• Home
  • Property Search
    • Key West Real Estate
      • Key West Homes
      • Key West Condos
      • Key West Townhomes
      • Key West Commercial
      • Key West Land
    • Florida Keys Real Estate
      • Florida Keys Homes
      • Florida Keys Condos
      • Florida Keys Townhomes
      • Florida Keys Commercial
      • Florida Keys Land
    • MLS Search
  • Property Estimate
  • Neighborhoods
    • Casa Marina
    • Golf Club
    • Key Haven
    • Meadows
    • Midtown
    • New Town
    • Old Town
    • Sunset Key
    • Truman Annex
  • Islands
    • Big Coppitt Key
    • Big Pine Key
    • Cudjoe Key
    • Duck Key
    • Islamorada
    • Key Colony Beach
    • Key Largo
    • Lower Matecumbe Key
    • Marathon Key
    • Plantation Key
    • Sugarloaf Key
    • Summerland Key
  • Contact Us

Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

With a portal you are able to:
  1. Save your searches
  2. Get updates on listings
  3. Track listings
  4. Add notes and messages
  5. Personalize your dashboard

$5,250,000
82698 Overseas Highway
Upper Matecumbe Key Islamorada, FL 33036
MLS# 576877
Status: Closed
8 beds  |  6.2 baths  |  5999 sqft


Perfect venue for ceremonies and celebrations!
  1 / 30  
Perfect venue for ceremonies and celebrations! Rare cut-in boat basin and covered boat house. Contemplation Point 4 bedrooms, 4 baths with direct bay views One of 2 gated private driveways Rear view of main house with circle drive. Soaring open beam ceilings, polished tile floors and fireplace. Double sided fireplace, gorgeous tiled floors Living room opens to north wing Hard wood floors, bay views. Each bedroom has ensuite baths Upstairs office with bay views 2 bedrooms, 1 bath French doors leading to screened front porch. Hard wood floors. Screened front porch. Hardwood floors Guest Cottage Bedroom 2 French doors open to bay views. 2 bedrooms, 1 bath Kitchen Guest Cottage Open beam ceilings and tile floors Guest Cottage Bedroom Guest Cottage 2 Bay views from living room Rare protected bayfront boat basin Mature palms, gorgeous bayfront. Flow through boat basin Prime location in the heart of Islamorada Bayfront, Upper Matecumbe Key Over 300' bay frontage

Property Description
Timeless Classic This one-of-a-kind private estate is nestled on 3.48 acres in downtown Islamorada with over 300 feet on the Bay. This enchanting property offers 4 large bedrooms & 4 baths in the main house & two spacious 2 bedrooms/1bath detached guest houses. The bay front includes an enormous deep water boat basin, covered boat house, dockage, & an extraordinary “island” that can be the focal point of sunset celebrations. In the main home, the grand room offers high ceilings with fireplace & formal dining room, family room overlooking the water & 4 master suites. The charming appeal of the guest cottages creates an environment for generations of family & friends to gather. Two car garage, a separate laundry outbuilding, landscaping with fruit trees & gated entry complete this estate

Details
Maps
Contract Information
Current Price: $5,250,000
Listing Date: 2017-09-03
Listing Board: Florida Keys
Leased Price Monthly: $5,250,000
As is Rght to Inspct: Yes
Potential Short Sale: No
Bank Owned: No
Location, Tax & Legal
Street #: 82698
Street Name: Overseas
Street Suffix: Highway
Key/Island: Upper Matecumbe Key Islamorada
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Russell Estates (83.2)
Area: 23 - Upper Matecumbe
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 5
Pool: No
Year Built: 1958
Total Units: 3
Lot SqFt: 152460
Acres: 3.48
Living Apx SqFt: 5999
SqFt Source: Property Data Card
Total Bedrooms: 8
Full Baths: 6
Half Baths: 2
Total Baths: 6.2
Rentals Allowed: With Restrictions
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Dockage
Dock: Concrete
Building Style
Above Flood: Unknown
# Stories: 2 Stories
Vehicle Storage
Car(s): 2
Financial Status
Bank Owned: No
Potential Short Sale: No
Status Change Info
Under Contract Date: 2018-07-23
Leased Date: 2018-08-28
Leased Price Monthly: $5,250,000
Status: Closed
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Bay Front; Gulf Front; Open Water
Waterview: Bay/Gulf View; Open Water View
Dockage: Basin
Building Style: Ground Level
Vehicle Storage: Garage
Furnished: Negotiable
Cooling: Ceiling Fans(s); Ductless; Wall/Window Unit(s)
Utilities: Buyer to Verify; FKAA
Interior Features: Cathedral Ceilings; Dade County Pine; Fireplace(s); Split Bedroom; Storage
Specialty Rooms: Laundry Room; Sun/Florida Room; Workshop
Appliances: Dryer; More Appliances; Range; Refrigerator; Washer
Exterior Features: Detached Guest Qtrs; Fencing; Fruit Tree(s)
Construction: CBS; Combo Construction
Floor: Tile; Wood
Roof: Shingle Roof
Pets: Pets Allowed
Security: Electric Gate; Patrolled Area
Land Size: 2 Less Than 5 Acres
Terms: Buyer Obtain Finance
Title: Title Ins - Buyer

Listing Office: Ocean Sotheby's International Realty

Last Updated: March - 05 - 2025

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.


Search powered by FBS Products
Create A Real Estate Portal
With a portal you are able to:
  1. Save your searches
  2. Get updates on listings
  3. Track listings
  4. Add notes and messages
  5. Personalize your dashboard

Anchor Line Realty on Social Media:

Facebook
Facebook
fb-share-icon
Twitter
Visit Us
Follow Me

E-mail Us Directly

Please provide details below:

  • Home
  • Property Search
  • Property Estimate
  • Neighborhoods
  • Islands
  • Contact Us

Copyright © 2026 · AgentPress Pro on Genesis Framework · WordPress · Log in

David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)