181 Jonathan Dr, Freeport, FL 32439
SOLD
MAR 11, 2026

181 Jonathan Dr
Freeport, FL 32439

  • 5 Beds
  • 5.5 Baths
  • 5,963 sqft (on 5.26 acres)

$2,500,000

Last Sold: Mar 11, 2026
9% below list $2.75M
$419/sqft
Est. Refi. Payment $14,235/mo*
Refinance Your Home

$2,500,000

Last Sold: Mar 11, 2026
9% below list $2.75M
$419/sqft
Est. Refi. Payment $14,235/mo*
Refinance Your Home
5 Beds
5.5 Baths
5,963 sqft
(on 5.26 acres)

Homes for sale near 181 Jonathan Dr

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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 2.5-acre 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 3,382 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 pantrydesigned 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 2,581 sq ft 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 systemideal 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 quietall 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 growthis is the one that rarely comes along.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from March 12, 2026

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Pool
View
Pond
HOA
None
Price/Sqft
$419/sqft
Listed
180+ days ago

Home Details for 181 Jonathan Dr

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Bedroom, Master Bathroom, Great Room, Kitchen
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5963 Square Feet
Appliances & Utilities
Appliances: Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range Hood, Washer, Gas Water Heater, Tankless Water HeaterDishwasherDisposalDryerLaundry: Washer/Dryer HookupMicrowaveWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central Air,Ceiling Fan(s)Has HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: GasHas a Fireplace
Windows, Doors, Floors & Walls
Window: Double Pane Windows, Window TreatmentsFlooring: HardwoodCommon Walls: No Common Walls
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
View
Has a ViewView: Pond
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: CompositionPatio / Porch: Patio, PorchOther Structures: Guest House, Barn(s)
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageNo Attached GarageParking Spaces: 3Parking: Detached,Oversized,RV Access/Parking
Pool
Pool: Heated, In GroundPool
Frontage
Road Frontage: County RoadNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 2020
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Frame, Siding CmntFbrHrdBrdNot a New ConstructionNot Attached Property
Property Information
Condition: Construction CompleteParcel Number: 211S18140100000340

Price & Status

Price
List Price: $2,750,000Price Per Sqft: $419/sqft
Status Change & Dates
Off Market Date: Fri Oct 31 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: FreeportCommunity: N/A
School Information
Elementary School: FreeportJr High / Middle School: FreeportHigh School: Freeport

Building

Building Area
Building Area: 5963 Square Feet

Lot Information

Lot Area: 5.26 Acres

Miscellaneous

Mls Number: 980553Water ViewWater View: PondAttribution Contact: caleb@scenicsir.com
Last check for updates: about 7 hours ago
Listed by Caleb Midgett
Scenic Sotheby's International Realty
Bought with: Caleb Midgett, (850) 499-3311, Scenic Sotheby's International Realty
Source: ECAOR, MLS#980553

Price History for 181 Jonathan Dr

DatePriceEventSource
03/11/2026$2,500,000Sold
ECAOR #980553
11/12/2025$2,750,000PendingECAOR #980553
08/11/2025$2,750,000PriceChange
ECAOR #980553
07/09/2025$3,250,000Listed For SaleECAOR #980553
12/19/2017$120,000Sold
N/A
02/19/2014$97,200Sold
N/A
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Property Tax and Assessment

Year2024
Tax$5,124
Assessment$769,935
Home facts updated by county records

Comparable Sales for 181 Jonathan Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
158 Bentgrass Rd S, Freeport, FL
1.06
Single-Family Home
$475,000
04/17/26
4
3
2,518
1023 Coastal Breeze Dr, Freeport, FL
1.17
Single-Family Home
$552,000
02/27/26
4
3
3,231
973 Coastal Breeze Dr, Freeport, FL
1.22
Single-Family Home
$541,990
03/31/26
4
3
3,231
943 Coastal Breeze Dr, Freeport, FL
1.24
Single-Family Home
$536,000
03/31/26
4
3
3,231
144 Bentgrass Rd N, Freeport, FL
1.20
Single-Family Home
$436,000
01/16/26
4
3
2,750
983 Coastal Breeze Dr, Freeport, FL
1.20
Single-Family Home
$483,990
02/27/26
4
3
2,512
588 Windswept Blvd, Freeport, FL
1.45
Single-Family Home
$683,000
01/28/26
4
3
3,448
836 Coastal Breeze Dr, Freeport, FL
1.31
Single-Family Home
$445,490
02/27/26
4
3
2,512

Assigned Schools

These are the assigned schools for 181 Jonathan Dr.
View nearby schools on GreatSchools
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 Freeport

At least 61 Trulia users voted on each feature.

