$4,719,300
- 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 HomeCurrently Off Market - Sold Feb 21, 2025 for $4,700,000
Home Value
Trulia Estimate
$4.72MSince 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
| Month | Estimated 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.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.03 | - | - | - | - | Off Market | |
0.06 | - | - | - | - | Off Market | |
0.08 | $1,197,475 | 3 | 3 | 1,608 | Recently Sold | |
0.09 | $1,334,000 | 3 | 2 | 1,488 | Recently Sold | |
0.09 | $1,022,500 | 3 | 2 | 1,346 | Recently Sold | |
0.07 | - | - | - | - | Off Market | |
0.07 | - | - | - | - | Off Market | |
0.07 | - | - | - | - | Off Market | |
0.07 | - | - | - | - | Off Market | |
0.07 | - | - | - | - | Off Market | |
0.07 | - | - | - | - | Off Market |
Local Information
-- mins to
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
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 15 hours 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
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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 |
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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 |
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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 |
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Price List Price: $4,995,000 |
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MLS Status: Closed |
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Direction & Address City: Big Pine KeyCommunity: Pine Channel Estates (29.5) |
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Building Area Building Area: 3727 Square Feet |
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HOA Fee Includes: NoneNo HOA |
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Lot Area: 0.44 acres |
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Furnished |
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Mls Number: 613037 |
Price and Tax history
| Date | Event | Price |
|---|---|---|
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% |
Aug 2, 2024 Source: Key West AOR #610380 | PriceChange | $5,299,000 Price decreased by 4% |
Jun 11, 2024 Source: Key West AOR #610380 | Listed For Sale | $5,499,000 |
Apr 4, 2022 Source: FLKMLS #598992 | Sold | $4,720,000 |
Mar 18, 2022 Source: FLKMLS #598992 | Contingent | $4,950,000 |
Jan 1, 2022 Source: FLKMLS #598992 | Listed For Sale | $4,950,000 |
Aug 16, 2010 Source: N/A | Sold | $1,933,400 |
May 17, 2008 Source: Agent Provided | ListingRemoved | $3,850,000 |
Jan 31, 2008 Source: Agent Provided | Listed For Sale | $3,850,000 |
Sep 11, 2003 Source: N/A | Sold | $469,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $28,435 | $3,187,622 |
Home facts updated by county records
Market trends in Big Pine Key
Last updated July 2026
Avg. sale price
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Sale-to-List Price
—
Price per sq ft
—
Available listings
90
3MoM
Around this home
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.
LGBTQ Local Legal Protections
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.

