Windover Court
Homes for Sale in Middleburg, FL
True comps, carrying-cost math, and listings before the portals.
Windover Court is a compact pocket of 14 homes in Middleburg, all built between 1986 and 1989, with a median year built of 1987. That narrow construction window means the homes here share a construction generation, so buyer-to-buyer differences will mostly come down to maintenance history, updates, and lot condition rather than the age of the structure itself.
The median living area runs 1,358.5 square feet, a modest footprint that keeps carrying costs and maintenance scope contained rather than sprawling. Ownership here skews owner-occupied, with 57.1% of homes carrying a homestead exemption, which is useful context for anyone trying to gauge how much of this small inventory turns over as investor or seasonal-owner product versus primary-residence sales.
The 60-Second Overview
Windover Court is a small, single-era enclave in Middleburg, Clay County, where every one of its 14 homes was built between 1986 and 1989 - a tight construction window that gives the community unusual consistency in home age and design compared to communities built out over multiple decades.
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 Windover Court is best for.
Best for
- Buyers who want a modest-footprint home in Middleburg built within the 1986-1989 window.
- Owner-occupant buyers comfortable in a small, owner-occupied-leaning community rather than an investor-heavy one.
- Buyers who prioritize a consistent construction era over amenity packages.
Probably not for
- Buyers who need confirmed community amenities like a pool or clubhouse as part of the purchase.
- Buyers who want a wide selection of comparable listings to shop within the same community.
- Buyers seeking new construction or homes built well outside the 1986-1989 window.
The market around Windover Court
Windover Court is too small for its own price trend, so here is the market around it.
In ZIP 32068, 455 homes are on the market and 29% are under contract — a steady corner of Middleburg.
Across Clay County, 1,286 homes are active and 456 pending (26% under contract).
ZIP and county figures describe the wider market, not Windover Court specifically. Momentum Research analysis of MLS records.
Windover Court by the numbers
From county property records and closed MLS sales for the Windover Court subdivision: 10 homes on record; built 1987–1989; typical size about 1,358 heated sq ft; 3 bedrooms is the median. Housing mix: single-family 100%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2017 | 1 | $112,000 |
| 2018 | 1 | $142,000 |
| 2019 | 2 | $147,500 |
| 2020 | 1 | $192,000 |
| 2021 | 3 | $250,000 |
| 2024 | 1 | $285,000 |
Newest recorded sale: $285,000 on 2024-10-21.
Recorded data as of 2026-09-12; counts cover addresses tagged to this subdivision in the public record, not every parcel. Not an appraisal.
Housing distress & ownership in Windover Court, Middleburg
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. Source: Data provided by realMLS. Deemed reliable but not guaranteed.
Recent Developments in Windover Court
Development, infrastructure, retail, and school activity affecting Windover Court, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated August 2026.
- June 2026Development
Hillwood contracts with the City of Jacksonville for 192 acres at AllianceFlorida at Cecil Commerce Center
Master developer Hillwood contracted with the City of Jacksonville for 192 acres at AllianceFlorida at Cecil Commerce Center on Jacksonville's Westside, continuing the buildout of the former Naval Air Station Cecil Field into an industrial and logistics park.
What it may mean for the marketContinued absorption of large industrial parcels at Cecil signals sustained employment growth on the Westside, which can support housing demand across nearby communities. The site is about 7 miles east of Windover Court.
Source: Jax Daily Record - 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 project is about 18 miles southeast of Windover Court, elsewhere in Clay County.
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 project is about 21 miles southeast of Windover Court, elsewhere in Clay County.
Source: Jax Daily Record - April 2026Development
Hillwood seeks to mass-grade an AllianceFlorida site for a possible 1 million-square-foot building
Hillwood asked to mass grade a site at AllianceFlorida at Cecil Commerce Center to prepare for a possible 1 million-square-foot building, a step that typically precedes a large industrial or distribution user committing to the Westside park.
What it may mean for the marketA build-ready million-square-foot pad points to a potential large employer on the Westside, the kind of jobs anchor that can lift demand for nearby housing. The site is about 7 miles east of Windover Court.
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.
The Windover Court buying strategy.
If we were buying in Windover Court 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 Windover Court.
A Small, Single-Era Pocket in Middleburg
With only 14 homes on record, Windover Court is one of the smaller named communities we track in Clay County. Every home was built within the 1986-1989 window, and the median year built lands at 1987, so this is a community without the usual mix of original-construction homes sitting next to recent builds. Anyone evaluating a property here should expect to be comparing homes on updates and condition rather than construction era, since the era is effectively fixed.
Current MLS data does not identify any confirmed community amenities for Windover Court, so buyers should not assume pooled recreational features or an HOA-run amenity package are part of ownership here - that needs to be verified property by property. Combined with a median living area of 1,358.5 square feet and a homestead share of 57.1%, the picture is a modest-scale, owner-occupied-leaning pocket rather than an amenity-driven or investor-heavy community.
The location and the amenities are priced into every listing in Windover Court. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
Small, data-thin communities like Windover Court are exactly where local knowledge matters more than portal listings. With only 14 homes and no confirmed amenity package in current MLS data, we verify condition, updates, and homestead status property by property rather than relying on aggregated averages that can be thin or misleading in a market this size.
Windover Court in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Windover Court 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 Windover Court sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windover Court, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Windover Court home worth?
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Should you buy in Windover Court?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | realMLS records, as of 2026-09-12 |
| Historical depth | Closed-sale records back to 2006 (22 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.
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