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$449,900
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Property Description
One or more photo(s) has been virtually staged. OWNER MOTIVATED...Architectural Elegance Meets Aviation Lifestyle at 14 Pilot Place ____Welcome to Eagles Landing, an exclusive enclave in Winter Haven where architectural distinction, aviation access, and luxury living come together. This stunning 4-bedroom, 3.5-bath custom home was masterfully derived from the May 1997 Life Magazine Dream Home whom the owner met with Taliesin Architect John Rattenbury, a renowned apprentice of Frank Lloyd Wright to come up with the plans. The home was built by Mark Brown. One of only five custom-built homes in the community, this residence is a true architectural gem-offering over 3,000 square feet of thoughtfully curated living space. Situated on a lushly landscaped .30-acre lot complete with pond and directly across from the community's airplane-shaped pool, this home offers privacy, serenity, and direct proximity to the Winter Haven Airport-perfect for pilots or aviation enthusiasts. Key Features You'll Love: "¢ Private rear-entry garage "¢ Whole-house Generac generator "¢ Hurricane shutters throughout "¢ Andersen double-pane storm windows "¢ Natural gas appliances + on-demand hot water heater Interior Highlights: Step inside to soaring ceilings, skylights, custom wood detailing, and parquet wood flooring that reflects the home's unique architectural heritage. The expansive open-concept layout seamlessly connects living and dining areas, bathed in natural light from oversized windows and anchored by elegant custom features. The gourmet kitchen is a chef's dream with custom cabinetry with pull-outs, high-end stainless steel appliances, gas cooking, and a large central island perfect for casual meals or entertaining guests. The primary suite features its own cozy gas fireplace, large walk-in closet, and spa-style bathroom with a jetted tub, walk-in shower, and dedicated vanity space. Adjacent is a bonus flex room-ideal for a nursery, art studio, or home gym. Additional bedrooms offer ultimate flexibility: "¢ Bedroom 2: Custom built-ins, Murphy bed, and office setup "¢ Bedroom 3: Private guest suite with full bath and walk-in shower "¢ Bedroom 4: Spacious with private access to the half bath and hallway-ideal for guests or multi-generational living. The oversized laundry room includes ample storage, a sink, and even a second fridge/freezer for added convenience. Outdoor Oasis: Relax in the enclosed lanai with a built-in fireplace, enjoy the tranquil pond and waterfall (yes, fish included!), or unwind in the charming outdoor seating area surrounded by lush landscaping for maximum privacy. Prime Location for Aviation Lovers: Located just steps from the Winter Haven Airport, this is a rare opportunity to live in a community tailored for those who take to the skies. Whether you're a pilot, aviation hobbyist, or simply appreciate unique architecture and luxury amenities, this home checks every box. 14 Pilot Place is more than a home-it's a lifestyle. Don't miss your chance to own a piece of architectural history in one of Winter Haven's most desirable neighborhoods. Be sure to check out the 3D Virtual tour and schedule your private showing today! Only buyers with proof of funds or a preapproval letter will be allowed access to the home.
