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: 12/29/2025

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, 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 hold boats up to 5,000Lbs. Adding to its appeal, 7-day rentals are permitted, making this property a rare and superior investment opportunity in one of Islamorada's most walkable and desirable locations. Whether as a full-time residence, island getaway, or income-producing asset, this home offers an exceptional blend of luxury, lifestyle, and flexibility. Coral Cove is located in an X flood zone, providing additional peace of mind.

More Information MLS# 617838

Contract Information

Current Price: $2,495,000 Listing Date: 2025-12-26 Listing Board: Florida Keys List Price: $2,495,000 As is Rght to Inspct: Yes Potential Short Sale: No Bank Owned: No Species List: No

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

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: 1 Total Baths: 4 Rentals Allowed: Yes Min Rental Days: 7

Status Change Info

Status: Active

Association Info

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

Dockage

Dock: Composite

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: December - 29 - 2025
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