29433 Enterprise Ave, Big Pine Key, FL 33043
Property image
Property image
OFF MARKET

$4,719,300

Trulia Estimate
  • 4 Beds
  • 4.5 Baths
  • 3,727 sqft (on 0.44 acres)

29433 Enterprise Ave, Big Pine Key, FL 33043

Est. Refi. Payment $27,813/mo*
Refinance Your Home
Currently Off Market - Sold Feb 21, 2025 for $4,700,000

Home Value

Trulia Estimate
$4.72M
Since last month
Increased$18K (+0.4%)
Since last year
Decreased$24K (-0.5%)
Since last sale
Increased$34K (+0.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +190% in the last 10 years
MonthEstimated value
2026
August 2026$4.73M
August 2026$4.72M
July 2026$4.72M
June 2026$4.67M
May 2026$4.56M
April 2026$4.62M
March 2026$4.62M
February 2026$4.68M
January 2026$4.64M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.08
Single-Family Home
$1,197,475
12/22/25
3
3
1,608
0.24
Single-Family Home
$1,632,000
04/30/26
3
2.5
2,172
0.84
Single-Family Home
$3,475,000
05/19/26
4
3.5
2,050
0.09
Single-Family Home
$1,334,000
08/03/26
3
2
1,488
0.27
Single-Family Home
$925,000
05/29/26
3
3
2,129
0.09
Single-Family Home
$1,022,500
12/01/25
3
2
1,346
1.15
Single-Family Home
$4,150,000
06/30/26
3
4
4,200
0.24
Single-Family Home
$1,150,000
11/04/25
2
2
1,064
0.14
Single-Family Home
$1,282,000
11/12/25
2
2
1,500

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Local Information

  • Map ViewExplore the area around 29433 Enterprise Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2007
0.44 acre lot
3,727 sqft
$1,266/sqft
Open Parking

About this House

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-enterp
29433 Enterprise Ave, Big Pine Key, FL 33043 is a 4 bedroom, 5 bathroom, 3,727 sqft single-family home built in 2007. It last sold for $4,700,000 on Feb 21, 2025 (6% below the $4,995,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,719,300.
Last check for updates: about 1 hour ago
Listed by Lisa Swanson
Berkshire Hathaway HomeServices Knight & Gardner Realty
Bought with: Berkshire Hathaway HomeServices Knight & Gardner Realty
Source: FLKMLS, MLS#613037

Home Details for 29433 Enterprise Ave

Interior Features

Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3727 Square Feet
Appliances & Utilities
Appliances: Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Disposal, Freezer, Gas Appliances, Wine Cooler, Stainless Steel Appliance(s)DishwasherDisposalDryerLaundry: Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central Air,Ceiling Fans(s)Has HeatingHeating Fuel: Has Heating Unspecified Type
Fireplace & Spa
Spa: HeatedHas a Spa
Windows, Doors, Floors & Walls
Flooring: Tile, Wood, Carpet, Marble
Levels, Entrance, & Accessibility
ElevatorFloors: Tile, Wood, Carpet, Marble
View
No View
Security
Security: On Premises System, Security System

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/Balcony, Deck, PatioOther Structures: Gazebo, Guest HouseExterior: Rain Gutters, Lighting, StorageHas a Private Pool
Parking & Garage
No Attached GarageHas Open ParkingParking: Open,Storage
Pool
Pool: In Ground, Concrete, DeckedPool
Frontage
WaterfrontOn Waterfront

Property Information

Year Built
Year Built: 2007
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Concrete, Stucco
Property Information
Parcel Number: 00248230000000

Price & Status

Price
List Price: $4,995,000

Active Status

MLS Status: Closed

Location

Direction & Address
City: Big Pine KeyCommunity: Pine Channel Estates (29.5)

