,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/84
$6,700,000
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/84
Property Description
Iconic Islamorada Oceanfront Retreat. Welcome to The Last Resort, a one-of-a-kind oceanfront estate offering rare privacy and breathtaking natural beauty in the heart of Islamorada. Set on over an acre of lush tropical land, this coastal retreat boasts 165 feet of private sandy Atlantic beach, where you can launch a kayak or paddleboard right from your backyard and soak in endless turquoise views. Expansive covered verandahs, a 15' x 30' heated seaside pool, and beachside hammocks invite slow, sun-filled days and relaxed gatherings. Across the street, a separate canalfront parcel with a 37.5' concrete dock provides protected deep-water dockage and space for boats, trailers, and water toys - an extraordinary pairing of true beachfront living and convenient boating access. Inside, the home's 3,860 square feet is designed for easy Keys living with generous main-level living areas and bedrooms, plus a spacious upstairs suite with private bath and roof-top deck capturing panoramic ocean vistas. Four bedrooms and five baths accommodate family and guests comfortably, while breezy porches and open gathering spaces make entertaining effortless. Highlights you'll love: 165' of private sandy Atlantic beach with direct ocean entry, 37.5' private concrete dock on canalfront lot for boating convenience, 15' x 30' heated seaside swimming pool with expansive sun decks, over one acre of tropical privacy and mature landscaping, 4 bedrooms | 5 baths | 3,860 sq. ft. with thoughtful single-level layout plus upstairs suite and roof deck. A true Keys treasure, The Last Resort delivers a rare mix of sandy beach, deep-water dockage, and timeless coastal charm. Ann exceptional opportunity to create your own island legacy!
Full Property Details
Full Property Details for 109 Columbus Dr
General
- Price: $6,700,000
- Taxes: $32,715 (2025)
- Status: Active
- Type: Single Family
- Source: 927
- MLS ID: 616619
- Updated: 5/13/2026
- Added to Site: 229 day(s) ago
Interior
- Interior Features: Utility Room, Walk-in Closet(s), Built-in Cabinets, Dade County Pine, Smoke Alarms, Storage
- Appliances: Stainless Steel Appliance(s), Dishwasher, Disposal, Dryer, Microwave, Oven, Range, Refrigerator, Washer, Wine Cooler
- Flooring: Wood, Tile, Laminate
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 5
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared Amenities: Community Boat Ramp
- Pool: Yes
- Pool Description: Concrete, In Ground, Decked
Exterior
- Exterior Features: Lighting, Fencing, Lanai, Sandy Beach, Storage
- Deck/Patio: Roof Top Deck, Open Porch/Balcony, Deck
- Porch/Patio/Deck: Roof Top Deck, Open Porch/Balcony, Deck
Parking
- Parking Features: Open, Guest, Off Street
Location
- Area: 22 - Lower Matecumbe
- County: Monroe
- Subdivision: Mat Ocean View (76.5)
- Driving Directions: MM 76.5-- Ocean Side-- Turn on Columbus Dr & follow road to 109. Home is directly on the ocean on RHS - canal lot 104 across the street
Community
- Assoc. Fees Include: None
- Pets Allowed: Yes
Heating & Cooling
- Central air: Yes
- Air Conditioning: Yes
- Cooling Type: Central Air, Ceiling Fans(s)
- Heating Type: Central
Structural Information
- Architectural Style: Above Flood
- Construction: Frame
- Roof: Metal
- Windows/Doors: French Doors, Glass Doors, Impact Rstnce Doors, Impact Rstnce Window
- Square Feet: 3,860
- Sq. Ft. Source: Property Data Card
- Year Built: 1922
Lot Features
- Property View: Canal, Open Water View, Ocean
- Lot Size (Acres): 1.14
- Lot Size (Sq. Ft.): 49,600
- Lot Size Source: Property Data Card
- Zoning: R1 - Residential Single Family
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Desc.: Canal Front, Oceanfront, Open Water
Financial Considerations
- Tax Amount: $32,715.1
- Tax Year: 2025
- Terms: Cash, Conventional
Disclosures and Reports
- Legal Description: BK 4 LTS 3 & 4 MATECUMBE OCEAN VIEW PB4-102 LOWER MATECUMBE OR475-611 OR805-2073 OR1207-154/168 OR1257-346 OR1298-1038/3
- Flood Zone: AE, VE, AE, VE
- APN: 00396760-000000
Listed by American Caribbean Real Estate, Christie's International Real Estate, KELLY K SHAW PA (305) 664-7303 and American Caribbean Real Estate, Christie's International Real Estate, Joy C Martin (305) 394-7866
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agents
— 109 Columbus Dr —
KELLY K SHAW PA
American Caribbean Real Estate, Christie's International Real Estate
Joy C Martin
American Caribbean Real Estate, Christie's International Real Estate
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 109 Columbus Dr
School District:Monroe County School District, Middle Torch Key, FL
| Name | Grades | Distance |
|---|---|---|
Plantation Key School 100 Lake Road, Tavernier, FL 33070 | PK-8 | 12.9 mi |
Key West High School 2100 Flagler Avenue, Key West, FL 33040 | 9-12 | 71.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 109 Columbus Dr
Tax History
Tax History for 109 Columbus Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$30,787
—
$4,902,686
—
2024
$30,787
1%
$4,900,843
-4%
2023
$30,572
42%
$5,127,776
108%
2021
$21,498
-16%
$2,465,232
-34%
2022
$25,471
18%
$3,730,986
63%
2021
$21,498
21%
$2,290,746
47%
2019
$17,742
2%
$1,557,889
2%
2018
$17,421
—
$1,528,824
-24%
2017
$17,369
7%
$2,014,467
19%
2016
$16,290
14%
$1,686,375
47%
2015
$14,314
12%
$1,148,629
10%
2014
$12,737
10%
$1,044,209
10%
2013
$11,567
—
$949,281
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 109 Columbus Dr
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 5 hours ago
- 4Beds
- 5Total Baths
- 3,284Sq. Ft.
- Single Family
- Active
- Updated 5 hours ago
- 5Beds
- 4Total Baths
- 3,100Sq. Ft.
- Single Family
- Active
- Updated 5 hours ago
- 3Beds
- 3Total Baths
- 1,500Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 1 hour ago
- 4Beds
- 4Total Baths
- 2,409Sq. Ft.
- Townhouse
- Active
- Updated 5 hours ago
- 2Beds
- 2Total Baths
- 1,200Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
109 Columbus Drive, Upper Sugarloaf Key, FL 33036 (MLS# 616619) is a Single Family property with 4 bedrooms and 5 full bathrooms. 109 Columbus Drive is currently listed for $6,700,000 and was received on September 26, 2025. Want to learn more about 109 Columbus Drive? Do you have questions about finding other Single Family real estate for sale in Upper Sugarloaf Key? You can browse all Upper Sugarloaf Key real estate or contact a Coldwell Banker agent to request more information.