*Under contract with a kickout clause in place, accepting backup offers.* Welcome to 158 Whispering Way in the highly desirable Hammock Bay community of Freeport, Florida. Situated on an oversized 0.41-acre homesite backing to protected preserve land, this beautifully updated 5-bedroom, 3.5-bath home offers the perfect combination of privacy, comfort, and resort-style living. With 2,824 square feet of thoughtfully designed space, this home was built for both everyday living and entertaining. Inside, you'll find a spacious and functional layout with generous living areas, flexible bedroom space, and tasteful updates throughout. Recent improvements include a new roof, freshly painted stucco exterior, hurricane shutters, a brand-new tankless water heater, and a whole-house generator for added peace of mind. Step outside to your own private backyard retreat featuring a heated inground saltwater pool, brand-new deck, basketball court, fully fenced yard, and backyard storage shed. With no rear neighbors and peaceful preserve views, this outdoor space offers the ultimate setting for relaxing, entertaining, or enjoying quiet evenings at home. Located in one of Freeport's premier master-planned communities, Hammock Bay offers an unmatched lifestyle with exceptional amenities including multiple resort-style pools and clubhouses, a state-of-the-art fitness center, tennis, basketball and pickleball courts, miles of walking and biking trails, dog parks, playgrounds, community events, seasonal markets, and the stunning Lake Club overlooking the bay. Conveniently located just minutes from the beaches of 30A and South Walton, shopping, dining, and top-rated schools, this move-in-ready home delivers the best of Florida living in one of the area's most sought-after neighborhoods.
For sale
Price cut: $3.5K (5/27)
$625,000
158 Whispering Way, Freeport, FL 32439
5beds
2,824sqft
Single Family Residence
Built in 2008
0.41 Acres Lot
$607,200 Zestimate®
$221/sqft
$-- HOA
What's special
Fully fenced yardBasketball courtTasteful updates throughoutNew roofHeated inground saltwater poolFlexible bedroom spaceBrand-new deck
- 97 days |
- 1,381 |
- 56 |
Zillow last checked:
Listing updated:
Listed by:
Julie Pruitt-Gann 903-293-5821,
Real Broker LLC,
Richard E Gann 205-412-2687,
Real Broker LLC
Source: ECAOR,MLS#: 999069
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Level: First
- Area: 238 Square Feet
- Dimensions: 17 x 14
Bedroom
- Level: First
- Area: 144 Square Feet
- Dimensions: 12 x 12
Bedroom
- Level: First
- Area: 144 Square Feet
- Dimensions: 12 x 12
Bedroom
- Level: First
- Area: 140 Square Feet
- Dimensions: 14 x 10
Dining room
- Level: First
- Area: 154 Square Feet
- Dimensions: 14 x 11
Great room
- Level: First
- Area: 572 Square Feet
- Dimensions: 26 x 22
Office
- Level: First
- Area: 132 Square Feet
- Dimensions: 12 x 11
Screened porch
- Level: First
- Area: 198 Square Feet
- Dimensions: 22 x 9
Heating
- Natural Gas
Cooling
- Central Air, Ceiling Fan(s)
Appliances
- Included: Cooktop, Disposal, Microwave, Tankless Water Heater
- Laundry: Washer/Dryer Hookup
Features
- Breakfast Bar, Bookcases, Crown Molding, Newly Painted, Pantry, Split Bedroom
- Flooring: Tile
- Windows: Window Treatments
- Attic: Pull Down Stairs
- Has fireplace: Yes
- Fireplace features: Gas
- Common walls with other units/homes: No Common Walls
Interior area
- Total structure area: 2,824
- Total interior livable area: 2,824 sqft
Property
Parking
- Total spaces: 6
- Parking features: Garage Door Opener, Golf Cart Garage, Oversized
- Attached garage spaces: 2.5
Features
