NOT LISTED FOR SALE

29433 Enterprise Ave Big Pine Key, FL 33043

Estimated Value: $4,526,971 - $5,273,000

4 Beds
5 Baths
3,727 Sq Ft
$1,318/Sq Ft Est. Value

Last Sold February 21, 2025

Last sale price $4,700,000 $1,261 Per Sq Ft

Est. 4% increase in value since last sale

Current estimated payment $27,937/month

25 Days on Market

About This Home

As of February 2025

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:

Last Agent to Sell the Property

Lisa Swanson

The Agency Florida Keys License #BK3226537 Listed on: 01/08/2025

The Agency Florida Keys

Last Buyer's Agent

Lisa Swanson

Coldwell Banker Schmitt Real Estate Co.

Home Details

Home Type

Single Family

Year Built

2007

Lot Details

0.44 Acres

Listing Details

  • Property Type: Residential
  • Style: Single Family
  • First Right of Refusal: No
  • Mandatory HOA: No
  • Dockage Dock: Concrete
  • Dockage Seawall: Concrete
  • Fee Includes: None
  • Key Island: Big Pine Key
  • Limited Representation: No
  • Marathon Neighborhood: N/A
  • Mile Marker: 29.50
  • Min Rental Days: 30.00
  • M L S Identifier: 20060123165453488875000000
  • Pets: Pets Allowed
  • Property Group I D: 19990816212109142258000000
  • Sale Terms: Cash
  • Side: Bay/Gulf
  • State Province: FL
  • Taxes: 32725.55
  • Vehicle Storage: Open Parking, Trailer Storage, Covered Parking, Guest Parking
  • Vehicle Storage Cars: 4+
  • Year Built: 2007
  • Alternate Key Number: 1317845
  • Cooling Heating: Central Air, Ceiling Fans(s)
  • Lot Sq Ft: 19250.00
  • Pool Info: In Ground, Decked, Concrete
  • Pool Info Heated: Yes
  • Porch Balcony: Open Porch/Balcony, Deck, Patio
  • Tax Exemptions: None
  • Building Style Above Flood: Yes
  • Estimated Living Sq Ft: 3727.00
  • Specialty Rooms Guest Servant Qtrs: Legal
  • Sewer Hook Up: Yes
  • Statistical Purposes Only: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Interior Amenities: Drapes/Blinds Incl, Built-in Cabinets, Whirlpool Bath Tub, Storage, Smoke Alarms, Security System, Elevator, Granite Counter Top, Entrance Foyer, Split Bedroom, Cathedral Ceilings, Wet Bar
  • Total Bathrooms: 5.00
  • Full Bathrooms: 4
  • Appliances: Washer, Stainless Steel Appliance(s), Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Refrigerator, Dishwasher, Dryer
  • Floor: Tile, Marble, Carpet, Wood
  • Half Bathrooms: 1
  • Specialty Rooms: Laundry Room, Workshop, Utility Room
  • Windows/Doors: French Doors, Impact Rstnce Window, Impact Rstnce Doors
  • Total Bedrooms: 4

Exterior Features

  • Dockage: Davits
  • Waterfront: Oceanfront, Open Water, Canal Front, Gulf Front, Bay Front
  • Waterfront: Yes
  • Construction: Concrete, Stucco
  • Exterior Features: Gazebo, Storage, Lighting, Hot Tub, Rain Gutters, Detached Guest Qtrs
  • Roof: Metal Roof
  • Waterview: Ocean View, Open Water View, Canal View, Bay/Gulf View
  • Pool: Yes

Utilities

  • Security: On Premises System
  • Utilities: FKAA, Propane, Whole House Generatr, Municipal Sewer
  • Heating: Central

Lot Info

  • Deed Restrictions: Unknown
  • Flood Zone: VE,AE
  • Parcel Number: 00248230-000000
  • Land Size: 1/4 - 1/2 Acre
  • Acres: 0.44

