Hillside
Homes for Sale in Middleburg, FL
True comps, carrying-cost math, and listings before the portals.
Hillside's pricing story is straightforward: a single subdivision built between 1999 and 2003, with a median year built of 2001, so almost every home here is close in age and footprint — median living area runs 2,125 square feet. That consistency shows up in price per square foot, which sits at $187.67 across the community. There isn't a wide range of eras or lot sizes competing against each other; the spread in what a given home sells for comes down mostly to condition and updates, not vintage.
On the market side, the current median list-to-sale window is 10 days, based on closings tracked over the trailing four months — a fast pace for a community of only 53 homes total. With 77.4% of those homes carrying a homestead exemption, most of the housing stock functions as an owner-occupied primary residence rather than a rental, which typically keeps turnover modest even as listings move quickly once priced right.
The 60-Second Overview
Hillside market snapshot (as of September 12, 2026): the median sale price is about $385K ($192 per sq ft over the trailing 12 months of closed sales), and a median 5 days on market for closed sales.
Hillside is a compact, single-era pocket of Middleburg — every home was built between 1999 and 2003 — which gives the community a more uniform look and size range than you'll find in subdivisions built out over multiple decades.
Who Hillside is best for.
Best for
- Buyers targeting a home near the $367,500 median who want move-in-ready construction from the 1999-2003 build era.
- Owner-occupants planning to homestead, matching the 77.4% of the community that already does.
- Buyers who prioritize a fast-moving, well-priced market and are ready to act within days, not weeks.
Probably not for
- Buyers who want a clubhouse, pool, or other built-in community amenities — none are identified here.
- Buyers wanting a wide spread of home ages, styles, or lot sizes to choose from.
- Investors seeking a large, varied inventory pool — only 53 homes make up the entire community.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level realMLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($385K) IS the median in the snapshot above.
Windows contain 0 to 5 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Source: Data provided by realMLS. Deemed reliable but not guaranteed.
29% of homes for sale in ZIP 32068 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-09-12).
Housing distress & ownership in Hillside, 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.
Schools
- Clay County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Middleburg High School (Clay County District Schools); verify by address · High
- Wilkinson Junior High School (verify by address)FLDOE grade A · Middle
- Middleburg Elementary School (verify by address)FLDOE grade B · Elementary
Grades are official Florida Department of Education school grades for 2025-26. Assignments are reported as of the 2025-26 year and can change; always confirm with Clay County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Hillside address.
Recent Developments in Hillside
Development, infrastructure, retail, and school activity affecting Hillside, 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 6 miles northwest of Hillside.
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 11 miles south of Hillside, 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 site is about 11 miles south of Hillside.
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 6 miles northwest of Hillside.
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 Hillside buying strategy.
If we were buying in Hillside 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 Hillside.
The Numbers Behind Hillside
At $187.67 per square foot on a median sale price of $367,500, Hillside prices around what you'd expect for a 2001-built home carrying 2,125 square feet of living space. The 53 homes that make up the community were all built within the same narrow window, so buyers and appraisers alike are comparing very similar product from one listing to the next.
No community amenities are identified from current MLS listings, so pricing here isn't propped up by a clubhouse, pool, or gated entry — it's a reflection of the house itself. With 77.4% of homes carrying a homestead exemption, most of the housing stock functions as an owner-occupied primary residence rather than a rental, which is typically a stabilizing factor in a market moving as fast as this one's 10-day median days on market.
The location and the amenities are priced into every listing in Hillside. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
Hillside is a small, single-vintage community — only 53 homes, with comps that track tightly to the 2,125-square-foot, 2001-built median — where local pricing knowledge does the work an algorithm can't. Momentum tracks the median price per square foot ($187.67) and days on market (10) here in real time, so whether you're pricing a listing or writing an offer in a market moving this fast, you're working from what's actually closing, not a rough estimate.
Hillside 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 Hillside 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 Hillside sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Hillside, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
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Frequently Asked Questions
What is the median home price in Hillside?
How long do homes in Hillside take to sell?
What schools serve Hillside?
Who is the best real estate agent for Hillside?
How do I find a top Middleburg real estate agent who knows Hillside?
Can Momentum Realty connect me with an agent for Hillside?
Should you buy in Hillside?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | realMLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | realMLS records, as of 2026-09-12 |
| Schools | 2025-26 district assignments + FLDOE school grades; verify with the district |
| Historical depth | Closed-sale records back to 2001 (67 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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