- Stories: 1
- Patio & porch: Covered, Enclosed, Screened
- Exterior features: Private Yard, Lawn Pump, Sprinkler System, Rain Gutters
- Has private pool: Yes
- Pool features: Heated, Gunite
- On waterfront: Yes
Lot
- Size: 0.41 Acres
- Dimensions: 100 x 182 x 97 x 183
Details
- Additional structures: Pavillion/Gazebo, Yard Building
- Parcel number: 171S19230400000260
- Zoning description: Resid Single Family
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Craftsman
- Property subtype: Single Family Residence
Materials
- Stucco
- Foundation: Slab
- Roof: Shake
Condition
- Construction Complete
- New construction: No
- Year built: 2008
Utilities & green energy
- Water: Public
Community & HOA
Community
- Features: BBQ Pit/Grill, Community Room, Dock, Fitness Center, Fishing, Game Room, Handball, Pavillion/Gazebo, Picnic Area, Playground, Pool, TV Cable, Tennis Court(s), Waterfront, Pickleball
- Security: Smoke Detector(s)
- Subdivision: HAMMOCK BAY
HOA
- Has HOA: Yes
- Services included: Recreational Faclty, Security, Cable TV
Location
- Region: Freeport
Financial & listing details
- Price per square foot: $221/sqft
- Tax assessed value: $450,612
- Annual tax amount: $4,414
- Date on market: 3/27/2026
Estimated market value
$607,200
$577,000 - $638,000
$4,218/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/27/2026 | Price change | $625,000-0.6%$221/sqft |
Source:  ECAOR #999069 Report a problem | ||
| 3/27/2026 | Listed for sale | $628,500-3.3%$223/sqft |
Source: ECAOR #999069 Report a problem | ||
| 11/3/2025 | Listing removed | $649,900$230/sqft |
Source: ECAOR #982198 Report a problem | ||
| 8/13/2025 | Price change | $649,900-1.5%$230/sqft |
Source: ECAOR #982198 Report a problem | ||
| 8/1/2025 | Listed for sale | $660,000-13.5%$234/sqft |
Source: ECAOR #982198 Report a problem | ||
| 6/13/2023 | Listing removed | -- |
Source: BHHS broker feed Report a problem | ||
| 3/7/2023 | Listed for sale | $763,000+105.5%$270/sqft |
Source: ECAOR #917631 Report a problem | ||
| 7/1/2015 | Sold | $371,300-7.2%$131/sqft |
Source: Public Record Report a problem | ||
| 4/3/2015 | Listed for sale | $399,990+25.8%$142/sqft |
Source: Owner Report a problem | ||
| 12/1/2008 | Sold | $318,000+354.3%$113/sqft |
Source: Public Record Report a problem | ||
| 10/23/2006 | Sold | $70,000$25/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,415 -0.6% | $309,258 +2.9% |
| 2024 | $4,442 +3.8% | $300,542 +3% |
| 2023 | $4,281 +4.1% | $291,788 +3% |
| 2022 | $4,112 +0.2% | $283,289 +3% |
| 2021 | $4,105 +0% | $275,038 +1.4% |
| 2020 | $4,103 +2.4% | $271,241 +2.3% |
| 2019 | $4,008 | $265,143 +1.9% |
| 2018 | $4,008 +1.4% | $260,199 +2.1% |
| 2017 | $3,951 +1.6% | $254,847 +2.1% |
| 2016 | $3,887 +3.3% | $249,605 +2.8% |
| 2015 | $3,763 -17.5% | $242,690 +7.9% |
| 2014 | $4,562 | $224,819 +11.7% |
| 2013 | -- | $201,340 -0.9% |
| 2012 | -- | $203,146 -1.1% |
| 2011 | -- | $205,456 -7.6% |
| 2010 | -- | $222,256 +1% |
| 2009 | -- | $220,019 +199.3% |
| 2008 | -- | $73,500 -36.4% |
| 2007 | -- | $115,500 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 32439
Nearby schools
GreatSchools rating
- 6/10Freeport Elementary SchoolGrades: K-4Distance: 0.8 mi
- 7/10Freeport Middle SchoolGrades: 5-8Distance: 0.8 mi
- 8/10Freeport Senior High SchoolGrades: 9-12Distance: 4.9 mi
Schools provided by the listing agent
- Elementary: Freeport
- Middle: Freeport
- High: Freeport
Source: ECAOR. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Florida
- Walton County
- Freeport
- 32439
- 158 Whispering Way
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