Building

Building Area
Building Area: 3727 Square Feet

HOA

HOA Fee Includes: NoneNo HOA

Lot Information

Lot Area: 0.44 acres

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 613037

Price and Tax history

DateEventPrice
Feb 21, 2025
Source: FLKMLS #613037
Sold
$4,700,000
Feb 18, 2025
Source: FLKMLS #613037
Pending
$4,995,000
Jan 9, 2025
Source: FLKMLS #613037
Listed For Sale
$4,995,000
Nov 5, 2024
Source: FLKMLS #610380
ListingRemoved
$4,995,000
Nov 1, 2024
Source: Key West AOR #610380
PriceChange
$4,995,000
Price decreased by 6%

Market trends in Big Pine Key

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
90
3
MoM

Around this home

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Big Pine Key

At least 29 Trulia users voted on each feature.
  • 95 % Say it's dog friendly

  • 91 % Say there's wildlife

  • 82 % Say car is needed

  • 82 % Say yards are well-kept

  • 81 % Say parking is easy

  • 76 % Say people would walk alone at night

  • 75 % Say it's quiet

  • 66 % Say there's holiday spirit

  • 62 % Say it's walkable to grocery stores

  • 59 % Say it's walkable to restaurants

  • 55 % Say they plan to stay for at least 5 years

  • 52 % Say neighbors are friendly

  • 43 % Say there are community events

  • 35 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Dawn M.
    "I live in Big Pine Key! Neighbors are friendly but keep to themselves. Lots of wildlife . Pretty safe place. "
  • Dawn M.
    "I do not believe there are community events! If there are I have not gone to any! I love Key Deer Blvd good place to run, walk or jog. Also bike riders there are tons! "
  • Sailjane
    "Yes, they would love the area. No restrictions for size, amount, breed, etc. yards are large so pets have room. There is a dog park down the road, excellent vets, many restaurants are dog friendly. There are pet parades, etc too"
  • Sailjane
    "Great parks, great schools, people are very kind and friendly. The scenery is gorgeous. Key deer, peacocks, cool birds, are all around. This is a great place to vacation to and to live. Water all around and the fishing is spectacular. It is a artistic community and very interesting. "
  • Karen F.
    "We have a nautical flea market as well as a weekend flea market, the wildlife refuge has events and there are various events at the park"
  • Shannon M.
    "friendly neighborhood with lots of wildlife both in the water and on land. nice and quiet and away from the craziness of key West but close enough to visit. nowhere else will you see an endangered key deer in your yard on the same day you have. manatee in your back canal. simply beautiful ❤️"
  • Gwalter
    "A great place to live, fish, hang out and enjoy your friends !! It’s well worth a visit. Come as you are and leave as friends "
  • Chelsea G.
    "Born and raised here in Big Pine. Low crime rate. Small property lots. I like it here because there is a grocery store and a a couple gas stations for easy accessibility. "
  • Katherine V.
    "Home to US Fish and Wildlife nature sanctuary, with star-filled nights and sunny, breezy days year-round. Caring community with good basic services. Bike paths, incredible boating and diving. "
  • Maya T.
    "Quiet area for peace and nature lovers."

LGBTQ Local Legal Protections

MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys MLS.

Frequently asked questions about 29433 Enterprise Ave

  • What is 29433 Enterprise Ave estimated to be worth?
    Trulia's estimated value for 29433 Enterprise Ave in Big Pine Key, FL is $4,719,300.
  • What is the price history for 29433 Enterprise Ave?
    29433 Enterprise Ave in Big Pine Key, FL last sold for $4,700,000 in February 2025.
  • Is Big Pine Key a buyer's or seller's market?
    Big Pine Key is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Big Pine Key?
    Residents describe Big Pine Key, FL as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Big Pine Key, FL.
  • Does 29433 Enterprise Ave have air conditioning?
    Yes, 29433 Enterprise Ave in Big Pine Key, FL has air conditioning.
  • Does 29433 Enterprise Ave have a pool?
    Yes, 29433 Enterprise Ave in Big Pine Key, FL has a pool.

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