299 E Gray Owl Dr, Freeport, FL 32439
OFF MARKET

299 E Gray Owl Dr
Freeport, FL 32439

  • 4 Beds
  • 2 Baths
  • 2,108 sqft

$392,900

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $2,391/mo*
Refinance Your Home

$392,900

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $2,391/mo*
Refinance Your Home
4 Beds
2 Baths
2,108 sqft

Local Information

  • Map ViewExplore the area around 299 E Gray Owl Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2024
Living Area
2,108 sqft
Price/Sqft
$186
Parking
2 Car Garage

About this House

The Delray is a single story 4 Bed, 2 Bath home with split bedroom plan that is great for family living. The laundry room is nestled with the bedrooms. The open kitchen includes a large walk in pantry and overlooks the dining room and large great room. The bedroom suite is located at the back of the house with double walk in closets and a large ensuite with a low threshold shower. This plan has a spacious back porch great for entertaining. This home includes quartz counter tops, whirlpool range, microwave, and dishwasher.
299 E Gray Owl Dr, Freeport, FL 32439 is a 4 bedroom, 2 bathroom, 2,108 sqft single-family home built in 2024. It last sold for the $377,875 asking price on Nov 14, 2024. It is currently off market. The Trulia Estimate is $392,900, with a rent estimate of $2,819/month.

Home Details for 299 E Gray Owl Dr

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Bedroom, Covered Porch, Dining Area, Kitchen, Laundry, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2108 Square Feet
Appliances & Utilities
Appliances: Dishwasher, DisposalDishwasherDisposalLaundry: Washer/Dryer Hookup
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central Air,Ceiling Fan(s)Has HeatingHeating Fuel: Central
Windows, Doors, Floors & Walls
Flooring: Vinyl, CarpetCommon Walls: No Common Walls
Levels, Entrance, & Accessibility
Stories: 1Floors: Vinyl, Carpet
View
No View
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: CompositionPatio / Porch: CoveredExterior: Sprinkler System, Rain GuttersSprinkler System
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Door Opener,Garage
Frontage
Road Surface Type: PavedNot on Waterfront

Property Information

Year Built
Year Built: 2024
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: Siding Brick Some, Siding CmntFbrHrdBrdNot a New ConstructionNot Attached Property
Property Information
Condition: Under ConstructionParcel Number: 351N19171100AA0170

Price & Status

Price
List Price: $377,875
Status Change & Dates
Off Market Date: Thu Aug 29 2024

Active Status

MLS Status: Sold

Location

Direction & Address
City: FreeportCommunity: Owl's Head Farms
School Information
Elementary School: FreeportJr High / Middle School: FreeportHigh School: Freeport

Building

Building Area
Building Area: 2108 Square Feet

Community

Community Features: Short Term Rental - Not Allowed, Playground, Pool, Pickleball
Other
Playground

HOA

HOA Fee Includes: ManagementHas an HOA

Lot Information

Lot Area: 8276.4 sqft

Miscellaneous

Mls Number: 958538

Additional Information

Short Term Rental - Not AllowedPlaygroundPoolPickleball
Last check for updates: about 1 hour ago
Listed by Eric J Weisbrod
DR Horton Realty of Emerald Coast LLC
Bought with: Kimberly J Nilles, (850) 603-5975, ERA American Real Estate
Source: ECAOR, MLS#958538

Price History for 299 E Gray Owl Dr

DatePriceEventSource
11/14/2024$377,875Sold
ECAOR #958538
09/05/2024$377,875PendingECAOR #958538

Market trends in Freeport

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$357K
$35.83KMoM
Sale-to-List Price
97.0%
0.2%MoM
Price per sq ft
$207
$9MoM
Available listings
336
21MoM
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Comparable Sales for 299 E Gray Owl Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
13 E Gray Owl Dr, Freeport, FL
0.14
Single-Family Home
$407,000
02/27/26
4
2
2,108
64 Grass Owl Loop, Freeport, FL
0.04
Single-Family Home
$425,000
05/29/26
4
3
2,035
214 W Gray Owl Dr, Freeport, FL
0.18
Single-Family Home
$373,900
09/24/25
4
2
2,045
67 Farm Owl Dr W, Freeport, FL
0.07
Single-Family Home
$389,900
03/13/26
4
3
2,035
193 W Gray Owl Dr, Freeport, FL
0.13
Single-Family Home
$367,500
10/23/25
4
2
2,045
36 Gray Owl Dr E, Freeport, FL
0.15
Single-Family Home
$351,308
04/28/26
4
2
2,108
64 Gray Owl Dr E, Freeport, FL
0.16
Single-Family Home
$335,640
05/22/26
4
2
1,856
113 Gray Owl Dr E, Freeport, FL
0.15
Single-Family Home
$398,576
06/30/26
4
2
2,108
39 Gray Owl Dr E, Freeport, FL
0.16
Single-Family Home
$362,042
05/15/26
4
2
2,108
70 W Farm Owl Dr, Freeport, FL
0.06
Single-Family Home
$387,347
03/26/26
4
3
2,377

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Assigned Schools

These are the assigned schools for 299 E Gray Owl 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 there's holiday spirit

  • 79 % Say it's quiet

  • 67 % Say kids play outside

  • 62 % 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

  • 39 % 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

Sourced by Trulia users. Learn more about our methodology.
  • Julie Fletcher
    "4th of July and other community holiday events. Person to person fundraising for the schools and local teams."
    0
    Flag
  • Nwflconnelly
    "Mix of old and new. Lots of green belt areas. Wildlife is prevalent and a part of the neighborhood "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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

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Homes for sale near 299 E Gray Owl Dr

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Off Market Homes Near 299 E Gray Owl Dr

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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