Live Oak Cottages
Homes for Sale in Freeport, FL
All 326 homes for sale in Freeport, FL · median $420,962 · 334 homes for sale in 32439 · Walton County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Emerald Coast MLS
Homes listed or recently sold were built 2025–2026 with 8 new construction; 8 of 8 report an HOA (median $150/mo); none of the 8 geocoded homes sit in a FEMA special flood hazard zone (median elevation 43 ft). As of November 2026, the MLS records 1 closed sale in Live Oak Cottages in Freeport, FL, the most recent in July 2026. Across Freeport as a whole, 802 homes closed in the last 12 months at a median of $393,668, 71 median days on market, with 319 homes for sale today. At that median and Walton County's FY2025-26 rate of 9.758 mills, annual property tax runs about $3,840 ($3,460 with the full homestead exemption).
Price here is driven by condition and vintage more than any single template. With a housing stock that runs from the 1920s to 2023 and a median build near 1982, no two homes are priced off the same math. The median sits at $289,500, but treat that as a midpoint on a wide spread, not a going rate — an updated cottage and a project house can carry very different numbers even on the same street.
The market posture is slow. A median of 114 days on market against only eight closings in the window tells you buyers are taking their time and sellers are not getting quick action. For a buyer, that means room to negotiate and no reason to rush. For a seller, it means pricing to the honest condition of your home and expecting a longer runway before a contract.
Figures in this note are as of July 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Live Oak Cottages right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Live Oak Cottages is a small, varied pocket in Freeport with 46 homes spanning roughly a century of construction — the kind of place where each listing has to be judged on its own merits rather than a neighborhood formula.
Emerald Coast MLS sales records identify 8 homes in Live Oak Cottages that have changed hands since 2025, built between 2025 and 2026 (median 2025), with a median living area of about 1,276 sq ft and a typical 3-bedroom, 2-bath layout; 100% are single-family homes. Source: Emerald Coast MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
County records show 5 qualified sales in Live Oak Cottages across 2024–2024, median $180,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
The setting & the homes.
Aerial and on-site photos of Live Oak Cottages. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Live Oak CottagesPhotos from Emerald Coast MLS listings in Live Oak Cottages; content deemed reliable but not guaranteed.
Who Live Oak Cottages is best for.
Best for
- Buyers who can assess an older home's systems and budget for the work an early-vintage house may need
- Patient buyers who want negotiating leverage in a slow market rather than a bidding contest
- Buyers targeting a modest footprint around 1,500 square feet who value the individual home over community amenities
Probably not for
- Buyers who need shared amenities, since none are identified in the current listings
- Buyers on a tight timeline who cannot absorb a median of 114 days on market
- Buyers who want uniform, new construction and a predictable price per home
The market around Live Oak Cottages
Live Oak Cottages is too small for its own price trend, so here is the market around it.
In ZIP 32439, 448 homes are on the market and 25% are under contract — a steady corner of Freeport.
Across Walton County, 2,879 homes are active and 587 pending (17% under contract).
In ZIP 32439 (Freeport), 238 homes closed in the last 12 months at a median of $375K, with a median 71 days on market. Right now 222 active and 87 pending listings put supply at about 11.2 months — a buyer's market. See the live ZIP 32439 housing market and the Walton County market.
ZIP and county figures describe the wider market, not Live Oak Cottages specifically. Momentum Research analysis of MLS records.
Live Oak Cottages on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Emerald Coast MLS. Map data © OpenStreetMap contributors.
The Live Oak Cottages buying strategy.
If we were buying in Live Oak Cottages today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Live Oak Cottages.
A condition-driven street, not a subdivision
The year-built range is the story: homes going back to the 1920s alongside new construction through 2023, with a median living area around 1,500 square feet. That mix rewards buyers who can read a house — inspect the systems, understand what an older structure needs, and know what recent work is worth. There is no shared aesthetic and no community amenities identified in the current MLS listings, so you are buying the individual home and its lot, full stop.
The homestead share sits just under half, which points to a blend of owner-occupied and non-owner-occupied homes rather than a single dominant use. Combine that with the slow pace of closings and you get a market where good inventory can sit, and where a well-prepared buyer has leverage that faster markets do not offer.
The location and the amenities are priced into every listing in Live Oak Cottages. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a place this varied, the median tells you almost nothing about a specific house. We price and evaluate each home on its actual condition, vintage, and lot — not off a neighborhood average — and in a slow market we help buyers use time and negotiation instead of fighting for scraps. Sellers get an honest read on where their home lands in a wide spread and what it takes to draw a contract.
Live Oak Cottages in 15 seconds.
Tools for a Live Oak Cottages buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Live Oak Cottages sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Live Oak Cottages, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Live Oak Cottages home worth?
