21 Winter Way, Freeport, FL 32439
Property image
Property image
OFF MARKET

21 Winter Way
Freeport, FL 32439

  • 3 Beds
  • 2 Baths
  • 1,869 sqft

$407,800

Trulia Estimate
as of Aug 5, 2026
Est. Refi. Payment $2,492/mo*
Refinance Your Home

$407,800

Trulia Estimate
as of Aug 5, 2026
Est. Refi. Payment $2,492/mo*
Refinance Your Home
3 Beds
2 Baths
1,869 sqft

Local Information

  • Map ViewExplore the area around 21 Winter Way.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2015
Living Area
1,869 sqft
Price/Sqft
$218
Parking
Garage

About this House

Come buy our CAITLYN ready to start construction in March or build your own personal one in our Hammock Bay community located in Freeport FL. The CAITLYN offers 1869 SF of relaxed living space with a very open plan including 3 bedrooms and 2 baths. As you enter the home from the covered front porch the foyer leads to a hallway with the two secondary bedrooms. Continue to the oversized Great room which flows in to a Dining area and the open Kitchen. Boasting luxurious finishes and detail by Holiday Builders the CAITLYN is a versatile and bright floor plan. Add your personal touch to the Kitchen which has tile floors, granite countertops, plenty of 42" cabinets and an island. The Master suite is a large bedroom and bath with double sink vanity, large shower and walk in closet. The
21 Winter Way, Freeport, FL 32439 is a 3 bedroom, 2 bathroom, 1,869 sqft single-family home built in 2015. It last sold for $221,078 on Sep 21, 2015. It is currently off market. The Trulia Estimate is $407,800, with a rent estimate of $2,449/month.

Home Details for 21 Winter Way

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Tile
Interior Details
Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherMicrowave

Exterior Features

Exterior Home Features
Roof: OtherPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2015
Property Type / Style
Property Type: Single Family HomeArchitecture: Craftsman

Price History for 21 Winter Way

DatePriceEventSource
09/21/2015$221,078Sold
Navarre Area BOR #721666
05/27/2015$227,990ListingRemovedAgent Provided
01/24/2015$227,990Listed For SaleAgent Provided

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 21 Winter Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
100 Camellia Ct, Freeport, FL
0.23
Single-Family Home
$355,000
06/24/26
3
2
1,714
82 Camellia Ct, Freeport, FL
0.23
Single-Family Home
$345,000
04/02/26
3
2
1,824
70 Melody Ln, Freeport, FL
0.10
Single-Family Home
$268,500
05/28/26
3
3
2,346
160 Concert Ct, Freeport, FL
0.31
Single-Family Home
$380,000
04/06/26
3
2
1,881
63 Camellia Ct, Freeport, FL
0.27
Single-Family Home
$425,000
04/10/26
3
2
1,879
53 Dickens Dr, Freeport, FL
0.27
Single-Family Home
$425,000
07/27/26
3
2
1,817
524 Symphony Way, Freeport, FL
0.40
Single-Family Home
$330,000
03/31/26
3
2
1,976
38 Camellia Ct, Freeport, FL
0.25
Single-Family Home
$439,000
02/27/26
3
2
1,962
48 Barefoot Cv, Freeport, FL
0.12
Single-Family Home
$520,000
06/03/26
3
2.5
2,369
11 Hemingway Ln, Freeport, FL
0.36
Single-Family Home
$390,000
06/22/26
3
2
1,721

Nearby homes

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Assigned Schools

These are the assigned schools for 21 Winter Way.
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 21 Winter Way

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Off Market Homes Near 21 Winter Way

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