81906 Overseas Highway 2, Upper Matecumbe Key Islamorada, FL 33036 (MLS# 617838)

81906 Overseas Highway 2, Upper Matecumbe Key Islamorada, FL 33036

$2,495,000
Property Type: Residential Bedrooms: 3 Baths: 4 Square Footage: 1,829 Lot Size (sq. ft.): 2,593 Status: Active
Current Price: $2,495,000 List Date: 12/26/2025 Last Modified: 9/28/2026

Overview

Description

Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places you in downtown Islamorada--just a short stroll to the area's most celebrated restaurants, art galleries, and island attractions. Privately gated and approached by a Chicago paver driveway, this absolutely turn-key 3-bedroom, 3.5-bath residence is part of an exclusive collection of just eight bayfront homes and was completed in 2020 with refined design, upscale finishes, all stainless-steel Bosch appliances, and exceptional craftsmanship throughout. Elegant interiors and thoughtful details create a sophisticated yet relaxed island lifestyle. The home features a private pool with a wood deck at the rear--ideal for entertaining or unwinding in complete privacy, while residents also enjoy access to a community bayfront pool overlooking breathtaking sunset views. An assigned boat slip on the bay provides effortless access to Florida Bay and the Atlantic beyond. Boat lift currently in place can h ...

Listing Details MLS# 617838

Location, Tax & Legal

Street #
81906
Street Name
Overseas
Street Suffix
Highway
Key/Island
Upper Matecumbe Key Islamorada
State/Province
FL
Zip Code
33036
County
Monroe
Subdivision
Strattons (82.5)
Area
23 - Upper Matecumbe

Contract Information

Listing Board
Florida Keys
As is Rght to Inspct
Yes
Potential Short Sale
No
Bank Owned
No
Species List
No

General Property Description

Realtor.COM Type
Residential - Single Family
Style
Single Family
Waterfront
Yes
Control Depth
3
Pool
Yes
Year Built
2020
Total Units
8
Lot SqFt
2593
Lot Sqft Source
Tax Records
Living Apx SqFt
1829
SqFt Source
Tax Records
Total Bedrooms
3
Full Baths
3
Half Baths
Yes
Total Baths
4
Rentals Allowed
Yes
Min Rental Days
7

Association Info

Mandatory Home Owners Asc
Yes
1st Right of Refusal
No
Association Fee $
2988
Assoc/Mnt Fee Per
Quarterly

Dockage

Dock
Composite

More Information

Building Style

Above Flood
Yes
# Stories
2 Stories

Pool Info

Heated
Yes

Financial Status

Bank Owned
No
Potential Short Sale
No

Property Features

Fee Includes: Common Area Mnt Tax Exemptions: None Waterfront: Bay Front Waterview: Bay/Gulf View; Open Water View Dockage: Assigned Dock; Boat Lift; Boat Slip Property Condition: New Construction Vehicle Storage: Assigned Parking; Off Street Parking Furnished: Negotiable Cooling: Central Air Utilities: Cable Available; Elect Separate Meter; FKAA; Municipal Sewer; Water Separate Meter Interior Features: Built-in Cabinets; Cathedral Ceilings; Entrance Foyer; Quartz Countertops Appliances: Dishwasher; Dryer; Freezer; Oven; Refrigerator; Stainless Steel Appliance(s); Washer Exterior Features: Built-in Grill; Outdoor Kitchen Pool Info: In Ground; Concrete Construction: CBS Floor: Vinyl Roof: Metal Roof Pets: Pets Allowed Neighborhood Feature: Community Pool Security: Electric Gate Land Size: Less Than 1/4 Acre Terms: Cash; Conventional
Listing Office: Ocean Sotheby's International Realty
Last Updated: September - 28 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.