Jonathan Drive

Freeport | Florida

The Soul of

Estate Elegance

View Photos Watch Film 360° VTour Open House

Caleb Midgett

Presented At

$2,750,000

Bedrooms

Bathrooms

Living

5,963

SQFT

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181

Jonathan Drive

Freeport | Florida

181 Jonathan Drive , Freeport, FL 32439, Freeport, Florida, United States. , Freeport , Florida

A Truly Rare And Unmatched Opportunity In Freeport, Fl

For those dreaming of being close to the beach—yet far from the crowds—this extraordinary 5-acre estate offers the perfect blend of privacy, space, and future potential. Nestled just 5 miles east of Hwy 331 on scenic Hwy 20, this beautifully crafted homestead is a one-of-a-kind retreat in the heart of fast-growing Freeport. Subdivided into four platted [hidden information] lots, this estate also features 2 additional lots for sale if you're looking to expand for your kids to have houses next door, build additional homes to sell on individual parcels, or simply enjoy the privacy and acreage all to yourself. With approximately 8 acres cleared, a picturesque pond, and a tree-lined entrance, this land is as usable as it is stunning.The 3,300 sq ft custom-built main residence is a showpiece, featuring 4 bedrooms, 4.5 bathrooms, wide-plank white oak floors, shiplap walls, Sierra Pacific windows/doors with white oak interiors, and two oversized porches overlooking serene pasture views. The open-concept kitchen, living, and dining areas include a breakfast nook and a spacious butler’s pantry—designed for everyday comfort and elegant entertaining.Step outside to find a 16’x32’ resort-style pool with shellstone decking, raised garden beds, a fire pit, and ample room for play, relaxation, or gatherings. This is the kind of place where memories are made.A fully climate-controlled 40’x60’ detached garage/workshop offers serious bonus space with a 12’x24’ guest suite and full bath, ninja-coated floors, retractable batting cage, workout zone, storage mezzanine, and Sonos sound system—ideal for hobbies, hosting, or multi-generational living. Plus, a separate 36’x48’ metal pole barn provides plenty of storage for equipment, boats, or recreational gear.Surrounded by upscale equestrian properties and family homesteads, this property supports a lifestyle of gardening, livestock, recreation, or just peace and quiet—all with no HOA and only minutes to Freeport amenities and the white-sand beaches of South Walton.Whether you're looking for a legacy property, a private family compound, or a unique investment with room to grow—this is the one that rarely comes along.

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Property Location

181 Jonathan Drive , Freeport, FL 32439, Freeport, Florida, United States., Freeport Florida

Local Weather & Climate

Freeport, Florida

Current Conditions Updated recently

30 °F

Broken clouds

Feels Like 25°F

Humidity 82%

Wind 5 mph

Visibility 6.2 mi

Sunrise 12:37 PM

Sunset 11:15 PM

5-Day Forecast

Wed 28 Jan

Clouds

High 53°

Low 31°

Thu 29 Jan

Clouds

High 54°

Low 34°

Fri 30 Jan

Clouds

High 58°

Low 46°

Sat 31 Jan

Clouds

High 53°

Low 32°

Sun 1 Feb

Clear

High 41°

Low 23°

Data from OpenWeatherMap

Walkability & Transit Scores

How easy is it to get around Freeport?

Walkability and transit scores for this address come from the EPA National Walkability Index.

Mortgage Calculator

Estimate your monthly payments for this property

Home Price

Down Payment

$100,000

Interest Rate

Loan Term

Estimated Monthly Payment $3,160

Monthly Payment Breakdown

Principal & Interest $2,528

Loan Amount $400,000

Total Interest $337,621

Total Cost $737,621

Potential Tax Benefits (United States)

$0 Est. First Year Interest Deduction

$0 Est. Annual Tax Savings

*Based on post-2017 tax law. Actual deductions depend on filing status, itemization, and current tax laws.

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Important Information

This calculator is for illustrative purposes only and does not constitute a loan offer, pre-approval, or commitment to lend.
Monthly payment estimates do not include property taxes, homeowner's insurance, HOA fees, or other applicable costs which may significantly increase your actual payment.
Interest rates shown are for demonstration only. Actual rates depend on your credit score, down payment, loan type, property location, and current market conditions.
This tool provides estimates only. Consult with a licensed mortgage professional for accurate quotes and personalized advice.
Tax benefit calculations are simplified estimates based on general assumptions for United States. Actual deductions depend on your specific tax situation, filing status, and current tax laws.
Tax Year Information: Tax data shown is based on United States tax year 2025 (fiscal year: January-December), rules effective from 2018 through 2025. Tax laws change frequently and may have been amended since this data was compiled.

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The tax benefit information displayed on this page is provided for general informational and educational purposes only. This information:

Does not constitute tax advice and should not be relied upon as such. Tax laws are complex and vary by jurisdiction, individual circumstances, and are subject to change without notice.
May not be current or accurate for your specific situation. Tax rules are updated frequently by governments, and the information shown may not reflect the most recent changes.
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Should not be used as the basis for any tax planning decisions or financial strategies without consulting a qualified tax professional licensed in your jurisdiction.

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Frequently Asked Questions

Common questions about this property

How many bedrooms and bathrooms does 181 Jonathan Drive , Freeport, FL 32439, Freeport, Florida, United States have?

This house at 181 Jonathan Drive , Freeport, FL 32439, Freeport, Florida, United States features 5 bedrooms with 5,963 square feet of living space.

What is the size of 181 Jonathan Drive , Freeport, FL 32439, Freeport, Florida, United States?

This property offers 5,963 square feet of living space.

What is the listing price for 181 Jonathan Drive , Freeport, FL 32439, Freeport, Florida, United States?

This property is listed at $275,000,000, which equals $46118 per square foot.

What type of property is 181 Jonathan Drive , Freeport, FL 32439, Freeport, Florida, United States?

This is a house located in Freeport, Florida. The property is situated in an established neighborhood with convenient access to local amenities and services.

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