Highland Oaks
Homes for Sale in Middleburg, FL
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 36 closed sales in Highland Oaks in Middleburg, FL since 2001, the most recent in July 2026. Recorded prices since 2024 ran from $298,000 to $308,000 (median $302,500), on homes of 1,564 to 2,187 sq ft. Across Middleburg as a whole, 666 homes closed in the last 12 months at a median of $315,000, 46 median days on market, with 218 homes for sale today. At that median and Clay County's FY2025-26 rate of 15.05 mills, annual property tax runs about $4,550 ($3,960 with the full homestead exemption).
Part of the Highland master-planned community in Orange Park, GA — see all Highland homes for sale (0 listings across 7 villages and sections in the MLS).
Highland Oaks is a tight pocket of Middleburg — just 34 homes, all built between 1987 and 1995 with a median build year of 1990. There's no HOA-run amenity package showing up in current listings, so buyers aren't paying an amenity premium here; what separates one sale from the next comes down to the individual home — updates, lot, condition — inside that fairly narrow build window.
With homestead exemptions on roughly 76.5% of homes, this reads as a majority owner-occupied street rather than an investor-heavy pocket. The trade-off is data: a community this size doesn't generate enough closed sales at any given moment to chart a reliable price trend, so pricing conversations here need a hand-pulled comp set rather than a broad market-report number.
The 60-Second Overview
Highland Oaks is a small, established enclave in Middleburg — 34 homes built out between 1987 and 1995, with a median living area of 1,563 square feet and no clubhouse or amenity package attached to the listings.
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 Highland Oaks is best for.
Best for
- Buyers who want a smaller, single-era home (median build year 1990) without HOA amenity dues
- Buyers comfortable relying on hand-pulled, home-specific comps rather than a broad trend chart
- Buyers targeting a median living area around 1,563 square feet in Middleburg
Probably not for
- Buyers who want a resort-style amenity package (pool, clubhouse) as part of the purchase
- Buyers who need a large, deep dataset of recent closed sales to benchmark price
- Buyers set on new construction rather than a 1987-to-1995 build window
The market around Highland Oaks
Highland Oaks is too small for its own price trend, so here is the market around it.
In ZIP 32068, 459 homes are on the market and 27% are under contract — a steady corner of Middleburg.
Across Clay County, 1,267 homes are active and 451 pending (26% under contract).
ZIP and county figures describe the wider market, not Highland Oaks specifically. Momentum Research analysis of MLS records.
The Highland Oaks buying strategy.
If we were buying in Highland Oaks 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 Highland Oaks.
A Small, Fixed-Era Pocket
Every home in Highland Oaks went up within an eight-year window, 1987 to 1995, with a median build year of 1990 — so buyers are comparing homes of a similar age and construction era rather than mixing decades-old originals with new construction. Median living area sits at 1,563 square feet, putting the typical home here on the smaller side, which matters when comparing it against larger new-build product elsewhere in Clay County.
Current MLS listings show no identified community amenities — no clubhouse, pool, or HOA-run recreation tied to Highland Oaks — so the value proposition is the home and the location, not a shared amenity package. Combined with a homestead share of 76.5%, this reads as a stable, owner-occupied street where turnover tends to be driven by individual circumstances rather than investor cycling.
The location and the amenities are priced into every listing in Highland Oaks. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A community this small — 34 homes total — doesn't show up cleanly in broad market reports, and without a recent closed-sale window to lean on, pricing it right means pulling comps by hand and knowing which nearby Middleburg streets are legitimate stand-ins. That's the legwork we do before we ever put a number in front of a buyer or seller.
Highland Oaks 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 Highland Oaks 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 Highland Oaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Oaks, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Highland Oaks home worth?
Get a no-obligation home value based on real comparable sales in Highland Oaks, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Should you buy in Highland Oaks?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | realMLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2001 (36 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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