Full Property Details
Full Property Details for 14 Pilot Pl
General
- Price: $449,900
- HOA FEE: $83/month
- HOA FEE FREQ.: Annually
- Taxes: $2,734 (2024)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: P4935800
- Updated: 12/10/2025
- Added to Site: 157 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 13
- Interior Features: Built-in Features, Ceiling Fan(s), High Ceilings, Primary Bedroom Main Floor, Skylight(s), Split Bedroom, Thermostat, Walk-In Closet(s), Window Treatments
- Fireplace: Yes
- Fireplace(s): Gas, Other Room, Master Bedroom
- Appliances: Built-In Oven, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
- Furnishings: Unfurnished
- Flooring: Parquet, Porcelain Tile
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Gas Dryer Hookup, Inside, Laundry Room, Washer Hookup
Additional Information
- Shared Amenities: Pool
Exterior
- Exterior Features: Hurricane Shutters, Irrigation System, Private Mailbox, Sliding Doors
- Deck/Patio: Enclosed, Patio
- Porch/Patio/Deck: Enclosed, Patio
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 33881 - Winter Haven / Florence Villa
- County: Polk
- Development Name: 33881 - Winter Haven / Florence Villa
- Subdivision: EAGLES LANDING
- Driving Directions: From Haines City, Head southwest toward Moss Ave 0.2 mi Merge onto US-17 S 1.8 mi Continue straight onto US-17 S/US-92 W 4.9 mi Continue straight onto US-92 W/S Lake Shore Way Continue to follow US-92 W 0.9 mi Turn left onto 21st St NW 1.1 mi Turn right onto Riddle Rd N W 190 ft Turn left onto Pilot Pl Destination will be on the left
- Direction Faces: West
Community
- Community Name: 33881 - Winter Haven / Florence Villa
- Community Features: Airport/Runway, Golf Carts OK, Pool
- Optional Amenities: Pool
- Association: Yes
- Assoc. Name: Michelle Kilcher
- Assoc. Fees Include: Maintenance Grounds, Pool Maintenance, Private Road
- Pet Restrictions: Please check with the HOA
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Natural Gas Connected, Phone Available, Public, Sewer Connected, Water Connected
Structural Information
- Exterior Const.: Block, Stucco
- Roof: Tile
- Windows: Double Pane Windows, Shutters
- Stories/Levels: One
- Square Feet: 2,723
- Sq. Ft. Source: Public Records
- Year Built: 1998
Lot Features
- Lot Size (Acres): 0.3
- Lot Size (Sq. Ft.): 13,051
- Lot Size: 13051
- Street/Road Desc.: Paved
Financial Considerations
- Association Fee: $1,000
- Assoc Fee Freq.: Annually
- Assoc Fee Desc.: Required
- Tax Amount: $2,734
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: EAGLES LANDING PB 97 PGS 30 THRU 32 LOT 20 & INT IN COMMON AREAS
- Flood Zone Info: x
- APN: 262807528102002000
- Property ID: 262807528102002000
Listed by Lpt Realty, Llc
Get Pre-Approved Today
Schools
Schools serving 14 Pilot Pl
School District:Polk County School District
| Name | Grades | Distance |
|---|---|---|
Fred G. Garner Elementary School 2500 Havendale Boulevard Northwest, Winter Haven, FL 33881 | PK-5 | 1 mi |
Westwood Middle School, Winter Haven, FL 3520 Avenue J Northwest, Winter Haven, FL 33881 | 6-8 | 2.1 mi |
Winter Haven Senior High School 600 6th Street Southeast, Winter Haven, FL 33880 | 9-12 | 3.7 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 14 Pilot Pl
Date
Details
Price
Change
Source
11/09/2025
Price Reduced
$449,900
-3.56%
MLS
8/12/2025
Listed
$466,500
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 14 Pilot Pl
Year
Property Taxes
Change
Tax Assessment
Change
2024
$2,734
3%
$191,513
3%
2023
$2,657
—
$185,935
6%
2021
$2,664
—
$175,261
-3%
2022
$2,665
—
$180,519
4%
2021
$2,664
2%
$172,841
2%
2019
$2,608
9%
$168,955
2%
2017
$2,391
—
$165,805
2%
2017
$2,391
1%
$162,395
2%
2016
$2,368
-1%
$159,055
1%
2015
$2,396
—
$157,949
1%
2014
$2,391
—
$156,695
1%
2013
$2,397
—
$154,782
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 14 Pilot Pl
14 Pilot Place, Winter Haven, FL 33881 (MLS# P4935800) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 14 Pilot Place is currently listed for $449,900 and was received on August 12, 2025. Want to learn more about 14 Pilot Place? Do you have questions about finding other Single Family real estate for sale in Winter Haven? You can browse all Winter Haven real estate or contact a Coldwell Banker agent to request more information.