Get a no-obligation home value based on real comparable sales in Live Oak Cottages, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Freeport →
| Location | Freeport, Walton County, FL · ZIP 32439 |
|---|---|
| Homes in the community | 46 (FL DOR 2025 assessment roll) |
| Years built | 1920–2023 (median 1981.5) |
| Typical living area | 1,502 sq ft (median) |
| Home types (current listings and sales) | detached single family 100% |
| Amenities listed by sellers | Short Term Rental - Not Allowed, Pets Allowed |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 48% |
Data as of November 9, 2026. Listing data provided by the Emerald Coast Association of REALTORS®. Information is deemed reliable but is not guaranteed by the MLS to be accurate; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Live Oak Cottages key facts,” movewithmomentum.com/neighborhoods/live-oak-cottages, data as of November 9, 2026.
Housing distress & ownership in Live Oak Cottages, Freeport
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Listing data provided by the Emerald Coast Association of REALTORS®. Information is deemed reliable but is not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
More Freeport home searches
- All homes for sale in Freeport, FL
- Homes for sale in Walton County, FL
- Freeport pool homes for sale
- Freeport home values: what is my house worth?
Freeport guides & data
- Market data
- Best neighborhoods (ranked by data)
- Flood zones
- Property taxes (Walton County)
- Homestead exemption (Walton County)
- Home insurance cost
- New construction
- New construction (Walton County)
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
- Florida documentary stamp tax, explained
- Cheapest places to live in Florida
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What it really costs to own in Live Oak Cottages
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | Median $150/month across 8 MLS listings (most billed monthly; 2026-11-11). Dues cover what the documents say they cover; ask for the budget and reserve study. |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Walton County is $1,942/yr (433 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
| Roof and age | Median build year 2025 across 8 listings. Newer roofs and current wind-mitigation features usually mean the lower end of insurance quotes. |
Email me new listings in Live Oak Cottages
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Live Oak Cottages
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Live Oak Cottages will answer, and the answer is published on this page for the next buyer.
Recent Developments in Live Oak Cottages
Development, infrastructure, retail, and school activity affecting Live Oak Cottages, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- September 2026Parks & Amenities
Destin and Okaloosa County agree on management of 4-acre Holiday Isle state park
Destin and Okaloosa County unanimously agreed to back Destin as manager and developer of the roughly four-acre state-acquired park on Holiday Isle near Norriego Point. In return, Destin council voted 5-2 to offer free parking to all Okaloosa County residents at city-owned lots and parks. The deal still requires state Board of Trustees and DEP review.
What it may mean for the marketManagement of the Holiday Isle park and city parking rules will affect public waterfront access and parking in Destin. The site is about 3 miles south of Live Oak Cottages.
Source: Get The Coast - August 2026Infrastructure
Walton commissioners approve up to $4.69 million Westbay Parkway design contract
At its August 17, 2026 meeting, the Walton County Board of County Commissioners approved, on the consent agenda, a contract with Mott MacDonald for Westbay Parkway design not to exceed $4,693,502.38. The same agenda included a $184,117 Dewberry task order for the Santa Clara Regional Beach Access Bramble Grove addition.
What it may mean for the marketDesign work on Westbay Parkway is an early step toward added road capacity in western Walton County. The project is about 21 miles east of Live Oak Cottages, elsewhere in Walton County.
Source: Walton County Government - July 2026Infrastructure
Scenic Walton advances underground utilities and gateway landscape projects
Scenic Walton reported progress on countywide initiatives, including a $200,000 Freeport U.S. 331 gateway landscape project supported by a $100,000 FDOT Highway Beautification Grant, plus a 30A West gateway landscape project and early planning for countywide underground utilities. Funding for the utilities study advanced into Walton County's draft budget for fiscal year 2026 to 2027.
What it may mean for the marketAdvances roadway beautification and stormwater improvements along the Freeport U.S. 331 corridor and the 30A west gateway and lays groundwork for utility resilience upgrades across Walton County. The project is about 22 miles east of Live Oak Cottages, elsewhere in Walton County.
Source: Get The Coast - June 2026Civic
DeSantis signs state budget with funding for Okaloosa County projects
Governor DeSantis signed the state budget that included roughly $15 million for 20 Okaloosa County projects, among them $5 million for the Northwest Florida State College Workforce Innovation Center in Niceville, $1.5 million for Shalimar Bridge Park, and $3 million for Destin road and drainage work. About $7.26 million in other local requests were vetoed.
What it may mean for the marketDirects state funding toward workforce, park, road, and drainage infrastructure across Okaloosa County, supporting public facilities and capacity in Niceville, Shalimar, and Destin. The site is about 6 miles north of Live Oak Cottages.
Source: Get The Coast
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
Frequently Asked Questions
How many homes are in Live Oak Cottages?
What share of Live Oak Cottages is owner-occupied?
When were the homes in Live Oak Cottages built?
Who is the best real estate agent for Live Oak Cottages?
How do I find a top Freeport real estate agent who knows Live Oak Cottages?
Can Momentum Realty connect me with an agent for Live Oak Cottages?
Where is Live Oak Cottages, and what county is it in?
Should you buy in Live Oak Cottages?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Emerald Coast MLS, refreshed twice daily (last: November 10, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 32439)) |
| Under-contract shares | Emerald Coast MLS records, as of 2026-11-09 |
| Historical depth | Closed-sale records back to 2026 (1 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Emerald Coast MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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