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Home > 186 & 165 Bayview Drive, Lower Matecumbe, FL 33036 (MLS# 618449)
$10,900,000
186 & 165 Bayview Drive
Lower Matecumbe, FL 33036
MLS# 618449
6 beds  |  5 baths  |  4394 sqft
 | 
Bird's eye view of Bayview Hideaway
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Bird's eye view of Bayview Hideaway Two lots in ideal location House, extra lot, and 220' of dockage Overview of Bayview Hideaway Front, gated entrance. Front gate and access to property Bird's eye view Front entry Foyer Stairs and open living area Wide open living areas Open living area and kitchen Luxurious living areas Expansive living areas throughout Kitchen and dining areas Wide open living areas and kitchen Spacious kitchen with views of the Bay Kitchen Dining area with serene Bay views Chef's kitchen Dining area with panoramic views Kitchen views Customized kitchen Dining area with panoramic views VIP dining area Dining room of your dreams Front of house and pool KP3050-1471-MLS Large living! Outdoor living area Light, bright, and airy living areas. Serene Bay views Wide open and oversized living areas Stairs and upstairs Second floor views Spacious living areas throughout Primary bedroom Expansive primary bedroom Dreamy primary bedroom Primary bedroom Primary bathroom Primary bathroom Primary bathroom Primary bathroom Primary closet Dreamy Bay views from primary bedroom Bayview Hideaway Bayview bliss Rear of home and an abundance of dockage Immediate access to the Bay Helicopter access! Lower Matecumbe dreaming Majestic property and pool Bayview Hideaway Daily sunsets! Arrive by helicopter! Protected dockage Protected dockage Rear of home Beautiful bayside retreat Outdoor dining area Views for days Indoor/outdoor living areas Guest bedroom 1 Guest bedroom 1 Guest bathroom 1 Guest bathroom 1 (for beds 1&2) Guest bedroom 2 Guest bedroom 3 Guest bathroom 2 (for beds 3&4) Guest bathroom 2 (for beds 3&4) Guest bedroom 4 Bayview Hideaway Gym Shower room Gym Shower room Gym Shower room/bathroom Gym Shower room Gym bathroom Gym Bay views from every area Covered entertaining area near the pool Palatial pool with Bay views! KP3050-1299-MLS Peninsula of paradise Pool with sunset views Evening pool vibes Poolside seating for sunset Covered/shaded front entrance Covered entertaining area Evening pool bliss Paradise Expansive home and protected dockage Immediate access to the Bay Bayview Hideaway vibes! Peaceful point on the Bay Helicopter access. Sunset views! Unobstructed sunset views! Putting green Green space on the Bay Al fresco dining Tackle room and flex space Tackle room and flex space Flex space and storage Elevator and downstairs flex space Putting green on the Bay

Property Description
A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over ½ acre lot with panoramic water views from every room. Offering 220+ linear feet of concrete dockage with three boat lifts, the property is exceptionally suited for large vessels with effortless access to the open Florida Bay/Gulf or Ocean via Channel 5 bridge. Two separate parcels included in this sale, opening options in the future for the fortunate owner that resides here. Completely renovated in 2020, the home presents a clean, contemporary aesthetic with Viking appliances, bespoke finishes, and a subtle, neutral palette inspired by the flowing surrounding turquoise waters. A custom saltwater pool equipped with both heater and chiller provides year-round enjoyment for everyone. This Safety Harbor residence delivers both elegance and function for the discerning boater or sunset lover. Impeccably maintained and move-in ready, it offers a rare combination of low-maintenance living, thoughtful design, quiet living and enduring appeal in the Florida Keys. Private showings available by appointment.