  • 91 % Say parking is easy

  • 87 % Say car is needed

  • 86 % Say yards are well-kept

  • 85 % Say it's dog friendly

  • 79 % Say it's quiet

  • 78 % Say there's holiday spirit

  • 67 % Say kids play outside

  • 63 % Say there's wildlife

  • 62 % Say people would walk alone at night

  • 56 % Say neighbors are friendly

  • 56 % Say they plan to stay for at least 5 years

  • 51 % Say there are sidewalks

  • 38 % Say streets are well-lit

  • 36 % Say there are community events

  • 26 % Say it's walkable to grocery stores

  • 15 % Say it's walkable to restaurants

Learn more about our methodology.
  • Nwflconnelly
    "Mix of old and new. Lots of green belt areas. Wildlife is prevalent and a part of the neighborhood "
    0
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  • Nwflconnelly
    "Watch out for coyotes and owls. This area is very rural. Also, there are no sidewalks in the neighborhood."
    0
    Flag
  • Julie Fletcher
    "There is no public transportation, so it must have a car to get anywhere outside of the town. Could possibly bike a walk to other businesses in the area. But the town has gotten pretty spread out so that might be difficult."
    0
    Flag
  • Nwflconnelly
    "The street is quiet and we have water views. The wildlife still has room to roam and maintain the natural habitat "
    0
    Flag
  • Julie Fletcher
    "I’ve lived here for four years people. It’s very family friendly. Schools are great and get A ratings. Neighbors are kind and courteous. We are 30 minutes from the sugar, white sand beaches of the Gulf of Mexico, and just 10 minutes from the Bay. There are a lot of nature and walking trails in the area. This is a great place to live if you’d like to go, boating, kayaking, paddle boarding or fishing. So many great spots in the area."
    0
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  • Julie Fletcher
    "It’s very family friendly, with low crime and relatively clean living. Close to the grocery store and various other local restaurants and boutiques."
    0
    Flag
  • Luis A.
    "I LIVE IN FREEPORT AND I CAN SAY ITS THE MOST PEACEFULL LITTLE TOWN I HAVE EVER LIVED IN, BEACHES AR LESS THEN 10 MILES AWAY , HAVE ALL THE AMENITIES I NEED AND MORE , BEST PART CRIME FREE AND EVERYONE KNOWS YOU IN OUR COMMUNITY...."
    4
    Flag
  • Tom L.
    "Have have a car minimal access to other transportation - no public transportation options it is located far from the city which is how I like it"
    0
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  • Tom L.
    "It’s Hammock Bay the rest of Freeport is not so nice although the town is growing as more businesses come here."
    1
    Flag
  • Kendra O.
    "Lived in this neighborhood since August 2019. Our little piece of paradise! Gray balance of seclusion, great neighbors, wildlife, bit close to activities and shopping. Snail town living at its best."
    0
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  • India S.
    "There is no access to a dog park. I believe if we had a dog park it would benefit the health of community pets. "
    4
    Flag
  • Leticia
    "Some people are friendly some are arrogant One thing about having a toy here is keep everybody from being trashy they have to bide by the rules that I like that"
    1
    Flag
  • jimw
    "I'm fairly new to Freeport but it's a quiet place and no crime. It's also just 13 miles to the beach and that's what I wanted. "
    0
    Flag
  • Leticia
    "Great place to live Dog farts recreation center three swimming pools tennis courts where community center walking trails"
    0
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  • Tish L.
    "Small, rural town that is about to explode. 30 minutes to beautiful beaches, shopping, and there is always something to do within a short drive."
    0
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  • Cm2rwoodruff
    "The range of ages in the neighborhoods. The diverse backgrounds that everyone comes from. The sense of community pride. "
    0
    Flag
  • Darenhankins
    "Most people use personal vehicles to commute, and usually will travel 20-40 miles to work or school. "
    0
    Flag

LGBTQ Local Legal Protections

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Member number: 28189

Homes for rent near 181 Jonathan Dr

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Off Market Homes Near 181 Jonathan Dr

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181 Jonathan Dr, Freeport, FL 32439 is a 5 bedroom, 6 bathroom, 5,963 sqft single-family home built in 2020. This property is not currently available for sale. 181 Jonathan Dr was last sold on Mar 11, 2026 for $2,500,000 (9% lower than the asking price of $2,750,000). The current Trulia Estimate for 181 Jonathan Dr is $2,500,900.