Rental Info

  • Rentals Allowed: With Restrictions
  • Furnished: Furnished

Tax Info

  • Tax Year: 2023

Ownership History

Date Name Owned For Owner Type

Purchase Details

Listed on
Jan 8, 2025
Closed on
Feb 20, 2025
Sold by
Cordless Passion Llc
Bought by
Mjs Revocable Trust and Sinegal
Seller's Agent
Lisa Swanson
The Agency Florida Keys
Buyer's Agent
Lisa Swanson
Coldwell Banker Schmitt Real Estate Co.
List Price
$4,995,000
Sold Price
$4,700,000
Premium/Discount to List
-$295,000
-5.91%
Views
288
Current Estimated Value
$4,911,493

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
$211,493
Avg. Annual Appreciation
4.50%

Purchase Details

Listed on
Jan 1, 2022
Closed on
Apr 4, 2022
Sold by
Key Isle Investments I Llc
Bought by
Cordless Passion Llc
Seller's Agent
Aime Buell
EXP Realty LLC
Buyer's Agent
Caroline Bauer
Ocean Sotheby's International Realty
List Price
$4,950,000
Sold Price
$4,720,000
Premium/Discount to List
-$230,000
-4.65%

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
-0.15%

Purchase Details

Closed on
Aug 6, 2010
Sold by
Hazelbaker Jon N and Hazelbaker Joel S
Bought by
Key Isle Investments I Llc

Purchase Details

Closed on
Jul 30, 2010
Sold by
Hazelbaker Colleen
Bought by
Hazelbaker Jon N

Purchase Details

Closed on
Sep 2, 2003
Sold by
Thisler Roger Dale
Bought by
Hazelbaker Jon N and Hazelbaker Colleen

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$640,000
Interest Rate
4%
Mortgage Type
Unknown

Purchase Details

Closed on
Feb 1, 1975
Bought by
Key Isle Investments I Llc
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
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List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Purchase History

Date Buyer Sale Price Title Company
Mjs Revocable Trust $4,700,000 None Listed On Document
Mjs Revocable Trust $4,700,000 None Listed On Document
Cordless Passion Llc $4,720,000 Christopher B Waldera Pa
Key Isle Investments I Llc -- Attorney
Key Isle Investments I Llc $1,933,400 Attorney
Hazelbaker Jon N -- Attorney
Hazelbaker Jon N $469,000 --
Key Isle Investments I Llc $8,500 --
Source: Public Records

Mortgage History

Date Status Borrower Loan Amount
Previous Owner Hazelbaker Jon N $640,000
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft Prior Sale
02/21/2025 02/21/25 Sold $4,700,000 -5.9% $1,261 / Sq Ft
02/02/2025 02/02/25 Pending -- -- --
01/08/2025 01/08/25 For Sale $4,995,000 +5.8% $1,340 / Sq Ft
04/04/2022 04/04/22 Sold $4,720,000 -4.6% $1,266 / Sq Ft View Prior Sale
03/20/2022 03/20/22 Pending -- -- --
01/01/2022 01/01/22 For Sale $4,950,000 -- $1,328 / Sq Ft
Source: Key West Association of REALTORS®

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $31,621 $3,187,622 $1,163,663 $2,023,959
2024 $32,726 $3,650,239 $1,622,775 $2,027,464
2023 $32,726 $3,777,061 $1,801,800 $1,975,261
2022 $21,672 $3,485,383 $1,487,063 $1,998,320
2021 $16,622 $1,743,165 $577,500 $1,165,665
2020 $16,524 $1,714,706 $534,188 $1,180,518
2019 $15,178 $1,561,877 $519,750 $1,042,127
2018 $15,493 $1,550,146 $505,313 $1,044,833
2017 $14,736 $1,585,225 $0 $0
2016 $13,704 $1,398,110 $0 $0
2015 $12,638 $1,179,916 $0 $0
2014 $13,268 $1,188,008 $0 $0
Source: Public Records

Agents Affiliated with this Home

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Map

Source: Key West Association of REALTORS®

MLS Number: 613037

Key West Association of REALTORS®

APN: 00248230-000000

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