Osceola Trail
Homes for Sale in Middleburg, FL
All 343 homes for sale in Middleburg, FL · median $339,900 · 321 homes for sale in 32068 · Clay County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 2026, the MLS records 1 closed sale in Osceola Trail in Middleburg, FL, the most recent in September 2013. Across Middleburg as a whole, 941 homes closed in the last 12 months at a median of $315,000, 46 median days on market, with 320 homes for sale today. At that median and Clay County's FY2025-26 rate of 15.05 mills, annual property tax runs about $4,740 ($4,150 with the full homestead exemption).
Osceola Trail sits in Middleburg, out in Clay County where the pace is more rural than the Jacksonville core. With the data we have as of mid-2026, this is a community defined more by location and home condition than by any single price signal, so treat listing-by-listing detail as the thing that moves value here.
For buyers, that means the property in front of you matters more than the ZIP-code average — lot, updates, and condition will drive what you pay. For sellers, it means pricing to your actual home rather than to a neighborhood shorthand. We would want to walk comparable listings with you before setting an expectation either direction.
Figures in this note are as of July 12, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Osceola Trail 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
Osceola Trail is a Middleburg address in Clay County, positioned toward the western, lower-density side of the Northeast Florida market rather than the built-up urban corridors.
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.
Who Osceola Trail is best for.
Best for
- Buyers prioritizing space and a lower-density setting over commute time
- Buyers who want to stay within Clay County
- Buyers willing to evaluate a home on its own condition and lot rather than a neighborhood price average
Probably not for
- Buyers who need a short daily commute to downtown Jacksonville or the Beaches
- Buyers who want a dense, walkable, amenity-rich setting
- Buyers who need a large, deep pool of active inventory to compare against
The market around Osceola Trail
Osceola Trail is too small for its own price trend, so here is the market around it.
In ZIP 32068, 409 homes are on the market and 22% are under contract — a steady corner of Middleburg.
Across Clay County, 1,289 homes are active and 394 pending (23% under contract).
In ZIP 32068 (Middleburg), 1,084 homes closed in the last 12 months at a median of $320K ($185/sq ft), up 2.0% year over year, with a median 45 days on market. Right now 277 active and 85 pending listings put supply at about 3.1 months — a balanced market. See the live ZIP 32068 housing market and the Clay County market.
ZIP and county figures describe the wider market, not Osceola Trail specifically. Momentum Research analysis of MLS records.
The Osceola Trail buying strategy.
If we were buying in Osceola Trail 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 Osceola Trail.
What Middleburg location actually buys you
Middleburg trades commute convenience for space and a quieter setting. Buyers coming from denser parts of Clay or Duval should factor drive times into daily life here — that tradeoff is the core of the value proposition, and it cuts both ways depending on how you use the area.
Because we are working from a limited snapshot, the honest move is to underwrite each home on its own merits: condition, lot, and how it shows against current inventory. We will not manufacture a price story the data does not support.
The location and the amenities are priced into every listing in Osceola Trail. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
We cover Northeast Florida with the realMLS feed and we will tell you plainly when Osceola Trail is not the right fit for your goals. In a smaller, location-driven Middleburg market, that candor — plus a willingness to price and evaluate home by home rather than by averages — is what protects your money.
Osceola Trail in 15 seconds.
Tools for a Osceola Trail 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 Osceola Trail sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Osceola Trail, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Osceola Trail home worth?
Get a no-obligation home value based on real comparable sales in Osceola Trail, 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 Middleburg →
Should you buy in Osceola Trail?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | realMLS records, as of 2026-11-08 |
| Historical depth | Closed-sale records back to 2013 (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 realMLS 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.
Recent Developments in Osceola Trail
Development, infrastructure, retail, and school activity affecting Osceola Trail, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Schools
Clay school district says one-mill referendum renews, not raises, property tax
The Clay County school district says the referendum on the upcoming ballot renews the one-mill levy voters first approved in 2020 at the same rate. The money funds school law enforcement contracts and compensation to retain and attract teachers and support staff. A citizens' advisory committee reviews spending, and the district says non-renewal would leave a funding shortfall.
What it may mean for the marketThe outcome sets school operating funding and staffing support for Clay County without changing the current millage rate. The site is about 11 miles east of Osceola Trail.
Source: Clay Today - October 2026Retail & Dining
Grumpy's opens largest location yet on Fleming Island
Grumpy's opened at 1803 East-West Parkway in the former Dick's Wings and Grill space, with a Oct. 12 grand opening after benefit soft-opening dinners on Oct. 9 and 10. At 5,352 square feet it is the chain's largest of six Northeast Florida locations, seating up to 190. The owners plan a third restaurant.
What it may mean for the marketA large breakfast-and-lunch restaurant filling a vacant East-West Parkway space adds a dining option on Fleming Island. The project is about 10 miles northeast of Osceola Trail, elsewhere in Clay County.
Source: Clay Today - September 2026Infrastructure
County Road 220 widening and Little Black Creek bridge replacement open to traffic in Clay County
The project finished ahead of schedule, with a new four-lane bridge over Little Black Creek replacing a 1947 structure. Phase 1 began in December 2024 with intersection improvements at Rideout Ferry Road, and Phase 2 began in January 2025. Officials say it should ease traffic along the corridor.
What it may mean for the marketA four-lane CR 220 corridor improves commute capacity for Fleming Island and Middleburg area drivers. The site is about 7 miles northeast of Osceola Trail.
Source: News4JAX - June 2026Builder Activity
Hyland Trail to bring over 3,000 homes to Lake Asbury in Clay County
News4Jax reported that Hyland Trail, along with the related Edenbrooke and The Glens communities, will bring more than 3,000 new homes to the Lake Asbury area of Clay County. Homes are being built by Dream Finders, Pulte and Lennar, with a Lodge amenity center featuring a beach-entry pool, splash zone, exercise facility and pickleball courts. Edenbrooke includes an age-restricted, low-maintenance home section.
What it may mean for the marketAdds a large volume of new single-family housing supply and a private amenity center to the Lake Asbury area, expanding for-sale inventory across a range of home sizes and price points. The site is about 4 miles east of Osceola Trail.
Source: News4Jax - June 2026Infrastructure
First Coast Expressway advances as an economic-development corridor across Clay and St. Johns
The First Coast Expressway (State Road 23), a tolled beltway looping around the west and south of the Jacksonville metro, continued to open land for development along its corridor, with the final St. Johns County phase from Interstate 95 to east of County Road 2209 in progress. FDOT held a St. Johns County open house on the final phase in January 2026.
What it may mean for the marketNew limited-access highway capacity shortens commutes and opens adjacent land, changes that have historically shaped where new communities and demand concentrate. The site is about 8 miles east of Osceola Trail.
Source: Jax Daily Record
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.
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The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum listings in Northeast Florida sold at 99.1% of final list price vs. 98.6% for the market, in a median 31 days vs. 41 (realMLS, 12 months to Nov 2026). A Momentum agent can price yours against live local comps.
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