Details
Maps
Documents
Contract Information
Listing Board: Florida Keys
Current Price: $10,900,000
Listing Date: 2026-02-03
List Price: $10,900,000
Location, Tax & Legal
City: ISLAMORADA
Mile Marker: 74
Marathon Neighborhood: N/A
Side: Bay/Gulf
Flood Zone: AE,VE
Alternate Key #: 1480231
Add'l Parcel #1: 1480231
Add'l Parcel #2: 1480061
Zoning: R1 - Residential Single Family
Deed Restrictions: Unknown
Legal: BK 7 LT 1 SAFETY HARBOR PB 3-69 SEC-1 LOWER MATECUMBE KEY OR31-170 OR47-181/183 OR557-953 OR801-1849 OR1198-1125 OR1198-
Taxes: 28959
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 186 & 165
Street Name: Bayview
Street Suffix: Drive
Key/Island: Lower Matecumbe
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Safety Harbor (74.0)
Area: 22 - Lower Matecumbe
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: Yes
Control Depth: 6
Lot Size: 105 X 114 and 105 X 120
Lot SqFt: 24570
Pool: Yes
Lot Sqft Source: Tax Records
Total Units: 0
Acres: 0.56
SqFt Source: Tax Records
Rentals Allowed: With Restrictions
Min Rental Days: 28
Style: Single Family
Year Built: 1991
Living Apx SqFt: 4394
Total Bedrooms: 6
Full Baths: 4
Half Baths: 1
Total Baths: 5
Remarks & Misc
Remarks – Consumer: A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over ½ acre lot with panoramic water views from every room. Offering 220+ linear feet of concrete dockage with three boat lifts, the property is exceptionally suited for large vessels with effortless access to the open Florida Bay/Gulf or Ocean via Channel 5 bridge. Two separate parcels included in this sale, opening options in the future for the fortunate owner that resides here. Completely renovated in 2020, the home presents a clean, contemporary aesthetic with Viking appliances, bespoke finishes, and a subtle, neutral palette inspired by the flowing surrounding turquoise waters. A custom saltwater pool equipped with both heater and chiller provides year-round enjoyment for everyone. This Safety Harbor residence delivers both elegance and function for the discerning boater or sunset lover. Impeccably maintained and move-in ready, it offers a rare combination of low-maintenance living, thoughtful design, quiet living and enduring appeal in the Florida Keys. Private showings available by appointment.
Directions: GPS
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
Dock: Concrete
Boat Lift: 1
Tax Exemptions
Homestead: 1
Appliances
Dishwasher: 1
Disposal: 1
Dryer: 1
Freezer: 1
Ice Machine: 1
Microwave: 1
Oven: 1
Range: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Washer: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Heating
Electric: 1
Waterfront
Bay Front: 1
Gulf Front: 1
Open Water: 1
Waterview
Bay/Gulf View: 1
Open Water View: 1
Floor
Marble: 1
Tile: 1
Interior Features
Built-in Cabinets: 1
Cathedral Ceilings: 1
Drapes/Blinds Incl: 1
Elevator: 1
Entrance Foyer: 1
Smoke Alarms: 1
Split Bedroom: 1
Window Treatments: 1
Property Condition
Updated/Remodeled: 1
Specialty Rooms
Gym: 1
Utility Room: 1
Building Style
Above Flood: Unknown
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Vehicle Storage
Carport: 1
Covered Parking: 1
Guest Parking: 1
Open Parking: 1
RV Parking Open: 1
Construction
CBS: 1
Concrete: 1
Land Size
1/2 - Less Than 1 AC: 1
Furnished
Unfurnished: 1
Utilities
Cable Available: 1
FKAA: 1
Porch/Balcony
Open Porch/Balcony: 1
Screened P/B: 1
Exterior Features
Bar: 1
Fencing: 1
Fruit Tree(s): 1
Gazebo: 1
Outdoor Shower: 1
Shed: 1
Storage: 1
Pool Info
In Ground: 1
Salt Water: 1
Heated: Yes
Pre-Wired
Cable: 1
Roof
Metal Roof: 1
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: Homestead
Waterfront: Bay Front; Gulf Front; Open Water
Waterview: Bay/Gulf View; Open Water View
Dockage: Boat Lift
Property Condition: Updated/Remodeled
Vehicle Storage: Carport; Covered Parking; Guest Parking; Open Parking; RV Parking Open
Furnished: Unfurnished
Cooling: Ceiling Fans(s); Central Air
Utilities: Cable Available; FKAA
Interior Features: Built-in Cabinets; Cathedral Ceilings; Drapes/Blinds Incl; Elevator; Entrance Foyer; Smoke Alarms; Split Bedroom; Window Treatments
Pre-Wired: Cable
Specialty Rooms: Gym; Utility Room
Appliances: Dishwasher; Disposal; Dryer; Freezer; Ice Machine; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer
Exterior Features: Bar; Fencing; Fruit Tree(s); Gazebo; Outdoor Shower; Shed; Storage
Pool Info: In Ground; Salt Water
Construction: CBS; Concrete
Floor: Marble; Tile
Roof: Metal Roof
Pets: Pets Allowed
Land Size: 1/2 - Less Than 1 AC
Listing Office: Ocean Sotheby's International Realty

Last Updated: February - 03 - 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.

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