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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

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$4,700,000
29433 Enterprise Avenue
Big Pine Key, FL 33043
MLS# 613037
Status: Closed
4 beds  |  5 baths  |  3727 sqft

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Sunset views
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Sunset views Twilight Pool Point lot Pool Pool Front Front Front pavered driveway Front Front entrance Pool and spa Lower entry with elevator Main living entrance 29433 Enterprise Ave (web) 109 Media room or office Open living room Kitchen Kitchen Kitchen Kitchen views Kitchen Dining area with panoramic views Dining Cathedral ceilings Living Living 29433 Enterprise Ave (web) 075 Covered deck Media room or office with wet bar Half bath on main level 1st Guest suite 1st Guest suite ensuite bathroom 2nd Guest Suite 2nd Guest suite bathroom Laundry room on main level 2nd level wet bar primary suite Sitting area primary suite Primary suite on 2nd level Primary suite Primary suite Primary suite Primary bathroom Primary bathroom Primary suite views Primary suite deck Primary suite deck Primary suite deck Aerial Lot dimensions Lot lines are approximate Aerial Aerial Sunset gazebo Sunset pool Sunset side Twilight side Twilight front Twilight side Twilight pool Twilight pool Twilight pool Pavered driveway Carport under guest house Pavered driveway Porte couchere - covered driveway Front Front Covered entertaining lanai Pool Covered entertaining area Breezeway to Guest House Guest house front Guest house living Guest house wraparound porch Guest house dining Guest house living Guest house bedroom Guest house living Guest house separate bathroom Guest house separate laundry room Pool Pool sunset Pool sunset Pool Pool Pool Pool Twilight front Twilight main level deck Twilight primary deck Twilight front Twilight Twilight Twilight Guest house twilight Sunset from primary deck Picture perfect Twilight from the water Sunset Aerial

Property Description
Experience the Pinnacle of Coastal Elegance in Big Pine Key! This openwater masterpiece designed by noted architect Glen Gray, is where modern luxury meets tropical serenity. This luxurious 4-bedroom, 4 1/2 -bathroom estate is a testament to impeccable design and indulgent living. Step inside and be greeted by soaring cathedral ceilings, walls of glass, and an open floorplan that flows seamlessly through grand living spaces. A chef's kitchen, outfitted with Viking appliances, custom hickory cabinetry, and granite countertops, is both a culinary haven and a design showpiece. Two spacious ensuite bedrooms and a private study or media room grace the main level, while the second-floor primary suite is a sanctuary of its own, featuring a spa-inspired bathroom, a loft sitting area, and a private balcony with sweeping open water views. A personal elevator connects all levels, ensuring effortless access, while the detached 936 sq. ft. guest cottage—connected by a covered breezeway—offers a private retreat complete with a kitchenette, wraparound balcony, and great room. The outdoor oasis is nothing short of breathtaking. A sparkling custom concrete pool and hot tub, controlled by Aqualink remote systems, sit amid lush tropical landscaping, providing a resort-like setting for relaxation or entertaining. The estate's extensive 332-ft concrete seawall includes two sets of boat davits, a fish-cleaning station, and swimming access, making it a boater's paradise with direct access to pristine waters. No luxury has been overlooked—impact windows and doors, a whole-house generator, and ADT remote security provide peace of mind, while the three-zone A/C system ensures comfort year-round. Situated just 30 miles from Key West and mere minutes from Looe Key Reef, this waterfront estate is your gateway to the best of the Florida Keys lifestyle. Immerse yourself in unrivaled luxury and coastal living-schedule your private tour today.Video: https://n9.cl/flythrough-29433-enterprise

Details
Maps
Contract Information
Current Price: $4,700,000
Listing Date: 2025-01-08
Listing Board: Key West Association
Leased Price Monthly: $4,700,000
Location, Tax & Legal
Street #: 29433
Street Name: Enterprise
Street Suffix: Avenue
Key/Island: Big Pine Key
State/Province: FL
Zip Code: 33043
County: Monroe
Subdivision: Pine Channel Estates (29.5)
Area: 11 - Big Pine Key, No Name Key
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 3
Pool: Yes
Year Built: 2007
Lot SqFt: 19250
Acres: 0.44
Living Apx SqFt: 3727
SqFt Source: Property Data Card
Total Bedrooms: 4
Full Baths: 4
Half Baths: 1
Total Baths: 5
Rentals Allowed: With Restrictions
Min Rental Days: 30
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Dockage
Dock Length: 332
Dock: Concrete
Seawall: Concrete
Specialty Rooms
Guest/Servant Qtrs: Legal
Building Style
Above Flood: Yes
Vehicle Storage
Car(s): 4+
Pool Info
Heated: Yes
Status Change Info
Under Contract Date: 2025-02-02
Leased Date: 2025-02-21
Leased Price Monthly: $4,700,000
Status: Closed
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Bay Front; Canal Front; Gulf Front; Oceanfront; Open Water
Waterview: Bay/Gulf View; Canal View; Ocean View; Open Water View
Dockage: Davits
Vehicle Storage: Covered Parking; Guest Parking; Open Parking; Trailer Storage
Furnished: Furnished
Cooling: Ceiling Fans(s); Central Air
Heating: Central
Utilities: FKAA; Municipal Sewer; Propane; Whole House Generatr
Interior Features: Built-in Cabinets; Cathedral Ceilings; Drapes/Blinds Incl; Elevator; Entrance Foyer; Granite Counter Top; Security System; Smoke Alarms; Split Bedroom; Storage; Wet Bar; Whirlpool Bath Tub
Specialty Rooms: Laundry Room; Utility Room; Workshop
Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Microwave; Oven; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler
Exterior Features: Detached Guest Qtrs; Gazebo; Hot Tub; Lighting; Rain Gutters; Storage
Pool Info: In Ground; Concrete; Decked
Construction: Concrete; Stucco
Floor: Carpet; Marble; Tile; Wood
Roof: Metal Roof
Pets: Pets Allowed
Security: On Premises System
Land Size: 1/4 - 1/2 Acre

Listing Office: Berkshire Hathaway HomeServices Knight & Gardner Realty

Last Updated: October - 03 - 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.


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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)